Winter Park Homes with Pool Amenities

Winter Park Homes with Pool Amenities

Welcome to Winter Park, Florida – a charming city known for its picturesque landscapes, vibrant culture, and a lifestyle that seamlessly blends relaxation with sophistication. Nestled just north of Orlando, Winter Park is renowned for its stunning lakes, lush parks, and an array of boutique shops and gourmet dining options. The city’s rich history is reflected in its beautiful architecture, particularly in the historic district where brick-lined streets invite leisurely strolls.

One of the most enticing features of Winter Park is its exceptional selection of homes, many of which come with luxurious pool amenities. Imagine stepping into your own private oasis right in your backyard, where you can unwind and soak up the Florida sun. Homes with pool amenities in Winter Park offer the perfect blend of comfort and leisure, making them ideal for families, retirees, or anyone who loves to entertain. Whether you're hosting summer barbecues or enjoying tranquil evenings by the water, a pool adds an element of luxury to everyday living.

Additionally, the proximity to top-rated schools, beautiful parks, and cultural attractions like the Charles Hosmer Morse Museum of American Art and the Winter Park Farmers’ Market enhances the appeal of this delightful city. With a community that values both nature and the arts, Winter Park is not just a place to live; it’s a lifestyle to embrace. Explore the stunning homes with pool amenities here, and discover your dream oasis in this enchanting Floridian paradise!

Newest Winter Park Homes with Pool Amenities

1 Beds ⋅ 1 Baths ⋅ Golfside Villas Condo SubDv. ⋅ 32792 Zip Code

Virtually Staged. ***Welcome to this exceptionally well-maintained 1-bedroom, 1-bathroom condominium ideally located in Winter Park! Lovingly cared for by its longtime owner, this home offers a wonderful combination of comfort, functionality, and convenience. *WASHER AND DRYER LOCATED IN UNIT* Inside, you'll find a spacious, thoughtfully designed layout featuring a generous living area, an oversized bedroom, and a large bathroom. The charming kitchen offers ample cabinet and counter space, creating an inviting space for both everyday living and entertaining. Step outside to your private balcony, the perfect place to enjoy your morning coffee or relax at the end of the day. The home's separate exterior entrance adds an extra level of convenience and privacy. Enjoy low-maintenance living with HOA dues that cover water, trash, exterior maintenance, and roof replacement. The community recently completed a roof replacement, providing added peace of mind for the new owner. Residents also enjoy access to the community pool, perfect for cooling off on warm Florida days. Conveniently located near UCF, Valencia College, Waterford Lakes Town Center, Orlando International Airport, major highways including SR 408 and SR 417, shopping, dining, and entertainment, this home is also zoned for highly desirable schools. Whether you're a first-time homebuyer, someone looking to downsize, or an investor seeking a well-maintained property in a prime East Orlando location, this condominium offers an outstanding opportunity. Schedule your private showing today!

1000 S Semoran Boulevard Unit 302, 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

1 Beds ⋅ 1 Baths ⋅ Golfside Villas Condo SubDv. ⋅ 32792 Zip Code

Freshly Updated 1-Bedroom Condo – Perfect for Homeowners or Investors! Whether you're looking for your first home, downsizing, or adding to your investment portfolio, this move-in-ready 1-bedroom, 1-bath condominium is an excellent opportunity. Featuring brand-new luxury vinyl plank flooring and a freshly painted interior, this home offers a clean, modern feel throughout. The open-concept floor plan seamlessly connects the kitchen, dining, and living areas, creating a bright and inviting space for everyday living and entertaining. A set of French doors leads to the screened-in porch, providing the perfect spot to enjoy your morning coffee or unwind after a long day. The spacious bedroom features a large walk-in closet, offering plenty of storage. This condo also includes one assigned parking space, along with additional guest parking for visitors. Residents enjoy access to a community pool and onsite laundry facilities, adding to the convenience of low-maintenance living. Ideally located just minutes from SR 408, the University of Central Florida (UCF), shopping, dining, restaurants, and entertainment, this condo offers an unbeatable combination of comfort, convenience, and value. Whether you're searching for a primary residence or a smart investment opportunity in a high-demand area, this Central Florida gem is one you won't want to miss!

