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$5,400,000
5 Beds ⋅ 9 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code
Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly into a private courtyard with a heated pool and spa, covered dining, an outdoor grill, a wood-burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two-story wardrobe with an office in one of the primary closets, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and a trash compactor. For large-scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall-to-wall storage. Built by renowned builder Charles Clayton and designed by Marc-Michaels, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenue’s world-class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. A rare opportunity to acquire a legacy property with major aesthetic updates already completed and future equity positioned for growth.

1400 Alabama Drive, Winter Park
$535,000
4 Beds ⋅ 2 Baths ⋅ Orwin Manor Stratford Sec SubDv. ⋅ 32789 Zip Code
Welcome to your dream home nestled in the highly sought-after College Park district of Winter Park! This charming residence seamlessly blends history with modern upgrades, offering a perfect balance of comfort and convenience. Step inside to discover a beautifully updated kitchen featuring elegant granite countertops, ideal for both casual meals and entertaining guests. The home now boasts 1,795 heated square feet, thanks to a thoughtful garage conversion. The previous owner transformed the garage into a spacious primary bedroom with an en-suite bath, complete with central air conditioning and an additional mini-split AC unit for added comfort. The home also features an electronic gate access carport, ensuring secure and easy parking, while the expansive, fully fenced backyard provides a private oasis for relaxation or gatherings. Imagine enjoying your morning coffee or hosting weekend barbecues in this serene outdoor space. Location is everything, and this home delivers! Just a stone's throw away from Trader Joe's, you'll have easy access to popular shopping and dining options. Plus, with its proximity to downtown Orlando and local attractions, you'll never be far from the vibrant lifestyle that this area offers. Don't miss the opportunity to own a piece of history with all the modern comforts you desire. Schedule your showing today and experience the charm and convenience of this exceptional College Park home!

1531 Norfolk Avenue, Winter Park
$1,400,000
4 Beds ⋅ 4 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code
Welcome to this masterfully renovated Winter Park residence, where modern luxury meets timeless comfort in coveted Timberlane Shores. The heart of this home is a chef's dream kitchen, featuring a professional WOLF range, custom two-tone cabinetry in rich wood and sophisticated navy blue, and premium stone countertops that extend to a generous entertainment island. Gleaming terrazzo floors flow seamlessly through the open-concept living spaces, where abundant windows frame views of the lush gardens and flood the home with natural light. The thoughtfully designed floor plan incorporates two distinct living areas - one integrated with the kitchen for casual gatherings, and a separate space with soaring vaulted ceilings and custom built-ins perfect for formal entertaining or quiet evenings. The primary retreat offers a private sanctuary with vaulted ceilings, spa-like ensuite bath, and walk-in closet, while three additional bedroom suites provide comfortable accommodations for family or guests. Step outside to discover multiple outdoor living spaces, including a patio ideal for al fresco dining and a spacious backyard with mature landscaping and room for a future pool. Located in one of Orlando's most sought after neighborhoods, this turnkey home offers access to top-rated schools including Audubon K-8 and Winter Park High School. This is more than a house - it's an invitation to experience the refined Winter Park lifestyle you've been dreaming of.

1750 Winchester Drive, Winter Park
$649,000
3 Beds ⋅ 2 Baths ⋅ Lake Virginia Shores SubDv. ⋅ 32789 Zip Code
Charming pool home zoned for Audubon K-8 and Winter Park High, tucked behind a private courtyard with artificial turf that feels like your own little secret garden. Vaulted ceilings with tongue-and-groove details add warmth and character to the living and dining areas. The eat-in kitchen features a large passthrough window overlooking the great room, perfect for entertaining. The bright Florida room brings in natural light and opens to the screened-in patio and pool—ready for relaxing weekends. The primary suite offers sliding glass doors to the patio, a walk-in closet, and an en-suite bathroom. Two additional bedrooms share a hall bath with an updated vanity and a shower/tub combo. Outside, the screened patio and pool create a private oasis, with a low-maintenance yard offering potential for customization. Additional features include a two-car garage, plantation shutters throughout, 2021 roof, 2018 AC, and whole-house re-plumbed in 2004. Conveniently located minutes from Park Avenue, Baldwin Park, and Winter Park's dining and shopping scene. Call today to schedule your private showing!

721 Glenridge Way, Winter Park
$1,265,000
3 Beds ⋅ 4 Baths ⋅ Sylvan Park SubDv. ⋅ 32789 Zip Code
Data entry only.

420 Sylvan Drive, Winter Park
$1,395,000
4 Beds ⋅ 4 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code
Welcome to your new home in Timberlane Shores. This one-story ranch offers a delightful living experience. The generously sized master suite features a spacious bath and walk-in closet. The split floor plan ensures privacy, with three well-appointed rooms on the opposite side of the house. Wood floors throughout, granite counters in the kitchen and bathrooms. Kitchen features soft touch cabinets and stainless-steel appliances. Step outside and immerse yourself in the serene surroundings, with an expansive front and back yard adorned with well-kept lawns. The backyard oasis features a refreshing pool, offering a private escape. This home is perfect for entertaining, making it an ideal space for hosting gatherings with friends. Located in a sought-after school district, this neighborhood offers an exceptional educational environment.

