Winter Springs Homes with Pool Amenities

Winter Springs Homes with Pool Amenities

Welcome to Winter Springs, Florida—a hidden gem nestled in the heart of Seminole County! Known for its picturesque landscapes, friendly neighborhoods, and a strong sense of community, Winter Springs offers an idyllic setting for families, retirees, and anyone looking to embrace the quintessential Florida lifestyle. With its lush parks, scenic trails, and vibrant local culture, this charming city is the perfect blend of tranquility and convenience.

Winter Springs boasts a variety of amenities, including top-rated schools, shopping centers, and recreational facilities, making it an ideal place to call home. Residents enjoy a plethora of outdoor activities, from hiking the beautiful trails at the nearby Black Bear Wilderness Area to picnicking in the lush parks that dot the city. The community hosts numerous events throughout the year, fostering a warm and welcoming atmosphere for everyone.

When it comes to real estate, Winter Springs offers a fantastic selection of homes, particularly those with pool amenities. Imagine relaxing in your own private oasis, soaking up the Florida sun beside your sparkling pool, or hosting unforgettable summer barbecues with friends and family. Whether you're seeking a cozy single-family home or a spacious property perfect for entertaining, Winter Springs has something for everyone.

With its combination of suburban charm and modern conveniences, Winter Springs is truly a place where you can live, play, and thrive. Discover your dream home with pool amenities today, and experience the wonderful lifestyle that this enchanting city has to offer!

Newest Winter Springs Homes with Pool Amenities

1354 Casa Park Circle, Winter Springs
$245,000
2 Beds ⋅ 3 Baths ⋅ Casa Park Villas Ph 1 SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully remodeled, move-in-ready townhome in the desirable Casa Park Villas community of Winter Springs! Perfectly situated directly across from Trotwood Park and conveniently located near highly regarded Seminole County schools, this charming 2-bedroom, 2.5-bath home offers the perfect combination of modern elegance, comfort, and convenience! Step inside and fall in love with the beautifully updated interior, featuring a remodeled kitchen with stylish finishes and newer appliances (2025), perfect for everyday living and entertaining. The entire first floor showcases beautiful tile flooring, while the second floor features gorgeous luxury vinyl plank flooring installed in 2025, creating a seamless blend of style and functionality. Both upstairs bathrooms were beautifully remodeled in 2025 with modern finishes, offering a fresh and contemporary feel. Additional improvements include four new front windows (2025), a new sliding glass door (2025), a water heater (2023), and a newly installed backyard fence (2025), creating a private outdoor space perfect for relaxing or entertaining. Enjoy the benefits of living in Casa Park Villas, where the HOA covers pool maintenance and lawn maintenance, allowing you to spend less time on upkeep and more time enjoying your home! Community amenities include a pool, spa, and sauna. Outdoor enthusiasts will love having Trotwood Park just across the street, offering wonderful opportunities for recreation and relaxation. Ideally located near Winter Springs Town Center, SR-417, UCF, shopping, restaurants, and entertainment, this home provides convenient access to everything Central Florida has to offer. Beautifully remodeled, thoughtfully updated, and ready for its next owner! Why spend time and money renovating when you can move right into a home where the work has already been done? Schedule your private showing today and discover the beauty, convenience, and low-maintenance lifestyle of Casa Park Villas!

1354 Casa Park Circle, Winter Springs
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 2-Bedroom Townhouse in Winter Springs! This beautifully refreshed 2-bedroom, 1.5-bath townhouse features fresh interior paint, new baseboards, new laminate flooring upstairs, and refreshed tile grout downstairs. The kitchen has been refreshed with freshly painted cabinets, a new countertop, faucet, and oven. Additional improvements include new ceiling fans, a new bedroom light fixture, new blinds throughout, and a new smoke detector. The bathroom features a brand-new bathtub, new toilet seats, and updated fixtures. The unit also includes two assigned parking spaces and access to a community pool. Just nearby, enjoy a community park with tennis courts, barbecue pavilions, and a playground. Available for immediate occupancy. Don’t miss this opportunity to enjoy a freshly refreshed home in a convenient Winter Springs location!

