Location: Winter Springs
Do Not Show Listings
809 BIG BUCK CIR, WINTER SPRINGS, FL 32708
$549,0002 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,018
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
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)
1411 BORG LN, WINTER SPRINGS, FL 32708
$385,000136 Days on yellowkey MLS ID: O6378665
0 Days Off yellowkey (back on 6/15/2026)
REDUCED by $14,000 (3.5%) on 06/10/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1368 Built: 1981Monthly Fee: $90 Tax: $1,871 (2024)Community: Wedgewood Tennis VillasSingle Family
Taxes:$1,871
Elementary School: Keeth Elementary
High School: Winter Springs High
Tax Year: 2024
Middle School: Indian Trails Middle
Remarks: Price Reduced!! Your wait is over! Welcome to your new home! This beautiful 3 bedroom, 2 bath home delivers 1,368 sq. ft. of peaceful living area in a quiet corner lot. Located in the gorgeous Tuskawilla Country Club community, this home features luxury vinyl flooring throughout the house. Entertain effortlessly with a spacious kitchen featuring stainless steel appliances, recessed lighting, and 42” upgraded cabinets. The main floor master bedroom has walk in closet and access to the covered patio. House has been updated with a new roof in 2023, A/C unit in 2018, Water Heater in 2020, luxury vinyl floors and vinyl fencing. Enjoy the Florida outdoors with a covered and screened in porch to entertain and gaze out over the huge fenced in backyard. Winter Springs is an established community know for its A-Rated schools, "Tree lined streets", golf courses, tennis, and with easy access to shopping at Oviedo Marketplace, Trotwood park and the 417. Schedule a showing today and come experience Winter Springs living.
Listing is courtesy of: SOLID OAK REAL ESTATE LLC (321-888-9232)
Listing Agent: Trevor Laug (321-888-9232)
662 SARANAC DR, WINTER SPRINGS, FL 32708
$643,10011 Days on yellowkey MLS ID: O6413437
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2180 Built: 1986Monthly Fee: $6 Tax: $3,686 (2025)Community: Tuscawilla Unit 14ASingle Family
Taxes:$3,686
Remarks: Under contract-accepting backup offers. Welcome to this beautiful 4-bedroom, 2-bath pool home nestled in the highly sought-after Tuscawilla community of Winter Springs. Situated on an oversized .34-acre lot, this well-maintained residence offers more than 2,180 square feet of comfortable living space with a spacious, open floor plan designed for both everyday living and entertaining. Enjoy cozy evenings by the fireplace, relax by the private pool, and appreciate the convenience of a two-car garage. The property is surrounded by mature trees and lush landscaping, creating a peaceful and inviting setting. Ideally located near top-rated Seminole County schools, parks, shopping, dining, and major roadways, this home also offers close proximity to Trotwood Park and Tuscawilla Country Club, with easy access to Oviedo, Winter Park, and downtown Orlando.
Listing is courtesy of: WATSON REALTY CORP (407-332-6000)
Listing Agent: Jim Ruddy (407-718-0984)
314 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$279,990249 Days on yellowkey MLS ID: O6350799
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1091 Built: 1992Monthly Fee: $127 Tax: $2,209 (2024)Community: DeersongSpa: NoSingle Family
Taxes:$2,209
Remarks: **BUYER INCENTIVE AVAILABLE!! Preferred Lender is offering a COMPLIMENTARY TEMPORARY RATE BUY DOWN for qualified buyers on new loan locks completed on or before 6/30/26!!** Seller offering $2,500.00 toward Buyers Closing costs with an acceptable offer. Welcome to your dream home, perfectly positioned for easy commuting in Central Florida. This 3 bedroom, 2 full baths, split bedroom plan and screen enclosed side porch home boasts upgrades that make it shine brighter than most — capturing attention with these enhancements: Water Heater (Installed 03/2026), Roof (installed 2021) replaced in recent years for added peace of mind, insurance savings, and easier loan approval, Air Conditioning (2022) allowing you to stay comfortable year-round with a modern, energy-efficient system,Total Re-piping (2021) ensures smooth water flow and reduces future maintenance needs, Dishwasher (2021) for easy clean up. Stove & Refrigerator (2022) updated appliances for a sleek, functional kitchen, ready for your culinary adventures, Extra Kitchen Cabinets (2022) for extra space for all your kitchen storage needs, Luxury Vinyl in Bedrooms 2 & 3 provide a stylish, durable flooring that’s easy to maintain, Interior Paint (2021) fresh and neutral color walls throughout the home, Water-softener allows you to enjoy softer water for bathing, reduced hard water scale buildup, extended appliance life, and easier cleaning. This home is ideal for efficient daily living. Recent improvements mean less upkeep and