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$715,000
4 Beds 2 Baths Kenilworth Shores Sec 04 SubDv. 32792 Zip Code
Discover one of the sought-after communities in Winter Park, Kenilworth Shores, where mature oak trees frame the streets, spacious parks serve as gathering ground for families and peaceful walking trails weave through the neighborhood. Centrally within arm’s reach of luxury shopping on Park Avenue in Winter Park, stunning lake views and parks in Baldwin Park, and chef-driven local restaurants in Audubon Park. Kenilworth Shores isn't just a location, it's a community, and this four-bedroom, two-bath Florida ranch is your family's invitation to join. At nearly 1,600 square feet, this home provides charm, function and thoughtful design with upgraded LVP flooring flowing throughout the easy layout. Old world brick detailing gives the exterior genuine curb appeal, while a thoughtfully renovated interior delivers a ready-to-move-in home. A gorgeous brick fireplace anchors an open kitchen, family and dining room combination, with loads of natural light and function to entertain in style. The kitchen is outfitted with white shaker custom cabinetry, granite counters, a soft glass tile backsplash, stainless steel appliances and glass pendant lighting over bar seating. A desirable split-bedroom plan provides privacy for guests, while the primary suite opens to the backyard and includes a completely renovated main bath. The flexible fourth bedroom is outfitted with a custom-designed built-in Murphy bed system with flanking closets and storage. Sitting off the primary living area, this bedroom provides options to fit flexible needs such as home office, guest room, playroom or secondary family space. Go into the backyard and experience your personal Florida oasis with a screened covered porch and grand Florida pool to cool off in the heat of summer. The surrounding, spacious yard is adorned with artificial turf (beautiful, durable and effortlessly low maintenance), complete with a putting green that will make this yard the destination for every playdate, summer barbecue or birthday party. Completed upgrades include new roof (2021), resurfaced pool (2021), new irrigation and well (2022), new wood fence (2023), new dishwasher and built-in microwave (2023), HVAC (late 2023), new washer and dryer (2024), and new pool pump motor (2025). The best part of this special neighborhood is the connected community. Zoned for Brookshire Elementary, Glenridge Middle and WP High, some of the best Orange County Schools. Cady Way Park is nearby with a community pool, baseball fields, a playground, pickleball courts, and miles of recreational and bike trails. This location checks all the boxes. Schedule your private showing today.

688 Brechin Drive, Winter Park

$581,000
4 Beds 3 Baths Enclave At Aloma SubDv. 32792 Zip Code
Come see this BEAUTIFULLY MAINTAINED, EMACULATE WINTER PARK HOME ON A QUIET STREET IN A SECLUDED GATED ENCLAVE OF HOMES! This is a one owner home and has been maintained in pristine, like new condition. Located in a small gated community moments from Trinity Preparatory School, Park Avenue Shoppes and Rollins College. When entering this home you are greeted by a beautiful entry way and foyer. This single story four bedroom home has a spectacular open floor plan with natural lighting galore and beautiful wood look tile throughout the entire home, stainless steel appliances, stunning granite countertops, a large island in the kitchen, custom extended cabinetry perfect for the cooking enthusiast and great for entertaining, master bedroom extended with sitting room, beautiful back lanai and a large backyard that is beautifully designed! When entering the back lanai you are greeted by a serene, private, landscaped Oasis. The landscaping and location of the home within the community creates an amazingly private, secluded and peaceful backyard with just the occasional sounds of birds chirping. This home is in an amazing location! You will be located about one mile to Trinity Preparatory School, Publix, Restaurants and more shopping as well as the 417, you are just a few miles from Rollins College, Park Avenue/Downtown Winter Park, Advent Health Winter Park, The Country Club at Deer Run, Interlachen Country Club, St. Luke’s School and Masters Academy just to name a few and more shopping & restaurants galore! This is a prime location for all conveniences and with a Winter Park Address! This home has some of the latest energy qualities such as double pane insulated windows and has been constantly covered under a termite bond. Come visit this Warm, Friendly Neighborhood because you are sure to want to stay forever! Updates in the last 1 to 2 years include: Painting of complete exterior and interior, All kitchen appliances replaced, flooring replaced, bathrooms updated, backsplash in kitchen added, tile on front porch and back lanai, soft close on all kitchen cabinets, extension of kitchen cabinets & countertops into dining room. HVAC system has been and is serviced constantly since home was built.

7917 Pleasant Pine Circle, Winter Park

$445,000
4 Beds 2 Baths Carolyn Estates SubDv. 32792 Zip Code
Welcome to Carolyn Estates in highly desirable Winter Park—a charming enclave of just 63 homes ideally located near Lake Howell High School. This beautifully renovated residence offers a truly unique floor plan—the only one of its kind in the community. Featuring 4 bedrooms, 2 bathrooms, and a spacious 2-car garage, this home blends comfort with functionality. Enjoy cozy evenings by the wood-burning fireplace or unwind in the screened-in patio, perfect for relaxing or entertaining. Step inside to an inviting open-concept layout highlighted by soaring ceilings and abundant natural light. Renovated in April 2026, this home showcases numerous upgrades, including fresh interior and exterior paint, new sod and lush landscaping, a fully remodeled second bathroom, new convection range and microwave, updated interior door hardware, a complete electrical update, and new lighting and ceiling fans throughout. Additional major improvements include newer windows and hot water heater (2019) and full home replumbing (2022), providing added peace of mind. Seller will provide a $10,000 credit towards a new roof with Full Price Offer. This move-in-ready home combines modern updates with a prime location—schedule your private showing today!

