Location: Winter Springs
Do Not Show Listings
1421 HAPPY BIRD LN, WINTER SPRINGS, FL 32708
$563,408198 Days on yellowkey MLS ID: O6359884
REDUCED by $10,040 (1.8%) on 05/28/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2502 Built: 2019Monthly Fee: $130 Tax: $4,781 (2024)Community: Tuskawilla Crossings 34'SSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,781
Elementary School: Layer Elementary
High School: Winter Springs High
Tax Year: 2024
Middle School: Indian Trails Middle
Remarks: Welcome home! Fall in love this welcoming two-story home that features 4 bedrooms and 3.5 bathrooms, perfectly positioned across from the Cross Seminole Trail. Start your day with a cup of coffee on the charming covered front porch, where you can take in the refreshing breeze and picturesque views of the 13-mile trail that winds through Seminole County and connects to other scenic trails. Step inside to discover an inviting open floor plan enhanced by beautiful wood-style tile flooring. Prepare your favorite meals in the gourmet kitchen with stainless steel appliances, pantry, modern fixtures, and breakfast bar ideal for casual dining. The open-concept living and dining areas create the perfect setting for effortless entertaining. The primary suite, conveniently located on the first floor, includes a walk-in closet and a private ensuite bathroom with dual sinks and a walk-in shower. Ascend to versatile loft area upstairs offering additional space for work, play, or relaxation. You will also appreciate the secondary primary suite on this level, complete with a walk-in closet, dual sinks, and shower. Additionally, two generously sized bedrooms await your use along with a full bathroom. Outside, unwind on the covered back patio, surrounded by vinyl fencing for added privacy. A rear-facing two-car garage with a paver driveway completes the property. This home is part of the Tuskawilla Crossing community, which includes a dog park, a sparkling community pool for leisurely fun, and a playground. The area is rich in dining and shopping options and provides easy access to the 417. Situated in Seminole County which is well known for its public school system. Don’t miss the chance to make this exceptional home yours—schedule a showing today!
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: Brent Dehoop (407-448-8971)
622 ANHINGA RD, WINTER SPRINGS, FL 32708
$384,900156 Days on yellowkey MLS ID: O6369225
REDUCED by $13,600 (3.4%) on 05/18/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1721 Built: 1988Monthly Fee: $106 Tax: $4,083 (2024)Community: GreenspointeSingle Family
Taxes:$4,083
Elementary School: Highlands Elementary
Middle School: South Seminole Middle
Remarks: NEW ROOF 2026, HVAC 2017–2018, and water heater 2022, giving buyers peace of mind from day one. This 3-bedroom, 2.5-bathroom home offers over 1,700 sqft of living space in a top-rated Seminole County school zone. The layout is highly desirable with the primary bedroom downstairs, featuring a spacious walk-in closet and a large private bathroom with dual vanities, separate shower, soaking tub, and private toilet space. The home offers a bright and open layout with high ceilings and tile flooring throughout the main living areas. The kitchen includes granite countertops, stainless steel appliances, light cabinetry, and a breakfast bar, with sliding glass doors leading to a cute shaded backyard — perfect to relax or entertain. Upstairs you’ll find a spacious loft along with two additional bedrooms and a full bathroom, offering flexibility for guests, family, or working from home. Additional features include a 2-car garage, interior laundry room, neutral finishes throughout, and the home is vacant and easy to show. Ideally located near UCF, Valencia College, SR-417, SR-434, and I-4, with easy access to shopping, dining, Downtown Orlando, and Central Florida beaches.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
109 CHERRY CREEK CIR, WINTER SPRINGS, FL 32708
$1,090,00024 Days on yellowkey MLS ID: O6404923
REDUCED by $60,000 (5.2%) on 05/28/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3440 Built: 1996Monthly Fee: $123 Tax: $7,388 (2024)Community: Reserve At Tuscawilla Ph 1 TheSpa: YesSingle Family
Taxes:$7,388
Elementary School: Keeth Elementary
