Winter Park Homes with Other Exterior Features

Winter Park Homes with Other Exterior Features

Winter Park, located in the state of Florida, is a charming city known for its picturesque landscapes, vibrant culture, and rich history. Situated just a few miles north of Orlando, Winter Park offers residents a perfect blend of small-town charm and big-city amenities.

One of the standout features of Winter Park is its diverse range of homes with other exterior features. Whether you're looking for a traditional colonial-style home, a modern architectural masterpiece, or a cozy cottage, Winter Park has it all. True to its name, Winter Park is a haven for outdoor enthusiasts, with many homes featuring beautiful gardens, lush landscaping, and spacious yards.

In addition to the stunning exteriors, Winter Park homes offer a wide range of amenities and features. Many properties boast swimming pools, outdoor entertaining spaces, and private balconies or patios where residents can relax and enjoy the Florida sunshine. Inside, you'll find spacious floor plans, high-end finishes, and luxurious master suites that provide the perfect retreat after a long day.

Beyond the homes themselves, Winter Park offers a plethora of recreational activities, including boating and water sports on the city's numerous lakes, hiking and biking trails, and world-class golf courses. The city also boasts a vibrant arts and culture scene, with museums, galleries, and theaters showcasing local talent.

With its idyllic setting, diverse range of homes, and abundance of amenities, Winter Park is a highly sought-after destination for those seeking a true Florida lifestyle. Whether you're looking for a permanent residence or a vacation home, Winter Park offers a little something for everyone.

Newest Winter Park Homes with Other Exterior Features

5415 N Lake Burkett Lane, Winter Park
$435,000
3 Beds ⋅ 3 Baths ⋅ Trinity Bay Ph 2 SubDv. ⋅ 32792 Zip Code
Welcome to 5415 N Lake Burkett Lane, a beautiful home located in the desirable Trinity Bay community of Winter Park, with a neighborhood boat slip, dock, and lake access! Offering 3 bedrooms, 2.5 bathrooms, and 2,027 square feet of thoughtfully designed living space, this home makes a lasting first impression with its soaring vaulted ceilings and inviting atmosphere. The open, well-designed floorplan creates a natural flow throughout the main living areas, making it perfect for both everyday living and entertaining. The downstairs features spacious living and dining areas, a convenient half bathroom, a dedicated laundry room, and direct access to the attached two-car garage. Upstairs, you'll find all three bedrooms, offering a comfortable separation between the main living spaces and private retreats. The layout provides a wonderful balance of functionality and comfort, with plenty of room to accommodate a variety of lifestyles. Step outside to enjoy the screened-in rear patio, the perfect spot to enjoy your morning coffee or unwind in the evenings while taking in the outdoors. Beyond the patio, you'll find a generously sized backyard with endless possibilities! Whether you envision creating your dream outdoor entertaining space, adding a garden, designing a play area, or simply enjoying the extra room to relax, this backyard is a blank canvas waiting for your personal touch. With its spacious layout, soaring ceilings, and fantastic potential, this Trinity Bay home is an opportunity you won't want to miss!

5415 N Lake Burkett Lane, Winter Park
257 Lincolnshire Road, Winter Park
$550,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Welcome to 257 Lincolnshire Road, a 3-bedroom, 2-bath home offering 1,610 square feet of living space in the established Winter Park Pines neighborhood. Situated at the end of a cul-de-sac street, this single-story home sits on an expansive 0.58-acre lot, providing an inviting setting with room to bring your vision to life. Inside, a spacious living and dining layout features multiple gathering areas, large windows that welcome natural light, and a distinctive brick fireplace with wood-paneled detailing. The kitchen offers generous cabinet storage, a breakfast bar, and an open connection to the main living area. An attached two-car garage adds everyday convenience. Sliding glass doors open to a covered, screened-in patio overlooking the oversized backyard. With over 200 feet of rear property line, this expansive outdoor space offers remarkable flexibility for entertaining, gardening, recreation, or designing your own outdoor retreat. Mature trees and natural greenery create a welcoming backdrop with plenty of room to enjoy. Whether you envision renovating and personalizing the existing home or starting fresh by removing the current structure and building a new residence, this expansive property offers the flexibility to explore a variety of possibilities. Enjoy the appeal of an established neighborhood with the golf course just down the street and convenient access to Aloma Avenue. With its generous lot, cul-de-sac setting, and Winter Park location, this property is ready for your ideas.

