Winter Springs Homes with Pool Community Features

Winter Springs Homes with Pool Community Features

Welcome to Winter Springs, Florida, a picturesque gem nestled in the heart of Seminole County. Known for its charming neighborhoods, lush landscapes, and a strong sense of community, Winter Springs offers the perfect blend of suburban tranquility and vibrant living. With its proximity to the bustling city of Orlando, residents enjoy easy access to world-class entertainment, dining, and shopping, all while relishing the peaceful ambiance of this inviting town.

One of the standout features of Winter Springs is its diverse selection of homes, particularly those with stunning pools that provide an oasis for relaxation and recreation. Imagine coming home to your own private retreat, where you can unwind by the water, host summer barbecues, or enjoy a refreshing swim after a long day. The homes in this community are designed with comfort and leisure in mind, featuring spacious layouts, modern amenities, and beautifully landscaped yards that enhance the overall appeal.

Winter Springs is not just about beautiful homes; it’s also about community. The area boasts excellent schools, numerous parks, and recreational facilities, making it an ideal place for families and individuals alike. With a variety of community events and activities throughout the year, residents can easily connect and build lasting friendships.

Whether you’re looking for a cozy family home or a luxurious retreat with a pool, Winter Springs offers a welcoming atmosphere that feels like home. Discover the charm of this delightful city and find your perfect slice of paradise today!

Newest Winter Springs Homes with Pool Community Features

$275,000
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
Set within the established Wildwood community of Winter Springs, this near 1,400-square-foot townhome offers two features that are especially hard to find, a single-story layout and a two-car garage. Add in recent updates that bring real peace of mind, and the result is easy, comfortable living from the moment of arrival. Luxury vinyl plank flooring flows throughout the home, with tile in the kitchen, creating a clean, cohesive look from room to room. At the heart of the living room, a wood-burning fireplace with a natural coquina surround adds warmth and a distinctly Florida sense of character, making the space as inviting on a cool winter evening as it is for everyday gatherings. The dining area opens to the kitchen for a natural, connected flow, and extends outdoors to a covered, screened patio well suited to morning coffee, casual meals or simply enjoying the fresh air without the bugs. The oversized primary bedroom serves as a retreat, featuring a walk-in closet, an en-suite bath and direct access to a rear open patio for a quiet moment outside. Two additional bedrooms and a second full bath provide flexibility for family, guests, a home office or hobby space. The attached two-car garage adds everyday convenience along with valuable room for storage, a workshop area or simply keeping vehicles protected from the Florida sun and rain. Residents of Wildwood enjoy access to a community park, playground, swimming pool and tennis courts, offering plenty of opportunities for recreation close to home. Important recent updates include a 2019 HVAC system and a 2023 roof, two of the most significant investments in any home already taken care of. With the ease of single-story living, the rare advantage of a two-car garage and major systems recently addressed, this townhome is an easy choice in a well-located Seminole County neighborhood.

728 Ridgewood Way, Winter Springs
$275,000
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
Set within the established Wildwood community of Winter Springs, this nearly 1,400-square-foot townhome offers two features that are especially hard to find, a single-story layout and a two-car garage. Tile flooring flows throughout the home, creating a clean, cohesive look from room to room that is durable and easy to maintain. The living room offers a comfortable, welcoming space for relaxing or gathering with friends. The dining area opens to the kitchen for a natural, connected flow, and extends outdoors to a covered, screened patio well suited to morning coffee, casual meals or simply enjoying fresh air without bugs. The oversized primary bedroom serves as a retreat, featuring a walk-in closet, an en-suite bath and direct access to a private covered lanai for a quiet moment outside. Two additional bedrooms and a second full bath provide flexibility for family, guests, a home office or hobby space. The attached two-car garage adds everyday convenience along with valuable room for storage, a workshop area or simply keeping vehicles protected from the Florida sun and rain. Residents of Wildwood enjoy access to a community park, playground, swimming pool and tennis courts, offering plenty of opportunities for recreation close to home. A newer HVAC system adds to the home's appeal. With the ease of single-story living and the rare advantage of a two-car garage, this townhome is an easy choice in a well-located Seminole County neighborhood.

