Location: Winter Springs
Do Not Show Listings
448 MACGREGOR RD, WINTER SPRINGS, FL 32708
$350,00071 Days on yellowkey MLS ID: O6397231
0 Days Off yellowkey (back on 6/17/2026)
REDUCED by $10,000 (2.8%) on 05/27/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1477 Built: 1993Monthly Fee: $6 Tax: $1,141 (2024)Community: Highland Village 2Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,141
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
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)
1233 STONE HARBOUR RD, WINTER SPRINGS, FL 32708
$729,900114 Days on yellowkey MLS ID: O6384753
0 Days Off yellowkey (back on 4/2/2026)
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2908 Built: 2003Monthly Fee: $150 Tax: $2,062 (2025)Community: Parkstone Unit 3Single Family
Taxes:$2,062
Elementary School: Layer Elementary
High School: Winter Springs High
Tax Year: 2025
Middle School: Indian Trails Middle
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)
1024 DINERO DR, WINTER SPRINGS, FL 32708
$419,00048 Days on yellowkey MLS ID: O6404240
REDUCED by $5,000 (1.2%) on 06/17/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1463 Built: 1986Monthly Fee: $29 Tax: $4,882 (2024)Community: Sunrise Estates Unit 2Spa: YesSingle Family
Taxes:$4,882
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)
975 DYSON DR, WINTER SPRINGS, FL 32708
$879,0001 Day on yellowkey MLS ID: O6417467
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2191 Built: 1980 Tax: $6,089 (2025)Community: Winter Spgs Unit 3Single Family
Taxes:$6,089
Elementary School: Rainbow Elementary
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)
1204 SWAN ST, WINTER SPRINGS, FL 32708
$624,0001 Day on yellowkey MLS ID: O6417440
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3334 Built: 1973 Tax: $3,677 (2024)Community: Winter Spgs Unit 4Spa: YesSingle Family
Taxes:$3,677
Elementary School: Keeth Elementary
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)
1441 FOREST HILLS DR, WINTER SPRINGS, FL 32708
$420,0002 Days on yellowkey MLS ID: O6413957
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1731 Built: 1985Monthly Fee: $90 Tax: $2,546 (2025)Community: Wedgewood Tennis VillasSingle Family
Taxes:$2,546
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)
811 MAPLE LEAF LOOP, WINTER SPRINGS, FL 32708
$545,00014 Days on yellowkey MLS ID: O6413927
0 Days Off yellowkey (back on 6/16/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2852 Built: 2016Monthly Fee: $100 Tax: $4,089 (2025)Community: Seven OaksSpa: NoSingle Family
Taxes:$4,089
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
1406 BLUMBERG BLVD, WINTER SPRINGS, FL 32708
$425,00031 Days on yellowkey MLS ID: O6408695
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1476 Built: 2024Monthly Fee: $356 Tax: $6,076 (2025)Community: Hickory Grove TwnhmsTownhouse
Taxes:$6,076
Remarks: Welcome to this almost-new townhome in beautiful Winter Springs! Located in the desirable Hickory Grove community, where you will find a maintenance free living, relaxing pool and cabana, playground for the little ones and a dog park for your furry friend, all just a few steps away and NO CDD to pay. The monthly HOA dues also include: landscaping, irrigation, weed control, exterior paint, roof, 1GB of high speed internet and cable premium package. This stunning residence has been tastefully decorated and offers the perfect blend of modern style, comfort, and convenience. Your front door opens up to the serene parks, fountains and walkways just across the street from your favorite stores and restaurants. Enjoy an open-concept layout with plenty of natural light, a modern kitchen with state of the art SS appliances, quartz counters and a beautiful island to entertain your guests. 3 bedrooms, 2.5 bathrooms, and a 2-car garage, and much more. This home is move-in ready and designed for easy living. Upstairs, the generous primary suite offers a private retreat with an en-suite bath and ample closet space. Built with today’s lifestyle in mind, this home also includes the peace of mind of a builder warranty, this is a fantastic opportunity to own a like-new home in one of Central Florida’s most sought-after areas with top-rated schools.
