Winter Park Homes with Tennis Court(s) Amenities

Winter Park Homes with Tennis Court(s) Amenities

Welcome to Winter Park, Florida – a picturesque city that perfectly blends small-town charm with modern sophistication. Nestled just north of Orlando, Winter Park is renowned for its beautiful tree-lined streets, stunning parks, and a vibrant arts scene. With its rich history, unique boutiques, and delightful eateries, this city is a haven for those seeking a serene yet engaging lifestyle.

One of the standout features of Winter Park is its commitment to outdoor recreation, and what better way to enjoy the Florida sunshine than with a home that boasts its very own tennis court? Properties in this charming city with tennis court amenities offer a unique lifestyle opportunity for both seasoned players and casual enthusiasts alike. Imagine stepping out your back door to practice your serve or host friendly matches with family and friends, all within the privacy of your own home.

These homes not only provide recreational benefits but also foster a sense of community. Neighbors can come together for weekend tournaments or simply enjoy the game while soaking in the beautiful Florida weather. Additionally, many of these properties are situated near Winter Park's numerous parks and recreational facilities, allowing for a balanced lifestyle that embraces both relaxation and activity.

Whether you’re looking to invest in a family home or a luxurious retreat, Winter Park’s real estate market offers a range of stunning properties equipped with tennis courts. Experience the joy of living in a city that values both leisure and culture, and let Winter Park be the backdrop for your next chapter. Your dream home awaits!

Newest Winter Park Homes with Tennis Court(s) Amenities

3 Beds ⋅ 2 Baths ⋅ Windward Square SubDv. ⋅ 32792 Zip Code

All play and no work! This beautifully maintained 3-bedroom, 2-bath townhouse offers the perfect combination of comfort, convenience, low HOA fees, and an unbeatable Winter Park location. Whether you're a first-time homebuyer, downsizing, or looking for a low-maintenance lifestyle, this home checks all the boxes. Step inside to discover a bright, open floor plan highlighted by vaulted ceilings and dramatic clerestory windows that flood the home with natural light. The thoughtfully designed split-bedroom floor plan provides added privacy, while the spacious primary suite features a walk-in closet and sliding glass doors leading to your own private, fenced backyard. The kitchen offers a comfortable eat-in dining area, abundant cabinet space, and an oversized pantry for exceptional storage. An enclosed laundry room adds everyday convenience, while recent updates provide peace of mind, including a brand-new roof (2026), newer A/C, updated plumbing, updated electrical panels, and fresh interior paint. Step outside to your covered patio with a convenient storage closet, overlooking a fully fenced backyard—the perfect place to relax, entertain, or enjoy your morning coffee. With low HOA fees, you'll also enjoy outstanding community amenities, including three swimming pools, tennis courts, a playground, a clubhouse, and a private south gate providing quick and convenient access in and out of the community. Ideally located just minutes from Downtown Winter Park, you'll love being close to Park Avenue, shopping, dining, entertainment, top-rated schools, and major highways, making commuting throughout Central Florida quick and convenient. If you've been searching for an affordable, move-in-ready home with major system updates, fantastic amenities, low HOA fees, and an exceptional Winter Park location, this is the one you've been waiting for. Schedule your private showing today!

2653 Cayman Way, Winter Park

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

2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code

Turnkey Living in the Heart of Winter Park! Welcome to this beautifully maintained 2-bedroom, 2-bath townhome offering the perfect blend of comfort, convenience, and low-maintenance living. Vacant and move-in ready, this home has been freshly painted and features a recently replaced air conditioning system, providing peace of mind for its next owner. Inside, you'll find a thoughtfully designed floor plan with spacious living and dining areas, a well-appointed kitchen, and two generously sized bedrooms and bathrooms designed for comfort and functionality. Whether you're relaxing at home or entertaining friends and family, this inviting layout makes everyday living effortless. Step outside and enjoy the exceptional community amenities, including a sparkling swimming pool and tennis courts, perfect for enjoying Florida's year-round sunshine. Whether you're a first-time homebuyer, downsizing, seeking a second home, or looking for an investment opportunity, this property offers incredible versatility. Ideally located in desirable Winter Park, you'll be just minutes from shopping, dining, entertainment, major highways, UCF, Full Sail University, Downtown Winter Park, and Downtown Orlando, making commuting and enjoying Central Florida's best attractions a breeze. Don't miss your opportunity to own this beautifully updated, turnkey home in one of Central Florida's most sought-after communities! All room measurements, HOA information, square footage, and property details are deemed reliable but not guaranteed and should be independently verified by the buyer and buyer's agent.

