Winter Springs Real Estate

Homes for Sale with a Pool in Winter Springs, FL

Welcome to your dedicated resource for homes for sale with a pool in Winter Springs, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Winter Springs, FL agents, Zen Home Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

< Back to all Homes for Sale in Winter Springs, FL

Be the First to Know About New Winter Springs Homes

Stay ahead with real-time updates — no searching required.

See Homes Before Everyone Else

Winter Springs Real Estate Map Search

All Homes for Sale with a Pool in Winter Springs, FL

1112 Orange Avenue, Winter Springs
$3,700,000
5 Beds ⋅ 7 Baths ⋅ Lake Jessup SubDv. ⋅ 32708 Zip Code
Opportunities like this are almost impossible to find in Central Florida. Situated on 5.33 pristine lakefront acres with no HOA, this extraordinary estate is commercially zoned, creating a unique opportunity for a variety of potential business uses, including a luxury wedding venue, private event space, corporate retreat, boutique hospitality concept, or an exceptional live-work estate. With its breathtaking setting, grand architecture, and resort-style amenities, the property offers a level of versatility rarely available in today's market. Inspired by the elegance of the Italian countryside, the residence makes a lasting first impression with a dramatic front waterscape, lush gardens, and timeless architectural details. Inside, guests are welcomed by a grand foyer featuring exquisite marble finishes and a spectacular custom-painted 24-karat gold dome. Designed for both entertaining and everyday luxury, the expansive living spaces showcase panoramic views of beautiful Lake Jessup, soaring ceilings, stunning chandeliers, and a grand marble fireplace. The thoughtfully designed "H" floor plan encompasses more than 8,000 square feet of air-conditioned living space, offering five spacious bedrooms and six-and-a-half bathrooms, all conveniently situated on a single level. The primary suite is a true private retreat, featuring eight sets of French doors opening directly to the pool and lakefront, a custom-designed closet that doubles as a safe room, and a spa-inspired bathroom complete with a tranquil garden retreat. The gourmet chef's kitchen is equipped with top-of-the-line appliances, custom cabinetry, and an oversized walk-in butler's pantry designed to accommodate large-scale entertaining. Additional luxury amenities include a temperature-controlled wine cellar, private movie theater, dedicated nanny or guest quarters, and a six-car garage with extensive attic storage. Outside, the estate transforms into a private resort. A spectacular sports pool with multiple water features serves as the centerpiece, complemented by a summer kitchen, wet bar, outdoor fireplace, and expansive covered veranda overlooking the serene waters of Lake Jessup. Whether hosting elegant weddings, unforgettable events, corporate gatherings, or private family celebrations, the setting is simply unmatched. Combining custom craftsmanship, Tuscan and Greek-inspired design elements, commercial zoning flexibility, and an irreplaceable waterfront location, this remarkable estate offers a truly rare opportunity to own one of Central Florida's most unique properties. Schedule your private tour today to experience the endless possibilities and extraordinary lifestyle this one-of-a-kind property provides.

1112 Orange Avenue, Winter Springs

1447 Bird Road, Winter Springs
$2,495,000
6 Beds ⋅ 6 Baths ⋅ Talis Crossing SubDv. ⋅ 32708 Zip Code
A RARE OPPORTUNITY, NOW EVEN MORE EXCEPTIONAL. PRICE IMPROVEMENT AND ADDITIONAL BUILDABLE LOT INCLUDED. Some homes are simply purchased. Others are reserved for those who have earned the privilege of owning something truly extraordinary. Privately nestled in Winter Springs, this brand-new, 8,000 SF architectural estate represents a level of luxury, sophistication, and exclusivity rarely offered. Now, with a compelling price improvement, the seller is including the additional buildable front parcel, creating an extraordinary opportunity to establish a private compound, develop a separate residence, or preserve the additional acreage as an enduring sanctuary of privacy and seclusion. The experience begins at custom glass French doors opening to an exquisite marble mosaic foyer, setting the stage for the remarkable craftsmanship throughout. Beyond, a magnificent great room rises to 16-foot ceilings, where celestial windows invite natural light to dance across refined finishes, a panoramic fireplace, and a custom bookcase wall. An extraordinary 18-foot sliding glass wall effortlessly dissolves the boundary between indoors and out, revealing 1,125 SF of covered outdoor living designed for unforgettable entertaining. At the heart of the residence, a statement 13-foot island anchors a chef's kitchen appointed with a complete GE Café appliance suite, pot filler, custom pet station, and discreet butler's pantry. A sophisticated marble and terrazzo wet bar provides an elegant setting for intimate gatherings and grand celebrations alike. Thoughtfully designed for those who value personal space, two lavish primary suites occupy opposite wings of the residence, each offering a private retreat complete with an indulgent spa-inspired wet room, soaking tub, curbless entry, and four-port shower system. A private theater, dedicated fitness studio, and two distinguished executive offices framed in architectural storefront glass complete a lifestyle where productivity, wellness, and leisure exist in perfect harmony. Beyond the glass, a striking white quartz swimming pool with sun shelf becomes the centerpiece of an outdoor oasis designed for both tranquil afternoons and sophisticated evenings. Behind the beauty lies uncompromising substance, including a 50-year commercial-grade TPO roof, four-zone climate control, dual tankless water heaters, and a three-car garage. What makes this offering truly remarkable is not simply the residence itself, but the land and possibilities that now accompany it. With the additional buildable front parcel included, the next owner has the rare privilege of deciding how this estate evolves, whether through future development, a multigenerational compound, or the preservation of an exceptionally private setting. An architectural statement. An extraordinary estate. An opportunity made even more compelling by the seller's recent price improvement. For those who have made their mark and expect their home to reflect it, this is a residence without compromise. Private showings by appointment.

