Location: Winter Springs
Keyword(s): Indian Trails Middle
Keyword(s) Middle School: Indian Trails Middle
Do Not Show Listings
1379 TARFLOWER DR, WINTER SPRINGS, FL 32708
$485,00030 Days on yellowkey MLS ID: O6390913
0 Days Off yellowkey (back on 4/18/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1704 Built: 2024Monthly Fee: $356 Tax: $4,485 (2025)Community: Hickory GroveTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,485
Elementary School: Layer Elementary
High School: Winter Springs High
Tax Year: 2025
Middle School: Indian Trails Middle
Remarks: Under contract-accepting backup offers. RARE END UNIT MOVE IN READY townhome with the PRIMARY BEDROOM DOWNSTAIRS in the heart of the Winter Springs Town Center! This beautifully maintained 3-bedroom, 2.5-bath home features a screened porch, custom California Closets in the primary suite, a rear-entry 2-car garage, and a bright open floor plan just steps from the Cross Seminole Trail, community includes community pool and dog park. Welcome to 1379 Tarflower Drive, located in the desirable Hickory Grove community in the heart of Winter Springs Town Center. This end-unit townhome offers additional privacy, extra windows, and abundant natural light, creating a bright and inviting living space. The open-concept floor plan is ideal for modern living and entertaining, featuring a spacious kitchen with stainless steel appliances, ample cabinetry, a walk-in pantry, and a breakfast bar overlooking the dining and living areas. Just off the living space, the screened-in porch provides the perfect spot to enjoy quiet mornings or relaxing Florida evenings. One of the most desirable features of this home is the first-floor primary suite, offering convenience and privacy. The suite includes a custom California Closet system in the walk-in closet, providing exceptional storage and organization, along with a spacious en-suite bathroom. Upstairs, you’ll find two additional bedrooms and flexible living space, ideal for guests, a home office, or additional family living. Residents of Hickory Grove enjoy low-maintenance living and a charming neighborhood atmosphere located just steps from the Cross Seminole Trail, a nearly 23-mile scenic trail system popular for biking, jogging, and outdoor recreation. The home is located in the highly rated Seminole County Public School District, ranked #1 in Florida, and is conveniently close to Winter Springs High School. Winter Springs itself has earned national recognition as one of Central Florida’s most desirable communities and was ranked among Money Magazine’s Top 100 Best Places to Live in America. Known for its beautiful parks, scenic trails, community events, and strong sense of community, the city offers an exceptional quality of life. With convenient access to SR-434, SR-417, Lake Mary, Oviedo, and downtown Orlando, this location provides the perfect balance of suburban charm and commuter convenience. End units with first-floor primary suites in this location are rarely available—schedule your private showing today.
Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE (407-380-2800)
Listing Agent: Melanie Miller (407-745-8317)
1331 AUGUSTA NATIONAL BLVD, WINTER SPRINGS, FL 32708
$450,00037 Days on yellowkey MLS ID: O6389425
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1657 Built: 1988Monthly Fee: $125 Tax: $4,965 (2025)Community: Country Club Village Unit 3Single Family
Taxes:$4,965
Elementary School: Keeth Elementary
Remarks: **BRAND NEW tile barrel roof just installed** Welcome to easy-maintenance living in the highly desirable golf community of Tuscawilla/Winter Springs! This beautifully maintained 3-bedroom home PLUS office/den offers a bright open layout with vaulted ceilings, ceramic tile flooring, and abundant natural light throughout. The updated eat-in kitchen with breakfast bar and modern finishes flows seamlessly into the main living and dining spaces, while updated bathrooms, inside laundry room, and a 2-car garage with epoxy floors add everyday comfort and convenience. Both bathrooms have modern finishes and well-appointed upgrades; and plenty of storage throughout. Additional major updates include dual pane/energy-efficient windows, epoxy garage floors, attic with deck flooring, water filtration system(kitchen), NEW water heater (2024), Carrier HVAC (2016), and whole house re-piped. The flexible floor plan also includes a dedicated office/den, ideal for working from home, hobbies, or additional living space. Enjoy year-round comfort in the all-season enclosed patio with dedicated A/C, all overlooking a peaceful wooded lot that creates a private and relaxing setting. Additional features include paver driveway & patio, and low-maintenance appeal in one of Winter Springs’ most established and sought-after communities. Located near Tuscawilla Country Club offering golf, tennis, and an Olympic-sized pool, as well as parks, walking trails, shopping, dining, and top-rated Seminole County schools, this home offers the perfect blend of location, lifestyle, and smart updates. A rare opportunity to enjoy updated, easy living with a convenient Winter Springs location and zoned for top-rated Seminole County schools.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Allison Day (407-617-2881)
