Homesinorlando.forsale Search Results

$1,589,000

Comfort, charm, and LOCATION are KEY for this unique, one-story, KEY West-style pool home with deeded access to Lake Virginia! Nestled on a brick-lined street in the highly sought-after Virginia Heights neighborhood, this location is truly one-of-a-kind, engulfed in the beloved culture and history of Winter Park, and within true walking distance of Rollins College, Park Avenue, and all the lively bustle of downtown Winter Park. Better yet, enjoy deeded lake access from the neighborhood lakefront park just a 3-minute walk from your front door, where neighbors gather for social events, holiday parties, and relaxing lake views. With a sprawling green lawn, dock, kayak/canoe storage racks, and picnic tables, the perfect daily retreat is just steps away. The home is move-in ready and bursting with charm, with over 2800 SF of thoughtfully designed space for everyday living and entertaining. The ideal, split-bedroom floorplan includes 3 bedrooms, 3 en-suite bathrooms, a private home office (or a 4th bedroom), cozy living room with a wood fireplace (piped for gas), dining room with a built-in lighted bar, large family room, and over 400 SF of covered lanai space overlooking the pool & backyard paradise. The oversized primary suite is truly special, with room for a sitting area, tons of built-in storage, and a mirrored barn door that opens to reveal a custom-designed spa bath, renovated down to studs in 2021. An absolute stunner, the primary bath features a large zero-entry marble shower, custom mahogany-topped vanity, maple board-and-batten walls, brass fixtures, and cypress vaulted ceilings, plus 2 walk-in closets and a third storage closet at the bedroom entrance. The sunny family room extends to the rear of the home, where French doors are equipped with retractable screen doors for enjoying the breeze indoors and out, in true Key-West style. Past the French doors, a travertine lanai stretches across the back of the home and overlooks a lagoon-style pool and travertine deck, with surrounding palms and lush tropical landscaping to create the perfect backyard oasis. The kitchen features Thermador appliances, with a gas cooktop and a brand new vent hood framed by a new marble backsplash, and new pendant lighting over the breakfast bar. Both secondary bedrooms have French doors that open to the covered lanai, and en-suite bathrooms. Other conveniences include a whole-house sound system with interior and exterior speakers, custom laundry room (renovated in 2021), and 2-car garage with built-in storage. Move-in ready, the home was completely replumbed in July 2025, with a new gas water heater, partial roof replacement (all new flat roof in Aug 2025), up-to-date electrical, and (2) recently serviced 2019 HVAC units with UV lights. Ask for list of improvements and a floorplan!

4 Beds ⋅ 3 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Comfort, charm, and LOCATION are KEY for this unique, one-story, KEY West-style pool home with deeded access to Lake Virginia! Nestled on a brick-lined street in the highly sought-after Virginia Heights neighborhood, this location is truly one-of-a-kind, engulfed in the beloved culture and history of Winter Park, and within true walking distance of Rollins College, Park Avenue, and all the lively bustle of downtown Winter Park. Better yet, enjoy deeded lake access from the neighborhood lakefront park just a 3-minute walk from your front door, where neighbors gather for social events, holiday parties, and relaxing lake views. With a sprawling green lawn, dock, kayak/canoe storage racks, and picnic tables, the perfect daily retreat is just steps away. The home is move-in ready and bursting with charm, with over 2800 SF of thoughtfully designed space for everyday living and entertaining. The ideal, split-bedroom floorplan includes 3 bedrooms, 3 en-suite bathrooms, a private home office (or a 4th bedroom), cozy living room with a wood fireplace (piped for gas), dining room with a built-in lighted bar, large family room, and over 400 SF of covered lanai space overlooking the pool & backyard paradise. The oversized primary suite is truly special, with room for a sitting area, tons of built-in storage, and a mirrored barn door that opens to reveal a custom-designed spa bath, renovated down to studs in 2021. An absolute stunner, the primary bath features a large zero-entry marble shower, custom mahogany-topped vanity, maple board-and-batten walls, brass fixtures, and cypress vaulted ceilings, plus 2 walk-in closets and a third storage closet at the bedroom entrance. The sunny family room extends to the rear of the home, where French doors are equipped with retractable screen doors for enjoying the breeze indoors and out, in true Key-West style. Past the French doors, a travertine lanai stretches across the back of the home and overlooks a lagoon-style pool and travertine deck, with surrounding palms and lush tropical landscaping to create the perfect backyard oasis. The kitchen features Thermador appliances, with a gas cooktop and a brand new vent hood framed by a new marble backsplash, and new pendant lighting over the breakfast bar. Both secondary bedrooms have French doors that open to the covered lanai, and en-suite bathrooms. Other conveniences include a whole-house sound system with interior and exterior speakers, custom laundry room (renovated in 2021), and 2-car garage with built-in storage. Move-in ready, the home was completely replumbed in July 2025, with a new gas water heater, partial roof replacement (all new flat roof in Aug 2025), up-to-date electrical, and (2) recently serviced 2019 HVAC units with UV lights. Ask for list of improvements and a floorplan!

1450 Glencoe Road, Winter Park

$1,475,000

Opportunity awaits in the most desirable neighborhood! Buyers have cold feet. Nestled in the Elizabeth’s Walk subdivision in the highly coveted Windsong community of Winter Park, this renovated four-bedroom, four-bathroom pool home offers exceptional privacy and refined updates. Quiet interior street and mature landscaping the home feels secluded. Recent improvements include a new roof (2023), two new AC systems 4-ton Carrier Infinity downstairs and a 2.5-ton Trane upstairs (2025) and fresh exterior and interior paint in the kitchen and bathroom. The updated kitchen features a butcher block island and new cabinetry hardware. Beautiful wine storage room to showcase your finest wines. The newly redesigned powder bath includes hidden storage and a full shower. The living areas are open and welcoming, highlighted by recessed ceilings in the informal living room with distinctive wood beams in the family room giving the home character. The primary suite features dual closets plus a linen closet, fresh paint, new mirrors, tv, lighting, and UV film on doors to keep the suite very cool and save on electrical. The nursery showcases new paint, custom wallpaper, drapes, and remote shades, basically every detail thoughtfully considered. Upstairs, a generous loft serves perfectly as a playroom, exercise room or home office, along with two ensuite bedrooms and a large AC storage room. Outdoor living is private and inviting, with a newly refinished PebbleTec pool finish, new pool coping, gas fireplace, new screen enclosure and professionally updated landscaping (2024). The backyard feels like a personal retreat -quiet, enclosed, and perfect for both relaxing and entertaining. Other features include new insulation (2024), custom aluminum privacy gates with locks, Wi-Fi-enabled Schlage front door lock, touchscreen garage access, Ring cameras, and new thermostats. Living in Windsong offers a sense of community, exclusivity with access to the Winter Park Chain of Lakes, pools, a kids water park area, and playgrounds. Pontoon boat available for residents use. Just minutes from Park Avenue’s shops and restaurants, Baldwin Park, and top-rated schools including Brookshire Elementary, Glenridge Middle, Winter Park High. Great location for private schools- Lake Highland Prep and Trinity Prep.

4 Beds ⋅ 4 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code

Opportunity awaits in the most desirable neighborhood! Buyers have cold feet. Nestled in the Elizabeth’s Walk subdivision in the highly coveted Windsong community of Winter Park, this renovated four-bedroom, four-bathroom pool home offers exceptional privacy and refined updates. Quiet interior street and mature landscaping the home feels secluded. Recent improvements include a new roof (2023), two new AC systems 4-ton Carrier Infinity downstairs and a 2.5-ton Trane upstairs (2025) and fresh exterior and interior paint in the kitchen and bathroom. The updated kitchen features a butcher block island and new cabinetry hardware. Beautiful wine storage room to showcase your finest wines. The newly redesigned powder bath includes hidden storage and a full shower. The living areas are open and welcoming, highlighted by recessed ceilings in the informal living room with distinctive wood beams in the family room giving the home character. The primary suite features dual closets plus a linen closet, fresh paint, new mirrors, tv, lighting, and UV film on doors to keep the suite very cool and save on electrical. The nursery showcases new paint, custom wallpaper, drapes, and remote shades, basically every detail thoughtfully considered. Upstairs, a generous loft serves perfectly as a playroom, exercise room or home office, along with two ensuite bedrooms and a large AC storage room. Outdoor living is private and inviting, with a newly refinished PebbleTec pool finish, new pool coping, gas fireplace, new screen enclosure and professionally updated landscaping (2024). The backyard feels like a personal retreat -quiet, enclosed, and perfect for both relaxing and entertaining. Other features include new insulation (2024), custom aluminum privacy gates with locks, Wi-Fi-enabled Schlage front door lock, touchscreen garage access, Ring cameras, and new thermostats. Living in Windsong offers a sense of community, exclusivity with access to the Winter Park Chain of Lakes, pools, a kids water park area, and playgrounds. Pontoon boat available for residents use. Just minutes from Park Avenue’s shops and restaurants, Baldwin Park, and top-rated schools including Brookshire Elementary, Glenridge Middle, Winter Park High. Great location for private schools- Lake Highland Prep and Trinity Prep.

1408 Chapman Circle, Winter Park

$2,025,000

BACK ON MARKET. Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for a day of kayaking on the Winter Park Chain of Lakes. Welcome to 2299 Via Tuscany, an opportunity priced 4-bedroom, 3.5-bath home to get into the coveted Winter Park Vias while adding your final touches to personalize this home while prioritizing location, schools, privacy and connectivity. With 3,986 square feet on a 0.40-acre lot, it offers the perfect blend of luxury and comfort, featuring a super spacious kitchen, a new architectural shingle roof (2023), Pebble Tec-style pool finish, and lush landscaping. Inside, enjoy solid hardwood and modern tile floors, soaring ceilings, and two wood-burning fireplaces. The chef’s kitchen shines with SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor offers a private primary suite, a guest suite, and a study/library with built-ins, while upstairs you’ll find two more bedrooms and a full bath. Modern perks include zoned A/C, a new EV charger, and epoxy-coated floors in the 2-car garage. Close to parks, the Racquet Club, and downtown Winter Park’s shops, dining, and culture, this home suits families and active lifestyles alike. Deeded lake access through the Maitland Shores Lakefront Preservation Association gives you a private ramp for kayaks, canoes, and more, plus easy access to schools, trails, and green spaces—a perfect mix of charm, amenities, and location.

4 Beds ⋅ 4 Baths ⋅ Maitland Shores SubDv. ⋅ 32789 Zip Code

BACK ON MARKET. Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for a day of kayaking on the Winter Park Chain of Lakes. Welcome to 2299 Via Tuscany, an opportunity priced 4-bedroom, 3.5-bath home to get into the coveted Winter Park Vias while adding your final touches to personalize this home while prioritizing location, schools, privacy and connectivity. With 3,986 square feet on a 0.40-acre lot, it offers the perfect blend of luxury and comfort, featuring a super spacious kitchen, a new architectural shingle roof (2023), Pebble Tec-style pool finish, and lush landscaping. Inside, enjoy solid hardwood and modern tile floors, soaring ceilings, and two wood-burning fireplaces. The chef’s kitchen shines with SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor offers a private primary suite, a guest suite, and a study/library with built-ins, while upstairs you’ll find two more bedrooms and a full bath. Modern perks include zoned A/C, a new EV charger, and epoxy-coated floors in the 2-car garage. Close to parks, the Racquet Club, and downtown Winter Park’s shops, dining, and culture, this home suits families and active lifestyles alike. Deeded lake access through the Maitland Shores Lakefront Preservation Association gives you a private ramp for kayaks, canoes, and more, plus easy access to schools, trails, and green spaces—a perfect mix of charm, amenities, and location.

2299 Via Tuscany, Winter Park

$6,300,000

Quintisential Lake Maitland Estate - first time available. Classic architecture with incredible and thoughtful details throughout. Private setting on over an acre captures sweeping views of Lake Maitland. Sought after location close to Park Avenue. This legacy property embodies the best of Winter Park Lakefront Living.

