Location: Winter Springs
Keyword(s): Winter Springs High
Keyword(s) High School: Winter Springs High
Do Not Show Listings
709 SAILFISH RD, WINTER SPRINGS, FL 32708
$402,500198 Days on yellowkey MLS ID: O6364715
REDUCED by $5,000 (1.2%) on 06/08/2026
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,463
Elementary School: Layer Elementary
High School: Winter Springs High
Tax Year: 2024
Middle School: Indian Trails Middle
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)
130 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708
$739,90030 Days on yellowkey MLS ID: O6409028
1 Days Off yellowkey (back on 6/8/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2433 Built: 1999Monthly Fee: $187 Tax: $7,238 (2025)Community: Seville ChaseSpa: YesSingle Family
Taxes:$7,238
Elementary School: Sterling Park Elementary
Tax Year: 2025
Middle School: South Seminole Middle
Remarks: Discover the perfect blend of comfort, privacy, and luxury in the sought-after gated community of Seville Chase. Nestled on a large private fenced lot, this beautifully maintained 4-bedroom, 3-bathroom home offers a desirable 3-way split floor plan designed for both everyday living and entertaining with no rear neighbors. Step inside to find elegant upgrades throughout, including crown molding, upgraded baseboards, rounded corners, and upgraded interior doors that add a refined touch to every room. The spacious family room is the heart of the home, featuring a cozy fireplace and surround sound for the ultimate movie night or game day experience. The kitchen and living spaces flow seamlessly to your own outdoor oasis complete with a sparkling pool, relaxing spa, and patio surround sound system — perfect for entertaining or unwinding in total privacy. Additional recent improvements provide peace of mind and energy efficiency, including: new 2-stage variable AC with humidity control (2023), new water heater (2023), added blown-in insulation with plywood attic flooring (2023) and new wood-look tile flooring in the rear bedrooms With its thoughtful layout, premium upgrades, and resort-style backyard, this home offers the Florida lifestyle you’ve been waiting for in one of the area’s most desirable gated neighborhoods.
Listing is courtesy of: FLORIDA RE ANALYSTS, INC (407-702-8363)
Listing Agent: Drew Vandermay (407-221-7041)
1128 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708
$469,00079 Days on yellowkey MLS ID: O6395600
REDUCED by $9,500 (2.0%) on 06/06/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2344 Built: 2021Monthly Fee: $236 Tax: $2,985 (2025)Community: Seminole Crossing TwnhmsTownhouse
Taxes:$2,985
Remarks: One or more photo(s) has been virtually staged. Welcome to an exceptional opportunity in the heart of Winter Springs, where lifestyle, location and luxury converge at 1128 Spotted Sandpiper Loop. Positioned in a thoughtfully planned community, this residence offers the ideal balance of elegance and everyday convenience. From moment you arrive, you are embraced by a neighborhood designed for connection and ease, tree-lined streets, inviting trails and a sense of community that makes this address desirable. Ideally just moments from Winter Springs Town Center, this residence offers an accessible lifestyle. Natural light fills the interiors, creating a warm and welcoming ambiance suited for relaxed living and stylish entertaining. Thoughtfully designed across three levels, the first floor offers a private retreat ideal for guests, complete with its own en suite. The second level unfolds into the heart of the home, featuring an open concept living space with a well-appointed kitchen, dining area and inviting family room. The third floor is dedicated to restful living, showcasing three bedrooms, two full baths and a convenient laundry area. Updates include new carpeting throughout with transferable warranty and fresh interior paint reflecting the home's meticulous maintenance. Beyond your doorstep, accessibility becomes a defining feature of this lifestyle. Enjoy proximity to local shops, dining, parks and top-rated Seminole County schools, all just moments away. With easy access to major roadways, commuting to downtown Orlando, nearby business hubs, or weekend destinations is simple and efficient. Amenities include community pool, trails and accessibility to area favorites.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Jackie Hughes (407-247-0030)
4951 COURTLAND LOOP, WINTER SPRINGS, FL 32708
$690,000156 Days on yellowkey MLS ID: O6374007
REDUCED by $10,000 (1.4%) on 05/05/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2562 Built: 1984Monthly Fee: $40 Tax: $7,807 (2024)Community: Tuskabay Ph 1Single Family
Taxes:$7,807
Elementary School: Keeth Elementary
Remarks: This beautifully updated home blends timeless character with modern comfort, offering an inviting layout designed for both everyday living and entertaining. The light-filled interior showcases a stunning, renovated kitchen with new quartz extended countertops, a butcher block island, recessed lighting, and a full suite of high-end appliances including a JennAir refrigerator, KitchenAid pull-out refrigerator and freezer with ice maker, double oven and stovetop, wine and beverage cooler, and dishwasher. Major system upgrades add peace of mind and efficiency, featuring a newer roof installed in 2021, a fully paid off 11.745 kW (DC) solar system paired with a Tesla Powerwall 2.1 (7 kW DC battery capacity), whole-home water filtration and softener, high-efficiency heat pump water heater, new double-paned windows, Nest thermostats for upstairs and downstairs climate control, upgraded outlets with USB and modern switches, and new blinds throughout. The spacious primary bathroom has been fully remodeled with glass shower doors, new quartz countertops, and a farmhouse sink. Outside, enjoy exceptional curb appeal and a private backyard retreat with a screened-in pool, expansive paver patio, new extended paver walkway wrapping around the backyard, upgraded irrigation and sprinkler system, new gutters, and recently serviced chimney. The property is framed by mature, recently trimmed water and live oaks, enhancing both beauty and shade, while added features such as a new front door with wide extended entry, exterior Ring cameras and floodlights complete this truly move-in-ready home designed for a seamless indoor-outdoor Florida lifestyle.
