Location: Winter Springs
Keyword(s): Winter Springs High
Keyword(s) High School: Winter Springs High
Do Not Show Listings
130 E BAHAMA RD, WINTER SPRINGS, FL 32708
$725,00044 Days on yellowkey MLS ID: O6398011
0 Days Off yellowkey (back on 5/9/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2158 Built: 1991 Tax: $3,366 (2024)Community: Bahama RanchesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,366
Elementary School: Winter Springs Elementary
High School: Winter Springs High
Tax Year: 2024
Middle School: Indian Trails Middle
Remarks: Under contract-accepting backup offers. Don’t miss the opportunity to see this exceptional property! Located in the desirable Ranchlands neighborhood of Winter Springs, this exceptional property sits on over 1.5 acres of land, offering both space and privacy. A large circular driveway provides easy access and ample parking. This well-maintained home features 4 bedrooms, 2 bathrooms, and over 2,100 square feet of living space, with a split floor plan ideal for both everyday living and entertaining. As you enter, you’re welcomed by a bright, open interior showcasing tile flooring throughout the home, high ceilings, and an abundance of natural light. The upgraded kitchen is a standout, featuring stainless steel appliances, granite countertops, plenty of cabinet storage and a kitchen nook. The spacious family room includes a cozy fireplace, along with a mounted TV and surround sound system that will convey with the home. The primary suite offers private access to the backyard through sliding glass doors, a walk-in closet, and a generously sized en-suite bathroom complete with dual sinks, and a tub/shower combo. Step outside to enjoy the expansive covered lanai—perfect for relaxing or entertaining—along with a 30' above-ground pool to enjoy Florida’s warm weather and a play area for the little ones. Additional upgrades include a home generator, AC and septic tank and pump all installed in 2017, a water heater in 2018, pool in 2020, roof in 2021 and pool pump in 2026. In addition to the attached 2-car garage, the property also features a 25' x 30' detached garage equipped with electricity and AC—ideal for extra vehicles, a workshop, or storage. A side-entry gate provides access for RV or boat parking to store in your backyard. With no HOA, you’ll enjoy the flexibility to use the property as a primary residence, investment, or income-producing opportunity. This hidden gem offers a peaceful, country-style setting while still being conveniently located near major roads, shopping, and dining. Come see it today and make it yours!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Zac Hernandez (407-576-7622)
10 MOREE LOOP #3, WINTER SPRINGS, FL 32708
$135,000108 Days on yellowkey MLS ID: O6381696
1 Days Off yellowkey (back on 5/8/2026)
REDUCED by $10,000 (6.9%) on 04/02/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1080 Built: 1973Monthly Fee: $413 Tax: $2,066 (2024)Community: Bay Tree Sec 10Condo
Taxes:$2,066
Elementary School: Highlands Elementary
Middle School: South Seminole Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. You will LOVE living in Baytree, a towhome styled condominium community in the desirable Highlands of Winter Springs! This home has been well loved and owned by the same owner for many years and is ready for YOU to make it YOURS. Offering a great floor plan and lots of space with a screen enclosed back porch and covered entry. Two large bedrooms on the 2nd floor and a convenient half bath on the first floor. Ample storage space! Appliances include NEW water heater (2026), washer/dryer, refrigerator, range and dishwasher! The Highlands community offers great amenities including a community pool, tennis/pickleball courts and walking trails! Located in Winter Springs and VERY close to Lake Mary, Maitland and major roads, shopping and dining. Ready to make your dreams of homeownership a reality? Schedule a tour today!