1832 E Cheryl Drive, Winter Park

$799,900
4 Beds 4 Baths Meadows At Hawks Crest SubDv. 32792 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 1287 Verdant Glade Place in Winter Park, a spacious two-story home offering 4 bedrooms, 3 full baths, 1 half bath, and a dedicated office, all thoughtfully arranged within an open floorplan designed for both comfortable living and easy entertaining. Inside, the home feels bright, expansive, and well connected, with generous living areas that flow naturally from one space to the next. The open design creates an inviting setting for everyday routines, gatherings, and holiday hosting, while the separate office adds flexibility for working from home, studying, or creating a quiet retreat. With two primary bedroom suites, a large game room, and an additional loft, there is plenty of space to accommodate guests, a growing household, or changing lifestyle needs. The home also features thoughtful upgrades that elevate both style and function. A gourmet kitchen serves as the heart of the home, complete with quartz countertops, 42-inch cabinetry, and the kind of workspace and storage today’s buyers appreciate. Eight-foot interior doors add to the sense of scale throughout, while details such as a pocket door in the bathroom enhance convenience and flow. Large sliding glass doors open wide to create a seamless connection between the indoor living spaces and the outdoor entertaining area. Step outside to an oversized screened and covered patio that extends the living space and creates a relaxing place to enjoy morning coffee, outdoor dining, or quiet evenings at home. Beyond the patio, the private yard offers even more appeal, with no rear neighbors behind the home for added privacy and a more open feel. The rear eastern exposure welcomes beautiful morning sun, making the backyard setting especially enjoyable at the start of the day. Located in Winter Park, the home benefits from a highly desirable area known for its established residential feel, convenient access to shopping and dining, and close proximity to parks, schools, and major roadways. The neighborhood adds to the home’s appeal by offering a blend of comfort, accessibility, and the everyday convenience that makes Winter Park such a sought-after place to live. With its flexible two-story layout, dual primary suites, game room, loft, gourmet kitchen, oversized patio, and private backyard setting, 1287 Verdant Glade Place delivers the space, upgrades, and lifestyle features buyers are looking for.

1287 Verdant Glade Place, Winter Park

$470,000
4 Beds 2 Baths Replat Of Lts 1 2 & 3 Brookside Sub SubDv. 32792 Zip Code
SWIM WHENEVER YOU LIKE! Discover a new dimension of living - Sparkling pool awaits you, so come and dip your toes here! Pool party ideas come naturally in this proud-to-show huge fenced-in backyard with lots of entertaining space. Oversized pool deck and large rock patio, plus huge screened in porch, make a great space for Florida living. This rock-solid ranch offers 4 bedrooms and 2 baths set in over 1700+ sf. Great curb appeal with cool rock trimming and freshly landscaped beds. Roomy formal living room greets you as you enter. The primary bedroom is split from the other 3 bedrooms and lies off the living room. This primary suite offers closet space galore. Plus, pretty double vanity, separated from the shower area. Terrific, updated kitchen with neat rustic tile, quartz counters, tile backsplash, stainless appliances, cool single bowl sink and faucet, shiplap wall and closet pantry round out this kitchen space. The family room is a great size, and the kitchen quartz counter/bar also serves as a gathering place flowing into the family room, which features a shiplap TV wall and blind-inside sliders to the screened in porch. The other 3 bedrooms and 2nd bath are off the family room. All are nice sized and the bath with nifty vintage tile, has an access door to outside/pool area. Pretty luxury vinyl plank flooring through living areas. All set in Winter Park on a .23 acre lot and Cul-De-Sac street. Conveniently close to schools, hospital, shopping, Costco and restaurants. Plus, easy access to highway 436 and straight shot to the Orlando International Airport. Don’t wait on this rock-solid ranch in desirable Winter Park...it’s ready for its new owners!

7120 Brookside Trail, Winter Park

$610,000
4 Beds 3 Baths Quail Run SubDv. 32792 Zip Code
WOW - Price Reduction!!! Experience the perfect blend of classic elegance and modern comfort in this spacious pool home. From the moment you step inside, the open spindle staircase sets a sophisticated tone that carries throughout the residence. In the Heart of the home is an upscale Kitchen equipped with solid wood cabinetry, sleek granite countertops, and a convenient breakfast bar for your morning breakfast or casual dining. Move freely from inside to outside through 3 sets of sliding glass doors in the kitchen, dining room and great room. Just walk out anytime to the massive brick paver patio and enjoy one of the two covered patio areas. The outside is Entertainment ready as the expansive brick pavers wrap around the pool, creating a seamless environment perfect for hosting summer parties or quiet evening dips. On the cool days you can retreat to the family room to enjoy the warmth of the wood-burning fireplace. The primary Suite is a true getaway featuring direct pool access via private sliders, a generous walk-in closet, and a spa-like bath. Indulge in the soaking tub or the walk-in shower with double shower heads. Includes double vanities and ample storage for a clutter-free environment. The upper level will allow family and guests to feel right at home with three spacious bedrooms and a dedicated full bathroom upstairs. You can also rest easy knowing that the Roof was installed in 2018, the Hot Water Heater was installed in 2018, and the HVAC system was installed in 2019. An oversized 2-car garage offers room for a workbench and "toys" plus an inside laundry room and convenient half-bath are located close by. This prime location is ideally situated near A/B-rated schools, UCF, and Oviedo Hospital. Enjoy easy access to the 417 and Aloma Ave with plenty of shopping, Winter Park’s nightlife and the Tuscawilla Country Club just minutes from your front door. If this sounds like YOUR Dream home, please come see it today!