Listing is courtesy of: MOMENTUM REALTY (904-903-1558)
Listing Agent: Carolina Taborda (832-349-8266)
986 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708
$498,900155 Days on yellowkey MLS ID: O6374288
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1864 Built: 1985Monthly Fee: $3 Tax: $3,119 (2024)Community: Oak Forest Unit 4Spa: YesSingle Family
Taxes:$3,119
Remarks: 986 Turkey Hollow Circle—where comfort, style, and Florida living come together beautifully. Nestled in one of Winter Springs’ most desirable neighborhoods, this 4-bedroom, 2-bath pool home offers the perfect blend of warmth, functionality, and thoughtful updates—just minutes from Tuskawilla Road, SR-434, shopping, dining, and top-rated schools. Step inside to an open, light-filled great room where the kitchen, dining, and living spaces flow effortlessly—ideal for both everyday living and entertaining. The heart of the home is the kitchen, featuring rich cabinetry, custom backsplash, farmhouse sink, and a spacious island with cooktop and bar seating—perfect for gathering and connection. Just beyond, the inviting living room showcases vaulted ceilings, recessed lighting, tile flooring, and a stunning brick fireplace, creating a cozy yet open atmosphere. Sliding glass doors lead to your private outdoor retreat. Enjoy true Florida living outdoors with a sparkling pool, heated spa, and expansive covered lanai (10’ x 48’)—perfect for relaxing evenings, entertaining guests, or weekend poolside fun. Wood-tone decking, a fire pit area, gazebo dining space, and dedicated grill area complete this backyard oasis. The primary suite is a peaceful escape, offering private lanai access, a spacious bath, and walk-in closet. A split floor plan provides three additional bedrooms and an updated guest bath with convenient pool access—ideal for family or guests. Recent updates include: • POOL & DECK RESURFACED (2024) + new heater & pump • ROOF (2020) • Updated bedroom WINDOWS (2024) • Renovated GUEST BATH (2024) • New recessed lighting (2024) • New stainless steel refrigerator (2023) • Lanai flooring, spa lighting, gazebo & paver grill area Warm, welcoming, and move-in ready—this is the kind of home where memories are made. (All information intended to be accurate, but not guaranteed.)
Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)
Listing Agent: Christopher Dunlop (321-223-0407)
560 PLEASANT GROVE DR, WINTER SPRINGS, FL 32708
$425,00054 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
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)
446 CLUB DR, WINTER SPRINGS, FL 32708
$269,000128 Days on yellowkey MLS ID: O6380694
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1460 Built: 1994Monthly Fee: $520 Tax: $886 (2024)Community: Cypress ClubTownhouse
Taxes:$886
Elementary School: Highlands Elementary
Remarks: Discover effortless living in this immaculate 3-bedroom, 2-bath townhome nestled in the desirable Cypress Club at The Highlands. Thoughtfully maintained and beautifully updated, this residence offers the perfect blend of comfort, style, and convenience with a desirable split-bedroom floor plan—featuring one bedroom and a full bathroom on the main level, and the primary suite along with a third bedroom upstairs. Sliding glass doors open to a private screened porch, ideal for morning coffee, evening relaxation, or entertaining guests. This inviting space offers seamless indoor-outdoor living along with additional storage. The upgraded kitchen is a true highlight, showcasing solid wood cabinetry, modern countertops, and a breakfast bar perfect for casual dining or hosting friends and family. Two reserved parking spaces are conveniently located directly at your front door. Enjoy the resort-style lifestyle The Highlands is known for, offering a community pool, recreational building, tennis courts, and scenic hiking trails. Ideally located near I-4 and SR-417, commuting and weekend adventures are effortless. HOA fees provide exceptional value, covering exterior building and grounds maintenance, community amenities, —delivering peace of mind and truly low-maintenance living. IMPORTANT MESSAGE- While this townhouse HOA fees may seem higher, it covers roof replacement and maintenance (brand new 2026), exterior maintenance, landscaping, and more. A single-family home may have lower HOA fees, but usually comes with higher maintenance costs, more upkeep, and added stress - making the overall expense very similar in the end, with far less hassle in a townhouse community. Schedule your private showing today and make this exceptional townhome yours.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Hanoi Burgos (407-342-1539)
476 CLUB DR, WINTER SPRINGS, FL 32708
$275,00088 Days on yellowkey MLS ID: O6392856
2 Days Off yellowkey (back on 5/8/2026)
REDUCED by $10,000 (3.5%) on 04/22/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1460 Built: 1995Monthly Fee: $520 Tax: $1,765 (2025)Community: Cypress ClubTownhouse
Taxes:$1,765
