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

$3,799,000

7 Beds ⋅ 7 Baths ⋅ Dunmar Estates SubDv. ⋅ 32708 Zip Code

Rare opportunity to own a private estate in the heart of Central Florida. Situated on nearly 6 acres in the prestigious Dunmar Estates community of Winter Springs, this exceptional property is fully fenced BY METAL FENCE AND SOLID WALL FENCE FROM 6ft to 10 ft and gated, offering outstanding privacy, security, and a true retreat-like setting. The main residence features over 12,000 square feet of living space, including 7 bedrooms, multiple living and entertaining areas, and a unique indoor heated pool that can be enjoyed year-round regardless of weather. Expansive grounds and mature landscaping create a peaceful and secluded environment rarely found in today’s market. A standout feature of the property is its two separate Mother-in-Law Suites, ideal for multigenerational living, extended family, long-term guests, caregivers, private offices, or flexible living arrangements. Additional amenities include a tennis court, circular driveway, 6-car garage, and abundant outdoor space, offering endless opportunities for customization, renovation, and creating a truly one-of-a-kind family compound. Conveniently located just minutes from top-rated schools, shopping, dining, and major highways, this estate combines the tranquility of private country-style living with the convenience of city access. A rare offering with exceptional space, privacy, and unlimited potential.

593 Dunmar Circle, Winter Springs

$2,625,000

6 Beds ⋅ 6 Baths ⋅ Talis Crossing SubDv. ⋅ 32708 Zip Code

Discover the pinnacle of secluded luxury in this brand-new, 8,000 SF estate, nestled in picturesque Winter Springs. From the moment you arrive, the custom glass French entry doors hint at the artistry within. Stepping into the grand foyer, you are greeted by statement marble and mosaic flooring that sets a tone of elegance, a design narrative that flows seamlessly throughout the home. Designed for both grand-scale entertaining and intimate daily life, the main living spaces are simply breathtaking. The great room soars with 16-foot ceilings and celestial windows, anchored by a stunning custom fireplace and bookcase display. A bank of 18-foot sliding glass doors dissolves the line between indoors and out, opening to a sprawling 1,125 SF covered patio. The chef’s kitchen is a masterpiece of form and function, featuring a 13-foot island, floor-to-ceiling cabinetry, a pet-feeding station, electric vehicle garage hookup, and a full suite of WiFi-enabled GE Cafe appliances, including a double wall oven and a 48-inch refrigerator. The home offers a versatile and luxurious layout for multi-generational living or visiting guests, highlighted by two distinct primary suites. One wing is dedicated to a private retreat with two walk-in closets, separate vanities, and a spa-inspired wet room with a freestanding tub and a four-port shower system. On the opposite side of the home, a second primary suite offers equal luxury with a massive walk-in closet and its own spa-like wet room, ensuring complete privacy for all. Beyond the main living areas, discover a wealth of flexible spaces tailored to a modern lifestyle. A dedicated movie theater or fitness center is pre-wired for the ultimate audio-visual experience, while two separate offices with storefront glass windows provide inspiring workspaces. A butler’s pantry/kitchen, wet bar with a beverage fridge, and a flexible flex room with a half-bath complete the impeccably designed interior. Outside, your private paradise awaits upon the spacious 1-acre parcel. The pavered pool deck surrounds a white quartz pool with a sun shelf and bubbler, all secured by a sleek black metal fence. Every detail has been considered, from the 150-gallon propane tank servicing the future summer kitchen and pool heater to the 4-zone HVAC, a commercial grade 50-year life-span TPO roof and two tankless water heaters for ultimate comfort. This is more than a home; it is a fully realized vision of eloquent Florida living.