more relaxation for you as well as the low HOA fees cover front and right side mowing, maintenance on the fence and shed, and a sparkling community pool — giving you more time to enjoy life! Newer systems and structural elements help lower insurance premiums and provide added security of your home. Close to local parks, Seminole County "A" Rated Schools, main shopping areas, major roadways for easy commuting. and exciting attractions and destinations for all ages. Perfect for every kind of buyer: seasonal residents can enjoy locking up and leaving, not having to worry about maintenance, collegiate students, checks all the boxes for first time home-buyers, empty-nesters downsizing, or anyone looking for comfortable carefree living.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-585-0500)
Listing Agent: Linda Bain (407-474-5269)
143 HAYES RD, WINTER SPRINGS, FL 32708
$479,00032 Days on yellowkey MLS ID: O6407546
REDUCED by $10,000 (2.0%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1649 Built: 1983 Tax: $1,782 (2024)Community: North Orlando Ranches Sec 02ASingle Family
Taxes:$1,782
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)
819 DUNDEE DR, WINTER SPRINGS, FL 32708
$429,00013 Days on yellowkey MLS ID: O6412585
INCREASED by $4,000 (0.9%) on 06/05/2026
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
Elementary School: Highlands Elementary
Middle School: South Seminole Middle
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)
268 TAVESTOCK LOOP, WINTER SPRINGS, FL 32708
$569,90033 Days on yellowkey MLS ID: O6407307
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2415 Built: 2001Monthly Fee: $150 Tax: $4,293 (2025)Community: ParkstoneSingle Family
Taxes:$4,293
Elementary School: Layer Elementary
Remarks: PHOTOS COMING SOON**268 Tavestock Loop, Winter Springs, FL 32708** Perfectly situated in the heart of Winter Springs, this stunning 4-bedroom, 2.5-bathroom home offers the ideal location with easy access to shopping, dining, theme parks, major roads, and the airport. Nestled within a desirable gated community, you'll enjoy peace of mind along with fantastic amenities including a community Lake Jess Up, pool, park, and 2 playground walking path, community benches. Step inside this beautiful two-story home and immediately notice the high ceilings that create a bright, open atmosphere throughout. Hard flooring runs seamlessly from room to room, giving the entire 2,883 square feet a clean, modern feel that is both stylish and easy to maintain. The kitchen is equipped with sleek stainless steel appliances, making it the perfect space to prepare meals and gather with family and friends. With four spacious bedrooms, there is plenty of room for everyone. The primary bedroom offers a comfortable retreat after a long day, while the additional bedrooms provide flexible space for family, guests, or a home office. Two full and half bathroom ensure convenience for the entire household. This move-in ready home means no waiting and no hassle. Simply unpack and start enjoying everything this wonderful property and community have for you. Whether you are relaxing by the community pool, taking the family to the playground, walking trails, Lake Jess Up or exploring all that Central Florida has in store, this home puts it all within reach. Don't miss your chance to make 268 Tavestock Loop your new home. Schedule your private showing today!
Listing is courtesy of: FUSILIER REALTY GROUP (407-476-0476)
Listing Agent: Zep Bholai-Lawrence (321-689-3467)
30 SABLE CT, WINTER SPRINGS, FL 32708
$569,000123 Days on yellowkey MLS ID: O6382648
REDUCED by $10,000 (1.7%) on 04/12/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2674 Built: 1976 Tax: $3,043 (2024)Community: TuscawillaSpa: NoSingle Family
Taxes:$3,043
Remarks: REDUCED! Beautiful Executive 4 bedroom POOL home in Tuscawilla Country Club Golf Community! NO HOA! Mediterranean feel with wrought iron accents and courtyard. Huge Kitchen with island in the middle. All appliances. Hot water heater 2017. Lots of cabinet space. Spacious eat-in area beside kitchen. Formal Dining and Living rooms. Large bedrooms. Big Owners bedroom with walk-in closet and updated bath. Inside laundry room. Large Pool (updated to salt system) 8 feet deep. Big fenced yard. Screened in porch. Oversized 2 car side entrance garage (currently part of garage is an office but could easily be converted back). Community allows golf carts. Plenty of room to park jet skis, boats, and RV. Great location near shopping, restaurants, hospital, and major roads. Good schools. Country Club has golf, tennis, swimming, and dining membership. Trotwood park has basketball and tennis courts, soccer field, and covered picnic area. Many parks in neighborhood. Close to Seminole Trail for walking and bike riding. Move right in! Must Seee!
