Winter Springs Homes with Pool Community Features

Winter Springs Homes with Pool Community Features

Welcome to Winter Springs, Florida – a hidden gem nestled in the heart of Seminole County, where modern living meets the charm of nature. Known for its lush landscapes and vibrant community, Winter Springs offers a perfect blend of suburban tranquility and urban convenience. With its proximity to Orlando, residents enjoy easy access to world-renowned attractions while relishing the peaceful ambiance of a smaller town.

One of the standout features of Winter Springs is its array of homes with pool community amenities. Imagine waking up to sunny Florida mornings, stepping out into your backyard oasis, and diving into your private pool. These homes are designed for families and individuals who value outdoor living and recreation. Community features often include well-maintained pools, cabanas, and recreational areas that foster a sense of camaraderie among neighbors. Whether you're hosting a summer barbecue or enjoying a quiet evening by the pool, these residences provide the perfect backdrop for your lifestyle.

Winter Springs is also home to beautiful parks, top-rated schools, and a variety of shopping and dining options, making it an ideal place to raise a family or enjoy a relaxed lifestyle. The community is known for its friendly atmosphere and active lifestyle, with numerous walking trails, sports facilities, and events throughout the year.

If you're looking for a place that offers both comfort and a sense of community, Winter Springs is the perfect choice. Explore the homes with pool community features and discover your dream home in this enchanting Florida city!

Newest Winter Springs Homes with Pool Community Features

604 Casa Park Court G, Winter Springs
$235,000
2 Beds ⋅ 2 Baths ⋅ Casa Park Villas Ph 1 SubDv. ⋅ 32708 Zip Code
Move-in ready two-bedroom, one-and-a-half-bath Winter Springs townhouse with fresh interior paint, new laminate flooring upstairs, updated tile grout downstairs, plus a refreshed kitchen with painted cabinets, new countertop, faucet, and oven. Additional updates include new baseboards, new ceiling fans, new bedrooms light fixture, new blinds throughout, new fire detector, and, in the upstairs bathroom, a new tub, updated piping, and fixtures. The unit comes with two assigned parking spaces and access to a community pool. Nearby, you’ll find a park with tennis courts, barbecue pavilions, and a playground. Available for immediate occupancy.

604 Casa Park Court G, Winter Springs
1000 Troon Trace, Winter Springs
$412,000
3 Beds ⋅ 3 Baths ⋅ Greenbriar Sub Ph 1 SubDv. ⋅ 32708 Zip Code
Welcome to Greenbriar in Winter Springs! Situated on a corner lot, this 3-bedroom, 2.5-bath home offers 1,703 square feet of living space with a two-story layout and an inviting combination of indoor and outdoor spaces. The living and dining area features vaulted ceilings, luxury vinyl plank flooring, and a wood-burning fireplace, while French doors lead to a spacious screened rear patio. The kitchen offers quartz countertops, white shaker-style cabinetry, a tile backsplash, and a separate dining nook. Conveniently located on the main floor, the primary suite features a spacious closet, private bathroom with dual vanities, and sliding doors leading to the screened patio. Upstairs, two additional bedrooms provide flexible space for guests, hobbies, or a home office. Additional highlights include a two-car garage, tile roof, fenced backyard, and a community pool. Location-wise, you will enjoy immediate access to Tuscawilla Country Club, Trotwood Park, Bear Creek Nature Trail, Sam Smith Memorial Park, and the Oviedo Mall. Located in the established Greenbriar community, this home offers convenient access to shopping, dining, medical services, entertainment options, recreation activities, and everyday essentials. Schedule your private showing today and experience everything that this property has to offer.

1000 Troon Trace, Winter Springs
270 Moree Loop Unit 4, Winter Springs
$225,000
3 Beds ⋅ 3 Baths ⋅ Baytree Village SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully updated 3-bedroom, 2.5-bath townhome in desirable Winter Springs! This spacious, move-in-ready home features a recently remodeled kitchen, bathrooms, and flooring throughout! The updated kitchen boasts sleek countertops, dark wood cabinetry, and stainless steel appliances. Enjoy the Florida lifestyle with covered, screened-in front and rear porches, perfect for relaxing or entertaining. The HOA maintains the building exteriors, roofs, and common areas, with basic cable included. Residents can also enjoy the community pool and a convenient location near parks, shopping, and dining. Low-maintenance living in a great location?don't miss this opportunity!

