Location: Winter Springs
Do Not Show Listings
1447 BIRD RD, WINTER SPRINGS, FL 32708
$2,625,000115 Days on yellowkey MLS ID: O6388126
REDUCED by $174,000 (6.2%) on 06/03/2026
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 6132 Built: 2026 Tax: $2,989 (2024)Community: Talis CrossingSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,989
Elementary School: Sterling Park Elementary
High School: Winter Springs High
Tax Year: 2024
Middle School: South Seminole Middle
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)
497 CLUB DR, WINTER SPRINGS, FL 32708
$218,00044 Days on yellowkey MLS ID: O6408474
REDUCED by $14,800 (6.4%) on 05/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1224 Built: 1987Monthly Fee: $520 Tax: $3,344 (2025)Community: Cypress ClubTownhouse
Taxes:$3,344
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Beautiful 2/2 townhome in highly desirable Cypress Club community in The Highlands of Winter Springs, located in close proximity to SR 434! Light and neutral colors throughout, freshly painted approximately two years ago! *Vaulted ceiling in the spacious family/great room with a wood burning fireplace! Tile flooring in the living areas and laminate in the bedrooms. Split bedroom floorplan, with one bedroom downstairs. Tub and shower combination in both bathrooms. **Brand New Lennox A/C system* and a washer and dryer included! Screened and Covered porch and an additional outside storage closet for additional storage. Community pool in addition the master community pool! Brand new roofs in the community, HOA covers building insurance and grounds maintenance. Two assigned parking spaces and additional visitor parking. The community offers a fabulous club house, nature walking trails, parks, playground and tennis courts. Located close to shops and restaurants and very close to SR 434, SR 17/92 and SR 417 for easy commuting.
Listing is courtesy of: WATSON REALTY CORP (407-323-3200)
Listing Agent: Edyta Olejnik (407-474-0213)
143 HAYES RD, WINTER SPRINGS, FL 32708
$479,00045 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)
1209 DEER RUN DR, WINTER SPRINGS, FL 32708
$775,0002 Days on yellowkey MLS ID: O6420511
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3164 Built: 1977Monthly Fee: $3 Tax: $4,064 (2025)Community: TuskawillaSpa: NoSingle Family
Taxes:$4,064
Elementary School: Keeth Elementary
Middle School: Indian Trails Middle
Remarks: Beautiful Five bedroom, 3 bathroom home, in highly sought after Tuskawilla golf community. The primary bedroom has an adjoining room that can be used as an office or gym area. You can sit by your pool overlooking a large backyard with a lake view. The home was recently updated with a new roof in 2026 and the kitchen was remodeled approximately 2 years ago. There are 2 central heat and air systems and a whole house water filtration system. Volunteer HOA with no HOA restrictions. Located in A-rated Seminole county school system.
Listing is courtesy of: EXIT REAL ESTATE RESULTS (352-933-0018)
Listing Agent: Tommy Fransen, Jr (407-724-1712)
1385 PONCE DE LEON BLVD, WINTER SPRINGS, FL 32708
$367,0002 Days on yellowkey MLS ID: W7887141
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1460 Built: 1980Monthly Fee: $29 Tax: $4,679 (2025)Community: Sunrise Unit 2-ASingle Family
Taxes:$4,679
Elementary School: Rainbow Elementary
High School: Oviedo High
Remarks: Hit the "EASY BUTTON" on Your Next Home! Welcome to this beautifully updated, low-maintenance gem in the highly sought-after Sunrise subdivision. Whether you are a first-time buyer or looking to downsize, this home offers total peace of mind with major, big-ticket updates already done for you: Brand-New Roof (May 2026): Move in with zero roof worries for years to come. Fresh Updates: Brand-new flooring in all bedrooms and the guest bath, plus a beautifully remodeled guest bathtub featuring elegant porcelain tile. Upgraded Appliances: Features a brand-new, spacious 25-cubic-foot refrigerator. Plus, every major appliance (with the exception of the dishwasher) has been replaced within the last three years. A Rare, Massive 1/3-Acre Lot Step outside into your own private oasis. Sitting on an oversized 1/3-acre lot, the backyard offers incredible space and privacy that is hard to find in this area. For the Gardener: Includes a mature, highly coveted Coconut Cream mango tree, with an active irrigation system already piped and ready for three more trees of your choice. Shaded Evenings: Because the home faces west (with the sun setting beautifully on the front), your back patio stays perfectly cool, shaded, and delightful for evening relaxation and outdoor dining. Prime Location Perfectly situated for convenience and community perks: Steps from Fun: A neighborhood playground is just two lots away, and the community tennis courts are right around the corner. Unbeatable Convenience: Quick, seamless access to SR-417 makes commuting a breeze, with premier shopping and dining just minutes away. Would you like a boat? Sunrise allows storing boats up to 24 feet in the back yard. With the major maintenance checked off your list, all that's left to do is move in and enjoy.
