Winter Springs Single Family Homes For Sale - 136 homes

Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 724 Lakeside Dr, nestled in the highly sought-after Wildwood community. This beautifully maintained 2-bedroom, 2-bathroom home offers 1,168 square feet of comfortable living space and presents an excellent opportunity for first-time homebuyers, downsizers, or anyone seeking a move-in-ready home in one of Winter Springs' most established neighborhoods. As you step inside, you'll immediately notice the fresh updates throughout, including brand-new carpet that adds warmth and comfort to every room. The functional floor plan offers a spacious living and dining area filled with natural light, creating an inviting atmosphere for both everyday living and entertaining guests. The kitchen provides ample cabinet and countertop space with easy access to the main living areas, making meal preparation and gatherings effortless. The primary suite offers a private retreat complete with an en-suite bathroom and generous closet space. A well-sized secondary bedroom and full guest bathroom provide flexibility for family members, guests, or a home office setup. The guest bathroom has been enhanced with a newly installed backsplash, adding a stylish and modern touch. Step outside and enjoy all that the Wildwood community has to offer. Residents have access to a community swimming pool, tennis courts, playground, and a community clubhouse, providing plenty of opportunities for recreation and social gatherings. The neighborhood's mature landscaping, tree-lined streets, and established character create a welcoming environment that homeowners have enjoyed for years. Conveniently located in the heart of Winter Springs, this home is just minutes from the Cross Seminole Trail, Central Winds Park, Winter Springs Town Center, shopping, dining, and top-rated Seminole County schools. Easy access to major roadways makes commuting throughout Central Florida a breeze while still allowing you to enjoy the charm and tranquility of this sought-after community. Whether you're searching for your first home, looking to downsize, or seeking a low-maintenance lifestyle in a prime location, this property offers the perfect combination of comfort, convenience, and community. Schedule your private showing today and discover everything 724 Lakeside Dr has to offer.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Eric Campbell (321-279-8941)

Remarks: Welcome home! Fall in love this welcoming two-story home that features 4 bedrooms and 3.5 bathrooms, perfectly positioned across from the Cross Seminole Trail. Start your day with a cup of coffee on the charming covered front porch, where you can take in the refreshing breeze and picturesque views of the 13-mile trail that winds through Seminole County and connects to other scenic trails. Step inside to discover an inviting open floor plan enhanced by beautiful wood-style tile flooring. Prepare your favorite meals in the gourmet kitchen with stainless steel appliances, pantry, modern fixtures, and breakfast bar ideal for casual dining. The open-concept living and dining areas create the perfect setting for effortless entertaining. The primary suite, conveniently located on the first floor, includes a walk-in closet and a private ensuite bathroom with dual sinks and a walk-in shower. Ascend to versatile loft area upstairs offering additional space for work, play, or relaxation. You will also appreciate the secondary primary suite on this level, complete with a walk-in closet, dual sinks, and shower. Additionally, two generously sized bedrooms await your use along with a full bathroom. Outside, unwind on the covered back patio, surrounded by vinyl fencing for added privacy. A rear-facing two-car garage with a paver driveway completes the property. This home is part of the Tuskawilla Crossing community, which includes a dog park, a sparkling community pool for leisurely fun, and a playground. The area is rich in dining and shopping options and provides easy access to the 417. Situated in Seminole County which is well known for its public school system. Don’t miss the chance to make this exceptional home yours—schedule a showing today!

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: Brent Dehoop (407-448-8971)

Remarks: Welcome to 143 Hayes Rd, Winter Springs a rare opportunity to own a beautifully renovated home in one of the area’s most exclusive and sought-after locations. Situated on a huge corner lot surrounded by mature trees, this property offers privacy, space, and the freedom of no HOA with low property taxes. This home has been recently updated and is truly move-in ready, featuring a 2017 roof, brand-new AC system, fresh interior and exterior paint, new carpet, and a newly finished driveway. Every detail has been thoughtfully refreshed to provide comfort and peace of mind for the next owner. Step outside and imagine yourself enjoying your own private pool while being surrounded by peaceful natural scenery — the perfect setting for relaxing weekends, entertaining guests, or simply enjoying Florida living at its best. Conveniently located near top-rated schools, shopping, dining, and major highways while still offering the tranquility of a private retreat. Homes like this in Winter Springs rarely hit the market!

