Location: Winter Springs
Keyword(s): Winter Springs High
Keyword(s) High School: Winter Springs High
Do Not Show Listings
4991 COURTLAND LOOP, WINTER SPRINGS, FL 32708
$750,00016 Days on yellowkey MLS ID: O6409511
1 Days Off yellowkey (back on 5/24/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3217 Built: 1983Monthly Fee: $40 Tax: $6,752 (2025)Community: TuskabaySpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,752
Elementary School: Keeth Elementary
High School: Winter Springs High
Tax Year: 2025
Middle School: Indian Trails Middle
Remarks: Under contract-accepting backup offers. MULTIPLE OFFERS : HIGHEST AND BEST DUE BY SATURDAY, MAY 23 at 5PM. Welcome to this beautifully updated 4-bedroom, 2.5-bath pool home in the highly sought-after Winter Springs community of Tuskabay, offering the perfect blend of style, comfort, and convenience. Ideally located near shopping, dining, and major commuter routes, this home boasts lush landscaping, exceptional curb appeal, and a desirable side-entry 2-car garage. Inside, you’ll find neutral paint and flooring, abundant natural light, and an open floorplan designed for both everyday living and entertaining. The inviting foyer showcases stunning custom woodwork that flows seamlessly into the spacious dining area, while custom wood ceilings in both the foyer and loft up above add warmth and character. Elegant wrought iron railings accent the staircase and dining space for a sophisticated touch. The thoughtfully designed kitchen is situated at the front of the home and features an oversized opening to the living areas for great lines of sight, 42” cabinetry, granite countertops, tile backsplash, stainless steel appliances including built-in microwave, oven, and cooktop, plus a dinette area and walk-in pantry with convenient laundry access. The oversized family room is truly the heart of the home, highlighted by vaulted ceilings, a cozy wood-burning fireplace, two skylights, and French doors that open to the covered patio for seamless indoor/outdoor living. The spacious upstairs primary suite is a private retreat complete with its own wood-burning fireplace, custom accent wall, French doors leading to a private balcony, and a large walk-in closet with custom organization system. The luxurious en-suite bath offers a wrap-around, double-sink vanity, jacuzzi tub, and oversized shower. Adjacent to the primary suite are a versatile loft and an office/nursery space perfect for working from home or additional flexibility. Downstairs, three generously sized bedrooms feature large closets and ceiling fans. One bedroom includes a private half bath with direct access to the pool deck, making it an ideal cabana bath. An additional full hall bath features an oversized vanity, linen closet, and shower/tub combination. Step outside to your own backyard oasis featuring a large, screened and covered paver patio with custom wood ceiling overlooking the spacious, heated, chlorine pool. Beyond the screened enclosure, there’s still plenty of yard space to enjoy, all enclosed by a vinyl fence for added privacy. Additional upgrades include newer AC, crown molding, plantation shutters, engineered wood flooring, and added lighting and electrical outlets throughout. This exceptional home offers the perfect combination of timeless character, modern updates, and resort-style outdoor living.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Jean Scott (407-759-5320)
1270 TARFLOWER DR, WINTER SPRINGS, FL 32708
$409,99024 Days on yellowkey MLS ID: O6407275
1 Days Off yellowkey (back on 6/2/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1678 Built: 2026Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Taxes:$1,457
Elementary School: Layer Elementary
Remarks: Under Construction. The Catalina II offers a spacious and modern open-concept design on the main level, creating the perfect setting for entertaining, everyday living, and gathering with family and friends. This thoughtfully designed townhome features 4 bedrooms, 2.5 bathrooms, and a rear-loading 2-car garage, blending functionality with contemporary style in desirable Winter Springs, FL. The owner’s suite serves as a private retreat, complete with a well-appointed ensuite bathroom and a generous walk-in closet. The chef-inspired kitchen is designed for both beauty and performance, showcasing stainless steel appliances, a walk-in pantry, and a convenient breakfast bar ideal for casual dining and hosting.
Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)
Listing Agent: Amanda Warren (321-662-0779)
560 PLEASANT GROVE DR, WINTER SPRINGS, FL 32708
$425,00040 Days on yellowkey MLS ID: O6401016
REDUCED by $20,000 (4.5%) on 05/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1654 Built: 1996Monthly Fee: $78 Tax: $5,669 (2024)Community: Tusca OaksSingle Family
Taxes:$5,669
Tax Year: 2024
Remarks: Welcome to Tuska Oaks—a well-established community in the heart of Winter Springs known for its convenience and neighborhood feel. Tucked away on a quiet cul-de-sac, this 3-bedroom, 2-bath home offers over 1,600 square feet of comfortable living space with a smart, open layout and soaring vaulted ceilings. The kitchen features granite countertops, stainless steel appliances, and ample cabinet space, opening seamlessly into the dining room area—ideal for everyday living and entertaining. Tile flooring runs throughout the home with laminate or LVP in the bedrooms and bathrooms, making maintenance simple and clean. Major updates have already been handled for you, including a roof replaced in 2018, A/C replaced in 2020, newer water heater (2024), and interior and exterior paint completed just 3 years ago. The secondary bathroom has been fully remodeled, adding a fresh, updated touch. Step outside to a screened-in back porch overlooking a fully fenced backyard, offering privacy and space for pets, play, or outdoor gatherings. Residents of Tuska Oaks enjoy a low HOA and access to a community pool , all while being conveniently located near shopping, dining, and top-rated Seminole County schools.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: David Fraser (407-920-9749)
114 SUNDANCE CT, WINTER SPRINGS, FL 32708
$305,500204 Days on yellowkey MLS ID: O6359275
3 Days Off yellowkey (back on 6/1/2026)
REDUCED by $10,000 (3.2%) on 04/23/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1356 Built: 1997Monthly Fee: $120 Tax: $4,059 (2024)Community: Seasons TheSpa: NoSingle Family
Taxes:$4,059
Elementary School: Winter Springs Elementary
Remarks: One or more photo(s) has been virtually staged. If you’ve been searching for space, location, and opportunity without overpaying, this cul-de-sac home delivers. Tucked away on a quiet cul-de-sac and backing to a peaceful conservation area with no rear neighbors, this 4-bedroom home offers a rare combination of privacy and value in one of Winter Springs’ most desirable locations. Inside, you’ll find a functional split-bedroom layout, vaulted ceilings, and an open living and dining space designed for everyday comfort. The kitchen flows into a bright dining nook and screened patio, creating an ideal setup for indoor-outdoor living. With major updates already completed, including a 2022 roof, and 2026 water heater, buyers can move in with confidence while still having the flexibility to personalize finishes over time. Additional highlights include dedicated driveway parking for two vehicles, low HOA, and access to community amenities such as a pool, tennis courts, and playground. Located within top-rated Seminole County school zones and just minutes from parks, trails, shopping, and major roadways, this home is perfectly suited for buyers looking to maximize space, location, and long-term value. Back on market due to buyer financing — no inspection concerns.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-841-0888)
Listing Agent: Nora Rios (407-274-1174)
622 ANHINGA RD, WINTER SPRINGS, FL 32708
$384,900164 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 TILE ROOF INSTALLED APRIL 2026 + TRANSFERABLE 4-POINT INSPECTION + APPROXIMATELY 5-MINUTE WALK TO HIGHLANDS ELEMENTARY! Welcome to 622 Anhinga Road, a move-in-ready home located in the highly desirable Greenspointe community of Winter Springs. One of the most expensive updates a homeowner can face has already been completed with a BRAND-NEW TILE ROOF installed in April 2026, providing long-term value, durability, and peace of mind for years to come. To make the buying process even easier, the seller has already completed a transferable 4-Point Inspection available to the new owner. This beautiful 3-bedroom, 2.5-bathroom home offers over 1,700 square feet of living space and a highly desirable floor plan with the primary suite conveniently located on the first floor. The spacious owner's retreat features a large walk-in closet and a private bathroom with dual vanities, a soaking tub, separate shower, and private water closet. As you enter the home, you'll immediately notice the soaring