Winter Park Homes with Private Yard Exterior Features

Winter Park Homes with Private Yard Exterior Features

Welcome to Winter Park, Florida—a picturesque city that perfectly blends small-town charm with urban sophistication. Nestled just north of Orlando, Winter Park is renowned for its scenic lakes, lush parks, and vibrant arts scene. With its tree-lined streets and historic architecture, this enchanting community offers a delightful escape from the hustle and bustle of city life, all while providing easy access to Orlando's attractions.

One of the standout features of Winter Park is its commitment to preserving the natural beauty of the area. Residents can enjoy a plethora of outdoor activities, from boating on the serene lakes to strolling through the stunning Harry P. Leu Gardens. The city's vibrant downtown district boasts a variety of boutique shops, gourmet restaurants, and cultural venues, including the renowned Charles Hosmer Morse Museum of American Art, home to an impressive collection of Tiffany glass.

For those seeking a home in this idyllic setting, Winter Park offers a range of properties, many of which feature private yards that provide a perfect retreat for relaxation and recreation. Imagine sipping your morning coffee in your own tranquil oasis or hosting summer barbecues in a spacious backyard surrounded by lush landscaping. These homes with private yard exterior features not only enhance your living experience but also offer ample space for family gatherings, gardening, or simply enjoying the Florida sunshine.

Whether you’re drawn to Winter Park for its vibrant community or its stunning natural surroundings, this charming city has something for everyone. Discover your dream home today and experience the allure of Winter Park living!

Newest Winter Park Homes with Private Yard Exterior Features

$675,000
4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code
Nestled on a tranquil, tree-lined street in the vibrant heart of Winter Park, this reimagined 1960s mid-century modern pool residence beautifully harmonizes timeless architectural soul with stylized contemporary updates. Bathed in glorious natural sunlight, the open-concept interior unfolds beneath soaring vaulted ceilings, where durable wood-look flooring flows seamlessly across expansive living and dining spaces. At the center of it all lies a true chef’s haven—an exquisitely updated kitchen equipped with solid wood cabinetry, rich granite countertops, a sprawling prep island, sleek stainless steel appliances, and a bold over-range hood. Thoughtfully arranged along a private bedroom wing, the four spacious bedrooms blend exceptional comfort with versatile living spaces. The fourth bedroom is framed by views of the sun-drenched pool deck—an inspiring backdrop for a home office, creative sanctuary, or private gym. The primary retreat serves as a peaceful haven, complete with an elegant ensuite bath showcasing custom tile work and a glowing vanity mirror. Step through the doors into your own fully fenced tropical oasis, where quintessential Florida living takes center stage. Spend your afternoons lounging beside the sparkling swimming pool, entertaining guests from the custom Tiki bar, or relaxing with a cool drink under the shade of the gazebo surrounded by fresh, plush, mature landscaping and fresh sod. Modern convenience and major infrastructure upgrades ensure total peace of mind, featuring updated plumbing, electrical, and windows, along with a brand-new 2026 HVAC heat pump system (complete with a 10-year warranty) and a 2026 water heater. Complete with a two-car carport, dual storage rooms, indoor laundry, and a well-water irrigation system, every practical detail has been addressed. All of this is situated within top-tier school zones (Brookshire, Glenridge, and Winter Park High), just moments from the boutique shopping and dining on Park Avenue, Rollins College, Baldwin Park, Cady Way Trail, medical hubs, and the energy of downtown Orlando.