257 Lincolnshire Road, Winter Park
808 Densmore Drive, Winter Park
$509,999
3 Beds ⋅ 2 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code
Welcome to 808 Densmore Drive, a beautifully updated 3-bedroom, 2-bathroom pool home tucked into the established Winter Park Estates neighborhood! Blending modern farmhouse charm with thoughtful upgrades, this home offers 1,460 square feet of inviting living space designed for both everyday comfort and entertaining. Step inside to a bright, open floor plan where the spacious living and dining areas flow effortlessly into the kitchen, complete with quartz countertops, stainless steel appliances, a built-in microwave, tile backsplash, and a window overlooking the outdoors. On the opposite side of the home, you'll find three comfortable bedrooms and two beautifully updated bathrooms, offering a practical layout with plenty of privacy. An oversized interior laundry room and enclosed porch provide additional functional space. Outside is where this home truly shines! The private backyard features a sparkling in-ground pool, a newly installed paver patio (2025), and a brand-new fence (2026), creating an inviting setting for weekend gatherings, outdoor dining, or relaxing in the Florida sunshine. Recent improvements also include a new irrigation system and control panel (2026), updated pool filtration equipment (2026), and a water heater replaced approximately three years ago. Beyond the property, enjoy a prime Winter Park location just minutes from Cady Way Trail, Winter Park Pines Golf Course, Rollins College, and the shopping, dining, and charm of Park Avenue. With its updated interiors, private pool, and convenient access to everything Winter Park has to offer, 808 Densmore Drive is ready to welcome you home!

808 Densmore Drive, Winter Park
4786 Tangerine Avenue Unit 4786, Winter Park
$220,000
2 Beds ⋅ 2 Baths ⋅ Wrenwood Condo SubDv. ⋅ 32792 Zip Code
Discover comfort, style, and convenience in the heart of Winter Park! This beautifully updated 2-bedroom, 1.5-bathroom, two-story condominium offers approximately 1,281 square feet of living space with a spacious, functional layout designed for everyday living and entertaining. Step inside to find ceramic tile flooring, an inviting living and dining area, and a beautifully appointed kitchen featuring granite countertops, attractive cabinetry, a stylish backsplash, and stainless steel appliances. Upstairs, you'll find two generously sized bedrooms, including a primary bedroom with a walk-in closet. Enjoy your morning coffee or unwind in the evening on the private screened-in porch overlooking a peaceful green space, complete with an additional storage closet. Interior laundry adds everyday convenience. Located in the established Wrenwood condominium community, residents enjoy access to a community swimming pool and clubhouse. The property also offers two assigned parking spaces and convenient access to major roads, shopping, restaurants, and entertainment. LOCATION, LOCATION, LOCATION! Just minutes from Full Sail University, UCF, Rollins College, Downtown Winter Park, and the popular Park Avenue shopping and dining district. Whether you're searching for your primary residence or an investment opportunity, this property offers an appealing combination of location, space, and convenience. Don't miss this opportunity to own a condominium in desirable Winter Park! Schedule your private showing today!

4786 Tangerine Avenue Unit 4786, Winter Park
188 Sandlewood Unit 1, Winter Park
$290,000
2 Beds ⋅ 3 Baths ⋅ Sandlewood Creek Condo SubDv. ⋅ 32789 Zip Code
Welcome home to 188 Sandelwood Trail, a beautifully updated 2-bedroom, 2-full-bath residence in the heart of Winter Park. Thoughtfully refreshed and move-in ready, this home blends modern comfort with the charm and convenience that make Winter Park one of Central Florida's most sought-after addresses. Stylish wood-look flooring flows throughout the inviting living room, where a wood-burning fireplace creates a warm, welcoming focal point for relaxing evenings or entertaining friends. The updated kitchen shines with granite countertops and stainless steel appliances, combining function and style for everyday cooking. The primary suite is a true retreat, with serene views overlooking the sparkling pool and a private en-suite bath. The second bedroom and full bath adds flexibility for guests, a home office, or hobby space. Enjoy an unbeatable location just minutes from Park Avenue's boutique shopping and dining, lakes, parks, and cultural attractions, with easy access to major roadways for a convenient commute throughout the Orlando metro. Whether you're a first-time buyer, downsizing, or seeking a low-maintenance lifestyle, this Winter Park gem checks every box. Schedule your private showing today!