1771 Winchester Drive, Winter Park
$586,500
3 Beds ⋅ 1 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code
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2361 Mulbry Drive, Winter Park
$4,273,211
4 Beds ⋅ 5 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code
Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in main house plus detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform TWELVE kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry, and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here, with a sculptural installation of galvanized steel surrounding a crepe myrtle, accompanied by a matching bike rack. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool and spa, while a custom cedar hot tub blends into the landscape. A wood-clad pergola shelters the outdoor kitchen, featuring a Röshults system with a professional-grade grill, sink and storage. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

1336 College Point, Winter Park
$799,000
3 Beds ⋅ 3 Baths ⋅ Temple Estates SubDv. ⋅ 32789 Zip Code
A pristine location to build the home of your dreams in the heart of the Tree Streets of Winter Park. Elm is a quiet tree-lined street providing tranquility while providing the lifestyle Winter Park is known for. Elm is a block from Phelps Park, a short walk to YMCA, Interlachen Country Club and Winter Park Racquet Club. The lot is roughly 75 by 122 feet and among multimillion-dollar homes. Home to the best schools, zoned for Lakemont, Maitland Middle and Winter Park High. Homes on this street don’t come up often. Call us for a private showing.

Winter Park
$610,000
3 Beds ⋅ 2 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code
Welcome to 2812 Mulford Avenue. This updated 3 bedroom and 2 bath home is located perfectly in Winter Park. Walking distance to East End Market, close to Rollins College, steps from Baldwin Park, 1 mile from Mills 50 area, and close to Mead Gardens, Leu Gardens and Loch Haven Park. The neighborhood is quiet with low traffic, oversized lots, and NO HOA, yet surrounded by amazing schools, local coffee shops, incredible restaurants & bars, and world-class shopping. The home itself is completely move-in ready, offering an amazing kitchen and is open to the formal living room/dining room. This open space connects to the den, which is an oversized room that leads to the expansive backyard with a great patio deck for entertaining, and convenient storage shed. The living room also connects via french doors to a great flex space that could morph into a homework station, home office, or new laundry room. Welcome Home!

2812 Mulford Avenue, Winter Park
$1,835,000
4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
A timeless masterpiece, this 1935 English Cottage, designed by the renowned Gamble Rogers, stands as a testament to classic elegance and enduring craftsmanship. Nestled on nearly half an acre in one of Winter Park’s most coveted neighborhoods, this home has been thoughtfully updated with modern luxuries while preserving its original charm. Inside, warm Heart of Pine floors, beadboard vaulted ceilings, restored period hardware, and custom built-ins create an inviting ambiance. Spacious formal and casual living areas include a dining room, separate living and family rooms, an office, and a versatile flex space. The expanded and renovated kitchen is a chef’s dream, now featuring marble countertops, custom white cabinetry, a Wolf gas range, stainless steel appliances, a built-in Miele espresso machine, and a farmhouse sink. The thoughtful redesign includes a custom range hood, a new ventilation system, and an integrated refrigerator/freezer drawer in the island. The first-floor primary suite is a private retreat with serene backyard views, two walk-in closets, and a bathroom with dual vanities, a clawfoot tub, and a separate shower. Upstairs, two bedrooms share a charming bathroom. Outside, a lushly landscaped backyard offers an idyllic escape with a newly installed pool heater (2023), a restored koi pond, and extensive hardscape additions. A covered porch and a newly added summer kitchen with plumbing make this home an entertainer’s paradise. The fully fenced property is surrounded by mature landscaping, refreshed with new perennials and heirloom camellias. Additional recent upgrades include a new roof (2021), restored siding, new gutters with leaf guards, and a new irrigation system. A detached guest house with a sitting area and loft provides the perfect private space for visitors. Located just minutes from Park Avenue, downtown Orlando, and zoned for the sought-after Audubon Park K-8 and Winter Park High School, this home embodies the perfect blend of historic elegance and modern convenience.

160 Glenridge Way, Winter Park
$2,250,000
4 Beds ⋅ 6 Baths ⋅ Shores Lake Killarney Sec 02 SubDv. ⋅ 32789 Zip Code
Nestled along the serene shores of Lake Killarney, one of Winter Park's best-kept secrets Lake Killarney is one of Winter Park's largest freshwater spring-fed lakes (240 acres) this stunning lakefront home offers breathtaking views and direct water access. Featuring a private boat lift, dock, and spacious outdoor entertaining areas, this property is perfect for boating enthusiasts and nature lovers alike, including boat, canoe, kayak, ski, fish, windsurf or jet ski on this pristine lake. Come early for your appointment and drive the entire quaint neighborhood and see why this neighborhood for lakefront living is so sought after. Where else can you boat and dock at Trader Joe's, Hillstone's Restaurant, some of Winter Park's most desirable shopping and restaurant establishments? The home is located just minutes from Park Ave., I-4, Rollins College, Winter Park Village, Winter Park's Ravaudage and ALL OF Winter Park's restaurants and shopping!! Inside, you’ll find an open-concept layout with high ceilings, large windows, and modern finishes. The gourmet kitchen boasts stainless steel appliances, quartz countertops, and an extra-large island, ideal for entertaining. The home boasts 4 bedrooms, 4 full baths, 2 half baths, 3694 square feet of living space, with 2 primary suites including a spa-like bathroom and a private deck overlooking the lake view; A 3-car garage with a gym area and sauna, an outdoor kitchen and a boat dock with an electric boatlift. Don’t miss this rare opportunity to own a slice of paradise on Lake Killarney! Contact us today to schedule a private tour.