2220 Fairglenn Way, Winter Park

$660,000
4 Beds 3 Baths Golfside Sec 03 SubDv. 32792 Zip Code
Welcome to this beautifully updated home offering the perfect blend of comfort, style and convenience. From the moment you arrive, you’ll notice the inviting tree-lined streets in this quiet residential neighborhood. Step inside to discover a bright, thoughtfully designed layout, filled with natural light, featuring spacious living areas and tasteful updated finishes throughout. The updated, open-concept kitchen is a true centerpiece, complete with modern appliances, ample cabinetry, a generous peninsula, and in eat-in area, ideal for gathering with family and friends. The primary suite provides a relaxing retreat with a recently updated in-suite bathroom and plenty of closet space. Additional bedrooms are generously sized, including a fourth bedroom, perfect for multi-generational living, guests, or a home office. Outside, enjoy a sparkling, screened-enclosed pool, and a private backyard oasis, with plenty of yard space to relax, play, or entertain. Whether you're hosting a weekend barbecue or enjoying a quiet evening, this outdoor space offers endless possibilities. Walk over to the Winter Pines golf course located behind the home, where you can enjoy lunch at the beautifully updated clubhouse, hit the driving range, or enjoy the seasonal community events like Santa in the Park, Movie in the Park, or occasional neighborhood happy hours. Located in the beautiful neighborhood of Winter Park Pines with amenities such as Ward Park, Brookshire Elementary, Winter Park HS, and the Cady Way bike trail, which you can take to Baldwin Park’s main street for shopping and dining, or a stroll around Lake Baldwin. Conveniently located near downtown Orlando, Park Avenue for shopping and dining, or just minutes from the 417 for commuting. Seller offering a home warranty to a buyer for the first year.

927 Fairway Drive, Winter Park

$425,000
4 Beds 2 Baths Winter Park Estates SubDv. 32792 Zip Code
Welcome to this charming home situated on a spacious lot in a quiet, established neighborhood in Winter Park. From the moment you arrive, you’ll appreciate the inviting curb appeal, expansive front yard, and peaceful setting that make this property feel like home. Inside, the home offers a light and open layout with a seamless flow between the living, dining, and kitchen spaces—perfect for both everyday living and entertaining. The updated kitchen features modern cabinetry, granite countertops, stainless steel appliances, and a functional layout with bar seating, making it both stylish and practical. The bedrooms are comfortably sized with great natural light, offering flexibility for family, guests, or a home office. The bathrooms have been thoughtfully updated, including a beautifully renovated shower with modern tilework that adds a fresh, clean feel. The Florida room in the back creates a relaxing space for drinking coffee or curling up for a family movie night. Step outside to a generously sized backyard with endless potential—whether you envision creating an outdoor entertaining space, adding a pool, or simply enjoying the open green space. With plenty of room to spread out, this yard offers the kind of flexibility that’s hard to find. Conveniently located near local shopping, dining, and major roadways, this home offers both comfort and accessibility. Zoned for great Winter Park schools. Whether you’re a first-time buyer, investor, or looking to downsize, this property presents an incredible opportunity to own a home with room to make it your own.

814 Densmore Dr, Winter Park

$765,000
4 Beds 3 Baths Winter Park Pines Merrie Oaks SubDv. 32792 Zip Code
CALLING FOR HIGHEST AND BEST OFFERS BY MONDAY, APRIL 20th at 9:00 AM. Tucked away on a quiet street in the heart of Winter Park, this fully renovated 4-bedroom, 2.5-bath pool home—enhanced by fully owned solar panels—offers a rare blend of privacy, thoughtful design, and effortless indoor-outdoor living. Set on a generous ¼-acre lot, every detail has been curated to create a home that feels both elevated and family-friendly. Inside, the home opens to a flowing layout ideal for both everyday living and entertaining. Wide-plank luxury vinyl flooring, designer tile, and a soothing, modern palette create a cohesive sense of calm throughout. The kitchen is both a statement and a gathering place, featuring an oversized island wrapped in Taj Mahal quartzite, stainless steel appliances, and a custom wine bar—designed for connection, conversation, and celebration. Adjacent to the kitchen, the sunroom is a showstopper bathed in natural light and enhanced with custom built-ins, this versatile space effortlessly transforms into a home office, playroom, or entertainment lounge. This is where this home comes alive; perfect for large gatherings. The primary suite offers a serene retreat, highlighted by a fully remodeled spa-inspired bathroom with a soaking tub and a sleek, modern shower; inviting you to slow down and unwind. Outside, the newly added 800-square-foot turf play area, side yard, and green space surrounding the pool create room to play, entertain, and relax. The cul de sac and backyard feel exceptionally private, quiet, and peaceful. Just minutes from Park Avenue, you are surrounded by boutique shopping, acclaimed dining, lakeside strolls, and a lifestyle that feels both vibrant and relaxed. From morning coffee runs to evening walks under oak-lined streets, this is the essence of Winter Park living. This home is more than move-in ready—it’s a place to gather, grow and live. ROOF (OCT. 2022) HVAC (2017) WATER HEATER (2016) PLUMBING (2020) ELECTRICAL (UPDATED 2026) POOL PUMP/MOTOR (2020), POOL RESURFACED (2017) DRAIN SYSTEM: FRENCH DRAINS, SUMP PUMPS, GUTTERS (2024)

2681 Fitzhugh Road, Winter Park

$500,000
4 Beds 2 Baths Eastbrook Sub Unit 13 SubDv. 32792 Zip Code
This beautifully updated 4-bedroom, 2-bath bungalow with a 2-car garage sits on a quiet cul-de-sac and underwent a major renovation in 2023. Nearly every big-ticket item has been replaced, including the roof, A/C, water heater, and double-pane windows-giving you peace of mind for years to come. The home also features a fully updated kitchen with new cabinets, countertops, and a complete appliance package—refrigerator, dishwasher, range, range hood, and microwave—along with new carpeting, ceiling fans, and a new front door. Inside, the spacious family room includes custom built-ins, offering an abundance of storage. Both bathrooms have been tastefully remodeled. The primary bath features a beautiful walk-in shower and dual sinks, while the guest bath offers dual sinks, a jetted tub, a linen closet, and convenient access to the pool area. Step outside to an oversized, fully fenced backyard where you’ll find a sparkling screened-in pool and a large covered patio with an extended overhang—perfect for relaxing or entertaining year-round. And best of all…No HOA! Conveniently located minutes from Downtown Winter Park, key highways, shopping and within an hours drive of all the major theme parks and Orlando International Airport. Welcome Home!