161 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$484,99045 Days on yellowkey MLS ID: O6386458
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1704 Built: 2026Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Taxes:$1,457
Remarks: Under Construction. A standout feature of this end-unit home is the owner’s suite, conveniently located on the first floor, providing privacy and ease of access. This inviting retreat includes abundant natural light, a generous walk-in closet, and a well-appointed private bath. The open-concept main floor features expansive living and dining areas that flow seamlessly into a thoughtfully designed kitchen—complete with stainless steel appliances, including a refrigerator, a walk-in pantry, and a spacious breakfast bar—ideal for entertaining or everyday living. Laundry room, complete with washer and dryer is conveniently located on the main floor. Upstairs, you’ll find two additional bedrooms, a versatile loft perfect for a home office or media space, along with ample storage and a dedicated laundry area. A rear-loading 2-car garage adds both functionality and curb appeal. Located in desirable Winter Springs near the vibrant Town Center, residents enjoy a highly sought-after lifestyle with walkable access to shopping, dining, and community events. Known for its top-rated schools, scenic parks, and extensive trail system, Winter Springs offers a perfect balance of small-town charm and modern convenience—just a short drive from Orlando. Discover low-maintenance townhome living in one of Central Florida’s most connected and livable communities.
Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)
Listing Agent: Amanda Warren (321-662-0779)
173 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$484,99045 Days on yellowkey MLS ID: O6386437
Remarks: Under Construction. With an open concept ground floor and spacious living areas, the Sofia is ideal for entertaining and everyday life. Dedicated as an end unit, this floorplan features 3 bedrooms, 2.5 bathrooms and a rear-loading 2-car garage. The 2nd floor features a loft, abundant storage, and laundry space. Located on the 1st floor, the owner's suite that has it all - a spacious walk-in closet, great natural light, and private bath. Stainless steel appliances, a walk-in pantry and a breakfast bar are all featured in this floorplan's thoughtfully designed kitchen.
165 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$384,99045 Days on yellowkey MLS ID: O6386473
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1476 Built: 2026Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
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.
1276 CRAB APPLE LN, WINTER SPRINGS, FL 32708
$381,99088 Days on yellowkey MLS ID: O6375116
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1476 Built: 2025Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Remarks: 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.
189 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$491,99099 Days on yellowkey MLS ID: O6372546
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1704 Built: 2025Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Remarks: Experience luxurious living in the Sofia floorplan, where the spotlight shines on the exquisite first-floor owner's suite that exudes sophistication with a spacious walk-in closet, abundant natural light, and a private bath. This end unit boasts an open-concept ground floor, perfect for entertaining and daily life. With 3 bedrooms, 2.5 bathrooms, and a rear-loading 2-car garage, this residence offers both style and functionality. Enjoy the convenience of first-floor laundry, while the 2nd floor features a loft and two generous-sized bedrooms. The thoughtfully designed kitchen showcases stainless steel appliances, a walk-in pantry, and a breakfast bar for a truly elevated living experience. Located in desirable Winter Springs near the vibrant Town Center, residents enjoy a highly sought-after lifestyle with walkable access to shopping, dining, and community events. Known for its top-rated schools, scenic parks, and extensive trail system, Winter Springs offers a perfect balance of small-town charm and modern convenience—just a short drive from Orlando. Discover low-maintenance townhome living in one of Central Florida’s most connected and livable communities.