Listing is courtesy of: RALISTO, LLC (407-493-6032)
Listing Agent: Kalex Espinosa (407-493-6032)
472 DEWARS CT, WINTER SPRINGS, FL 32708
$499,90014 Days on yellowkey MLS ID: O6413206
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2222 Built: 1995Monthly Fee: $13 Tax: $2,066 (2025)Community: Highland Lake Ph 2Single Family
Taxes:$2,066
Elementary School: Highlands Elementary
Middle School: South Seminole Middle
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)
600 NORTHERN WAY #906, WINTER SPRINGS, FL 32708
$290,000140 Days on yellowkey MLS ID: O6375918
REDUCED by $20,000 (6.5%) on 06/01/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1609 Built: 2016 Tax: $4,259 (2024)Community: Tuscany Place Ph 1Condo
Taxes:$4,259
Remarks: Turnkey townhouse in Tuscany Place is totally move-in ready. The townhouse style is limited to only a few homes in the new phase of this wonderful, gated community. Built in 2016 and much newer than many competing condos/townhomes. All 3 bedrooms have their own private full bathrooms. The first-floor bedroom with en-suite bath is great for guests, home office, or multigenerational living. Brand new roof (2026). Newer HVAC (2020). Low maintenance townhouse-style living. Spacious open-concept kitchen and overall excellent layout. This home's natural focal point is the kitchen with granite countertops, and there's an extra-large kitchen island, which provides essential counter space and storage, cabinets and drawers, and room for a breakfast bar. The kitchen leads to the rest of the living and family room combination, which features glass sliding doors to the patio and a staircase to a great split plan layout for the bedrooms upstairs. This home has all the features you’re looking for including a laundry room with large-size appliances, walk-in closets, a huge refrigerator, dedicated trash drawer in the kitchen, blinds and window treatments, and modern fixtures throughout the home. See yourself living in the heart of beautiful Winter Springs. Low monthly fee covers access to the community pool, exterior maintenance and landscaping, sewer, and trash services. Very close to all the shopping and restaurants at Winter Springs Town Center, and Trotwood Park is right at your doorstep. Contact us today to schedule a private tour!
Listing is courtesy of: JR REALTY GROUP LLC (407-920-4624)
Listing Agent: John Vincent (407-534-9764)
1112 ORANGE AVE, WINTER SPRINGS, FL 32708
$3,998,000434 Days on yellowkey MLS ID: O6298615
Bed: 5 Bath: 6.5 Gar: 6 Liv Area Sq Ft: 8685 Built: 2008 Tax: $14,976 (2024)Community: Lake JessupSpa: YesSingle Family
Taxes:$14,976
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)
613 BONITA RD, WINTER SPRINGS, FL 32708
$719,00073 Days on yellowkey MLS ID: O6395444
REDUCED by $20,000 (2.7%) on 06/03/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3281 Built: 2016 Tax: $8,389 (2025)Community: North Orlando Ranches Sec 02ASingle Family
Taxes:$8,389
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)
440 BUCKSKIN CT, WINTER SPRINGS, FL 32708
$534,90083 Days on yellowkey MLS ID: O6394274
REDUCED by $14,100 (2.6%) on 05/22/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1922 Built: 1986Monthly Fee: $30 Tax: $5,731 (2025)Community: Deer Run Unit 20Single Family
Taxes:$5,731
Elementary School: Red Bug Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** PAID-OFF 15kW SOLAR + 10Gb whole-home Ethernet — corner lot in the heart of Winter Springs! This 4BR/2.5BA Deer Run home blends colonial charm and fresh curb appeal with smart upgrades new construction can't touch. Whole-home fiber terminal & wired Ethernet in every room. Smart thermostat w/ 3 remote sensors (app-enabled). New master shower & custom closet w/ multiple bars & abundant shelving. Re-piped 6-zone irrigation w/ modular manifold & smart rain/soil-aware controller. Hardwired smoke detectors, GFIs in all wet areas & shower vent fans throughout. Open floor plan, engineered hardwood & wood-burning fireplace. Outside, enjoy fresh landscaping, a brand-new fence & a corner lot your neighbors will envy — all minutes from the 417, Red Bug Lake Rd, Tuskawilla Rd, top-rated Seminole County schools, parks & shopping. Updated the right way — come see it today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
1201 WOLVERINE TRL, WINTER SPRINGS, FL 32708
$500,000151 Days on yellowkey MLS ID: O6374676