1905 Bonanza Ct, Winter Park

$600,000
4 Beds 3 Baths Lost Creek SubDv. 32792 Zip Code
Nestled in the upscale Lost Creek community, this maintained 4-bedroom, 3-bathroom screened pool home offers the perfect blend of comfort and natural beauty with over an acre of land that extends all the way to Howell Creek. Upon entering, you are greeted by high ceilings and an open-concept great room layout. The formal living room flows seamlessly into the dining room, creating an ideal setting for entertaining. Beyond, a spacious family room opens to views of the pool, while the adjacent gourmet kitchen and breakfast area complete the heart of the home. The kitchen features New quartz countertops and stainless steel appliances. The main level is home to a spacious primary bedroom, offering serene views of both the pool and surrounding forest. Sliding doors provide direct access to the pool deck, while inside you'll find a generous walk-in closet, a double-sink vanity, a relaxing garden bathtub, and a separate shower. Additional guest bedroom and a full guest bathroom complete the main floor. Upstairs, a charming loft with a built-in desk provides the perfect work-from-home or study retreat, accompanied by two additional bedrooms and a shared bathroom. Outside, the screened pool backing up to a natural wooded area with no rear neighbors is your private oasis — perfect for year-round Florida living. Winter Park is close to numerous shops and eateries along with easy access to major expressways. You get all this in a great school district. Sod intalled(2026), Quartz Countertops(2026), Pool pump(2026), Range & Dishwasher(2026), Roof(2022)

3110 Heartleaf Place, Winter Park

$1,349,000
4 Beds 4 Baths Eastgate Sub SubDv. 32792 Zip Code
Step into elevated Florida living with this stunning brand-new residence, where modern design meets lasting quality. Constructed with solid block and steel framing for superior durability, this home is quietly nestled on a cul-de-sac in one of Winter Park’s most up-and-coming areas—without the restrictions of an HOA. Just moments from Interlachen Country Club and the charming Lakemont Heights neighborhood, the location offers both prestige and convenience. From the moment you enter through the impressive double doors, you’re welcomed by a light-filled, open-concept design. Soaring 10-foot ceilings and elegant 8-foot doors create an airy, expansive feel, while abundant natural light highlights the home’s sleek, contemporary finishes. At the heart of the home, the chef-inspired kitchen truly shines. Outfitted with luxurious quartz countertops, stainless steel appliances, and a custom LED-lit wine display, it’s designed to impress. The seamless flow into the living and dining spaces—along with views of the backyard—makes it perfect for entertaining or everyday connection. The primary suite is a private sanctuary, offering a spa-like escape with dual vanities, a spacious dual-entry shower, and a freestanding soaking tub designed for relaxation. With three additional bedrooms, a dedicated office, and 3.5 beautifully appointed bathrooms, this thoughtfully designed single-story home provides nearly 2,500 square feet of flexible living space. Outdoors, your personal retreat awaits. Enjoy year-round Florida living on the covered lanai, complete with a built-in summer kitchen and a custom-designed pool—ideal for hosting or unwinding. The fully fenced yard features new vinyl fencing, fresh sod, and an automated sprinkler system for effortless maintenance. Perfectly positioned near Phelps Park, the Winter Park YMCA, Lakemont Elementary, and an array of top-tier shopping and dining destinations, this home delivers the ideal blend of privacy, craftsmanship, and everyday luxury.

102 Bell Place, Winter Park

$985,000
4 Beds 3 Baths Lakeside Estates SubDv. 32792 Zip Code
Welcome to refined Florida living in the highly sought-after gated community of Lakeside Estates, one of Winter Park’s most exclusive neighborhoods, where homes rarely come to market. With only 39 residences, this intimate lakefront community offers a level of privacy, prestige, and curb appeal that is increasingly difficult to find. From the moment you pass through the impressive gated entrance framed by a beautifully designed pond, elegant stone wall, and striking fountain, you immediately sense that Lakeside Estates is something special. This Mediterranean-inspired residence showcases timeless architectural design with a stunning stone-accented tower entry, graceful arched architecture, and a classic barrel tile roof, all complemented by a beautifully maintained paver driveway and a welcoming 8-foot front door. Inside, thoughtful craftsmanship is evident throughout, with colonial-style crown molding, designer finishes, and wood-look porcelain plank tile flooring that delivers the warmth of hardwood with exceptional durability. At the heart of the home, the chef’s kitchen is designed for both everyday living and entertaining, featuring white shaker cabinetry with crown molding, quartz countertops with elegant marble-inspired veining, stainless steel appliances, and a double oven. A beautifully appointed butler’s pantry with a built-in wine rack enhances both convenience and sophistication. The versatile floor plan includes a dedicated office, four bedrooms, spacious living areas, and generously sized rooms, creating flexibility for modern lifestyles. The primary suite provides a private retreat with spa-inspired features and ample storage. Step outside to your own backyard oasis featuring an enclosed saltwater pool, peaceful water views, and pre-plumbing for a future outdoor kitchen, making this outdoor space ideal for year-round entertaining. A convenient full pool bath provides easy access for guests while enjoying the outdoor living areas. Additional highlights include wall-mounted garage storage, kayak storage, and thoughtful design details throughout. Residents of Lakeside Estates enjoy access to a community dock where fishing and kayaking are possible, along with a playground and beautifully maintained common areas, all supported by an HOA that maintains the entrance and shared spaces. Ideally located in Winter Park and zoned for highly regarded schools, this home offers a rare opportunity to own within a private gated community where availability is limited, and demand remains strong.