ceilings, abundant natural light, and open-concept layout that creates a bright and welcoming atmosphere. The main living areas feature tile flooring throughout, while the kitchen offers granite countertops, stainless steel appliances, light cabinetry, a breakfast bar, and views of the living and dining areas—perfect for everyday living and entertaining. Sliding glass doors lead to a shaded backyard, creating the perfect space for relaxing, grilling, entertaining guests, or simply enjoying Florida evenings. Upstairs, you'll find a spacious loft that can easily serve as a home office, media room, playroom, gym, or second living area, along with two additional bedrooms and a full bathroom. Families will love the location within the highly rated Seminole County School District. Highlands Elementary School is just a short walk from the home, allowing many residents to enjoy the convenience of walking their little ones n to school in approximately 5 minutes. South Seminole Middle School and Winter Springs High School are also nearby. Residents enjoy access to The Highlands community amenities, including a community pool, tennis courts, pickleball courts, basketball courts, playgrounds, parks, clubhouse, walking trails, and recreational facilities designed for an active Florida lifestyle. Conveniently located near Winter Springs Town Center, UCF, Valencia College, shopping, dining, SR-417, SR-434, I-4, Downtown Orlando, and Central Florida attractions, this home offers both comfort and convenience in one of Seminole County's most sought-after communities. Vacant and easy to show. Major updates already completed, including a NEW TILE ROOF (April 2026), HVAC (2017–2018), WATER HEATER (2022), and a TRANSFERABLE 4-POINT INSPECTION. A rare opportunity to own a move-in-ready home in Winter Springs with top-rated schools, outstanding community amenities, and important updates already taken care of.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
201 BURGESS DR, WINTER SPRINGS, FL 32708
$650,00044 Days on yellowkey MLS ID: O6401349
REDUCED by $10,000 (1.5%) on 05/15/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 3046 Built: 2003Monthly Fee: $195 Tax: $7,948 (2025)Community: Avery ParkSingle Family
Taxes:$7,948
Remarks: Welcome to Avery Park! This is a STUNNING 4-bedroom, 2.5-bath residence that spans more than 3,000 SQUARE FEET, in the LOW MAINTENANCE community of Avery Park. Perfectly positioned on a CORNER LOT within a GATED enclave, this home offers an exceptional combination of sophistication, warmth, and nostalgic community charm. From the moment you arrive, the GRACIOUS FRONT PORCH, enhanced by FRESH LANDSCAPING (2026) and UPDATED RAILINGS (2025), sets a refined and inviting tone. Step through the DECORATIVE GLASS-PANELED ENTRY into a light-filled interior adorned with PLANTATION SHUTTERS throughout and rich ARCHITECTURAL DETAILING, creating an atmosphere that feels both elevated and welcoming. The formal Living and Dining Rooms offer elegant spaces for hosting, while the home gracefully transitions into a more relaxed yet equally impressive setting. The CHEF-INSPIRED KITCHEN is truly a centerpiece, beautifully updated with RESURFACED CABINETRY with NEW HARDWARE and PULL-OUT SHELVING (2024), glass-front accents, granite countertops, a sleek tile backsplash, stainless steel appliances (NEW REFRIGERATOR in 2025), a center island, breakfast bar, and pantry closet. The SUNLIT BREAKFAST NOOK, framed by sliding doors, invites you to enjoy morning coffee with views of the outdoor living space. The Family Room exudes comfort and style, featuring a TRAY CEILING and corner sliding doors that open to a paver patio within a PANORAMIC SCREENED ENCLOSURE, seamlessly blending indoor and outdoor living. The Primary Suite, thoughtfully located on the main level, is a true retreat, offering GENEROUS PROPORTIONS, a tray ceiling, abundant natural light, and a LUXURIOUS EN SUITE BATH complete with dual vanities, a soaking garden tub, a step-in shower, and a spacious walk-in closet. A well-appointed Laundry Room and stylish half bath complete the first floor. Upstairs, a SPACIOUS LOFT provides a versatile gathering space, perfect for a media room, game room, or additional lounge. Three additional bedrooms and a full bath offer comfort and flexibility for family or guests, with PROFESSIONALLY CLEANED CARPETING enhancing the move-in-ready appeal. This home is further elevated by an impressive list of updates, including NEW LUXURY VINYL PLANK FLOORING throughout the main floor (2025), FRESH INTERIOR