Winter Park Homes with Single Family Property Style

Winter Park Homes with Single Family Property Style

Welcome to Winter Park, Florida—a picturesque city that seamlessly blends charm, culture, and community. Nestled just north of Orlando, Winter Park is renowned for its stunning lakes, lush parks, and vibrant downtown area. With its tree-lined streets and historic architecture, this city offers a serene yet lively atmosphere that appeals to families, retirees, and young professionals alike.

Winter Park is home to a rich tapestry of cultural attractions, including the renowned Charles Hosmer Morse Museum of American Art, which houses the world’s most comprehensive collection of works by Louis Comfort Tiffany. The city also boasts beautiful gardens and scenic parks, such as the lush Mead Botanical Garden, perfect for family outings or peaceful strolls. The Winter Park Farmers' Market, held every Saturday, showcases local produce, artisanal goods, and a warm community spirit that makes this city truly special.

When it comes to housing, Winter Park offers an array of stunning single-family homes that cater to diverse lifestyles. From charming bungalows with classic Florida architecture to modern estates with contemporary finishes, there is something for everyone. The neighborhoods are characterized by their welcoming ambiance and strong sense of community, making it easy to feel at home.

With excellent schools, a plethora of dining options, and easy access to major highways and attractions, Winter Park is not just a place to live—it's a place to thrive. Whether you're looking to settle down or invest, Winter Park's single-family properties present an exceptional opportunity to embrace the quintessential Florida lifestyle. Discover your dream home in this enchanting city today!

Newest Winter Park Homes with Single Family Property Style

$4,750,000
5 Beds ⋅ 5 Baths ⋅ Lake Maitland SubDv. ⋅ 32789 Zip Code
Privately nestled on 1.32 acres (1.1+ acres HIGH & DRY) along the tranquil shores of Lake Temple, this remarkable residence is a true compound where architecture, craftsmanship, and nature exist in perfect balance. Completed in 2019 by Gallimore Homes and enhanced with more than $300K in upgrades, this home was designed to feel secluded and private while serving as the ultimate destination for entertaining. This unique property offers a 4,060+ SF main residence (4 beds / 3.5 baths plus bonus room for a future 5th bedroom), a detached 480+ SF guest house (1 bed / 1 bath), and resort-style outdoor living overlooking peaceful water views and a rolling backyard. Designed for exceptional privacy, the home is positioned well back from the street and buffered by mature landscaping, a private courtyard wall with a security gate, and hurricane-impact windows and doors throughout. Additional highlights include an oversized three-car garage, parking for 15+ vehicles, and space to park a boat or RV next to the conservation area. Inside, soaring ceilings and premium finishes create an immediate sense of warmth and sophistication. Ten-foot-tall EuroWall folding glass doors span 15 feet across the great room, seamlessly blending indoor and outdoor living while framing beautiful backyard and water views. The chef's kitchen showcases professional-grade Sub-Zero and Wolf appliances, an oversized gathering island with prep sink, ice maker, waterfall countertops, a 48-inch Wolf six-burner dual-fuel range, dry bar with refrigerated drawers, and a spacious walk-in pantry. The open-concept design flows effortlessly into the great room and dining area, making everyday living and entertaining equally inviting. The split-bedroom floor plan offers exceptional privacy, highlighted by a spacious first-floor primary suite with 2 walk-in closets (totaling 175+ SF) and a spa-inspired bath. The first floor also includes a guest suite, two additional bedrooms with a Jack-and-Jill bath, and a powder/pool bath with access to the lania. Upstairs, the bonus room provides flexibility for a media room, game room, home office, and pre-plumed for a bath and kitchenette for a future 5th bedroom. Equally impressive is the detached guest house, complete with its own covered front porch, full kitchen, living room, bedroom, full bath, and beautiful backyard views…ideal for multigenerational living, extended guests, a private office, or long-term visitors. The covered lanai was designed for year-round outdoor living with three Phantom Screens spanning nearly 45 feet, an authentic Argentine wood-fired grill, and a built-in wet bar. The heated saltwater infinity-edge pool features a sun shelf, LED lighting, and a composite wood sun deck overlooking the water. The expansive lawn gently slopes to the shoreline beneath a magnificent 100+ year-old oak tree, enhanced by mature landscaping and landscape lighting that creates an unforgettable setting for intimate evenings and large-scale gatherings too. Located less than three miles from Interlachen Country Club and a few blocks from the Winter Park Racquet Club, this property offers a rare combination of privacy, flexibility, and estate-style living on more than an acre of waterfront in Winter Park. (*Ask for a Floorplan, List of Improvements, and Survey. Click the Virtual Tour link to see a video of the property! )