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
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
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
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
1013 Walnut Creek Cove, Winter Springs
$499,900
3 Beds ⋅ 2 Baths ⋅ Parkstone Unit 4 SubDv. ⋅ 32708 Zip Code
Beautiful 4-bedroom POOL home with awesome pond front in the exclusive gated community of Parkstone! Formal Living, Dining, and Family rooms. Spacious eat-in kitchen with stainless steel appliances. Large owner's suite with huge closet and elegant garden tub and separate shower. High ceilings and tile flooring throughout house. One story home. A/C 2018. Laundry room. Covered screened-in back porch with POOL and stunning view of the pond. 2 car garage. Roof 5 yrs old. Irrigation system. HOA mows yard. House is on a CUL-DE-ac so very quiet. Enjoy the community pool, splash pad, tennis courts, playground, and fishing pier. Near the Seminole Trail for biking and walking as well as Central Winds Park/dog park. Good schools. Great location. Must See!

1013 Walnut Creek Cove, Winter Springs
1436 Winter Wharf Lane, Winter Springs
$399,000
3 Beds ⋅ 4 Baths ⋅ Jesups Landing SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome to easy, stylish living in Jesup’s Landing, one of Winter Springs’ most desirable communities. This spacious 3 Bedroom, 3 1/2 Bath Townhome features a versatile split-level design that creates a comfortable sense of separation between living areas while still offering plenty of room to gather and entertain. The beautifully appointed kitchen features 42-inch cherry cabinetry, granite countertops, and a spacious prep island, creating an inviting and functional space for cooking, baking, and entertaining. Upstairs, the primary suite offers a generous bedroom, a spacious walk-in closet, and a well-designed primary bath with a double-sink vanity, separate shower, and soaking tub. A second upstairs bedroom also features its own en-suite bath with a walk-in shower and a large walk-in closet, providing added privacy and convenience. The lower level includes an additional secondary bedroom with its own en-suite shower bath, along with access to the two-car garage and extra storage space. New Carpet in the Bedrooms and Stairways was just installed for a MOVE-IN READY transition for the new Owner. The exterior has also been refreshed with New Paint, New Screen on Balcony and the home features a New Roof for added value and peace of mind. The location offers exceptional convenience with Central Winds Park, shopping, dining, SR 417, Orlando Sanford International Airport, UCF, and Seminole State College all within easy reach. Jesup’s Landing residents enjoy a variety of community amenities, including a clubhouse, fitness center, and inviting swimming pool. With its spacious floor plan, recent updates, convenient location, and low-maintenance lifestyle, this home offers a wonderful opportunity to enjoy all that Winter Springs has to offer. ROOF - 2026, A/C and Water Heater - 2014.

1436 Winter Wharf Lane, Winter Springs
414 Horizon Drive, Winter Springs
$299,900
3 Beds ⋅ 2 Baths ⋅ Seasons The SubDv. ⋅ 32708 Zip Code
Stunningly updated and refreshed single-family home in "The Seasons," located in the highly desirable Winter Springs community in Seminole County, FL. Welcome to 414 Horizon Drive! This charming 3-bedroom, 2-bathroom residence offers 1,101 square feet of bright and inviting living space, combining beautiful curb appeal with the convenience of low-maintenance landscaping, two designated parking spaces, and available guest parking. Step inside to discover a completely refreshed interior featuring brand-new flooring, trim work, fresh paint, modernized hardware, and updated light fixtures throughout. The kitchen has been upgraded with brand-new cabinetry, pristine countertops, a brand-new dishwasher, and a sleek over-the-range microwave with stove setup. This is complemented by stylishly updated bathrooms featuring brand-new vanities, mirrors, countertops, sinks, faucets, and flooring. Situated just steps from the community pool, this home offers effortless leisure—simply step out your front door and take a brief left down the sidewalk. Residents also enjoy neighborhood amenities including a playground, tennis courts, and basketball courts. Conveniently located near local parks, top-rated Seminole County schools, shopping, and major roadways, this turn-key home is an outstanding opportunity.

414 Horizon Drive, Winter Springs
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