700 Castlewood Drive, Winter Springs
$309,000
3 Beds ⋅ 2 Baths ⋅ Seasons The SubDv. ⋅ 32708 Zip Code
Virtually Staged. 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
$550,000
3 Beds ⋅ 2 Baths ⋅ Georgetowne Unit 3 SubDv. ⋅ 32708 Zip Code
Private Oasis Meets Smart Luxury in Georgetown. Welcome home to high-end design, smart living, and effortless comfort. Nestled in the heart of one of Georgetown’s most coveted neighborhoods, this fully remodeled, single-story 3-bedroom, 2-bath sanctuary showcases the sought-after Tuskawilla floor plan - offering 1,735 square feet of light-filled open living space, where every detail has been thoughtfully redesigned for effortless Florida living. Step inside to gorgeous wood flooring that spans every single room, beautifully highlighting the home's open layout. The centerpiece of the interior is the custom-remodeled kitchen, complete with new cabinetry, smart Samsung appliances you can control from your phone, and a massive quartz island designed to keep family and friends gathered right at the heart of the home. The spacious split-bedroom layout ensures maximum privacy, featuring generously sized bedrooms and a primary suite retreat. The primary bedroom showcases an oversized, custom-built California closet that makes moving in effortless, alongside an en-suite bath with dual vanities, quartz countertops, a deep soaking tub, and a separate shower. Premium fixtures and finishes continue seamlessly throughout the entire home. Beyond the main living space, step out into your private outdoor sanctuary: a screened pool and covered lanai framed by peaceful, lush views with no rear neighbors. Designed for ultimate convenience, this intelligent home lets you control climate settings, open or close the garage door, and manage automation right from your smartphone. Convenience extends to the garage with an electric vehicle charger ready for plug-and-play use. Security is top-tier, backed by a hardwired system featuring seven exterior and one interior audio-visual cameras for complete, 24/7 peace of mind whether you are relaxing inside or traveling away from home. The property pairs modern tech with reliable mechanicals, including a Roof, A/C, and water heater replaced in 2019; an energy-efficient RadiantGUARD® Radiant Barrier Xtreme insulation system in the attic; a hybrid energy-efficient pool pump (2019); and new smart Samsung stainless steel kitchen appliances (2024), plus a matching Samsung washer and dryer. With the HOA handling front lawn care, this home is truly 100% move-in ready. Enjoy mornings at Tuscawilla Country Club, afternoons at Trotwood Park, and weekends on the Seminole Trail - all paired with top-rated Seminole County schools and swift access to SR-417. Don't miss this opportunity; schedule your showing today. For tech-focused buyers, the complete network infrastructure - including the server rack, 48-port Netgear PoE switch, pfSense router, UniFi Access Points, Synology RS822+ (4x8TB drives), and Synology DiskStation DS923+ can also be included via a separate bill of sale.

766 Andover Circle, Winter Springs
$325,000
3 Beds ⋅ 2 Baths ⋅ Wildwood SubDv. ⋅ 32708 Zip Code
Welcome to 654 Cypress Lane, a move-in-ready 3-bedroom, 2-bathroom home featuring fresh interior paint throughout. The main entry opens into a bright living room that connects seamlessly to the kitchen, complete with quartz countertops and stainless steel appliances. Designed with a practical split floor plan, the primary bedroom sits on one side of the home with its own en-suite bathroom, while two secondary bedrooms share a second full bath on the opposite side. A dedicated laundry room adds extra convenience. Out back, a screened-in back porch offers a quiet spot to relax, leading to a private, fenced yard framed by mature shade trees. Homeowners will also appreciate the benefit of a low HOA fee, with amenities such as a pool, basketball and tennis court, playground, dog park, and much more! Located in Winter Springs, this home puts you near top-rated Seminole County schools, local parks, and the Cross Seminole Trail. Enjoy easy access to shopping and dining at the Winter Springs Town Center, with quick routes to SR 417 for a smooth commute to UCF, Oviedo, and Orlando.