Listing is courtesy of: HOME SOLD NETWORK LLC (407-257-6223)
Listing Agent: Julie Bailey (407-257-6223)
421 HORIZON DR, WINTER SPRINGS, FL 32708
$294,900109 Days on yellowkey MLS ID: O6384932
REDUCED by $5,000 (1.7%) on 06/14/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1069 Built: 1998Monthly Fee: $142 Tax: $3,681 (2025)Community: Seasons TheSingle Family
Taxes:$3,681
Elementary School: Winter Springs Elementary
Remarks: Welcome to 421 Horizon Drive in Winter Springs, located in The Seasons community. This move-in ready home checks all the big boxes upfront: a 50-year Rhino shingle roof (2019), a 3.5-ton 14 SEER AC unit with heat pump and updated ductwork, a new electric panel, and a 2019 water heater. Beautifully maintained and thoughtfully updated throughout, this one-story home offers 3 bedrooms, 2 bathrooms, and 1,069 square feet of living space. Inside, you'll find newer Mohawk laminate flooring in the main living areas and bedrooms, tile in the kitchen and baths, updated light fixtures, newer ceiling fans, upgraded baseboards, and modernized doors and hardware throughout. The primary suite features a fully renovated bathroom with a walk-in shower, glass enclosure, rain shower head, and updated vanity. The guest bathroom has also been extensively renovated. High and vaulted ceilings enhance the open great room and dining space, while the sliding glass doors lead to an extended and stamped concrete patio within a private vinyl fenced yard, ideal for relaxing or entertaining. Located on a quiet cul-de-sac with assigned parking and curb parking available, this home is just a short walk to the community pool and directly across from the park, playground, and tennis courts. The HOA covers lawn maintenance, making for easy, low-maintenance living in a prime Seminole County location zoned for Winter Springs schools.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Peter Luu (321-917-7864)
101 MELTON DR, WINTER SPRINGS, FL 32708
$285,00014 Days on yellowkey MLS ID: O6413054
Bed: 4 Bath: 1.5 Liv Area Sq Ft: 1212 Built: 1959 Tax: $1,792 (2025)Community: Williamson HeightsSingle Family
Taxes:$1,792
Remarks: Charming 4-Bedroom Home in the Heart of Winter Springs! Welcome to this well-positioned 4-bedroom, 1.5-bath home offering comfort, functionality, and a spacious lot in an established Winter Springs neighborhood. Situated on nearly a quarter acre, this property provides plenty of outdoor space for entertaining, gardening, pets, or future enhancements. Inside, you'll find a practical floor plan with ample living space, natural light, and flexibility for today's lifestyle needs. The generous backyard offers endless possibilities for creating your own outdoor oasis. Conveniently located near shopping, dining, parks, major roadways, and top Seminole County amenities, this home presents an excellent opportunity for first-time buyers, investors, or anyone looking to add their personal touch. Don't miss your chance to own a property with great potential in one of Central Florida's most desirable communities!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Ariel Vargas (407-558-5161)
577 WALDEN CT, WINTER SPRINGS, FL 32708
$405,0008 Days on yellowkey MLS ID: V4949540
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1560 Built: 1974 Tax: $3,414 (2025)Community: Walden TerraceSingle Family
Taxes:$3,414
Middle School: Tuskawilla Middle
Remarks: NO HOA Corner Lot Single Family Home features 4 beds, 2 baths. Open layout design home with tons of upgrades: Windows replaced back in 2020, ROOF replaced in 2022, Water Heater replaced 2025, Luxury Vinyl floors installed 2026. BRAND NEW INTERIOR PAINT gives a clean look. The kitchen is the focal point of the house. It features subway tiles EXHAUST FAN, STAINLESS STEEL APPLIANCES and cabinets. GRANITE COUNTER TOP installed in 2019 and a brand new fridge 2026. Bathroom with brand new glass doors and brand new bath tub. AC unit installed 2017. A fully fenced yard provides privacy with expansive open space ready for outdoor entertaining and dining space, gardening, play area, fire pit area and also has a chicken coop and chicken run area. All outdoor furniture plus the BBQ grill are included with the sale. 2 car garage and metal husky shelves for storage. Zoned for Seminole County top A rated schools. The property is located in a minimal flood risk area (Zone X). Schedule your viewing today.