1447 Bird Road, Winter Springs

609 Viana Court, Winter Springs
$925,000
5 Beds ⋅ 4 Baths ⋅ Seville Chase SubDv. ⋅ 32708 Zip Code
Space, privacy, and exceptional features define this impressive 5-bedroom, 3.5-bath POOL HOME in the GATED Seville Chase community of Winter Springs! Situated on a generous .67-ACRE CORNER LOT in a quiet CUL-DE-SAC, this estate-style home offers over 3,500 SQUARE FEET of thoughtfully designed living space, a ***FULLY PAID OFF TESLA SOLAR SYSTEM with FOUR POWERWALLS*** - leaving this large home virtually free of any electric bill, and a private backyard retreat. Major improvements include UPDATED A/C’s (2021 & 2026), and a hybrid water heater (2019). The heated SALTWATER POOL & SPA were resurfaced with PebbleTec in 2019, along with a new pool pump. Beautiful curb appeal welcomes you with mature landscaping, ample parking in the paver driveway, and a side-entry 3-CAR GARAGE. Inside, high ceilings, crown molding, decorative ceiling details, abundant natural light, and TILE & WOOD FLOORS create a warm and inviting atmosphere. Designed to live like a single-story home, the versatile floor plan offers formal and family living spaces, a DEDICATED OFFICE, and a second-floor BONUS ROOM above the garage, ideal for a media room, game room, or additional flex space. At the heart of the home, the spacious kitchen features BUILT-IN STAINLESS STEEL APPLIANCES, a GAS COOKTOP, ample cabinetry, and easy access to the surrounding living and dining areas, making everyday living and entertaining effortless. The PRIMARY SUITE is a private retreat with a spacious en-suite bath and THREE CLOSETS, including two walk-ins. Two additional bedrooms share a convenient JACK & JILL BATH, while a fourth bedroom enjoys access to another full bath. Step outside and into your own backyard oasis, where a paver lanai and pool deck surround the heated pool and spa where you can lounge, dine, and entertain. Mature trees and the oversized lot provide exceptional privacy and room to enjoy the outdoors. Additional features include a WATER SOFTENER SYSTEM and energy-efficient solar power with battery storage. Seville Chase offers the privacy of a gated neighborhood in a fantastic Winter Springs location, convenient to shopping, dining, parks, recreation, and TOP-RATED SCHOOLS, including Sterling Park Elementary, South Seminole Middle, and Winter Springs High. With its flexible living spaces, impressive energy features, and private backyard, this is a home that truly has room for it all. Call today to schedule a tour and let us say WELCOME HOME!