4 Beds ⋅ 6 Baths ⋅ Camwood SubDv. ⋅ 32789 Zip Code

Quintisential Lake Maitland Estate - first time available. Classic architecture with incredible and thoughtful details throughout. Private setting on over an acre captures sweeping views of Lake Maitland. Sought after location close to Park Avenue. This legacy property embodies the best of Winter Park Lakefront Living.

1308 Green Cove, Winter Park

$630,000

SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

5 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

2612 Roxbury Road, Winter Park

$2,295,000

Introducing a stunning new custom home by Ellsworth Gallimore and Butler Ridge Development, ideally situated in a prime Winter Park neighborhood. This residence combines timeless elegance with modern luxury, showcasing exceptional design and craftsmanship throughout. The thoughtfully designed home features a marble front façade and professional landscaping. Inside, you’ll find an open, bright layout with high ceilings, wide-plank white oak floors, oversized picture windows, and refined crown molding. A welcoming flex space—perfect as a sitting room or den—greets you at the entry, across from another room ideal for a private office. The great room, at the center of the home, offers 12-foot ceilings, a sleek fireplace, and a full wall of sliding glass doors that open to the resort-style backyard. Designed for both entertaining and daily living, the open-concept kitchen, dining, and living areas flow seamlessly together. The chef’s kitchen impresses with a striking waterfall island, premium Thermador appliances, a dual-fuel range with a 6-burner gas cooktop, a third oven plus convection microwave, and an expansive custom pantry. A stylish mudroom and decorative laundry room complete the main level’s amenities. The primary suite on the first floor features direct access to the pool, a spa-inspired bath with a soaking tub, multi-spray shower, dual sinks with a large vanity, and a spacious custom walk-in closet. Upstairs, a loft-style bonus room connects to three additional bedroom suites, each with custom closets and ample storage. Outdoor living includes a saltwater pool with an elegant fountain feature, marble pavers, a summer kitchen with a built-in grill, sink, and beverage fridge, an outdoor bathroom, and a lush grassy area perfect for play or pets. Additional highlights include a two-car garage and zoning for top-rated schools—Lakemont Elementary, Maitland Middle, and Winter Park High. Walk to the Winter Park YMCA and Phelps Park, and enjoy being just minutes from vibrant downtown Winter Park. Elegant design, modern luxury, and a prime location—this exceptional new home offers the very best of Winter Park living.

4 Beds ⋅ 6 Baths ⋅ Winter Park Heights SubDv. ⋅ 32789 Zip Code

Introducing a stunning new custom home by Ellsworth Gallimore and Butler Ridge Development, ideally situated in a prime Winter Park neighborhood. This residence combines timeless elegance with modern luxury, showcasing exceptional design and craftsmanship throughout. The thoughtfully designed home features a marble front façade and professional landscaping. Inside, you’ll find an open, bright layout with high ceilings, wide-plank white oak floors, oversized picture windows, and refined crown molding. A welcoming flex space—perfect as a sitting room or den—greets you at the entry, across from another room ideal for a private office. The great room, at the center of the home, offers 12-foot ceilings, a sleek fireplace, and a full wall of sliding glass doors that open to the resort-style backyard. Designed for both entertaining and daily living, the open-concept kitchen, dining, and living areas flow seamlessly together. The chef’s kitchen impresses with a striking waterfall island, premium Thermador appliances, a dual-fuel range with a 6-burner gas cooktop, a third oven plus convection microwave, and an expansive custom pantry. A stylish mudroom and decorative laundry room complete the main level’s amenities. The primary suite on the first floor features direct access to the pool, a spa-inspired bath with a soaking tub, multi-spray shower, dual sinks with a large vanity, and a spacious custom walk-in closet. Upstairs, a loft-style bonus room connects to three additional bedroom suites, each with custom closets and ample storage. Outdoor living includes a saltwater pool with an elegant fountain feature, marble pavers, a summer kitchen with a built-in grill, sink, and beverage fridge, an outdoor bathroom, and a lush grassy area perfect for play or pets. Additional highlights include a two-car garage and zoning for top-rated schools—Lakemont Elementary, Maitland Middle, and Winter Park High. Walk to the Winter Park YMCA and Phelps Park, and enjoy being just minutes from vibrant downtown Winter Park. Elegant design, modern luxury, and a prime location—this exceptional new home offers the very best of Winter Park living.

1661 Palm Avenue, Winter Park

$630,000

"NEW PRICE" ON THIS MOVE-IN READY, 3-BED, 2-FULL BATHS, SINGLE FAMILY HOME WITH "NO HOA" & LARGE PRIVATE YARD, WINTER PARK, FL 32789. The Seller has already relocated and willing to work with a "Fully Pre-Qualified" Buyer to get this home sold quickly. AWESOME LOCATION just off Corrine Drive. WALKING DISTANCE to East End Market. TOP-RATED Audubon Park (K-8) & Winter Park High (Magnet Program) Schools. The Owners completed a HOME ADDITION & UPDATE in 2020 w/over $115,000.00 of improvements, including a NEW Roof, NEW Primary Bath, EXPANDED Great Room, NEWLY Enclosed Entry way w/mudroom & pantry, along with mechanical & finishing upgrades. Enter the home through a fully ENCLOSED FOYER which allows easy access to the new MUDROOM, as well as the ENORMOUS GREATROOM, which features an open Family & Dining Room area featuring a Wood Burning Fireplace, Decorative Shiplap Niche, Vaulted Ceiling and a dual French Doors leading to the HUGE Patio & Back yard. The CHEF'S KITCHEN was redesigned to include 42" Wood Upper & Lower SHAKER CABINETS w/Soft Close Drawers, Quartz Countertops, HUGE FARM-STYLE Deep Sink, Custom Tile Backsplash, "LG" Stainless Package including a French Style Refrigerator, Flat-Top Range, Microwave, Dishwasher, Wine Refrigerator, Decorative Shelves & a Mid-Century Modern Bungalow Pendant. The Primary Suite is the perfect COUPLES RETREAT which includes a Large Bedroom, Vaulted Ceiling, and a HUGE 14' LONG WALK-IN CLOSET w/Customizable Organizers to store all your Clothes & Accessories. The Primary Bathroom includes HIS & HERS Matching Vanities with Quartz Countertops, Recessed Sinks, Dual Mirrors & Hardware. Enjoy the luxury of a custom jetted soaking tub—ideal for unwinding after a long day or for families with young children, complete with a Tile Backsplash. The "WALK-IN SHOWER" features Frameless Glass, Custom Wall & Floor Tile and an OVERHEAD RAIN SHOWER. Finally, the bathroom features oversized 24"x24" Custom Floor Tile to complete the design features. Do you ENJOY OUTDOOR SPACE & like to Entertain? Do you need a SPACIOUS KIDS AREA for them to safely play? If so, you will FALL-IN-LOVE” with the fully fenced & enclosed back yard featuring two HUGE 12'x21' and 15'x27' OPEN PAVER PATIO areas perfect for all your outdoor furniture & equipment. Also enjoy your own PRIVATE TAVERN with an 8'x12' Bar designed with Corrugated Metal Panels, a Bar Top, Shelving & Concrete Floor. The Bar is OPEN FOR YOUR FRIENDS & FAMILY. The Backyard also includes (2) Separate Gate Entrances which will accommodate & secure your Boat, Trucks, Trailers, Work Equipment, etc. In addition, there is an 8'x8' and 5'x8' Storage Rooms. Addl Features: NEW Roof (2025), NEW Interior & Exterior Paint (2025), Tankless Water heater, Carrier HVAC System (2019), Updated Electric Panel (2019), Updated PEX Plumbing (2019), Newer 8"x36" Custom Tile Flooring, Newer Double Paned Windows (2019), NEW Drain field (2024), Block Construction, HUGE Laundry & Storage Room wCustom Organizers, 6" Baseboards, Window Treatments, Ceiling Fans & Lights, Open Carport (13'x21'), Covered Carport perfect for a Golf Cart (8'x17'), Irrigation System, Gutters & Downspouts, Decorative Bamboo & much more. Just minutes to Park Avenue, Fine Dining, Leu Gardens, Downtown Orlando, Municipal & OIA Airports, Hwy 436, 408, 418, Turnpike, UCF & the Beaches. Call for more info or to schedule your private showing.

3 Beds ⋅ 2 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

"NEW PRICE" ON THIS MOVE-IN READY, 3-BED, 2-FULL BATHS, SINGLE FAMILY HOME WITH "NO HOA" & LARGE PRIVATE YARD, WINTER PARK, FL 32789. The Seller has already relocated and willing to work with a "Fully Pre-Qualified" Buyer to get this home sold quickly. AWESOME LOCATION just off Corrine Drive. WALKING DISTANCE to East End Market. TOP-RATED Audubon Park (K-8) & Winter Park High (Magnet Program) Schools. The Owners completed a HOME ADDITION & UPDATE in 2020 w/over $115,000.00 of improvements, including a NEW Roof, NEW Primary Bath, EXPANDED Great Room, NEWLY Enclosed Entry way w/mudroom & pantry, along with mechanical & finishing upgrades. Enter the home through a fully ENCLOSED FOYER which allows easy access to the new MUDROOM, as well as the ENORMOUS GREATROOM, which features an open Family & Dining Room area featuring a Wood Burning Fireplace, Decorative Shiplap Niche, Vaulted Ceiling and a dual French Doors leading to the HUGE Patio & Back yard. The CHEF'S KITCHEN was redesigned to include 42" Wood Upper & Lower SHAKER CABINETS w/Soft Close Drawers, Quartz Countertops, HUGE FARM-STYLE Deep Sink, Custom Tile Backsplash, "LG" Stainless Package including a French Style Refrigerator, Flat-Top Range, Microwave, Dishwasher, Wine Refrigerator, Decorative Shelves & a Mid-Century Modern Bungalow Pendant. The Primary Suite is the perfect COUPLES RETREAT which includes a Large Bedroom, Vaulted Ceiling, and a HUGE 14' LONG WALK-IN CLOSET w/Customizable Organizers to store all your Clothes & Accessories. The Primary Bathroom includes HIS & HERS Matching Vanities with Quartz Countertops, Recessed Sinks, Dual Mirrors & Hardware. Enjoy the luxury of a custom jetted soaking tub—ideal for unwinding after a long day or for families with young children, complete with a Tile Backsplash. The "WALK-IN SHOWER" features Frameless Glass, Custom Wall & Floor Tile and an OVERHEAD RAIN SHOWER. Finally, the bathroom features oversized 24"x24" Custom Floor Tile to complete the design features. Do you ENJOY OUTDOOR SPACE & like to Entertain? Do you need a SPACIOUS KIDS AREA for them to safely play? If so, you will FALL-IN-LOVE” with the fully fenced & enclosed back yard featuring two HUGE 12'x21' and 15'x27' OPEN PAVER PATIO areas perfect for all your outdoor furniture & equipment. Also enjoy your own PRIVATE TAVERN with an 8'x12' Bar designed with Corrugated Metal Panels, a Bar Top, Shelving & Concrete Floor. The Bar is OPEN FOR YOUR FRIENDS & FAMILY. The Backyard also includes (2) Separate Gate Entrances which will accommodate & secure your Boat, Trucks, Trailers, Work Equipment, etc. In addition, there is an 8'x8' and 5'x8' Storage Rooms. Addl Features: NEW Roof (2025), NEW Interior & Exterior Paint (2025), Tankless Water heater, Carrier HVAC System (2019), Updated Electric Panel (2019), Updated PEX Plumbing (2019), Newer 8"x36" Custom Tile Flooring, Newer Double Paned Windows (2019), NEW Drain field (2024), Block Construction, HUGE Laundry & Storage Room wCustom Organizers, 6" Baseboards, Window Treatments, Ceiling Fans & Lights, Open Carport (13'x21'), Covered Carport perfect for a Golf Cart (8'x17'), Irrigation System, Gutters & Downspouts, Decorative Bamboo & much more. Just minutes to Park Avenue, Fine Dining, Leu Gardens, Downtown Orlando, Municipal & OIA Airports, Hwy 436, 408, 418, Turnpike, UCF & the Beaches. Call for more info or to schedule your private showing.