301 Rippling Lane, Winter Park
$835,000
4 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code
Completely remodeled, coastal-inspired home is located in the highly sought-after Winter Park neighborhood of Kenilworth Shores in Winter Park 32789. Minutes from the world-renowned Park Avenue and upscale shopping, dining, parks, community events, Sunrail and more lifestyle. The home is zoned for some of Winter Park's most desirable schools, including Brookshire Elementary, Glenridge Middle, and Winter Park High School. This home is a true gem, meticulously and completely remodeled for a coastal feel that blends modern elegance with comfort. Featuring 4 spacious bedrooms + office, the residence is designed to impress. The entry showcases a custom, German-made solid front door that opens into a bright, airy living space with engineered wood floors throughout. The raised ceilings enhance the sense of openness, complemented by beautiful wood beams that add character to the home. A shiplap-clad eat-in area creates a charming focal point, while the kitchen is equipped with premium Badger Woodworks self-closing cabinetry, gorgeous granite countertops, and new appliances including espresso bar and wine fridge. No detail has been overlooked in this home, with recent upgrades including a new HVAC system and ductwork in 2024, as well as completely updated plumbing, windows, and light fixtures. Replumbed with Pex piping in 2015. The walls have been professionally retextured, and the home also offers the convenience of an interior laundry room and brand new barn door. Outside, the covered porch provides the perfect space for entertaining, with the hot tub conveys for relaxation. The outdoor bar showcases a custom millwork bar with a grill, kegerator, and fountain, ideal for hosting gatherings. A shed on a concrete slab and a workshop area in the garage offer ample storage and workspace. The property is fully fenced, ensuring privacy and security. 625 Worthington home is located in the heart of Winter Park, home to Rollins College, one of America's top-ranked liberal arts colleges. With its prime location, luxury finishes, and family-friendly neighborhood, this home offers an exceptional living experience in one of Central Florida’s most desirable areas. With the neighborhood rapidly evolving, many homes around this property are being torn down to make way for new, custom-built estates, including expansive 4,000 square foot homes valued at over $3 million.

625 Worthington Drive, Winter Park
$2,495,000
5 Beds ⋅ 4 Baths ⋅ Cortland Park SubDv. ⋅ 32789 Zip Code
Welcome to this beautifully renovated century home on one of the most picturesque brick streets in Olde Winter Park. Take a leisurely stroll down to Lake Mizell or enjoy the views from its large front patio. This classic pool home is filled with charm, natural light and is designed for easy entertaining. The spacious layout offers multiple rooms for every occasion, including a bright sunroom, cozy living room with a fireplace, and a large welcoming family room. The gourmet kitchen features custom wood cabinets, quartzite counters, a convenient office nook and an adjoining breakfast room, while the formal dining room boasts elegant moldings and built-in corner cabinets. A secret basement presents options for additional storage or a wine cellar. The second floor features a generously- sized master suite, two additional bedrooms, two updated baths, and a versatile nursery or bonus room, perfect for a study or home office. The property includes a detached two-car garage and a charming guest house with a bedroom, bath, and loft area. Newly renovated resort back yard includes heated salt water pool and spa, multiple seating areas, complete with gas hookups for fire pit and outdoor kitchen and a maintenance-free travertine and turf pool scape. You’ll love the inviting ambiance of both this home and its vibrant Winter Park location.

140 Cortland Avenue, Winter Park
$4,950,000
5 Beds ⋅ 7 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code
New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels including an expansive third-floor multi-purpose space. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open concept kitchen/gathering room along with the dining area enjoy a wall of glass doors and picture window overlooking an expansive lanai, and serene backyard with a sparkling pool and spa. The main residence offers 4 bedrooms, private home office, and multiple flex spaces, complemented by a detached pool cabana that serves as a 5th guest retreat or versatile use building. The gourmet kitchen is an entertainer’s dream, featuring dual 10-foot stone islands, a 60-inch Wolf range, dual 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, beverage center and a 146-bottle Sub-Zero dual-zone wine cooler. A separate pantry kitchen is equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample cabinetry, ideal for catering and meal preparation. The 1st-level primary suite is a tranquil retreat, offering a sitting area, an all-marble bath with a glass-enclosed shower, multiple body sprays, a soaking tub, and French doors leading to a secluded Zen garden with an outdoor shower and fountain. There is also a hidden private home office near the front of home. The second level hosts 3 additional en-suite bedrooms, a generous lounge area, bar, and a well-appointed laundry room with extra storage cabinetry. As noted previously, there is also a unique 3rd level accessible by a staircase or elevator. The outdoor living is elevated with a spacious lanai featuring motorized screens, a gas fireplace, dining space, and a summer kitchen with a 54-inch Coyote wood and gas grill, plus a separate burner beneath a remote-controlled louvered roof. There is also a detached cabana perfectly suited for a guest suite, fitness studio, additional office or game room, complete with a full bath, mini kitchen, and washer/dryer. Crafted with meticulous attention to detail, this home showcases Anderson windows, 10-foot solid doors, high-end lighting, plumbing and electrical fixtures, custom cabinetry built-ins, as well as Trane HVAC systems, ensuring quality and comfort... Lush landscaping, including magnolia trees, bamboo and cypress, surrounds the property, creating a private sanctuary. An attached side-entry garage features a powered car lift providing space for up to three vehicles. Ideally near Interlachen Country Club, Winter Park Racquet Club, Phelps Park/YMCA, and renowned Park Avenue. Note: Partial staging by RH and the furniture package can be purchased separately...