PAINT (2025), EXTERIOR PAINT (2023), a NEWER ROOF (2020), UPDATED LIGHTING, and multiple AC SYSTEMS (2016 & 2018). The THREE-CAR GARAGE with built-in storage racks adds both practicality and visual appeal. Residents of Avery Park enjoy a vibrant lifestyle with AMAZING AMENITIES, including a sparkling community pool, playground, basketball court, gazebo, and a scenic pond with fountain, along with FREQUENT COMMUNITY EVENTS that foster a true sense of belonging. Ideally located near CENTRAL WINDS PARK and WINTER SPRINGS TOWN CENTER, this home offers easy access to shopping, dining, recreation, and everyday conveniences. Families will appreciate proximity to TOP-RATED SCHOOLS, while commuters benefit from NEARBY ACCESS to State Road 417, connecting you quickly to surrounding areas including Orlando. With its classic charm, modern updates, spacious layout, and EXCEPTIONAL LOCATION, this Avery Park home provides a lifestyle that is both elegant and welcoming—truly a place to feel at home. Act quickly—this GEM won't last long!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
50 SHEOAH BLVD #33, WINTER SPRINGS, FL 32708
$179,50033 Days on yellowkey MLS ID: O6404380
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 972 Built: 1973 Tax: $1,726 (2025)Community: Sheoah Sec 1Condo
Taxes:$1,726
Remarks: WELCOME HOME! This elegant, bright, and open first-floor, single-story 2-bedroom, 2-bath condo is located in the highly desirable Winter Springs community. From the moment you step inside, you’ll feel right at home in the spacious living and dining area featuring custom-built shelving and an inviting layout perfect for relaxing or entertaining. The split-bedroom floor plan offers added privacy, with sliding doors from the primary suite leading to a charming brick patio, ideal for enjoying your morning coffee or unwinding in the evening. The kitchen has been beautifully renovated with new appliances, updated countertops, and ample workspace. The primary bathroom features a walk-in shower with safety grab bars, while the guest bathroom includes a tub, with a convenient laundry area located in the guest bath closet. A bright and airy enclosed Florida room with A/C provides flexible space for a home office, reading nook, or additional living area. Step outside to your private patio with room for outdoor furniture, plants, or even your own garden retreat, all overlooking a peaceful wooded conservation area. Additional highlights include approximately 1,196 square feet including the enclosed porch, a newer A/C and water heater, fresh interior paint in a modern light gray, and no carpet throughout. Located in The Highlands, a quiet and friendly community offering a pool, tennis courts, parks, walking trails, scenic water views, reserved parking, and community mailboxes. HOA fees include high-speed internet, cable, pest control, and full grounds maintenance, with weekly lawn care and twice-weekly trash pickup. The home is situated in a top-rated school district with schools nearby and is just minutes from shopping, dining, and everyday conveniences. Schedule your private showing today, this one won’t last long!
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Fanny Stollmeyer (704-905-0698)
1281 NATURES WAY, WINTER SPRINGS, FL 32708
$1,200,00036 Days on yellowkey MLS ID: O6404018
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3212 Built: 1972 Tax: $2,240 (2024)Community: TuscawillaSpa: NoSingle Family
Taxes:$2,240
Remarks: Experience the beauty of city living on 2.3 acres in the highly desirable city of Winter Springs with no HOA—where open space, natural surroundings, and an equestrian friendly lifestyle come together. This unique property offers the freedom of rural living while remaining conveniently located near the Tuscawilla area. The fully usable acreage is ideal for horses, cattle, or other livestock. If livestock isn’t your preference, the expansive space is perfect for recreational vehicles, racing cars, or other outdoor hobbies. The 5 bedroom, 3 bath home is solid and ready for your personal updates. A standout feature is the 1,500 sq. ft. garage, offering ample room for a boat, race cars, or additional storage. This 2.3 acre parcel is one of the few remaining equestrian friendly properties in the city of Winter Springs, providing a rare combination of comfort, privacy, and natural surroundings. The home is zoned for highly rated Seminole County schools, offering the perfect blend of private country living and excellent educational opportunities. Seller motivated!