2215 Woodcrest Drive, Winter Park
$1,579,000
4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Under Construction. UNDER CONSTRUCTION | LUXURY NEW BUILD | Presented by LUIH Luxury Homes Welcome to 2417 Chantilly Avenue, an exceptional luxury new construction residence in beautiful Winter Park, Florida, where sophisticated design, elevated finishes, and effortless indoor-outdoor living come together. This stunning 4-bedroom, 3.5-bath home features an expansive open-concept floor plan enhanced by upgraded luxury finishes and engineered hardwood flooring throughout. At the heart of the home, the chef-inspired kitchen is designed to impress with premium Thermador appliances, an oversized island, beautiful cabinetry, generous prep space, and a seamless connection to the main living and entertaining areas. The first-floor primary suite offers a private retreat with direct access to the backyard and pool, creating a tranquil connection to the home's outdoor spaces. Step outside and discover your own private oasis. The beautifully designed backyard features a sparkling pool and summer kitchen, providing the perfect setting for entertaining, dining al fresco, or simply relaxing in the Florida sunshine. With 4 bedrooms, 3.5 baths, sophisticated finishes, an open and inviting layout, and exceptional indoor-outdoor living, 2417 Chantilly Avenue delivers the elevated lifestyle today's luxury buyer is looking for—all in one of Winter Park's most desirable locations.

2417 Chantilly Avenue, Winter Park
$2,195,000
4 Beds ⋅ 5 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code
Set on a generous corner lot, this stunning single-story pool home in Winter Park has been beautifully remodeled and offers the kind of effortless, one-level living that's genuinely hard to find. Step through the foyer and the floor plan flows naturally into the gourmet kitchen, through the open family and living spaces, past a flexible home office/den, and out to the backyard, where multiple exits blur the line between indoor and outdoor living. The kitchen is anchored by a substantial island with breakfast bar seating, while a Thermador natural gas cooktop takes center stage, complemented by stainless steel appliances, solid wood cabinetry, a wine refrigerator, and granite countertops — a space equally suited to quiet mornings or full-scale entertaining. The home offers 4 bedrooms, 4.5 bathrooms, and a home office/bonus room, thoughtfully organized in a triple split plan that frames the open-concept gathering areas. Three bedrooms enjoy private en-suite baths, the fourth sits directly beside the hall bath, and the office/bonus room is adjacent to the guest half bath — everyone has a bathroom of their own. The primary suite offers its own private retreat, complete with a luxurious en-suite bath and a spacious walk-in closet appointed with custom built-ins. Outside, a custom inground pool and spacious patio are framed by mature hedges for true backyard privacy, while natural gas fuels an outdoor firepit for evenings well past sunset. Recent updates include outdoor perimeter lighting, a rear fence, privacy hedges, and irrigation. All of this sits on a 0.34-acre lot, with a gracious circular drive off Palmer Avenue for guests and a separate garage and driveway entrance off Temple Drive for everyday comings and goings. A paver path connects the home to its 2-car detached garage, with ample additional parking between the front circular drive and rear driveway — perfect for year-round entertaining. Just moments from Phelps Park, the Winter Park Racquet Club, and the historic beauty of Kraft Azalea Garden, with the shops, restaurants, and farmer's market of Park Avenue close at hand — this is single-story Winter Park living at its very best.

1271 Palmer Avenue, Winter Park
$170,000
2 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 02 SubDv. ⋅ 32792 Zip Code
Terrific townhome in the Hidden Oaks community featuring an updated interior and its own private, fenced patio! Step inside to a bright and spacious living/dining area with beautiful wood laminate flooring and a convenient wet bar. The galley-style kitchen includes a breakfast area, along with a laundry closet equipped with a full-size washer and dryer. Upstairs, you'll find two spacious bedrooms, including one with an oversized walk-in closet. Additional storage is available under the stairs and in the A/C closet. The monthly condo fee includes water, sewer, trash, exterior maintenance, grounds maintenance, and community amenities! Enjoy community amenities, including a refreshing pool! Conveniently located just off Goldenrod Rd, with easy access to E Colonial, 408, and 417 for a quick commute and nearby everyday conveniences. Full Sail University is just 1.8 miles away, Valencia College is 4.5 miles away, and UCF is only 6.2 miles away!