1453 Via Sangro Place, Winter Park

$799,000
4 Beds 4 Baths Landings At Hawks Crest SubDv. 32792 Zip Code
Nestled in one of the most sought-after neighborhoods in Winter Park, this exceptional gated residence offers the perfect blend of elegance, comfort, and modern efficiency. Ideally located just five minutes from top-rated private schools, this two-story single-family home is designed for both luxurious living and everyday functionality. Upon entry, you are welcomed by a dramatic grand foyer featuring soaring ceilings of nearly 20 feet, creating an impressive and light-filled living space. The open layout seamlessly connects the main living areas, ideal for entertaining and family gatherings. This thoughtfully designed home features 4 spacious bedrooms and 3.5 bathrooms, including dual primary suites—one conveniently located on the main level and another upstairs—providing flexibility for multi-generational living or guest accommodations. A dedicated private office on the first floor offers the perfect work-from-home environment. Step outside to a beautifully maintained backyard with premium artificial turf, fully fenced for privacy, and a screened rear patio—perfect for relaxing or enjoying Florida’s outdoor lifestyle year-round. Extensively upgraded throughout, the home showcases high-quality finishes with no carpet—featuring elegant flooring and tile across all living areas, along with a solid wood staircase that adds warmth and sophistication. The garage is equally well-appointed with a premium epoxy-coated floor, offering both durability and a clean, polished look. Energy efficiency is a standout feature of this home, equipped with a tankless water heater for on-demand hot water and reduced energy consumption, as well as solar panels that help significantly lower utility costs. This is a rare opportunity to own a meticulously upgraded home in a prime Winter Park location—ideal as a primary residence or a high-potential investment property.

1369 Blue Stem Lane, Winter Park

$795,000
4 Beds 3 Baths Winter Park Pines SubDv. 32792 Zip Code
Welcome to 639 Friar Road, ideally situated on a quiet street in the highly desirable Winter Park Pines neighborhood. This extensively updated residence offers the character of a classic 1960s home with the quality and feel of a 2026 renovation. Major improvements include a new roof, new HVAC system with new ductwork, new panel box, and thoughtfully curated high-end kitchen, bath, and lighting design elements. Original terrazzo flooring has been meticulously restored and polished throughout, preserving the home’s timeless appeal. Featuring four bedrooms, three full baths, the home offers a functional open-concept layout with a desirable split floor plan. Two primary suites, each with private en-suite baths, provide flexibility for multi-generational living or guest accommodations. The property showcases strong curb appeal and continues to impress outdoors with a spacious backyard and an oversized lanai designed for entertaining. Zoned for highly rated Winter Park schools, this home delivers an exceptional blend of style, comfort, and indoor-outdoor living in one of Winter Park’s most established neighborhoods.

639 Friar Road, Winter Park

$425,000
4 Beds 3 Baths Tanglewood Sec 4 SubDv. 32792 Zip Code
***WINTER PARK **** 4 BEDROOMS ****3 BATHROOM **** PAID OFF SOLAR ***** WILL HELP BUYER****METAL ROOF ***1/3 ACRE*** Welcome to 1923 Linden Rd, Winter Park—a well-maintained single-story residence offering space, character, and an exceptional location. Built in 1955, this solid masonry and concrete block home features 4 bedrooms, 3 full bathrooms, and approximately 2,117 heated square feet, with 2,281 total building square feet. Located in the highly desirable area of Winter Park, the home provides convenient access to shopping, dining, parks, and top-rated schools, as well as nearby Park Avenue and downtown Orlando. The interior offers a functional layout with multiple living areas, ideal for both everyday living and entertaining. Original character elements such as plaster interior walls and two fireplaces add warmth and timeless appeal. The centrally located kitchen provides ample workspace and flows seamlessly into the main living areas. Situated on a generous 0.315-acre lot (13,717 sq ft) with approximately 117 feet of frontage and 114 feet of depth, the property offers plenty of room for outdoor enjoyment, future enhancements, or expansion. Additional features include Metal Roof that allows for 20 degrees cool, continuous footing foundation, and package cooling system. A strong opportunity for buyers seeking a well-built home with character, space, and long-term value in a prime location.