Listing is courtesy of: EQUITY REAL ESTATE BROKERS (407-252-5276)
Listing Agent: David Owji (407-252-5276)
30 SABLE CT, WINTER SPRINGS, FL 32708
$569,000113 Days on yellowkey MLS ID: O6382648
REDUCED by $10,000 (1.7%) on 04/12/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2674 Built: 1976 Tax: $3,043 (2024)Community: TuscawillaSpa: NoSingle Family
Taxes:$3,043
Remarks: REDUCED! Beautiful Executive 4 bedroom POOL home in Tuscawilla Country Club Golf Community! NO HOA! Mediterranean feel with wrought iron accents and courtyard. Huge Kitchen with island in the middle. All appliances. Hot water heater 2017. Lots of cabinet space. Spacious eat-in area beside kitchen. Formal Dining and Living rooms. Large bedrooms. Big Owners bedroom with walk-in closet and updated bath. Inside laundry room. Large Pool (updated to salt system) 8 feet deep. Big fenced yard. Screened in porch. Oversized 2 car side entrance garage (currently part of garage is an office but could easily be converted back). Community allows golf carts. Plenty of room to park jet skis, boats, and RV. Great location near shopping, restaurants, hospital, and major roads. Good schools. Country Club has golf, tennis, swimming, and dining membership. Trotwood park has basketball and tennis courts, soccer field, and covered picnic area. Many parks in neighborhood. Close to Seminole Trail for walking and bike riding. Move right in! Must Seee!
Listing is courtesy of: HOME SOLD NETWORK LLC (407-257-6223)
Listing Agent: Julie Bailey (407-257-6223)
10 MOREE LOOP #3, WINTER SPRINGS, FL 32708
$135,000115 Days on yellowkey MLS ID: O6381696
1 Days Off yellowkey (back on 5/8/2026)
REDUCED by $10,000 (6.9%) on 04/02/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1080 Built: 1973Monthly Fee: $413 Tax: $2,066 (2024)Community: Bay Tree Sec 10Condo
Taxes:$2,066
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. You will LOVE living in Baytree, a towhome styled condominium community in the desirable Highlands of Winter Springs! This home has been well loved and owned by the same owner for many years and is ready for YOU to make it YOURS. Offering a great floor plan and lots of space with a screen enclosed back porch and covered entry. Two large bedrooms on the 2nd floor and a convenient half bath on the first floor. Ample storage space! Appliances include NEW water heater (2026), washer/dryer, refrigerator, range and dishwasher! The Highlands community offers great amenities including a community pool, tennis/pickleball courts and walking trails! Located in Winter Springs and VERY close to Lake Mary, Maitland and major roads, shopping and dining. Ready to make your dreams of homeownership a reality? Schedule a tour today!