1272 CRAB APPLE LN, WINTER SPRINGS, FL 32708
$397,99099 Days on yellowkey MLS ID: O6371853
0 Days Off yellowkey (back on 4/12/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1678 Built: 2025Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Remarks: The Catalina I is a harmonious blend of style, functionality, and comfort, offering a lifestyle that caters to your every need. As you step inside you are greeted by an open-concept design that seamlessly integrates the gathering room, dining room, and kitchen, creating an inviting space for both everyday living and entertaining. This townhome features 3 bedrooms, providing flexible living options for families, professionals, or those in need of a dedicated home office space. The loft adds an additional dimension, allowing you to customize this versatile area to suit your lifestyle.
1128 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708
$489,00016 Days on yellowkey MLS ID: O6395600
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2344 Built: 2021Monthly Fee: $236 Tax: $2,985 (2025)Community: Seminole Crossing TwnhmsTownhouse
Taxes:$2,985
Remarks: One or more photo(s) has been virtually staged. Welcome to an exceptional opportunity in the heart of Winter Springs, where lifestyle, location and luxury converge at 1128 Spotted Sandpiper Loop. Positioned in a thoughtfully planned community, this residence offers the ideal balance of elegance and everyday convenience. From moment you arrive, you are embraced by a neighborhood designed for connection and ease, tree-lined streets, inviting trails and a sense of community that makes this address desirable. Ideally just moments from Winter Springs Town Center, this residence offers an accessible lifestyle. Natural light fills the interiors, creating a warm and welcoming ambiance suited for relaxed living and stylish entertaining. Thoughtfully designed across three levels, the first floor offers a private retreat ideal for guests, complete with its own en suite. The second level unfolds into the heart of the home, featuring an open concept living space with a well-appointed kitchen, dining area and inviting family room. The third floor is dedicated to restful living, showcasing three bedrooms, two full baths and a convenient laundry area. Updates include new carpeting throughout with transferable warranty and fresh interior paint reflecting the home's meticulous maintenance. Beyond your doorstep, accessibility becomes a defining feature of this lifestyle. Enjoy proximity to local shops, dining, parks and top-rated Seminole County schools, all just moments away. With easy access to major roadways, commuting to downtown Orlando, nearby business hubs, or weekend destinations is simple and efficient. Amenities include community pool, trails and accessibility to area favorites.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Jackie Hughes (407-247-0030)
214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708
$649,90056 Days on yellowkey MLS ID: O6372400
REDUCED by $25,100 (3.7%) on 04/15/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2474 Built: 2001Monthly Fee: $42 Tax: $5,539 (2024)Community: Chestnut RidgeSingle Family
Taxes:$5,539
Elementary School: Rainbow Elementary
Tax Year: 2024
Remarks: Owner is Motivated! Exceptionally amazing price for a GOLF FRONT LIFESTYLE that sits DIRECTLY on the 16th hole of the Tuscawilla Golf Course! Welcome home to 214 Chestnut Ridge, a custom-built single-family residence that 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. 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. Location is paramount, with proximity to quality schools, shopping, dining, and major employment hubs. This property, fronting the 16th hole of the Tuscawilla Country Club, is not just a home—it's a lifestyle waiting for you at Chestnut Ridge. HIGHLIGHTED EXTRA. 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 MUST SEE!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Laurie Cain (407-484-9944)
118 BROOKSHIRE CT, WINTER SPRINGS, FL 32708
$599,0002 Days on yellowkey MLS ID: O6394521
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2100 Built: 1996Monthly Fee: $48 Tax: $3,067 (2024)Community: Winding Hollow Unit 1Single Family
Taxes:$3,067