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Carla Stanton (321-356-3370)
476 CLUB DR, WINTER SPRINGS, FL 32708
$275,00067 Days on yellowkey MLS ID: O6392856
2 Days Off yellowkey (back on 5/8/2026)
REDUCED by $10,000 (3.5%) on 04/22/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1460 Built: 1995Monthly Fee: $520 Tax: $1,765 (2025)Community: Cypress ClubTownhouse
Taxes:$1,765
Tax Year: 2025
Remarks: Under contract-accepting backup offers. Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy the benefits of a 2020 A/C system, a full repipe completed in 2016, a 2016 water softener, and an electric water heater approximately 9 years old. Even better, a brand-new roof is currently being installed and is fully covered by the HOA—adding long-term value and convenience. Inside, you’ll find an inviting layout with knockdown ceilings throughout the main level and an open living and dining area tucked toward the rear of the home for added privacy. Updated recessed lighting enhances the space, creating a warm and welcoming atmosphere. Just beyond, a step-down enclosed patio offers a serene retreat overlooking wooded views—perfect for relaxing or entertaining. The flexible floor plan includes a downstairs bedroom with an adjacent full bath, ideal for guests, a home office, or multi-generational living. Upstairs, two generously sized bedrooms feature soaring ceilings and abundant natural light. The primary suite offers ample closet space and tranquil views of the surrounding greenery, along with a spacious en-suite bath complete with a Jacuzzi tub and separate shower—perfect for unwinding after a long day. Cypress Club stands out as the only neighborhood within The Highlands with its own private pool, in addition to access to the community’s extensive amenities. Residents enjoy multiple pools, tennis courts, scenic walking trails, parks, pavilions, BBQ areas, a clubhouse, as well as volleyball and basketball courts—delivering a true Florida lifestyle right outside your door. Don’t miss this opportunity to own a move-in-ready home in one of Winter Springs’ most desirable communities!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Jeff Singletary (407-383-1933)
335 KIRKCALDY DR, WINTER SPRINGS, FL 32708
$339,90025 Days on yellowkey MLS ID: O6400818
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1178 Built: 1984Monthly Fee: $36 Tax: $3,693 (2025)Community: Highland Village 1Single Family
Taxes:$3,693
Remarks: Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new electrical panel inside and outside. The generously sized primary bedroom includes a built-in California Closets system, providing stylish and highly functional custom storage. The secondary and third bedrooms are also well-sized—perfect for guests, family, or easily converted into a home office. Washer and dryer are included in the sale. Enjoy the covered and screened lanai overlooking a charming New Orleans-style courtyard with pavers, a firepit, and a lamp post. The oversized, fully fenced, and cleared backyard offers plenty of space to relax, entertain, or garden, providing a strong sense of privacy. The Highlands is a highly sought-after, established community with low HOA fees and beautiful mature trees throughout. Amenities include an Olympic-size community pool, walking trails, playground, tennis court, volleyball court, and a clubhouse. Ideally situated just off State Road 434 Florida and Tuskawilla Road, this home offers quick access to Winter Springs Town Center for shopping and dining, and is just a short stroll from Torcaso Park—a lively neighborhood park featuring basketball courts, soccer and football fields, playgrounds for all ages, a splash pad, sand play areas, and picnic pavilions, perfect for both active days and relaxed family outings.
Listing is courtesy of: MILLENIUM REALTY GROUP (407-277-1400)
Listing Agent: Irina Carp (407-969-9937)
607 CASA PARK COURT K, WINTER SPRINGS, FL 32708
$239,90032 Days on yellowkey MLS ID: O6402801
0 Days Off yellowkey (back on 5/5/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1088 Built: 1985Monthly Fee: $207 Tax: $1,556 (2024)Community: Casa Park Villas Ph 2Townhouse
Taxes:$1,556
Elementary School: Keeth Elementary
Remarks: Under contract-accepting backup offers. Welcome home to this beautifully reimagined 2-bedroom, 2-bath townhome in the heart of Winter Springs. From the moment you step inside, you’re greeted by a bright, open-concept layout that seamlessly connects the family room, dining area, and kitchen—creating a warm, inviting space perfect for both everyday living and entertaining. Every detail has been thoughtfully updated, featuring luxury vinyl flooring throughout, fresh modern paint, and a stunning, fully renovated kitchen complete with brand-new cabinetry, sleek countertops, and stainless steel appliances. The result is a clean, contemporary feel that’s as stylish as it is functional. Upstairs, you’ll find a serene primary suite along with a spacious second bedroom, offering comfort and privacy. The bathroom has been completely transformed with elegant marble flooring, adding a touch of luxury to your daily routine. Step outside to your large, screened-in covered patio—an ideal retreat for morning coffee, evening relaxation, or hosting friends in a peaceful outdoor setting. Beyond the beauty, this home offers peace of mind with major upgrades already taken care of, including a brand-new A/C (2026), new Pella double-pane high-impact windows, and a tankless water heater (2026). Located in a desirable community close to parks, scenic trails, dining, shopping, top-rated schools, and major highways, this home truly delivers the perfect blend of comfort, convenience, and value. This isn’t just a townhome—it’s a place where you can settle in, unwind, and feel at home from the very first moment.