7476 Woodburn Court Unit 38, Winter Park
$5,195,900
5 Beds ⋅ 7 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. A rare convergence of timeless French Country architecture, brand-new custom construction, and coveted access to the Winter Park Chain of Lakes. Thoughtfully designed and being built by FG Schaub Custom Homes, this exceptional property offers the character of a timeless estate with the amenities and craftsmanship expected in a luxury new construction home. The residence will feature five bedrooms, a dedicated office, five full bathrooms, and two half bathrooms, with beautifully appointed living spaces designed for both refined entertaining and comfortable everyday living. The striking exterior showcases classic French Country influences, stone accents, decorative brick detailing, crisp stucco, expansive windows, and multiple gabled rooflines, creating an elegant and welcoming architectural presence. Outdoor living is equally impressive, with a private pool and spa, covered outdoor living area with roll away screens, and a full summer kitchen creating a resort-style retreat. A brand-new private boathouse, included with the property, is positioned directly on the canal and provides access to the Winter Park Chain of Lakes, offering the opportunity to enjoy boating, water sports, fishing, and so much more. Final plans, specifications and finishes are subject to change.

825 Palmer Avenue, Winter Park
$3,750,000
4 Beds ⋅ 3 Baths ⋅ Acreage & Unrec SubDv. ⋅ 32792 Zip Code
Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in one special property. Set behind a private gated entrance on approximately 4.3 total acres, with roughly half of the property consisting of dry land and the balance extending into Lake Howell, this remarkable estate offers a rare combination of privacy, space, and direct lake access, yet remains just minutes from the charm of Park Avenue, Interlachen Country Club, shopping, dining, and everything Winter Park has to offer. Lake Howell provides a spectacular backdrop for everyday living and entertaining, with opportunities for boating, fishing, water sports, sunset cruises, and unforgettable days on the water. The property features its own private boat ramp, boathouse, and boat dock, making lake life exceptionally convenient. The grounds are designed for both grand entertaining and relaxed family living. A massive detached barn offers an incredible flexible space for private events, parties, gatherings, game nights, or simply creating your own ultimate entertainment venue. Fully air conditioned and featuring high ceilings, the barn provides room for additional vehicles, RVs, boats, recreational equipment, and more. It also includes a private gym and bathroom, making it a versatile addition to the property. For RV enthusiasts, the property features a full 50 amp RV hookup with water and sewer hookups. The property is Agriculture zoned and allows horses. A separate four-car detached garage with workshop provides substantial storage and workspace. A generator adds convenience and peace of mind. The expansive fenced grounds offer plenty of room for family, pets, recreation, and outdoor activities, including a large playset and a firepit with comfortable seating—the perfect setting for cool evenings, roasting marshmallows, sharing stories, and making memories together. The recently updated pool area is designed to feel like your own private resort. Enjoy the covered lanai, outdoor kitchen, pool, and stunning lake views, along with a gas fireplace that creates an inviting atmosphere for evening entertaining. The outdoor kitchen is a chef’s dream, making it easy to host everything from casual family gatherings to unforgettable waterfront celebrations. Inside, the home was thoughtfully renovated in 2016 and offers just over 3,377 square feet under air, with approximately 7,758 total square feet. Beautiful wood flooring, tile, and carpeted bedrooms create a comfortable blend of style and functionality. The Florida room provides the perfect place to relax, take in the lake views, and enjoy the natural beauty surrounding the home. The upgraded kitchen features stainless steel appliances and a Thermador range, while the spacious executive office provides an ideal work-from-home environment or private study. The residence offers four bedrooms and three bathrooms, providing generous accommodations for family and guests. With multiple indoor and outdoor gathering spaces, extraordinary storage, recreational amenities, and direct access to Lake Howell, this property is much more than a home—it is a private lifestyle estate. Whether you're looking for a peaceful waterfront sanctuary, a place to entertain on a grand scale, a family compound, or simply a rare piece of Winter Park property with exceptional lake access, this property delivers an unparalleled opportunity.