1660 Palmer Avenue, Winter Park
$411,250
2 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code
Welcome to this beautifully maintained Winter Park gem, offering exceptional curb appeal and bursting with charm, character and timeless style. Located in the highly desirable Dubsdread Heights neighborhood, bordering Little Lake Fairview and the Dubsdread Golf Course, this home places you just minutes from the boutique shops, dining options and festivals of Park Avenue, with easy access to I-4. As you step inside, you're greeted by a bright sunroom with warm, stylish Saltillo tile flooring which seamlessly flows into the spacious living room featuring stunning Red Oak hardwood floors. The eat-in kitchen boasts sleek quartz countertops, modern cabinets with crown molding, a built-in pantry with convenient slide-out drawers and newer appliances. This home has been thoughtfully updated with double-paned windows, a 2018 roof replacement and updated plumbing, ensuring peace of mind for years to come. Both bedrooms are generous in size and feature Red Oak wood flooring and modern ceiling fans, with a full bath conveniently situated in between that retains timeless charm with original custom tiling, a pedestal sink, and shower/tub combo. The private, fully fenced backyard is a true tropical retreat, perfect for relaxation or entertaining guests. The recently replaced wood deck with sail awnings and a concrete patio create ideal spaces to enjoy Florida's year-round beauty. A charming brick paver walkway leads to a separate laundry and storage shed, with additional cabinets and space to meet your storage needs. This home has gutters installed along with a rain barrel designed to capture and conserve water for your landscaping watering needs. Kitchen appliances, washer, dryer and lawn mower, edger, and blower are all included in sale. Combining the perfect blend of modern updates and original character, this home is a must-see in the heart of Winter Park!

767 Baffie Avenue, Winter Park
$480,000
3 Beds ⋅ 3 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code
NO HOA! Beautifully Remodeled Home with Expansive Garden in Winter Park Welcome to this charming and fully remodeled two-story, 3-bedroom, 3-bathroom home nestled in the heart of Winter Park. Offering a blend of modern upgrades and historic charm, this property is surrounded by a vibrant community with easy access to top destinations. Prime Location: 5 minutes to Whole Foods and Trader Joe’s 8 minutes to Downtown Orlando via I-4 (Exits 87 & 88) Surrounded by Winter Park’s historic charm Private library with an excellent book collection Weekly Farmers’ Market just minutes away Extensively Renovated in 2019: New Roof, New Windows, New A/C New Electrical Wiring & Plumbing New Driveway & Fully Fenced Yard with Entry Gate New Porch & Open-Concept Kitchen Versatile Living Space: This single-family home offers flexible living arrangements and can also function as a duplex: Downstairs: 1 bed, 1 bath, spacious living room with modern kitchen combo Upstairs: 2 beds, 2 baths, large family room, and a covered porch with scenic views Outdoor space on the porch for entertaining All permits are available on the Orange County Property Permit website for complete peace of mind. Don't miss this rare opportunity to own a beautifully updated home with endless potential in a highly desirable location! Contact us today for a private showing.

423 Ololu Drive, Winter Park
$1,180,000
4 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Charming One-Story Home in the Heart of Winter Park with an incredible pool area. Nestled in the heart of Winter Park, this elegant one-story home features a classic brick circular driveway and a welcoming covered front porch. Inside, the original hardwood floors add warmth and character to this four-bedroom, four-bathroom residence plus an exquisite detached home-office room , located in the beautiful outdoor patio area. This fifth bedroom offers a versatility that could be used as an office or a cozy den. The spacious living and dining area boasts high vaulted ceilings and a wood-burning fireplace, creating the perfect atmosphere for entertaining. The open floor plan seamlessly connects each space, offering both style and functionality. The primary suite is a peaceful retreat, with French doors opening to the pool area, a large walk-in closet, and an en-suite bathroom featuring a glass tile shower. Step outside into your private oasis, where the brick patio, wood trellis, and sparkling pool with water features create a serene escape. The oversized 95 x 150 lot is shaded by mature oak trees, with paved walkways enhancing the peaceful ambiance. Additional House Benefits include: Remodeled living room ; Original wood fireplace ; New AC (2021) ; Tankless water heater 2021 ; Dual masters ; 4 full baths ; Insulated 2 car garage with exAC Garage ; New vinyl flooring ; Remodeled office / guest room with built-in cabinets ; Heated swimming pool ; Renovated backyard with artificial grass and summer kitchen (outdoor furniture negotiable) ; New detached office space w/ air conditioning ; Outdoor ambient lighting ; New alarm system ; All appliances will stay ; Extended Kitchen Island ; New sprinkler system ; Outdoor shed storage; Acclimate Attic ; New PVC Wood Deck ; Water filtration system in the kitchen ; Underground gas line for stovetop, water heater, and pool heater Located just minutes from Windsong, Park Avenue, Baldwin Park, top-rated schools (Brookshire, Glenridge, WPHS), parks, dining, and shopping, this home offers both charm and convenience.