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1979 Built: 1977 Tax: $5,709 (2024)Community: Winter Spgs Unit 4Single Family
Taxes:$5,709
Remarks: Welcome to this charming 4-bedroom, 2-bath home tucked away in a quiet, tree-lined neighborhood in desirable Winter Springs. Surrounded by mature trees, this property offers a peaceful atmosphere and a spacious backyard, ideal for entertaining, relaxing, or enjoying Florida outdoor living. Inside, you’ll find a warm and inviting layout highlighted by an original masonry fireplace, adding timeless character and charm. Skylights in the living room and hallway flood the home with natural light, creating a bright and airy feel throughout the main living spaces. Conveniently located near schools, parks, shopping, dining, and major roadways, this home offers the perfect blend of tranquility and accessibility in an established community.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Nairobi Rondon (786-935-0365)
819 DUNDEE DR, WINTER SPRINGS, FL 32708
$419,00015 Days on yellowkey MLS ID: O6412585
REDUCED by $10,000 (2.3%) on 06/16/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1701 Built: 1978Monthly Fee: $40 Tax: $1,558 (2025)Community: Highlands Sec 1Single Family
Taxes:$1,558
Remarks: Welcome home to this charming 4-bedroom, 2-bath residence nestled on a spacious corner lot in the highly desirable Highlands community of Winter Springs. From the moment you arrive, you'll appreciate the inviting curb appeal, mature surroundings, and move-in ready condition that make this home truly special. Inside, vaulted ceilings and abundant natural light create an open and airy atmosphere, while updated flooring adds a fresh, modern touch throughout. The heart of the home features a cozy wood-burning fireplace, perfect for gathering with family and friends. The kitchen is both stylish and functional, offering beautiful wood cabinetry, granite countertops, and stainless steel appliances. The thoughtfully updated bathrooms provide comfort and convenience, while sliding glass doors from the living room lead to an expansive covered and screened patio—an ideal space for morning coffee, weekend barbecues, or simply relaxing and enjoying Florida's beautiful weather. The partially fenced backyard offers plenty of outdoor space, complete with a storage shed for tools, hobbies, or seasonal items. Located within The Highlands, residents enjoy access to exceptional community amenities including a swimming pool, playground, and tennis courts. Conveniently situated near shopping, dining, parks, and major highways, this home offers the perfect blend of comfort, convenience, and community. Don't miss your opportunity to make this wonderful Winter Springs home your own!
Listing is courtesy of: KGV REALTY GROUP (407-474-0844)
Listing Agent: Kristin Vogt Pllc (407-417-7206)
270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$249,900218 Days on yellowkey MLS ID: O6359666
REDUCED by $9,100 (3.5%) on 06/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1089 Built: 1994Monthly Fee: $121 Tax: $327 (2024)Community: Deersong 2Spa: NoSingle Family
Taxes:$327
Remarks: Price Improvement to $259,000 * Quick Closing Available. Welcome to 270 San Gabriel Street in Winter Springs—now offered at an updated price and ready for its next owner. This well-maintained, single-story home features vaulted ceilings and a bright, open layout that creates a comfortable and inviting living space. With neutral finishes and ceramic tile flooring throughout, the home is truly move-in ready. All appliances are included for added convenience. Enjoy morning coffee or unwind in the evening on the oversized screened patio, offering a private outdoor retreat. Additional exterior storage provides practical space for bikes, tools, and seasonal items. Located just minutes from the scenic Cross Seminole Trail, the Deersong community also offers access to a pool and cabana for residents to enjoy. Nearby parks, shopping, dining, and top-rated Seminole County schools add to the home’s appeal. Considering making a move to downsize? First-time homebuyer? investor? or seeking a low-maintenance second home in Central Florida? Schedule your private showing today. With a newly reduced price and quick closing available, this is an excellent opportunity to own a well-cared-for home in a desirable location..