654 Cypress Lane, Winter Springs
$549,000
3 Beds ⋅ 4 Baths ⋅ Seminole Crossing Townhomes SubDv. ⋅ 32708 Zip Code
Welcome to 1166 Spotted Sandpiper Loop in Winter Springs, a spacious three-story, 3-bedroom, 3.5-bath townhome in Seminole Crossing. With a floor plan that offers plenty of room to spread out, this home is one of only two townhomes in the community featuring this unique layout. Its multi-level design gives the home more character and separation than the typical boxy townhome, with gathering spaces and private retreats thoughtfully placed across three floors. The first floor features a private bedroom and full bathroom, making it ideal for guests, extended family, or a home office, along with an oversized rear-facing garage and covered front porch. Upstairs, the main living level brings the gourmet kitchen, dining area, and family room together in an open, light-filled space. Designed with both everyday living and entertaining in mind, the gourmet kitchen features a walk-in pantry, generous prep and storage space, and double ovens. French doors open to an expansive balcony, creating an inviting spot to enjoy some fresh air or unwind at the end of the day. The third floor is home to the primary suite, a second bedroom, and a flexible loft. The primary suite offers a large walk-in closet and spacious bathroom with dual sinks, soaking tub, and separate shower. The second bedroom also has a walk-in closet, with a full bathroom conveniently located just outside the bedroom, while the loft can easily become a lounge, media area, study, or home office. The laundry room is conveniently located nearby. One of the biggest perks of townhome living here is the maintenance-free exterior. The HOA takes care of the outdoor upkeep, including mowing, weeding, flower beds, tree trimming, and more. When the time comes, the HOA is also responsible for exterior painting and roof replacement, giving you even less to worry about. And the location makes everyday errands surprisingly easy. The Cross Seminole County Trail is just a short distance from the home located right outside the neighborhood, while nearby grocery stores and restaurants are also just a walk away. Starbucks is even closer, with Chick-fil-A, Wawa, and Ace Hardware coming soon. Residents also enjoy access to a community pool, sidewalks, and additional recreational spaces, with convenient access to SR 434, Winter Springs Town Center, Oviedo, and surrounding Seminole County. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**

1166 Spotted Sandpiper Loop, Winter Springs
$170,000
2 Beds ⋅ 2 Baths ⋅ Sheoah Sec 3 SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully updated 2-bedroom, 2-bath first-floor condo located at 417 Sheoah Blvd, Apt 17, Winter Springs, FL 32708. This inviting home offers a spacious and comfortable floor plan with plenty of natural light throughout. The renovated kitchen provides a fresh and functional space and comes complete with all appliances. A washer and dryer are also included for added convenience. The home also features renovated bathrooms, adding to its fresh and move-in-ready appeal. The spacious living and dining areas feature tile flooring, creating an open and welcoming space for everyday living and entertaining. The generously sized primary bedroom features wood-look flooring and sliding glass doors that open directly to the outdoor patio, bringing in natural light and providing convenient access to the outdoor space. Enjoy the screened-in back porch and extended paver patio overlooking the community’s mature trees and green space. This inviting outdoor area offers a peaceful setting and added privacy, perfect for enjoying your morning coffee, relaxing outdoors, or entertaining guests. The community offers desirable amenities including a swimming pool and tennis courts. The HOA maintains the building exterior, roof, and community landscaping, providing valuable services for residents. The HOA fee is $485 per month. In addition, there is a separate Master Association fee of $436, paid annually at the beginning of the year. Conveniently located in Winter Springs, this updated first-floor condo offers a wonderful combination of renovated interiors, spacious living areas, inviting outdoor spaces, and community amenities. Enjoy a great location within the desirable Seminole County school district, with convenient access to shopping, dining, parks, and major roadways. Schedule your private showing today and discover everything this beautiful condo has to offer!

