Single Family Homes for Sale in Winter Springs, FL

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

$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

$2,299,000

3 Beds ⋅ 3 Baths ⋅ Na SubDv. ⋅ 32708 Zip Code

A truly rare find in Winter Springs. This equestrian-friendly, lakefront estate is complete with its own private tennis court, a solid block-constructed horse barn, and room to enjoy every part of the lifestyle. All of this, tucked in a quiet setting that keeps you close to the heart of Orlando, with the added benefit of being just 2 miles from The Geneva School, one of the area’s premier private education options. Originally built in 1964, the home was thoughtfully expanded in 1994, creating a larger, more functional layout while preserving its character. Today it offers over 3,000 SF overlooking the shimmering waters of Little Lake Howell. Enjoy west-facing sunset views framed by mature cypress trees. Host friends for tennis or pickleball right in your backyard. The sizeable horse barn was engineered for exceptional durability, built with block construction and poured concrete for maximum strength. The main home includes a 3-car garage, and the barn adds an oversized carport that can easily double as covered boat storage.

4910 E Lake Drive, Winter Springs

$1,200,000

5 Beds ⋅ 4 Baths ⋅ Tuscawilla SubDv. ⋅ 32708 Zip Code

Experience the beauty of city living on 2.3 acres in the highly desirable city of Winter Springs with no HOA—where open space, natural surroundings, and an equestrian friendly lifestyle come together. This unique property offers the freedom of rural living while remaining conveniently located near the Tuscawilla area. The fully usable acreage is ideal for horses, cattle, or other livestock. If livestock isn’t your preference, the expansive space is perfect for recreational vehicles, racing cars, or other outdoor hobbies. The 5 bedroom, 3 bath home is solid and ready for your personal updates. A standout feature is the 1,500 sq. ft. garage, offering ample room for a boat, race cars, or additional storage. This 2.3 acre parcel is one of the few remaining equestrian friendly properties in the city of Winter Springs, providing a rare combination of comfort, privacy, and natural surroundings. The home is zoned for highly rated Seminole County schools, offering the perfect blend of private country living and excellent educational opportunities. Seller motivated!

1281 Natures Way, 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

$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

$824,900

5 Beds ⋅ 4 Baths ⋅ North Orlando Ranches Sec 02a SubDv. ⋅ 32708 Zip Code

BRAND-NEW CUSTOM HOME IN WINTER SPRINGS WITH NO HOA! Offering approximately 3,184 sq. ft. of air-conditioned living space, this thoughtfully designed 5-bedroom custom home combines custom finishes, flexible multigenerational living and upgrades rarely found in typical new construction—all without the restrictions or monthly fees of an HOA. The first floor features a private in-law suite with its own full bathroom and separate laundry facilities, creating an ideal arrangement for multigenerational living, extended family or guests. The home also includes a second, full-size laundry room featuring built-in cabinetry, a quartzite countertop and an undermount stainless-steel utility sink. At the heart of the home is a beautifully finished kitchen featuring upgraded quartz countertops and a high-end LG appliance package, opening to the spacious great room for an easy flow between cooking, dining and entertaining. Ceiling fans have already been installed in all bedrooms, the great room and screened lanai. The primary suite was designed as a true retreat, highlighted by a custom wet room, private water closet, upgraded quartz countertops and custom built-in shelving. Primary bedroom also features two massive walk in closets with Custom built-in closet shelving. Custom built-in closet shelving is also featured throughout all the bedrooms in the main home. Additional designer finishes include quartz countertops in the in-law bath and powder room, leathered black granite in the upstairs guest bathroom, and quartzite in the main laundry room. Adding even more flexibility is the approximately 22’ × 11’ fifth bedroom above the garage, offering approximately 242 sq. ft. of additional living space and an excellent option for a bonus room, home office, media room or guest space. Two tankless water heaters provide abundant hot water throughout the home, while an impressive 400-amp electrical service provides substantial capacity for current and future needs, including EV charging, an RV connection, workshop or welding equipment, or other high-demand electrical additions. Outdoor living was equally well planned. The screened rear lanai is complemented by two additional paver patios, creating multiple areas for outdoor dining, grilling, relaxing and entertaining. The wooded lot extends back to a peaceful creek, offering plenty of space to explore, enjoy nature, or simply grab a fishing pole and unwind in your own backyard. An oversized paver driveway provides generous additional parking. Even the garage was designed beyond standard dimensions. The oversized two-car garage provides additional width and usable space, allowing plenty of room to comfortably open vehicle doors with two cars parked inside while still providing valuable additional storage space. From the first-floor in-law suite and dual laundry facilities to the fifth bedroom/flex space, custom wet room, upgraded stone surfaces, high-end appliance package, dual tankless water heaters, 400-amp electrical service, oversized garage and driveway, and multiple outdoor living areas, this custom new-construction home offers an exceptional combination of quality, flexibility and functionality in Winter Springs. Brand new, custom built and ready for its first owner.