1923 Linden Road, Winter Park

$725,000
4 Beds 3 Baths Winter Park Pines Rep SubDv. 32792 Zip Code
Fully reimagined and COMPLETELY RENOVATED AND DESIGNED BY HGTV DESIGNER, this stunning 4-br, 3-ba home in desirable Winter Park Pines sits proudly on a spacious corner lot and offers Modern Luxury with thoughtful, HIGH END UPGRADES throughout. The interior showcases ALL-NEW CABINETRY and QUARTZ COUNTERTOPS, highlighted by a dramatic WATERFALL KITCHEN ISLAND, brand-new appliances including a built-in microwave tucked into a custom pantry cabinet. Every detail has been carefully considered, from new luxury vinyl flooring and interior doors to upgraded closet shelving, sleek bathroom mirrors, and stylish shower enclosures. Sound insulation enhancements in key areas—including the primary suite, bathrooms, and kitchen walls—provide added comfort and privacy, while smart ceiling fans, dimmable lighting, USB charging outlets, and pre-wiring for under-cabinet lighting and wall-mounted TVs bring modern convenience to everyday living. Beyond the interior, the home continues to impress with major system upgrades and durable exterior improvements designed for long-term peace of mind. Enjoy a BRAND NEW ROOF with transferable warranty, updated soffit and fascia, rot-proof siding and porch columns, and new fiberglass exterior doors with built-in blinds. The property also features a new irrigation system, vinyl fencing, and an expansive 3+ car driveway. Behind the walls, everything has been upgraded—including full electrical rewiring with a new 200-amp service, all-new plumbing from underground lines to fixtures, and a high-efficiency HVAC system with new ductwork and insulation for maximum energy savings, making this home truly MOVE-IN READY with no detail overlooked. Seller Motivated!

350 Cornwall Rd, Winter Park

$835,000
4 Beds 4 Baths Meadows At Hawks Crest SubDv. 32792 Zip Code
One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buy-down that reduces the buyer's interest rate and monthly payment.** This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium, state of the art solar system YOU OWN OUTRIGHT, nearly eliminating your cost of electricity. Ask to see the bill. The premium solar system is PAID OFF with a TRANSFERABLE WARRANTY by manufacturer. This off-grid solar system comes with a WHOLE HOUSE BATTERY BACKUP, keeping your lights on when the power goes out. This home already comes wired for electric vehicles with room to expand. Excess power generated is sold back to the power company through the NET METERING program, resulting in credits back to the owners at the end of the year. The solar system also has two power monitoring systems for tracking your energy usage & production, conveniently controlled by your phone and computer. Hawks Crest is your home to community, where residents enjoy gated access into a landscaped resort atmosphere, featuring water fountains throughout, with an abundance of amenities. The clubhouse features a resort pool & kiddie pool, a fitness center, with sidewalks & playgrounds, along with the community’s private dock access to Lake Howell with a canoe/kayak launch. Now imagine, relaxing and enjoying park and pond views from your expansive lanai, soaking in the serene sunsets & manicured landscaping, all from the comfort of your spacious, 4-bedroom 3.5 bath home, including a loft upstairs, all conveniently located just a short distance from the resort clubhouse. Owners can relax and unwind while management handles all landscaping around your home, truly providing you a maintenance-free living lifestyle. Additional upgrades with this home include, commercial grade luxurious vinyl wide-plank flooring, two power monitoring systems, a whole-house water softener & filter system, and two HVAC units, all designed for comfort, convenience, and a very clean home, where you can relax. Nestled in this spacious home, you’ll find 20-foot-high ceilings with awe-inspiring views of the illuminated pond fountain, creating a serene view & relaxing atmosphere you’ll enjoy, even from the kitchen sink. Your chandelier can be lowered 20-feet to the floor for easy maintenance & cleaning, using a winch lift system in the attic.(Rated up to 200 lbs). And even watch the rockets launch at The Cape from the front yard. Uniquely designed, this home was built to withstand extreme weather, featuring a concrete/granite tile roofing system, steel reinforcement, concrete-filled block walls & slab, all anchoring to the foundation, uniquely tying everything together. Meticulously maintained by the owners, this home comes with a complete set of blueprints, along with many photos & videos taken of the home during the building process. Owners even have documents for all equipment & appliances. And the premium solar system comes with a transferable warranty that will keep the lights on when the power is out. This home features a split floor-plan, with a primary bedroom on both the first and second floors. Spanning 2,589 sq.ft., this home offers an additional 540 sq.ft. of screened-in lanai, providing a private outdoor oasis where you’ll find owners enjoying the tranquility of Florida sunsets. Schedule a showing for your buyers today! And…***Remember to see the list of the owners’ upgrades***.

1090 Wildmeadow Run, Winter Park

$439,000
4 Beds 2 Baths Winter Park Forest SubDv. 32792 Zip Code
MAY I TEMPT YOU WITH A POOL? Summer’s delight is yours daily with your own pool! Discover a new dimension of living with this terrific classic ranch style home in desirable Winter Park. Great layout home with tons of potential, wonderful split plan with 4 beds/2 baths and almost 1800sf. Entry leads to living and dining combined space to left and straight ahead to large family room and kitchen. Off kitchen, a convenient breakfast nook area and more views of the pool. Generous primary right off breakfast nook with sliders to the pool and a spacious bath that has a walk in shower with bench and large walk-in closet. Additional 3 nice-sized bedrooms on other side of home, right off the roomy family room that also leads to pool. The 2nd large bath for these bedrooms has tub/shower and double sink vanity. Home has an oversized garage with laundry facilities. Then the POOL…a tranquil spot with huge, covered patio area, pass through from kitchen, overflowing fountain and spa available. The pool and patio areas are all screened in, so great for parties and another Florida style living area. Pocket doors throughout. Home is last on a dead-end street with brick wall on one side for lots of privacy. Large side yard would be great for planting your own garden or dog run. Community has natural gas available. HVAC (2025); Roof (2018); Water Heater-gas (2008). Great Winter Park location, close to shopping, dining, major highways and hospital. Don’t’ wait on this one, it’s a winner! And why pay more for a pool-less home when you can have more fun here!