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Alie Gattis (407-760-1488)
140 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708
$769,90077 Days on yellowkey MLS ID: O6395594
REDUCED by $10,000 (1.3%) on 06/10/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3129 Built: 1999Monthly Fee: $184 Tax: $5,857 (2024)Community: Seville ChaseSingle Family
Taxes:$5,857
Elementary School: Sterling Park Elementary
Remarks: Welcome to a residence that truly embodies the phrase "NEIGHBOR'S ENVY, OWNER'S PRIDE" - an exceptional opportunity to own a showpiece home in the gated enclave of Seville Chase where smart living meets timeless elegance. This impeccably maintained, Solar-Powered SMART home offers an unparalleled blend of luxury, comfort, and sustainability. With Fully Paid Solar Panels keeping monthly electric cost under $45. The property greets you with commanding curb appeal, an extra-wide driveway, and an oversized side-entry garage, setting the tone for what lies within. Step inside to discover a designer-inspired interior adorned with gleaming cherry hardwood floors, elegant French doors, soaring tray ceiling, gracefully rounded architectural walls, and refined crown molding- each detail curated for those with a taste for elevated living. The heart of the home, a chef's kitchen, showcases Granite countertops, luxurious 42" cherry cabinetry with crown molding, a built-in desk, ample storage, and sleek stainless-steel appliances-perfectly blending form and function. A thoughtful 3-way split floor plan ensures privacy and space for all, with the primary suite offering a serene retreat complete with his and her walk-in closet and shared linen cabinetry. The fifth bedroom, with its custom-built-in shelving, is ideally suited for a nursery, personal library, or a quiet study. At the Rear, a True Showstopper awaits - an Expansive 1,000+ sq ft screened and paved lanai, fully outfitted with a complete outdoor kitchen, with ADDITIONALD NEW FULL SIZE REFRIGERATOR, Gas hook-up with Range, Microwave, etc. ready to host unforgettable evenings under the stars. Surrounded by Fresh landscaping, New Sod, and vibrant plantings with a gazebo this home has been lovingly updated with a new roof in 2016, solar in 2021, and two high-efficiency A/C systems (5-ton in 2016 and 3-ton in 2014). Ideally located in the highly acclaimed Seminole County School District, and just minutes from premium shopping and places to worship, this is more than a home, it's a lifestyle. Experience the beauty, serenity, and elegance this exceptional property has to provide. Your home awaits. DO NOT FORGET TO CLICK THE LINK TO SEE THE VIDEO WALK-THROUGH.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES (407-644-5385)
Listing Agent: Joji Jacob (407-747-3681)
809 BIG BUCK CIR, WINTER SPRINGS, FL 32708
$549,0004 Days on yellowkey MLS ID: O6416554
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2250 Built: 1984Monthly Fee: $3 Tax: $6,018 (2025)Community: Oak Forest Unit 3Single Family
Taxes:$6,018
Remarks: Welcome home to this beautifully renovated 4-bedroom, 2-bath residence offering approximately 2,250 square feet of thoughtfully designed living space in the highly desirable Oak Forest subdivision. From the moment you arrive, you'll appreciate the exceptional care and attention to detail that make this home truly move-in ready. The open-concept floor plan creates a bright and inviting atmosphere, perfect for both everyday living and entertaining. Luxury vinyl and tile flooring flow throughout the home, providing style, durability, and easy maintenance with no carpet to worry about. At the heart of the home is a stunning, fully renovated kitchen featuring quartz countertops, soft-close cabinetry, convenient pull-out drawers, and high-quality appliances that will delight any home chef. The spacious living and dining areas seamlessly connect to the Family Room, where vaulted ceilings, abundant windows, and natural light create a warm and welcoming gathering space. A wet bar complete with a bar refrigerator makes entertaining family and friends effortless. The spacious primary suite offers a beautifully updated bathroom with quartz countertops and a luxurious walk-in shower featuring a rainfall shower head. The secondary bedrooms are generously sized, and the guest bathroom has also been tastefully renovated with quality finishes. Step outside to your backyard retreat, thoughtfully designed for relaxation and entertaining while the cozy fire pit creates the perfect setting for enjoying cool Florida evenings. Major updates provide peace of mind for years to come, including a new roof installed in 2026, new soffits and gutters, new windows, a new water heater, complete repiping, and a new electrical breaker panel, AC installed in 2020. The garage floor has been freshly coated, adding to the home's clean and polished appearance. Ideally located near shopping, restaurants, medical facilities, and major roadways including SR 436, SR 434, and SR 417, this home offers exceptional convenience for commuting and daily living. Residents will also appreciate access to highly regarded schools. This meticulously maintained home combines modern upgrades, quality craftsmanship, exceptional outdoor living space, and an unbeatable location—making it a rare opportunity in Oak Forest.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Cheri Brandi (321-303-9456)