Listing is courtesy of: KGV REALTY GROUP (407-474-0844)
Listing Agent: Kristin Vogt Pllc (407-417-7206)
788 ANDOVER CIR, WINTER SPRINGS, FL 32708
$445,00046 Days on yellowkey MLS ID: O6397299
0 Days Off yellowkey (back on 5/6/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1791 Built: 1994Monthly Fee: $124 Tax: $3,567 (2025)Community: Georgetowne Unit 3Single Family
Taxes:$3,567
Remarks: Welcome to this beautiful home in the sought after TUSCAWILLA community of Georgetowne. Step into a home that immediately feels WARM, INVITING, and designed for both everyday living and effortless entertaining. Upon entering you are greeted by a SPACIOUS LIVING ROOM filled with NATURAL LIGHT & high ceilings. SLIDING GLASS DOORS off the main living area create the perfect flow for both everyday living and entertaining. The heart of the home is the well-appointed kitchen featuring GRANITE COUNTERTOPS and STAINLESS STEEL APPLIANCES, white cabinets offering both style and functionality. The breakfast bar is perfect for casual dining. Just off the kitchen, the FORMAL DINING AREA is highlighted by LARGE WINDOWS that bring in an abundance of light, creating an inviting setting for meals and gatherings. A dedicated LAUNDRY ROOM with BUILT-IN SHELVING and additional STORAGE is conveniently located off the TWO-CAR GARAGE, adding to the home’s practical layout. The PRIMARY SUITE is a true retreat, offering generous space, a WALK-IN CLOSET WITH BUILT-INS, and PRIVATE ACCESS to the patio through sliding doors. The en-suite bathroom features a relaxing GARDEN TUB and a WALK-IN SHOWER, providing both comfort and convenience. Bedrooms two and three include BUILT-IN CLOSETS and share a SECONDARY BATHROOM with a TUB/SHOWER COMBINATION. Throughout the home, you will find WOOD FLOORING in the main living areas and bedrooms, with TILE in the kitchen, dining, and laundry spaces for easy maintenance. Step outside to enjoy the enclosed back sunroom, perfect for relaxing while overlooking the backyard. UPDATES include ROOF 2023, NEW HOT WATER HEATER, BRICK PAVER DRIVEWAY, Newer WOOD Front Door, fresh paint in kitchen & dining room. Ideally situated just steps from TROTWOOD PARK, this home offers incredible access to TENNIS COURTS, PICKLEBALL, PLAYGROUNDS, and OPEN GREEN SPACE. Conveniently located to Winter Springs Town Center, 417, shops, restaurants and more! With its unbeatable location, thoughtful layout, and inviting features, this home truly offers the best of TUSCAWILLA LIVING. Schedule your private showing today before it's too late.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Dawn Tinder (407-733-6846)
1452 CONNORS LN, WINTER SPRINGS, FL 32708
$475,00026 Days on yellowkey MLS ID: O6404505
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1766 Built: 1986Monthly Fee: $90 Tax: $4,752 (2024)Community: Wedgewood Tennis VillasSingle Family
Taxes:$4,752
Remarks: Welcome to 1452 Connors Lane, a beautifully updated home in the heart of Tuscawilla, one of Winter Springs’ most established and sought-after communities. From the moment you walk in, you’ll notice the open layout, soaring ceilings, and natural flow that make this home feel both spacious and inviting. The kitchen has been thoughtfully renovated with updated cabinetry, updated appliances, and stunning quartzite countertops, creating a space that is both functional and eye-catching. The bathrooms have also been fully redone with timeless finishes, offering a fresh and elevated feel throughout the home. This property has been meticulously improved over the years, including a new roof and gutters in 2022, interior paint in 2022, and fully renovated bathrooms in 2024. In 2025, the owners completed several major upgrades that truly set this home apart, including ceramic wood-look tile flooring, a brand new wood board-on-board fence, and a fully reimagined outdoor space. The rear patio features cedar tongue and groove detailing with cedar pillars, creating a warm and inviting outdoor living area. The backyard has been completely transformed with pavers throughout, a widened driveway, and artificial turf designed with pets in mind. Additional updates include newer windows and sliding glass doors, bringing in great natural light while improving efficiency. Beyond the home itself, Tuscawilla offers a lifestyle that is hard to beat. Known for its tree-lined streets, golf course community feel, and access to top-rated Seminole County schools, this neighborhood attracts buyers looking for both charm and convenience. Residents enjoy nearby parks, the Tuscawilla Country Club, walking and biking trails, and easy access to shopping, dining, and major roadways. Homes with this level of updates in Tuscawilla do not come around often, making this a rare opportunity to move right in and enjoy everything this community has to offer.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Denise Mckinley (407-625-0635)