3018 Northwood Boulevard, Winter Park

$6,495,000

Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability

5 Beds ⋅ 7 Baths ⋅ Osceola Place SubDv. ⋅ 32789 Zip Code

Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability

550 Palmer Avenue, Winter Park

$1,399,500

GORGEOUS NEW CONSTRUCTION IN WINTER PARK! Discover sophisticated modern living at 607 Ellen Drive — a brand-new construction masterpiece by the acclaimed Lazarus Homes, perfectly positioned in the heart of Winter Park. At this new price, it's simply unmatched value for new construction in this location. This impeccably designed 2,812-square-foot residence showcases striking contemporary architecture with clean lines, soaring ceilings, and natural light pouring in from every angle. The open floor plan flows effortlessly from space to space, creating the ultimate backdrop for everyday living and unforgettable entertaining. The chef's kitchen is nothing short of a showstopper — outfitted with top-of-the-line Monogram appliances, a sleek Ruvati sink, built-in oven and microwave, and a professional gas range. Show-stopping Taj Mahal Quartzite countertops bring both drama and durability, and you'll have the flexibility to add a full-height wine refrigerator or extra cabinetry to make the space truly your own. The living room delivers modern warmth with an electric fireplace and walls of glass sliders that open wide to a covered lanai and your own private pool — Florida indoor-outdoor living at its absolute best. Love to entertain? The home comes pre-stubbed for an optional outdoor kitchen, ready when you are. Retreat to the luxurious first-floor primary suite, a true private sanctuary with a spa-inspired en suite bath — double sink vanity, walk-in shower, soaking tub, and an oversized walk-in closet with custom built-ins and washer/dryer hookups. Upstairs, the impressive layout continues with a spacious bonus room, a striking loft framed in glass walls, three more bedrooms, two full baths, and a second laundry area for effortless convenience. A dedicated pool bath rounds things out for easy poolside enjoyment. Tucked into the sought-after Lake Killarney Shores community, this home is the ultimate blend of peaceful retreat and unbeatable location. Enjoy a low HOA, private boat launch access to Lake Killarney, and a walkable stroll to Winter Park's best restaurants, boutiques, and cultural hotspots. New construction, lake access, unbeatable location, and a brand-new price — this move-in-ready modern luxury home won't last long!

4 Beds ⋅ 5 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code

GORGEOUS NEW CONSTRUCTION IN WINTER PARK! Discover sophisticated modern living at 607 Ellen Drive — a brand-new construction masterpiece by the acclaimed Lazarus Homes, perfectly positioned in the heart of Winter Park. At this new price, it's simply unmatched value for new construction in this location. This impeccably designed 2,812-square-foot residence showcases striking contemporary architecture with clean lines, soaring ceilings, and natural light pouring in from every angle. The open floor plan flows effortlessly from space to space, creating the ultimate backdrop for everyday living and unforgettable entertaining. The chef's kitchen is nothing short of a showstopper — outfitted with top-of-the-line Monogram appliances, a sleek Ruvati sink, built-in oven and microwave, and a professional gas range. Show-stopping Taj Mahal Quartzite countertops bring both drama and durability, and you'll have the flexibility to add a full-height wine refrigerator or extra cabinetry to make the space truly your own. The living room delivers modern warmth with an electric fireplace and walls of glass sliders that open wide to a covered lanai and your own private pool — Florida indoor-outdoor living at its absolute best. Love to entertain? The home comes pre-stubbed for an optional outdoor kitchen, ready when you are. Retreat to the luxurious first-floor primary suite, a true private sanctuary with a spa-inspired en suite bath — double sink vanity, walk-in shower, soaking tub, and an oversized walk-in closet with custom built-ins and washer/dryer hookups. Upstairs, the impressive layout continues with a spacious bonus room, a striking loft framed in glass walls, three more bedrooms, two full baths, and a second laundry area for effortless convenience. A dedicated pool bath rounds things out for easy poolside enjoyment. Tucked into the sought-after Lake Killarney Shores community, this home is the ultimate blend of peaceful retreat and unbeatable location. Enjoy a low HOA, private boat launch access to Lake Killarney, and a walkable stroll to Winter Park's best restaurants, boutiques, and cultural hotspots. New construction, lake access, unbeatable location, and a brand-new price — this move-in-ready modern luxury home won't last long!

607 Ellen Drive, Winter Park

$745,000

An incredible location close to Park Avenue, this freshly renovated home exudes modern style and the walkable lifestyle that Winter Park is known for. This timeless Florida ranch features one-level living and is in a charming downtown neighborhood that is fresh and turnkey. Experience an open living concept with seamless flooring and designer selections throughout creating great spaces and function. The kitchen features clean-lined, neutral-toned cabinetry with a large island topped with quartz counters and bar seating with gold-toned, oversized pendants that take center stage. The adjacent bar area includes a built-in pantry, open shelving and a wine refrigerator, adding a touch of luxury to your everyday life. Just beyond the kitchen/living room, you'll discover a fantastic dining area and two well-appointed bedrooms. The shared bath is fully renovated with current selections, making it a retreat for family and guests. A desirable split plan with owner's suite is on opposite side of the home, adorned with beautiful light and airiness. A space-saving built-in wardrobe lines one wall, while the en-suite bath showcases stunning design elements, including a walk-in shower, dual sinks and a private water closet. The backyard invites you out through clear glass sliders to a charming backyard with a brick patio and a fully fenced backyard, lined with bamboo, which offers the privacy you desire. Entertain with shaded dining and lounging on sunny days with newer retractable awning (2021) controlled by a convenient remote. Additional features that make this home stand out include a newer roof (2020), newer air conditioner (2020), plumbing updated 2018, electrical panel update (2023), new backyard sod and irrigation (2025), freshly painted, a two-car garage with a new electric car charger (2022), a custom workbench and storage cabinets added in 2021. And let's not forget the incredible location, a couple of blocks from Winter Park 9 Golf Course, Park Avenue, Winter Park Village and Saturday farmers market, with Whole Foods, Publix and the Enzian just minutes away, this home is your private oasis in the heart of Winter Park.

3 Beds ⋅ 2 Baths ⋅ Northwood - Winter Park Oasis SubDv. ⋅ 32789 Zip Code

An incredible location close to Park Avenue, this freshly renovated home exudes modern style and the walkable lifestyle that Winter Park is known for. This timeless Florida ranch features one-level living and is in a charming downtown neighborhood that is fresh and turnkey. Experience an open living concept with seamless flooring and designer selections throughout creating great spaces and function. The kitchen features clean-lined, neutral-toned cabinetry with a large island topped with quartz counters and bar seating with gold-toned, oversized pendants that take center stage. The adjacent bar area includes a built-in pantry, open shelving and a wine refrigerator, adding a touch of luxury to your everyday life. Just beyond the kitchen/living room, you'll discover a fantastic dining area and two well-appointed bedrooms. The shared bath is fully renovated with current selections, making it a retreat for family and guests. A desirable split plan with owner's suite is on opposite side of the home, adorned with beautiful light and airiness. A space-saving built-in wardrobe lines one wall, while the en-suite bath showcases stunning design elements, including a walk-in shower, dual sinks and a private water closet. The backyard invites you out through clear glass sliders to a charming backyard with a brick patio and a fully fenced backyard, lined with bamboo, which offers the privacy you desire. Entertain with shaded dining and lounging on sunny days with newer retractable awning (2021) controlled by a convenient remote. Additional features that make this home stand out include a newer roof (2020), newer air conditioner (2020), plumbing updated 2018, electrical panel update (2023), new backyard sod and irrigation (2025), freshly painted, a two-car garage with a new electric car charger (2022), a custom workbench and storage cabinets added in 2021. And let's not forget the incredible location, a couple of blocks from Winter Park 9 Golf Course, Park Avenue, Winter Park Village and Saturday farmers market, with Whole Foods, Publix and the Enzian just minutes away, this home is your private oasis in the heart of Winter Park.

630 Northwood Circle, Winter Park

$1,650,000

Nestled on a magnificent oversized lot in the heart of Winter Park, this 4-bedroom, 3-bath home offers plenty of space and opportunity. The backyard is a true highlight, featuring a large swimming pool and additional green space tucked just beyond the back hedges, adding a sense of privacy and flexibility for the outdoor area. Inside, the home showcases hardwood floors that flow throughout the living room, dining room, kitchen, family room, and bedrooms, creating a warm and inviting feel. A spacious family room with a cozy fireplace serves as the centerpiece of the home, while French doors open onto a vaulted screened porch, perfect for unwinding or entertaining with a view of the backyard. The kitchen offers stone countertops, and recent updates to the electrical, plumbing, and roof provide peace of mind for the next owner. This property is ideal for someone looking to renovate or update to their personal taste, or even to build a new home on this generous lot. Its location is hard to beat, set on a nice and quiet Winter Park street close to Park Avenue’s shops and dining, Rollins College, top-rated schools, and the area’s many lakes and parks. It’s a wonderful investment in both lifestyle and location.

4 Beds ⋅ 3 Baths ⋅ Stonehurst Estates SubDv. ⋅ 32789 Zip Code

Nestled on a magnificent oversized lot in the heart of Winter Park, this 4-bedroom, 3-bath home offers plenty of space and opportunity. The backyard is a true highlight, featuring a large swimming pool and additional green space tucked just beyond the back hedges, adding a sense of privacy and flexibility for the outdoor area. Inside, the home showcases hardwood floors that flow throughout the living room, dining room, kitchen, family room, and bedrooms, creating a warm and inviting feel. A spacious family room with a cozy fireplace serves as the centerpiece of the home, while French doors open onto a vaulted screened porch, perfect for unwinding or entertaining with a view of the backyard. The kitchen offers stone countertops, and recent updates to the electrical, plumbing, and roof provide peace of mind for the next owner. This property is ideal for someone looking to renovate or update to their personal taste, or even to build a new home on this generous lot. Its location is hard to beat, set on a nice and quiet Winter Park street close to Park Avenue’s shops and dining, Rollins College, top-rated schools, and the area’s many lakes and parks. It’s a wonderful investment in both lifestyle and location.

1915 Stonehurst Road, Winter Park

$1,599,900

New Construction – Carefully Curated by SGC Conctruction. Discover Modern Luxury in Winter Park's Latest Neighborhood, Winter Park Grove! Step into a world of refined living with this breathtaking new construction pool home, located in the vibrant heart of Winter Park. Just moments away from the eclectic energy of Park Avenue, this modern masterpiece seamlessly blends sophistication, style, and convenience — all within walking or biking distance of premier restaurants, cafés, boutique shops, and entertainment venues. Designed for both daily comfort and elevated entertaining, the open-concept floor plan boasts thoughtful design and high-end finishes throughout. Luxury details abound, including engineered wood floors featuring an elegant herringbone pattern in the foyer, smooth finish Level 4 drywall, and a cozy electric fireplace that enhances the spacious great room, accentuated by LED mood lighting in the coffered ceiling. The expansive gourmet kitchen is a chef’s delight, equipped with ceiling-height cabinets for ample storage and premium Thermador appliances, including a 36” gas cooktop, wall oven, built-in microwave, French door refrigerator, and a wine fridge — all complemented by sleek cabinetry and contemporary details. A beautiful dry bar adjacent to the kitchen provides extra space for coffee, wine, or entertaining guests. Offering four generous bedroom suites, this home includes a luxurious primary suite on the main level, along with a versatile second suite on the first floor, ideal for use as an office or guest retreat. Upstairs, two additional suites are connected by a flexible bonus room — perfect for a home office, gym, second living area, or even a fifth bedroom. Step outside to your private outdoor oasis, featuring a covered lanai with a fully-equipped summer kitchen (complete with grill, sink, and refrigerator drawers), and a sparkling pool adorned with travertine decking — perfect for year-round Florida entertaining. The elegant exterior showcases outdoor lighting and lush landscaping, along with a gas generator to ensure your home is always prepared for storm season.Don’t miss your opportunity to own this exquisitely crafted home in one of Orlando’s most sought-after neighborhoods. Schedule your private showing today and experience the pinnacle of luxury living in Winter Park! There are special builder incentives available right now- Call for details!!