Listing is courtesy of: LISTWITHFREEDOM.COM (855-456-4945)
Listing Agent: Ralph Harvey (855-456-4945)
1055 CHESTERFIELD CIR, WINTER SPRINGS, FL 32708
$499,90025 Days on yellowkey MLS ID: O6413841
0 Days Off yellowkey (back on 6/27/2026)
REDUCED by $10,100 (2.0%) on 06/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1665 Built: 1984Monthly Fee: $25 Tax: $5,048 (2025)Community: AmherstSpa: NoSingle Family
Taxes:$5,048
Remarks: Under contract-accepting backup offers. Beautiful pool home located in the highly desirable Amherst community of Winter Springs! Situated on an oversized .34-acre lot, this well-maintained 3-bedroom, 2-bath home offers a spacious split-bedroom floor plan with vaulted ceilings, abundant natural light, and a cozy wood-burning fireplace in the oversized family room. Updated bathrooms and ceramic wood looking flooring in main living areas. The screened with an large pool and covered lanai create the perfect setting for year-round outdoor living and entertaining, and no rear neighbors for privacy. The primary suite features a walk-in closet and spacious bath with dual sinks newly remodeled. Additional highlights include a 2-car garage, irrigation system, rain gutters, public utilities, and low annual HOA dues. New Roof (2025), New Water Heater & A/C (2024). Conveniently located near top-rated Seminole County schools, parks, shopping, dining, major roadways, and the 417.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Brittany Zapitz (321-230-4445)
600 NORTHERN WAY #906, WINTER SPRINGS, FL 32708
$290,000151 Days on yellowkey MLS ID: O6375918
REDUCED by $20,000 (6.5%) on 06/01/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1609 Built: 2016 Tax: $4,259 (2024)Community: Tuscany Place Ph 1Condo
Taxes:$4,259
Remarks: Turnkey townhouse in Tuscany Place is totally move-in ready. The townhouse style is limited to only a few homes in the new phase of this wonderful, gated community. Built in 2016 and much newer than many competing condos/townhomes. All 3 bedrooms have their own private full bathrooms. The first-floor bedroom with en-suite bath is great for guests, home office, or multigenerational living. Brand new roof (2026). Newer HVAC (2020). Low maintenance townhouse-style living. Spacious open-concept kitchen and overall excellent layout. This home's natural focal point is the kitchen with granite countertops, and there's an extra-large kitchen island, which provides essential counter space and storage, cabinets and drawers, and room for a breakfast bar. The kitchen leads to the rest of the living and family room combination, which features glass sliding doors to the patio and a staircase to a great split plan layout for the bedrooms upstairs. This home has all the features you’re looking for including a laundry room with large-size appliances, walk-in closets, a huge refrigerator, dedicated trash drawer in the kitchen, blinds and window treatments, and modern fixtures throughout the home. See yourself living in the heart of beautiful Winter Springs. Low monthly fee covers access to the community pool, exterior maintenance and landscaping, sewer, and trash services. Very close to all the shopping and restaurants at Winter Springs Town Center, and Trotwood Park is right at your doorstep. Contact us today to schedule a private tour!
Listing is courtesy of: JR REALTY GROUP LLC (407-920-4624)
Listing Agent: John Vincent (407-534-9764)
4901 PETRA CT, WINTER SPRINGS, FL 32708
$674,90031 Days on yellowkey MLS ID: O6412001
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2644 Built: 1986Monthly Fee: $40 Tax: $2,783 (2024)Community: TuskabaySingle Family
Taxes:$2,783
Remarks: Make yourself at home in this spacious, beautifully undated residence located in one of the most desirable and sophisticated neighborhoods in Winter Springs, in the heart of Central Florida. This spacious four bedroom, two bath split-plan home offers comfort and versatility throughout . Features include a formal dining room; inviting Florida room, private den, and a generously sized master suite designed for relaxation. With a thoughtful layout and plenty of space, this home is perfect for both everyday living and entertaining. All kitchen appliances are included featuring 42" custom, cabinetry, carpet in the living room and all bedrooms. Bamboo flooring in the sunroom and office with ceramic tile in the kitchen, bathrooms and laundry room (with pull-down ironing board). The living room features an electric fireplace, built in bookshelves, vaulted ceiling, that creates a warm and inviting atmosphere in the heart of the home. Move in ready. Roof; 2016, AC/heat pump; 12/24, microwave; 2026, electric box; 1/2025, replumbed entire house; 2023.