2525 Temple Drive, Winter Park
$675,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated three-bedroom, two-bathroom pool home offering nearly 1,800 square feet of thoughtfully designed living space on a spacious lot backing to a peaceful conservation easement. Featuring separate living and family rooms, a remodeled kitchen, and an exceptional outdoor retreat, this inviting home is perfectly designed for both everyday living and entertaining. From the moment you arrive, the classic brick entry creates a warm first impression. Inside, the flexible floor plan provides plenty of space to gather, relax, work from home, or host guests. Laminate wood flooring and updated baseboards (2022) complement plantation shutters, recessed lighting, and ceiling fans throughout. Multiple storage closets add everyday functionality, while updated windows and French doors fill the home with natural light and seamlessly connect the indoor and outdoor living spaces. The remodeled kitchen (2021) features crisp white shaker cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, an oversized stainless-steel sink, and a breakfast bar with seating for four. A dedicated coffee bar and pantry add convenience, while the large bay window overlooks the pool and private backyard, creating the perfect backdrop for everyday living. The spacious primary suite offers a walk-in closet and ceiling fan. Its ensuite bathroom, renovated in 2022, features large marble-look tile, a double vanity with quartz countertops, and a beautifully updated walk-in shower with a frameless glass enclosure. Two additional guest bedrooms and an updated full bathroom complete the bedroom wing. Step outside to the true centerpiece of the home. Backing to a conservation easement, the backyard offers a peaceful setting with enhanced privacy. The screened, in-ground chlorine pool was completely refreshed in 2025 with new tile, repaired beam, resurfacing, and new pool light. The lanai deck was also resurfaced, creating an ideal space for swimming, outdoor dining, and entertaining family and friends. The outdoor improvements continue with fresh landscaping completed in 2025, including new sod, a stone pathway, French drains for improved drainage, and an updated irrigation timer. The fully fenced backyard (2023) provides additional privacy for pets, play, and gatherings. Ideally located near Cady Way Trail and Winter Park Pines Golf Course, you'll also enjoy convenient access to Cady Way Park amenities, including a community pool, playground, tennis and pickleball courts, beach volleyball, and walking trails. AdventHealth Winter Park and the Crosby Wellness Center are just minutes away, while Rollins College, Full Sail University, UCF, and Orlando International Airport are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines modern updates, flexible living spaces, and a private backyard retreat in one of Winter Park's most desirable locations. ROOF - 2024 ELECTRICAL PANELS - 2021

433 Gilbert Road, Winter Park
$435,000
3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code
This is an Excellent split plan pool home. Tile floors in the Family room, Living Room, and Dining room keep with the Florida syle. The bedrooms feature wood floors in all the bedrooms.The screened in pool is also heated and has a Heated Spa. It is conveniently located in Seminole County with a Winter Park address. It also features a ROOF that is only two years old ! You can cool off in the screened in pool on hot days. During the cooler time of year you can use the Heater for both the pool and Spa.The screen enclosure helps to make the pool more inviting. You also have a covered porch area for entertaining. There is yard space that is fully fenced. The back yard also has a shed for storing your yard tools. SOLD AS IS. Contact the Listing Agent for a personal tour !

3740 Hawthorne Lane, Winter Park
$425,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 06 SubDv. ⋅ 32792 Zip Code
Discover the epitome of comfortable living in this fantastic single-family home situated on a generous and spacious corner lot. This meticulously renovated property features 3 bedrooms and 2 bathrooms, offering a perfect blend of modern style and cozy charm. Step inside to experience the allure of an open floor plan that seamlessly connects the living spaces. The kitchen, fully renovated and boasting a contemporary design, is the heart of this home—a perfect gathering place for family and friends. Indulge in the luxury of a private backyard oasis, where tranquility meets outdoor enjoyment. A delightful retreat awaits with a nice backyard, ideal for entertaining or simply unwinding under the stars. Plus, your vehicles and recreational gear are well taken care of with a 2-car garage and an additional boat space. The charm continues outdoors with a great covered lanai, providing the perfect setting for al fresco dining or cozy evenings by the fireplace. Every detail of this home has been thoughtfully curated to enhance your lifestyle. Don't miss the opportunity to make this Winter Park residence your own—where spacious living, thoughtful design, and comfort converge. Schedule your tour today and envision the possibilities that await in this truly remarkable home!

