Winter Park Homes with Pool Community Features

Winter Park Homes with Pool Community Features

Welcome to Winter Park, Florida—a picturesque city that seamlessly blends small-town charm with vibrant urban living. Nestled just north of downtown Orlando, Winter Park is renowned for its stunning lakes, lush parks, and a rich cultural heritage. With its tree-lined streets and historic architecture, this enchanting city offers a unique lifestyle that attracts families, retirees, and professionals alike.

One of the highlights of Winter Park is its commitment to outdoor living, making it an ideal destination for those who appreciate the sun-soaked Florida lifestyle. Many homes in this beautiful community feature private pools, providing a perfect oasis for relaxation and recreation. Imagine spending your weekends lounging by your poolside, hosting summer barbecues, or enjoying a refreshing dip after a long day. With a variety of properties available, from charming bungalows to luxurious estates, there’s a perfect home with a pool waiting for you.

Beyond the allure of private pools, Winter Park boasts a vibrant community atmosphere. The city is home to an array of boutiques, art galleries, and fine dining options, ensuring that residents can enjoy a rich cultural experience right at their doorstep. The Winter Park Scenic Boat Tour offers a unique way to explore the city’s stunning waterways, while the renowned Morse Museum showcases an impressive collection of Tiffany glass.

In Winter Park, you’re not just buying a home; you’re investing in a lifestyle filled with warmth, community, and endless opportunities for enjoyment. Come discover the magic of Winter Park, where your dream home with a pool awaits!

Newest Winter Park Homes with Pool Community Features

$229,900
3 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 01 SubDv. ⋅ 32792 Zip Code
Welcome To This Beautifully 3 Bedroom, 2.5 Bathroom Condominium Located in the Desirable Hidden Oaks Community. Offering Updated Living Space, This Home Combines Comfort, Style, and an Unbeatable Location. Step Inside to a Spacious and Inviting Family Room Featuring Beautiful Laminate Flooring, Abundant Natural Light, and an Open, Welcoming Atmosphere. The Updated Kitchen Is Sure to Impress with Quartz Countertops, Stainless Steel Appliances, and A Sliding Glass Door That Opens to a Private Patio—Perfect for Relaxing or Entertaining. Upstairs, You'll Find All Three Bedrooms and Two Full Bathrooms, including a Generously Sized Primary Suite with a Walk-In Closet and Large Front-Facing Windows That Fill the Room with Natural Light. Residents of Hidden Oaks Enjoy a Peaceful Setting with Access to a Community Swimming Pool, Assigned Parking, And Plenty of Guest Parking. Ideally Located Just Minutes from Major Highways 408 And 417, This Home Is Only 4 Minutes from Full Sail University, Minutes from the University of Central Florida (UCF), Downtown Orlando, and Conveniently Close to Valencia College, Rollins College, Winter Park Shopping and Dining, Restaurants, and Everyday Conveniences. The Property Is Also Zoned for Highly Desirable Winter Park Schools, Making It an Excellent Choice for Homeowners and Investors Alike. Don't Miss This Move-In-Ready Opportunity in One of the Area's Most Convenient Locations!

7413 Belle River Court Unit 3, Winter Park
$284,000
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
$399,900
3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code
Welcome home to this beautifully maintained, nearly new Pulte Townhome in the heart of Winter Park! Built in 2023, in the gated community of Grayson Square, this stylish two story residence offers 3 bedrooms, 2.5 bathrooms, and an attached one car garage, combining modern design with everyday convenience. The open-concept main living area is perfect for entertaining, featuring elegant quartz counter-tops, Whirlpool stainless steel appliances, ample cabinet space, and a large island overlooking the living and dining areas. Enjoy the upgraded smart home technology, high speed internet and cable already included into the low HOA, making working from home and streaming effortless. Upstairs, you will find a spacious primary suite complete with a generous walk-in closet and a private en-suite bathroom designed for comfort and relaxation. Two additional bedrooms provide plenty of room for family, guests. or a dedicated home office. Also to note is that there are no direct rear neighbors, allowing you to enjoy peaceful outdoor views on the back covered patio. The community is beautifully maintained and offers a resort-style pool and cabana and sidewalks for evening strolls. One of the homes most desirable features is the one thing you need the most but comes unseen is the 10 year transferable Pulte home warranty. Located just minutes from Winter Parks renowned shopping, dining, entertainment, parks and top commuter routes like 417, you'll enjoy easy access to everthing Central Florida has to offer while coming home to a quiet, friendly neighborhood. If your looking for a modern, energy efficient home with premium finishes and virtually maintenance free simple living, this is the one youve been waiting for!

2017 Canny Cove, Winter Park
$145,000
2 Beds ⋅ 2 Baths ⋅ Whisperwood Condo 02 SubDv. ⋅ 32792 Zip Code
Welcom Home to your second/top floor 2-bedroom, 2 bathroom condo with brand new beautiful luxury vinyl floors throughout. This property has been a rental the last few years and is now ready for an owner or investor to make it their own. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options. Schedule your showing today!

7340 Swallow Run Unit 7340, Winter Park
$154,900
3 Beds ⋅ 2 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code
Vacant! Great location! Must See! New paintinf interior, and new carpet. The best area at Winter Park, close to major shoppiing center,

1695 Lee Road Unit A101, Winter Park
$115,000
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
$675,000
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
$278,000
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
$129,000
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
$259,000
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
$399,000
3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code
Step into this beautifully designed townhome featuring an open-concept kitchen, dining, and living area—perfect for everyday living and entertaining. The modern kitchen boasts stainless steel appliances, gray cabinetry, and quartz countertops. Upstairs, the spacious primary suite offers a walk-in closet and a private in-suite bath with dual quartz vanities, while two additional bedrooms, a full bath, and a convenient laundry closet complete the second floor. Relax on the covered lanai and enjoy the privacy of this home's cul-de-sac location. The HOA includes landscaping, exterior maintenance and repairs, high-speed internet, and access to the gated community, providing low-maintenance living. With no CDD, this home is an excellent option for both homeowners and investors. Ideally located in highly desirable Winter Park, Grayson Square is just minutes from SR-436, SR-434, and SR-417, with Publix, Starbucks, shopping, dining, and top-rated Seminole County schools nearby. Park Avenue is only a short drive away, making this home the perfect combination of convenience, comfort, and value.

2033 Canny Cove, Winter Park
$185,000
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
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