5 Beds ⋅ 5 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code

New Construction – Carefully Curated by SGC Conctruction. Discover Modern Luxury in Winter Park's Latest Neighborhood, Winter Park Grove! Step into a world of refined living with this breathtaking new construction pool home, located in the vibrant heart of Winter Park. Just moments away from the eclectic energy of Park Avenue, this modern masterpiece seamlessly blends sophistication, style, and convenience — all within walking or biking distance of premier restaurants, cafés, boutique shops, and entertainment venues. Designed for both daily comfort and elevated entertaining, the open-concept floor plan boasts thoughtful design and high-end finishes throughout. Luxury details abound, including engineered wood floors featuring an elegant herringbone pattern in the foyer, smooth finish Level 4 drywall, and a cozy electric fireplace that enhances the spacious great room, accentuated by LED mood lighting in the coffered ceiling. The expansive gourmet kitchen is a chef’s delight, equipped with ceiling-height cabinets for ample storage and premium Thermador appliances, including a 36” gas cooktop, wall oven, built-in microwave, French door refrigerator, and a wine fridge — all complemented by sleek cabinetry and contemporary details. A beautiful dry bar adjacent to the kitchen provides extra space for coffee, wine, or entertaining guests. Offering four generous bedroom suites, this home includes a luxurious primary suite on the main level, along with a versatile second suite on the first floor, ideal for use as an office or guest retreat. Upstairs, two additional suites are connected by a flexible bonus room — perfect for a home office, gym, second living area, or even a fifth bedroom. Step outside to your private outdoor oasis, featuring a covered lanai with a fully-equipped summer kitchen (complete with grill, sink, and refrigerator drawers), and a sparkling pool adorned with travertine decking — perfect for year-round Florida entertaining. The elegant exterior showcases outdoor lighting and lush landscaping, along with a gas generator to ensure your home is always prepared for storm season.Don’t miss your opportunity to own this exquisitely crafted home in one of Orlando’s most sought-after neighborhoods. Schedule your private showing today and experience the pinnacle of luxury living in Winter Park! There are special builder incentives available right now- Call for details!!

1510 Miller Avenue, Winter Park

$8,950,000

In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

7 Beds ⋅ 11 Baths ⋅ Windsong-Preserve Point SubDv. ⋅ 32789 Zip Code

In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

1120 Preserve Point Drive, Winter Park

$2,325,000

Stunning custom residence in the highly sought-after Windsong community, built by Hal George of Parkland Homes and designed by architect Steve Feller. This one-owner home blends timeless architecture with exceptional craftsmanship and thoughtful design. From the moment you arrive, the storybook curb appeal is undeniable—brick exterior and driveway, lush landscaping, and charming gardens create a warm welcome. Inside, luxury finishes abound: herringbone wood floors, crown molding, cased openings with arched doorways, custom built-ins, and plantation shutters. The highly functional floor plan offers a downstairs owners’ suite plus a secondary bedroom (currently used as an office) with adjacent full bath. Upstairs, a spacious bonus room anchors two private bedroom suites. Soaring 10’ ceilings enhance the sense of space, with lots of natural light. The gourmet kitchen is a chef’s dream, featuring wood custom cabinetry, stainless steel appliances including a six-burner gas cooktop and Dacor double ovens, and an oversized island with sink. The kitchen flows seamlessly into the sunlit dining room with a dramatic vaulted 14’ beamed ceiling, comfortably seating 15. Set on a generous 0.38-acre lot, the outdoor living is equally impressive. The resort-style backyard showcases a covered patio with Pennsylvania Bluestone pavers, tongue-and-groove ceiling, and a charming detached garden house for storage. A serpentine wall winds gracefully through the landscaped grounds, offering privacy and charm. Additional highlights include an oversized two-car garage, indoor laundry with sink, and abundant storage throughout. A rare opportunity to own a meticulously maintained, beautifully appointed home in one of Winter Park’s most desirable communities.

4 Beds ⋅ 4 Baths ⋅ Windsong Lookout Landing 43/79 SubDv. ⋅ 32789 Zip Code

Stunning custom residence in the highly sought-after Windsong community, built by Hal George of Parkland Homes and designed by architect Steve Feller. This one-owner home blends timeless architecture with exceptional craftsmanship and thoughtful design. From the moment you arrive, the storybook curb appeal is undeniable—brick exterior and driveway, lush landscaping, and charming gardens create a warm welcome. Inside, luxury finishes abound: herringbone wood floors, crown molding, cased openings with arched doorways, custom built-ins, and plantation shutters. The highly functional floor plan offers a downstairs owners’ suite plus a secondary bedroom (currently used as an office) with adjacent full bath. Upstairs, a spacious bonus room anchors two private bedroom suites. Soaring 10’ ceilings enhance the sense of space, with lots of natural light. The gourmet kitchen is a chef’s dream, featuring wood custom cabinetry, stainless steel appliances including a six-burner gas cooktop and Dacor double ovens, and an oversized island with sink. The kitchen flows seamlessly into the sunlit dining room with a dramatic vaulted 14’ beamed ceiling, comfortably seating 15. Set on a generous 0.38-acre lot, the outdoor living is equally impressive. The resort-style backyard showcases a covered patio with Pennsylvania Bluestone pavers, tongue-and-groove ceiling, and a charming detached garden house for storage. A serpentine wall winds gracefully through the landscaped grounds, offering privacy and charm. Additional highlights include an oversized two-car garage, indoor laundry with sink, and abundant storage throughout. A rare opportunity to own a meticulously maintained, beautifully appointed home in one of Winter Park’s most desirable communities.

1268 Preserve Point Drive, Winter Park

$1,860,000

Welcome to this stunning SINGLE STORY five-bedroom home with high ceilings, in one of Winter Park’s most desirable neighborhoods, where charming restorations and luxury new builds create a vibrant community feel. Designed with both beauty and comfort in mind, this open-concept home offers bright, welcoming living spaces and thoughtful upgrades throughout. Completely rebuilt in 2014 and tons of upgrades completed in 2025. The home sits on a 1/3-acre lot with 5 bedrooms and 3 ½ baths plus an office and features a 4-way split plan with privacy for all. Upon entering, you're greeted by an open floor plan with marble foyer and white oak engineered wood flooring. The Owners' Retreat is a true sanctuary, featuring newly sanded and smoothed walls with luxe finish, automatic Hunter Douglas shades and an artful chandelier. The brand-new spa-inspired bathroom (2025) showcases the best in design and function which includes Kohler Bask heated surface tub, private toilet room with heated seat, auto lid and integrated bidet. The primary bath also has a new expanded shower, a new double sink vanity and Kohler champagne brass fixtures. The Family/Gathering space with an open chef's kitchen includes a stainless gas range, French door refrigerator, waterfall Quartzite counters and touchless kitchen and bar champagne faucets. The great room has a modern electric fireplace and leads to a screened porch and overlooks the salt water pool and large fenced backyard. Black metal remote controlled gate leads to the large 2 car detached garage with a side entry for grocery and package drop off. Home has updated cameras and security with touch screen keypad. Smart home technology Lutron lighting to schedule and control lights with mobile or Google home. Redesigned Laundry and 1/2 bath with beautiful designer wallpaper and tile and Samsung washer/dryer integrated single unit. Ideally located in one of Winter Park's coveted neighborhoods, with easy access to Park Av, Phelps Park, YMCA and Rollins College. Excellent schools, Lakemont Elem, Maitland Middle and Winter Park High. This is a rare offering of a newer one-story home, that is move in ready in the heart of Winter Park. A Must See!

5 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Welcome to this stunning SINGLE STORY five-bedroom home with high ceilings, in one of Winter Park’s most desirable neighborhoods, where charming restorations and luxury new builds create a vibrant community feel. Designed with both beauty and comfort in mind, this open-concept home offers bright, welcoming living spaces and thoughtful upgrades throughout. Completely rebuilt in 2014 and tons of upgrades completed in 2025. The home sits on a 1/3-acre lot with 5 bedrooms and 3 ½ baths plus an office and features a 4-way split plan with privacy for all. Upon entering, you're greeted by an open floor plan with marble foyer and white oak engineered wood flooring. The Owners' Retreat is a true sanctuary, featuring newly sanded and smoothed walls with luxe finish, automatic Hunter Douglas shades and an artful chandelier. The brand-new spa-inspired bathroom (2025) showcases the best in design and function which includes Kohler Bask heated surface tub, private toilet room with heated seat, auto lid and integrated bidet. The primary bath also has a new expanded shower, a new double sink vanity and Kohler champagne brass fixtures. The Family/Gathering space with an open chef's kitchen includes a stainless gas range, French door refrigerator, waterfall Quartzite counters and touchless kitchen and bar champagne faucets. The great room has a modern electric fireplace and leads to a screened porch and overlooks the salt water pool and large fenced backyard. Black metal remote controlled gate leads to the large 2 car detached garage with a side entry for grocery and package drop off. Home has updated cameras and security with touch screen keypad. Smart home technology Lutron lighting to schedule and control lights with mobile or Google home. Redesigned Laundry and 1/2 bath with beautiful designer wallpaper and tile and Samsung washer/dryer integrated single unit. Ideally located in one of Winter Park's coveted neighborhoods, with easy access to Park Av, Phelps Park, YMCA and Rollins College. Excellent schools, Lakemont Elem, Maitland Middle and Winter Park High. This is a rare offering of a newer one-story home, that is move in ready in the heart of Winter Park. A Must See!

1540 Palm Avenue, Winter Park

$1,700,000

Don’t miss the opportunity to live in one of Winter Park’s most desirable neighborhoods. Nestled on a charming, tree-lined brick street, this meticulously updated 4-bedroom, 3-bath home exudes elegance and style, offering ample space for family comfort as well as areas to relax and entertain. This impressive property has been fully renovated and is truly move-in ready. From the moment you arrive, you'll be captivated by the charming exterior and lush landscaping on a spacious .32acre lot. Inside, you'll find a bright, sophisticated home featuring beautiful hardwood floors throughout, tons of windows accented with plantation shutters, and exquisite handcrafted details. The front family room features a wood-burning fireplace, creating a comfortable space for binge-watching Netflix or Sunday NFL games, unwinding with a good book, sharing wine with friends, or hosting elegant dinner parties in the dining area. The light and bright chef’s kitchen is a culinary dream that offers a generous layout with abundant wood cabinetry, gleaming granite and gorgeous wood countertops, a large prep island with seating for four, state-of-the-art Thermador stainless steel appliances including a 6-burner professional oven, and an inviting sitting nook, capped off by a dramatic cathedral ceiling and windows that overlook the lush back yard. On one side of the home are three generously sized bedrooms with ample closet space and two full bathrooms with gorgeous custom tile and flooring. On the other side of the home awaits a true retreat: the private Primary Suite, a sanctuary equipped with a spacious bedroom, sitting area, walk-in custom closet, and a luxurious spa-inspired bath with stunning porcelain tile flooring, a large dual sink vanity, an oversized walk-in shower, and a separate water closet. Step outside to experience the quintessential Florida lifestyle in the private backyard oasis, complete with a beautiful sparkling saltwater pool, a spacious patio, and professionally landscaped grounds — ideal for entertaining year-round. Additional features include a convenient laundry/mudroom with storage for backpacks and gear, abundant closet space, a water softener, and a two-car garage with storage cabinets and shelves. Improvements include updated electrical, plumbing, and ductwork, plus a brand new tile roof (2023). This remarkable property is located close to Winter Park’s renowned Park Avenue shopping, premier restaurants, the area’s top-rated schools, and also close to Interlachen Country Club and the Winter Park Racquet Club. This exceptional property won’t last. See for yourself why this gorgeous house should be the place you call home. Schedule your showing today.