Remarks: Welcome to this immaculate pool home located in the highly desirable Winding Hollow community of Winter Springs! Nestled on a quiet cul-de-sac with no rear neighbors, this home sits on an oversized, private lot—creating the perfect backyard retreat. Surrounded by mature landscaping and set within a peaceful neighborhood, this property makes a lasting impression from the moment you arrive. This home has been meticulously renovated with thoughtful attention to detail throughout. Step inside to discover brand-new tile flooring (2022) that flows seamlessly throughout the home. The spacious foyer offers the perfect place to drop off your belongings at the end of the day. To the right of the entry, you’ll find a versatile fourth bedroom—ideal as a home office, flex space, or guest room. The airy dining room provides an ideal setting for hosting dinner parties, while the beautifully renovated kitchen (2022) features granite countertops, upgraded cabinetry, under cabinet lighting, and new stainless steel appliances. The new kitchen is truly the heart of the home—whether you're a seasoned chef or just love to cook, this kitchen delivers. Overlooking the family room, the kitchen also includes a breakfast bar and cozy breakfast nook with views of the pool. The expansive family room showcases soaring ceilings and abundant natural light, creating a warm and inviting space to unwind while enjoying views of your private backyard oasis. The well-designed layout offers both functionality and an inviting atmosphere, perfect for everyday living and entertaining. The generous primary suite offers tranquil pool views and features a newly renovated ensuite bathroom (2023) complete with dual sinks, a jacuzzi tub, separate shower, and a spacious walk-in closet. The split floor plan provides added privacy, with additional bedrooms and a bright, updated full bathroom—ideal for family or guests. Step outside to your sparkling pool with fountains—perfect for relaxing or entertaining year-round. Enjoy the expansive, lush backyard—an oversized green space that offers endless possibilities for outdoor living. Recent upgrades include brand new energy-efficient Pella doors and windows (2019), new flooring (2022), a fully renovated kitchen (2022), updated appliances (2022), a renovated primary bathroom (2023), a new hot water heater (2023), re-screened lanai (2020), pool resurfaced (2023) and a new fence (2017). Ideally located in one of Seminole County’s most sought-after communities, this home is just minutes from top-rated schools, the Winter Springs Town Center, premier shopping and dining, with convenient access to I-4 and State Road 417. Outdoor enthusiasts will love being close to Central Winds Park, complete with sports fields, the AdventHealth pickleball complex, with restrooms, a dog park, and the Seminole Trail. Call for your showing today!
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Katie Bray (407-779-6677)
1275 MARLEY LN, WINTER SPRINGS, FL 32708
$355,00031 Days on yellowkey MLS ID: O6391943
REDUCED by $5,000 (1.4%) on 04/13/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1425 Built: 2015Monthly Fee: $233 Tax: $2,895 (2025)Community: Jesups LandingTownhouse
Taxes:$2,895
Remarks: Welcome to Jesup’s Landing, where style, convenience, and community come together in the heart of Winter Springs—one of Central Florida’s most charming and sought-after towns. This beautifully maintained two-story townhome offers peaceful Seminole Trail views and a lifestyle that feels both relaxed and connected. Inside, the open layout is designed for real life and effortless entertaining. The kitchen steals the show with granite countertops, stunning 42” cabinets with crown molding, an extended double sink, pull-out garbage, and a huge pantry—all flowing seamlessly into the main living space. Upgrades like the Taexx built-in pest control system and keypad garage entry add ease and peace of mind. The best part is this home has a brand new roof! Upstairs, the primary suite feels elevated with a 10-foot vaulted ceiling, spacious walk-in closet, and en-suite bath with dual sinks. Step outside and take in serene Seminole Trail views—perfect for morning walks, bike rides, or unwinding at sunset. Residents enjoy access to a community pool and clubhouse, all just minutes from everything that matters. The location is a standout—close to UCF, Research Park, Lockheed Martin, Siemens, with quick access to the beltway for an easy commute to downtown Orlando, area airports, and beyond. Plus, you’re moments from Central Winds Park, top-rated trails, shopping, dining, and the Winter Springs Town Center. Homes in Jesup’s Landing don’t last—especially ones like this. Come see it before someone else does.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: David Weiss (407-765-9020)