181 N Phelps Avenue, Winter Park
$1,516,500
3 Beds ⋅ 2 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code
A special opportunity awaits on one of Winter Park’s most sought-after streets, BELOIT AVENUE! This charming 3-bedroom, 2-bathroom home is perfectly positioned just two blocks from the vibrant energy of Park Avenue and steps from the lush greens of the Winter Park 9 Golf Course. Brimming with character and warmth, this jewel box offers over 2,400 square feet of beautifully designed living space. High ceilings, elegant crown molding, and a seamless mix of tile and gleaming hardwood floors in every bedroom create a sense of lightness and luxury. The expansive family room extends off the back of the home, opening effortlessly to a screened-in patio, perfect for enjoying the Florida lifestyle year-round. With an ideal blend of charm, location, and livability, this home is a true treasure in the heart of Winter Park. Enter through the foyer and prepare for seamless indoor/outdoor entertaining, with an inviting living room and dining room, elegantly separated by a gorgeous double-sided gas fireplace, and lined with sliding glass doors that lead to the open, paver patio. The kitchen is complete with stainless steel appliances, a natural-gas cooktop, timeless cabinetry that offers an abundance of storage, and a built-in breakfast bar. You’ll love the ideal split-bedroom floor plan, featuring an oversized primary suite that overlooks the expansive side patio accessible through sliding glass doors. Off the front living room hallway are 2 secondary bedrooms with walk-in closets, and a full bathroom. Wrapped in low-maintenance landscaping with elegant uplighting, all surrounded by concrete privacy walls with gates, this turnkey home is perfect for an active lifestyle. A private alley drive for Beloit homeowners leads to a spacious 2-car garage with built-in cabinets and attic storage. Enjoy a NEW A/C unit (2024), new washer/dryer (2024), and one of the best locations in the City of Winter Park!!

335 Beloit Avenue, Winter Park
$1,075,000
4 Beds ⋅ 3 Baths ⋅ Winter Park Heights SubDv. ⋅ 32789 Zip Code
Step into this stunning one-story Spanish Mediterranean home, beautifully renovated in 2006 by renowned E2 Homes. Offering four bedrooms and three baths, this thoughtfully designed residence seamlessly blends timeless charm with modern comforts. The inviting living room features a cozy gas fireplace, setting a warm tone for the home. A formal dining room connects to the spacious kitchen through a convenient butler’s pantry. Designed for the chef at heart, the kitchen boasts a large island with a gas range and hood, abundant cabinetry, and generous counter space, along with a breakfast nook that overlooks the family room. Beautiful brand new (May 2025) Silestone countertops in kitchen, butler's pantry, office/study & laundry room, making each space light & bright. French doors open from the family room to a covered lanai, creating a space for indoor-outdoor living. A dedicated office/study or flex space leads to the private primary suite. The primary bedroom has its own set of French doors opening to the lanai and includes a custom walk-in closet. The primary bath is a serene retreat with dual sinks, a large soaking tub and a walk-in shower. The second bedroom enjoys an en-suite bath, while two additional bedrooms feature custom closet systems for maximum organization. The large fenced backyard offers ample space for a future pool, providing endless possibilities for outdoor enjoyment. Close proximity to the shopping and dining district of Park Avenue in downtown Winter Park, this remarkable home offers the ideal blend of comfort, convenience and style. ***NOTE: all interior walls recently painted neutral soft white... also, this home has accessible elements to it, including a handicapped ramp in garage.

1690 Oneco Avenue, Winter Park
$430,000
3 Beds ⋅ 2 Baths ⋅ Fairbanks Shores Sixth Add SubDv. ⋅ 32789 Zip Code
Discover a true slice of paradise just minutes from downtown Orlando, nestled along the serene shores of Lake Fair. This meticulously maintained 3-bedroom, 2-bathroom home, built in 1958, reflects an era when craftsmanship and attention to detail were paramount. The moment you step through the front door, you’ll be captivated by the original pine floors, gleaming with character and charm. Straight ahead, a massive living room invites you to unwind, complete with a Yamaha surround sound system—perfect for movie nights or entertaining. To your left, the spacious dining room and kitchen boast a 9-foot solid surface island with a farmhouse sink, 42" quiet-close cabinets, and a real tile backsplash (no peel-and-stick here!). The bathrooms have been beautifully renovated, offering a touch of modern luxury while maintaining the home's timeless appeal. The primary suite is a true retreat, featuring plantation shutters that add elegance and privacy. Step outside to a lush, tropical oasis where palms and landscaping create an ultra-private setting—ideal for cozy evenings around a firepit or swaying in a hammock with a gentle lake breeze. A 20x10 screened porch overlooks the lake, providing a perfect spot for morning coffee or unwinding at sunset. Adjacent to the kitchen, the laundry room is conveniently located just outside the side door. The enormous 2-car carport offers ample coverage for your vehicles, keeping them protected from the elements after a trip to the store. And for fishing enthusiasts? The seller has reeled in 5 lb. bass right from the backyard! Beyond this stunning home, the location is unbeatable. You're just minutes from the vibrant dining and shopping scene of Winter Park, home to award-winning restaurants, charming boutiques, and cultural hotspots like the Winter Park Farmers’ Market and Park Avenue. Downtown Orlando is a short drive away, offering easy access to the city's best entertainment, including Lake Eola Park, where you can enjoy fireworks, swan boat rides, concerts, and year-round festivals like the Orlando Film Festival and the Spring Fiesta in the Park. For nature lovers, this home is just minutes from Leu Gardens, a breathtaking 50-acre botanical garden featuring stunning tropical plants, butterfly gardens, and scenic walking trails. It also hosts outdoor movie nights, educational workshops, and seasonal events like the Dazzling Nights light festival. Also nearby is Mead Botanical Garden, a 47-acre nature preserve in Winter Park, offering hiking trails, butterfly gardens, a boardwalk, and even a community garden. It’s the perfect place for birdwatching, photography, or a peaceful escape into nature. Don’t miss the chance to own this lakefront gem—a perfect blend of historic charm, modern upgrades, and an unbeatable location. Schedule your private tour today!

