Location: Winter Springs
Do Not Show Listings
649 DAVID ST, WINTER SPRINGS, FL 32708
$265,00050 Days on yellowkey MLS ID: O6395999
0 Days Off yellowkey (back on 5/2/2026)
Bed: 3 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1077 Built: 1971 Tax: $3,074 (2025)Community: North Orlando Townsite 4Th Add RepSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,074
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome home! This 3-bedroom, 1-bathroom single-family Winter Springs home is move-in ready with tons of upgrades! All the mechanicals have been updated or replaced: Roof replacement in 2024, new plumbing (complete repipe) 2023, AC unit replaced in 2023, and a new electrical panel in 2026. The Kitchen and Bathroom have both been updated, with all-new kitchen appliances. All this with no HOA and a super affordable price for solid block construction in this zip code! We have priced the home to move fast. Schedule your showing now!
Listing is courtesy of: BUSBY REALTY LLC (407-529-6952)
Listing Agent: Chad Busby (407-529-6952)
936 TORREY PINE DR, WINTER SPRINGS, FL 32708
$420,00051 Days on yellowkey MLS ID: O6386843
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1678 Built: 2000Monthly Fee: $126 Tax: $2,652 (2024)Community: Greenbriar Sub Ph 2Single Family
Taxes:$2,652
Elementary School: Rainbow Elementary
High School: Winter Springs High
Tax Year: 2024
Middle School: Indian Trails Middle
Remarks: Under contract-accepting backup offers. GOLF FRONT HOME IN TUSCAWILLA! Beautiful views and an open floor plan with updates galore make this one THE one! With lawncare, swimming pool and friendly neighbors included in the HOA, easy living is yours! Note: this home was built as a 3 bedroom, yet the previous owner converted the space to a 2 bedroom that can easily be converted back. You will adore the beautifully updated kitchen featuring a stunning glass backsplash, gorgeous granite countertops, custom pantry and stainless steel appliances. The open layout flows seamlessly through the front door to the living/dining space with a custom pass through to the kitchen that is wide open to the family room. From the kitchen, family room, primary suite, and all-weather porch, you can enjoy relaxing views of the 16th fairway on the Championship Tuscawilla Golf Course. Amazing assumable LOW interest financing is available to a qualified buyer. Full details are available. A spacious primary suite featuring a large walk-in closet with custom closet system and separate access to the rear porch. Fall in love with the handsome updated ensuite bath with spacious built in vanity, glass enclosed tiled walk in shower plus additional storage or vanity space where a bathtub was removed. Additional features and upgrades include new double pane sliding doors to the glass/ screened enclosed patio, ……… The brick paved driveway and spacious 2-car garage will keep your vehicles happy, while the recent updates and community amenities will make you very happy! As an option, Tuscawilla Country Club offers dining, exercise facility, junior Olympic pool, tennis courts and leagues, pickleball, golf and social events. Don't miss out on this great property! Visit today!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Colleen Kahl (407-630-0027)
684 OLEAN CT, WINTER SPRINGS, FL 32708
$849,90035 Days on yellowkey MLS ID: O6399510
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2832 Built: 1988Monthly Fee: $8 Tax: $8,448 (2025)Community: Chelsea WoodsSpa: NoSingle Family
Taxes:$8,448
Elementary School: Lawton Elementary
High School: Oviedo High
Remarks: Walk on it and call it home! This amazingly cared for POOL home with 3 Car Garage in Chelsea Woods, Tuscawilla is ready for its new owner! With nearly 3,000 square feet, this spacious 5-bedroom, 4-bathroom home sits on over one-third of an acre and offers the perfect blend of comfort, functionality, and Florida living. As you step inside, you’re greeted by an open and inviting family room with stunning views of the pool, seamlessly connected to the dining area. A bonus: the pool table stays and can double as a dining table for entertaining! To the left of the entry, you’ll find a generously sized primary suite along with an additional bedroom and full bathroom—ideal for guests or a home office setup. The heart of the home is the expansive kitchen, featuring ample space, a cozy kitchenette, and a wet bar—perfect for hosting. The adjoining living room showcases a beautiful fireplace, adding warmth and charm to the space. As you will notice, this home is very LIGHT AND BRIGHT and features NO CARPET! Toward the back of the home are three additional bedrooms and two full bathrooms, including one with a private ensuite—perfect for multi-generational living or added privacy. Step outside to your fully fenced backyard oasis, complete with a screened-in, heated saltwater pool and lanai—ideal for year-round enjoyment. Major updates include a NEW ROOF (2023) and newer AC units (2023 & 2016), offering peace of mind for years to come. Located in the sought-after Tuscawilla area, Chelsea Woods offers optional HOA and convenient access to top-rated schools, Tuscawilla Country Club, SR-417, Seminole Trail, Seminole State College, UCF, Lockheed Martin, and Siemens. This exceptional home won’t last long—schedule your private showing today before this home is SOLD!