Remarks: Tucked behind the gates of The Reserve at Tuscawilla, this estate unfolds in a way that feels both grounded and quietly impressive, offering a sense of space, privacy, and ease that is increasingly rare to find. Set on over half an acre, 109 Cherry Creek Circle invites you to settle into a lifestyle where everyday living flows effortlessly into moments worth celebrating. From the moment you arrive, there is a feeling of arrival that stays with you. Mature landscaping, a side-entry three-car garage, and the understated presence of a custom Von Jacobs-built home set the tone. Inside, natural light filters through high ceilings and classic architectural details, guiding you through a layout designed for both connection and retreat. The main living areas feel open yet intimate, centered around a warm gas fireplace and views that draw your attention immediately to what makes this home so special. The backyard is not simply an amenity. It is the heart of the experience. Designed for gathering, the outdoor living space offers multiple destinations to relax, entertain, and unwind. A deep resort-style pool and spa invite long afternoons in the sun, while Tennessee River Rock accents, a dedicated fire pit lounge, and an expansive lanai create layers of texture and ambiance. Evenings here feel effortless, whether hosting friends around the summer kitchen with its Viking grill and Texas smoker or enjoying a quiet night under the stars. It is a setting that naturally becomes part of your daily rhythm. Inside, the kitchen remains connected to it all, with a layout that keeps conversations going from room to room. A gas cooktop, double ovens, and a thoughtfully designed breakfast nook provide a space that is both functional and welcoming. Formal living and dining rooms offer flexibility, whether gathering for holidays or creating a more intimate setting for guests. The primary suite is privately positioned on the first floor, offering a calm and comfortable retreat at the end of the day. Its recently remodeled bath brings a fresh, spa-like feel while honoring the home’s timeless character. Additional bedrooms on the main level are thoughtfully arranged, while an expansive upstairs suite provides flexibility for guests, multigenerational living, or a private office and lounge. There is a sense throughout the home that it has been well cared for and intentionally updated where it matters most. Major improvements including the roof (2017), HVAC (2017), whole-house replumbing (2024), and water heater (2025) allow the next owner to step in with confidence, while leaving room to personalize over time in a way that reflects their own style. Beyond the home itself, life in The Reserve at Tuscawilla offers a lifestyle many seek and few find. Quiet, tree-lined streets, a gated setting, and a strong sense of community create an environment that feels both secure and welcoming. Just moments away, Tuscawilla Country Club becomes an extension of home, with golf, tennis, dining, and social events that bring neighbors together. Nearby trails, top-rated schools, and convenient access to major roadways complete the picture of daily ease. This home represents a rare opportunity to own within one of Winter Springs’ most established and desirable communities. It is a place that feels lived in, loved, and ready for its next chapter, where the value is not only in the features, but in the life it quietly supports.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Kara Lushear (321-663-5550)
820 WAKULLA LN, WINTER SPRINGS, FL 32708
$419,90022 Days on yellowkey MLS ID: TB8504175
REDUCED by $5,000 (1.2%) on 05/28/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1658 Built: 2012Monthly Fee: $167 Tax: $5,649 (2025)Community: Winter Spgs Village Ph 1Single Family
Taxes:$5,649
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Move-in ready and thoughtfully updated, this 3-bedroom, 2-bath home offers bright, comfortable living with fresh interior paint, new carpet, and new light fixtures throughout. The open main living area flows easily into the kitchen, where new quartz countertops, a new range, microwave, and dishwasher add style and everyday functionality. A new roof provides valuable peace of mind, while the spacious bedrooms, inviting natural light, and practical layout create a home that feels both polished and livable. With tasteful updates already complete, this home is ready to welcome its next owner.
