Winter Springs Homes with Pool

Winter Springs Homes with Pool

Welcome to Winter Springs, Florida – a hidden gem nestled in the heart of Seminole County! This charming city is renowned for its beautiful landscapes, friendly community, and a wealth of recreational opportunities. With its lush parks, scenic trails, and serene lakes, Winter Springs offers the perfect blend of suburban tranquility and vibrant living. Just a short drive from the bustling city of Orlando, residents enjoy easy access to world-class entertainment, dining, and shopping while still relishing the peaceful atmosphere that Winter Springs provides.

One of the standout features of homes in this picturesque city is the abundance of properties with pools. Imagine basking in the Florida sun, sipping your favorite drink, and taking a refreshing dip in your own private oasis. Homes with pools in Winter Springs are perfect for families, entertaining friends, or simply enjoying a quiet evening under the stars. Whether you’re looking for a cozy single-family home or a spacious estate, there’s a diverse selection of properties that cater to every lifestyle.

In addition to the allure of poolside living, Winter Springs boasts excellent schools, a strong sense of community, and numerous local events that bring residents together. From farmers' markets to seasonal festivals, there’s always something happening in this vibrant city.

If you’re seeking a place where comfort meets convenience, and where you can unwind in your own backyard retreat, Winter Springs is the perfect destination. Explore the homes for sale with pools today and discover the lifestyle you’ve always dreamed of!

Newest Winter Springs Homes with Pool

604 Casa Park Court G, Winter Springs
$235,000
2 Beds ⋅ 2 Baths ⋅ O6453699 MLS ⋅ 604 BLDG.
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
3755 Saint Lucie Court, Winter Springs
$515,000
4 Beds ⋅ 2 Baths ⋅ O6453480 MLS
Enjoy the best of Florida living at 3755 St. Lucie Court, a four-bedroom, two-bath pool home tucked into a cul-de-sac in Winter Springs. With low HOA fees and a convenient location near Red Bug Road, this move-in-ready home combines everyday comfort with the opportunity to add your own personal style. The approximately 2,300 square feet home includes a converted garage with air conditioning and carpeting, currently used as a dedicated office. Enjoy the flexibility of a home workspace or hobby room, with the option to convert the space back to a garage. As four bedrooms, it provide options for overnight guests and everyday living, while the pool invites you to cool off on sunny afternoons, unwind after a busy day, or enjoy a relaxed weekend at home. Shopping, restaurants, and everyday conveniences are nearby, making grocery runs, dinner plans, and daily errands easy to fit into your schedule. Convenient access to area highways also makes it easy to explore the greater Central Florida area. Settle in, enjoy the pool, and make this Winter Springs home your own!

3755 Saint Lucie Court, Winter Springs
846 Benchwood Court, Winter Springs
$385,000
3 Beds ⋅ 2 Baths ⋅ O6453509 MLS
PRICED TO SELL! Opportunity awaits at 846 Benchwood Ct in Winter Springs! This fixer-upper is ready for its next chapter and offers plenty of potential for buyers looking to renovate, customize, or invest. Notable features include a private fenced backyard and a screened-in pool, providing a great starting point for creating an inviting outdoor living space. Conveniently located in Winter Springs with access to shopping, dining, parks, and major roadways. Bring your vision and explore the possibilities this property has to offer. Priced to reflect its current condition and the improvements needed. Sold as-is.