Listing is courtesy of: RISE REALTY OF FLORIDA LLC (386-804-4114)
Listing Agent: Nicole Garcia Lozada (787-235-4293)
1115 ARBOR GLEN CIR, WINTER SPRINGS, FL 32708
$750,0004 Days on yellowkey MLS ID: O6416243
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2608 Built: 1993Monthly Fee: $58 Tax: $5,397 (2025)Community: Tuscawilla Parcel 90Spa: NoSingle Family
Taxes:$5,397
Remarks: A perfect blend of comfort, style, and location. This beautifully maintained, custom 4-bedroom, 3-bath POOL home in the Tuscawilla community of Arbor Glen checks all the boxes. Spanning 2,620 square feet, this one-story, 3-car side-entry garage home offers the privacy of a fully fenced backyard with screened-in pool and no rear neighbors. After a refreshing swim in the NEWLY RESURFACED POOL (5/26), you can rinse off in the outdoor shower or step into the cabana bath with direct access from the patio. This split floor plan includes vaulted ceilings that create an airy atmosphere throughout, and the primary suite offers private lanai and pool access, perfect for morning coffee. The 4th bedroom is both functional and versatile, with a built-in desk/workstation and a queen-size Murphy bed. The large kitchen boasts stainless steel appliances, granite countertops, and a bright breakfast nook with a frameless bay window overlooking the pool. All the main living areas and bedrooms feature rich wood flooring. Other noted features: BRAND NEW POOL PUMP (5/26), freshly painted pool deck, washer/dryer included, gas fireplace, and newer roof (2020) & A/C (2019). Nestled in the desirable Seminole County school zone, with easy access to shopping, dining, parks, golfing at Tuscawilla Country Club, and pickleball at Central Winds Sports complex. This home has it all!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Ericka Stephens (407-468-0510)
140 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708
$769,90075 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)
472 DEWARS CT, WINTER SPRINGS, FL 32708
$499,90012 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
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)
568 BUCKHORN DR, WINTER SPRINGS, FL 32708
$485,0008 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)
984 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708
$410,00020 Days on yellowkey MLS ID: O6410083
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1821 Built: 1985Monthly Fee: $3 Tax: $3,100 (2025)Community: Oak Forest Unit 4Single Family
Taxes:$3,100
Remarks: Virtually Staged. A spacious 3-bedroom, 2-bathroom home located in the highly sought-after community of Oak Forest in Winter Springs. Known for its beautiful tree-lined streets, mature oak trees, and quiet suburban charm, this family-friendly neighborhood also offers access to top-rated schools and is conveniently located near popular restaurants, shopping, and everyday conveniences. Inside, this home features a versatile and functional floor plan with a spacious family room, separate living room, dining room, large kitchen, dedicated office space, and an indoor laundry room. The detached shed provides the perfect opportunity for extra storage, a workshop, or hobby space. Step outside to enjoy the private backyard complete with a fire pit — ideal for relaxing or entertaining guests. The garage has been split into an office and storage space but can be converted back into a two car garage. Major upgrades and improvements include an updated roof (2018), gutters(2018), HVAC system(2022), windows(2020), garage door(2020), hot water heater(2021), electrical panels(2023), and added insulation(2019). Additional features include an indoor electric fireplace (2022), and numerous updates throughout, offering peace of mind and move-in-ready convenience. Call today to schedule your private tour!
Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)
Listing Agent: Kelsey Payton (407-718-2967)
1702 DAVENPORT CT, WINTER SPRINGS, FL 32708
$569,90060 Days on yellowkey MLS ID: O6398359
REDUCED by $10,000 (1.7%) on 06/12/2026
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2101 Built: 1994Monthly Fee: $42 Tax: $7,266 (2024)Community: Davenport GlenSpa: NoSingle Family
Taxes:$7,266
Remarks: Discover the perfect blend of comfort and convenience in this beautifully refreshed 3-bedroom, 2-bathroom pool home. Boasting a spacious 3-car garage and a sought-after split floor plan, this residence has been revitalized with fresh interior and exterior paint. Experience the ultimate Florida lifestyle—spend your weekends lounging by your private pool or walk across the street to Sam Smith Park. Located just one mile from t Tuscawilla Country Club and zoned for top-rated Seminole County schools (Oviedo High and Indian Trail Middle), this home offers the lifestyle you’ve been searching for.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Hossin Mosaddad (407-949-1249)
1447 BIRD RD, WINTER SPRINGS, FL 32708
$2,625,000102 Days on yellowkey MLS ID: O6388126
REDUCED by $174,000 (6.2%) on 06/03/2026
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 6132 Built: 2026 Tax: $2,989 (2024)Community: Talis CrossingSingle Family
Taxes:$2,989
Remarks: 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.