Listing is courtesy of: OFFERPAD BROKERAGE FL, LLC (813-534-6326)
Listing Agent: Rob Jones (844-448-0749)
1825 SENECA BLVD, WINTER SPRINGS, FL 32708
$650,00052 Days on yellowkey MLS ID: O6396955
REDUCED by $25,000 (3.7%) on 05/28/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2711 Built: 1989Monthly Fee: $8 Tax: $1,171 (2025)Community: Tuscawilla Unit 14BSpa: NoSingle Family
Taxes:$1,171
Elementary School: Lawton Elementary
High School: Oviedo High
Remarks: One or more photo(s) has been virtually staged. ***MARCH 2026 Appraisal at $735,000***Welcome to 1825 Seneca Blvd in the heart of Tuskawilla, a rare opportunity to own a spacious one-story pool home on an almost half-acre lot in one of Seminole County’s most sought-after locations. Owned by the same family for 37 years, this 4-bedroom, 3 full bathroom block home offers 2,711 square feet of living space, a 2-car garage, soaring ceilings, skylights, abundant natural light, and an ideal layout with multiple living areas all on one level. Priced at its March 2026 appraised value of $735,000, this is a chance to secure a prime piece of real estate in a location where long-term ownership is the norm and opportunities like this do not come up often. Inside, the home offers impressive volume and flexibility. The main living room feels bright and open thanks to soaring ceilings and skylights, while the wood-burning fireplace adds warmth and character. The floor plan offers a great everyday flow with separate living and family spaces, formal and casual dining areas, and a split-bedroom style layout that gives the home both functionality and privacy. The home is move-in ready as it sits, but also presents an excellent opportunity for a new owner to update the cosmetics over time and make it their own. One of the standout features here is the outdoor space. The screened pool and patio area spans much of the rear of the home, creating a true extension of the living space and an ideal setup for relaxing or entertaining. The oversized lot is a major value driver, and because of the mature trees and natural setting, the property feels even more private than many homes nearby. It is the kind of yard that offers both space and seclusion, which is becoming harder and harder to find in this area. Major updates include a roof installed in June 2008, AC replaced in 2011, and water heater replaced in 2011. Optional HOA is another bonus. Zoned for Lawton Elementary, Indian Trails Middle, and Oviedo High School, this home is also close to Oviedo Mall, Trotwood Park, Tuskawilla Country Club, shopping, dining, and recreational amenities. If you have been searching for a well-maintained home with great bones, a large private lot, a screened pool, soaring ceilings, and an unbeatable Seminole County location, 1825 Seneca Blvd deserves your attention.
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Chris Creegan (407-622-1111)
907 GLEN ABBEY CIR, WINTER SPRINGS, FL 32708
$420,0002 Days on yellowkey MLS ID: O6411321
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1791 Built: 1997Monthly Fee: $126 Tax: $2,093 (2025)Community: Greenbriar Sub Ph 2Single Family
Taxes:$2,093
Remarks: Welcome home to this beautiful, move-in-ready residence nestled in the highly sought-after Greenbriar at Tuscawilla community! This charming 3-bedroom, 2-bath home offers a highly functional single-story layout with an open floor plan and split-bedroom design, creating both comfortable everyday living and added privacy. The spacious living and dining areas feature vaulted ceilings and abundant natural light, making the home feel bright and inviting. The oversized primary suite offers a relaxing retreat complete with a large walk-in closet and private bath. Enjoy low-maintenance living with a low HOA that includes lawn maintenance, plus access to the community pool. As an added option, Tuscawilla Country Club offers dining, fitness facilities, a junior Olympic pool, tennis courts and leagues, pickleball, golf, and social events. Conveniently located near SR 417, SR 434, and Red Bug Lake Road, you'll have easy access to shopping, dining, and entertainment. Don’t miss your opportunity to own this sweet home in one of Winter Springs’ most desirable communities. Schedule your private showing today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Jennifer Draper (321-439-7204)
448 MACGREGOR RD, WINTER SPRINGS, FL 32708
$350,00051 Days on yellowkey MLS ID: O6397231
REDUCED by $10,000 (2.8%) on 05/27/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1477 Built: 1993Monthly Fee: $6 Tax: $1,141 (2024)Community: Highland Village 2Spa: NoSingle Family
Taxes:$1,141
Remarks: Explore 448 MacGregor Rd, a individual residence with a straightforward design and integrated features. The interior includes a fireplace, and the primary bedroom features a walk in closet; the primary bathroom provides double sinks and a Jacuzzi. The exterior includes a covered patio and a fenced in backyard, providing an enclosed outdoor area. This property contains practical elements for daily living. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
1160 CITRUS OAKS RUN, WINTER SPRINGS, FL 32708
$850,00011 Days on yellowkey MLS ID: O6408959
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3118 Built: 2001Monthly Fee: $127 Tax: $8,339 (2025)Community: Citrus OaksSingle Family
Taxes:$8,339
Elementary School: Rainbow Elementary
Remarks: Exceptional luxury living awaits in this beautifully reimagined 5-bedroom, 3.5-bath residence located within an exclusive gated community. Offering over 3,100 square feet of refined living space, this impressive home showcases luxury finishes and thoughtful upgrades throughout, including elegant travertine flooring, rich oil-rubbed plank floors, and a stunning updated kitchen appointed with stainless steel appliances. Designed for both elevated entertaining and everyday comfort, the spacious interior flows seamlessly to a private screen-enclosed pool retreat featuring a resurfaced finish, travertine pavers, and a fully fenced backyard oasis. The luxurious primary and guest baths have been tastefully updated, while major improvements such as a 2019 roof, hurricane impact slider doors, and fresh exterior paint provide peace of mind and timeless appeal. Perfectly positioned near top-rated schools, upscale shopping, dining, and convenient 417 access, this exceptional residence delivers the ideal blend of luxury, comfort, and location.