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)
Listing Agent: Pat Long (407-406-6733)
510 SONATA CT, WINTER SPRINGS, FL 32708
$799,90062 Days on yellowkey MLS ID: O6402358
REDUCED by $25,000 (3.0%) on 06/23/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2381 Built: 1999Monthly Fee: $184 Tax: $6,415 (2024)Community: Seville ChaseSingle Family
Taxes:$6,415
Remarks: SELLER MOTIVATED!! Make OFFER! Freshly Painted Exterior and Interior! Walk in and feel instantly at home! This beautifully renovated 4-bedroom, 3-bathroom triple-split pool home sits on nearly half an acre in the gated community of Seville Chase and is completely move-in ready. Step inside to soaring ceilings and a thoughtfully designed open layout that still offers comfortable separation of space. You’ll immediately notice the stunning porcelain tile floors and a high-end, fully updated kitchen featuring custom cabinetry, pull-out shelving, soft-close drawers and doors, and sleek quartz countertops—perfect for both everyday living and entertaining. Recent upgrades provide peace of mind, including: New tile roof (2025) with a 50-year warranty AC replaced in 2022 Water softener (2022) New pool pump Out back, enjoy your own private retreat with a screened pool overlooking a serene conservation area with a lake—ideal for relaxing or even bass fishing. The expansive yard also features mature fruit trees, including avocado, mango, lemon, and a cherry bush. All of this is conveniently located near Winter Springs, major highways (417 & 434), UCF, Seminole State College, and major employers like Lockheed Martin and Siemens. This home truly has it all—style, space, and location. Schedule your private showing today before it’s gone!
Listing is courtesy of: VOSS REALTY INC (407-456-0777)
Listing Agent: Lindsay Kaye Voss (407-456-0777)
1201 WOLVERINE TRL, WINTER SPRINGS, FL 32708
$500,000162 Days on yellowkey MLS ID: O6374676
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1979 Built: 1977 Tax: $5,709 (2024)Community: Winter Spgs Unit 4Single Family
Taxes:$5,709
Remarks: Welcome to this charming 4-bedroom, 2-bath home tucked away in a quiet, tree-lined neighborhood in desirable Winter Springs. Surrounded by mature trees, this property offers a peaceful atmosphere and a spacious backyard, ideal for entertaining, relaxing, or enjoying Florida outdoor living. Inside, you’ll find a warm and inviting layout highlighted by an original masonry fireplace, adding timeless character and charm. Skylights in the living room and hallway flood the home with natural light, creating a bright and airy feel throughout the main living spaces. Conveniently located near schools, parks, shopping, dining, and major roadways, this home offers the perfect blend of tranquility and accessibility in an established community.