2475 Tahoe Circle Unit 2475, Winter Park

3 Beds ⋅ 3 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code

Welcome to 2433 Grand Teton Circle in the sought-after Cedarwood Village community of Winter Park, where move-in ready living, thoughtful updates, and an unbeatable location come together. Featuring the largest floor plan in the community, this spacious condo has been refreshed with brand-new carpet and fresh interior paint, offering a bright, inviting space that’s ready for its next owner. The highly desirable layout includes a first-floor primary suite, making everyday living both comfortable and convenient. Inside, you’ll love the soaring vaulted ceilings that create an open, airy feel, while the wood-burning fireplace serves as the focal point of the living room, adding warmth and character. Just off the primary suite, a private front patio provides the perfect place to enjoy your morning coffee or unwind in the evening. A dedicated storage room offers additional space for seasonal décor, bicycles, and outdoor equipment. Cedarwood Village is known for its low-maintenance lifestyle, with the HOA maintaining the grounds and completing roof and exterior paint replacements approximately five years ago. Residents also enjoy access to a community pool, clubhouse, tennis courts, pickleball courts and guest parking. Location is one of this home’s greatest features. Ideally situated near Downtown Winter Park, Park Avenue, Winter Park Village, Baldwin Park, Full Sail University, Rollins College, Valencia College, and the University of Central Florida (UCF), you’ll enjoy convenient access to some of Central Florida’s best shopping, dining, entertainment, and recreation. Commuting is easy with nearby Howell Branch Road, Semoran Boulevard (SR 436), Aloma Avenue (SR 426), 417, and I4, providing quick access to Downtown Orlando, Maitland, Lake Mary, AdventHealth Winter Park, and Orlando International Airport. Located within the Seminole County Public School district, this home offers both convenience and an exceptional Winter Park address. Whether you’re searching for a primary residence, a low-maintenance home, or a spacious Winter Park condo in one of Central Florida’s most convenient locations, 2433 Grand Teton Circle offers the perfect combination of space, comfort, and lifestyle.

2433 Grand Teton Circle, Winter Park

2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code

Beautifully renovated 2 bedroom, 2 bathroom condo at 2305 Sun Valley in Winter Park, offering a fresh modern design and thoughtful updates throughout. The fully redesigned kitchen features sleek cabinetry, quartz countertops, GE stainless steel appliances, a marble tile backsplash, abundant storage, recessed lighting, and a clean open feel that connects seamlessly to the main living areas. Wood-look porcelain tile flooring runs throughout the home, creating a cohesive, attractive, and low-maintenance finish. The spacious living area features vaulted ceilings, skylights, updated ceiling fans, and sliding glass doors that fill the space with natural light and lead to a covered screened patio overlooking green space. The primary suite includes an updated double vanity and a beautifully redesigned bathroom with a separate tub and newly installed shower. The second bathroom also offers an updated vanity and clean neutral finishes. Additional highlights include a 2021 AC, 2021 water heater, updated fixtures, generous natural light, and a screened outdoor living space ideal for relaxing and enjoying Florida’s indoor-outdoor lifestyle. This move-in ready Winter Park condo combines modern style, comfort, and everyday functionality. Residents enjoy access to a sparkling community pool, clubhouse, tennis and pickleball, and a pet walk with waste stations. Monthly fees also include roof and exterior building maintenance, exterior pest control, and landscaping, adding convenience and long-term value.The location is hard to beat, just minutes from Park Avenue, UCF, Rollins College, Full Sail University, shopping, dining, entertainment, and nearby medical facilities.