609 Viana Court, Winter Springs

1522 Eagle Nest Circle, Winter Springs
$835,000
4 Beds ⋅ 4 Baths ⋅ Glen Eagle Unit 4 SubDv. ⋅ 32708 Zip Code
New Roof being installed!! Ideally located in the highly desirable Glen Eagle community of Tuscawilla, this Von Jacobs pool home offers a versatile three-way split floor plan with four bedrooms and three and a half bathrooms, providing plenty of space for family, guests, or a home office. The layout includes formal living and dining rooms, while the kitchen opens to the family room and breakfast nook for comfortable everyday living and entertaining. The remodeled kitchen features wood cabinetry, an expanded pantry, quartz countertops, and a wet bar area. Both secondary bathrooms have also been remodeled, while the primary bath offers an opportunity to customize to your taste. Outside, enjoy Florida living around the recently resurfaced pool (2024), complete with a new pool pump (2024) and electric heater for extended seasonal enjoyment. The spacious screened enclosure was re-screened in 2024, creating an inviting setting for relaxing or entertaining. A generous side yard and three-car garage add even more appeal. Major updates include a new water heater (2026), new garage doors (2026), replumb, and AC (2019). Don’t miss this opportunity! Glen Eagle puts you close to the Tuscawilla Country Club and its 18-hole golf course, along with several of Central Florida’s sought-after private schools, including The Geneva School, Trinity Preparatory School, The Master's Academy, and St. Luke's Lutheran School. Grab your golf cart and come take a look—this Glen Eagle gem won’t last long!

1522 Eagle Nest Circle, Winter Springs

337 Twelve Oaks Drive, Winter Springs
$785,000
5 Beds ⋅ 4 Baths ⋅ Winding Hollow Unit 5 SubDv. ⋅ 32708 Zip Code
WELCOME HOME to 337 Twelve Oaks Drive! This stunning Wisteria II Model offers 5 bedrooms, 3.5 bathrooms, and 3,660 square feet of beautifully maintained living space, perfectly positioned on an oversized .25-acre premium waterfront lot in the sought-after Winding Hollow community of Winter Springs. From the moment you arrive, you'll appreciate the lush landscaping, exceptional curb appeal, and pride of ownership throughout this immaculate home. Inside, an abundance of thoughtful upgrades and elegant finishes create the perfect blend of comfort, style, and functionality. The renovated gourmet kitchen is truly the heart of the home, featuring floor-to-ceiling custom cabinetry, quartz countertops, a large center island, stainless steel appliance package, stylish tile backsplash, and a water filtration system. The spacious kitchen opens beautifully to the expansive family room, creating an ideal space for everyday living and entertaining. Additional upgrades include all-new windows and doors, beautiful wood-plank ceramic tile flooring, plantation shutters, and newer attic insulation, providing both style and improved energy efficiency. The first floor features a spacious primary suite, a versatile den/office, formal living room, formal dining room, and a huge family room with serene views of the private pool, expansive patio, and tranquil pond. The primary suite provides a peaceful retreat with plenty of space and privacy. Upstairs, you'll find three additional generously sized bedrooms, each offering large closets, along with two full bathrooms and an impressive 17' x 24' game room—perfect for a media room, playroom, home gym, or additional entertaining space. The three-car garage provides abundant storage and parking, and features a custom garage floor coating for a polished, durable finish. Step outside and experience your own private oasis. The sparkling pool, spacious patio, lush landscaping, and peaceful waterfront setting create the perfect backdrop for relaxing mornings, afternoon swims, and memorable gatherings with family and friends. Located in desirable Winding Hollow, this home offers an exceptional Winter Springs lifestyle with walking trails, community park areas, close proximity to top-rated Seminole County schools, shopping, Winter Springs Town Center, restaurants, Central Winds Park, the Seminole Trail, and more. With its premium waterfront setting, private pool, spacious floor plan, three-car garage, extensive upgrades, and beautifully appointed living spaces, 337 Twelve Oaks Drive is more than just a home—it’s a lifestyle!