Listing Agent: Nairobi Rondon (786-935-0365)
1035 N ELK CT, WINTER SPRINGS, FL 32708
$900,00021 Days on yellowkey MLS ID: O6414324
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3360 Built: 1978 Tax: $10,432 (2025)Community: Winter Spgs Unit 2Spa: YesSingle Family
Taxes:$10,432
Remarks: Under contract-accepting backup offers. Seller may consider buyer concessions if made in an offer ~ Over 1.3 PRIVATE ACRES, a DREAM BACKYARD, and a home filled with character – this is the kind of property that rarely comes to market in the heart of Winter Springs! Set on a secluded 1.32 ACRE CUL-DE-SAC LOT with an optional HOA, this beautifully UPDATED SINGLE STORY POOL HOME offers more than 3,000 square feet of versatile living space with 4 bedrooms, 3.5 baths, a dedicated FLEX/DEN, BONUS ROOM, and a flowing floor plan designed for everyday living and unforgettable entertaining. Major updates include A/C systems updated (2022/2023), septic service in (2022), and a 2016 roof, giving peace of mind for years to come. The GATED COURTYARD ENTRY welcomes you home, while the circular driveway provides abundant parking for family and guests. Inside, you will find no carpet – just WOOD LOOK TILE, wood laminate flooring, and new SLATE TILE in the chef's kitchen. Thoughtfully updated with rich cabinetry topped with crown molding, sleek stone countertops, a striking herringbone backsplash, breakfast bar seating, upgraded STAINLESS STEEL APPLIANCES including a built-in wall oven, and a layout that opens seamlessly to the living spaces, this kitchen was made for gathering. Crown molding, custom accent details, a cozy WOOD BURNING FIREPLACE, updated bathrooms, and charming architectural touches throughout give this home a warmth, style, and personality you simply can't recreate. Designed to embrace Florida living, three sets of FRENCH DOORS and windows from the main living areas and oversized sliding glass doors from the PRIMARY SUITE open to an incredible COVERED LANAI featuring a beautiful WOOD SLAT CEILING, generous spaces for outdoor dining and relaxing, and views of the SCREENED HEATED POOL and separate SPA with a PERGOLA/BAR. Beyond the lanai, discover your own private retreat complete with mature trees, winding garden paths, a FIRE PIT, fenced dog run, lush landscaping, and endless green space that feels worlds away from the city. Located in one of Winter Springs' most desirable areas with TOP-RATED SCHOOLS and easy access to Tuskawilla Road, Red Bug Lake Road, SR 417, shopping, dining, parks, golf, the Tuscawilla Country Club, Trotwood Park, Bear Creek Nature Trail, the Oviedo Mall and a variety of everyday conveniences, this is a rare opportunity to enjoy unmatched privacy, space, and timeless charm without sacrificing location. Homes offering this much land, versatility, and outdoor living in the heart of Winter Springs are few and far between – schedule your private showing today and fall in love with this exceptional property!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
525 SADDLEWOOD LN, WINTER SPRINGS, FL 32708
$685,00017 Days on yellowkey MLS ID: O6416232
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3246 Built: 1996Monthly Fee: $42 Tax: $4,016 (2025)Community: Winding Hollow Unit 2Single Family
Taxes:$4,016
Elementary School: Layer Elementary
Remarks: Pride of ownership shows in this updated Winding Hollow, one owner, 2 story gem w/ 4 bedrooms & 3 baths plus a bonus room & 3 car garage. This home showcases comfort and versatility w/ tile floors throughout the downstairs including the screened lanai, which is accessible from the living & family rooms & primary suite. The open concept bright & modern floorplan has great flow & is perfect for entertaining with soaring 18’ ceilings & high glass windows that bring the outside in. The remodeled island kitchen is open to the dinette & family room & is outfitted with hard surface counter tops, plentiful cabinet space, pantry and modern appliances. The primary suite has a sitting area currently used as a home office, has 2 spacious closets & an updated en-suite bath featuring a modern soaking tub & quartz countertops vanity w/ dual sinks. Bedroom 2 is also on the 1st floor as are the spacious & open living & dining room areas. Upstairs you will find an upgraded laminate wood stairway & flooring for the two bdrs, a hall bath, & a balcony bonus room / flex space that could be converted to another bedroom & overlooks the downstairs kitchen & family room. More features include a laundry room off the kitchen, spacious 3 car garage w/ expanded driveway to accommodate cars, a newer roof & 2 zoned A/C's plus recent paint both inside & out. This location is with-in walking distance of the Cross Seminole trail & Central Winds Park, and offers convenient proximity to wonderful Winter Springs schools, shopping and state roads for easy commutes such SR 417 and 17-92. This magnificent home will exceed your expectations & Welcome home!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Rob Breese, Iii (321-436-8813)
156 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708
$665,00069 Days on yellowkey MLS ID: O6394958
REDUCED by $7,500 (1.1%) on 06/25/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2509 Built: 1999Monthly Fee: $187Community: Seville ChaseSingle Family
Taxes:$0
Remarks: Virtually Staged. Welcome to refined Florida living in the exclusive gated community of Seville Chase, a hidden gem in desirable Winter Springs. With just 110 homes, this intimate community offers a rare blend of privacy, charm, and timeless appeal. As you enter, you’re greeted by the picturesque, tree-lined Seville Chase Drive, where mature landscaping and a serene community pond set the tone for a tranquil, elegant lifestyle. This beautifully designed one-owner, four-bedroom, three-bath residence features a highly sought-after three-way split floor plan, offering both comfort and privacy for family and guests alike. Thoughtfully laid out, the home flows effortlessly from one space to the next, creating an inviting atmosphere ideal for both everyday living and entertaining. From the moment you step inside, you’ll appreciate the sense of quiet sophistication—where natural light, spacious living areas, open concept kitchen, and well-appointed finishes come together in perfect harmony. The primary suite serves as a private retreat with ensuite bath that features a jacuzzi tub, separate shower, and walk-in closet, while secondary bedrooms are tucked away in separate wings, providing flexibility for guests, a home office, or multigenerational living. Whether enjoying peaceful mornings overlooking the surrounding greenery in your private screened lanai, or hosting gatherings in the generous living spaces, this home captures the essence of Florida living at its finest—where elegance meets ease in a setting that feels both luxurious and welcoming. Experience the beauty, privacy, and understated grandeur of Seville Chase—where every day feels like a retreat. This lovingly cared for home awaits your personal touches: ROOF (2023), HVAC (2022), 6 front impact WINDOWS and French PATIO DOORS (2024), water heater (2009), hurricane shutters, paver driveway, paver screened lanai.