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Karla De La Cruz (407-775-0268)

Remarks: Under contract-accepting backup offers. Exceptional investment opportunity in the highly sought-after Highlands community of Winter Springs! This rare and one-of-a-kind duplex features two spacious 3-bedroom, 2-bath units, each offering a 2-car garage, fenced backyard, soaring high ceilings, and thoughtfully designed floor plans that create an open and inviting feel. Both sides are professionally leased, currently generating a combined $3,200/month in gross rental income, with tenants responsible for their own utilities — and there is strong potential to increase rents in today’s market, making this an even stronger long-term investment opportunity. Recent updates provide peace of mind for years to come, including a new roof (2021), fresh exterior paint (2021), HVAC systems replaced on both sides (2021), updated windows, replumbing, updated tile flooring, and freshly painted interiors (2024). Both bathrooms have been professionally re-glazed to look like new while adding long-term durability and extended life to the surfaces. This duplex is extremely hard to find and offers endless possibilities for both investors and owner-occupants alike. It is an ideal income-producing property or perfect opportunity for a first-time homebuyer utilizing FHA financing — allowing the owner to live in one unit while renting out the other side to help offset the mortgage payment. Located in The Highlands, one of Winter Springs’ most desirable communities, residents enjoy scenic walking trails, a waterfront playground, sparkling community pool, clubhouse, and a low HOA — all within an amazing neighborhood known for its lifestyle and convenience. Whether you’re expanding your portfolio, house hacking, or searching for a flexible multigenerational opportunity, this property truly stands out from the rest.

Listing is courtesy of: EXP REALTY LLC (407-641-2808)

Listing Agent: Jeffrey Osborn, Jr (407-221-7134)

Remarks: Welcome to the desirable city of Winter Springs, where 114 Stone Gable Cir sits on a beautiful corner lot with peaceful pond views to the rear and side of the home. Just minutes from shopping, restaurants, theme parks, major roads, and the airport, this move-in ready residence puts convenience right at your fingertips. Inside, 1,814 square feet of bright living space welcomes you with high ceilings and an open floor plan that flows naturally from room to room. Hard flooring runs throughout, keeping upkeep easy while adding a clean, modern look. The kitchen is ready for everything from casual breakfasts to weekend gatherings, featuring sleek granite countertops and stainless steel appliances. This thoughtfully designed home offers three comfortable bedrooms and two full bathrooms. The smart split layout tucks the primary bedroom away on its own side for added privacy, creating a quiet retreat at the end of the day, while two additional bedrooms provide flexible space for family, guests, or a home office. The real showstopper waits out back. Step onto the screened-in porch and enjoy your own private pool, perfect for cooling off under the Florida sun or relaxing as you take in the serene water views. The corner-lot setting adds extra elbow room and a sense of openness rarely found. With its prime location, modern finishes, and resort-style outdoor living, this Winter Springs gem checks every box. Schedule your private showing today and make it yours before it's gone!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Kathy Williams (407-230-7305)

Remarks: Welcome home to this move-in-ready 4-bedroom, 2-bathroom pool home with a 2-car garage, situated on a quiet cul-de-sac with no through traffic. This solid-block-construction home offers an open floor plan and exceptional curb appeal, featuring fresh exterior paint, updated stucco, professional landscaping, and a brand-new roof installed in June 2026. Inside, you'll find fresh interior paint, updated lighting and ceiling fans throughout, and a beautifully renovated kitchen and bathrooms. The spacious kitchen opens to the main living areas and features new stainless steel appliances, making it ideal for both everyday living and entertaining. The living room is anchored by a stunning fireplace that has been transformed with a custom stucco finish, elegant marble accents, and a floating mantel. Major mechanical updates include a 2022 AC system, a brand-new 2026 water heater, and updated plumbing with the home fully repiped, providing added value and peace of mind for years to come. Step outside to enjoy your private screened pool area and fully fenced backyard with no rear neighbors, offering exceptional privacy and the perfect space for relaxation, pets, and outdoor gatherings. With block construction, a brand-new roof, and a location outside of a flood zone, this home offers the potential for lower insurance costs and added peace of mind. For additional buyer confidence, a 4-Point Inspection, Wind Mitigation Report, Wood Destroying Organism (WDO) Report, and Energy Report are attached to the MLS for review. Conveniently located with a low HOA of just $345 per year, this home combines style, comfort, and value in one complete package.