1815 SENECA BLVD, WINTER SPRINGS, FL 32708
$1,039,000121 Days on yellowkey MLS ID: O6368232
REDUCED by $10,000 (1.0%) on 04/15/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3885 Built: 1989 Tax: $5,558 (2024)Community: Tuscawilla Unit 14BSpa: YesSingle Family
Taxes:$5,558
Elementary School: Lawton Elementary
High School: Oviedo High
Remarks: This stunning 5-bedroom pool home in the highly desirable Chelsea Woods at Tuscawilla has been completely remodeled from top to bottom. The home offers exceptional living space, including a large living room with fireplace, a spacious family room with fireplace, and a formal dining room—ideal for entertaining. A large bonus room provides flexible space for a home office, playroom, or additional living area. The brand-new kitchen is a showstopper, featuring new appliances, quartz countertops, two-tone cabinetry with open shelving, and a stylish bar area with additional shelving. The large laundry room includes a convenient butler’s pantry area, adding extra storage and functionality. Downstairs, you’ll also find two half bathrooms, all beautifully updated. All five bedrooms are located upstairs, along with three fully renovated bathrooms, including a Jack-and-Jill bath. The expansive primary suite offers a true retreat with a luxurious soaking tub, large walk-in shower, and generous space throughout. Recent upgrades also include new wood-look tile plank flooring throughout the lower level, LVP flooring upstairs, ROOF (2023), and both A/C units replaced. Step outside to enjoy the covered, screened patio overlooking the pool—perfect for relaxing or entertaining. Located in Tuscawilla, this home is zoned for top-rated schools and offers the space, updates, and location you’ve been looking for. Schedule your private showing today!
Listing Agent: Belinda Gonzales (321-277-8994)
1165 ORANGE AVE, WINTER SPRINGS, FL 32708
$400,0002 Days on yellowkey MLS ID: O6398101
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2094 Built: 2015Monthly Fee: $233 Tax: $4,666 (2025)Community: Jesups LandingSpa: NoTownhouse
Taxes:$4,666
Remarks: Welcome to this stunning, modern end-unit townhome located in the highly sought-after community of Jesup’s Landing in Winter Springs. This beautifully designed 3 bedroom, 3.5 bathroom residence with a spacious 2-car garage offers an exceptional blend of comfort, style, and convenience, making it the perfect choice for buyers seeking luxury townhome living in a prime location. From the moment you arrive, you’ll appreciate the added privacy and natural light that comes with being an end unit, along with the home’s contemporary design and thoughtful layout. The first floor features a full suite that is ideal as a secluded primary bedroom, for guests, multigenerational living, or a home office. This space is complete with elegant granite countertops, a large walk-in shower, and direct access to a private balcony, creating a peaceful retreat. You’ll also find a convenient drop station and easy access to the attached garage, adding functionality to everyday living. As you move to the second level, you’re welcomed into an expansive open-concept living area designed for both entertaining and relaxation. The gourmet kitchen is a true centerpiece, featuring sleek granite countertops, a large center island for gathering, and ample cabinetry for storage. The adjoining dining area flows seamlessly into a spacious living room filled with natural light, while a half bath and two separate private balconies enhance the indoor-outdoor living experience. This level is perfect for hosting guests or enjoying quiet evenings at home. The third floor offers even more versatility with a generous loft area that can serve as a media room, office space, or bonus family room. Two well-appointed bedrooms, each with access to full bathrooms, provide comfort and privacy for family members or guests. Throughout the home, you’ll notice numerous upgrades, meticulous maintenance, and modern finishes that elevate the overall living experience. Residents of Jesup’s Landing enjoy resort-style amenities including a sparkling community pool, a fully equipped fitness center, and a stylish billiards lounge. Outdoor enthusiasts will love the direct access to the Seminole Cross Trail, ideal for biking, jogging, and enjoying Florida’s natural beauty. The home is also centrally situated close to popular restaurants, shopping destinations, entertainment options, and Central Winds Park. Located in top-rated Seminole County school zones and offering convenient access to major highways, this property combines luxury, location, and lifestyle. This move-in ready townhome is a rare opportunity to own a modern, spacious property in one of Winter Springs’ most desirable communities. Don’t miss your chance to experience the best of Florida living in Jesup’s Landing.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Thomas Mcnamara, Jr (407-754-6412)