837 Appalachee Avenue, Winter Park

$649,000
4 Beds 2 Baths Greenview At Winter Pines SubDv. 32792 Zip Code
POOL HOME, nestled along the 14th fairway of Winter Park Pines Golf Course (WP18). A peaceful retreat with no rear neighbors—ideal for tranquility and privacy. Offering 1,936 square feet, four bedrooms, two bathrooms and an inside utility room, this is a hard-to-find gem in Winter Park. Perfectly situated in a tree-lined community overlooking the golf course. Upon entering, you are greeted by a spacious foyer that leads into a formal living room and then transitions into a formal dining area. The updated kitchen includes a cozy breakfast nook. The inviting family room features vaulted ceilings, beams and a fireplace creating a welcoming atmosphere for gatherings and relaxation. The primary suite boasts his-and-her closets, enhancing functionality. This home is zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School. Recent updates include AC (2014), Windows (2020), New Roof (2025), New Electrical Panel (2025), and Re-pipe (2026). WELCOME HOME!

1523 Golfside Drive, Winter Park

$630,000
4 Beds 2 Baths Brookshire Heights 4th Add SubDv. 32792 Zip Code
OPEN HOUSE CANCELED - MULTIPLE OFFERS. Located in the sought-after Brookshire Heights neighborhood, this original-owner Winter Park home sits on a large lot with no HOA and offers the space and flexibility today's buyers are looking for. The split floor plan features 4 bedrooms, 2 bathrooms, and 1,943 square feet of living space filled with natural light throughout. The kitchen is equipped with stainless steel appliances, and the screened porch provides a comfortable outdoor retreat for everyday living or entertaining. A two-car garage and generous lot complete the package. Ideally situated near AdventHealth Winter Park, Crosby Wellness Center, Winter Park Pines Golf Club, Cady Way Trail, Park Avenue, Baldwin Park, and top-rated Winter Park schools, this home delivers an exceptional location with long-term value at appraisal price.

649 Berwick Drive, Winter Park

$600,000
4 Beds 2 Baths Brookshire Heights SubDv. 32792 Zip Code
Completely renovated and move-in ready! This beautifully updated home has been fully remodeled with attention to detail and quality finishes throughout. Recent upgrades include brand-new flooring, modern appliances, fresh interior and exterior paint, and a new A/C system, offering comfort and peace of mind for years to come. The home is in excellent condition. Truly feels like new construction without the new construction price. Perfect for first-time homebuyers looking for a turnkey property or investors seeking a strong rental opportunity in a desirable location. Conveniently located near shopping, dining, major roadways, and top-rated schools. Don’t miss this opportunity to own a fully updated home in a fantastic area!

2330 Coldstream Drive, Winter Park

$685,000
4 Beds 3 Baths Lost Creek SubDv. 32792 Zip Code
Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection to nature. From the moment you arrive, you’ll notice the peaceful ambiance—towering trees, lush greenery, and the soothing backdrop of untouched landscape. Inside, the home features a spacious and inviting layout with approximately 4 bedrooms and 3 bathrooms, designed for both comfortable living and effortless entertaining. Large windows frame picturesque views of the wooded backdrop, filling the home with natural light and bringing the outdoors in. The kitchen flows seamlessly into the main living areas, while the split floor plan offers privacy for the primary suite, complete with tranquil views of the conservation area. Step outside to your backyard oasis where you can unwind, host gatherings, or simply enjoy the sights and sounds of nature along Howell Creek. Opportunities like this are incredibly rare—nearly an acre of protected land, no rear neighbors, and a location just minutes from everything Winter Park has to offer. Experience the perfect balance of privacy, space, and convenience in this truly special home.

3114 Heartleaf Place, Winter Park

$1,495,000
4 Beds 4 Baths The Enclave Winter Park SubDv. 32792 Zip Code
Pre-Construction. To be built. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, blending timeless character with modern luxury. 901 Enclave Place (Lot1) is a thoughtfully designed courtyard home offering an elegant yet functional layout centered around private outdoor living. A charming covered front porch and welcoming foyer lead into an expansive open-concept gathering and dining space, seamlessly connected to a designer kitchen featuring a large center island, walk-in pantry, and effortless flow for entertaining. At the heart of the home, a covered lanai and courtyard create a true indoor-outdoor lifestyle—perfect for year-round enjoyment and intimate gatherings. The first-floor primary suite is a private retreat with a spacious walk-in closet and spa-inspired bath, complemented by a convenient powder bath and laundry/pantry area. Upstairs, you’ll find a well-appointed layout including an second primary suite with a luxurious bath and oversized closet, a additional bedroom, full bath, and a versatile gathering loft—ideal as a media room, office, or flex space. Designed with both comfort and sophistication in mind, this residence showcases clean architectural lines, abundant natural light, and carefully curated indoor and outdoor living spaces. Located within a boutique enclave of just a limited number of homes, residents will enjoy a serene setting surrounded by mature trees and thoughtfully designed community green space. Experience the best of Winter Park living with close proximity to renowned dining, shopping, and top-rated schools—all within one of the area’s most sought-after new communities. Design book is available upon request. Please inquire for details and customization options.

901 Enclave Place, Winter Park

$1,495,000
4 Beds 4 Baths The Enclave Winter Park SubDv. 32792 Zip Code
Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. Ideally located within walking distance to Park Avenue and historic Old Winter Park, this exclusive neighborhood blends timeless character with modern luxury. The courtyard homes at The Enclave offer a distinctive design centered around light, openness, and indoor-outdoor living. These four-bedroom residences feature thoughtfully designed floor plans with a first-floor primary suite and expansive living spaces that flow seamlessly to private outdoor areas. Large windows and two unique entry design options allow for abundant natural light, enhancing the open-concept layouts. Each home is finished with high-end selections, including Wolf and Sub-Zero appliances, high-performance double-pane windows, and elevated interior finishes throughout. Blending modern design with comfort and functionality, these homes provide a unique opportunity to enjoy a private courtyard lifestyle in one of Winter Park’s most desirable locations. Design book is available upon request. Please inquire for details and customization options.