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Carla Stanton (321-356-3370)
510 SONATA CT, WINTER SPRINGS, FL 32708
$824,90039 Days on yellowkey MLS ID: O6402358
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
Elementary School: Sterling Park Elementary
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)
226 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708
$824,90050 Days on yellowkey MLS ID: O6398877
0 Days Off yellowkey (back on 5/30/2026)
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
Elementary School: Rainbow Elementary
Remarks: Under contract-accepting backup offers. 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 is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Colleen Kahl (407-630-0027)
1200 ROYAL OAK DR, WINTER SPRINGS, FL 32708
$499,99938 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)
330 HAYES RD, WINTER SPRINGS, FL 32708
$820,00033 Days on yellowkey MLS ID: O6404598
REDUCED by $20,000 (2.4%) on 05/25/2026
Bed: 4 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2252 Built: 1977 Tax: $2,738 (2024)Community: North Orlando Ranches Sec 04Single Family
Taxes:$2,738
Middle School: None
Remarks: Located on 2 acres with R-1AA zoning, this property offers space, flexibility, and privacy while still being conveniently close to everyday essentials. Ideal for those looking to keep horses, store equipment, or run a home-based business. The home features a bright, open layout with high ceilings, abundant natural light, and updated windows with plantation shutters. The remodeled kitchen includes updated cabinetry, granite countertops, stainless steel appliances, a wine fridge, and a large island with breakfast bar. The split floor plan offers a spacious primary suite with a custom walk-in closet and an updated bathroom with dual sinks and a walk-in shower, while three additional bedrooms feature new carpet, updated fixtures, and ample closet space. The secondary bathroom also provides direct access to the pool. Outdoor living is a highlight, with a covered and screened patio overlooking a heated saltwater pool, an extended paver deck, and a gazebo with a firepit area, perfect for entertaining. Recent updates include a roof (2020), AC (2019), and water heater (2025), along with a whole-home water treatment system. The property also features a detached 3-car garage/workshop with AC and potential for a guest house or in-law suite, a shed with AC and water ideal for an office or studio, and a metal pole barn for boat or RV storage. Dual EV charging stations are also installed. This property offers a unique combination of comfort, functionality, and zoning flexibility to fit a variety of lifestyles.
Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)
Listing Agent: Glendys Lorenzo Martinez (407-508-2808)
872 FALKIRK DR, WINTER SPRINGS, FL 32708
$438,997107 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)
120 E BAHAMA RD, WINTER SPRINGS, FL 32708
$1,249,000123 Days on yellowkey MLS ID: O6379165
REDUCED by $50,900 (3.9%) on 05/29/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 4464 Built: 1989 Tax: $12,488 (2025)Community: Bahama RanchesSpa: NoSingle Family
Taxes:$12,488
Remarks: Mid Century Modern Paradise!! A Beautiful, well-designed home with spectacular architecture offering privacy, space, and long-term versatility on a rare 2.22-acre lot with RV/Toy parking—delivering exceptional value in this area. A separate in-law or guest suite features its own exterior entrance and full bathroom, ideal for multigenerational living, a private office, studio, or extended stays. The main living areas are sprawling, thoughtfully arranged with strong natural light and a functional flow for everyday living and a large Loft for entertaining, office or hobbies. The large primary suite includes a spacious en-suite bath and walk-in closet. Bedrooms two and three are oversized, each with walk-in closets; one includes a hidden play loft/ adventure nook accessible through the Narnia style closet access. The expansive property also includes a detached casita in the backyard, currently used as a workshop, with clear potential to be converted into a guest home, rental unit, or Airbnb. Located on a quiet street in an established Winter Springs neighborhood, with convenient access to top-rated schools, shopping, dining, and major commuter routes. Concessions considered with the right scenario. Buyer and buyer’s agent to verify all information. Both owners are licensed real estate agents.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alma Merrill (801-613-8090)
140 N. FAIRFAX, WINTER SPRINGS, FL 32708
$325,000185 Days on yellowkey MLS ID: O6364352
REDUCED by $6,000 (1.8%) on 04/24/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1188 Built: 1959 Tax: $2,426 (2024)Community: North OrlandoSingle Family
Taxes:$2,426