328 Lake Fair Lane, Winter Park
$905,000
3 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 02 SubDv. ⋅ 32789 Zip Code
Welcome to 533 Balmoral Road, a beautifully updated mid-century modern gem nestled in the desirable Kenilworth Shores neighborhood of Winter Park. This 3-bedroom, 3-bathroom residence, spanning 1,900 square feet, offers a harmonious blend of classic design and contemporary upgrades. As you step inside, you'll be greeted by an open-concept layout that seamlessly connects the living area and kitchen, with a wood burning fire place creating an inviting space perfect for both relaxation and entertaining. The heart of the home is its modernized kitchen, featuring sleek cabinetry, quartz countertops, and stainless steel appliances, catering to the needs of today's discerning homeowner. One of the standout features of this home is the unique central courtyard, visible from the main living areas, providing a serene outdoor retreat and flooding the interior with natural light. The thoughtful design ensures a seamless indoor-outdoor living experience, ideal for Florida's pleasant climate. The private quarters include three generously sized bedrooms. Two of these boast en suite bathrooms, offering added convenience and privacy, while the third bedroom is serviced by a well-appointed hall bath. An additional bonus room could be used as an office, dining, sunroom or whatever you desire. Each space has been thoughtfully designed to provide comfort and style. Situated in the heart of Winter Park, this property offers more than just a beautiful home and lush landscaping. Residents will appreciate the proximity to top-rated schools, picturesque parks, and the vibrant local dining and shopping scenes. The community's tree-lined streets and friendly atmosphere make it a sought-after location for families and professionals alike. Experience the perfect blend of mid-century charm and modern amenities at 533 Balmoral Road—a place you'll be proud to call home. Upgrades include: New Paint & Finishes, Modernized Bathrooms (New vanities and a renovated master shower) Custom Master Closet, New Interior Doors and windows, New Upgraded HVAC System (2021), Tankless gas hot water heater, Roof (2020), HVAC (2021) Exterior Stone Façade, Updated Landscaping & Outdoor Living spaces (Lanai, pergola, and firepit) irrigation, New Front Door & Exterior Lighting, Solar Panels (paid off) Security System Ready (Wired for easy setup) Upgraded Laundry Room (Added storage, tile, and cabinetry)

533 Balmoral Road, Winter Park
$987,500
4 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code
Charming Spanish-Style Bungalow with Private Oasis in the Heart of Winter Park. Step into the elegance of Old Florida with this exquisite Spanish-style bungalow, nestled in Winter Park. Offering the perfect blend of historic charm and modern luxury, this 4-bedroom, 2.5-bath retreat is a hidden gem surrounded by lush, mature landscaping, creating a private sanctuary just minutes from the best Winter Park has to offer. From the moment you arrive, you’ll be captivated by the stunning curb appeal, featured on the front cover of Home & Garden magazine. The beautifully maintained exterior, with its 2023 terracotta-styled flat roof sets the stage for what lies within. Inside, timeless character meets contemporary upgrades. French terracotta flooring, antique hardware, and neutral warm tones create an inviting atmosphere, while thoughtful renovations ensure every modern convenience is at your fingertips. The kitchen is a chef’s dream, boasting vanilla quartz countertops with gold flecks, beautifully complementing the bronze accents and upgraded appliances. The open-concept design seamlessly connects the kitchen, dining, and living area ideal for entertaining. For more intimate gatherings, unwind in the spacious family room or soak in the natural light from the attached sunroom, which overlooks the lush backyard retreat. Step outside to a tranquil space perfect for morning coffee or evening cocktails, all while enjoying the peaceful sounds of nature. The pool and jacuzzi (new heater installed in 2021) add a touch of resort-style living, surrounded by meticulously curated landscaping with extensive landscape lighting (2022) that enhances the homes enchanting ambiance. Situated in a vibrant, walkable neighborhood known for its tree-lined streets and friendly atmosphere, this home is just a short stroll to Lake Knowles, the YMCA, and Phelps Park. Bring your golf cart and enjoy easy access to Interlachen Golf & Country Club or the Winter Park Racquet Club. Plus, you’re less than a mile from the newly renovated Winter Park Hospital and just minutes from Park Ave world-class dining and shopping. Top-rated schools: Zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. This rare, character-filled home offers a perfect blend of privacy, luxury, and location. Don’t miss your chance to own a piece of Winter Parks most desirable neighborhood!

1585 Chestnut Avenue, Winter Park
$750,000
3 Beds ⋅ 2 Baths ⋅ Flora Park SubDv. ⋅ 32789 Zip Code
VALUE IS IN THE LAND. LOT IS 90 X 150+- GREAT OPPORTUNITY TO BUILD YOUR DREAM HOUSE IN 32789. HOUSE NEEDS EVERYTHING AND WILL BE DIFFICULT TO GET INSURANCE. LOCATED ON PRIVATE, DEAD END STREET. CLOSE TO YMCA, PHELPS PARK, INTERLACHEN CC. GREAT WP SCHOOLS. SURVEY AVAILABLE IN ATTACHMENTS.