1000 S Semoran Boulevard Unit 305, Winter Park

2 Beds ⋅ 2 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code

WHAT A GEM! Tucked away in a private, sought after community and so conveniently located in breathtaking Winter Park. Here’s a beautifully maintained, upgraded and move-in ready home. With 2 large bedrooms and 1.5 bathrooms, this unit spans 1,219 square feet, providing an ideal space for cozy living. Enjoy the benefits of a peaceful and friendly community, with well-manicured grounds and a welcoming atmosphere. This charming home has been tastefully updated with upgraded laminate flooring, a renovated kitchen with granite countertops, newer cabinets and a stylish backsplash. The floor plan offers a dining & family room open combination which looks out on the porch and brings in plenty of natural light. Both nicely sized bedroom suites are on the second floor and have a shared & updated bathroom. Ample storage on the back patio for your bike and all your extra toys allowing you to enjoy your weekends. This is an extremely well managed community with an onsite manager taking pride in the community and care for their residents. Four Seasons community provides super amenities including a cubhouse with library, a renovated fitness center, 3 swimming pools, tennis courts, a laundry facility steps away and shuffleboard. Walk to Cady Way Park with tennis courts, baseball and soccer fields, playgrounds, community pool and Cady Way Trail. Minutes to Advent Health Winter Park Hospital, shopping on Park Avenue, Rollins College, Valencia, Full Sail and UCF. This pet friendly community and charming condo has everything you need! Great opportunity to own in FOUR SEASONS condominiums where LOCATION, LOCATION, LOCATION is prime!

200 Saint Andrews Boulevard Unit 2904, 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 ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 10 SubDv. ⋅ 32792 Zip Code

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

1 Beds ⋅ 1 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping! One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional Built-in Closets, Vanity and Mirrored Closets and updated Bath, accessible for Guests and close to Master! Updated Windows! Private Balcony! Owner is providing a One-Year Home Warranty and a $3,000 Flooring Credit. Make this affordable Unit your own!

1500 Gay Road Unit 4D, Winter Park

3 Beds ⋅ 3 Baths ⋅ Windward Square Sec 1 SubDv. ⋅ 32792 Zip Code

Welcome to 2487 Harbour Way, a spacious single-story townhome offering 3 bedrooms, 3 full bathrooms, and 1,803 square feet of comfortable living space. The practical layout features inviting living and dining areas, a well-equipped kitchen, central air, and a walk-in closet. Outside, garden space, lighting, and sidewalks add to the home's appeal. Enjoy a low-maintenance lifestyle in Windward Square, where residents have access to a community pool and playground, with the pool included in the low monthly HOA fee. Conveniently located near schools, parks, shopping, dining, and everyday essentials, this Winter Park property offers space, convenience, and community amenities in one appealing package. Schedule your private showing today!

2487 Harbour Way, Winter Park

4 Beds ⋅ 3 Baths ⋅ Landings At Hawks Crest SubDv. ⋅ 32792 Zip Code

Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,000 in luxurious builder upgrades, blending timeless design, modern comfort, and effortless Florida Living. This stunning home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes and a thoughtfully designed open-concept floor plan create a seamless flow throughout the home. Luxurious white ceramic tile spans the entire first floor, enhancing the home's bright and airy feel while providing both beauty and durability. The gourmet kitchen serves as the centerpiece of the home, featuring upgraded cabinetry, quartz countertops, stainless steel appliances, abundant storage and an expansive peninsula with bar seating. Spacious living areas and generously sized bedrooms provide comfort and flexibility for a variety of lifestyles. Upstairs, plush carpeting creates a warm and inviting retreat, while the primary suite offers a private sanctuary complete with a large walk-in closet and a spa-inspired bath. Additional bedrooms provide ample space for family, guests, a home office or a fitness room. Sliding glass doors extend the living space to a covered lanai, creating an inviting setting for outdoor dining, morning coffee or relaxed evenings enjoying Florida's year-round climate. Residents of Hawks Crest enjoy an exceptional collection of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, playgrounds, dog park, scenic trails and private access to Lake Howell. The community is also conveniently located near local favorites, including Kelly's Ice Cream, Foxtail Coffee and Park Maitland Preschool. Ideally situated just minutes from Park Avenue, downtown Maitland, major highways, and top-rated schools, this exceptional home offers effortless access to Central Florida's finest shopping, dining and cultural attractions. Despite its convenient location, the community maintains a sense of privacy and tranquility.

1418 Lone Feather Trail, Winter Park

2 Beds ⋅ 2 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code

Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to see this one before it is gone!

252 Scottsdale Sq Unit 252, 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

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