4951 COURTLAND LOOP, WINTER SPRINGS, FL 32708
$690,000135 Days on yellowkey MLS ID: O6374007
REDUCED by $10,000 (1.4%) on 05/05/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2562 Built: 1984Monthly Fee: $40 Tax: $7,807 (2024)Community: Tuskabay Ph 1Single Family
Taxes:$7,807
Remarks: This beautifully updated home blends timeless character with modern comfort, offering an inviting layout designed for both everyday living and entertaining. The light-filled interior showcases a stunning, renovated kitchen with new quartz extended countertops, a butcher block island, recessed lighting, and a full suite of high-end appliances including a JennAir refrigerator, KitchenAid pull-out refrigerator and freezer with ice maker, double oven and stovetop, wine and beverage cooler, and dishwasher. Major system upgrades add peace of mind and efficiency, featuring a newer roof installed in 2021, a fully paid off 11.745 kW (DC) solar system paired with a Tesla Powerwall 2.1 (7 kW DC battery capacity), whole-home water filtration and softener, high-efficiency heat pump water heater, new double-paned windows, Nest thermostats for upstairs and downstairs climate control, upgraded outlets with USB and modern switches, and new blinds throughout. The spacious primary bathroom has been fully remodeled with glass shower doors, new quartz countertops, and a farmhouse sink. Outside, enjoy exceptional curb appeal and a private backyard retreat with a screened-in pool, expansive paver patio, new extended paver walkway wrapping around the backyard, upgraded irrigation and sprinkler system, new gutters, and recently serviced chimney. The property is framed by mature, recently trimmed water and live oaks, enhancing both beauty and shade, while added features such as a new front door with wide extended entry, exterior Ring cameras and floodlights complete this truly move-in-ready home designed for a seamless indoor-outdoor Florida lifestyle.
Listing is courtesy of: MOMENTUM REALTY (904-903-1558)
Listing Agent: Carolina Taborda (832-349-8266)
50 SHEOAH BLVD #33, WINTER SPRINGS, FL 32708
$179,50026 Days on yellowkey MLS ID: O6404380
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 972 Built: 1973 Tax: $1,726 (2025)Community: Sheoah Sec 1Condo
Taxes:$1,726
Remarks: WELCOME HOME! This elegant, bright, and open first-floor, single-story 2-bedroom, 2-bath condo is located in the highly desirable Winter Springs community. From the moment you step inside, you’ll feel right at home in the spacious living and dining area featuring custom-built shelving and an inviting layout perfect for relaxing or entertaining. The split-bedroom floor plan offers added privacy, with sliding doors from the primary suite leading to a charming brick patio, ideal for enjoying your morning coffee or unwinding in the evening. The kitchen has been beautifully renovated with new appliances, updated countertops, and ample workspace. The primary bathroom features a walk-in shower with safety grab bars, while the guest bathroom includes a tub, with a convenient laundry area located in the guest bath closet. A bright and airy enclosed Florida room with A/C provides flexible space for a home office, reading nook, or additional living area. Step outside to your private patio with room for outdoor furniture, plants, or even your own garden retreat, all overlooking a peaceful wooded conservation area. Additional highlights include approximately 1,196 square feet including the enclosed porch, a newer A/C and water heater, fresh interior paint in a modern light gray, and no carpet throughout. Located in The Highlands, a quiet and friendly community offering a pool, tennis courts, parks, walking trails, scenic water views, reserved parking, and community mailboxes. HOA fees include high-speed internet, cable, pest control, and full grounds maintenance, with weekly lawn care and twice-weekly trash pickup. The home is situated in a top-rated school district with schools nearby and is just minutes from shopping, dining, and everyday conveniences. Schedule your private showing today, this one won’t last long!