1811 Oneco Avenue, Winter Park
$1,877,500
5 Beds ⋅ 6 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
Nestled in the highly sought-after Orwin Manor neighborhood of Winter Park, this stunning Spanish Revival home at 1446 Berkshire Ave, offers a luxurious lifestyle with unparalleled proximity to Winter Park’s finest amenities including Historic Park Avenue and Rollins College. Located on a tree-lined street, this residence exudes timeless elegance, complemented by a circular driveway that leads you to its impressive facade. The home has been thoughtfully updated with fresh interior and exterior paint, along with the addition of three new HVAC systems, ensuring modern comfort throughout. Boasting over 4,000 square feet of living space, the home features five generously sized bedrooms, including a second-floor Primary Suite that offers both luxury and privacy. The suite is complete with a private sitting area, a terrace overlooking the lushly landscaped grounds, and a spa-like bath with dual sinks, jetted tub, and a walk-in shower. A spacious walk-in closet provides ample storage space and custom built-ins. In addition to the three bedrooms, the second-floor features a spearate bonus room that is perfect for a private office, or could be converted to an in-law/guest suite, adding versatile living space to the property. The chef’s kitchen is a culinary dream, featuring solid wood 42” cabinetry, elegant granite countertops and a new subway tile backsplash. Adding to the Kitchen's functionality and sophistication are Copper prep and main sinks, Wolf Natural Gas Range, dual dishwashers, under counter ice maker and a walk-in pantry, A separate casual dining space and an island/breakfast bar seamlessly open into the family room, creating an ideal setting for everyday living and entertaining. Off the Kitchen and family room is a full guest bathroom with built in desk area and a multifunctional game room that could convert to a 6th bedroom. Outside, the private oasis is designed for both relaxation and entertainment. A resort-style pool with tranquil fountains serves as the centerpiece, while a beautifully crafted Spanish styled privacy wall, accented with lighting and peaceful bamboo, offers a serene atmosphere. Enjoy the cooler evening relaxing around the piped natural gas fire pit. Enjoy the expansive Cabana area includes a summer kitchen, as well as dedicated seating and dining areas, all overlooking the pool and lush landscaping. With its prime Winter Park location, exceptional privacy, and resort-style amenities, this remarkable home offers the perfect blend of style, comfort, and convenience in one of Winter Park’s most desirable neighborhoods.

1446 Berkshire Avenue, Winter Park
$1,100,000
3 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Luxury is a lifestyle, and this Winter Park modern bungalow on a cobblestone street is full of natural light, clean lines and crisp open spaces. Three bedrooms and 2.5 baths in the main house, this home has been thoughtfully renovated with style and beckons the green of an outdoor lifestyle. Over 2,400 square feet in main house and the garage was converted to an additional dwelling unit, adding an additional 400 square feet or so, current use is a studio, can easily transform to a guest house, mother-in-law suite or back to a garage, whatever function fits your needs. Front motor court can accommodate lots of vehicles, easy in and out and includes electric car charging station. The kitchen is open to the gathering room with spacious volume ceilings. Home was recently renovated with stainless appliances, including a Thermador gas range, clean-line cabinets with glass door accents, Cambria Gold quartz countertops, counter seating, a farmhouse sink and gorgeous window to the outside. Main living space is anchored by warm wood floors, with marble floors in bedrooms, all generous in size, with fresh light walls and an extensive lighting package throughout. All baths are updated with marble-influenced accents and gold finishes. Primary suite enjoys sleek authentic Carrera marble seamlessly throughout with walk-in closet for great organization. A luxurious bath retreat showcases a soaking tub, dual sinks and a chic open shower with a frosted window. The natural light in this home adds to the beauty in all spaces. Glass slider doors invite you to the outdoor oasis with an expansive covered pergola, cover is waterproof with the Hercules roof system. Lush greenery and mature landscape and majestic oaks round out the space and topped off with an upscale bar for making entertainment simple. This home was extensively renovated including roof and gutters, re-pipe, newer air conditioners, electrical panels, gas tankless water heater, parking motor court, professional landscape and landscape lighting, the additional separate studio recently updated, paved courtyard, bistro lighting and more. Location is paramount near Winter Park Racquet Club, terrific schools, zoned for Winter Park High, close to Park Avenue, fantastic shopping and restaurants. A great investment opportunity to live among the finest homes in Winter Park and in well-established neighborhood providing a lifestyle like no other.

1932 Temple Drive, Winter Park
$520,000
4 Beds ⋅ 3 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
Welcome Home to Orwin Manor – Where Historic Charm Meets Modern Comfort! Nestled in the heart of Winter Park’s highly sought-after Orwin Manor, this 1926 historic gem is brimming with character and thoughtfully updated for today’s lifestyle. Priced below a recent appraisal, this four-bedroom, three-bath home showcases original hardwood floors, a brand-new roof (2024), and reinforced crawl space floor joists, preserving its timeless beauty. Zoned R2, this property offers incredible flexibility with an in-law suite and a detached ADU (Accessory Dwelling Unit) featuring its own private entrance and bathroom—perfect for multi-generational living, a home office, or income-producing rental potential. Step inside to find modern upgrades, including all-new windows, a new irrigation system, a freshly paved driveway, a new water heater, interior paint, granite kitchen countertops, and remodeled bathrooms. Plus, enjoy peace of mind with a transferable termite bond and a recently serviced A/C. Beyond your front door, enjoy a prime location just minutes from Rollins College, boat tours, art festivals, farmers markets, and charming local coffee shops. With easy access to I-4, 1792, Maitland, and downtown Orlando, you’re perfectly positioned for both work and play. Located near top-rated schools like UCF, Rollins College, and Stetson, and just a short drive to world-renowned beaches and theme parks, this home offers endless possibilities. Don’t miss out on this rare opportunity—schedule your private showing today!