628 Silver Creek 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

$749,000

5 Beds ⋅ 4 Baths ⋅ Northern Oaks SubDv. ⋅ 32708 Zip Code

Welcome to 957 Talon Place, a 2021 Dream Finders home in Northern Oaks, a small, tucked-away community right on the Winter Springs–Oviedo line. It offers 5 bedrooms, 3.5 bathrooms and more than 3,200 sq ft on a 0.2-acre lot with room for a pool. A paver walkway and driveway lead to the arched covered entry. Inside, light wide-plank flooring and wrought-iron stair balusters set a clean, modern tone. The open great room flows into the dining area and kitchen, and sliding glass doors open to a covered, screened lanai overlooking the fenced backyard. The kitchen is made for gathering, with an oversized island, a stainless farmhouse sink, marble countertops, a herringbone tile backsplash, a stainless chimney hood and built-in double wall ovens. A full bedroom and bathroom on the main level give guests or a home office their own space. Upstairs, a spacious loft adds a second living area. The generous primary suite and the other bedrooms feature large walk-in closets. Plantation shutters, abundant natural light and plenty of storage run throughout the home. The home also comes with smart extras: paid-off solar panels and two A/C units for efficient, zoned comfort. It is newer construction, move-in ready and in a hard-to-find location. Schedule your private showing today!

957 Talon Place, Winter Springs

$699,900

4 Beds ⋅ 3 Baths ⋅ Barrington Estates SubDv. ⋅ 32708 Zip Code

Tucked away on a cul-de-sac in the gated community of Barrington, this stunning 4-bedroom, 3-bath, 3 car garage home is truly turnkey ready. Situated on an oversized lot, the property features a huge gazebo in the backyard with a NEW ROOF at same time as the home (2022), creating the perfect setting for entertaining family and friends. As you enter, you are welcomed by gorgeous hardwood flooring that flows throughout the home. The fourth bedroom, currently used as a home office at the front, offers built-in cabinetry, providing an ideal work-from-home environment. Additional upgrades include plantation shutters, crown molding, and fresh interior paint, adding elegance and style throughout. The heart of the home is the beautifully updated kitchen, complete with stainless steel appliances (2019), quartz countertops, and 48-inch cabinetry, offering both functionality and abundant storage. The spacious owner's suite features a walk-in closet with custom built-in cabinetry and a fully updated en-suite bath showcasing a newer vanity, private water closet, relaxing garden tub, and walk-in shower. The split-bedroom floor plan provides privacy for family and guests, while the open living spaces are perfect for both everyday living and entertaining. Step outside to enjoy the oversized backyard, where the custom gazebo creates a private outdoor retreat for year-round enjoyment. Other amenities include newer HVAC (2021), E-charging station in garage, Large floored attic space, Exterior painted (2020) and additional pavered parking pad for all the extra parking you could dream of. Conveniently located near top-rated schools, shopping, dining, and 417, this exceptional home offers the perfect combination of comfort, style, and location. Don't miss your opportunity to make this Barrington beauty your next home!

475 Verandah Court, 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

$669,900

4 Beds ⋅ 3 Baths ⋅ Barrington Estates SubDv. ⋅ 32708 Zip Code

Virtually Staged. Welcome to this stunning 4-bedroom, 3-bathroom home nestled in the gated community of Barrington Estates! A dedicated office or study room greets you at the entrance, perfect for working from home. The kitchen features brand new quartz countertops, a center island, and a breakfast bar that opens seamlessly to the living room — ideal for everyday living and entertaining. The primary suite is a true retreat, complete with a sitting area, separate closets, dual sinks, a garden tub, and a walk-in shower with dual shower heads. Vinyl flooring flows throughout the home. Upstairs, a large bonus room with a closet offers endless possibilities as a second family room, media room, or additional office. Step outside to a covered patio overlooking a spacious, grassy backyard — perfect for relaxing or entertaining. Barrington Estates offers a peaceful, tree-lined setting with a private gated entrance and community playground. Ideally located just off SR-434, this home is less than 20 minutes from UCF, Research Park, and an abundance of shopping and dining options. Don’t miss out on this move-in ready home!

1496 Wescott Loop, Winter Springs

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