905 Enclave Place, Winter Park

$650,000
4 Beds 3 Baths Meadows At Hawks Crest SubDv. 32792 Zip Code
In the gates of one of Winter Park’s most desirable communities, this elegant single-story residence offers an exceptional opportunity to experience refined Florida living in the sought-after enclave of Hawk’s Crest. Spanning more than 1,700 square feet, the home blends timeless architecture with a thoughtfully designed layout that balances comfort, style and functionality. From the moment you enter, soaring ceilings and expansive windows fill the interior with natural light, creating an inviting and sophisticated atmosphere. Ceramic tile flooring extends throughout the home, offering a clean and cohesive design while providing durability for everyday living. The living and dining areas connect seamlessly, creating an ideal setting for intimate evenings and effortless entertaining. At the center of the home, the kitchen serves as a natural gathering space, thoughtfully designed with style and functionality in mind. It features premium appliances, crisp white cabinetry and a spacious island, all while overlooking the main living areas for a seamless connection throughout the home. Updated lighting throughout the residence adds a refined modern touch and enhances the warm ambiance of the home. The primary suite offers a peaceful retreat, complete with a spacious walk-in closet and a spa-inspired bath designed for relaxation. Additional bedrooms provide flexibility for guests, family or a dedicated office space, each thoughtfully designed with comfort in mind. Outside, beautifully maintained grounds cared for by the HOA allow residents to enjoy the surrounding landscape without responsibility of maintenance. Life in Hawk’s Crest offers a lifestyle that extends far beyond the home itself. Residents enjoy access to resort-inspired amenities, including a swimming pool, clubhouse, fitness center, splash pad, playgrounds, dog park and private access to Lake Howell. The community also hosts popular monthly food truck gatherings and offers everyday convenience of Park Maitland Preschool, Kelly’s Ice Cream and Foxtail Coffee just at the community entrance. Ideally just minutes from Park Avenue’s celebrated dining and shopping, top-rated schools and Winter Park’s cultural destinations, this residence presents an exceptional opportunity to enjoy one of Central Florida’s sought-after lifestyles.

1098 Wildmeadow Run, Winter Park

$449,900
4 Beds 2 Baths Georgetown Estates SubDv. 32792 Zip Code
Welcome to this beautifully remodeled, move-in-ready home in the highly sought-after Winter Park area. This single-story residence features 4 bedrooms and 2 bathrooms, offering a bright, open floor plan with modern finishes designed for both comfort and functionality. A standout feature of this property is its commitment to sustainable living and energy efficiency. Highlights include: - Newer Roof: Installed in 2023 - Radiant Barrier & Blown-In Attic Insulation: Keeps the Florida heat out and significantly lowers cooling costs. - High-Efficiency HVAC: Energy Star rated AC unit ensuring consistent temperatures and peak savings. Step outside to an expansive backyard featuring a private pool, perfect for relaxing or entertaining. This large outdoor space offers endless possibilities for customization, such as a garden or an outdoor kitchen. Located in a quiet, established neighborhood within an A+ rated school zone, this home provides convenient access to top shopping, dining, parks, and major highways. Don't miss this incredible opportunity to own a fully updated turnkey property in one of the most desirable areas of Winter Park.

501 Heritage Boulevard, Winter Park

$430,000
4 Beds 2 Baths Winter Park Estates SubDv. 32792 Zip Code
Updated 4-bedroom, 2-bath home in a premium Winter Park location with NO HOA and a spacious backyard. This home is currently in the final phase of renovation and has already undergone major upgrades, including remodeled bathrooms, updated kitchen, new flooring, upgraded electrical, new AC System and a newer roof. The interior has been thoughtfully modernized, offering a bright open layout ideal for comfortable living and entertaining. The property is being sold in its current condition; exterior improvements will not be completed, giving the future owner the opportunity to finish and customize the exterior to their preference. Conveniently located near shopping, dining, schools, and major roadways.

Winter Park

$487,500
4 Beds 3 Baths Winter Park Pines Merrie Oaks SubDv. 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome to beautiful Winter Park! This spacious 4-bedroom, 3-bathroom home offers 1,864 square feet of living space and sits on a generous lot in an established neighborhood known for its mature trees, convenient location, and classic Florida charm. This home is solid, making it a fantastic opportunity for buyers looking to add their own personal style and make it their own. With great bones and a functional layout, it provides the perfect canvas for someone who wants to create their dream home while enjoying the comfort of a well-kept community. The interior offers ample living space, multiple bedrooms for family or guests, and flexibility for a home office, hobby room, or multi-generational living. The sizable lot provides plenty of room for outdoor entertaining, gardening, or future improvements. Located in the Winter Park Pines, the neighborhood is loved for its quiet residential streets, established homes, and unbeatable convenience. Residents enjoy close proximity to: • Park Avenue and Downtown Winter Park for shopping, dining, and community events • Cady Way Trail and nearby parks for walking, biking, and outdoor recreation • Easy access to Full Sail University, UCF, and Rollins College • Quick commutes to Downtown Orlando, major highways, and Orlando International Airport • Nearby restaurants, coffee shops, and everyday conveniences along Aloma Ave and Semoran Blvd Whether you’re an investor, or someone looking for a home you can truly make it yours, this property offers location, space, and long-term potential in one of Central Florida’s most desirable communities. Don’t miss the chance to make this Winter Park home yours!

275 N Ranger Boulevard, Winter Park