Winter Park Homes with Attached Property Description

Winter Park Homes with Attached Property Description

Welcome to Winter Park, Florida—a picturesque gem nestled just north of Orlando, known for its charming brick streets, lush parks, and vibrant cultural scene. This enchanting city boasts a rich history, with stunning architecture that reflects its past, including the iconic Casa Feliz and the beautiful Rollins College campus. Winter Park is renowned for its scenic lakes, including the stunning Lake Osceola, where residents can enjoy leisurely strolls or paddleboarding on sunny afternoons.

As you explore the real estate options in Winter Park, you’ll find a delightful array of homes with attached properties, perfect for families, professionals, and retirees alike. These residences offer the perfect blend of comfort and convenience, often featuring spacious layouts and modern amenities. Many homes come with beautifully landscaped yards, providing a serene outdoor space for relaxation and entertaining.

Living in Winter Park means you’re never far from the action. The city is home to a vibrant arts community, with galleries, theaters, and the renowned Winter Park Sidewalk Art Festival. Enjoy a day of shopping at Park Avenue, where you’ll find boutique stores, delightful cafes, and exquisite dining options. With excellent schools, abundant recreational activities, and a strong sense of community, Winter Park is not just a place to live, but a lifestyle to embrace.

Whether you’re searching for a cozy family home or a stylish retreat, Winter Park’s real estate market has something for everyone. Come and discover the charm and beauty of this delightful city—your dream home awaits!

Newest Winter Park Homes with Attached Property Description

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
216 Lewfield Cir Unit 216, Winter Park
$230,000
3 Beds ⋅ 2 Baths ⋅ Stratford A Winter Park Condominium SubDv. ⋅ 32792 Zip Code
Rare Find - 3 BR/2 BA - 2nd Floor CONDO at The Stratford a Winter Park Condominium! Spacious Living Room accesses 2nd Floor Balcony with a gorgeous view of one (1) of the sparkling community pools. Balcony features additional outside storage room. Dining/Breakfast Nook adjacent to Living Room & Kitchen. Kitchen features refrigerator, electric range, dishwasher, microwave, garbage disposal, pantry, and laundry closet with stackable washer/dryer. Nice sized bedrooms, see attached floor plan. Primary Suite features walk in closet, walk in shower and tile flooring. Guest Bath features tub & shower and tile flooring. Unit conveniently located at back of community by both community pools and tennis courts. Lovely shady, treed community with sidewalks, Clubhouse, two (2) Pools, BBQ areas, and Tennis Court. HOA Fees Cover: trash removal, water, internet only, amenities maintenance, landscaping, and roof. Community Docs and 2026 Budget available for review. Conveniently located to shopping, parks, restaurants, and major transportation routes. Property sold "AS IS", it won't last long!

216 Lewfield Cir Unit 216, Winter Park
700 Melrose Avenue Unit M23, Winter Park
$354,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
Virtually Staged. Winter Park living, with a view you’ll actually want to come home to! This spacious 2-bedroom, 2-bath condo at Winter Park Gardens is clean and puts you in the middle of it all while giving you a peaceful place to escape. Set on the second floor with elevator access, the home overlooks the community pool and lush mature gardens, giving the living spaces a beautiful green backdrop. Step inside, to your open living area, flooded with natural light. The Florida room adds an extra spot to relax with a good book, work from home, or enjoy your morning coffee, with updated windows bringing in plenty of natural light while helping to keep cooling costs low. Fresh interior paint gives the home a clean, updated feel and an easy canvas for your own style. Just outside your door, Winter Park Gardens offers beautifully landscaped grounds, a community pool, pond, and lighted walking paths. Then there's the location. Walk or bike ride to Park Avenue's restaurants, shopping, and boutiques, the Winter Park Tennis Center, Rollins College, and Mead Botanical Garden. This is a great opportunity to enjoy the lock and go Winter Park lifestyle without giving up space, convenience, or a little peace and quiet. Call to schedule your showing today!