270 Moree Loop Unit 4, Winter Springs
1354 Tarflower Drive, Winter Springs
$445,000
4 Beds ⋅ 3 Baths ⋅ Hickory Grove Twnhms SubDv. ⋅ 32708 Zip Code
Welcome to Hickory Grove, where modern living meets everyday convenience in the heart of Winter Springs! Built in 2024, this beautifully designed two-story townhome offers 4 bedrooms, 2.5 bathrooms, an open-concept living and dining area, and a spacious kitchen featuring stainless steel appliances, solid-surface countertops, a breakfast island, and a spacious pantry. The thoughtfully designed floor plan provides a comfortable balance of gathering space and private retreats, with the primary suite and additional bedrooms conveniently located upstairs. An attached two-car garage adds everyday functionality, while the covered front porch offers a welcoming place to unwind. Residents of Hickory Grove can enjoy community amenities including a swimming pool, playground, and dog park. Conveniently situated near Winter Springs Town Center, this location offers easy access to grocery stores, shopping, dining, coffee shops, parks, and major roadways for commuting throughout Central Florida. Enjoy the convenience of a connected location while having a comfortable place to call home. Whether you are looking for your next home or an opportunity to own in an established Central Florida market, this townhome offers a wonderful combination of modern design, low-maintenance living, and accessibility. Schedule your private showing and discover all that Hickory Grove and Winter Springs have to offer!

1354 Tarflower Drive, Winter Springs
702 Glasgow Court, Winter Springs
$299,990
4 Beds ⋅ 3 Baths ⋅ Highland Patio Homes SubDv. ⋅ 32708 Zip Code
Picture-perfect 4 bedroom townhouse with private outdoor living spaces in the wonderful Highlands community! This beautiful townhouse has had many updates and upgrades in recent years, including tongue and groove ceilings in the living room, updated kitchen and baths and much more! No carpet! Walking in there is a private courtyard and screened-in front porch to relax in and enjoy your morning coffee. You'll appreciate the soaring wood ceilings in the living room lined with windows overlooking the large private fenced patio. The kitchen features wood cabinets and stainless steel appliances, including a gas range with a double oven! The kitchen has an area large enough for an eat-in table and is adjacent to the screened-in front porch. The first-floor primary has a very large seating area/office overlooking the patio, as well as a large custom built-in wood closet. The primary bath has a stylish vanity, newly tiled shower and a seamless glass door. Upstairs, you'll find three other roomy bedrooms, all with beautiful wood flooring. Other recent updates include a full replumb, new energy efficient windows and doors and garage door. Located in the highly desired Highlands Community, which features a clubhouse and community pool, tennis & pickleball courts, a lake for fishing, park and playground and multiple walking trails!

702 Glasgow Court, Winter Springs
466 Tradition Lane, Winter Springs
$289,000
2 Beds ⋅ 3 Baths ⋅ Heritage Park Twnhms SubDv. ⋅ 32708 Zip Code
Virtually Staged. Beautiful townhome in Heritage Park conveniently located in Winter Springs and close to EVERYTHING! Immaculate 2 bedrooms with 2.5 bathrooms with a covered back porch and single car garage. This townhome is very well maintained with faux wood vinyl flooring and berber carpets. Spacious kitchen with stainless steel appliances. Great floor plan. Secluded and covered back patio to relax and chill out and the end of the day. Gated community which provides privacy and security for your family. Heritage Park also has amenities including a fabulous community pool and playground. Heritage Park is near to convenient Winter Springs and Longwood shopping centers, restaurants and retail stores. Great Seminole County school district. Do not miss the opportunity to own this property!!!! Perfect investment property for rental income. Turn key and ready to go! Request your appointment and come see this gem today!