1513 BLACK BEAR CT, WINTER SPRINGS, FL 32708
$1,479,50044 Days on yellowkey MLS ID: O6385058
REDUCED by $69,500 (4.5%) on 04/16/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 6175 Built: 1989Monthly Fee: $142 Tax: $23,523 (2025)Community: Bear Creek EstatesSingle Family
Taxes:$23,523
Remarks: Welcome to this exceptional home in the exclusive gated community of Bear Creek Estates, set on over an acre of lush wooded greenbelt with beautiful landscaping and a circular driveway that creates outstanding curb appeal. The over 6,000 sq. ft. (includes 1 car garage/hobby room of approx. 280 sq.ft.) home features a new architectural tile roof (less than one year old) and 10-foot ceilings throughout the first floor, creating a bright and spacious feel. Inside, you’ll find elegant formal living and dining spaces, a private home office, and a comfortable family room overlooking the sparkling pool and lanai. The home offers oversized secondary bedrooms with seating areas, plus a large additional bedroom that can serve as an office, art studio or flex space. Entertainment is exceptional with two theater spaces, The main floor home theater is projector-ready, with acoustic panels, granite snack counter, an electronic masking screen and wiring for 7.1 sound. The upstairs primary bedroom is massive in size and the ideal retreat to unwind at end of the day! Complete with its sitting area and outdoor deck with stunning panoramic views of lush nature. The upstairs primary suite in this home also includes a projector drop-down screen and wiring for 5.1 sound. The private backyard retreat features a beautiful pool with LED lighting, waterfall feature, and updated pump and filter (2023), along with panoramic views of lush green space. Additional highlights include a smart audio system controlled by smartphone app, extensive network wiring, pre-wiring for security cameras, well-fed irrigation, and a backyard telescope pier with power and ethernet. In Winter Springs, this home offers peaceful luxury living while being close to shopping, dining and major commuting routes.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Lynda Miller (407-620-2924)
600 NORTHERN WAY #906, WINTER SPRINGS, FL 32708
$299,99979 Days on yellowkey MLS ID: O6375918
REDUCED by $10,001 (3.2%) on 04/01/2026
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 and ready for immediate move-in. Located in the latest and greatest phase of Tuscany Place, which was built in 2016. Exceptional open floor plan at over 1,600 square feet truly sets this home apart as does the flexibility for multi-generation living. All bedroom suites have their very own en-suite bathroom—one of the bedrooms with full bath is on the ground level—so it’s perfect for a mother-in-law suite. Large sized rooms, updated bathrooms, and all the features you are looking for. The kitchen has stainless steel appliances, granite countertops, a large pantry, and a breakfast bar for dining. See yourself entertaining easily in the large living room - family room combination and then stepping through glass sliding doors out to the patio. Additional conveniences include a dedicated laundry room with shelves, walk-in closets, ceiling fans, and modern fixtures throughout the home. Roof replaced in March 2026. Hvac 2020. Water heater 2017. Low monthly fee covers access to the community pool, exterior maintenance and landscaping, sewer, and trash services. Excellent location and zoned for Seminole County Public Schools and many private schools nearby. Very close to all the shopping and restaurants at Winter Springs Town Center or along Tuskawilla and Red Bug Lake Rd, and Trotwood Park is right at your doorstep. Needless to say, you don't want to miss out on this outstanding property. Note: A line of credit may be sufficient to purchase this property and please contact Isabelle Martinez Paramount Residential Mortgage Group for more info. All sold as-is and with the right to inspect. Contact our office today to schedule a private tour!