Listing is courtesy of: VALENCE REALTY GROUP (407-797-5034)
Listing Agent: Cyndy Valence (407-810-3434)
947 GLEN ABBEY CIR, WINTER SPRINGS, FL 32708
$525,0007 Days on yellowkey MLS ID: O6418792
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2416 Built: 1997Monthly Fee: $126 Tax: $2,980 (2025)Community: Greenbriar Sub Ph 2Spa: NoSingle Family
Taxes:$2,980
Remarks: Welcome to 947 Glen Abbey Circle in the sought-after Greenbriar Country Club and Golf Course community of Winter Springs. This impeccably maintained 4-bedroom, 3-bathroom home with a spacious loft offers thoughtfully designed living space with beautiful conservation views and a flexible floor plan perfect for everyday living and entertaining. The bright and open layout features soaring ceilings in the formal living and dining areas, creating an impressive first impression. The spacious kitchen is equipped with wood cabinetry, ceramic tile flooring, and overlooks the family room, where sliding glass doors lead to a screened porch overlooking the peaceful conservation area. The first-floor primary suite provides a private retreat with a large walk-in closet, garden tub, separate shower, and dual vanity. An interior laundry room and convenient half bath complete the main level. Upstairs, you'll find three additional bedrooms, a full bathroom, and a versatile loft that overlooks the living and dining areas below, enhancing the home's open and airy feel. Whether used as a game room, home office, media space, or play area, the loft adds flexibility to meet a variety of lifestyle needs. Recent updates and meticulous care throughout make this property truly move-in ready. Enjoy the lifestyle that Greenbriar offers, with access to golf, country club amenities, top-rated Seminole County schools, shopping, dining, and major roadways just minutes away. This is a rare opportunity to own a beautifully maintained home in one of Winter Springs' most desirable communities. Schedule your private showing today.
Listing Agent: Denise Mckinley (407-625-0635)
661 ANDOVER CIR, WINTER SPRINGS, FL 32708
$435,00012 Days on yellowkey MLS ID: O6417072
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1735 Built: 1994Monthly Fee: $125 Tax: $5,042 (2025)Community: Georgetowne Unit 3Spa: NoSingle Family
Taxes:$5,042
Remarks: Welcome to 661 Andover Circle, a beautifully updated home in the sought-after Tuscawilla community of Winter Springs. This move-in ready residence features ceramic tile flooring, fresh interior paint, and a spacious split-bedroom floor plan designed for comfortable living. The updated kitchen offers granite countertops, newly painted cabinetry, a brand-new range, ample storage, and a functional layout perfect for everyday living and entertaining. The spacious primary suite provides a private retreat, while a brand-new HVAC system offers peace of mind for years to come. Enjoy Florida living year-round from the screened rear patio, perfect for relaxing with your morning coffee or entertaining family and friends. Conveniently located near Trotwood Park, you'll have easy access to pickleball and tennis courts, playgrounds, sports fields, covered pavilions, and more. Just around the corner, Tuscawilla Country Club features tennis facilities and a beautiful 18-hole golf course for those who enjoy an active lifestyle. The HOA covers front lawn maintenance, providing low-maintenance living. Located near top-rated Seminole County schools, shopping, dining, the Seminole Trail, and SR-417, this home offers the perfect combination of comfort, convenience, and community. Don't miss your opportunity to own this beautifully updated Tuscawilla home. Schedule your private showing today! Please note that the home does not have a backyard sprinkler system. All information pertaining to the property is deemed reliable, but not guaranteed. Information to be verified by the Buyer. Be advised that cameras may exist recording audio and video inside/outside the property, such as ring doorbells. Photos are digitally enhanced and could be altered, please verify.