1481 Harmon Avenue, Winter Park
$3,295,000
4 Beds ⋅ 6 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Stunning turnkey luxury home in one of the sought-after neighborhoods of Winter Park. Experience unparalleled luxury in this breathtaking four-bedroom, six-bath estate built in 2020, offering over 4,300 square feet of exquisitely designed living space. Every bedroom is a private retreat with its en-suite bath, and the home is adorned with designer finishes and exceptional craftsmanship throughout. Step into the expansive great room, a versatile space that seamlessly blends formal and casual living, featuring a glass-enclosed temperature-controlled wine room, a gas fireplace and a chic dry bar. The chef’s kitchen is a culinary dream, showcasing a massive quartz island, top-of-the-line Thermador six-burner plus griddle gas range with double ovens, a separate freezer and refrigerator, beverage refrigerator, and a spacious walk-in butler’s pantry with a built-in convection microwave and warming drawer. The primary suite is a sanctuary of luxury, featuring dual spa-like baths, a stunning soaking tub, a steam shower, a smart toilet, custom-designed dressing rooms and a hidden safe room. French doors lead to a private lanai with a seating area, an outdoor tub and a serene open-air shower. Upstairs, a spacious 23-by-15-foot family room connects three additional bedroom suites, each with its private bath. One of the bedrooms features a hidden passageway to a 12-by-7-foot bonus room, ideal as a playroom, private media space or climate-controlled storage. Designed for seamless indoor-outdoor living, a 21-by-20-foot covered lanai with a gas fireplace and motorized screens extends from the kitchen and great room via folding glass doors. The two outdoor retreats include a sun-soaked pool deck, built-in grill, firepit, turf lawn, built-in trampoline and basketball court. Additional highlights include a drop-zone off the two-car garage for added convenience. On a charming brick-lined street, this home offers prime access to Park Avenue’s premier dining and shopping, downtown Orlando, major hospitals and Orlando International Airport just 25 minutes away. A rare opportunity to own a turnkey masterpiece that offers the ideal balance of comfort style, and exceptional entertainment spaces.

100 E Rockwood Way, Winter Park
$3,130,000
5 Beds ⋅ 6 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Exquisite Winter Park residence built by Davila Homes, where luxury meets functionality. This impressive home features 5 spacious bedrooms, 5.5 beautifully designed bathrooms, and a generous 4,188 square feet of meticulously crafted living space. As you step through the glass front doors, you’re immediately greeted by the grandeur of beautiful hardwood floors and the high ceilings. The chef-inspired kitchen boasts quartz countertops, custom cabinetry, and top-of-the-line Thermador Appliances, perfect for the chef in the family. The open-concept living, dining, and kitchen areas flow seamlessly, creating an inviting atmosphere for everyday living and entertaining. The primary bedroom suite offers a peaceful retreat with a separate sitting area and massive glass sliding doors with views of the pool and back yard. The spa bath features a wet room with a large walk-in shower and freestanding tub, there is also a spacious walk in closet, and dual vanities with custom cabinetry and quartz countertops. On the second floor you will find three additional bedrooms, each with its own private bathroom, and a massive bonus room with a secret hidden playroom for the little ones. Outside, the home continues to impress with a full covered lanai with retractable screen, ideal for relaxing and enjoying Florida’s beautiful weather. There is also a full summer kitchen, a sparkling pool with a hot tub, and ample backyard space with lush landscaping. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park features. Schedule your private showing today and experience the epitome of luxury Winter Park living.

210 E Lake Sue Avenue, Winter Park
$1,555,000
4 Beds ⋅ 3 Baths ⋅ College Place Rep SubDv. ⋅ 32789 Zip Code
Iconic Winter Park treasure! Welcome home to 817 Antonette, an architecturally inviting residence that exudes quality and charm. This thoughtfully designed home boasts detailed moldings and millwork, wood floors, high ceilings, and beautiful oversized windows throughout. A grand foyer leads to a central gallery with an atrium and a custom-designed bannister, while a unique glass ceiling allows for an abundance of natural light. Perfect for entertaining, the home features a large dining room and a chef's kitchen equipped with professional-style appliances, a walk-in pantry, and a built-in banquette. The spacious family room, complete with a fireplace, has French doors that open to a charming outdoor terrace. The versatile floor plan incorporates both formal spaces and options for a home office, nursery, or music room. The main home includes four bedrooms and three baths. The upstairs primary suite is a luxurious retreat, offering a spa-like bath, an oversized closet with built-ins, and a separate room perfect for an office or nursery. The large secondary bedrooms have walk-in closets and are connected by a Jack and Jill bath. Your guests will appreciate the detached apartment, which offers privacy with a full bath, kitchen, and separate courtyard—ideal as a fifth bedroom. Situated on one of Winter Park’s most charming brick streets in the historic College Quarter, this home is just a short stroll to a private neighborhood dock on Lake Virginia. Walk to Park Avenue’s shops and restaurants, Rollins College, the farmer's market, and the Sunrail station. The home celebrates its Federalist architecture with precise and thoughtful details while seamlessly integrating modern amenities. Additional features include an oversized side-entry two-car garage, a new roof installed in 2022, and many windows replaced in 2020. This property is zoned for top-rated schools, including Audubon K-8 and Winter Park High School. Don't miss the opportunity to schedule a private viewing of this unique, one-of-a-kind treasure!

817 Antonette Avenue, Winter Park