188 Sandlewood Unit 1, Winter Park
712 Baffie Avenue, Winter Park
$419,900
3 Beds ⋅ 1 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code
Welcome to 712 Baffie Avenue, a charming and thoughtfully updated bungalow in one of Winter Park’s most sought-after areas. This home blends classic character with modern improvements, featuring beautiful hardwood floors, crown molding, a fireplace, and plenty of natural light throughout. The bright enclosed Florida room provides flexible space for a home office, sitting area, playroom, or additional entertaining space. The updated kitchen offers dark cabinetry, stone countertops, stainless steel appliances, and contemporary finishes. Major improvements include a brand-new roof installed in 2026, along with updated electrical, plumbing, and HVAC systems completed in 2025. These recent improvements provide added value and peace of mind for the next owner. The interior laundry room adds everyday convenience, while the covered rear porch creates a comfortable place to relax and enjoy the outdoors. The fenced backyard offers room for entertaining, gardening, pets, or creating a private outdoor retreat. Enjoy a prime location near A-rated schools, Dubsdread Golf Course, College Park, downtown Winter Park, AdventHealth, shopping, dining, and major roadways. With no HOA and easy access to some of Central Florida’s most popular neighborhoods, this home delivers the character, location, and major updates that make it stand out.

712 Baffie Avenue, Winter Park
173 Scottsdale Square Unit 173, Winter Park
$100,000
1 Beds ⋅ 1 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
INVESTMENT OPPORTUNITY! Add this well-maintained condo to your investment portfolio or make it your next income-producing property. Featuring a functional layout, neutral finishes, easy-care flooring, stainless-steel appliances, and plenty of natural light, this unit offers an attractive and low-maintenance option for investors. The comfortable living area flows to the outdoor space through sliding glass doors, creating a bright and inviting atmosphere. Conveniently located near shopping, dining, major roadways, and everyday necessities. Whether you're expanding your rental portfolio or looking for your next investment opportunity, this condo is worth a look. Schedule your showing today!

173 Scottsdale Square Unit 173, Winter Park
2463 Grand Teton Circle Unit 2463, Winter Park
$249,000
3 Beds ⋅ 3 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Virtually Staged. Don't miss this incredible opportunity in one of Winter Park's most desirable locations! This spacious 2-story condo offers over 1,700 square feet of living space, featuring an open floor plan that's perfect for everyday living and entertaining. A dedicated office space adds flexibility for remote work or a home study a rare find at this price point. While the home could use some updating, the bones and layout make this a fantastic canvas to add your personal touch and build instant equity. Currently occupied by a great tenant, this property is a perfect turnkey opportunity for investors looking to add a cash-flowing asset to their portfolio, or for buyers ready to move in once the lease ends on June 2027. With its unbeatable location near Winter Parks shopping, dining, and entertainment, this is the kind of opportunity that won't last long at $249,000. Don't miss this and make your appointment today!

2463 Grand Teton Circle Unit 2463, Winter Park
2275 Island Run, Winter Park
$279,999
3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code
Great opportunity in the established Windward Square community of Winter Park! This END-UNIT home offers 3 bedrooms, 2 full bathrooms and approximately 1,467 square feet of living space, with added privacy and plenty of potential. ROOF REPLACED IN 2017! 10K seller contribution for the floor. The home is ready for some TLC and personal updates, giving the next owner the opportunity to renovate and make it their own. The spacious living and dining areas gives a functional layout, while the large screened porch provides additional space to relax, entertain, and enjoy Florida living. Being located at the end provides additional privacy and a more open feel compared with interior units. The community offers amenities including a swimming pool and tennis courts. Conveniently located near shopping, dining and major roadways, with easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this property offers great potential and an excellent opportunity to add value through your own improvements. Bring your vision and make this home your own!