Listing is courtesy of: VOSS REALTY INC (407-456-0777)
Listing Agent: Lindsay Kaye Voss (407-456-0777)
1513 BLACK BEAR CT, WINTER SPRINGS, FL 32708
$1,479,50078 Days on yellowkey MLS ID: O6385058
REDUCED by $69,500 (4.5%) on 04/16/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 6175 Built: 1989Monthly Fee: $142 Tax: $23,523 (2025)Community: Bear Creek EstatesSingle Family
Taxes:$23,523
Elementary School: Keeth Elementary
Remarks: Welcome to this exceptional home in the exclusive gated community of Bear Creek Estates, set on over an acre of lush wooded greenbelt with beautiful landscaping and a circular driveway that creates outstanding curb appeal. The over 6,000 sq. ft. (includes 1 car garage/hobby room of approx. 280 sq.ft.) home features a new architectural tile roof (less than one year old) and 10-foot ceilings throughout the first floor, creating a bright and spacious feel. Inside, you’ll find elegant formal living and dining spaces, a private home office, and a comfortable family room overlooking the sparkling pool and lanai. The home offers oversized secondary bedrooms with seating areas, plus a large additional bedroom that can serve as an office, art studio or flex space. Entertainment is exceptional with two theater spaces, The main floor home theater is projector-ready, with acoustic panels, granite snack counter, an electronic masking screen and wiring for 7.1 sound. The upstairs primary bedroom is massive in size and the ideal retreat to unwind at end of the day! Complete with its sitting area and outdoor deck with stunning panoramic views of lush nature. The upstairs primary suite in this home also includes a projector drop-down screen and wiring for 5.1 sound. The private backyard retreat features a beautiful pool with LED lighting, waterfall feature, and updated pump and filter (2023), along with panoramic views of lush green space. Additional highlights include a smart audio system controlled by smartphone app, extensive network wiring, pre-wiring for security cameras, well-fed irrigation, and a backyard telescope pier with power and ethernet. In Winter Springs, this home offers peaceful luxury living while being close to shopping, dining and major commuting routes.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Lynda Miller (407-620-2924)
1281 NATURES WAY, WINTER SPRINGS, FL 32708
$1,200,00021 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)
4910 E LAKE DR, WINTER SPRINGS, FL 32708
$2,399,00021 Days on yellowkey MLS ID: O6398929
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3657 Built: 1964 Tax: $6,256 (2024)Community: NaSingle Family
Taxes:$6,256
Elementary School: Sterling Park Elementary
Middle School: South Seminole Middle
Remarks: A truly rare find in Winter Springs. This equestrian-friendly, lakefront estate is complete with its own private tennis court, a solid block-constructed horse barn, and room to enjoy every part of the lifestyle. All of this, tucked in a quiet setting that keeps you close to the heart of Orlando, with the added benefit of being just 2 miles from The Geneva School, one of the area’s premier private education options. Originally built in 1964, the home was thoughtfully expanded in 1994, creating a larger, more functional layout while preserving its character. Today it offers over 3,000 SF overlooking the shimmering waters of Little Lake Howell. Enjoy west-facing sunset views framed by mature cypress trees. Host friends for tennis or pickleball right in your backyard. The sizeable horse barn was engineered for exceptional durability, built with block construction and poured concrete for maximum strength. The main home includes a 3-car garage, and the barn adds an oversized carport that can easily double as covered boat storage.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Kris Kennedy (813-947-3509)
421 RINGWOOD CIR, WINTER SPRINGS, FL 32708
$500,00050 Days on yellowkey MLS ID: V4948285
0 Days Off yellowkey (back on 5/1/2026)
REDUCED by $7,000 (1.4%) on 04/25/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2029 Built: 1984Monthly Fee: $23 Tax: $5,298 (2024)Community: Deer Run Unit 21BSingle Family
Taxes:$5,298
Remarks: Under contract-accepting backup offers. Welcome to this spacious and inviting 4-bedroom, 2-bath pool home in the heart of Winter Springs. Thoughtfully designed for both everyday living and entertaining, this home offers a comfortable layout with generous living spaces and plenty of room for a growing family. The backyard is a true highlight, featuring a private pool and brand-new sod that creates a fresh, vibrant outdoor setting perfect for relaxing, hosting gatherings, or enjoying Florida sunshine year-round. Inside, you will find a well-maintained home with important updates already completed, including a roof replaced in 2017, A/C replaced in 2021, and plumbing updated in 2021, offering peace of mind for the next owner. Conveniently located near shopping, dining, parks, and top-rated schools, this property combines comfort, function, and lifestyle in one desirable package.