846 Benchwood Court, Winter Springs
1000 Troon Trace, Winter Springs
$412,000
3 Beds ⋅ 3 Baths ⋅ O6440283 MLS
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 ⋅ O6453288 MLS ⋅ 270 BLDG.
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 ⋅ O6451380 MLS ⋅ Na BLDG.
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 ⋅ O6451663 MLS ⋅ 702 BLDG.
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
1314 Augusta National Boulevard, Winter Springs
$525,000
3 Beds ⋅ 3 Baths ⋅ O6448720 MLS
3 BED | NEW ROOF | NEW WINDOWS | POOL + CONSERVATION VIEWS | TUSCAWILLA GOLF COMMUNITY | Welcome to Country Club Village, nestled within the highly sought-after Tuscawilla community of Winter Springs! This beautiful 3-bedroom, 2.5-bathroom pool home offers an exceptional combination of location, lifestyle, and major updates, including a NEWER TILE ROOF (2023), NEW WINDOWS, and NEW EXTERIOR PAINT! One of the home's most desirable features is its private swimming pool overlooking a peaceful conservation area, offering a beautiful natural backdrop and added privacy that's hard to find in Tuscawilla. Inside, the thoughtfully designed floor plan offers plenty of space for everyday living and entertaining. Upon entering, you're welcomed into a spacious family room that flows into the formal dining room. The kitchen features stainless steel appliances (new in 2024), Corian countertops, and a charming eat-in breakfast nook with views of the pool and conservation beyond. A separate living room with a cozy fireplace creates the perfect space to unwind. A convenient half bathroom, laundry room, and two-car garage complete the first floor. Upstairs, the light-filled primary suite is a true retreat, featuring an additional sitting area ideal for a home office, reading nook, or additional relaxation space. The oversized ensuite bathroom offers dual vanities, a walk-in shower, and a garden tub. Two additional generously sized bedrooms and a full guest bathroom complete the second floor. Beyond the home itself, the Tuscawilla lifestyle is what truly makes this location special. Known for its beautiful tree-lined streets, established landscaping, neighborhood parks, playgrounds, and scenic walking areas, Tuscawilla is one of Winter Springs' most desirable communities. Residents also have the opportunity to join the nearby Tuscawilla Country Club, where optional memberships provide access to an 18-hole golf course, driving range, clay tennis courts, lap pool, leisure pool, and additional club amenities. The community is also served by Seminole County Public Schools, adding to its appeal. The community's HOA covers basic lawn care, making this home truly low-maintenance. With a new tile roof, new windows, a private conservation-backed pool, and an unbeatable location in the heart of Tuscawilla, this home offers a wonderful opportunity to enjoy everything that makes Winter Springs living so special!

1314 Augusta National Boulevard, Winter Springs
466 Tradition Lane, Winter Springs
$289,000
2 Beds ⋅ 3 Baths ⋅ O6451161 MLS ⋅ Heritage Park BLDG.
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 ⋅ O6451608 MLS ⋅ 600 BLDG.
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
1056 Condor Place, Winter Springs
$449,900
3 Beds ⋅ 2 Baths ⋅ O6450851 MLS
VR tour available. Seller offering up to $19,120 toward buyer closing costs, prepaid expenses, and/or an interest rate buydown. Conditions apply. Move-in ready 3-bedroom, 2-bath pool home in Winter Springs' established Sunrise community with the big-ticket items already handled: new roof (2026), new HVAC (2026), a new water heater (2026) and a whole-house repipe replacing the original polybutylene plumbing. A just-completed refresh adds fresh interior paint, stucco repairs with fresh exterior paint, new LED lighting and fixtures, new interior doors and door hardware, a new exterior light, and refreshed landscaping with fresh mulch. The kitchen features new white shaker soft-close cabinets, new Sparkling White quartz countertops, a new pull-out faucet and garbage disposal, and a new Whirlpool stainless steel range and dishwasher with a new stainless microwave. The primary bath adds a new white shaker vanity with a quartz top, a new toilet, faucet, mirror, vanity light and medicine cabinet, a retiled shower and a refinished tub, and the second bath a new vanity with a quartz top, toilet, faucet, mirror, vanity light and medicine cabinet, plus a reglazed tub and surround with new tub and shower trim. The single-story split-bedroom floor plan offers 1,524 SqFt with laminate flooring in the living areas and bedrooms, tile in the kitchen and baths, and no carpet anywhere. It includes a living room with a fireplace, a family room, a primary suite with a walk-in closet, and an attached 2-car garage with a new smart belt-drive opener with battery backup and a new steel garage entry door. Out back, sliding glass doors open to a covered lanai and a screened pool, just serviced, in a fenced backyard on a 0.22-acre lot. $336 annual HOA and no CDD. Conveniently located near shopping, dining and schools, with easy access to SR-417. Buyer credit available with use of Seller's preferred lender. Schedule your showing today.

1056 Condor Place, Winter Springs
161 Bear Springs Drive, Winter Springs
$500,000
3 Beds ⋅ 3 Baths ⋅ O6450193 MLS ⋅ Na BLDG.
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
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