Listing is courtesy of: DJ & LINDSEY REAL ESTATE (904-643-6199)
Listing Agent: Christopher Anuszewski (407-230-7921)
4209 LORI LOOP, WINTER SPRINGS, FL 32708
$625,00051 Days on yellowkey MLS ID: O6406486
0 Days Off yellowkey (back on 6/25/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2428 Built: 1986Monthly Fee: $17 Tax: $6,046 (2024)Community: Willow RunSingle Family
Taxes:$6,046
Elementary School: Red Bug Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Under contract-accepting backup offers. A home this loved is hard to find. Lovingly maintained and thoughtfully improved over the years, this traditional 4-bedroom, 3-bath heated saltwater pool home in the desirable Willow Run community of Winter Springs showcases true pride of ownership throughout. The desirable three-way split floor plan offers exceptional privacy and flexibility for families, guests, multi-generational living, or a home office setup. Surrounded by lush, mature landscaping cultivated with care, this Seminole County pool home blends timeless character with thoughtful updates designed for comfortable everyday living and effortless entertaining. Freshly painted throughout, the interior offers a bright, clean backdrop ready for your personal style. Newer windows fill the home with natural light, while solid wood bedroom doors add warmth and quality craftsmanship throughout. The spacious family room is anchored by a classic wood-burning fireplace, creating an inviting gathering space for family and friends. ROOF 6/2026 Major updates provide valuable peace of mind, including a newer HVAC system (2020) with Blue Light air purification and service contract, Water Heater (2026), and a brand-new roof being installed June 17, 2026. Florida outdoor living takes center stage with a heated saltwater pool, safety fence, expansive stone-finished pool deck, oversized rear porch, widened driveway, charming front porch, and decorative wrought iron fencing. Whether hosting gatherings, tending the garden, relaxing poolside, or enjoying year-round outdoor living, this property offers the lifestyle many Central Florida buyers are seeking. Located in the heart of Winter Springs, this home offers exceptional convenience with quick access to SR-417, making commuting throughout Central Florida a breeze. Residents enjoy proximity to Winter Springs Town Center, Tuscawilla Country Club, Central Winds Park, the Cross Seminole Trail, shopping, dining, and highly regarded Seminole County schools. Winter Park is approximately 20 minutes away, while Orlando's major theme parks and Florida's east coast beaches can be reached in about 55 minutes, providing easy access to some of the region's most popular destinations. If you're searching for a meticulously maintained pool home in Winter Springs with major updates already completed, exceptional outdoor living spaces, and a location that combines convenience with community, this Willow Run gem deserves your attention. Schedule your private showing today.
Listing Agent: Laura Leigh Wood (407-310-4908)
203 SWEETGUM, WINTER SPRINGS, FL 32708
$420,00010 Days on yellowkey MLS ID: O6417974
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1218 Built: 1973 Tax: $925 (2025)Community: North Orlando Terrace Unit 2 Sec 8Spa: NoSingle Family
Taxes:$925
Remarks: This meticulously maintained home offers an impressive combination of recent upgrades, thoughtful features, and exceptional outdoor living. The curb appeal is enhanced by professional landscape lighting, while 10-foot access gates on both sides of the property provide convenience and flexibility. A three-zone irrigation system helps maintain the beautifully landscaped grounds year-round. The backyard is designed for relaxation and enjoyment, featuring a sparkling pool with a removable safety fence, a LED pool light replaced in 2025, and a new pool pump and filter installed in 2026. For additional storage, workshop space, or hobby use, the property also includes a substantial 12’ x 20’ steel accessory building. No HOA, so bring your toys, Rv, camper etc! Inside, the garage has been refreshed with newly painted floors and walls and is illuminated by six custom LED light fixtures, creating a bright and functional space. Major system updates provide peace of mind, including a new roof installed in March 2026, a new central air conditioning system installed in March 2025, and a new hot water heater installed in May 2026. Additional recent improvements include a refrigerator replaced in 2024, a dishwasher installed in 2024, a garbage disposal added in 2025, a Google Nest smart thermostat installed in 2026, and an updated master bathroom toilet. With extensive recent improvements, modern conveniences, and pride of ownership evident throughout, this move-in-ready home offers outstanding value and is ready for its next owner to enjoy.