Listing is courtesy of: LPT REALTY LLC (386-388-7877)
Listing Agent: Farrah Thacker (386-216-7099)
709 SAILFISH RD, WINTER SPRINGS, FL 32708
$407,500169 Days on yellowkey MLS ID: O6364715
REDUCED by $5,000 (1.2%) on 05/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1737 Built: 1984 Tax: $5,463 (2024)Community: North Orlando Ranches Sec 10Spa: NoSingle Family
Taxes:$5,463
Elementary School: Layer Elementary
Remarks: Some neighborhoods offer just a house; this one delivers a true Florida lifestyle, anchored by a beautiful, deep quarter-acre lot and a home built for functional, everyday living. Tucked away in a quiet pocket of Winter Springs—one of Seminole County’s most coveted and safest communities—this 3-bedroom, 2-bathroom gem offers the rare freedom of no HOA combined with unparalleled privacy. The home provides immediate peace of mind with a roof that is only 5 years old. Set beneath a picturesque canopy of mature trees and draping Spanish moss, the curb appeal speaks to the established, friendly vibe that residents of Winter Springs enjoy. Step inside to a flexible layout built for flow, featuring dedicated living and family rooms that give everyone room to spread out. The central kitchen and dining space is positioned perfectly to serve both entertaining areas and acts as the heart of the home. The smart split-bedroom floor plan provides ideal separation, tucking the spacious primary suite on one side of the house for privacy and tranquility. The real magic happens where the indoors meets the outdoors. The home expands dramatically with a large, enclosed Florida Room (22'6" x 11'6") that is fully under A/C with its own dedicated mini-split unit—making this substantial bonus space a year-round extension of the living area, perfect for an office, gym, or sun-soaked den. This room leads directly out to a private, spacious backyard where you will enjoy the unique benefit of no rear neighbors, secured by a perimeter of mature trees and fencing. Even the garage has been elevated: the two-car garage features durable epoxy flooring and includes a dedicated laundry area and a useful closet room, perfect for home projects or tool storage. The location is the final mic drop. You are moments from the convenience of Winter Springs Town Center, Central Winds Park, and the premier amenities of the Tuscawilla area. You are also zoned for the excellent Seminole County School District. You get the quiet, safe suburban environment while maintaining effortless access to major highways (417/I-4) for a convenient commute to Downtown Orlando or Lake Mary. View the 3D Matterport tour now to fully appreciate the space and layout. This is more than a listing—it’s the home where your next chapter begins.