700 Melrose Avenue Unit M23, Winter Park
7498 Aloma Pines Court, Winter Park
$355,000
3 Beds ⋅ 3 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code
Welcome to beautiful Winter Park. This Townhome in Gated Aloma Trails has been meticulosly maintained. With an open and spacious floor plan is great for family activities and entertaining. NEW HV/AC AND NEW WATER HEATER. kitchen features all stainless steel appliances, large island great for prep with seating for "4" or more on the oposite side. The large slider leads out to your 5' X 11" private lani, allows natural light to fill the entire space. There is a first floor powder room for convenience for you and your guest. Second floor laundry closet for your convenience. Your oversize primary bedroom features a spacious walk-in closet and ensuite with large vanity and double sinks. There are "2" additional guest bedrooms. The home has a one car garage with an extended pad for a second car. the NEW water heater is located in the garage. The A/C is also NEW. Aloma Trails is convenient to shopping directly accross the street from the complex. minutes from Aloma (426), 417, UCF, Full Sail, Rollins, a Park Ave., Airport and Beaches. SELLER IS MOTIVATED

7498 Aloma Pines Court, Winter Park
1602 Alabama Drive Unit 107, Winter Park
$1,150,000
2 Beds ⋅ 2 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code
Experience timeless lakefront living at The Alabama, one of Winter Park’s most distinctive and treasured residences. Set on more than five gated acres along the Winter Park Chain of Lakes, this beautifully appointed 2-bedroom, 2-bath condominium offers an exceptional blend of elegance, privacy and effortless living. Inside, soaring 11-foot ceilings and 7.5-inch plank white oak flooring create a light and refined atmosphere. The beautifully designed kitchen features Viking and Fisher & Paykel appliances, marble countertops and generous cabinetry, flowing seamlessly into the great room where expansive windows frame picturesque views of Lake Maitland. The serene primary suite is a private retreat with lake views, custom closet built-ins and an elegant marble bath. The guest suite opens to an extraordinary 400-square-foot private terrace with gated access—one of only five private patios within the community. It is an exceptional setting for morning coffee, intimate entertaining or simply enjoying the lush surroundings. Residents enjoy beautifully manicured grounds, a sparkling pool, fitness center and clubhouse, along with an on-site manager, climate-controlled storage, bike and scooter storage, ample guest parking and one deeded covered parking space. A new roof was completed in 2026, and boat slips are available on a first-come, first-served basis. Small pets are welcome; rentals are not permitted. From morning coffee overlooking the lake to spectacular sunsets over Lake Maitland, this is a rare opportunity to experience the beauty, history and understated elegance of lakefront living in Winter Park.

1602 Alabama Drive Unit 107, Winter Park
3302 Royal Street, Winter Park
$269,900
3 Beds ⋅ 2 Baths ⋅ Coronation Add SubDv. ⋅ 32792 Zip Code
Come see this 3 bedroom 2 bath split plan home. All tile throughout home. Granite kitchen countertops. Eat in area in kitchen. Kitchen bar opens to great room. Huge corner lot great for handyman with trailer, boat, RV or truck to park in backyard. Easy access to add on garage in backyard. Cathedral ceilings great room. NO HOA.

3302 Royal Street, Winter Park
2183 Crandon Avenue, Winter Park
$469,000
4 Beds ⋅ 2 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code
Income Producing Duplex in Winter Park, Florida! Great investment opportunity in a desirable location! This duplex features two 2-bedroom, 1-bath units, each approximately 600 square feet, with private entrances, central AC, and a private screened patio area. Both units are currently leased, providing established rental income and long-term occupancy. Each unit offers a spacious living area and a functional kitchen, with a shared laundry room equipped with a washer and dryer for added convenience. Both units include a full bath with updated showers. Enjoy all of Downtown Winter Park, including the shops and restaurants along Park Avenue, Winter Park Village, and an abundance of entertainment and recreational options such as Mead Botanical Garden, Winter Park Tennis Center, Winter Park Golf Course, and much more. The property also offers easy access to major highways and is just minutes from Rollins College. Don't miss this opportunity to own an income-producing property in one of Central Florida's most desirable areas with no HOA. Pictures were taken prior to occupancy.