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Fanny Stollmeyer (704-905-0698)
600 NORTHERN WAY #302, WINTER SPRINGS, FL 32708
$275,00052 Days on yellowkey MLS ID: O6396912
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1425 Built: 1981 Tax: $4,268 (2025)Community: Tuscany Place Ph 1Condo
Taxes:$4,268
Remarks: One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer ~ Welcome to Tuscany Place, a GATED COMMUNITY in the heart of Tuskawilla – one of Winter Springs’ most desirable and established areas! This UPDATED second-floor condo delivers the perfect blend of modern style, LOW MAINTENANCE LIVING, and an unbeatable Central Florida location. Major updates are already done for you, including the kitchen and both bathrooms, plus a NEWER A/C (2020), giving peace of mind from day one. Inside, the home has been tastefully updated with modern finishes and fixtures, creating a clean, MOVE-IN READY space that feels both fresh and inviting. WOOD LAMINATE FLOORING flows throughout the entire unit, enhancing the seamless, low-maintenance lifestyle. The OPEN CONCEPT living and dining area is filled with NATURAL LIGHT thanks to a wall of SLIDING GLASS DOORS that lead to a SCREENED BALCONY overlooking peaceful green space – perfect for morning coffee or winding down in the evening. The UPDATED KITCHEN stands out with a fresh, modern color palette and a pop of personality, featuring sleek countertops, STAINLESS STEEL APPLIANCES, ample cabinet storage, a breakfast bar, and a window that brings in even more natural light. The SPLIT BEDROOM layout offers both comfort and privacy with the primary suite tucked away at the back of the home, complete with a WALK-IN CLOSET, updated en-suite bath, and its own private access to a SECOND BALCONY. Two additional bedrooms are positioned at the front of the unit and share a beautifully updated full bath, ideal for guests, family, or a home office setup. Tuscany Place residents enjoy a gated entrance along with added conveniences like lawn care and pest control, making this a truly low-maintenance option. The location is hard to beat – just minutes from Tuskawilla Road, SR 434, and 417, with easy access to TROTWOOD PARK, Central Winds Park, Tuscawilla Country Club, and all the shopping and dining options in Winter Springs and nearby Oviedo. Whether you are looking for your next home or a smart investment, this updated condo is priced to sell and ready for its next owner. Call today to schedule a tour!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
1029 E PEBBLE BEACH CIR, WINTER SPRINGS, FL 32708
$395,00029 Days on yellowkey MLS ID: O6404082
0 Days Off yellowkey (back on 5/4/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1314 Built: 1993Monthly Fee: $117 Tax: $1,736 (2025)Community: Country Club Village Unit 3Single Family
Taxes:$1,736
Remarks: Welcome home to this charming 3-bedroom, 2-bath residence in the desirable community of Country Club Village. This home features a split bedroom floor plan and a kitchen large enough for a breakfast nook. Enjoy your morning coffee on either of the TWO screened porch areas. Located in the heart of Winter Springs, you are minutes from top-rated Seminole County Schools, parks, shopping, and the Tuscawilla Country Club golf course. Barrel tile roof and plumbing NEW in 2023!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Stephanie Kovats (407-694-6594)
903 TORREY PINE DR, WINTER SPRINGS, FL 32708
$469,900113 Days on yellowkey MLS ID: O6377459
1 Days Off yellowkey (back on 5/4/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1501 Built: 1998Monthly Fee: $126 Tax: $2,155 (2024)Community: Greenbriar Sub Ph 2Single Family
Taxes:$2,155
Elementary School: Rainbow Elementary
Remarks: Under contract-accepting backup offers. **NEW ROOF TO BE INSTALLED IN APRIL!!** Paradise found in Tuscawilla! Come fall in love with this idyllic low maintenance waterfront villa on over 1/3 acre with lawn care and community pool included. Walk out the back door of this beautiful 3 bedroom home to your “high and dry” oasis backing up to serene Howell Creek. Inside the home, you will be greeted by a cozy yet open floor plan with abundant light, high ceilings and many upgrades. Some outstanding features include a beautifully remodeled eat in kitchen with sleek white cabinetry, solid surface counter top, tile backsplash, and handsome stainless appliances. In addition, easy-care tile flooring is found throughout the main living areas and plush carpeting in the bedrooms. A dreamy master suite offers ample space and an elegant bathroom with walk in shower, soaking tub, and double vanity. The two additional bedrooms are quite private and spacious and are convenient to the full guest bath with spacious vanity and decorative tile. A large open great room leads to the screened porch for entertaining or just relaxing. Create your own secret garden inside the privacy fenced side yard which is very suitable for pets. Leading to the spacious 2 car garage, the laundry room conveniently includes a high quality washer and dryer. Residents of Greenbriar enjoy low-maintenance living along with access to a community pool, making it perfect to enjoy an easy lifestyle right at home. Located near the Tuscawilla golf course, this home is also just minutes from shopping, dining, and everyday conveniences, with easy commuter access to major roadways. Whether you’re a first-time homebuyer, looking to downsize, or searching for a move-in-ready opportunity in an established community, this home checks all the boxes. Don’t miss out on this slice of heaven with beautiful views, simplicity, and community—all in one exceptional property. This is a once in a blue moon opportunity, so pick up your phone and jump in your car today!