2305 Sun Valley Cir, Winter Park, Fl 32792, Winter Park

2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated condo, ideally nestled between Winter Park and Maitland. This inviting home features a versatile upstairs loft overlooking the living and dining areas—perfect for a home office, fitness space, craft room, or additional guest accommodations. The bright, cheerful eat-in kitchen is both stylish and functional, showcasing quartz countertops, a glass tile backsplash, abundant cabinetry, a pull-out spice rack, trash/recycling cabinet, and a built-in storage unit. Sliding glass doors open to the private front courtyard, filling the space with natural light. Conveniently located laundry area, complete with washer and dryer, is tucked within the kitchen. The spacious living room features a cozy wood-burning fireplace and flows seamlessly into the dining area beneath soaring vaulted ceilings accented by skylights. Sliding glass doors lead to a screened lanai with a slate tile floor and a storage closet—an ideal spot to relax and enjoy Florida living. The primary suite also opens directly to the lanai and offers a beautifully renovated en-suite bath with a luxurious walk-in shower, updated vanity, linen cabinet, and a custom walk-in closet with built-in organizers. The front bedroom also includes a generous walk-in closet. Enjoy added privacy with a picturesque, tree-lined green space across the street rather than neighboring condos directly in front. Two dedicated parking spaces are conveniently located just outside your door. Cedarwood Village offers an exceptional location directly across from Casselberry Commons Shopping Plaza and is just minutes from Full Sail University, UCF, and Rollins College. Residents enjoy a community swimming pool, tennis courts with pickleball lines, and designated dog-walking areas. Additional highlights include a new roof and skylights installed in 2020. Monthly HOA fees cover exterior maintenance, lawn care, and community amenities, making this the perfect opportunity to enjoy carefree living in one of the area's most desirable communities.

2372 Sun Valley Circle Unit 2372, Winter Park

3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code

Enjoy abundant natural light throughout this beautifully maintained one-story, 3-bedroom, 2-bath home, enhanced by soaring vaulted ceilings and an inviting open layout. The kitchen features natural wood cabinetry, stainless steel appliances, and a charming breakfast nook with access to the front patio. The spacious primary suite offers a walk-in closet and private access to the patio. A desirable split-bedroom floor plan provides added privacy, with two guest bedrooms and a full guest bath situated at the front of the home. The bright and versatile patio can be accessed from both the living room and primary suite, creating the perfect space to relax, entertain, or enjoy year-round Florida living. Roof 2023, A/C 2020, Water Heater 2020, pex piping upgrades include pavered driveway, bathrooms updated, patio doors updated, and vinyl fencing in backyard.

2339 Inagua Way, Winter Park

3 Beds ⋅ 2 Baths ⋅ Country Lane SubDv. ⋅ 32792 Zip Code

Discover this well maintained 3 bedroom, 2 bathroom home offering 1,676 sq ft of comfortable living space. The home features a spacious layout with inviting living and dining areas that flow seamlessly into the kitchen, creating a great setup for everyday living and entertaining. The primary suite includes a private bathroom and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to your own private backyard retreat featuring a pool and fully fenced yard, perfect for relaxing, entertaining, and enjoying the Florida lifestyle. Located in a quiet residential neighborhood, this move-in ready home is easy to show and ready for its next owner.

1535 Lawndale Circle, Winter Park

2 Beds ⋅ 3 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code

Welcome to 193 Lewfield Cir, Winter Park, FL 32792, a spacious two-story end-unit townhome offering 2 bedrooms, 2.5 bathrooms, and 1,300 square feet of comfortable living space in the Stratford A Winter Park Condo community. This 2-bed townhouse in Winter Park features an open floorplan with a large living and dining area, updated wood-look flooring throughout the main living spaces and bedrooms, recessed lighting, ceiling fans, and sliding glass doors that bring in natural light. The kitchen offers ample cabinet storage, stainless steel appliances, tile flooring, and a functional pass-through breakfast bar that opens to the main living area, creating a seamless layout for everyday living and entertaining. Upstairs, the oversized primary suite includes a walk-in closet, private en-suite bathroom, and generous floor space, while the secondary bedroom also features wood-look flooring, natural light, and easy access to the second full bathroom. Additional highlights include inside laundry, updated lighting fixtures, open parking, and plenty of storage throughout. Residents enjoy access to community amenities including a pool, fitness center, tennis courts, sidewalks, and maintained grounds, with HOA dues covering water, exterior maintenance, recreational facilities, and grounds maintenance. Conveniently located near Howell Branch Rd and SR 436, this Winter Park townhome provides quick access to shopping, dining, Downtown Winter Park, Maitland, Full Sail University, UCF, and Downtown Orlando. Located near highly rated Seminole County schools, parks, restaurants, and everyday conveniences, this property offers low maintenance living in a well-connected Central Florida location.