Listing is courtesy of: ELEGANT REALTY LLC (407-985-2840)
Listing Agent: Wayne Mottley (407-741-3804)
632 TUSKAWILLA POINT LN, WINTER SPRINGS, FL 32708
$450,00049 Days on yellowkey MLS ID: O6394544
REDUCED by $20,000 (4.3%) on 04/19/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1917 Built: 1980Monthly Fee: $44 Tax: $1,888 (2025)Community: Tuskawilla PointSpa: NoSingle Family
Taxes:$1,888
Elementary School: Red Bug Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Under contract-accepting backup offers. Located in the Tuskawilla area of Winter Springs, this 4-bedroom, 2-bath home with 1,917 square feet sits on a quiet, tree-lined street. The layout includes multiple living areas, with a family room centered around a wood-burning brick fireplace, along with separate living and dining spaces. A garden window highlights the breakfast nook and brings in natural light. The primary suite and additional bedrooms offer flexible space for everyday living, guests, or a home office. The home may benefit from updates to areas such as the flooring, kitchen, and bathrooms, providing an opportunity for a new owner to make changes over time and tailor the space to their preferences. The backyard includes a screened-in patio and pool, along with a fenced yard. Several major components have been updated, including the roof (2017), pool resurfacing (2019), garage door and motor (2019), HVAC (2014), dishwasher (2024), washer & dryer (2024), microwave (2025), and pool screens (2025). The property is located near Seminole County schools, parks, shopping, dining, and major roadways, offering convenient access to daily needs and surrounding areas. This home may be a good fit for buyers looking for space, location, and the ability to make updates over time.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Harry Narvaez-Mercado (407-490-8838)
207 TAVESTOCK LOOP, WINTER SPRINGS, FL 32708
$519,00028 Days on yellowkey MLS ID: O6401946
0 Days Off yellowkey (back on 4/27/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2139 Built: 2001Monthly Fee: $150 Tax: $5,151 (2024)Community: ParkstoneSingle Family
Taxes:$5,151
Remarks: Under contract-accepting backup offers. SELLER IS CALLING FOR HIGHEST AND BEST BY SATURDAY AT 6:00 PM. Some homes you walk into and just know. Step through the foyer into soaring ceilings, arched windows, and a bright open layout that pulls natural light from every direction. The remodeled kitchen is the anchor of the home: quartz counters, crisp white cabinetry, stainless appliances, a walk-in pantry, and a long island that opens directly to the family room so whoever is cooking stays in the conversation. A breakfast nook sits just off the kitchen with sliders leading out to the covered lanai, and a formal dining area flows seamlessly into a separate living space toward the front of the home. The split layout puts the primary suite at the back of the home for maximum privacy, with a walk-in closet and an updated spa-style bath featuring a freestanding soaking tub, oversized walk-in shower with rain head, and dual vanities. Two additional bedrooms share a hall bath in the center of the home. At the front of the home, a fourth bedroom has its own walk-in closet and private full bath, ideal for overnight guests. Out back, a screened-in, covered lanai plus an open porch stretch across the rear of the home, looking over a fenced yard with mature trees and room to play, garden, or add a pool. Parkstone is the largest gated community in Winter Springs, tucked along the south shore of Lake Jesup. Residents get a community pool, tennis and volleyball courts, two playgrounds, walking trails, and a fishing dock on the lake. The HOA includes full lawn maintenance, so weekends are yours. Winter Springs High School is within walking distance, and the home is zoned for sought-after Layer Elementary and Indian Trails Middle, all part of the top-rated Seminole County school district. Location puts you minutes from the Winter Springs Town Center for shopping and dining, Central Winds Park for sports fields and seasonal festivals, and the Cross Seminole Trail for miles of biking and running. SR 434 is at the community entrance and the 417 Greeneway is a quick drive, making UCF, Oviedo, Sanford, and downtown Orlando an easy commute. The beaches and the theme parks are both under an hour away. Gated, updated, move-in ready, and zoned for the schools everyone is asking about. This one checks the boxes.
Listing is courtesy of: EXP REALTY LLC (407-305-4300)
Listing Agent: Tony Ubaldini (407-242-6781)
807 BUCKIE DR, WINTER SPRINGS, FL 32708
$375,00023 Days on yellowkey MLS ID: O6386108
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1574 Built: 1978Monthly Fee: $35 Tax: $4,487 (2025)Community: Highlands Sec 1Single Family
Taxes:$4,487
Remarks: Move Right In this Updated Highlands Home! Desirable Gas Stove in Kitchen along with newer Appliances & Granite Countertops, New Bathroom Vanities New Roof 2024. Large Fenced Yard, Fireplace & Inside Laundry Room. The Highlands has a Large Community Pool, Playgrounds, Clubhouse with BBQ Area, Audibon Park, Tennis & Pickleball Courts & Nature Walking Trails. Highly rated Seminole County Schools.