Listing is courtesy of: JULIAN PROPERTIES, INC. (407-291-4900)
Listing Agent: Bo Julian (407-694-5843)
1385 SAN DIEGO CT, WINTER SPRINGS, FL 32708
$349,00050 Days on yellowkey MLS ID: O6397680
REDUCED by $8,500 (2.4%) on 05/06/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1518 Built: 1983Monthly Fee: $29 Tax: $1,540 (2024)Community: Sunrise Village Unit 1Spa: NoSingle Family
Taxes:$1,540
Remarks: SUNRISE VILLAGE 2/2 UPDATED HOME! PLUS A BONUS ROOM PERFECT FOR OFFICE, NURSERY, PLAYROOM, HOBBY ROOM, FLORIDA ROOM OR JUST ADDITIONAL LIVING SPACE! OPEN FLOOR PLAN! KITCHEN FEATURES TILE FLOORS, EAT IN KITCHEN AND LIGHT WOOD CABINETRY! ROOF 2022, A/C 2023, WATER HEATER 2025! MAIN BATH UPDATED WITH DECORATIVE TILE, GRANITE COUNTER, TILE FLOOR! DOUBLE PANED WINDOWS! WIDE BLINDS! KNOCKDOWN CEILINGS! NO CARPETING THRU OUT! LARGE SCREENED PATIO WITH TILE FLOOR! LOTS OF NATURAL LIGHT! FANS! LAUNDRY IN GARAGE! GREAT LOCATION, HIGHLY RATED SCHOOLS, LOW HOA DUES ($345 YEAR), COMMUNITY BASKETBALL, TENNIS AND PLAYGROUND!. CONVENIENT TO ALL AREAS OF TOWN! PLEASE NOTE: SOLAR PANELS ON ROOF ARE LEASED, AND LEASE IS TRANSFERABLE! APPROX $80 MONTH! SELLER NOTES WITH POWER COMPANY CREDITS, BILL HAS BEEN APPROX. $30 MONTH!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Diane Fuller (407-923-2090)
1534 WESCOTT LOOP, WINTER SPRINGS, FL 32708
$735,000111 Days on yellowkey MLS ID: O6380652
REDUCED by $10,000 (1.3%) on 05/25/2026
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3426 Built: 2004Monthly Fee: $100 Tax: $5,527 (2025)Community: Barrington EstatesSpa: YesSingle Family
Taxes:$5,527
Remarks: At ADJUSTED price of $735,000 for this stunning six-bedroom, four-bath home in a gated community, perfectly positioned with a view of a conservation lot without rear neighbors. Winter Springs address, with top-rated Oviedo Schools! Soak up the Florida lifestyle in this stunning backyard retreat with a sparkling pool and spa. Brand new pool heater plus a spacious outdoor kitchen, complete with a dedicated gas grill area, seating space, and brand new refrigerator. It is the ideal place to enjoy warm Florida days and breezy nights. Inside, the home offers a highly desirable layout, with both the primary suite and an additional bedroom on the first floor, perfect for a mother-in-law suite, guests, or a home office. The open living areas feature tile flooring throughout the main level, while the kitchen is finished with granite countertops and ample workspace for everyday living and hosting. Upstairs, you’ll find generously sized secondary bedrooms and baths, providing flexibility for large families, multigenerational living, or vacation use. The peaceful conservation views create a private, serene backdrop both indoors and out. Located in a gated community, this home combines space, privacy, and resort-style amenities in one exceptional property.