Listing is courtesy of: NEXTDWELL (855-432-1123)

Listing Agent: Austin Cummings (407-242-8891)

Remarks: HUGE PRICE REDUCTION! LOWEST PRICED HOME IN SUNRISE VILLAGE! 2/2 UPDATED HOME! PLUS A BONUS ROOM PERFECT FOR OFFICE, NURSERY, PLAYROOM, HOBBY ROOM, FLORIDA ROOM OR JUST ADDITIONAL LIVING SPACE! OPEN FLOOR PLAN! KITCHEN FEATURES TILE FLOORS, EAT IN KITCHEN AND LIGHT WOOD CABINETRY! ROOF 2022, A/C 2023, WATER HEATER 2025! MAIN BATH UPDATED WITH DECORATIVE TILE, GRANITE COUNTER, TILE FLOOR! DOUBLE PANED WINDOWS! WIDE BLINDS! KNOCKDOWN CEILINGS! NO CARPETING THRU OUT! LARGE SCREENED PATIO WITH TILE FLOOR! LOTS OF NATURAL LIGHT! FANS! LAUNDRY IN GARAGE! GREAT LOCATION, HIGHLY RATED SCHOOLS, LOW HOA DUES ($345 YEAR), COMMUNITY BASKETBALL, TENNIS AND PLAYGROUND!. CONVENIENT TO ALL AREAS OF TOWN! PLEASE NOTE: SOLAR PANELS ON ROOF ARE LEASED, AND LEASE IS TRANSFERABLE! APPROX $80 MONTH! SELLER NOTES WITH POWER COMPANY CREDITS, BILL HAS BEEN APPROX. $30 MONTH!

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Diane Fuller (407-923-2090)

Remarks: Professional Photos Coming Soon! New Roof Being Installed June 17, 2026! A home this loved is hard to find. Lovingly maintained and thoughtfully improved over the years, this traditional 4-bedroom, 3-bath heated saltwater pool home in the desirable Willow Run community of Winter Springs showcases true pride of ownership throughout. The desirable three-way split floor plan offers exceptional privacy and flexibility for families, guests, multi-generational living, or a home office setup. Surrounded by lush, mature landscaping cultivated with care, this Seminole County pool home blends timeless character with thoughtful updates designed for comfortable everyday living and effortless entertaining. Freshly painted throughout, the interior offers a bright, clean backdrop ready for your personal style. Newer windows fill the home with natural light, while solid wood bedroom doors add warmth and quality craftsmanship throughout. The spacious family room is anchored by a classic wood-burning fireplace, creating an inviting gathering space for family and friends. Major updates provide valuable peace of mind, including a newer HVAC system (2020) with Blue Light air purification and service contract, Water Heater (2026), and a brand-new roof being installed June 17, 2026. Florida outdoor living takes center stage with a heated saltwater pool, safety fence, expansive stone-finished pool deck, oversized rear porch, widened driveway, charming front porch, and decorative wrought iron fencing. Whether hosting gatherings, tending the garden, relaxing poolside, or enjoying year-round outdoor living, this property offers the lifestyle many Central Florida buyers are seeking. Located in the heart of Winter Springs, this home offers exceptional convenience with quick access to SR-417, making commuting throughout Central Florida a breeze. Residents enjoy proximity to Winter Springs Town Center, Tuscawilla Country Club, Central Winds Park, the Cross Seminole Trail, shopping, dining, and highly regarded Seminole County schools. Winter Park is approximately 20 minutes away, while Orlando's major theme parks and Florida's east coast beaches can be reached in about 55 minutes, providing easy access to some of the region's most popular destinations. If you're searching for a meticulously maintained pool home in Winter Springs with major updates already completed, exceptional outdoor living spaces, and a location that combines convenience with community, this Willow Run gem deserves your attention. Schedule your private showing today.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Laura Leigh Wood (407-310-4908)

Remarks: Beautiful fully renovated property featuring 4 spacious bedrooms, 2 modern bathrooms, and an additional room perfect for an office or play room. The home has been completely updated, including a new roof and new windows, providing improved energy efficiency and peace of mind. Open layout with excellent natural light and modern finishes throughout. Move-in ready, ideal for a family home or investment opportunity. Conveniently located with easy access to schools, shopping, and major roads.

Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)

Listing Agent: Rodrigo Chavez (407-652-8430)

Remarks: Welcome to this beautifully maintained 4-bedroom, 2.5-bath home nestled on a quiet cul-de-sac in the highly desirable gated community of Parkstone. From the moment you arrive, you'll appreciate the inviting curb appeal, fresh exterior paint, and the pride of ownership throughout. Step inside to discover a light and bright interior filled with airy, spacious living areas designed for both everyday comfort and effortless entertaining. Gorgeous luxury vinyl plank flooring flows throughout the main living spaces, while brand-new carpet adds warmth and comfort to the upstairs bedrooms. Entertaining is a breeze in the large dining room with easy access to the kitchen and family room. The heart of the home opens seamlessly to your private backyard retreat, featuring a sparkling saltwater pool, new sod, and a fully fenced yard that offers both privacy and space to relax, play, or entertain. Whether enjoying a morning coffee poolside or hosting weekend gatherings, this outdoor space is sure to impress. Soaring ceilings on the first floor add to the spacious feeling throughout. Step into the pristine primary suite located on the first floor as an added bonus! Primary bath with separate soaking tub, glass enclosed shower and dual sink vanity make this an owner's dream. Major updates provide peace of mind, including ROOF 2019, AC 2024, FRESHLY PAINTED INTERIOR 2021, HOT WATER HEATER 2021,transferable TERMITE BOND, NEW CARPETS in all bedrooms, NEWLY PAINTED POOL DECK and Taexx, an inovative built-in "tubes in the wall" pest control system .....what more could you ask for? One of the many perks of living in Parkstone is that the HOA takes care of lawn maintenance, giving you more time to enjoy the community and everything the area has to offer. Located just minutes from the popular Central Winds Park, you'll have easy access to festivals, sporting events, walking trails, and community activities year-round. You'll also love being close to Winter Springs Town Center, where shopping, dining, and everyday conveniences are just around the corner. This welcoming home offers the perfect blend of comfort, convenience, and lifestyle in one of Winter Springs' most sought-after gated communities.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Colleen Kahl (407-630-0027)

Remarks: Explore 448 MacGregor Rd, a individual residence with a straightforward design and integrated features. The interior includes a fireplace, and the primary bedroom features a walk in closet; the primary bathroom provides double sinks and a Jacuzzi. The exterior includes a covered patio and a fenced in backyard, providing an enclosed outdoor area. This property contains practical elements for daily living. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Under contract-accepting backup offers. Experience the ultimate Florida lifestyle at this stunning 4-bedroom (plus home office) or 5-bedroom, 3.5-bathroom retreat nestled in the exclusive gated community of Parkstone. Come home to soaring, high ceilings and a bright, open floorplan that’s an entertainers dream. The Chef’s kitchen features stainless steel appliances, and a breakfast bar as well as a window enjoying views of the screen patio and beautiful backyard. You will love the oversized primary suite that features stunning conservation views, and connects to a private, flexible room perfect for an office or nursery, or even a fifth bedroom. One of the additional bedrooms has an on suite bathroom and walk in closet as well. Wake up to breathtaking sunrises and spend your evenings watching wildlife. This exceptional property features a private 300ft boardwalk that winds through Florida Hammock vegetation and leads to your own personal boathouse. This incredible, covered boat dock features both electric and water access, plus a boat lift for effortless access to the scenic, expansive Lake Jesup. Enjoy relaxing on the screened lanai or the open paver patio while enjoying the sounds of nature. NEW ROOF IN 2024 (House and Boat Dock), NEW PORCH ROOF 2025, NEW WATER HEATER 2025, NEW A/C 2021, FRESHLEY PAINTED 2021, RAIN GUTTERS 2020. Relish your time at the private community fishing pier, tennis court, take a dip in the gorgeous community pool or enjoy the splash pad. Lawn Maintenance is even included in your HOA (Lawncare includes mowing of lawn, trimming of bushes and fertilizer). Parkstone is a gated community with walking trails, scenic ponds, tennis court, community dock, two playgrounds, a splash pad and community pool to enjoy. The Cross Seminole Trail borders Parkstone and you are just a short walk from Central Winds Park, the Dog park and the Newly opened Pickleball Facility! Minutes from grocery stores, The Town Center, shopping and dining, this home has it all! Welcome home!