466 Tradition Lane, Winter Springs
600 Casa Park N Ct., Winter Springs
$219,900
2 Beds ⋅ 1 Baths ⋅ Casa Park Villas SubDv. ⋅ 32708 Zip Code
Welcome home to the well established neighborhood of Casa Park Villas. Rare one story townhouse, 2 bedroom, 1 full bathroom, 980 square feet of living area end unit. From the moment you step inside, you'll love the bright, open layout that flows so naturally from the family room to the dining area and kitchen. It creates such a warm, inviting space that is truly perfect for both everyday relaxing and host-filled gatherings. Come and make it your own. The Community features enjoyable sparkling swimming pool. Close by is Trotwood Park that offers pickleball and tennis courts, splash pad, playgrounds, basketball courts, a large pavilion, yoga, community events. Great location! Conveniently located to nearby shopping, banks, medical centers, and restaurants as well as easy access to major highways. Elementary and middle schools are walking distance. Don't miss it. Priced to sell. Will Not Last!

600 Casa Park N Ct., Winter Springs
161 Bear Springs Drive, Winter Springs
$500,000
3 Beds ⋅ 3 Baths ⋅ Hickory Grove Twnhms SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully designed, newly constructed 2026 END-UNIT townhome in the desirable Hickory Grove community of Winter Springs, Florida. Offering 3 bedrooms, 2.5 bathrooms, and approximately 1,704 square feet of living space, this two-story residence combines modern style, functionality, and low-maintenance living. Step inside the 8’ entryway door to find a bright and airy living space featuring a contemporary kitchen equipped with stainless steel appliances, recessed lighting, 18” tile, and a large breakfast bar, making it ideal for entertaining and everyday living. This Sofia Model by Mattamy Homes features a thoughtfully designed floor plan with a FIRST FLOOR PRIMARY SUITE abundant with natural light, a generous walk-in closet, and a private en suite bathroom complete with dual vanity sinks and a spacious walk-in shower. Upstairs, you will find two additional bedrooms, a guest bathroom, and a versatile loft providing a flexible space that would be ideal for a home office or media room. Additional highlights include high ceilings, an in-home laundry room (located on the first floor), custom plantation shutters, a smart thermostat, a rear entry 2-car garage complete with shark floor coating, a covered screened-in lanai, and a covered front porch with views of Veterans Memorial Park. Residents of Hickory Grove also enjoy community amenities, including a community resort-style swimming pool, playground, and dog park. The HOA also covers exterior maintenance, internet, and landscaping. This home is conveniently located near Winter Springs Town Center and offers access to SR-434 and SR-417, as well as shopping, dining, parks, walking trails, and the Seminole County Public School District, which is widely ranked #1 in Central Florida. Don’t miss this opportunity to enjoy maintenance-free living and make this beautiful townhome your new home!

161 Bear Springs Drive, Winter Springs
733 Lakeview Drive, Winter Springs
$365,000
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
Fresh interior paint and partial new flooring. Well-maintained 3-bedroom, 2-bath single-story home in Winter Springs with 1,597 sq ft of living space. The open layout offers a living room, family room, and separate dining area, plus a private primary suite with walk-in closet. Located on a quiet street near Winter Springs schools, parks, and shopping.