Listing is courtesy of: MAVREALTY (727-314-3942)
Listing Agent: Robert Kirkwood, Iv (321-297-6489)
214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708
$600,000115 Days on yellowkey MLS ID: O6372400
REDUCED by $25,000 (4.0%) on 06/03/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2474 Built: 2001Monthly Fee: $42 Tax: $5,539 (2024)Community: Chestnut Ridge In TuscawillaSpa: NoSingle Family
Taxes:$5,539
Elementary School: Rainbow Elementary
Remarks: WOW, BEST PRICE IN Winter Springs inside Executive TUSCAWILLA! Incredible opportunity. Here is your future DREAM HOME! Best price DIRECT GOLF FRONT HOME IN ORLANDO! Why wait to build on a 50 ft lot when you can live in a custom home Did you ever dream of drinking your Coffee daily while looking at a pristine GOLF course and Conservation view? Maintenance free yard that is DIRECTLY on the 16th hole of the Tuscawilla Golf Course. Builder of this neighborhood built this One of a kind home for himself and it has a one of a kind view. VIEW VIDEO WALK THROUGH TOUR. Energy Efficient SOLAR that is PAID FOR! Chestnut Ridge is a serene Winter Springs community in Seminole County This exquisite property, situated on .24 acres of loads of landscaping, with amazing azaleas with many colors, is the epitome of luxury living, perfect for executive families seeking a harmonious blend of comfort and elegance. Boasting an impressive 4 bedrooms and 3 bathrooms, this custom-built home offers a spacious upstairs private en suite featuring 1 bedroom and 1 bath, ideal for guests, playroom or a secluded home office. A true Gardeners Paradise. The interior is nothing short of breathtaking with soaring 10’ ceilings and solid red oak flooring that greets you in the foyer and extends through the kitchen and breakfast nook. The heart of the home, a chef's kitchen, is adorned with quality chestnut wood cabinets, sleek granite countertops, and a wet bar island, perfect for entertaining. Hallway complete with bright skylights that lead to bedroom 2 and 3 that actually both have access to the hall Jack n Jill bath. Three way split floor-plan offers loads of lifestyle options. Attention to detail is evident with 5 1/4” baseboards, recessed lighting, and a luxurious custom built-in entertainment center. Cozy up by the gas-burning fireplace or enjoy the oversized 860 SF 3-car garage/workshop, equipped with an insulated ceiling and reinforced garage doors, offering ample space for vehicles and projects alike. Custom Built pergola off the garage offers additional charm. So Many options. Complete with a direct wire for a generator access. The master suite is a sanctuary with a generous 8' x 12' walk-in closet featuring custom solid walnut cabinets. Bask in the Florida sunshine on your awning-covered rear deck with a view of the golf course and conservation area. Built in 2001 with a new roof in 2020, this move-in ready home benefits from top-of-the-line “Low E” windows, R-30 attic insulation. Yard is LOW MAINTENANCE! Location is paramount, with proximity to quality schools, shopping, dining, and major employment hubs.You are upgrading your LIFESTYLE in this neighborhood. HIGHLIGHTED EXTRAS Throughout. Along with the purchase this home comes with 20 solar panels, that are PAID FOR, which can provide 7.8 kWh are connected with the Duke power grid. The electric bill reflects how much power you use and how much you push back to the grid. You are credited equally for power pushed back in the final monthly amount due. Additionally, there is a backup battery which in the event of power outage will provide 6 dedicated circuits for the house with standby power during brief power outages."A" Rated schools, all three! A MUST SEE!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Laurie Cain (407-484-9944)
4901 PETRA CT, WINTER SPRINGS, FL 32708
$674,90018 Days on yellowkey MLS ID: O6412001
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2644 Built: 1986Monthly Fee: $40 Tax: $2,783 (2024)Community: TuskabaySingle Family
Taxes:$2,783
Remarks: Make yourself at home in this spacious, beautifully undated residence located in one of the most desirable and sophisticated neighborhoods in Winter Springs, in the heart of Central Florida. This spacious four bedroom, two bath split-plan home offers comfort and versatility throughout . Features include a formal dining room; inviting Florida room, private den, and a generously sized master suite designed for relaxation. With a thoughtful layout and plenty of space, this home is perfect for both everyday living and entertaining. All kitchen appliances are included featuring 42" custom, cabinetry, carpet in the living room and all bedrooms. Bamboo flooring in the sunroom and office with ceramic tile in the kitchen, bathrooms and laundry room (with pull-down ironing board). The living room features an electric fireplace, built in bookshelves, vaulted ceiling, that creates a warm and inviting atmosphere in the heart of the home. Move in ready. Roof; 2016, AC/heat pump; 12/24, microwave; 2026, electric box; 1/2025, replumbed entire house; 2023.
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)
Listing Agent: Pat Long (407-406-6733)
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