Remarks: Fully Renovated Winter Springs Home with No HOA – Move-In Ready in Seminole County Welcome to 140 N. Fairfax Avenue in Winter Springs, Florida, a beautifully renovated home that blends classic Florida charm with modern upgrades in one of Seminole County’s most desirable and convenient locations. This extensively updated 3-bedroom, 1-bath home sits on a generous 8,900-square-foot lot and offers a turnkey opportunity for first-time buyers, downsizers, or investors seeking a move-in ready property in the Orlando metro area. Inside, the home has been thoughtfully remodeled from top to bottom. The interior features new flooring, fresh paint, modern lighting, and a completely updated kitchen and bathroom, along with new appliances and updated mechanical systems. A brand-new HVAC system installed in late 2025 and new energy-efficient windows add comfort and efficiency, allowing the next owner to enjoy years of low-maintenance living. The open and functional layout provides comfortable everyday living while maximizing natural light throughout the home. Outside, the spacious yard offers plenty of room to create your ideal outdoor living space. With no HOA restrictions, homeowners have the flexibility to add a garage or workshop, store a boat or trailer, or design additional outdoor entertaining areas. The property’s generous lot size offers rare freedom and versatility that is increasingly hard to find in Central Florida. For outdoor recreation, the home is located just a short walk to Torcaso Park, featuring a playground, splash pad, soccer fields, and a fishing pier. Residents also enjoy close proximity to Lake Jesup, Spring Hammock Preserve, and the Cross Seminole Trail, one of the region’s most popular trails for biking, jogging, and scenic walks. Families benefit from access to highly regarded Seminole County Public Schools, including Highlands Elementary School, Indian Trails Middle School, and Winter Springs High School, all located within a short drive of the home. Convenience is another major highlight of this location. The home is just minutes from Winter Springs Town Center, Oviedo on the Park, and Winter Park, providing easy access to shopping, dining, entertainment, and everyday services. Healthcare facilities such as Orlando Health South Seminole Hospital and AdventHealth Altamonte Springs are also nearby, offering quick access to medical care. Public transportation options are available throughout the area via the LYNX regional bus system, which serves Seminole County and connects residents to destinations across the greater Orlando area. Commuters can also access nearby SunRail stations in Longwood and Altamonte Springs for convenient rail service into downtown Orlando and surrounding employment centers. Safety and emergency services are close by as well, including Seminole County Fire Department stations serving the Winter Springs area, providing quick response coverage for local residents. Winter Springs itself is consistently recognized as one of the best places to live in Central Florida, known for its community feel, parks, trails, and easy access to major employers throughout Orlando, Lake Mary, and the Seminole County tech corridor. Whether you’re searching for a move-in ready home, an investment property, or an affordable Central Florida residence close to parks, schools, and commuter routes, 140 N. Fairfax Avenue delivers comfort, flexibility, and location in one exceptional package.
Listing is courtesy of: ERA GRIZZARD REAL ESTATE (407-203-5800)
Listing Agent: Shawn Mccormick (321-439-4277)
328 SAN MIGUEL ST #328, WINTER SPRINGS, FL 32708
$224,900137 Days on yellowkey MLS ID: O6375171
1 Days Off yellowkey (back on 4/29/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1032 Built: 1980Monthly Fee: $135 Tax: $2,102 (2025)Community: Indian RidgeCondo
Taxes:$2,102
Remarks: Under contract-accepting backup offers. Welcome home to this charming 3-bedroom, 2-bathroom home, which offers 1,032 square feet of beautifully updated living space. This property features a newly painted interior and a fully remodeled eat-in kitchen equipped with brand-new stainless steel appliances, shaker cabinets with modern hardware, a trendy backsplash, and granite countertops. The home is designed with a functional split-floor plan for added privacy. The master suite includes a private bathroom with a new vanity, lighted mirror, and updated lighting. On the opposite side of the home, you will find two additional bedrooms and a second bathroom, which also features a new vanity and modern lighting fixtures. The layout includes separate living and dining rooms, with brand-new ceiling fans installed in the living area and all bedrooms. Major high-ticket maintenance items have been recently addressed, including a new roof installed in 2025, a new hot water heater in 2023, and an HVAC system from 2018 with air ducts replaced in 2020. Exterior features include a private patio with a storage shed, and residents can enjoy a low monthly HOA fee that provides access to a community pool and tennis courts. Located conveniently near schools, major highways, medical centers, and prime shopping and dining, this home is an ideal choice for a growing family or a strategic investment opportunity.