Remarks: Under contract-accepting backup offers. Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy the benefits of a new roof 2026, new water heater 2026, 2020 A/C system, a full repipe completed in 2016, and a 2016 whole home water softener. Inside, you’ll find an inviting layout with knockdown ceilings throughout the main level and an open living and dining area tucked toward the rear of the home for added privacy. Updated recessed lighting enhances the space, creating a warm and welcoming atmosphere. Just beyond, a step-down enclosed patio offers a serene retreat overlooking wooded views—perfect for relaxing or entertaining. The flexible floor plan includes a downstairs bedroom with an adjacent full bath, ideal for guests, a home office, or multi-generational living. Upstairs, two generously sized bedrooms feature soaring ceilings and abundant natural light. The primary suite offers ample closet space and tranquil views of the surrounding greenery, along with a spacious en-suite bath complete with a Jacuzzi tub and separate shower—perfect for unwinding after a long day. Cypress Club stands out as the only neighborhood within The Highlands with its own private pool, in addition to access to the community’s extensive amenities. Residents enjoy multiple pools, tennis courts, scenic walking trails, parks, pavilions, BBQ areas, a clubhouse, as well as volleyball and basketball courts—delivering a true Florida lifestyle right outside your door. Don’t miss this opportunity to own a move-in-ready home in one of Winter Springs’ most desirable communities!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Jeff Singletary (407-383-1933)
224 HIGHLANDS GLEN CIR, WINTER SPRINGS, FL 32708
$295,00032 Days on yellowkey MLS ID: O6409042
0 Days Off yellowkey (back on 6/5/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1185 Built: 1986Monthly Fee: $63 Tax: $3,265 (2025)Community: Highlands GlenVilla
Taxes:$3,265
Elementary School: Winter Springs Elementary
Remarks: Welcome to 224 Highlands Glen Circle, a beautifully updated 3-bedroom, 2-bath villa with 1,185 sq. ft. of comfortable living space. This home features a modern kitchen with new countertops and appliances, along with fresh interior paint and new flooring throughout. Enjoy the ease of a move-in ready home with a 1-car garage. The community offers fantastic amenities, including a pool, tennis courts, playground, and park, perfect for active lifestyles and family fun. Ideally located in Winter Springs, this villa combines style, convenience, and comfort, schedule your showing today!
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Brian Hyser (407-951-2472)
4991 COURTLAND LOOP, WINTER SPRINGS, FL 32708
$750,00030 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
Taxes:$6,752
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)
114 SUNDANCE CT, WINTER SPRINGS, FL 32708
$305,500218 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
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
$384,900178 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
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)
1281 NATURES WAY, WINTER SPRINGS, FL 32708
$1,200,00050 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)
510 SONATA CT, WINTER SPRINGS, FL 32708
$824,90053 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
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
$824,90064 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)
330 HAYES RD, WINTER SPRINGS, FL 32708
$820,00047 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
$438,997121 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)
140 N. FAIRFAX, WINTER SPRINGS, FL 32708
$325,000199 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)
1444 BIRD RD, WINTER SPRINGS, FL 32708
$838,500277 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)
417 CRUZ BAY CIR, WINTER SPRINGS, FL 32708
$435,00033 Days on yellowkey MLS ID: O6408099
2 Days Off yellowkey (back on 5/28/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2176 Built: 2006Monthly Fee: $245 Tax: $3,673 (2024)Community: The Landings At ParkstoneTownhouse
Taxes:$3,673
Remarks: If you are looking for a turnkey property, this home is it! A rare find end unit has been completely updated & meticulously maintained inside this secluded gated community of The Landings at Parkstone. Imagine yourself in this absolutely stunning home featuring a gourmet kitchen with a clean modern look remodeled in 2025 with premuim quartz countertops, backsplash, new custom cabinetry and new appliances that will please the chef in the family. The primary bathroom was updated in 2024 and features a modern soaking tub, a spacious shower, dual vanity with quartz countertops & new plumbing fixtures. All new flooring throughout with plank tile downstairs and luxury vinyl plank upstairs. Some additional updates include: new AC 2024, roof in 2023, exterior paint in 2023, interior paint in 2025, screened in porch & more. This floor plan offers maximum flexibility with one bedroom & full bath downstairs. The Primary bedroom located upstairs has a custom tray ceiling & an incredibly spacious walk in closet with a small window for natural light. The upstairs has a guest bedroom along with a full bathroom. This neighborhood offers a dedicated community pool for The Landings residents only, secured mailboxes & lawncare included in the quarterly dues. Convenient to the Winter Springs Town Center, Cross Seminole Trail, Dog Park, Central Winds Park & easy eaccess to 417 to shorten the commute. Highly rated Seminole Conty Schools. Bring your most discriminating Buyers as this one will not disappoint!
Listing Agent: Ron Verzaro, Ii (407-221-5464)
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