Listing Agent: Colleen Kahl (407-630-0027)
421 HORIZON DR, WINTER SPRINGS, FL 32708
$299,90092 Days on yellowkey MLS ID: O6384932
REDUCED by $15,100 (4.8%) on 04/29/2026
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
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)
936 TORREY PINE DR, WINTER SPRINGS, FL 32708
$420,00059 Days on yellowkey MLS ID: O6386843
0 Days Off yellowkey (back on 5/2/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1678 Built: 2000Monthly Fee: $126 Tax: $2,652 (2024)Community: Greenbriar Sub Ph 2Single Family
Taxes:$2,652
Remarks: Under contract-accepting backup offers. GOLF FRONT HOME IN TUSCAWILLA! Beautiful views and an open floor plan with updates galore make this one THE one! With lawncare, swimming pool and friendly neighbors included in the HOA, easy living is yours! Note: this home was built as a 3 bedroom, yet the previous owner converted the space to a 2 bedroom that can easily be converted back. You will adore the beautifully updated kitchen featuring a stunning glass backsplash, gorgeous granite countertops, custom pantry and stainless steel appliances. The open layout flows seamlessly through the front door to the living/dining space with a custom pass through to the kitchen that is wide open to the family room. From the kitchen, family room, primary suite, and all-weather porch, you can enjoy relaxing views of the 16th fairway on the Championship Tuscawilla Golf Course. Amazing assumable LOW interest financing is available to a qualified buyer. Full details are available. A spacious primary suite featuring a large walk-in closet with custom closet system and separate access to the rear porch. Fall in love with the handsome updated ensuite bath with spacious built in vanity, glass enclosed tiled walk in shower plus additional storage or vanity space where a bathtub was removed. Additional features and upgrades include new double pane sliding doors to the glass/ screened enclosed patio, ……… The brick paved driveway and spacious 2-car garage will keep your vehicles happy, while the recent updates and community amenities will make you very happy! As an option, Tuscawilla Country Club offers dining, exercise facility, junior Olympic pool, tennis courts and leagues, pickleball, golf and social events. Don't miss out on this great property! Visit today!