2622 Lake Howell Lane, Winter Park
$586,567
5 Beds ⋅ 3 Baths ⋅ Attilio G Panacciones Sub SubDv. ⋅ 32789 Zip Code
SOVERA Realty is gifting the buyer a one-year home warranty! Discover a versatile investment opportunity in desirable Winter Park. This duplex offers a combined five bedrooms and three bathrooms across two well-appointed residences. Unit A features two bedrooms and one bathroom, luxury vinyl flooring, tile flooring in the kitchen, and ceiling fans throughout. Unit B provides ample living space with three bedrooms and two bathrooms, luxury vinyl plank and tile flooring, and ceiling fans throughout. Unit B is currently tenant occupied through October, offering immediate rental-income potential. Seller currently occupies Unit A and may consider a post-closing leaseback arrangement with the buyer. Terms are subject to mutual written agreement. All existing appliances, including the washer and dryer, convey with the sale. Conveniently located near Winter Park shopping, dining, entertainment, and major roadways, this property offers an appealing opportunity for investors or future owner-occupants.

1421 Michigan Avenue, Winter Park
$725,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code
Tucked beneath mature oak trees, 1850 Bryan Avenue is a well-maintained home offering comfortable single-story living in Winter Park. Natural light and warm wood floors flow through the inviting living and dining spaces, while a flexible bonus room is well suited for a home office, den or creative space. The kitchen features wood cabinetry and ample counter space. The spacious primary suite offers a private retreat. Additional features include an indoor laundry room and an attached two-car garage. Outside, the fenced yard provides a peaceful setting for gardening, entertaining or relaxing beneath the trees. With shopping, dining, parks and other Winter Park amenities nearby, this home brings together character, comfort and a desirable location.

1850 Bryan Avenue, Winter Park
$1,900,000
4 Beds ⋅ 4 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code
Set along a charming, tree-lined street in Winter Park, this stunning new construction home brings together modern farmhouse character, thoughtfully designed interiors, and an exceptional outdoor living experience. Inside, a dedicated home office just off the entry provides a private and convenient workspace. Beyond, the main living area serves as the heart of the home, where a custom entertainment wall with built-in LED underlighting and an electric fireplace creates a striking focal point. Pocketing sliders open completely to the covered lanai, extending the living space outdoors and creating an effortless setting for entertaining. The kitchen is equally impressive, featuring Taj Mahal quartzite countertops, abundant cabinetry, a full suite of Thermador appliances, and a walk-in pantry. A spacious formal dining area provides plenty of room for larger gatherings while remaining connected to the main living spaces. The primary suite offers a private retreat with his and hers walk-in closets and a beautifully appointed spa-inspired bath. Dual vanities, a freestanding soaking tub, and an oversized walk-in shower create a space designed for both luxury and functionality. Upstairs, a generous bonus room provides flexibility for an additional lounge, media room, or playroom, while a conveniently located laundry room adds to the home’s thoughtful layout. Outside is where this residence truly distinguishes itself. The backyard is centered around a spacious pool with a water feature, creating a private setting for relaxing and entertaining. An expansive covered lanai provides a seamless extension of the interior living areas, while a detached cabana with a full summer kitchen and built-in grill creates a destination of its own overlooking the pool. The location is every bit as compelling. Just a short golf cart ride from Park Avenue, the boutiques, acclaimed restaurants, cafés, and energy of downtown Winter Park are always within easy reach. Phelps Park, Interlachen Country Club, and the YMCA are also just minutes away. With an exceptional outdoor living experience, and a location that places the best of Winter Park close at hand, this home delivers the lifestyle so many come to Winter Park to find.

1702 Arbor Park Drive, Winter Park
$995,999
4 Beds ⋅ 3 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Exceptional Winter Park Opportunity with In-Law Suite & Income Potential Discover the opportunity to own a versatile property in one of Central Florida’s most desirable locations. 471 Holt Ave. in Winter Park offers buyers something increasingly valuable: flexibility. With a private in-law suite, this property presents an exciting opportunity for multigenerational living, a guest suite, home office, or potential rental income. For homeowners, the additional living space provides the freedom to accommodate family members or guests while maintaining privacy and separation. For investors, the configuration creates the potential to generate supplemental income, subject to applicable local regulations and requirements. The property’s location adds to its appeal, placing you near Winter Park’s renowned dining, shopping, parks, cultural attractions, and vibrant community amenities. Also, just a short distance to Rollins College! Whether you’re looking to offset your mortgage, create an additional income stream, or simply secure a property with adaptable living options, this home offers a compelling combination of lifestyle and investment potential. Opportunities with this level of flexibility are hard to find. Live in the main residence, utilize the suite for family or guests, or explore its income-producing potential. 471 Holt Ave. offers the versatility today’s buyers are looking for and the potential long-term value investors appreciate. Don’t miss the opportunity to make this flexible Winter Park property your next home or investment.