Listing is courtesy of: PALMANO GROUP RE BROKERAGE LLC (321-214-1211)
Listing Agent: Denise Pohlmann (407-701-3346)
702 GOLFPOINT DR, WINTER SPRINGS, FL 32708
$899,90050 Days on yellowkey MLS ID: O6397566
REDUCED by $25,100 (2.7%) on 05/26/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3660 Built: 1994Monthly Fee: $48 Tax: $11,586 (2025)Community: Glen Eagle Unit 3Spa: YesSingle Family
Taxes:$11,586
Remarks: One or more photo(s) has been virtually staged. *SELLER MOTIVATED* RARE OPPORTUNITY IN GLEN EAGLE/TUSCAWILLA! Set on a PROMINENT CORNER LOT in one of Winter Springs’ most sought-after golf communities, this spacious pool home offers an INCREDIBLE OPPORTUNITY for buyers looking to personalize a home with outstanding bones, flexible living space, and major system upgrades already completed. Major recent improvements including a NEW ROOF, FULL HOUSE REPLUMB, WHOLE-HOUSE ELECTRICAL UPGRADE, TWO NEW HVAC SYSTEMS, NEW POOL EQUIPMENT, and UPSTAIRS HARDWOOD FLOORS. Surrounded by mature oak trees, lush landscaping, and timeless curb appeal, the property offers a rare combination of space, flexibility, character, and long-term value in the heart of Tuscawilla. Inside, soaring ceilings, skylights, and custom white painted built-ins create a bright, open great room that feels both inviting and impressive. The open-concept layout flows easily for everyday living and entertaining, while the chef’s kitchen is designed to impress with 42-INCH WHITE CABINETRY, GRANITE COUNTERTOPS, a breakfast bar, a 36-inch GE Profile induction cooktop, GE Profile double ovens, microwave, and dishwasher, and a CUSTOM BUILT-IN LIEBHERR STAINLESS FRENCH DOOR REFRIGERATOR with dual bottom freezer drawers. Just off the foyer, the office is framed by gorgeous VINTAGE BEVELED GLASS DOORS, while the formal dining room with tray ceilings offers an elegant setting for hosting. The primary suite is filled with NATURAL LIGHT and OPENS DIRECTLY TO THE POOL and patio through FRENCH DOORS. The en suite bath features dual sinks, separate walk-in closets, a soaking tub, and a walk-in shower. The split floor plan continues on the opposite side of the home, where three additional bedrooms are positioned off the great room. One includes a private bath, another offers direct access to the pool and patio. One of the home’s most compelling features is the INCREDIBLE UPSTAIRS RETREAT. Beautifully updated with NEW HARDWOOD FLOORS, this expansive level offers a MASSIVE BONUS SPACE, an additional full bath, and an OVERSIZED 5th BEDROOM. Whether used for MULTIGENERATIONAL LIVING, a private guest retreat, POTENTIAL MOTHER IN-LAW SUITE, game room, media lounge, home gym, yoga studio, or separate family living area, the scale and versatility of this space truly set the home apart. Outdoor living is just as appealing, with a SCREENED POOL & PATIO designed for entertaining, relaxing, and making the most of FLORIDA LIVING. The side and backyard offer mature shade, privacy, and a fire pit area. PERFECTLY POSITIONED in sought-after Tuscawilla, 702 Golfpoint Drive offers the best of Winter Springs with EASY ACCESS to SR 417, Downtown Orlando, ORLANDO INTERNATIONAL AIRPORT, UNIVERSAL & DISNEY. Zoned for top-rated Seminole County schools and just moments from the Tuscawilla Country Club, local dining, fitness options, and the Cross Seminole Trail, this location makes it easy to enjoy weekend bike rides and morning runs to shopping, restaurants, and everyday convenience. Major recent improvements include: A new roof in 2021, full house replumbing in 2021, a whole-house electrical upgrade in 2021, all-new kitchen appliances in 2021, all new water faucets in 2021, two new HVAC systems in 2022, a new pool pump and spa/pool heater in 2023, new upstairs hardwood floors in 2024, a refinished pool deck in 2024, new garage door openers in 2026.