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)
Listing Agent: Paul Buscemi (407-716-2874)
270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$259,000191 Days on yellowkey MLS ID: O6359666
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1089 Built: 1994Monthly Fee: $121 Tax: $327 (2024)Community: Deersong 2Spa: NoSingle Family
Taxes:$327
Remarks: Price Improvement to $259,000 * Quick Closing Available. Welcome to 270 San Gabriel Street in Winter Springs—now offered at an updated price and ready for its next owner. This well-maintained, single-story home features vaulted ceilings and a bright, open layout that creates a comfortable and inviting living space. With neutral finishes and ceramic tile flooring throughout, the home is truly move-in ready. All appliances are included for added convenience. Enjoy morning coffee or unwind in the evening on the oversized screened patio, offering a private outdoor retreat. Additional exterior storage provides practical space for bikes, tools, and seasonal items. Located just minutes from the scenic Cross Seminole Trail, the Deersong community also offers access to a pool and cabana for residents to enjoy. Nearby parks, shopping, dining, and top-rated Seminole County schools add to the home’s appeal. Considering making a move to downsize? First-time homebuyer? investor? or seeking a low-maintenance second home in Central Florida? Schedule your private showing today. With a newly reduced price and quick closing available, this is an excellent opportunity to own a well-cared-for home in a desirable location..
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Alie Gattis (407-760-1488)
515 SEASONS CT, WINTER SPRINGS, FL 32708
$299,900254 Days on yellowkey MLS ID: O6343009
1 Days Off yellowkey (back on 4/30/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1101 Built: 1996Monthly Fee: $120 Tax: $3,258 (2024)Community: Seasons TheSingle Family
Taxes:$3,258
Elementary School: Winter Springs Elementary
Remarks: Under contract-accepting backup offers. **One or more photo(s) has been virtually staged**.Move-In Ready Home – Fully Updated Inside and Out! Simply bring your personal belongings — this 3-bedroom, 2-bathroom home is ready for immediate occupancy. Freshly painted throughout, it features many upgrades and improvements, including roof (2021), water heater (2020), indoor A/C unit (2018), and outdoor A/C unit (2025). The remodeled kitchen showcases brand-new wood cabinets, granite countertops, stainless steel appliances. Both bathrooms have been completely renovated with modern showers, new toilets, stylish vanities, and new plumbing fixtures. All interior doors have been replaced for a refreshed, contemporary look. The home offers waterproof luxury vinyl plank flooring in a warm Birchwood tone, accented by new baseboards throughout. The private backyard features synthetic turf, providing a lush, green appearance year-round with minimal maintenance. The monthly HOA fee of $120 includes front yard lawn service, and there is an additional annual HOA fee paid once per year. This property combines modern upgrades, low maintenance, and move-in convenience — a perfect choice for buyers seeking comfort and quality. Located in the sought-after area of Winter Springs, known for its top-rated schools. Community featuring a swimming pool, tennis courts, and a playground, perfect for an active lifestyle. Don’t miss out — book your showing today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Olga Carballea Diaz (407-508-9848)
1054 WINDING WATERS CIR, WINTER SPRINGS, FL 32708
$559,90037 Days on yellowkey MLS ID: O6398229
REDUCED by $10,000 (1.8%) on 04/29/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2321 Built: 1998Monthly Fee: $42 Tax: $4,167 (2025)Community: Winding HollowSpa: YesSingle Family
Taxes:$4,167
Remarks: This beautiful 4-bedroom, 3-bath, one-story pool home offers over 2,300 sqft of living space on a premium conservation lot with no rear neighbors, providing privacy and a peaceful setting. Now priced at $559,900 after a $10,000 price improvement. Major updates already completed: roof 2019, AC updated 2020–2021, pool resurfaced 2022, and kitchen updated 2022. Solar panels will be paid off at closing, giving the new owner added value and energy efficiency. The home features a spacious split floor plan with high ceilings and abundant natural light. Formal living and dining areas flow into a large family room with a wood-burning fireplace, connecting seamlessly to the kitchen and outdoor space. The kitchen offers ample cabinet space, updated finishes, and includes stainless steel appliances: range, refrigerator, dishwasher, and microwave. Washer and dryer are also included. The primary suite is oversized with a large en-suite bathroom featuring dual sinks, soaking tub, separate shower, and a spacious walk-in closet. Secondary bathrooms are well maintained with potential for future personalization. Flooring includes tile, laminate/engineered flooring, and carpet in select areas. Additional features include an indoor laundry room and a 2-car garage with extra storage. Step outside to a screened-in pool and covered patio, ideal for Florida living year-round. The backyard backs to conservation, offering privacy and no rear neighbors. Situated on one of the larger lots in the neighborhood and directly across from a park and schools, this is a prime location close to shopping, dining, and major highways. Approximately 25–30 minutes to Downtown Orlando, 20–25 minutes to UCF, and about 45–60 minutes to the beaches. Zoned for top-rated Seminole County schools. Homes in this area with similar features and updates have sold in higher ranges, making this a strong opportunity.