Listing is courtesy of: CENTURY 21 ALTON CLARK (407-636-4637)
Listing Agent: Joseph Connolly (631-365-6085)
170 WOODED VINE DR, WINTER SPRINGS, FL 32708
$649,90011 Days on yellowkey MLS ID: O6418077
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2470 Built: 2019Monthly Fee: $137 Tax: $8,571 (2025)Community: Tuskawilla Crossings Ph 1Single Family
Taxes:$8,571
Remarks: Built in 2019, this thoughtfully designed floor plan is ideal for multigenerational living, extended stays for guests, remote professionals, or anyone seeking additional privacy and versatility. The main residence encompasses 3 bedrooms, 2.5 bathrooms, and a dedicated office/flex room, while a separate 1 bedroom, 1 bath suite above the garage creates a private retreat complete with its own entrance. The main level showcases an open concept design where the family room flows seamlessly into the spacious eat in kitchen. The kitchen is beautifully appointed with 42" cabinetry, quartz countertops, upgraded stainless steel appliances, and a generous walk in pantry. A versatile office/flex room offers endless possibilities as a home office, playroom, fitness area, study space, or hobby room. Upstairs, the primary bedroom serves as a comfortable escape, featuring a walk-in closet, French doors that lead to a private balcony and a spacious en suite bath with dual vanities, a garden tub, and separate walk-in shower. Two additional bedrooms and a full bath with dual sinks complete the second floor of the main residence. One of the home's most desirable and unique features is the private in-law suite above the garage. Measuring approximately 19' x 16', this separate living space includes its own full bathroom, dedicated HVAC system, built-in cabinetry and private entrance, making it ideal for in-laws, guests, college aged children, a home business, or additional flex space. The remainder of the home highlights a front porch, a covered rear porch, a brick paved driveway, oversized parking area, two car garage, whole home Gigabit Wi Fi, fiber internet, smart locks, smart lighting and a 60 amp outlet ready for electric vehicle charging. Residents of Tuskawilla Crossings enjoy resort style amenities including a community pool with cabanas, playground, walking trails, multiple dog parks, and direct access to the Seminole County Trail. Ideally located just minutes from Winter Springs Town Center, shopping, dining, top rated Seminole County schools, and SR 417.
Listing is courtesy of: DIBS REALTY, LLC (407-537-2232)
Listing Agent: Ashley Swindell (407-687-5481)
1406 BLUMBERG BLVD, WINTER SPRINGS, FL 32708
$420,00042 Days on yellowkey MLS ID: O6408695
REDUCED by $5,000 (1.2%) on 06/19/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1476 Built: 2024Monthly Fee: $356 Tax: $6,076 (2025)Community: Hickory Grove TwnhmsTownhouse
Taxes:$6,076
Remarks: Welcome to this almost-new townhome in beautiful Winter Springs! Located in the desirable Hickory Grove community, where you will find a maintenance free living, relaxing pool and cabana, playground for the little ones and a dog park for your furry friend, all just a few steps away and NO CDD to pay. The monthly HOA dues also include: landscaping, irrigation, weed control, exterior paint, roof, 1GB of high speed internet and cable premium package. This stunning residence has been tastefully decorated and offers the perfect blend of modern style, comfort, and convenience. Your front door opens up to the serene parks, fountains and walkways just across the street from your favorite stores and restaurants. Enjoy an open-concept layout with plenty of natural light, a modern kitchen with state of the art SS appliances, quartz counters and a beautiful island to entertain your guests. 3 bedrooms, 2.5 bathrooms, and a 2-car garage, and much more. This home is move-in ready and designed for easy living. Upstairs, the generous primary suite offers a private retreat with an en-suite bath and ample closet space. Built with today’s lifestyle in mind, this home also includes the peace of mind of a builder warranty, this is a fantastic opportunity to own a like-new home in one of Central Florida’s most sought-after areas with top-rated schools.
Listing is courtesy of: RALISTO, LLC (407-493-6032)
Listing Agent: Kalex Espinosa (407-493-6032)
1815 SENECA BLVD, WINTER SPRINGS, FL 32708
$998,000193 Days on yellowkey MLS ID: O6368232
REDUCED by $1,000 (0.1%) on 06/25/2026
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
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 Agent: Belinda Gonzales (321-277-8994)
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