193 Lewfield Circle, Winter Park

3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code

Virtually Staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from the boutiques, dining, and charm of Park Avenue. This unique 4th floor residence offers an exceptional combination of space, privacy, and potential. Featuring 3 bedrooms and 2 bathrooms, the expansive floor plan has been enlarged by enclosing two patios, creating generous living spaces rarely found in condominium living. Vaulted ceilings, skylights, and abundant natural light enhance the open, airy feel throughout the home, while the top-floor location provides remarkable tranquility and privacy. The spacious kitchen offers ample counter space, a breakfast bar, and excellent cabinet space, while the living area is anchored by a fireplace — another uncommon feature in condo living. Large bedrooms, a sizable in-unit laundry room with extensive storage, and an oversized attic provide an extraordinary amount of storage seldom seen in comparable properties. The primary suite features vaulted ceilings, a walk-in closet, and a spacious bathroom layout. For maximum flexibility, the second bedroom, featuring a bright Sun Room alcove, connects to the primary bedroom so it could also be utilized as a private den. Recent unit improvements include a NEW HVAC system, a NEW Water Heater, and Plumbing updates. A reserved covered parking space is included, along with plentiful guest parking for visitors. Residents of Park West enjoy a secure gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements completed. Association fees include water, sewer, and trash service, creating a truly low-maintenance “lock-and-leave” lifestyle ideal for travelers or seasonal residents. While this condo presents an exciting opportunity for personalization, the location, floor plan, and features make this an exceptional offering with tremendous potential. Opportunities in Park West are exceedingly rare — this is your chance to create something truly special in the heart of Winter Park.

300 Carolina Avenue Unit 402C, Winter Park

2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code

This charming one story condo is located in the desirable Cedarwood Village. This unique home boasts an open layout that is different from many others in the community. The home showcases engineered hardwood floors, skylights and wonderful natural light. The kitchen provides ample cabinet space, granite counters, built-in wine rack and beautiful custom tile work. The kitchen overlooks the dining and living room combo. The living room has 2 skylights and flows right into the delightful Florida room. The Florida room boasts wonderful built-in shelving and a glass door giving access to the backyard. The primary bedroom showcases wonderful built-in cabinets, 2 closets and an ensuite bathroom with a granite counter vanity. The primary bedroom also looks into the Florida room but can be shut off for privacy with a sliding door. The second bedroom is at the front of the home and has access to the guest bathroom with a granite counter vanity. Two assigned parking spaces are directly in front of the home. To top it all off, this home is in close proximity to several restaurants and shops and is an easy drive to downtown Winter Park.

2503 Tahoe Circle Unit 2503, Winter Park

2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code

Nestled in a peaceful setting within the serene Cedarwood Village community, this charming one-story Winter Park condo offers a quiet retreat away from traffic noise, with a rear wooden fence for no visible neighbors for added privacy. The spacious 27-foot tiled and enclosed lanai creates the perfect place to relax and enjoy the tranquil surroundings. Cedarwood Village also offers low-maintenance living, with lawn care included in the HOA, along with amenities such as rebuilt tennis courts, a recently remodeled pool, a clubhouse, dog-walking areas, and newly paved roads. Conveniently located in a highly rated school district and close to shopping, dining, and entertainment, the property is also just minutes from Full Sail University, Valencia College, and UCF. Inside, the condo is beautifully updated and shows the care of meticulous owners. The modern kitchen features granite countertops, matching cabinetry, and an eat-in area with sliding doors leading to the private patio, while the bathrooms and dining room wet bar are finished with the same stylish cabinets and granite. The split floor plan includes tile flooring throughout the main living areas and wood floors in the bedrooms. The large living and dining spaces feature vaulted ceilings with skylights for abundant natural light, along with a cozy wood-burning fireplace. French doors from the living room open to the enclosed lanai, while the primary suite also has direct lanai access, ample closet space, and a private bath with both a tub and shower. Additional features include an interior laundry closet adjacent to the kitchen, updated plumbing, a roof replaced in 2018, and new ductwork installed in 2023. Two assigned parking spaces are located directly in front of the unit.

2383 Sun Valley Circle Unit 2383, Winter Park

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