733 Lakeview Drive, Winter Springs
499 Club Drive, Winter Springs
$205,000
2 Beds ⋅ 2 Baths ⋅ Cypress Club SubDv. ⋅ 32708 Zip Code
Virtually Staged. As you arrive at this beautiful 2 bedroom + loft, 2 bath residence in a serene townhome community within The Highlands in Winter Springs, you’ll note a feeling of privacy, relaxation, and tranquility among the lush landscaping, fantastic amenities, and peaceful walking trails. TOUR THE HOUSE WITH THE VIRTUAL TOUR AND WALK THRU VIDEO LINKS. Step inside to a spacious open floorplan where light bathes the soaring vaulted ceilings and tile flooring runs throughout the main living areas. The family cook will enjoy preparing meals among the new appliances (2022) in the functional kitchen layout, while overlooking the great room and exterior nature views. Step out to the screened patio to enjoy your morning coffee, where you’ll also find an outside storage closet offering a convenient place for your bikes, tools, or gardening supplies. The layout of this home offers double suites, thoughtfully split between the two levels, each with a full bath with shower/tub combo. Upstairs, a bonus loft provides an ideal flex space for a home office, reading nook, or more! Life here is stress-free with a new roof (2026) and A/C (2023), and 2 reserved parking spaces, side-by-side, right outside your front door. Beyond the home itself, this community provides you a carefree lifestyle with the HOA taking care of exterior maintenance and landscaping, leaving you plenty of time to meet up with friendly neighbors to enjoy the private community pool within the neighborhood, as well as the Highlands’ exceptional amenities -- including a junior Olympic-size lap pool, tennis/pickleball courts, clubhouse, playground, and picnic areas, perfect for relaxing moments or social gatherings. Conveniently located with easy access to main thoroughfares, everyday conveniences are close by -- groceries, restaurants, shopping, banks, fitness centers, etc. – as well as top-rated Seminole County schools. Come see why your new neighbors already love to call the area home and are enjoying the care-free lifestyle you deserve!!

499 Club Drive, Winter Springs
491 Harbor Winds Court, Winter Springs
$335,000
3 Beds ⋅ 3 Baths ⋅ Harbor Winds SubDv. ⋅ 32708 Zip Code
Enjoy extra savings with up to $10,000 in seller concessions, and breathe easy knowing the big expenses are already handled for you with a newer Roof (2023), AC (2022), and Water Heater (2023)! Welcome to your beautiful new chapter at 491 Harbor Winds Ct! Nestled in a highly desirable gated community, this bright, move-in-ready townhome is designed for effortless living. Retreat to your private 1st-floor primary sanctuary, complete with dual closets, a walk-in shower, and a relaxing jacuzzi. The cheerful layout offers 3 spacious bedrooms, 2.5 baths, convenient laundry, and a 2-car garage. Reclaim your weekends! Your low monthly HOA fee covers exterior maintenance and grounds care, giving you more time to enjoy the resort-style community pool, nearby nature trails, and top-rated Seminole County schools. Everything you have been looking for is right here. Schedule your tour today!

491 Harbor Winds Court, Winter Springs
627 Clearn Court, Winter Springs
$469,000
5 Beds ⋅ 4 Baths ⋅ The Highlands Sec Four Tracts A & B Rep SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully updated home, with it's own IN-LAW SUITE, tucked away on a quiet cul-de-sac in Winter Springs! The first floor offers plenty of room to spread out, featuring a sunken living room, cozy fireplace, and formal dining area. This living space opens to the large fully fenced backyard. The kitchen has been updated with bright & light cabinets, countertops, stainless steel appliances, and right off the kitchen is a screened covered porch with access to the backyard. Through the laundry room, is the garage which has been thoughtfully converted into a private 1 bedroom, 1 bathroom in-law suite with its OWN ENTRANCE. This space has been beautifully done and features its own kitchen with a stove, microwave, and refrigerator, and it's own AC unit. You can access the in-law suite from inside or outside the home, depending on how you'd like to use the space. Whether used as an in-law setup, guest space, home office, or additional flex space, it gives the home versatility that is hard to find. Upstairs, is the primary suite with an en-suite bathroom and generous closet. Off the primary suite is a spacious balcony, just in time for Florida's great fall weather! Three additional bedrooms and a full guest bathroom provide plenty of space for family, guests, or working from home. Conveniently located in Seminole County with easy access to Winter Springs Town Center, Longwood, Lake Mary, Altamonte Springs, SR 434, US 17-92, and I-4, making getting around Central Florida easy. If you've been looking for a home with extra space and possibilities beyond the traditional floor plan, this one deserves a look! The Highlands neighborhood features a great community pool and tennis courts/pickleball courts, as well as beautiful nature trails and stately historic trees.

627 Clearn Court, Winter Springs
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