Listing is courtesy of: REALTY TECH INC (407-332-9757)
Listing Agent: Carmen Vazquez (407-617-9045)
268 TAVESTOCK LOOP, WINTER SPRINGS, FL 32708
$569,90023 Days on yellowkey MLS ID: O6407307
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2415 Built: 2001Monthly Fee: $150 Tax: $4,293 (2025)Community: ParkstoneSingle Family
Taxes:$4,293
Remarks: PHOTOS COMING SOON**268 Tavestock Loop, Winter Springs, FL 32708** Perfectly situated in the heart of Winter Springs, this stunning 4-bedroom, 2.5-bathroom home offers the ideal location with easy access to shopping, dining, theme parks, major roads, and the airport. Nestled within a desirable gated community, you'll enjoy peace of mind along with fantastic amenities including a community Lake Jess Up, pool, park, and 2 playground walking path, community benches. Step inside this beautiful two-story home and immediately notice the high ceilings that create a bright, open atmosphere throughout. Hard flooring runs seamlessly from room to room, giving the entire 2,883 square feet a clean, modern feel that is both stylish and easy to maintain. The kitchen is equipped with sleek stainless steel appliances, making it the perfect space to prepare meals and gather with family and friends. With four spacious bedrooms, there is plenty of room for everyone. The primary bedroom offers a comfortable retreat after a long day, while the additional bedrooms provide flexible space for family, guests, or a home office. Two full and half bathroom ensure convenience for the entire household. This move-in ready home means no waiting and no hassle. Simply unpack and start enjoying everything this wonderful property and community have for you. Whether you are relaxing by the community pool, taking the family to the playground, walking trails, Lake Jess Up or exploring all that Central Florida has in store, this home puts it all within reach. Don't miss your chance to make 268 Tavestock Loop your new home. Schedule your private showing today!
Listing is courtesy of: FUSILIER REALTY GROUP (407-476-0476)
Listing Agent: Zep Bholai-Lawrence (321-689-3467)
1444 BIRD RD, WINTER SPRINGS, FL 32708
$838,500263 Days on yellowkey MLS ID: O6344113
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2350 Built: 1977 Tax: $2,076 (2024)Community: Watts FarmsSingle Family
Taxes:$2,076
Remarks: One or more photo(s) has been virtually staged. ONE OF A KIND! Stunning Renovated Lakefront Home on Private Peninsula – Welcome to your fully reimagined lakefront retreat at 1444 Bird Road in the heart of Winter Springs. Nestled along the serene shores of Lake Tony, this highly detailed, professionally rehabbed home blends modern luxury with timeless Florida charm. From the moment you arrive, you’ll notice the thoughtful craftsmanship and attention to detail throughout. The home has been completely renovated from top to bottom, featuring a bright, open-concept layout with abundant natural light and stunning lake views from multiple living spaces. The designer kitchen is a true centerpiece, showcasing amazing cabinetry, premium quartz countertops, stainless steel appliances, and a spacious island perfect for entertaining. The living and dining areas flow seamlessly, creating an inviting space for gatherings or quiet evenings overlooking the water. Retreat to the primary suite, where you’ll find a spa-inspired bathroom with high-end finishes, elegant tile work, and a relaxing atmosphere designed for comfort. Additional bedrooms offer flexibility for guests, family, or a home office. Step outside to your private backyard oasis, where you can enjoy peaceful mornings or breathtaking sunsets on Lake Tony. Whether you’re kayaking, fishing, or simply unwinding by the water, this property offers the ultimate lakefront lifestyle. Additional upgrades include updated systems, modern fixtures, and quality finishes throughout—providing peace of mind and move-in-ready convenience. Located in a desirable Winter Springs neighborhood with easy access to top-rated schools, parks, shopping, and dining, this home is a rare opportunity to own a turnkey lakefront property. Don’t miss your chance to experience luxury living on Lake Tony—schedule your private showing today.
Listing is courtesy of: KEEN REALTY GROUP, INC. (407-699-2127)
Listing Agent: Bobby Keen (407-951-2300)
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