2275 Island Run, Winter Park
2181 Linden Road, Winter Park
$419,990
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
7525 Lodge Pole Trail, Winter Park
$550,000
4 Beds ⋅ 2 Baths ⋅ Arrowhead Cove SubDv. ⋅ 32792 Zip Code
WOW! Now offered at $25,000 less, this fully renovated Winter Park POOL home pairs move-in-ready style with an expansive .36-acre lot! With FOUR bedrooms, TWO updated bathrooms and nearly 2,000 square feet, you’ll enjoy a beautifully renovated kitchen, a split floor plan and a screened lanai overlooking your private pool—all ready for your next chapter in the established Arrowhead Cove Neighborhood!This home was thoughtfully renovated throughout, this move-in-ready residence combines modern finishes, an ideal SPLIT FLOOR PLAN and exceptional outdoor living with a location zoned for top-rated Winter Park schools. Inside, ALL brand-NEW WINDOWS AND SLIDERS, installed in 2026, fill the home with natural light while wood laminate flooring, fresh interior paint, and recessed lighting create a polished, comfortable atmosphere. The RENOVATED 2025 KITCHEN features crisp white shaker-style cabinetry, quartz countertops, brand-new stainless steel appliances and a spacious stainless sink, creating a stylish and functional centerpiece for everyday living and entertaining. The private primary suite is thoughtfully separated from the secondary bedrooms and offers dual built-in closets and a FULLY RENOVATED ensuite BATHROOM with a double quartz vanity, beautifully tiled shower and separate water closet. Three additional bedrooms share a FULLY RENOVATED hall bathroom featuring a double quartz vanity, tiled tub/shower and convenient direct access to the pool area. Step outside to your own private backyard retreat, where a spacious screened LANAI overlooks the sparkling in-ground POOL. Resurfaced in 2025, the chlorine-generated pool also features a NEW PUMP, LIGHT, steps and filter. A separate GAZEBO provides another inviting space for outdoor dining or relaxing, while the FULLY FENCED oversized .36-acre pie-shaped lot offers plenty of room to enjoy the outdoors. A TWO-CAR garage adds everyday convenience and storage. Ideally located just FIVE minutes from Full Sail University and SR 417, approximately 15 minutes to UCF and 20 minutes to Orlando International Airport, this exceptional home also offers easy access to Target, Costco, grocery stores and abundant retail. Only 15 minutes from Downtown Winter Park luxury dining and shopping. With extensive 2025-2026 renovations, a private pool and an oversized lot in a highly desirable Winter Park school zone, this is a rare opportunity to enjoy turnkey living in a prime Central Florida location. ROOF - 2023 HVAC - 2018 PLUMBING - 2025 WATER HEATER - 2017

7525 Lodge Pole Trail, Winter Park
720 Pansy Avenue, Winter Park
$1,295,000
3 Beds ⋅ 4 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code
Welcome to 720 Pansy Ave, a distinctive three-story Winter Park home thoughtfully designed for both everyday living and flexible use. Fully remodeled in 2017, the residence offers a clean, contemporary interior with LVP and tile flooring, recessed lighting, crisp finishes, and an open flow through the main living spaces. The first floor includes a spacious living room, dining area, and a separate office/study/den, providing plenty of room to work, gather, and unwind. At the heart of the home, the modern kitchen features sleek white cabinetry, stainless steel appliances, generous storage, and a wide pass-through that keeps the kitchen connected to the dining and living areas. The first-floor primary suite offers the convenience of main-level living, complete with a walk-in closet and a beautifully finished primary bath featuring a steam shower. Large windows bring natural light into the home, while the neutral finishes create an easy backdrop for a variety of styles. Upstairs, two additional bedrooms are joined by flexible spaces that add to the home’s functionality, including a dedicated storage room on the second floor. Continue to the third level to find an expansive bonus space that can easily serve as a media room, game room, creative studio, home gym, or additional lounge. Practical features include a durable metal roof and a whole-house generator designed to keep the home powered during storms and unexpected outages, providing added comfort and peace of mind. Outside, the private backyard extends the living space with decking, a hot tub, landscaped green space, mature trees, and a gazebo for relaxing or entertaining. The location completes the package, placing you in the heart of the Winter Park lifestyle with convenient access to Park Avenue, known for its boutiques, restaurants, cultural attractions, and community events, as well as nearby Rollins College. Enjoy the character and charm of an established Winter Park neighborhood while remaining close to the shopping, dining, arts, and everyday conveniences that make this area such a desirable place to call home.

720 Pansy Avenue, Winter Park
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