4910 E LAKE DR, WINTER SPRINGS, FL 32708
$2,399,00029 Days on yellowkey MLS ID: O6398929
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3657 Built: 1964 Tax: $6,256 (2024)Community: NaSingle Family
Taxes:$6,256
Elementary School: Sterling Park Elementary
Remarks: A truly rare find in Winter Springs. This equestrian-friendly, lakefront estate is complete with its own private tennis court, a solid block-constructed horse barn, and room to enjoy every part of the lifestyle. All of this, tucked in a quiet setting that keeps you close to the heart of Orlando, with the added benefit of being just 2 miles from The Geneva School, one of the area’s premier private education options. Originally built in 1964, the home was thoughtfully expanded in 1994, creating a larger, more functional layout while preserving its character. Today it offers over 3,000 SF overlooking the shimmering waters of Little Lake Howell. Enjoy west-facing sunset views framed by mature cypress trees. Host friends for tennis or pickleball right in your backyard. The sizeable horse barn was engineered for exceptional durability, built with block construction and poured concrete for maximum strength. The main home includes a 3-car garage, and the barn adds an oversized carport that can easily double as covered boat storage.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Kris Kennedy (813-947-3509)
600 NORTHERN WAY #1608, WINTER SPRINGS, FL 32708
$274,90099 Days on yellowkey MLS ID: G5108558
REDUCED by $5,100 (1.8%) on 05/01/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1425 Built: 1981Monthly Fee: $373 Tax: $2,582 (2025)Community: Tuscany PlaceCondo
Taxes:$2,582
Remarks: Very motivated sellers! Condo in Tuskawilla’s Tuscany Place •Discover comfort and convenience in Winter Springs’ Tuskawilla neighborhood. Tuscany Place is a gated community with a private pool, near Trotwood Park, Cross Seminole Trail, and top-rated schools. •Double Balcony (length of condo) •Corner unit with pool view •Updated kitchen w/stainless steel appliances •New water heater (2023) •New roof (2023) •New AC (2016) •Washer/dryer (2026) •Primary bedroom with walk-in closet, en-suite, and balcony access •Split floor plan for privacy. Seize this opportunity to own a beautifully updated condo in a prime location! FHA Approved Condo complex.
Listing is courtesy of: WORTH CLARK REALTY (352-988-7777)
Listing Agent: Kelly Boulton (407-906-8348)
709 SAILFISH RD, WINTER SPRINGS, FL 32708
$407,500177 Days on yellowkey MLS ID: O6364715
REDUCED by $5,000 (1.2%) on 05/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1737 Built: 1984 Tax: $5,463 (2024)Community: North Orlando Ranches Sec 10Spa: NoSingle Family
Taxes:$5,463
Elementary School: Layer Elementary
Remarks: Some neighborhoods offer just a house; this one delivers a true Florida lifestyle, anchored by a beautiful, deep quarter-acre lot and a home built for functional, everyday living. Tucked away in a quiet pocket of Winter Springs—one of Seminole County’s most coveted and safest communities—this 3-bedroom, 2-bathroom gem offers the rare freedom of no HOA combined with unparalleled privacy. The home provides immediate peace of mind with a roof that is only 5 years old. Set beneath a picturesque canopy of mature trees and draping Spanish moss, the curb appeal speaks to the established, friendly vibe that residents of Winter Springs enjoy. Step inside to a flexible layout built for flow, featuring dedicated living and family rooms that give everyone room to spread out. The central kitchen and dining space is positioned perfectly to serve both entertaining areas and acts as the heart of the home. The smart split-bedroom floor plan provides ideal separation, tucking the spacious primary suite on one side of the house for privacy and tranquility. The real magic happens where the indoors meets the outdoors. The home expands dramatically with a large, enclosed Florida Room (22'6" x 11'6") that is fully under A/C with its own dedicated mini-split unit—making this substantial bonus space a year-round extension of the living area, perfect for an office, gym, or sun-soaked den. This room leads directly out to a private, spacious backyard where you will enjoy the unique benefit of no rear neighbors, secured by a perimeter of mature trees and fencing. Even the garage has been elevated: the two-car garage features durable epoxy flooring and includes a dedicated laundry area and a useful closet room, perfect for home projects or tool storage. The location is the final mic drop. You are moments from the convenience of Winter Springs Town Center, Central Winds Park, and the premier amenities of the Tuscawilla area. You are also zoned for the excellent Seminole County School District. You get the quiet, safe suburban environment while maintaining effortless access to major highways (417/I-4) for a convenient commute to Downtown Orlando or Lake Mary. View the 3D Matterport tour now to fully appreciate the space and layout. This is more than a listing—it’s the home where your next chapter begins.