1886 Clematis Lane, Winter Park
$429,000
4 Beds ⋅ 2 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code
Rare opportunity in Winter Park's 32789! Located on a quiet cul-de-sac in one of Central Florida's most sought-after ZIP codes, this spacious 4-bedroom, 2-bath home offers approximately 2,400 square feet of living space, a brand new roof (2025), water heater (2021), and is situated on a generous lot with no HOA. Whether you're dreaming of creating your forever home, searching for your next renovation project, or looking to add a prime rental property to your portfolio, this is one you won't want to miss. With a little vision and updating, this property can truly shine in a neighborhood where beautifully renovated homes and stunning new construction continue to elevate property values. The location is exceptional—minutes from Park Avenue, Winter Park Village, top-rated schools, Rollins College, AdventHealth, downtown Orlando, and convenient access to I-4 and SR 408. Enjoy some of Central Florida's finest dining, boutique shopping, parks, museums, and entertainment, all just moments from your doorstep. Families will also appreciate Killarney Elementary School is just one street away. With endless possibilities to reimagine, renovate, or invest, opportunities to purchase a home like this seldom come along. If you're looking to build equity, generate rental income, or create the home you've always envisioned, this exceptional property is ready for its next chapter.

2323 Devon Court, Winter Park
$1,419,900
4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
Under Construction. Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by one of the areas finest builders. This stunning new farmhouse-inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and comfort. Step onto the inviting front porch and through the elegant 2 story entryway to discover a spacious, open floor plan filled with natural light. Just off the foyer, you’ll find a flexible fourth bedroom or private study with a full bath—ideal for a home office or serene guest suite. The heart of the home is the gourmet kitchen, featuring quartz countertops, custom cabinetry, and a premium Bosch appliance package including a 36" gas cooktop. The kitchen flows seamlessly into the living and dining areas—perfect for entertaining or family gatherings. Enjoy Florida living at its finest on the covered lanai, overlooking your sparkling pool and lushly landscaped backyard—your own private retreat. The first-floor primary suite offers a spa-inspired bath with dual vanities, a freestanding soaking tub, and a spacious walk-in closet with custom shelving. A convenient laundry area is thoughtfully located just off the suite. Upstairs, a large bonus room with a closet offers versatility as a fifth bedroom, game room, or home office. Two additional bedrooms feature walk-in closets and share a beautifully appointed bath with dual sinks. An upstairs laundry room with a sink and plenty of natural light adds everyday convenience. The photos shown are of the same model in another location. Finishes will vary. Located near top-rated schools, local parks, and all that Winter Park has to offer — this home truly has it all. Schedule your private showing today before this exceptional new build is gone!

1546 Miller Avenue, Winter Park
$430,000
3 Beds ⋅ 2 Baths ⋅ Howell Branch Woods SubDv. ⋅ 32792 Zip Code
Virtually Staged. Discover this spacious 3-bedroom, 2-bathroom home offers 1,483 sq ft of comfortable living space with a functional layout and plenty of room for everyday living. The home features a well-appointed kitchen, open living areas, and generously sized bedrooms. Outside, enjoy a private backyard with a swimming pool, creating the perfect space for relaxing, entertaining, and enjoying the Florida lifestyle.

5409 Albert Drive, Winter Park
$339,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Subd Unit No 05 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated 3-bedroom, 2-bath home in beautiful Winter Park! This move-in-ready property features stylish wood-look tile flooring throughout, creating a seamless, modern look that's both attractive and easy to maintain. The home has two beautifully renovated bathrooms with contemporary finishes, along with a newer A/C and a new roof in 2026. The air-conditioned laundry room has plenty of storage space. Step outside to your spacious, fully fenced backyard, where you'll find plenty of room to entertain, play, or unwind around the cozy fire pit. The generous outdoor space offers endless possibilities for gatherings, gardening, or simply enjoying Florida's beautiful weather. A rare highlight is the oversized swing gate providing convenient side-yard access with ample room to park an RV, boat, trailer, or other recreational vehicles. Best of all, there's no HOA, giving you the freedom to make the most of your property without additional HOA restrictions. Perfectly situated just minutes from Costco, grocery stores, shopping, dining, and the popular Cady Way Trail, this home offers the ideal combination of comfort, convenience, and outdoor recreation. With easy access to major roadways and everything Winter Park has to offer, this home truly has it all. Welcome home!

3562 Bougainvillea Drive, Winter Park
$795,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code
This well-cared-for immaculate home features quality workmanship inside and out! In addition to the three bedroom two bath, there is an 'office-bonus' room. The mature tropical oasis landscaping, cozy seating areas, and winding pathways make you feel right at home and at the same time on vacation! Open Kitchen, dining room, living room and bonus room. Located on a quaint street nestled among custom built homes. Have the best of both worlds, family life with upscale restaurants and shopping, and the annual Art and Holiday Festivals, movies in the park, parades, Rollins College, Boat Tours, kayaking and paddleboarding on the Winter Park Chain of Lakes all linked together and easily accessed via an Italian-inspired canal system. Only a mile away from famous ‘Park Avenue’ where visitors travel from all over the world to experience and celebrate our romantic sidewalk cafés and festivities.