4 Beds ⋅ 3 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

Don’t miss the opportunity to live in one of Winter Park’s most desirable neighborhoods. Nestled on a charming, tree-lined brick street, this meticulously updated 4-bedroom, 3-bath home exudes elegance and style, offering ample space for family comfort as well as areas to relax and entertain. This impressive property has been fully renovated and is truly move-in ready. From the moment you arrive, you'll be captivated by the charming exterior and lush landscaping on a spacious .32acre lot. Inside, you'll find a bright, sophisticated home featuring beautiful hardwood floors throughout, tons of windows accented with plantation shutters, and exquisite handcrafted details. The front family room features a wood-burning fireplace, creating a comfortable space for binge-watching Netflix or Sunday NFL games, unwinding with a good book, sharing wine with friends, or hosting elegant dinner parties in the dining area. The light and bright chef’s kitchen is a culinary dream that offers a generous layout with abundant wood cabinetry, gleaming granite and gorgeous wood countertops, a large prep island with seating for four, state-of-the-art Thermador stainless steel appliances including a 6-burner professional oven, and an inviting sitting nook, capped off by a dramatic cathedral ceiling and windows that overlook the lush back yard. On one side of the home are three generously sized bedrooms with ample closet space and two full bathrooms with gorgeous custom tile and flooring. On the other side of the home awaits a true retreat: the private Primary Suite, a sanctuary equipped with a spacious bedroom, sitting area, walk-in custom closet, and a luxurious spa-inspired bath with stunning porcelain tile flooring, a large dual sink vanity, an oversized walk-in shower, and a separate water closet. Step outside to experience the quintessential Florida lifestyle in the private backyard oasis, complete with a beautiful sparkling saltwater pool, a spacious patio, and professionally landscaped grounds — ideal for entertaining year-round. Additional features include a convenient laundry/mudroom with storage for backpacks and gear, abundant closet space, a water softener, and a two-car garage with storage cabinets and shelves. Improvements include updated electrical, plumbing, and ductwork, plus a brand new tile roof (2023). This remarkable property is located close to Winter Park’s renowned Park Avenue shopping, premier restaurants, the area’s top-rated schools, and also close to Interlachen Country Club and the Winter Park Racquet Club. This exceptional property won’t last. See for yourself why this gorgeous house should be the place you call home. Schedule your showing today.

1571 Lasbury Avenue, Winter Park

$5,250,000

Welcome to Via Palma. This exceptional estate in the heart of the Winter Park Vias has been completely transformed, boasting over $800,000 in luxurious upgrades. A gracious entry foyer sets the tone with marble floors, custom trim work and direct views of the resort-style backyard. The first floor offers elegant formal living and dining spaces, a private study with fireplace, and a spectacular chef’s kitchen featuring an oversized marble island, custom cabinetry, Miele and Sub-Zero appliances, dual dishwashers, a built-in coffee bar, and an adjacent serving bar. The great room showcases custom built-ins, designer lighting, and seamless indoor-outdoor flow to the covered lanai, summer kitchen, lounge space, and saltwater pool. The luxurious first-floor primary suite is a serene retreat with dual dressing rooms and a lavish marble bath featuring a zero-entry double shower, freestanding soaking tub, private laundry room and designer lighting. Upstairs, additional bedrooms each feature en-suite baths and walk-in closets, complemented by a large family room, media lounge and gym with professional flooring. Every detail has been elevated, from European oak and Italian marble floors to Lutron lighting, Sonos audio, Control4 automation, Emtek smart hardware, Nest thermostats, high-efficiency HVAC systems and a backup generator. Outdoor spaces are fully reimagined with a lush landscape design, travertine decking, a putting green and privacy hedging. Near the Winter Park Racquet Club, Kraft Azalea Park, Interlachen Country Club, Phelps Park and YMCA, this home offers a rare opportunity to own a better-than-new custom estate in one of Central Florida’s desirable neighborhoods.

5 Beds ⋅ 6 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code

Welcome to Via Palma. This exceptional estate in the heart of the Winter Park Vias has been completely transformed, boasting over $800,000 in luxurious upgrades. A gracious entry foyer sets the tone with marble floors, custom trim work and direct views of the resort-style backyard. The first floor offers elegant formal living and dining spaces, a private study with fireplace, and a spectacular chef’s kitchen featuring an oversized marble island, custom cabinetry, Miele and Sub-Zero appliances, dual dishwashers, a built-in coffee bar, and an adjacent serving bar. The great room showcases custom built-ins, designer lighting, and seamless indoor-outdoor flow to the covered lanai, summer kitchen, lounge space, and saltwater pool. The luxurious first-floor primary suite is a serene retreat with dual dressing rooms and a lavish marble bath featuring a zero-entry double shower, freestanding soaking tub, private laundry room and designer lighting. Upstairs, additional bedrooms each feature en-suite baths and walk-in closets, complemented by a large family room, media lounge and gym with professional flooring. Every detail has been elevated, from European oak and Italian marble floors to Lutron lighting, Sonos audio, Control4 automation, Emtek smart hardware, Nest thermostats, high-efficiency HVAC systems and a backup generator. Outdoor spaces are fully reimagined with a lush landscape design, travertine decking, a putting green and privacy hedging. Near the Winter Park Racquet Club, Kraft Azalea Park, Interlachen Country Club, Phelps Park and YMCA, this home offers a rare opportunity to own a better-than-new custom estate in one of Central Florida’s desirable neighborhoods.

1155 Woodmere Drive, Winter Park

$5,125,000

This stunning private residence is on an oversized lot featuring a private sports pad, kids playground and sparkling pool. Encompassing over 6,700 square feet of expansive .55-acre lot, this home boast five spacious bedrooms, one office, 5.5 baths and a dedicated movie room, recording studio and a fully equipped gym with a private sauna. Ideally just moments from serene Lake Maitland and the charming Azalea Park, this home offers natural beauty and prime location. The chef's kitchen is designed for function and style with dual oversized islands, ideal for entertaining and everyday living. Spacious, inviting and thoughtfully designed, this oversized family room is the heart of the home-ideal for everything from cozy movie nights to lively holiday parties featuring expansive square footage, the room comfortably accommodates large groups, with plenty of space for multiple seating areas and a bar area. Oversized windows flood the space with natural light while the high ceilings and an open layout enhance the airy welcoming feel. Whether you are hosting extended family or entertaining friends, this room is built for connection, comfort and lasting memories. The private recording studio can be turned into a private mother-in-law suite or a kids playroom. The luxurious primary suite retreat to your own private oasis featuring a cozy fireplace, direct access to a serene private porch and a one-of-a-kind walk-in closet designed for style and functionality. The oversized en-suite bath boasts a steam shower, creating a spa-like experience right at home. Two additional en-suite bedrooms upstairs, each with walk in closets. Thoughtfully designed for convenience, this home features a spacious mud room off the garage which is ideal for busy households. Enjoy the ultimate convenience with two separate laundry rooms, one’s downstairs for easy access and a second upstairs near the bedrooms, making laundry day effortless and efficient. Ideally near Winter Park Racquet Club, Interlachen Country Club and accessible to Park Avenue, this exceptional residence also offers an extraordinary residence with a luxurious functionality and a premier location.

5 Beds ⋅ 6 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

This stunning private residence is on an oversized lot featuring a private sports pad, kids playground and sparkling pool. Encompassing over 6,700 square feet of expansive .55-acre lot, this home boast five spacious bedrooms, one office, 5.5 baths and a dedicated movie room, recording studio and a fully equipped gym with a private sauna. Ideally just moments from serene Lake Maitland and the charming Azalea Park, this home offers natural beauty and prime location. The chef's kitchen is designed for function and style with dual oversized islands, ideal for entertaining and everyday living. Spacious, inviting and thoughtfully designed, this oversized family room is the heart of the home-ideal for everything from cozy movie nights to lively holiday parties featuring expansive square footage, the room comfortably accommodates large groups, with plenty of space for multiple seating areas and a bar area. Oversized windows flood the space with natural light while the high ceilings and an open layout enhance the airy welcoming feel. Whether you are hosting extended family or entertaining friends, this room is built for connection, comfort and lasting memories. The private recording studio can be turned into a private mother-in-law suite or a kids playroom. The luxurious primary suite retreat to your own private oasis featuring a cozy fireplace, direct access to a serene private porch and a one-of-a-kind walk-in closet designed for style and functionality. The oversized en-suite bath boasts a steam shower, creating a spa-like experience right at home. Two additional en-suite bedrooms upstairs, each with walk in closets. Thoughtfully designed for convenience, this home features a spacious mud room off the garage which is ideal for busy households. Enjoy the ultimate convenience with two separate laundry rooms, one’s downstairs for easy access and a second upstairs near the bedrooms, making laundry day effortless and efficient. Ideally near Winter Park Racquet Club, Interlachen Country Club and accessible to Park Avenue, this exceptional residence also offers an extraordinary residence with a luxurious functionality and a premier location.

1240 Harding Street, Winter Park

$1,350,000

Amazing opportunity in the Forest Hills subdivision in the heart of Historic Winter Park! As you enter this charming 4 bedroom home you’re welcomed by a spacious dining room that flows seamlessly into the large family room with fireplace, custom built-in shelving and storage cupboards, crown moulding and views over the rear yard and patio, perfect for relaxing or entertaining. To the front of the home, enjoy a bright and expansive kitchen/family space featuring upgraded appliances including a Sub-Zero refrigerator and built-in coffee maker, stone countertops, and ample room for casual dining and lounging. The private primary suite includes its own bathroom, while three additional generously sized bedrooms share well-appointed bathrooms. Hardwood floors, charming details, and mature landscaping add timeless appeal. Set on a tree-lined street with a circular driveway, just minutes from Park Avenue, Rollins College, and top-rated schools, this is your chance to create your dream home in one of Winter Park’s most coveted neighborhoods!

5 Beds ⋅ 3 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Amazing opportunity in the Forest Hills subdivision in the heart of Historic Winter Park! As you enter this charming 4 bedroom home you’re welcomed by a spacious dining room that flows seamlessly into the large family room with fireplace, custom built-in shelving and storage cupboards, crown moulding and views over the rear yard and patio, perfect for relaxing or entertaining. To the front of the home, enjoy a bright and expansive kitchen/family space featuring upgraded appliances including a Sub-Zero refrigerator and built-in coffee maker, stone countertops, and ample room for casual dining and lounging. The private primary suite includes its own bathroom, while three additional generously sized bedrooms share well-appointed bathrooms. Hardwood floors, charming details, and mature landscaping add timeless appeal. Set on a tree-lined street with a circular driveway, just minutes from Park Avenue, Rollins College, and top-rated schools, this is your chance to create your dream home in one of Winter Park’s most coveted neighborhoods!