Listing Agent: Alexa Monasterio Flores (786-915-9294)
337 KIRKCALDY DR, WINTER SPRINGS, FL 32708
$284,900111 Days on yellowkey MLS ID: O6375532
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 974 Built: 1984Monthly Fee: $6 Tax: $1,428 (2024)Community: Highland Village 1Single Family
Taxes:$1,428
Remarks: Warm and inviting home located in the highly sought-after Highland Village community of Winter Springs—where residents love to live and rarely want to leave. This 2-bedroom, 2-bath home features an open floor plan, abundant natural light, and no carpet throughout. The spacious living and dining areas open a comfortable layout, perfect for everyday living or entertaining. The primary bedroom is generously sized with a large walk-in closet, and the primary bathroom has been updated with a sink, faucet and mirror. The secondary bedroom is also well-sized and versatile. The guest bathroom has been updated with a new vanity and mirror. The kitchen offers ample storage, includes all appliances, and opens directly to the private backyard—complete with a covered patio and ceiling fan, ideal for relaxing outdoors. Seller has recently updated the following: replace all interior doors, all new faux window blinds for all windows and crown molding in living areas. All appliances will stay including the washer and dryer! Enjoy living in a vibrant, well-maintained community with top-rated schools and fantastic amenities including a pool, tennis and pickleball courts, volleyball court, playground, and scenic walking trails and low HOA costs. Conveniently located near SR 434 and Tuskawilla Road, just minutes from Winter Springs Town Center, shopping, dining, and a short walk to Torcaso Park. Schedule your private showing today.
Listing Agent: Dan Goodman (407-212-1012)
314 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$279,990224 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)
1692 WINGSPAN WAY, WINTER SPRINGS, FL 32708
$865,00064 Days on yellowkey MLS ID: O6390916
1 Days Off yellowkey (back on 4/26/2026)
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2660 Built: 1990Monthly Fee: $48 Tax: $5,093 (2024)Community: Glen Eagle Unit 2Spa: NoSingle Family
Taxes:$5,093
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Nestled within the prestigious Glen Eagle community of Tuscawilla, this exceptional executive-style single-story custom home offers luxury, space, and an unbeatable location. Set along picturesque tree-lined streets, this 5-bedroom, 3.5-bath residence with a 3-car side-entry garage and additional gated parking (perfect for a boat) is designed for both comfortable living and effortless entertaining. From the moment you arrive, you’ll appreciate the freshly painted exterior (2025) and stunning new double entry doors, setting the tone for the quality and upgrades found throughout. Recent Upgrades Include: Brand new roof with 4 skylights over the covered patio (2025), Seven new sliding glass doors ($37,000) (2025), New front entry, garage, and service doors (2025), Two newer garage doors (approx. 2 years), Updated primary bathroom with quartz counters, seamless glass shower, and new cabinetry (2025), Replumbed (2015), Water heater (2023), Lennox 5-ton HVAC system with electric static filter & UV light (2020), LED ceiling lighting throughout. Step inside to a welcoming foyer that opens to formal living and dining rooms, creating an elegant first impression. The thoughtfully designed 3-way split floor plan ensures privacy and flexibility for any lifestyle. The primary suite spans the entire left wing of the home, offering a true retreat with a wall of brand-new sliding glass doors opening to the pool and covered patio. Enjoy tray ceilings, a spacious sitting area, and en-suite bath featuring marble flooring, new vanity with quartz countertop, a jetted tub, new seamless glass shower door, two walk-in closets and a large linen closet. At the heart of the home, the kitchen, designed by S & W Kitchens, features granite countertops, stainless steel appliances, a breakfast bar, built-in desk, wet bar, and a generous nook for casual dining. The kitchen flows seamlessly into the family room, highlighted by a marble wood-burning fireplace, custom built-ins, shutters, and a Bose sound system. The additional bedrooms are thoughtfully arranged: Three bedrooms and two full baths off the family room, including a Jack-and-Jill layout. Bedrooms 2 & 3 share the jack & jill bath with tub. Bedroom 4 can use the hallway bath which features a walk-in shower, granite counter, dual sinks, plenty of cabinets and also serves as a pool bath. A separate 5th bedroom with its own private