Listing is courtesy of: JR REALTY GROUP LLC (407-920-4624)
Listing Agent: John Vincent (407-534-9764)
30 S EDGEMON AVE, WINTER SPRINGS, FL 32708
$250,00017 Days on yellowkey MLS ID: O6394469
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1545 Built: 1960 Tax: $318 (2024)Community: North Orlando 2Nd AddSingle Family
Taxes:$318
Elementary School: Winter Springs Elementary
Remarks: Under contract-accepting backup offers. One owner Vintage home. 66 years old. VIEW SHORT VIRTUAL TOUR! So much potential. Needs full remodel but a nice piece of land with lots of living options. NO HOA with an amazing location. Multifamily Multi-generational potential. Was added onto many years ago. Originally built as a 2/1. Had another room with a second bath many years ago. Fireplace and family room was added on years ago. Also has a screened porch added onto the back. No idea how many square feet the home actually is. Electrical has been updated Natural Gas for you, even the HWH is gas. Several sheds on property. roof is 2018, A/C 2011. Owner has moved out of state so looking for a sale. Winter Springs has AMAZING Seminole County A+ rated Schools. Worth a look if you need some space in a great area. Someone has lived in this home for many years. Buy it and remodel down the road. Starter home for the right family. Live in it while you remodel. Won't last.
226 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708
$824,9001 Day on yellowkey MLS ID: O6398877
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2902 Built: 1994Monthly Fee: $44 Tax: $4,461 (2024)Community: Chestnut RidgeSpa: NoSingle Family
Taxes:$4,461
Remarks: Showcase two story gem in the heart of Tuscawilla! Come see the abundant high-end upgrades including a professionally designed chefs’ kitchen with all the bells and whistles! This 4 bedroom pool home with private study and upstairs bonus room features a recently renovated screened pool and is located on a quiet tree lined street in a sought after neighborhood. Your tour begins via newly painted leaded glass doors with a giant Palladian window above. You will be welcomed by a grand two story foyer and an artful staircase with hardwood steps and handsome millwork including 10” crown molding. Flanking the foyer, area an elegant dining space and handsome study with newly installed French doors. The recently renovated designer kitchen features custom cabinetry with double upper cabinets reaching all the way to the ceiling! You will love the quartz topped custom dining/ chef’s island, quartz counter tops, glass tile backsplash, large hidden walk-in pantry with cabinet door front, excellent upgraded appliances, and a dedicated prep sink. Two under-cabinet “Uline” beverage refrigerators add a touch of luxury and convenience. French doors in the kitchen dinette lead you to the covered patio and pool area. Because the kitchen is open to the family room, you stay connected to guests and family relaxing in the huge family room that features a soaring two story ceiling, 8’ tall sliding doors to the back patio, a huge glass transom window above and a stunning woodburning fireplace welcoming you to the heart of the home. From here, your eyes are drawn straight out the glass doors to the newly refurbished, sparkling pool, and lush backyard. The primary suite is located on the first floor and is adorned with upgraded wood flooring, plantation shutters and ample room for a dedicated sitting area. Fresh, neutral finishes and a huge travertine shower give a classic elegance to the primary bath and the updated custom closet is absolutely stunning. The second story features three additional bedrooms (two of them are 15x13) and a large loft/bonus room with storage closet (easily converted to a 5th bedroom) Now, enjoy the outside! The spacious covered lanai and renovated screened solar heated pool invite you to morning coffee, evening dinners, or weekend pool parties. The backyard is spacious and welcomes your little ones to play and pets to run freely. With the pool fully resurfaced, retiled, and upgraded with a cool-touch deck and new filter (with warranty), you can enjoy Florida living at its finest. This home is packed with meaningful upgrades: termite bond with Massey, whole-home repipe (2014), newer water heater (2020), two A/C units (2023 & 2014), new garage door opener, fiber internet with AT&T, new office French doors (2020), hardwood floors, unique terrazzo tile, Crown Molding, Closets by Design systems, new landscaping, fresh interior paint, and more. All appliances are included including the washer and dryer. Yes, you can have all of this: A gorgeous move in ready executive pool home in the highly desirable community of Tuscawilla known for its charm and convenience, a lifestyle that’s hard to beat!