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Blake Murphey (407-637-7882)
805 LEOPARD TRL, WINTER SPRINGS, FL 32708
$565,00022 Days on yellowkey MLS ID: O6405925
0 Days Off yellowkey (back on 5/27/2026)
REDUCED by $10,000 (1.7%) on 05/25/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2608 Built: 1978 Tax: $2,946 (2024)Community: Winter Spgs Unit 4Single Family
Taxes:$2,946
Remarks: Under contract-accepting backup offers. Welcome to 805 Leopard Trail in Winter Springs, a 4-bedroom, 2-bath pool home located in a quiet, established no HOA community. Situated on approximately half an acre, this property offers a rare combination of space, privacy, and natural surroundings. The home features a functional layout with comfortable living areas, while large windows and sliding glass doors provide natural light and seamless access to the backyard. Step outside to a truly special outdoor setting, where mature trees, natural surroundings, and the sounds of nature create a peaceful and private atmosphere. The backyard is a standout feature, complete with a private pool and plenty of space to relax or entertain. The pool area is also plumbed for a future outdoor kitchen, offering additional potential. With a generous lot size, there is ample room for recreation, storage, or future improvements. Conveniently located near University of Central Florida, Central Winds Park, Oviedo Mall, as well as shopping, dining, and major roadways including SR 434 and SR 417, this property offers both tranquility and accessibility in a desirable Winter Springs location.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Wilfred Sierra Sosa, Pa (863-588-8303)
1815 SENECA BLVD, WINTER SPRINGS, FL 32708
$999,000162 Days on yellowkey MLS ID: O6368232
REDUCED by $30,000 (2.9%) on 05/20/2026
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
Remarks: Welcome to this beautifully reimagined 5-bedroom, 3 full bath, 2 half bath pool home located in the highly sought-after Chelsea Woods community of Tuscawilla. Blending timeless architectural character with extensive modern updates, this move-in ready home offers exceptional space, style, and functionality throughout. Step inside to discover expansive living areas designed for both everyday living and entertaining, including a large formal living room with a stunning brick fireplace, a spacious family room with a second fireplace, formal dining room, and an oversized bonus space ideal for a home office, playroom, media room, or flex living area. The completely remodeled kitchen is a true centerpiece, featuring quartz countertops, brand-new appliances, custom two-tone cabinetry, open shelving, designer finishes, and a stylish bar area perfect for hosting. A spacious laundry room with a convenient butler’s pantry area adds additional storage and functionality. Downstairs also includes two beautifully updated half bathrooms. Upstairs, all five bedrooms offer generous space and natural light, along with three fully renovated bathrooms, including a Jack-and-Jill layout. The expansive primary suite serves as a private retreat with soaring ceilings, a luxurious freestanding soaking tub, oversized walk-in shower, dual vanities, and elevated designer finishes throughout. Additional updates include a newer roof in 2023, both A/C units replaced 12/2025, wood-look tile flooring throughout the lower level, and luxury vinyl plank flooring upstairs. Outside, enjoy Florida living at its best with a covered and screened lanai overlooking the sparkling pool and spacious patio area—perfect for relaxing or entertaining year-round. Located in one of Tuscawilla’s most desirable neighborhoods and zoned for top-rated Seminole County schools, this rare fully updated home combines architectural charm, modern design, and an unbeatable location. Homes with this level of renovation, space, and character rarely become available in Chelsea Woods. Call today to schedule your private showing.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Belinda Gonzales (321-277-8994)
872 FALKIRK DR, WINTER SPRINGS, FL 32708
$438,99799 Days on yellowkey MLS ID: O6383538
REDUCED by $10,000 (2.2%) on 05/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1554 Built: 1978Monthly Fee: $35 Tax: $2,381 (2024)Community: Highlands Sec 1Spa: NoSingle Family
Taxes:$2,381
Remarks: BACK ON THE MARKET DUE TO BUYERS FINANCING FALL TROUGH!! Beautifully maintained home located in one of the most desirable areas of Winter Springs, offering the perfect blend of comfort, convenience, and outdoor living. Surrounded by scenic walking and biking trails throughout the neighborhood, this home delivers a peaceful setting while staying close to everything you need. This property features 3 bedrooms and 2 bathrooms with a bright open floor plan ideal for both everyday living and entertaining. The kitchen is equipped with stainless steel appliances and flows seamlessly into the main living areas, creating a spacious and inviting atmosphere. Step outside to your private screened pool area, perfect for relaxing or hosting gatherings, all within a fully fenced backyard that provides excellent privacy. Whether enjoying Florida sunshine or evening outdoor dining, this space is designed for year-round enjoyment. Conveniently located near shopping centers, restaurants, and major highways, offering easy access to Orlando, employment hubs, and surrounding communities while still enjoying the charm of a sought-after residential area. This home combines a desirable location, functional layout, and outdoor lifestyle — making it an excellent opportunity for homeowners and long-term value. Some photos were virtually staged.