130 W Kings Way, Winter Park

$1,095,000

Located in the coveted Tree Streets just a block and a half from Lake Knowles, this timeless Mediterranean home offers three bedrooms, three and a half bathrooms, and just under 2,000 square feet of beautifully finished living space framed by mature magnolias and manicured hedges. A brick driveway leads to a two-car garage with carriage-style doors, while a covered entry showcases a solid arched wood front door with classic peep hole, setting the tone for the craftsmanship inside. Step through the entry and discover a hidden laundry room with dark wood cabinetry, marble countertops, subway tile backsplash, and front-loading washer and dryer, along with a sophisticated powder bath featuring a floating marble-topped sink, wall-mounted chrome faucet, integrated mirror lighting, and detailed molding. Just beyond is a flexible room that functions as a dining room or formal living space, and through the next doorway the home opens to a large kitchen and great room designed for everyday living and entertaining. The kitchen combines dark wood perimeter cabinetry with accent glass fronts, a creamy white island with storage on both sides, marble countertops, and stainless appliances including a GE Monogram gas cooktop with vent hood, convection oven, refrigerator, dishwasher, and LG under-counter microwave, all anchored by a deep single-barrel undermount sink with extendable faucet. The great room features a gas fireplace with mosaic tile surround, clerestory windows, extensive crown molding, and hardwood floors, with new Anderson French doors that open to the private backyard where brick decking frames a cocktail pool with water features by Signature Landscape, surrounded by mature greenery and magnolias. The primary suite, tucked on the back right wing, also enjoys French doors to the pool terrace and includes new carpet, a customized floor-to-ceiling walk-in closet, and a bath with travertine floors, sunken glass-enclosed shower with built-in shelving, creamy white vanity topped with marble, satin nickel fixtures, dual Kohler undermount sinks, and mirrored walls with crown molding. Upstairs, two spacious bedrooms each feature ensuite baths and customized closets—the front with a built-in desk, marble chicklet tile flooring, creamy cabinetry, and tub/shower combo, the second with a walk-in closet and a bath finished with travertine flooring, a slightly larger vanity with consistent cream cabinetry, marble top, and glass-enclosed shower. Additional highlights include hidden storage under the stairs, unique iron stair railing, 8’ solid wood interior doors, 10’ ceilings, and block construction, while recent updates such as an Italian tile roof (2020), newer garage door and opener, and new HVAC air handler provide peace of mind. Just a short walk to the YMCA, Phelps Park, and Interlachen Country Club, 1450 Chestnut Avenue combines Mediterranean charm, thoughtful updates, and a sought-after Winter Park location for a lock and leave lifestyle with ease.

3 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Located in the coveted Tree Streets just a block and a half from Lake Knowles, this timeless Mediterranean home offers three bedrooms, three and a half bathrooms, and just under 2,000 square feet of beautifully finished living space framed by mature magnolias and manicured hedges. A brick driveway leads to a two-car garage with carriage-style doors, while a covered entry showcases a solid arched wood front door with classic peep hole, setting the tone for the craftsmanship inside. Step through the entry and discover a hidden laundry room with dark wood cabinetry, marble countertops, subway tile backsplash, and front-loading washer and dryer, along with a sophisticated powder bath featuring a floating marble-topped sink, wall-mounted chrome faucet, integrated mirror lighting, and detailed molding. Just beyond is a flexible room that functions as a dining room or formal living space, and through the next doorway the home opens to a large kitchen and great room designed for everyday living and entertaining. The kitchen combines dark wood perimeter cabinetry with accent glass fronts, a creamy white island with storage on both sides, marble countertops, and stainless appliances including a GE Monogram gas cooktop with vent hood, convection oven, refrigerator, dishwasher, and LG under-counter microwave, all anchored by a deep single-barrel undermount sink with extendable faucet. The great room features a gas fireplace with mosaic tile surround, clerestory windows, extensive crown molding, and hardwood floors, with new Anderson French doors that open to the private backyard where brick decking frames a cocktail pool with water features by Signature Landscape, surrounded by mature greenery and magnolias. The primary suite, tucked on the back right wing, also enjoys French doors to the pool terrace and includes new carpet, a customized floor-to-ceiling walk-in closet, and a bath with travertine floors, sunken glass-enclosed shower with built-in shelving, creamy white vanity topped with marble, satin nickel fixtures, dual Kohler undermount sinks, and mirrored walls with crown molding. Upstairs, two spacious bedrooms each feature ensuite baths and customized closets—the front with a built-in desk, marble chicklet tile flooring, creamy cabinetry, and tub/shower combo, the second with a walk-in closet and a bath finished with travertine flooring, a slightly larger vanity with consistent cream cabinetry, marble top, and glass-enclosed shower. Additional highlights include hidden storage under the stairs, unique iron stair railing, 8’ solid wood interior doors, 10’ ceilings, and block construction, while recent updates such as an Italian tile roof (2020), newer garage door and opener, and new HVAC air handler provide peace of mind. Just a short walk to the YMCA, Phelps Park, and Interlachen Country Club, 1450 Chestnut Avenue combines Mediterranean charm, thoughtful updates, and a sought-after Winter Park location for a lock and leave lifestyle with ease.

1450 Chestnut Avenue, Winter Park

$1,600,000

825 Palmer Avenue, Winter Park | $1,799,000 - A Rare Venetian Canal Treasure Awaits Your Vision! Discover an extraordinary opportunity on one of Winter Park's most coveted waterways. This exceptional single-story estate on Palmer Avenue presents over 3,200 square feet of pure potential, perfectly positioned on an oversized .35-acre lot (85x173') with exclusive boathouse access to the prestigious Venetian Canal and Winter Park Chain of Lakes. Steps from the sophisticated boutiques and world-class dining of Park Avenue, this rare find offers the ultimate Winter Park lifestyle where luxury meets convenience. The thoughtfully designed open floorplan showcases expansive living spaces flooded with natural light from strategically placed skylights. Rich hardwood floors flow throughout, while French doors create seamless indoor-outdoor living. The dramatic great room captivates with distinctive brick flooring, copper-coated ceiling tiles, and an old-fashioned built-in bar—perfect for entertaining. The generously proportioned primary suite features an en suite with double sink vanity and walk-in shower. Two additional well-appointed bedrooms, each with full baths, provide comfort and privacy for the family and guests. The heart of the home centers on an expansive gourmet kitchen boasting dual sinks, premium stainless-steel appliances, solid wood cabinetry, and distinctive decorative tile countertops. A dedicated home office provides the perfect work-from-home sanctuary. Two inviting fireplaces create cozy gathering spaces throughout. The covered patio with ceiling fans extends living space outdoors, while the screened pool area offers private resort-style relaxation. The tile roof crowns this impressive estate with both beauty and durability. Whether you envision a stunning renovation showcasing the home's exceptional bones or a complete rebuild taking advantage of the prime waterfront location, this property represents a once-in-a-lifetime opportunity to create your Winter Park masterpiece.

3 Beds ⋅ 3 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

825 Palmer Avenue, Winter Park | $1,799,000 - A Rare Venetian Canal Treasure Awaits Your Vision! Discover an extraordinary opportunity on one of Winter Park's most coveted waterways. This exceptional single-story estate on Palmer Avenue presents over 3,200 square feet of pure potential, perfectly positioned on an oversized .35-acre lot (85x173') with exclusive boathouse access to the prestigious Venetian Canal and Winter Park Chain of Lakes. Steps from the sophisticated boutiques and world-class dining of Park Avenue, this rare find offers the ultimate Winter Park lifestyle where luxury meets convenience. The thoughtfully designed open floorplan showcases expansive living spaces flooded with natural light from strategically placed skylights. Rich hardwood floors flow throughout, while French doors create seamless indoor-outdoor living. The dramatic great room captivates with distinctive brick flooring, copper-coated ceiling tiles, and an old-fashioned built-in bar—perfect for entertaining. The generously proportioned primary suite features an en suite with double sink vanity and walk-in shower. Two additional well-appointed bedrooms, each with full baths, provide comfort and privacy for the family and guests. The heart of the home centers on an expansive gourmet kitchen boasting dual sinks, premium stainless-steel appliances, solid wood cabinetry, and distinctive decorative tile countertops. A dedicated home office provides the perfect work-from-home sanctuary. Two inviting fireplaces create cozy gathering spaces throughout. The covered patio with ceiling fans extends living space outdoors, while the screened pool area offers private resort-style relaxation. The tile roof crowns this impressive estate with both beauty and durability. Whether you envision a stunning renovation showcasing the home's exceptional bones or a complete rebuild taking advantage of the prime waterfront location, this property represents a once-in-a-lifetime opportunity to create your Winter Park masterpiece.

825 Palmer Avenue, Winter Park

$1,590,000

HUGE PRICE IMPROVEMENT-MOTIVATED SELLER-Discover this stunning, custom-built home nestled on a tranquil, tree-lined street just steps from all the charm of Winter Park’s renowned Park Avenue. Located in a peaceful neighborhood, this elegant residence combines sophisticated craftsmanship with luxury features throughout its expansive 2,860 square feet of thoughtfully designed living space. Relax on the charming front covered porch, the perfect spot to enjoy your morning coffee. Step inside to find meticulous attention to detail—from stunning wide white oak floors to exquisite custom millwork and soaring ceilings that create an airy, welcoming atmosphere. The chef-inspired kitchen is the heart of the home, featuring an abundance of custom solid-wood cabinets, gleaming quartz countertops, and a large island with seating for four. A generous walk-in pantry with custom shelving and top-of-the-line Thermador stainless steel appliances—including a 6-burner gas stove, double oven, and deep farm sink—make meal preparation and entertaining effortless. Adjacent to the kitchen, a charming dining area is perfect for memorable dinners, while the adjoining family room boasts a soaring cathedral ceiling, a natural gas fireplace with a custom stone mantel, and large windows that flood the space with natural light. A cozy private den offers an ideal retreat for work or relaxation. On the opposite side of the first floor, you'll find a guest suite with a private bath, two additional bedrooms with custom closets, a stylish full bath, and a laundry room with ample storage and a utility sink. The spacious mudroom, accessible from the two-car garage, provides practical storage with built-in cabinets and hooks. Upstairs, the luxurious primary suite features a spa-inspired bathroom with double sinks, custom Restoration Hardware cabinetry, elegant lighting, and a large walk-in shower. A peaceful sitting area and a walk-in closet with custom shelving create a perfect private retreat. Additionally, an upstairs loft offers versatile space ideal for a home office, gym, or additional quiet area. Outside, enjoy a private backyard oasis designed for relaxation and entertainment. Highlights include a “Michael Phelps Chilly Goat” hot/cold tub combo, outdoor TV, and speakers—creating your personal weekend paradise. Additional amenities include a large two-car garage, solid-core doors, crown molding, wide base moldings, dual tankless water heaters, fully-owned solar panels (reducing energy costs), a water softener and purifier, new exterior paint (2023), professionally installed closet shelving (2023), and professionally landscaped gardens. Flooded with natural light and warmth, this exceptional home offers a cozy yet elegant atmosphere. Zoned for top-tier schools—including Winter Park High School—and conveniently located near Lake Highland, Trinity Prep, the Winter Park YMCA, Racquet Club, and Interlachen Country Club, it’s ideal for a vibrant Florida lifestyle. Walkable to Winter Park’s renowned shopping and dining destination, don’t miss the opportunity to make this exquisite property your new home! AVAILABLE BY APPOINTMENT ONLY