Listing Agent: Colleen Kahl (407-630-0027)
276 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$290,0001 Day on yellowkey MLS ID: O6399623
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1089 Built: 1994Monthly Fee: $127 Tax: $3,719 (2025)Community: Deersong 2Single Family
Taxes:$3,719
Remarks: Don't Wait!! Seller offers $5,000 Towards buyer's closing costs. This 3-bedroom, 2-bathroom home in Deersong-2 is a fantastic opportunity for anyone looking for a move-in-ready property in Winter Springs. With its newly updated kitchen, Modern faucet, granite countertops, and indoor laundry. High living room ceilings, the home feels both modern and spacious. The community offers excellent amenities, including a gated pool and tennis courts, all for a low HOA fee. Its prime location near top-rated Seminole County schools and the popular Torcaso Cove park makes it ideal for daily living. will not last long, Schedule your private showing today!!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Mariam Sherkawy (407-272-4234)
684 OLEAN CT, WINTER SPRINGS, FL 32708
$849,9001 Day on yellowkey MLS ID: O6399510
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2832 Built: 1988Monthly Fee: $8 Tax: $8,448 (2025)Community: Chelsea WoodsSpa: NoSingle Family
Taxes:$8,448
Remarks: Walk on it and call it home! This amazingly cared for POOL home with 3 Car Garage in Chelsea Woods, Tuscawilla is ready for its new owner! With nearly 3,000 square feet, this spacious 5-bedroom, 4-bathroom home sits on over one-third of an acre and offers the perfect blend of comfort, functionality, and Florida living. As you step inside, you’re greeted by an open and inviting family room with stunning views of the pool, seamlessly connected to the dining area. A bonus: the pool table stays and can double as a dining table for entertaining! To the left of the entry, you’ll find a generously sized primary suite along with an additional bedroom and full bathroom—ideal for guests or a home office setup. The heart of the home is the expansive kitchen, featuring ample space, a cozy kitchenette, and a wet bar—perfect for hosting. The adjoining living room showcases a beautiful fireplace, adding warmth and charm to the space. As you will notice, this home is very LIGHT AND BRIGHT and features NO CARPET! Toward the back of the home are three additional bedrooms and two full bathrooms, including one with a private ensuite—perfect for multi-generational living or added privacy. Step outside to your fully fenced backyard oasis, complete with a screened-in, heated saltwater pool and lanai—ideal for year-round enjoyment. Major updates include a NEW ROOF (2023) and newer AC units (2023 & 2016), offering peace of mind for years to come. Located in the sought-after Tuscawilla area, Chelsea Woods offers optional HOA and convenient access to top-rated schools, Tuscawilla Country Club, SR-417, Seminole Trail, Seminole State College, UCF, Lockheed Martin, and Siemens. This exceptional home won’t last long—schedule your private showing today before this home is SOLD!
Listing is courtesy of: VOSS REALTY INC (407-456-0777)
Listing Agent: Lindsay Kaye Voss (407-456-0777)
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