sliding door entry—ideal for a home office, guest suite, or flex space. A convenient half bath for guests Step outside to your private backyard oasis featuring a screened-in pool with travertine deck, expansive covered lanai with four skylights, and a wet bar—perfect for year-round entertaining. The fully fenced yard adds privacy and functionality. Located in the heart of Tuscawilla, this home is zoned for top-rated Seminole County schools and offers convenient access to 417, 426, and 434, as well as UCF, Siemens, Research Park, YMCA, Oviedo Medical Center, Oviedo Mall and Oviedo on the Park. Enjoy nearby parks, the 29-mile Seminole Trail, and optional memberships at Tuscawilla Country Club for golf, tennis, swimming, and social activities. Plenty of nearby restaurants and shopping. This home truly offers the perfect blend of space, comfort, and elevated Florida living
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Suzanne Giambruno (407-765-6495)
1444 BIRD RD, WINTER SPRINGS, FL 32708
$838,500248 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)
104 REDTAIL PL, WINTER SPRINGS, FL 32708
$469,900110 Days on yellowkey MLS ID: O6378697
0 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1766 Built: 1995Monthly Fee: $170 Tax: $2,250 (2024)Community: Eagles Watch Ph 1Single Family
Taxes:$2,250
Remarks: Under contract-accepting backup offers. RECENTLY PRICE REDUCED! Luxury Living Meets Trailside Adventure — with Everything Close By! WELCOME TO THE GATED COMMUNITY OF EAGLE WATCH! This beautifully presented property is a 3-bedroom, 2-bath home where comfort, style, and location come together effortlessly. It is located in the cherished well-maintained community in Winter Springs. Enjoy peace of mind with a newer roof and HVAC system, luxury engineered wood flooring throughout the home, plus fresh interior paint that gives the home a clean, modern feel. Low HOA fees also include common area landscaping maintenance and pristine curb appeal throughout the community! Eagle Watch shares a gated entrance community pool with Howell Creek Reserve to enjoy with friends and family! The home's inviting layout is perfect for everyday living and entertaining, filled with natural light and an easy, modern flow. Step outside and relax with your covered screened in porch and level up your lifestyle with direct access to the Cross Seminole Trail—a dream for avid bicyclists, hikers, and walkers who love the outdoors. Now let's talk about the location being so convenient! You’re just minutes from malls, dining, and shopping, close to SR 417, University of Central Florida, and an easy ride to the world-class parks Orlando is famous for. Adventure, entertainment, and everyday essentials are all right at your fingertips. Move-in ready, perfectly located, and packed with lifestyle perks—this one is fun, functional, and full of possibilities! DONT WAIT TOO LONG! Schedule your showing today!
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: Cathy Norman (407-247-7180)
650 CAYUGA DR, WINTER SPRINGS, FL 32708
$709,000113 Days on yellowkey MLS ID: O6378029
1 Days Off yellowkey (back on 4/24/2026)
REDUCED by $15,000 (2.1%) on 04/15/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2429 Built: 1987Monthly Fee: $6 Tax: $5,200 (2025)Community: Tuscawilla Unit 14ASpa: YesSingle Family
Taxes:$5,200
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Price Improvement - Sellers Motivated! Welcome home to this stunning 4-bedroom, 3-full bath pool home located in the highly sought-after Chelsea Woods community of Tuscawilla! Situated on an oversized corner lot, this property offers a fully fenced backyard framed by majestic shade trees, providing exceptional privacy and charm. The tranquil outdoor living space is designed for both comfort and entertaining, featuring a screened-in pool and lanai, low-maintenance and pet-friendly artificial turf with deodorized fill, a putting green, and a fire pit—perfect for year-round gatherings. Inside, enjoy a desirable split-bedroom floor plan with a spacious primary bedroom and en suite. The open living areas are filled with natural light and showcase vaulted ceilings, skylights, and a cozy fireplace that adds warmth and character. The large kitchen offers ample counter space, generous storage, and stainless steel appliances—ideal for the home chef! Seamlessly blending indoor comfort with exceptional outdoor living, this home is a rare opportunity in one of Tuscawilla’s most desirable neighborhoods.
Listing is courtesy of: ALL SELLERS & BUYERS REALTY INC (407-766-9940)
Listing Agent: Jamie Ampel (407-766-9940)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.