568 BUCKHORN DR, WINTER SPRINGS, FL 32708
$485,00010 Days on yellowkey MLS ID: O6413584
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2076 Built: 2012Monthly Fee: $167 Tax: $3,280 (2025)Community: Winter Spgs Village Ph 1Single Family
Taxes:$3,280
Remarks: This is one of the few 4 bedroom Bungalows built in sought after Winter Springs Village and it is situated on a premium lot with a manicured greenspace in front and a pond view with a lighted fountain in the rear. Enjoy sitting on the front porch in this quiet and serene setting with no through traffic. Recently painted interior and trim along with brand new carpet upstairs. This turn key property has lower utility bills due to many energy efficient features & design with Low E Vinyl dual pane double tint windows, foam insulated attic, energy star appliances & AC replaced in 2019. This 4 bedroom floor plan has a spacious loft area & 2.5 bathrooms, separate dining room, living room that is open to the kitchen & a full 2 car garage with extra ceiling racks for additional storage. The HOA includes lawn & irrigation maintenance, community pool/clubhouse, playground & secure mailboxes. In walking distance to the Seminole Trail, Winter Springs Town Center, restaurants & Publix. Easy access to 417 for a commute downtown, University of Central Florida, Orlando International Airport or the beaches. Highly rated Seminole County Schools. Bring your most discriminating buyers as this home will not disappoint!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: P. Darlene Brown, Pa (407-719-4420)
1110 SHADOWBROOK TRL, WINTER SPRINGS, FL 32708
$575,00014 Days on yellowkey MLS ID: O6413323
0 Days Off yellowkey (back on 6/15/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2214 Built: 1998Monthly Fee: $50 Tax: $3,542 (2025)Community: Winding Hollow Unit 4Single Family
Taxes:$3,542
Remarks: Under contract-accepting backup offers. Nestled within the DESIRABLE Winding Hollow community, this residence presents a CHARMING front exterior, highlighted by a meticulously maintained lawn and lush landscaping. An inviting entryway, featuring distinctive double doors, sets a welcoming tone upon arrival. The interior unfolds into an OPEN CONCEPT living, dining, and kitchen area, designed for both comfort and connectivity. The spacious living room offers ample space for various arrangements, and overlooks the lanai & pool. Perfectly positioned adjacent to the living room, the DINING area is bathed in NATURAL LIGHT from the large window enhancing the home's OPEN and airy feel. Culinary endeavors are elevated in the well appointed GORGEOUS kitchen, boasting GRANITE countertops, SS appliances, and abundant wooden cabinet space for storage. The KITCHEN is the heart of the home with a LARGE ISLAND offering a vantage point into the family and dining areas, fostering a sense of togetherness. An additional eat-in kitchen area provides flexibility for casual dining. This home encompasses 4 well-proportioned bedrooms and 3 FULL bathrooms, spanning 2,214 square feet. The PRIMARY suite offers a private retreat, featuring a double vanity, a LUXURIOUS soaking tub, and a separate walk-in shower, creating a spa-like experience. The additional bathrooms are thoughtfully designed with contemporary fixtures and tiled showers, ensuring comfort and style. Practical amenities include a dedicated laundry room, equipped with a stacked washer and dryer and ample storage cabinets, enhancing daily convenience. A 3-car garage provides extensive parking and storage solutions, catering to diverse needs. OUTDOOR LIVING is seamlessly integrated with a screened-in patio, offering a comfortable space to relax and enjoy the surroundings. Beyond the patio, a sparkling POOL invites recreation and leisure, and is the perfect oasis for unwinding. The property's location offers exceptional convenience to a wealth of local amenities. Proximate to the vibrant Winter Springs Town Center, an array of shopping and dining options are readily available. Award-winning CENTRAL WINDS PARK provides expansive green spaces with a DOG PARK and 14 PICKLEBALL COURTS, and the CROSS SEMINOLE TRAIL is right outside the neighborhood. Top Rated Seminole County Schools and easy access to the 417. This home has it ALL. Make YOUR showing appointment today.
Listing Agent: Dawn Tinder (407-733-6846)
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