337 Twelve Oaks Drive, Winter Springs

864 Bentley Green Circle, Winter Springs
$679,000
4 Beds ⋅ 3 Baths ⋅ Bentley Club At Bentley Green SubDv. ⋅ 32708 Zip Code
Welcome to 864 Bentley Green Circle, a move-in-ready luxury sanctuary situated on a quiet cul-de-sac lot in Winter Springs. Offering 4 bedrooms, 3 full bathrooms, and over 2,200 square feet of meticulously updated living space, this home seamlessly blends sophisticated interior accents with private, resort-style outdoor living. WHAT’S SPECIAL GOLF COURSE ACCESS & VIEWS | RESORT-STYLE GAS-HEATED SALTWATER POOL & SPA | 4 HARDWOOD BEDROOMS | UPDATED SPA BATH | CUSTOM BUILT-INS & WINDOW SEATING | GOURMET KITCHEN WITH GRANITE COUNTERTOPS | CUSTOM GAS BLACK MARBLE FIREPLACE | HIGH CEILINGS & CUSTOM CROWN MOLDING Arrive via a grand circular drive centered around a professionally landscaped island, featuring a newly updated limestone walkway that creates an elegant entryway. Inside, the light-filled open floor plan boasts high ceilings, newly painted walls, transoms, interior glass doors, and smart recessed lighting with nightlight mode. The main living area is anchored by a stunning custom black marble gas fireplace and expansive sliding glass doors that open to the lanai. A formal dining room offers luxury vinyl flooring, custom crown molding, and a statement chandelier, while a dedicated lounge/den provides cozy custom built-ins and window seating. The gourmet kitchen comes complete with granite countertops, tile flooring, newly installed stainless-steel appliances, including a new refrigerator, and convenient access to a laundry area with a recently purchased large-capacity washer and dryer set. The main-level owner's retreat serves as a true sanctuary, featuring hardwood floors, a sitting area, built-in electric wall fireplace, space for a coffee station, spacious walk-in closet, and a completely updated spa bath with a deep soaking tub and oversized glass shower. Upstairs, three additional hardwood-floored bedrooms include one configured as an executive home office with scenic views of the nearby pond and golf course. Step outside into your private backyard oasis, highlighted by a gas-heated saltwater pool and spa designed for year-round enjoyment. The outdoor retreat also features a newly renovated screen enclosure, updated pool equipment, and multi-color pool lighting. Relax beneath the custom covered lanai showcasing a real wood ceiling, ceiling fan, and custom recessed lighting—complete with included patio furniture and an exterior TV. The grounds are surrounded by manicured landscaping, lush palm trees, privacy hedges, and a tranquil side-yard "Zen garden" designed to attract butterflies and hummingbirds. Adding to the lifestyle appeal, the property offers private access to the golf course, providing convenient access to Tuscawilla Country Club and its array of amenities. With a separate club membership, residents can enjoy amenities such as a lap pool, fitness center, dining, social events, golf, and more. Country club membership is not included with the property and must be purchased separately. Rounding out this exceptional property are dual driveways and a 2-car workshop garage equipped with built-in storage shelving and a 240-amp EV charging station.

864 Bentley Green Circle, Winter Springs

4161 Aldergate Place, Winter Springs
$664,000
4 Beds ⋅ 3 Baths ⋅ Forrest Creek Estates SubDv. ⋅ 32708 Zip Code
Welcome to Forrest Creek Estates, an exclusive enclave of just 37 homes where neighbors become family and a true sense of community is part of everyday life. Tucked within an established Winter Springs neighborhood, this charming community offers a rare combination of tranquility, connection, and convenience. This beautifully renovated residence has been thoughtfully designed and lovingly maintained by its owners, blending modern style with timeless character and comfortable Florida living. From the moment you arrive, the home's curb appeal makes a lasting impression. An elegant white-brick entry, charming architectural windows, stately four-pane glass front door, and graceful Roubini palms create a warm and inviting welcome. Step inside to a bright, beautifully appointed foyer filled with natural light and a refined neutral palette. To the right of the entry, the formal living room offers exceptional versatility and can easily serve as a home office, library, sitting room, or additional gathering space. The heart of the home is the spectacular chef's kitchen, featuring custom white cabinetry, stylish hardware, stacked geometric white tile backsplash, large stainless-steel sink, state-of-the-art appliance package, and an impressive 4-foot island with abundant storage and luxurious white quartzite countertops. A separate pantry with generous shelving provides convenient storage for cooking essentials and entertaining supplies. The kitchen flows effortlessly into the spacious family room, creating an ideal setting for everyday living and entertaining. Luxury plank flooring, neutral earth tones, and a dramatic wood-burning fireplace surrounded by white brick add warmth and architectural character. The open and inviting layout provides an easy connection between the kitchen, family room, and outdoor living spaces. The first-floor primary suite offers a private retreat with a calming ivory palette, natural wide-plank flooring, and beautifully dressed windows. The updated primary bath features a distinctive gray vanity, charming circular mirror, and luxurious walk-in shower finished in smooth white tile with multiple shower heads for a spa-inspired experience. Upstairs, three generously sized bedrooms and a beautifully updated shared bath provide plenty of flexibility for family, guests, home office needs, or personal space. The thoughtfully designed floor plan offers both comfortable gathering spaces and private retreats. Significant improvements provide added peace of mind, including a 5-ton AC installed in 2023, architectural roof installed in 2025, complete kitchen, bathroom, and flooring renovation completed in 2022, saltwater pool resurfaced with new pump and skimmer in 2023, and water heater replaced in 2022. These substantial updates allow you to enjoy the home's exceptional style and lifestyle with confidence. Step outside through the sliding doors and discover your own private outdoor retreat. The covered lanai, finished with a beautiful wood ceiling, overlooks the sparkling saltwater pool and surrounding flower beds. Designed for both relaxation and entertaining, this inviting outdoor space is perfect for morning coffee, afternoon swims, weekend barbecues, or gathering with friends on warm Florida evenings. Location adds another layer of appeal. Situated less than one mile from shopping and dining, you'll enjoy convenient access