2183 Crandon Avenue, Winter Park
7450 Wynnewood Square Unit 189, Winter Park
$170,000
2 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 10 SubDv. ⋅ 32792 Zip Code
***Price Improvement*** This charming 2-bedroom, 2.5-bathroom townhome style condo offers the perfect blend of comfort and convenience. Enjoy the peace of mind that comes with a new AC (2025), a new roof (2021), newer water heater (2019) and new refrigerator and dishwasher ensuring your home is both energy-efficient and well-maintained. The entire first floor features ceramic tile, while the upstairs boasts beautiful laminate wood flooring—no carpet here! Both bedrooms are located upstairs, each with its own ensuite bathroom and additional storage above the mirrors. Downstairs, you'll find ample space for entertaining or simply relaxing, enhanced by the convenience of a wet bar. Located just minutes from UCF and Full Sail University, this condo is perfect for anyone looking to enjoy the vibrant local community without the long commute! With shopping, dining, and recreational activities nearby, you'll have everything you need right at your fingertips. Don’t miss out on this fantastic opportunity—schedule a showing today!

7450 Wynnewood Square Unit 189, Winter Park
300 Carolina Avenue Unit 402C, Winter Park
$650,000
3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code
EXCEPTIONAL ELEGANCE & VALUE IN DOWNTOWN WINTER PARK now for JUST $650,000! This spacious 3-bedroom, 2-bath top-floor residence in the coveted PARK WEST community presents a rare opportunity to enjoy the best of Winter Park living just one block from Park Avenue. This residence offers an impressive combination of generous living space, architectural character, privacy, and an unbeatable location. Situated on the fourth floor, this distinctive condo features vaulted ceilings, skylights, and abundant natural light, creating an open and airy atmosphere throughout. Expanded living areas provide flexibility for entertaining, relaxing, or working from home. The inviting living room features a fireplace, while the spacious kitchen offers ample cabinetry, generous counter space, and a convenient breakfast bar. The thoughtfully designed floor plan includes three generously sized bedrooms, including a primary suite with vaulted ceilings, a walk-in closet, and a spacious bathroom. The second bedroom features a charming sunroom alcove and can connect to the primary suite, offering the flexibility of a private den, sitting room, or home office. Storage is exceptional, with a large IN-UNIT laundry room and an oversized attic — features rarely found in condominium living. Recent improvements include a NEW HVAC system, NEW water heater, and plumbing updates, providing added peace of mind. A reserved covered parking space and plentiful guest parking add everyday convenience. Beyond the residence, Park West offers a gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements. Association fees also include sewer and trash service, making this an appealing low-maintenance, lock-and-leave lifestyle! And the location is truly extraordinary! Enjoy the freedom to stroll to Park Avenue's acclaimed restaurants, boutiques, sidewalk cafés, museums, and year-round events, all just moments from your front door. With its spacious three-bedroom floor plan, top-floor privacy, and exceptional storage, this is an outstanding opportunity to enjoy downtown Winter Park living at a compelling value!

300 Carolina Avenue Unit 402C, Winter Park
901 Enclave Place, Winter Park
$1,550,000
4 Beds ⋅ 4 Baths ⋅ The Enclave Winter Park SubDv. ⋅ 32792 Zip Code
Under Construction. Under Construction Buyer Incentive Limited time - Choose from $30,000.00 cash credit or $40,000 credit towards upgrades. 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
905 Enclave Place, Winter Park
$1,550,000
4 Beds ⋅ 4 Baths ⋅ The Enclave Winter Park SubDv. ⋅ 32792 Zip Code
Under Construction. Under Construction Buyer Incentive Limited time - Choose from $30,000.00 cash credit or $40,000 credit towards upgrades.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, 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
311 E Morse Boulevard Unit 7-11, Winter Park
$279,000
1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code
Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue! Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to offer. Located on the second floor, this spacious studio boasts an updated kitchenette, generous storage, and abundant natural light. Enjoy secure garage access, mail and package delivery to your door, and a relaxing retreat with sunrise views, osprey sightings, and even rocket launches visible from the community patios. Community Amenities: Sparkling pool, Club room for social gatherings, Peaceful outdoor patios overlooking Lake Osceola and Professional on-site management. Location Highlights include being one block to Park Avenue’s boutiques, cafes, and fine dining. Close to The Alfond Inn, museums, and galleries. Walkable to SunRail & Amtrak station. Moments from the Winter Park Farmers’ Market. This is a rare opportunity to own a stylish, low-maintenance home in the heart of downtown Winter Park where ELECTRIC, GAS, WATER, SEWER and TRASH are included in condo fee. Whether you're looking for a weekend retreat or full-time residence, this pied-à-terre is truly one-of-a-kind. Call today for your private viewing of this condo.

311 E Morse Boulevard Unit 7-11, Winter Park
Start Your Search

How much is your home worth?

Get instant property value now!