1447 Bird Road, Winter Springs

$2,399,000

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

$1,120,000

5 Beds ⋅ 5 Baths ⋅ Reserve At Tuscawilla Ph 1 The SubDv. ⋅ 32708 Zip Code

Privately set within the exclusive gated community of Tuscawilla Reserve, this stunning custom estate delivers over 4,000 square feet of light-filled, designer-inspired living centered around a spectacular kitchen and family room that truly defines the home. With 5 bedrooms, 5 full baths, plus a private office/bonus room, this residence offers exceptional versatility for today’s lifestyle. Sleek wood flooring flows seamlessly throughout the main living areas, complementing the home’s open, modern design. The impressive kitchen and family room feature soaring two-story ceilings and expansive windows, framing views of the outdoors and pool area while filling the space with natural light—creating an inviting setting for both everyday living and elevated entertaining.The chef’s kitchen is a true centerpiece, anchored by JennAir appliances, including double ovens, convection oven, and microwave combo, along with a massive granite-topped island—all coming together to create a stunning focal point that anchors the kitchen and family room. Custom details further enhance the design, including a built-in buffet with integrated wine refrigerator and an oversized walk-in pantry. The thoughtfully designed floor plan offers incredible flexibility, including an upstairs retreat featuring an additional bedroom, full bath, and expansive flex space that can easily function as a media room, playroom, or second private office.Step outside to your private backyard oasis featuring a sparkling pool and spa with a new heater, surrounded by mature landscaping and a fully fenced yard, offering both openness and privacy. Additional highlights include a 3-car side-entry garage, whole house water softener and expansive living areas that support a variety of lifestyle needs. Ideally located near the Seminole Trail and just minutes from Tuscawilla Country Club, residents enjoy golf, tennis, swimming, and vibrant social amenities. Zoned for highly regarded Seminole County schools, this home offers both lifestyle and long-term value. Golf carts are a popular mode of transportation within the community, adding to the charm and convenience. A seamless blend of modern design, natural light, and elevated living—this is Tuscawilla Reserve at its finest. Schedule your private showing today and experience this exceptional home in person.

149 Cherry Creek Circle, Winter Springs

$1,049,000

4 Beds ⋅ 3 Baths ⋅ Bahama Ranches SubDv. ⋅ 32708 Zip Code

Mid-Century Modern Paradise!! A Beautiful, well-designed home with spectacular architecture offering privacy, space, and long-term versatility on a rare 2.22-acre lot with RV/Toy parking—delivering exceptional value in this area. A separate in-law or guest suite features its own exterior entrance and full bathroom, ideal for multigenerational living, a private office, studio, or extended stays. The main living areas are sprawling, thoughtfully arranged with strong natural light and a functional flow for everyday living and a large Loft for entertaining, office or hobbies. The large primary suite includes a spacious en-suite bath and walk-in closet. Bedrooms two and three are oversized, each with walk-in closets; one includes a hidden play loft/ adventure nook accessible through the Narnia style closet access. The expansive property also includes a detached casita in the backyard, currently used as a workshop, with clear potential to be converted into a guest home, rental unit, or art studio. Located on a quiet street in an established Winter Springs neighborhood, with convenient access to top-rated schools, shopping, dining, and major commuter routes. Concessions considered with the right scenario. Buyer and buyer’s agent to verify all information. Both owners are licensed real estate agents.

120 E Bahama Road, Winter Springs

$989,000

5 Beds ⋅ 5 Baths ⋅ Tuscawilla Unit 14b SubDv. ⋅ 32708 Zip Code

Welcome to this beautifully reimagined 5-bedroom, 3 full bath, 2 half bath pool home located in the highly sought-after Chelsea Woods community of Tuscawilla. Blending timeless architectural character with extensive modern updates, this move-in ready home offers exceptional space, style, and functionality throughout. Step inside to discover expansive living areas designed for both everyday living and entertaining, including a large formal living room with a stunning brick fireplace, a spacious family room with a second fireplace, formal dining room, and an oversized bonus space ideal for a home office, playroom, media room, or flex living area. The completely remodeled kitchen is a true centerpiece, featuring quartz countertops, brand-new appliances, custom two-tone cabinetry, open shelving, designer finishes, and a stylish bar area perfect for hosting. A spacious laundry room with a convenient butler’s pantry area adds additional storage and functionality. Downstairs also includes two beautifully updated half bathrooms. Upstairs, all five bedrooms offer generous space and natural light, along with three fully renovated bathrooms, including a Jack-and-Jill layout. The expansive primary suite serves as a private retreat with soaring ceilings, a luxurious freestanding soaking tub, oversized walk-in shower, dual vanities, and elevated designer finishes throughout. Additional updates include a newer roof in 2023, both A/C units replaced 12/2025, wood-look tile flooring throughout the lower level, and luxury vinyl plank flooring upstairs. Outside, enjoy Florida living at its best with a covered and screened lanai overlooking the sparkling pool and spacious patio area—perfect for relaxing or entertaining year-round. Located in one of Tuscawilla’s most desirable neighborhoods and zoned for top-rated Seminole County schools, this rare fully updated home combines architectural charm, modern design, and an unbeatable location. Homes with this level of renovation, space, and character rarely become available in Chelsea Woods. Call today to schedule your private showing.