4 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

HUGE PRICE IMPROVEMENT-MOTIVATED SELLER-Discover this stunning, custom-built home nestled on a tranquil, tree-lined street just steps from all the charm of Winter Park’s renowned Park Avenue. Located in a peaceful neighborhood, this elegant residence combines sophisticated craftsmanship with luxury features throughout its expansive 2,860 square feet of thoughtfully designed living space. Relax on the charming front covered porch, the perfect spot to enjoy your morning coffee. Step inside to find meticulous attention to detail—from stunning wide white oak floors to exquisite custom millwork and soaring ceilings that create an airy, welcoming atmosphere. The chef-inspired kitchen is the heart of the home, featuring an abundance of custom solid-wood cabinets, gleaming quartz countertops, and a large island with seating for four. A generous walk-in pantry with custom shelving and top-of-the-line Thermador stainless steel appliances—including a 6-burner gas stove, double oven, and deep farm sink—make meal preparation and entertaining effortless. Adjacent to the kitchen, a charming dining area is perfect for memorable dinners, while the adjoining family room boasts a soaring cathedral ceiling, a natural gas fireplace with a custom stone mantel, and large windows that flood the space with natural light. A cozy private den offers an ideal retreat for work or relaxation. On the opposite side of the first floor, you'll find a guest suite with a private bath, two additional bedrooms with custom closets, a stylish full bath, and a laundry room with ample storage and a utility sink. The spacious mudroom, accessible from the two-car garage, provides practical storage with built-in cabinets and hooks. Upstairs, the luxurious primary suite features a spa-inspired bathroom with double sinks, custom Restoration Hardware cabinetry, elegant lighting, and a large walk-in shower. A peaceful sitting area and a walk-in closet with custom shelving create a perfect private retreat. Additionally, an upstairs loft offers versatile space ideal for a home office, gym, or additional quiet area. Outside, enjoy a private backyard oasis designed for relaxation and entertainment. Highlights include a “Michael Phelps Chilly Goat” hot/cold tub combo, outdoor TV, and speakers—creating your personal weekend paradise. Additional amenities include a large two-car garage, solid-core doors, crown molding, wide base moldings, dual tankless water heaters, fully-owned solar panels (reducing energy costs), a water softener and purifier, new exterior paint (2023), professionally installed closet shelving (2023), and professionally landscaped gardens. Flooded with natural light and warmth, this exceptional home offers a cozy yet elegant atmosphere. Zoned for top-tier schools—including Winter Park High School—and conveniently located near Lake Highland, Trinity Prep, the Winter Park YMCA, Racquet Club, and Interlachen Country Club, it’s ideal for a vibrant Florida lifestyle. Walkable to Winter Park’s renowned shopping and dining destination, don’t miss the opportunity to make this exquisite property your new home! AVAILABLE BY APPOINTMENT ONLY

1166 Oaks Boulevard, Winter Park

$2,144,000

Wonderful home in sought-after Pennsylvania Place. Newer roof (2019), HVAC and Water Heaters

4 Beds ⋅ 4 Baths ⋅ Pennsylvania Place SubDv. ⋅ 32789 Zip Code

Wonderful home in sought-after Pennsylvania Place. Newer roof (2019), HVAC and Water Heaters

1077 N. Pennsylvania Ave, Winter Park

$3,965,000

Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Meticulously maintained with great inspection. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an additional powder room. A 412-square-foot casita with a wet bar and private entrance completes its functionality by providing extra flexibility, perfect for guests, extended family, workspace or workout area. The interiors showcase timeless design with high ceilings, glass walls, and carefully curated finishes. The chef’s kitchen and butler’s pantry pair handcrafted cabinetry and stone surfaces with professional-grade appliances, flowing seamlessly into open living and dining spaces designed for both everyday living and entertaining. Outdoors, a 65-foot lap pool anchors the private backyard retreat, complemented by a covered lanai, marine-grade summer kitchen, fireplace lounge, tree garden and lush landscaping. Solid block construction, advanced state-of-the-art home systems, and a climate-controlled two-car garage with an extended hidden driveway highlight the home’s privacy, quality, and convenience. With a distinct European vibe under canopy trees and cobblestone streets in the desirable Valencia Terrace neighborhood, this home is just moments from Park Avenue’s boutiques, fine dining, Rollins College, the Farmers’ Market, and the Morse Museum. Zoned for top-rated Winter Park schools, it offers both luxury and practicality in one of Central Florida’s most sought-after communities.

4 Beds ⋅ 5 Baths ⋅ Valencia Terrace SubDv. ⋅ 32789 Zip Code

Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Meticulously maintained with great inspection. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an additional powder room. A 412-square-foot casita with a wet bar and private entrance completes its functionality by providing extra flexibility, perfect for guests, extended family, workspace or workout area. The interiors showcase timeless design with high ceilings, glass walls, and carefully curated finishes. The chef’s kitchen and butler’s pantry pair handcrafted cabinetry and stone surfaces with professional-grade appliances, flowing seamlessly into open living and dining spaces designed for both everyday living and entertaining. Outdoors, a 65-foot lap pool anchors the private backyard retreat, complemented by a covered lanai, marine-grade summer kitchen, fireplace lounge, tree garden and lush landscaping. Solid block construction, advanced state-of-the-art home systems, and a climate-controlled two-car garage with an extended hidden driveway highlight the home’s privacy, quality, and convenience. With a distinct European vibe under canopy trees and cobblestone streets in the desirable Valencia Terrace neighborhood, this home is just moments from Park Avenue’s boutiques, fine dining, Rollins College, the Farmers’ Market, and the Morse Museum. Zoned for top-rated Winter Park schools, it offers both luxury and practicality in one of Central Florida’s most sought-after communities.

1161 Valencia Avenue, Winter Park

$2,700,000

Experience Mediterranean charm in this fabulous five-bedroom, five-bath pool home built by Cahill Builders. On the north side of Windsong, this home features an open floor plan with spacious living areas that flow seamlessly and provide warm natural light. The living room with cozy gas fireplace overlooks the spacious and open dining room while the light-filled family room with French doors has wonderful views of the covered lanai and pool. You will love entertaining in the chef’s eat-in kitchen with many updates and upgrades completed in 2024. Kitchen features include stainless appliances, natural gas cooktop, double ovens, large center prep island and large walk-in pantry. The first-floor luxurious owner’s retreat features vaulted and hand-crafted wood beam ceilings, wide plank wood floors and bath with dual vanities, walk-in shower and spa tub. Bedroom Suite 2, which is also on the main level is ideal for guests, home office or nursery. As you go upstairs, the second floor offers a thoughtfully designed retreat for both relaxation and entertainment. There are three spacious bedrooms each with their private baths. This layout offers comfort and privacy for family or guests. The media room provides the ideal setting for movie nights or immersive gaming and includes an additional room for a playroom, library or large air-conditioned storage space. Whether you are entertaining or unwinding, this upper-level layout delivers functionality and privacy. Go outside to enjoy the covered lanai which overlooks the private and expansive yard filled with a vibrant mix of citrus trees, tropical plants and year-round flowering garden. The fabulous landscape was designed by a landscape architect with the concept to provide continuous blooms and inviting sitting areas under the sun. The sparkling pool and spa, large surrounding patio and firepit area invite year-round enjoyment. Additional amenities include custom molding and trim work, an entry fountain and three-car garage (one with split air conditioning). Windsong, one of Winter Park's sought-after neighborhoods, offers exclusive amenities to their residents including a pontoon boat to enjoy Winter Park Chain of Lakes, two community pools, a splash park, playground, a lakefront clubhouse and a scenic pier for fishing. Ideal location is minutes from hospitals, schools, golf courses, and Park Avenue’s amazing dining and shopping.

5 Beds ⋅ 5 Baths ⋅ Windsong Lakeside SubDv. ⋅ 32789 Zip Code

Experience Mediterranean charm in this fabulous five-bedroom, five-bath pool home built by Cahill Builders. On the north side of Windsong, this home features an open floor plan with spacious living areas that flow seamlessly and provide warm natural light. The living room with cozy gas fireplace overlooks the spacious and open dining room while the light-filled family room with French doors has wonderful views of the covered lanai and pool. You will love entertaining in the chef’s eat-in kitchen with many updates and upgrades completed in 2024. Kitchen features include stainless appliances, natural gas cooktop, double ovens, large center prep island and large walk-in pantry. The first-floor luxurious owner’s retreat features vaulted and hand-crafted wood beam ceilings, wide plank wood floors and bath with dual vanities, walk-in shower and spa tub. Bedroom Suite 2, which is also on the main level is ideal for guests, home office or nursery. As you go upstairs, the second floor offers a thoughtfully designed retreat for both relaxation and entertainment. There are three spacious bedrooms each with their private baths. This layout offers comfort and privacy for family or guests. The media room provides the ideal setting for movie nights or immersive gaming and includes an additional room for a playroom, library or large air-conditioned storage space. Whether you are entertaining or unwinding, this upper-level layout delivers functionality and privacy. Go outside to enjoy the covered lanai which overlooks the private and expansive yard filled with a vibrant mix of citrus trees, tropical plants and year-round flowering garden. The fabulous landscape was designed by a landscape architect with the concept to provide continuous blooms and inviting sitting areas under the sun. The sparkling pool and spa, large surrounding patio and firepit area invite year-round enjoyment. Additional amenities include custom molding and trim work, an entry fountain and three-car garage (one with split air conditioning). Windsong, one of Winter Park's sought-after neighborhoods, offers exclusive amenities to their residents including a pontoon boat to enjoy Winter Park Chain of Lakes, two community pools, a splash park, playground, a lakefront clubhouse and a scenic pier for fishing. Ideal location is minutes from hospitals, schools, golf courses, and Park Avenue’s amazing dining and shopping.

1445 Holts Grove, Winter Park

$2,798,000

Stunning canal-front home, Winter Park Chain of Lakes. Welcome to this exceptional one-story residence in the heart of Winter Park, offering direct access to the desired Winter Park Chain of Lakes via the Venetian Canal. Built in 2018, this meticulously maintained home features four bedrooms, three baths, and 3,258 square feet of elegant living space designed for comfort and entertaining. The open floor plan showcases a large gourmet kitchen outfitted with custom cabinetry and generous counter space. Ideal for hosting gatherings or enjoying quiet evenings at home. Expansive windows throughout the home offer beautiful, tranquil views of the canal and lush, mature landscaping. Large screened-in lanai complete with a fully equipped summer kitchen and fireplace overlooking the canal and private boathouse.

4 Beds ⋅ 3 Baths ⋅ Palmer Park SubDv. ⋅ 32789 Zip Code

Stunning canal-front home, Winter Park Chain of Lakes. Welcome to this exceptional one-story residence in the heart of Winter Park, offering direct access to the desired Winter Park Chain of Lakes via the Venetian Canal. Built in 2018, this meticulously maintained home features four bedrooms, three baths, and 3,258 square feet of elegant living space designed for comfort and entertaining. The open floor plan showcases a large gourmet kitchen outfitted with custom cabinetry and generous counter space. Ideal for hosting gatherings or enjoying quiet evenings at home. Expansive windows throughout the home offer beautiful, tranquil views of the canal and lush, mature landscaping. Large screened-in lanai complete with a fully equipped summer kitchen and fireplace overlooking the canal and private boathouse.

1074 Mckean Circle, Winter Park

$1,640,000

One or more photo(s) has been virtually staged. This signature corner unit in the exclusive Douglas Grand, is perched on the top two floors, with panoramic views of downtown Winter Park, Hannibal’s Square and Rollins College all steps away. This spacious luxury unit includes a three-bedroom split plan and three-and-a-half en-suite baths, with two private balconies from bedrooms overlooking Central Park. Every convenience of the desirable Winter Park lifestyle is at your doorstep. A gated parking garage provides security for you and your guests. Step inside to discover the 3,174-square-foot perfectly renovated residence with gorgeous new blonde wood floors throughout the living room and bedrooms, and surrounded by windows that invite beautiful light in. Entertain with ease in the expansive gourmet kitchen, recently renovated with added cabinetry including a pantry, new quartz counters, custom back splash and top-of-the-line appliances. Bar seating at the counter peninsula still leaves room for an additional dine-in table if you desire. What makes this unit unique is the open-air two-story center atrium that connects all the living spaces together and adds secluded outdoor living for privacy with views to the stars. The primary bedroom enjoys treetop views, private balcony just recently tiled and generous space and closet. The primary bath suite includes updated dual vanities, separate shower and an indulgent jetted tub. Secondary bedrooms are private with one upstairs and the third bedroom suite, or office, offers versatility and function. Elevate your lifestyle with a host of modern amenities, including updated designer fixtures, recessed lighting and fans, some new Pella doors and windows, fresh paint, spacious walk-in closets that provide ample storage in every bedroom and a freshly painted interior and private laundry. Enjoy the added convenience of two deeded parking spaces in the gated-attached garage, with direct access to your floor and access door right next to your front door, so convenient. Every aspect of luxury living has been meticulously curated for your enjoyment. Indulge in the unparalleled convenience of strolling to nearby restaurants, coffee shops and boutiques. Rollins College is nearby, as well as fabulous events in Central Park and the bustling farmers market. Don’t miss your chance to experience the pinnacle of urban sophistication at The Douglas Grand.