417 Sheoah Boulevard Unit 17, Winter Springs
$505,000
3 Beds ⋅ 3 Baths ⋅ Hickory Grove Twnhms SubDv. ⋅ 32708 Zip Code
Beautifully Upgraded Sofia Model Townhome on a Premium Conservation Lot! Welcome home to this exceptional Sofia Model townhome, featuring one of the community’s most desirable floorplans—with the primary suite conveniently located on the first floor and two additional bedrooms upstairs. This thoughtfully designed layout is ideal for families, first-time buyers, those looking to downsize, or anyone seeking comfortable living with flexibility for guests, a home office, or additional living space. Situated on a premium lot backing to a peaceful conservation/green area, this home offers a wonderful sense of privacy and a tranquil natural backdrop. Inside, numerous builder upgrades and thoughtful custom enhancements create a beautiful blend of modern style, classic elegance, and everyday functionality. Upgrades include enhanced tile, bathrooms, and kitchen finishes, complemented by a custom-designed stair railing that adds a distinctive touch of sophistication. The spacious primary suite features a custom-built walk-in closet, maximizing storage and organization. An Ecobee Smart Thermostat system with Smart Sensors provides efficient, convenient control of the home's comfort while helping manage energy usage. Premium professionally installed ceiling fans in every room provide excellent air circulation and year-round comfort. The home is also professionally wired for rear surround-sound speakers, making it ready for an enhanced entertainment experience. All the rooms have plenty of natural lights! The garage is equally practical, featuring large custom-built ceiling-hung storage, providing valuable additional space while keeping vehicles and everyday belongings organized. Enjoy an outstanding location within Hickory Grove. The community pool and dog park are just down the street, while the Cross Seminole Trail can be easily accessed just outside the community—perfect for walking, jogging, or biking. The Magnolia Square Fountain and Park and The Winter Springs Town Center are both approximately a five-minute walk away, with roughly a dozen food-and-beverage places within walking distance or a short drive away. Central Winds Park is only about a 10-minute drive away. Access to 417 is about 7-minute drive away. With its highly sought-after first-floor primary suite, premium conservation lot, extensive upgrades, custom touches, and exceptional walkable location, this townhome offers a rare combination of comfort, style, privacy, and convenience.

1378 Tarflower Drive, Winter Springs
$499,900
4 Beds ⋅ 3 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
Virtually Staged. Live the Florida lifestyle in the beautiful gated community of Parkstone! This 4-bedroom, 3-bath pool home offers the perfect combination of comfort, convenience, and resort-style living. Spend sunny afternoons relaxing by your own private screened pool, enjoy morning walks or bike rides along the nearby Cross Seminole Trail, or take advantage of Parkstone’s community pool, tennis and volleyball courts, playgrounds, and lakefront dock on Lake Jesup. Even better, lawn care is included through the HOA, giving you more time to enjoy everything the community has to offer. Inside, the open and inviting layout is designed for both everyday living and entertaining, with spacious gathering areas and easy access to the covered outdoor living and pool area. A downstairs bedroom and full bath provide flexibility for guests, a home office, or multigenerational living, while the spacious primary suite upstairs creates a comfortable private retreat. The home has also been thoughtfully cared for with approximately $5,000 invested in new gutters and an extensive underground drainage system, including underground downspouts and dual French drains. Approximately two tons of river rock, a side-yard walkway, refreshed landscaping in 2026, and refreshed tile grout in all three bathrooms add to the home’s move-in-ready appeal. Whether it’s coffee by the pool, an evening walk through the neighborhood, a bike ride on the trail, or a day enjoying the community amenities, 909 Devon Creek offers more than a home—it offers an easy, active Florida lifestyle.

909 Devon Creek Road, Winter Springs
$409,000
3 Beds ⋅ 2 Baths ⋅ Georgetowne Unit 1 SubDv. ⋅ 32708 Zip Code
Welcome to 744 Barrington Circle, a beautifully maintained home nestled in the heart of the sought-after Tuskawilla community of Winter Springs. Tucked away in the desirable Georgetown neighborhood, this 3-bedroom, 2-bath home offers a thoughtful split-bedroom floor plan, soaring vaulted ceilings, abundant natural light, and an inviting blend of indoor and outdoor living. A private courtyard welcomes you into the home, creating a charming space for gardening and enjoying the outdoors. Inside, the open living and dining areas feature beautiful wood floors and vaulted ceilings, creating an airy and spacious feel. The living room flows seamlessly into the Florida room, where three sets of updated sliding glass doors bring the surrounding greenery indoors and open to the tranquil backyard. With a beautiful greenbelt directly behind the property, there are no rear neighbors, offering exceptional privacy. The spacious eat-in kitchen features white cabinetry and stainless steel appliances, while the generously sized primary suite offers double-door entry, plenty of room for a king-size bed, a walk-in closet, built-in vanity, and an ensuite bath with a separate garden tub and shower. The split-bedroom layout provides privacy for everyone, with two additional bedrooms located separately from the primary suite and sharing a full bathroom. Another unique feature is the air-conditioned bonus room within the garage, providing endless possibilities as a home office, gym, workshop, playroom, hobby space, or additional hangout area. Additional updates include new windows and doors, a new garage door, epoxy garage flooring, and fresh exterior paint. Residents of Georgetown enjoy a community pool, while the HOA includes front-yard lawn maintenance, making it easy to enjoy the neighborhood without the added upkeep. The home is also located in a highly desirable school zone, especially Keeth Elementary, and just minutes from Tuskawilla Country Club (membership separate) and Trotwood Park, one of the area's favorite recreational destinations with a splash pad, playground, tennis and pickleball courts, baseball fields, fishing, open green space, pavilions, and picnic areas. Private, peaceful, and perfectly positioned in the heart of Tuskawilla, 744 Barrington Circle offers the space, flexibility, and lifestyle that make this one of Winter Springs' most desirable places to call home.