Listing is courtesy of: SHORESTONE PROPERTY GROUP (407-452-9818)

Listing Agent: Tania Crandall (407-452-9818)

Remarks: Beautiful 3-bedroom, 2-bath pool/spa home located in the highly desirable Sunrise Estates in Winter Springs, featuring a split floor plan on nearly ¼ acre with no front neighbors for added privacy. This home boasts a newer roof and newer pool/spa heater, making it perfect for entertaining family and friends, while the oversized backyard and large covered screened-in patio provide an ideal outdoor living space. Inside, enjoy a wood-burning fireplace for warmth and ambiance on cooler evenings, along with no carpet throughout for easy maintenance. Sunrise Estates offers open parks, tennis courts, basketball courts, and softball fields, and is zoned for A-rated Seminole County schools, making it perfect for a growing family. Conveniently located near major highways, dining, shopping, and just minutes from Oviedo and Winter Park—schedule your private tour today!

Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)

Listing Agent: Antonio Salinger (407-304-9867)

Remarks: Nestled on nearly two private acres in coveted Old Tuskawilla, this one-of-a-kind custom estate offers a rare opportunity to enjoy space, privacy, and timeless character in one of Seminole County's most sought-after communities. Surrounded by majestic oak trees, the property feels like a private retreat while remaining just minutes from top-rated schools, parks, golf, dining, and shopping. A private driveway leads to the home's side-entry two-car garage and picturesque setting. Inside, 2,191 square feet of living space blends warmth and functionality. Solid cherry hardwood flooring flows throughout the main level, where you'll find the formal dining room, a spacious family room, two fireplaces, a breakfast nook, and a generously sized primary suite conveniently located on the first floor. Also on the main level is a flexible office space that could easily serve as a fourth bedroom with minimal modifications, offering added versatility for growing families or guests. Upstairs, two bedrooms feature large closets and share a renovated Jack-and-Jill bathroom. The second floor has been updated with luxury vinyl plank flooring. The screened porch provides the perfect place to enjoy morning coffee while overlooking the expansive backyard, offering endless possibilities for a custom pool, guest house, workshop, or simply enjoying the natural beauty of the property. Nature lovers will appreciate the trail located directly behind the property, providing access for walking, jogging, and exploring the outdoors. Major updates provide peace of mind, including a whole-house repipe (2022), a 10' x 12' storage shed added in 2025, a new roof (2026), and fresh exterior paint (2026). While the kitchen and primary suite present opportunities for cosmetic updates and personalization, the home's solid construction, exceptional lot, and desirable location create an incredible foundation for your vision. Properties with this much land, character, and potential rarely become available in Tuskawilla. Whether you're seeking room to spread out, a private estate setting, or the chance to create your forever home, this exceptional property offers a truly unique opportunity.

Listing is courtesy of: VAN DEN BERG REAL ESTATE GROUP (407-739-9970)

Listing Agent: Caroline Van Den Berg (407-739-9970)

Remarks: Rare opportunity in the heart of Winter Springs! Situated on an expansive 0.72-acre lot with NO HOA, this unique 4-bedroom, 2.5-bath pool home offers endless potential for the buyer seeking space, privacy, and the chance to create something truly special. The property features a recently resurfaced pool, a fully fenced backyard, and an incredible outdoor setting designed for entertaining and enjoying Florida living. One of the standout features is the detached pizza kitchen gazebo, perfect for hosting family and friends, along with an additional outbuilding complete with A/C, power, and plumbing—ideal for a workshop, studio, home office, hobby space, or future guest accommodations. Mature landscaping and abundant outdoor space provide room for recreation, gardening, boats, RVs, and more. Inside, the home offers a functional layout with tremendous upside. While cosmetic updates could enhance the property's full potential, the major features, lot size, and unique amenities make this a rare find in Winter Springs. Whether you're looking for a personal residence, multi-generational living setup, or an investment opportunity, this property is ready for your vision.

Listing is courtesy of: EXIT REALTY PREMIER LEGACY (407-801-8219)

Listing Agent: Chandler Williams (407-702-3815)