1815 Seneca Boulevard, Winter Springs

$850,000

4 Beds ⋅ 3 Baths ⋅ North Orlando Ranches Sec 01 SubDv. ⋅ 32708 Zip Code

Motivated Seller! This custom 4 bedroom, 2.5 bathroom pool home nestled on a gated 2.6 acres in the sought-after Ranchlands Community is a must see! The 40ft long front porch overlooks the nature's paradise with views you must see to appreciate. Oak trees and mature landscaping line the private entrance and make up the bulk of this serene property. An entertainer's paradise features pool with custom waterfall, poolside cabana with fireplace, bar and grill, pergola leading to cabana, romantic gazebo with power, nature trails, tri-level balcony, covered back porch (29x12) overlooking pool and 2 story playhouse/gym. You'll notice the craftmanship and attention to detail throughout the property with custom carpentry and designer touches both inside and out. Kitchen (19x12) with lots of granite counter space boasts solid wood cabinets, modern hardware, stainless steel appliances with range hood, flat top range, stone backsplash, rolling island, and pendant lighting over bar seating while overlooking the beautiful pool oasis. The owner's suite (14x13) offers laminate flooring, walk-in closet, pool views, French doors leading to private balcony and a private study (14x10) perfect for relaxing with a good book. Master bathroom features gorgeous standup shower, waterproof vinyl flooring and lovely tile work. Home features massive family room (39x32) with tile flooring and separate living room (20x13) with wood-exposed cathedral ceilings and gas fireplace. Upstairs you'll find two bedrooms with a shared bathroom in addition to the master bedroom retreat. Laundry room, half bath and fourth bedroom are located on first floor. Upgrades include extending trusses and roof line to add carport, gutters, entire paver driveway, automatic wrought iron gate, sprinklers in front yard, gazebo with power, and a wrought iron fence. Two single car detached garages (20x10) plus additional workshop (20x10) with power, water and exhaust fan, two covered sheds and additional storage space (10x10) located below playhouse/gym provide ample storage to go along with oversized attached carport (33x14). No HOA.

230 E Panama Road, Winter Springs

$825,000

4 Beds ⋅ 4 Baths ⋅ Glen Eagle Unit 2 SubDv. ⋅ 32708 Zip Code

Welcome to this beautifully updated Florida executive pool home in sought-after Glen Eagle community of Winter Springs. On a spacious lot with a private fenced backyard, this exceptional residence blends timeless architecture with modern luxury, thoughtful renovations and the ideal Florida indoor-outdoor lifestyle. From the moment you enter through the welcoming foyer with a stunning crystal chandelier, you will appreciate the attention to detail throughout. The flexible floor plan features a front office (or optional formal living space), elegant formal dining room with designer lighting, a spacious family room with a stone fireplace, and seamless views of the outdoor living area through expansive disappearing sliding glass doors. The completely remodeled kitchen is the heart of the home and showcases custom cabinetry with abundant storage, glass display cabinets, white shaker cabinets with designer hardware, quartz countertops with a sophisticated marble swirl finish, stainless steel hood with glass accents, walk-in pantry, custom lighting, and high-end Cafe by GE appliances (2023) including a built-in style refrigerator and professional-inspired finishes. The adjoining breakfast nook features a custom built-in bench creating the ideal casual dining space. The split-bedroom floor plan offers privacy with three spacious guest bedrooms and two full baths on one side of the home, including a pool bath with direct access to the outdoor living area. A pocket door provides additional separation between the guest wing and main living spaces. The primary suite is privately at the rear of the home and features double doors opening to the pool area, two walk-in closets, dual vanities, spa soaking tub, separate shower, linen storage and a beautifully updated bath. Additional interior highlights include remodeled laundry room with new cabinetry, quartz counters, and LG front-loading washer and dryer, remodeled primary bath and powder room (2017), remodeled guest bath (2025) with designer finishes including gray slate tile and black accents, hardwood flooring throughout bedrooms and halls, tile flooring throughout main living areas, crown molding in main living spaces, ceiling fans throughout, plantation-style white wood blinds throughout, built-in office cabinetry and custom desk/bookcases. The outdoor living experience is exceptional. The tiled front entry and expansive screened lanai were designed to flow seamlessly with the interior living space, creating the ultimate Florida outdoor room. Enjoy the recently resurfaced pool deck, sparkling chlorine pool, garden areas, potting station, swing area, wildflower garden and a private fenced backyard with secure lockable gates. Major improvements provide peace of mind including new roof (2026), high-end Lennox HVAC system (2024), updated kitchen, laundry room and living areas. Easy generator hookup capability with portable generator connection is included. The oversized three-car garage includes additional storage and a refrigerator, while the large driveway provides ample guest parking. In the established Glen Eagle community of Winter Springs, this home offers mature landscaping, spacious lots and convenient access to shopping, dining, top-rated Seminole County schools, parks and major roadways. A rare opportunity to own a beautifully renovated Florida pool home where luxury, comfort and functionality come together.