1850 Bryan Avenue, Winter Park
$324,900
3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 03 SubDv. ⋅ 32792 Zip Code
Virtually Staged. Opportunity Awaits in the Heart of Winter Park! Welcome to 7426 Blue Jacket Place, a 3-bedroom, 2-bathroom home that's ready for its next chapter. Nestled on a quiet street in an established neighborhood, this property offers a fantastic opportunity for buyers looking to add their personal touch and create the home of their dreams. Plus, enjoy added peace of mind knowing the roof was replaced approximately six years ago. Inside, you'll find a spacious layout featuring a large living area, a functional kitchen with an adjoining dining space, and generously sized bedrooms. The screened-in porch is the perfect place to relax and enjoy the peaceful backyard. Step outside and discover one of this home's standout features—a beautiful, mature camphor tree that creates a picturesque backyard retreat with plenty of shade and room to garden, entertain, or simply unwind. The property also includes a storage shed, ample outdoor space for endless possibilities, and an existing 25-foot-deep well on the property, offering potential for future use. Conveniently located near shopping, dining, major roadways, parks, and all the highly sought-after Winter Park amenities, this home offers an unbeatable location with tremendous potential. Whether you're a first-time homebuyer, investor, or someone looking for a renovation project, this is an opportunity you won't want to miss. Bring your vision and make 7426 Blue Jacket Place your own!

7426 Blue Jacket Place E, Winter Park
$2,275,000
4 Beds ⋅ 5 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code
This WINTER PARK POOL HOME is set on a corner lot with entrances from both Palmer Avenue and Temple Drive. Located within Winter Park's exclusive J Kronenberger community, this luxury property is tucked away approximately a half mile to Winter Park's YMCA, Phelps Park & the lovely Kraft Azalea Garden, and approximately 1.5 miles to Park Avenue's restaurants, boutiques and farmer's market. The floor plan offers 4 bedrooms, 4.5 bathrooms & a home office/bonus room. The bedrooms are organized in a triple split plan arrangement that frames the open-concept gathering areas. Three bedrooms have private ensuite bathrooms, the 4th bedroom is placed directly next to the hall bath, and the office/bonus room sits adjacent to the guest half bath...everyone has a bathroom! Multiple exits lead out to the backyard, seamlessly merging the indoor and outdoor spaces. Mature hedges provide natural privacy for the open-air pool, spacious pool deck and backyard lawn. Additionally, a backyard paver path provides access to the property's 2-car detached garage. There is plenty of parking for year-round entertaining with the front half circle drive and the rear 2-car garage with multi-car driveway. This home uses natural gas to fuel the range, tankless water heater and outdoor firepit on the pool deck. Recent updates include outdoor perimeter lighting, rear fence, privacy hedges & irrigation. Prime real estate within Winter Park’s historic tree-lined streets.

1271 Palmer Avenue, Winter Park
$469,000
3 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code
Okay, let's talk about this one. Yes, there's green carpet. Yes, it needs your vision. I know exactly what you're thinking right now. But hear me out, because this house has some things going for it that are genuinely hard to find. Start with the location. In under 10 minutes in any direction, you could be having lunch on Park Ave, shopping at Altamonte Mall, or launching your boat up in Maitland. That kind of range is rare in Central Florida, and this spot has it. And there's no HOA here, which if you know, you know. Then there's the pool. A real pool, tucked behind a block wall for total privacy, so you can actually enjoy it without the whole street watching. That kind of setup doesn't come around often. This is a 3 bedroom, 2 bath home with real bones and real space. The layout gives you room to breathe, and the systems that actually matter have already been taken care of. Water heater, brand new in 2026. HVAC, also brand new in 2026. Roof was done in 2025. Plumbing was updated in 2017. So the expensive, unglamorous stuff, the stuff that actually protects your investment, is already handled. The home has been professionally cleaned and pressure washed, so it's not just clean, it's move in ready clean. You could genuinely move in as is and update it slowly, on your own timeline, as your taste and budget allow. No rush. No pressure. Just a solid home with good bones, a pool, an unbeatable location, and all the boring but important stuff already done for you. Sometimes the right house isn't the one that's already finished. It's the one that's ready for you to finish it.

2703 Tierra Circle, Winter Park
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