Remarks: Welcome to this beautifully maintained and updated 3 bedroom, 2 bath home with a 2-car garage, ideally situated in the highly desirable Tuscawilla community of Winter Springs. Offering a combination of modern updates, timeless character and serene waterfront views, this move in ready home is a rear find. Step inside to discover an inviting floor plan, featuring ceramic tile and laminate flooring throughout, providing both style and easy maintenance. The updated kitchen is designed for everyday living and entertaining, complete with modern cabinetry, stainless steel appliances, granite countertops, with a black side by side refrigerator, skylight that fills the space with natural light and a built-in wine rack for added charm. The spacious family room serves as the heart of the home, highlighted by a striking brick wood burning fireplace and elegant exposed wood beams that adds warmth and architectural character. Sliding glass doors create a seamless connection between the indoor living spaces and the outdoors while framing beautiful views of the pond. Relax and unwind in the screened in porch overlooking the tranquil water, where you can enjoy peaceful mornings, evening sunsets and the beauty of Florida's natural surroundings. The primary suite and additional bedrooms offer comfortable living spaces, with sliding glass door access providing abundant natural light and picturesque views. The home also offers valuable peace of mind with major updates already completed, including a new roof installed in 2022 and a new HVAC system installed in 2021. Located in the sought after Tuscawilla community, residents enjoy convenient access to parks, walking trails, golf, tennis facilities, shopping, dining, and top rated Seminole County schools. Whether you are looking for your forever home or a peaceful retreat, this waterfront gem delivers comfort, convenience and lasting value. Don't miss your opportunity to own this beautifully updated pond-view home in one of Winter Springs' most desirable neighborhood.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Karen Khairullah-Wallace (407-256-3465)

Remarks: Explore 811 Maple Leaf Loop, recently enhanced with fresh interior paint. The kitchen includes a functional island, and the primary bathroom provides double sinks for practical use, a walk in closet and convenience of a separate tub and shower. Beyond the interior, exterior grounds feature a covered patio and a fenced in backyard. Discover modern comfort and practical living in this updated residence. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Welcome to 472 Dewars Court, a beautifully maintained 4-bedroom, 2.5-bath pool home offering over 2,200 square feet of living space in one of Winter Springs' most desirable communities. Tucked away at the end of a quiet cul-de-sac, this exceptional property provides the perfect combination of privacy, comfort, and convenience with a serene wooded backdrop and no rear neighbors. Inside, you'll find a spacious and functional floor plan designed for both everyday living and entertaining. The kitchen features a gas stove for the home chef, while the home's whole-house Generac gas generator provides peace of mind and uninterrupted comfort year-round. Multiple living and dining spaces offer flexibility for growing families, remote work, or hosting guests. Step outside to your private backyard oasis featuring a sparkling pool, expansive patio space, and tranquil wooded views—perfect for relaxing, entertaining, or enjoying Florida's beautiful weather. Located within The Highlands, one of Winter Springs' most sought-after communities, residents enjoy access to incredible amenities including a large Olympic-sized community pool, scenic nature trails, multiple parks, playgrounds, and recreation areas surrounded by mature oak trees that create a picturesque neighborhood setting. The Highlands is known for its strong sense of community, low traffic streets, and family-friendly atmosphere. Winter Springs consistently ranks among the most desirable places to live in Seminole County thanks to its highly rated schools, beautiful parks, excellent shopping and dining options, and convenient access to Lake Mary, Oviedo, Winter Park, Downtown Orlando, and major highways. This is a rare opportunity to own a private pool home on a cul-de-sac lot with wooded views in one of Central Florida's most established and sought-after communities. Schedule your private showing today.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: David Coker (407-923-8290)

Remarks: 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.

Listing is courtesy of: THE AGENCY FL (407-335-4119)

Listing Agent: Brian Hyser (407-951-2472)

Remarks: Under contract-accepting backup offers. Nestled beneath a canopy of mature trees in a charming ranch-style setting in Winter Springs, this custom-built 2016 Craftsman blends timeless architecture with today’s most sought-after design features. From the expansive front porch to the bright open-concept floor plan, every detail was designed for modern living and effortless entertaining. The chef-inspired kitchen serves as the heart of the home with quartz countertops, an oversized 9-foot center island, soft-close wood cabinetry, stainless steel appliances, and a massive walk-in pantry ideal for storage and organization. A dramatic 4-panel sliding glass door opens to the spacious wood deck and fully fenced backyard, creating seamless indoor-outdoor living perfect for gatherings, relaxing evenings, and Florida entertaining. The first-floor primary suite is a private retreat featuring a spa-style bath with a clawfoot soaking tub, oversized rain-head shower, dual vanities, and an expansive walk-in closet. Additional highlights include spacious secondary bedrooms, flexible loft space, abundant natural light, and quality craftsmanship throughout. Conveniently located near major highways, top-rated schools, shopping, dining, hospitals, and everyday conveniences, this exceptional Winter Springs home offers the ideal balance of peaceful surroundings and central Florida accessibility

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Victoria Myers (407-401-3249)