Listing is courtesy of: ELEGANT REALTY LLC (407-985-2840)
Listing Agent: Wayne Mottley (407-741-3804)
600 NORTHERN WAY #502, WINTER SPRINGS, FL 32708
$269,000443 Days on yellowkey MLS ID: O6286935
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1425 Built: 1985Monthly Fee: $397 Tax: $766 (2024)Community: Tuscany Place Ph 1Spa: NoCondo
Taxes:$766
Remarks: MOTIVATED SELLER!!! Seller offering concession toward buyer closing cost. Location! Location! Location! This pristine condo nestled in the heart of Tuscawilla offers an incredible opportunity for low maintenance living in a serene and gated community. Enjoy summer days by the beautiful community pool and relax in the cabana. Across the way you will find access to Trotwood Park, with its picturesque settings ideal for picnics and recreational activities. Featuring a pavilion, playground, splash pad, tennis courts, and sports fields, it's a hub for family fun. For outdoor enthusiasts, the nearby Seminole County Cross Trail is perfect for biking and walking. As you tour the well maintained 3-bedroom, 2-bathroom condo, it encompasses 1425 sqft of second level living with private screened balconies overlooking the courtyard. Well-appointed kitchen equipped with brand-new stainless-steel appliances: Counter-depth Smart French Door Refrigerator, Smart SLIM Microwave, Bespoke Induction Range with self and steam cleaning Air Fry Convection Oven. A generous living and dining area that are inviting and ideal for entertaining. The split floor plan offers privacy for the owner suite, complete with its own screened balcony. The secluded and spacious secondary bedrooms are delightful for guests, office space or a growing family. New AC installed 7/2025 (16 seer AC unit with 1 year maintenance and 10yr-parts/2yr-labor). Families are drawn to the area thanks to its top-rated schools, making this condo not just a home, but a gateway to a vibrant community. Recently refreshed and ready for its new owners to display their personal touches.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Bob Bretz, Pa (407-797-9500)
502 CLUB DR, WINTER SPRINGS, FL 32708
$219,50071 Days on yellowkey MLS ID: O6390697
REDUCED by $10,000 (4.4%) on 05/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1224 Built: 1987Monthly Fee: $520 Tax: $3,355 (2025)Community: Cypress ClubTownhouse
Taxes:$3,355
Remarks: Beautiful 2 bedroom, 2 bathroom townhome in Winter Springs, located in the sought-after Cypress Club at The Highlands community, known for its lush landscaping, fantastic amenities, and serene walking trails. Step inside to a spacious open floor plan with soaring vaulted ceilings and tile flooring throughout the main living areas. The living room features a cozy wood-burning fireplace, creating a warm and inviting focal point. The galley kitchen is fully equipped with all appliances, a glass tile backsplash, and a closet pantry for added storage. This home offers double suites, thoughtfully split between the two levels, each with its own private bathroom. The upstairs loft provides the perfect flex space for a home office, reading nook, or creative studio. Step out back to a lovely screened patio overlooking a private, park-like setting with no rear neighbors, creating a peaceful outdoor retreat. An exterior storage closet offers convenient space for bikes, tools, or gardening supplies. Recent updates include a full professional re-pipe (2026), new water heater (2025), new refrigerator (2024), new interior paint in modern greige tones (2023), and new carpet in bedrooms and stairs (2023). This townhome includes two reserved parking spaces, side-by-side, including one covered carport space. Cypress Club residents enjoy their own private community pool along with full access to The Highlands’ amenities, including a lap pool, tennis courts, playground, BBQ/picnic areas, and more. Ideally located with easy access to SR-434, 17-92, SR-417, and I-4, and zoned for top-rated Seminole County schools. Outdoor recreation and weekend adventure are just minutes away with convenient access to the Cross Seminole Trail and Central Winds Park, offering miles of scenic biking and walking paths, sports fields, and community events. Everyday conveniences are equally close by, with Winter Springs Town Center and other major shopping plazas just a short drive away, providing easy access to grocery stores, fitness centers, banks, restaurants, and all your daily essentials.
Listing is courtesy of: INFINITY REAL ESTATE GROUP (407-760-0835)
Listing Agent: Tamara Martin (407-760-0835)
165 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$384,99087 Days on yellowkey MLS ID: O6386473
1 Days Off yellowkey (back on 4/22/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1476 Built: 2026Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Taxes:$1,457
Remarks: Under Construction. As you step inside the Aurora, you are greeted by an inviting open-concept gathering room, seamlessly connecting the dining room and kitchen. The flowing layout creates an expansive and airy atmosphere, perfect for both entertaining guests and enjoying everyday life. The owner's suite is a true retreat, offering a sanctuary of relaxation and tranquility. The spacious bedroom is complemented by a large walk-in closet, providing plenty of storage for your wardrobe and personal items. With two additional bedrooms, this townhome provides flexibility for a growing family, a home office, or a guest room.
Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)
Listing Agent: Amanda Warren (321-662-0779)
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