3 Beds ⋅ 4 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. This signature corner unit in the exclusive Douglas Grand, is perched on the top two floors, with panoramic views of downtown Winter Park, Hannibal’s Square and Rollins College all steps away. This spacious luxury unit includes a three-bedroom split plan and three-and-a-half en-suite baths, with two private balconies from bedrooms overlooking Central Park. Every convenience of the desirable Winter Park lifestyle is at your doorstep. A gated parking garage provides security for you and your guests. Step inside to discover the 3,174-square-foot perfectly renovated residence with gorgeous new blonde wood floors throughout the living room and bedrooms, and surrounded by windows that invite beautiful light in. Entertain with ease in the expansive gourmet kitchen, recently renovated with added cabinetry including a pantry, new quartz counters, custom back splash and top-of-the-line appliances. Bar seating at the counter peninsula still leaves room for an additional dine-in table if you desire. What makes this unit unique is the open-air two-story center atrium that connects all the living spaces together and adds secluded outdoor living for privacy with views to the stars. The primary bedroom enjoys treetop views, private balcony just recently tiled and generous space and closet. The primary bath suite includes updated dual vanities, separate shower and an indulgent jetted tub. Secondary bedrooms are private with one upstairs and the third bedroom suite, or office, offers versatility and function. Elevate your lifestyle with a host of modern amenities, including updated designer fixtures, recessed lighting and fans, some new Pella doors and windows, fresh paint, spacious walk-in closets that provide ample storage in every bedroom and a freshly painted interior and private laundry. Enjoy the added convenience of two deeded parking spaces in the gated-attached garage, with direct access to your floor and access door right next to your front door, so convenient. Every aspect of luxury living has been meticulously curated for your enjoyment. Indulge in the unparalleled convenience of strolling to nearby restaurants, coffee shops and boutiques. Rollins College is nearby, as well as fabulous events in Central Park and the bustling farmers market. Don’t miss your chance to experience the pinnacle of urban sophistication at The Douglas Grand.

101 S New York Avenue Unit 313, Winter Park

$1,875,000

Timeless Elegance Meets Modern Comfort in Sought-After Tree Streets Welcome to this thoughtfully designed, custom-built residence in the coveted Tree Streets community of Winter Park. Boasting 4 bedrooms, 4.5 bathrooms, and over 3,300 square feet of meticulously curated living space, this one-of-a-kind home perfectly blends craftsmanship, comfort, and style. At the heart of the home, the chef-inspired kitchen showcases premium Thermador appliances, a gas range, and custom cabinetry that soars to 10-foot ceilings. The spacious butler’s pantry and built-in breakfast nook flow seamlessly into an inviting great room with custom built-ins—ideal for both everyday living and elegant entertaining. Nearby, the formal dining room features a striking drop ceiling, setting the stage for unforgettable gatherings. Designed for everyday convenience and privacy, the first floor includes both a comfortable guest suite and a luxurious primary suite, which features elegant wood beams accenting the ceiling and creates a warm, sophisticated retreat. Throughout the home, beautiful white oak floors add warmth and character, complementing the timeless design and enhancing the flow between each thoughtfully crafted space. Enjoy effortless indoor-outdoor living with an expansive covered lanai featuring a built-in summer kitchen and phantom screens, all overlooking a stunning pool and spa embraced by lush landscaping. A dedicated pool bath ensures convenience for guests enjoying the outdoor oasis. Inside, thoughtful features abound: a stylish mudroom with built-in storage, a large utility room with cabinetry and sink, and a conditioned mechanical room offering smart storage solutions. Upstairs, discover a spacious loft perfect for a media room or play area, accompanied by two generously sized bedrooms each with ensuite baths and ample closets. The Stratford-style front porch invites neighborly chats, while the private backyard provides a serene retreat. Designer-selected finishes and custom touches are evident throughout, highlighting the home's timeless elegance and modern functionality. Ideally situated just minutes from Park Avenue, residents will enjoy effortless access to fine dining, boutique shopping, charming cafes, museums, and the vibrant cultural heart of Winter Park. A rare offering that combines luxurious design, exceptional craftsmanship, and the warm character only a custom-built home can provide—this residence truly stands out in the Tree Streets.

4 Beds ⋅ 5 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Timeless Elegance Meets Modern Comfort in Sought-After Tree Streets Welcome to this thoughtfully designed, custom-built residence in the coveted Tree Streets community of Winter Park. Boasting 4 bedrooms, 4.5 bathrooms, and over 3,300 square feet of meticulously curated living space, this one-of-a-kind home perfectly blends craftsmanship, comfort, and style. At the heart of the home, the chef-inspired kitchen showcases premium Thermador appliances, a gas range, and custom cabinetry that soars to 10-foot ceilings. The spacious butler’s pantry and built-in breakfast nook flow seamlessly into an inviting great room with custom built-ins—ideal for both everyday living and elegant entertaining. Nearby, the formal dining room features a striking drop ceiling, setting the stage for unforgettable gatherings. Designed for everyday convenience and privacy, the first floor includes both a comfortable guest suite and a luxurious primary suite, which features elegant wood beams accenting the ceiling and creates a warm, sophisticated retreat. Throughout the home, beautiful white oak floors add warmth and character, complementing the timeless design and enhancing the flow between each thoughtfully crafted space. Enjoy effortless indoor-outdoor living with an expansive covered lanai featuring a built-in summer kitchen and phantom screens, all overlooking a stunning pool and spa embraced by lush landscaping. A dedicated pool bath ensures convenience for guests enjoying the outdoor oasis. Inside, thoughtful features abound: a stylish mudroom with built-in storage, a large utility room with cabinetry and sink, and a conditioned mechanical room offering smart storage solutions. Upstairs, discover a spacious loft perfect for a media room or play area, accompanied by two generously sized bedrooms each with ensuite baths and ample closets. The Stratford-style front porch invites neighborly chats, while the private backyard provides a serene retreat. Designer-selected finishes and custom touches are evident throughout, highlighting the home's timeless elegance and modern functionality. Ideally situated just minutes from Park Avenue, residents will enjoy effortless access to fine dining, boutique shopping, charming cafes, museums, and the vibrant cultural heart of Winter Park. A rare offering that combines luxurious design, exceptional craftsmanship, and the warm character only a custom-built home can provide—this residence truly stands out in the Tree Streets.

1752 Chestnut Avenue, Winter Park

$4,500,000

Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1-acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park living—all within walking distance to Park Avenue. This stately 6-bedroom, 5.5-bathroom home offers 5,759 square feet of thoughtfully designed living space, plus an additional 1,859-square-foot unfinished basement that spans the entire length of the home, offering endless possibilities for expansion or customization. Upon entry, you'll be welcomed by coffered ceilings in the spacious formal living room, rich dark oak floors, and one of the home’s three gas fireplaces. This elegant yet inviting room overlooks the lush gardens, making it an ideal setting for both entertaining and quiet relaxation. Adjacent to the living room is a cozy, beautifully appointed den featuring another gas fireplace and natural jute flooring—undoubtedly one of the most beloved spaces in the home. The kitchen is filled with natural light and includes a large casual dining area, a charming butler’s pantry, and direct access to both the laundry room—complete with a full-size refrigerator and half-bath—and the oversized 2-car garage. The formal dining room showcases lattice-framed bay windows with views of the back garden and pool area, creating a warm and elegant space perfect for holiday dinners and family gatherings. The home features two primary bedroom suites on the main level, including one expansive L-shaped suite with its own gas fireplace and views of the pool, gardens, and outdoor terrace. The primary bathroom includes a dressing area and marble finishes throughout. Upstairs, the south wing includes two generous bedrooms with a shared full bathroom, while the north wing—located above the kitchen—offers two additional bedrooms and a charming full bath. The expansive backyard is a private sanctuary, framed by majestic oak trees, bamboo, and thoughtfully designed gardens, with several inviting sitting areas for outdoor relaxation. An extra-large swimming pool completes the setting—perfect for warm Florida days or evening gatherings under the stars.

6 Beds ⋅ 6 Baths ⋅ Dyer Susan Resub SubDv. ⋅ 32789 Zip Code

Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1-acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park living—all within walking distance to Park Avenue. This stately 6-bedroom, 5.5-bathroom home offers 5,759 square feet of thoughtfully designed living space, plus an additional 1,859-square-foot unfinished basement that spans the entire length of the home, offering endless possibilities for expansion or customization. Upon entry, you'll be welcomed by coffered ceilings in the spacious formal living room, rich dark oak floors, and one of the home’s three gas fireplaces. This elegant yet inviting room overlooks the lush gardens, making it an ideal setting for both entertaining and quiet relaxation. Adjacent to the living room is a cozy, beautifully appointed den featuring another gas fireplace and natural jute flooring—undoubtedly one of the most beloved spaces in the home. The kitchen is filled with natural light and includes a large casual dining area, a charming butler’s pantry, and direct access to both the laundry room—complete with a full-size refrigerator and half-bath—and the oversized 2-car garage. The formal dining room showcases lattice-framed bay windows with views of the back garden and pool area, creating a warm and elegant space perfect for holiday dinners and family gatherings. The home features two primary bedroom suites on the main level, including one expansive L-shaped suite with its own gas fireplace and views of the pool, gardens, and outdoor terrace. The primary bathroom includes a dressing area and marble finishes throughout. Upstairs, the south wing includes two generous bedrooms with a shared full bathroom, while the north wing—located above the kitchen—offers two additional bedrooms and a charming full bath. The expansive backyard is a private sanctuary, framed by majestic oak trees, bamboo, and thoughtfully designed gardens, with several inviting sitting areas for outdoor relaxation. An extra-large swimming pool completes the setting—perfect for warm Florida days or evening gatherings under the stars.

887 Georgia Avenue, Winter Park

$630,000

RENOVATED and MOVE-IN READY in WINTER PARK 32789 with DEEDED LAKE ACCESS! Located on a fully fenced ¼-acre corner lot, this 4-bed, 3-bath charmer offers private access to Lake Killarney, a rare find. Step onto the welcoming front porch and into a home filled with character, upgrades, and natural light. The open layout flows effortlessly through spacious living areas and a beautifully updated kitchen with modern finishes. Wood-look flooring, custom millwork, neutral tones, and designer lighting elevate the space. Enjoy a SPLIT FLOOR PLAN with 4 spacious bedrooms, including a large primary suite and a guest room with its own ensuite. The screened lanai and private backyard create the perfect outdoor retreat. Extras include a fireplace, two car attached garage and no HOA! This is a dream location just 1 mile to Trader Joe’s, 1.5 miles to Park Avenue, and minutes to I-4, Rollins College, shopping, dining, and more. Don’t miss your chance to live in the heart of Winter Park. Schedule your private tour today!

4 Beds ⋅ 3 Baths ⋅ Flamingo Shores SubDv. ⋅ 32789 Zip Code

RENOVATED and MOVE-IN READY in WINTER PARK 32789 with DEEDED LAKE ACCESS! Located on a fully fenced ¼-acre corner lot, this 4-bed, 3-bath charmer offers private access to Lake Killarney, a rare find. Step onto the welcoming front porch and into a home filled with character, upgrades, and natural light. The open layout flows effortlessly through spacious living areas and a beautifully updated kitchen with modern finishes. Wood-look flooring, custom millwork, neutral tones, and designer lighting elevate the space. Enjoy a SPLIT FLOOR PLAN with 4 spacious bedrooms, including a large primary suite and a guest room with its own ensuite. The screened lanai and private backyard create the perfect outdoor retreat. Extras include a fireplace, two car attached garage and no HOA! This is a dream location just 1 mile to Trader Joe’s, 1.5 miles to Park Avenue, and minutes to I-4, Rollins College, shopping, dining, and more. Don’t miss your chance to live in the heart of Winter Park. Schedule your private tour today!

1792 Killarney Drive, Winter Park