Listing is courtesy of: CAISSA REALTY INVESTMENT INC (407-364-3056)
Listing Agent: Elizabeth Rodriguez (407-480-8829)
1513 BLACK BEAR CT, WINTER SPRINGS, FL 32708
$1,479,50085 Days on yellowkey MLS ID: O6385058
1 Days Off yellowkey (back on 5/27/2026)
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: Under contract-accepting backup offers. 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)
143 HAYES RD, WINTER SPRINGS, FL 32708
$479,00014 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)
1200 ROYAL OAK DR, WINTER SPRINGS, FL 32708
$499,99930 Days on yellowkey MLS ID: O6401888
REDUCED by $10,001 (2.0%) on 05/26/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2378 Built: 1981Monthly Fee: $118 Tax: $4,618 (2025)Community: Fairway Oaks Unit 1Single Family
Taxes:$4,618
Remarks: Welcome to the highly sought after Fairway Oaks at Tuscawilla community, where homes like this rarely come available! This spacious home features 3 bedrooms and 3 full bathrooms, 2,378 square feet of thoughtfully designed living space, and a private pool in the generously sized, fenced-in backyard oasis. As you enter through the private courtyard, discover the details that make this home so special. The luxury vinyl floors throughout the first floor are not only beautiful but designed for durability. The great room features a floor to ceiling wood burning stone fireplace, soaring cathedral ceilings, and stunning oversized windows which fill the home with natural light throughout. Granite countertops, a breakfast bar, ample storage, and ALL NEW black stainless-steel appliances are just some of the reasons you’ll love this kitchen, which flows naturally into the formal dining room. The first bedroom is situated downstairs, and includes its own ensuite full bathroom, perfect for those needing an in-law suite or multigenerational living. Upstairs you’ll find another full bathroom with a shower/tub combo, the second bedroom, and the primary suite. The primary bathroom includes a walk-in shower and separate bathtub, and the bedroom showcases a private balcony with recently updated flooring; the perfect place to relax and unwind while overlooking the 15th hole of the Tuscawilla golf course! At the back of the house an enclosed Florida room adds additional flex space to fit any lifestyle. Enjoy Florida living in the private pool and large fenced-in backyard, with peace of mind knowing that lawncare (front and back) is covered by the very reasonable, low-cost HOA! Additional features include updated electric panel (2024), new vent fans in all 3 bathrooms, and UV lights installed in both AC intakes to improve the air quality throughout the house and increase energy efficiency. Zoned for some of the best schools Central Florida has to offer, just minutes away from the Oviedo Mall, and right around the corner from the Tuscawilla country club which offers a fitness center, tennis courts, a junior Olympic sized swimming pool, and an 18-hole golf course, you really can’t beat this location! Schedule a showing today!
Listing is courtesy of: THE PALMS PROPERTY GROUP (407-476-4202)
Listing Agent: Austin Masi (407-476-4202)
1447 BIRD RD, WINTER SPRINGS, FL 32708
$2,799,00084 Days on yellowkey MLS ID: O6388126
REDUCED by $101,000 (3.5%) on 05/20/2026
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
Elementary School: Sterling Park Elementary
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)
294 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$249,9905 Days on yellowkey MLS ID: O6409921
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1105 Built: 1994Monthly Fee: $127 Tax: $3,612 (2025)Community: Deersong 2Single Family
Taxes:$3,612
Remarks: Beautifully maintained 2-bedroom, 2-bath single-family home located in the desirable Deersong community of Winter Springs! Built in 1994 and offering 1,105 heated square feet, this move-in-ready home features numerous major updates for peace of mind. Recent improvements include interior paint (2025), waterproof laminate flooring in the living room and both bedrooms (2025), a full-home repipe (2026), and a water heater (2026). Additional big-ticket upgrades include the roof replacement in 2018 and the AC installed in 2015. The functional floor plan offers comfortable living spaces filled with natural light, vaulted ceilings, and the updated laminate flooring adds a modern touch throughout. Conveniently located near shopping, dining, parks, Winter Springs Town Center, and top-rated Seminole County schools, this home is perfect for first-time buyers, downsizers, or anyone looking for low-maintenance living in a great location.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Jadel Patterson, Llc (407-922-5936)
314 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$279,990231 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: 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)
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