744 Barrington Circle, Winter Springs
$369,500
3 Beds ⋅ 4 Baths ⋅ Jesups Reserve Twnhms Rep SubDv. ⋅ 32708 Zip Code
Welcome to 412 Blue Bayou, your beautifully refreshed oasis in Jessups Reserve in Winter Springs! This exceptional home stands out with 3 fully en-suite bedrooms and a carpet-free interior featuring laminate flooring throughout and a brand-new stair railing. The downstairs bedroom can be used as a guest bedroom, office or flex space. Complete peace of mind comes standard thanks to major recent capital upgrades, including a ROOF replacement (2022), a brand-new A/C system (2023), and professional garage door maintenance (2024). The primary suite, situated on the third floor for added privacy, features a large walk-in closet, a soaking tub and separate shower, offering a peaceful retreat away from the home's common areas Enjoy effortless Florida living while cooling off in the community pool and soak away the stress of life in the spa. Unwind at the end of the day in three distinct outdoor spaces: a welcoming front porch, a renovated second-floor patio, and a private third-floor balcony. Convenient location is a bonus: walk across the street to Publix when you run out of sugar, check out the live music at Wine Lounge or hit your fitness goals at Crunch Fitness. The main level boasts a bright, open-concept living and dining area, along with a spacious kitchen equipped with stainless steel appliances in excellent condition and a generous breakfast bar; a convenient laundry area is also located on this floor. A spacious two-car garage comes fully equipped with additional smart storage solutions to keep your life organized and functional. Additional bonuses can be found at the Winter Springs Town Center (Aldi, Hiking/Biking Trails and more). Perfectly priced at $369,500, this turn-key property is ready for its next chapter!

412 Blue Bayou Lane, Winter Springs
$399,000
3 Beds ⋅ 3 Baths ⋅ Hickory Grove Twnhms SubDv. ⋅ 32708 Zip Code
Built in 2024 and located in the desirable Hickory Grove community of Winter Springs, this move-in-ready home offers modern style, low-maintenance living, and everyday convenience. Featuring 3 bedrooms, 2.5 bathrooms, and a 2-car garage, the home welcomes you with an open-concept layout filled with natural light. The modern kitchen is designed for both entertaining and everyday living with stainless steel appliances, quartz countertops, and a large center island overlooking the main living area. Upstairs, the spacious primary suite provides a private retreat with an en-suite bathroom and generous closet space, while two additional bedrooms offer plenty of flexibility for family, guests, or a home office. Enjoy maintenance-free living with an impressive list of community amenities just steps from your front door, including a resort-style pool and cabana, playground, dog park, serene green spaces, fountains, and walking paths. Monthly HOA dues include landscaping, irrigation, weed control, exterior paint, roof maintenance, 1GB high-speed internet, and a premium cable package. Conveniently located across the street from Winter Springs Town Center, you’ll have shopping, dining, and everyday conveniences just steps away, all while being near top-rated schools and everything Winter Springs has to offer. With its like-new condition, remaining builder warranty, and sought-after location, this home is ready for its next owner!

1406 Blumberg Boulevard, Winter Springs
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