4161 Aldergate Place, Winter Springs

1105 Shadowbrook Trail, Winter Springs
$650,000
4 Beds ⋅ 3 Baths ⋅ Winding Hollow Unit 4 SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully updated 4-bedroom, 3-bathroom pool home in Winding Hollow, offering over 2,500 square feet of living space, a split-bedroom floor plan, and a 3-car garage! A double-door entry welcomes you inside, where fresh paint throughout and new flooring create an inviting setting. Two separate living spaces—a formal living room and a spacious family room—provide flexibility for entertaining and everyday living, while a formal dining room and a casual breakfast area provides space for every occasion. The updated kitchen features new cabinetry, granite countertops, stainless steel appliances, an island, breakfast bar seating, an updated backsplash, and a dedicated coffee and wine bar. Whether preparing a meal or hosting a gathering, there is plenty of room to cook, serve, and connect. Privately situated on the opposite side of the home from the guest bedrooms, the spacious primary suite features its own sitting area with French doors—an ideal space for a nursery, home office, or quiet retreat—along with access to the lanai. The primary bathroom includes dual vanities with updated countertops, a soaking tub, a separate shower, and a private water closet. Spacious secondary bedrooms share an updated Jack-and-Jill bathroom with a tiled tub/shower combination, while the fourth bedroom enjoys convenient access to the updated third full bathroom, complete with a shower and direct pool access. Step outside to an expansive covered lanai beneath the home’s shingled roof, providing generous sheltered space for outdoor dining and relaxing. The screened-in pool features a waterfall sprayer, while mature landscaping and a partially fenced backyard provide an inviting backdrop with green space beyond the pool enclosure. Additional highlights include an interior laundry room, extra attic storage, south-facing front exposure, and a roof and Trane A/C system installed in 2018. Conveniently located near shopping, dining, schools, Winter Springs Town Center, and area recreation, this home combines thoughtful updates, spacious gathering areas, and inviting outdoor living. Schedule your private showing today! Buyer and buyer’s agent to independently verify all property information, including measurements, square footage, room dimensions, schools, permits, and any other details deemed important to the buyer.

1105 Shadowbrook Trail, Winter Springs

216 Tavestock Loop, Winter Springs
$605,000
5 Beds ⋅ 2 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
Enjoy waterfront views and your own private pool in this spacious 5-bedroom, 2-bath home located in the highly sought-after gated community of Parkstone in Winter Springs. Perfectly positioned with tranquil pond views, this home offers a desirable three-way split floor plan, open living spaces, and an ideal blend of comfort, functionality, and outdoor living. Inside, you’ll find luxury vinyl plank flooring throughout the main living areas, a beautifully updated kitchen featuring granite countertops, refinished cabinetry, and a stylish backsplash, along with tastefully remodeled bathrooms showcasing shaker-style vanities, updated fixtures, and wood-look tile flooring. Energy-efficient upgrades include Low-E double-hung windows, an updated roof (2021), Carrier HVAC system, LED lighting, a whole-house water filtration system, two mini-split air conditioning systems (2025), and an energy-efficient year-round. The backyard is also been fully fenced, creating a private space for pets, play, and outdoor enjoyment. Step outside to your own backyard retreat featuring a sparkling pool, relaxing spa, and picturesque water views. Whether you’re entertaining guests or enjoying a quiet evening watching the sunset over the pond, this outdoor space is sure to impress. Additional features include pool deck speaker pre-wiring and a 220-volt outlet ready for an electric vehicle charger. Parkstone residents enjoy an exceptional lifestyle with lawn maintenance included in the HOA, a community pool, fishing pier, tennis courts, playgrounds, walking trails, scenic ponds, and gated security. The community borders the Cross Seminole Trail and is just a short walk to Central Winds Park and the dog park. Located in Seminole County with highly rated A-rated schools and convenient access to shopping, dining, and major roadways, this home truly offers the best of Florida living. Don’t miss your opportunity to own this exceptional waterfront home in one of Winter Springs’ most desirable communities!

216 Tavestock Loop, Winter Springs

Start Your Search

How much is your home worth?

Get instant property value now!