471 Holt Avenue, Winter Park
$1,950,000
3 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code
Set along one of Winter Park’s charming brick streets just steps from Park Avenue, this beautifully maintained home pairs refined design with an exceptional location. Impressive curb appeal sets the tone, while thoughtfully curated interiors create a home that feels both elevated and inviting. Inside, the main living space centers around a custom entertainment wall with built-in shelving and an electric fireplace. The adjoining kitchen is equally impressive, featuring quartz countertops, a statement La Cornue range, paneled refrigerator, and a cleverly hidden walk-in pantry. A sun-filled breakfast nook provides a casual dining space, while sliding glass doors create a seamless connection to the outdoor living areas. For larger gatherings, the spacious formal dining room offers an elegant setting for entertaining, and a well-designed mudroom and laundry combination adds everyday functionality. The primary suite is a private retreat with generous proportions and a beautifully appointed spa-inspired bath. A custom trough-style sink, separate makeup vanity, oversized walk-in shower, freestanding soaking tub, and expansive walk-in closet create a space that feels luxurious yet highly functional. Two additional bedrooms are both ensuite, offering privacy and comfort for family and guests. Outdoors, the home truly impresses. A lush wall of mature bamboo surrounds the backyard, creating an unexpected sense of privacy just moments from the heart of Winter Park. The resort-style pool features a sun shelf and built-in seating, while a pergola provides the perfect setting for al fresco dining and relaxed evenings outdoors. For the car enthusiast there is a car lift in the garage allowing for storage of up to 3 vehicles. The location is difficult to match, just steps from the shops, restaurants, and energy of Park Avenue and minutes from Hannibal Square, Winter Park Village, Park Maitland School, and the Enzian Theater. Beautifully maintained, thoughtfully designed, and positioned in one of Winter Park’s most desirable locations, this is a rare opportunity to enjoy an exceptional lifestyle in the heart of it all.

751 Pansy Avenue, Winter Park
$450,000
5 Beds ⋅ 3 Baths ⋅ Ridge High 1st Add SubDv. ⋅ 32792 Zip Code
Welcome to 2181 Linden Road, where modern updates meet the everyday convenience of Winter Park living. Thoughtfully renovated and designed with flexibility in mind, this home offers a versatile layout, contemporary finishes, and a private separate-entry suite that adds valuable space for guests, a home office, or additional living arrangements. With no HOA, the property offers added flexibility rarely found in this sought-after area. The location is a standout. Enjoy easy access to Winter Park’s renowned Park Avenue, with its boutiques, restaurants, cafés, galleries, and local events, while nearby Winter Park Village adds even more shopping, dining, entertainment, and everyday conveniences. Outdoor enthusiasts will appreciate close access to the Cross Seminole Trail, Lake Baldwin Park, the Winter Park Chain of Lakes, scenic parks, and recreational opportunities. Downtown Orlando, major employment centers, Advent Health Winter Park, Rollins College, Full Sail University, SR-436, SR-426, and I-4 are also conveniently accessible. Winter Park continues to invest in its future, with ongoing improvements to Park Avenue, expanded infrastructure and streetscape enhancements, and a citywide Parks & Recreation Master Plan focused on improving parks, trails, open spaces, recreation, and community facilities for years to come. This is more than a renovated home it is an opportunity to enjoy the lifestyle, connectivity, character, and continued growth that make Winter Park one of Central Florida’s most desirable places to call home.

2181 Linden Road, Winter Park
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