1669 Eagle Nest Circle, Winter Springs

$820,000

4 Beds ⋅ 2 Baths ⋅ North Orlando Ranches Sec 04 SubDv. ⋅ 32708 Zip Code

Located on 2 acres with R-1AA zoning, this property offers space, flexibility, and privacy while still being conveniently close to everyday essentials. Ideal for those looking to keep horses, store equipment, or run a home-based business. The home features a bright, open layout with high ceilings, abundant natural light, and updated windows with plantation shutters. The remodeled kitchen includes updated cabinetry, granite countertops, stainless steel appliances, a wine fridge, and a large island with breakfast bar. The split floor plan offers a spacious primary suite with a custom walk-in closet and an updated bathroom with dual sinks and a walk-in shower, while three additional bedrooms feature new carpet, updated fixtures, and ample closet space. The secondary bathroom also provides direct access to the pool. Outdoor living is a highlight, with a covered and screened patio overlooking a heated saltwater pool, an extended paver deck, and a gazebo with a firepit area, perfect for entertaining. Recent updates include a roof (2020), AC (2019), and water heater (2025), along with a whole-home water treatment system. The property also features a detached 3-car garage/workshop with AC and potential for a guest house or in-law suite, a shed with AC and water ideal for an office or studio, and a metal pole barn for boat or RV storage. Dual EV charging stations are also installed. This property offers a unique combination of comfort, functionality, and zoning flexibility to fit a variety of lifestyles.

330 Hayes Road, Winter Springs

$799,900

4 Beds ⋅ 3 Baths ⋅ Seville Chase SubDv. ⋅ 32708 Zip Code

SELLER MOTIVATED!! Make OFFER! Freshly Painted Exterior and Interior! Walk in and feel instantly at home! This beautifully renovated 4-bedroom, 3-bathroom triple-split pool home sits on nearly half an acre in the gated community of Seville Chase and is completely move-in ready. Step inside to soaring ceilings and a thoughtfully designed open layout that still offers comfortable separation of space. You’ll immediately notice the stunning porcelain tile floors and a high-end, fully updated kitchen featuring custom cabinetry, pull-out shelving, soft-close drawers and doors, and sleek quartz countertops—perfect for both everyday living and entertaining. Recent upgrades provide peace of mind, including: New tile roof (2025) with a 50-year warranty AC replaced in 2022 Water softener (2022) New pool pump Out back, enjoy your own private retreat with a screened pool overlooking a serene conservation area with a lake—ideal for relaxing or even bass fishing. The expansive yard also features mature fruit trees, including avocado, mango, lemon, and a cherry bush. All of this is conveniently located near Winter Springs, major highways (417 & 434), UCF, Seminole State College, and major employers like Lockheed Martin and Siemens. This home truly has it all—style, space, and location. Schedule your private showing today before it’s gone!

510 Sonata Court, Winter Springs

Single Family Homes for Sale in Winter Springs, FL

Be the First to Know About New Winter Springs Homes

Winter Springs Real Estate Map Search

All Single Family Homes for Sale in Winter Springs, FL

Zen Home Group

Search

Resources

About