Location: Winter Springs
Do Not Show Listings
618 LOCUST CT, WINTER SPRINGS, FL 32708
$228,80032 Days on yellowkey MLS ID: O6409201
0 Days Off yellowkey (back on 6/19/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1326 Built: 1978 Tax: $4,436 (2025)Community: Foxmoor Unit 2Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,436
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: The seller is currently in a multiple offer scenario related to the Buyer/Property Address listed above and you are receiving this message as a result of a request for the Buyer's highest and best offer. Should the Buyer choose to participate in submitting their highest and best offer, the deadline to do so is 6/10/2026 11:59:00 PM Mountain Time. ***SEE ATTACHMENTS...Awesome opportunity to own this home located in the established Foxmoor community in Winter Springs, this 3-bedroom, 2-bath home offers a great opportunity to make it your own. Featuring a functional layout and plenty of potential, this property is conveniently located near shopping, dining, parks, and major roadways. A great option for buyers looking to add their personal touch. Property being sold AS-IS. Call your agent today as this one will not last long.
Listing is courtesy of: REAL ESTATE PROFESSIONALS SE (407-331-7600)
Listing Agent: David Kellam (407-592-5850)
170 WOODED VINE DR, WINTER SPRINGS, FL 32708
$649,9002 Days on yellowkey MLS ID: O6418077
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2470 Built: 2019Monthly Fee: $137 Tax: $8,571 (2025)Community: Tuskawilla Crossings Ph 1Single Family
Taxes:$8,571
High School: Winter Springs High
Middle School: Indian Trails Middle
Remarks: Located in the highly sought after Tuskawilla Crossings Community, this newer home blends spacious living, flexible design, and modern conveniences in one exceptional package. Offering a total of 4 bedrooms plus office and 3.5 bathrooms, this thoughtfully designed floor plan is ideal for multigenerational living, extended stays for guests, remote professionals, or anyone seeking additional privacy and versatility. The main residence encompasses 3 bedrooms, 2.5 bathrooms, and a dedicated office/flex room, while a separate 1 bedroom, 1 bath suite above the garage creates a private retreat complete with its own entrance. The main level showcases an open concept design where the family room flows seamlessly into the spacious eat in kitchen. The kitchen is beautifully appointed with 42 inch cabinetry, quartz countertops, upgraded stainless steel appliances, and a generous walk in pantry. A versatile office/flex room offers endless possibilities as a home office, playroom, fitness area, study space, or hobby room.Upstairs, the primary bedroom serves as a comfortable escape, featuring a walk in closet and a spacious en suite bath with dual vanities, a garden tub, and separate walk in shower. French doors lead to a private balcony, providing the perfect spot to enjoy a quiet morning or unwind at the end of the day. Two additional bedrooms and a full bath with dual sinks complete the second floor of the main residence. One of the home's most desirable and unique features is the private suite above the garage. Measuring approximately 19' x 16', this separate living space includes its own full bathroom, dedicated HVAC system, built-in cabinetry and private entrance, making it ideal for in-laws, guests, college aged children, a home business, or additional flex space. The remainder of the home highlights a front porch, a covered rear porch, a brick paved driveway, oversized parking area, two car garage, whole home Gigabit Wi Fi, fiber internet, smart locks, smart lighting and a 60 amp outlet ready for electric vehicle charging. Residents of Tuskawilla Crossings enjoy resort style amenities including a community pool with cabanas, playground, walking trails, multiple dog parks, and direct access to the Seminole County Trail. Ideally located just minutes from Winter Springs Town Center, shopping, dining, top rated Seminole County schools, and SR 417, this home combines modern living with exceptional convenience.
Listing is courtesy of: DIBS REALTY, LLC (407-537-2232)
Listing Agent: Ashley Swindell (407-687-5481)
424 FLATWOOD DR, WINTER SPRINGS, FL 32708
$525,00039 Days on yellowkey MLS ID: S5149589
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2164 Built: 1997Monthly Fee: $82 Tax: $3,052 (2024)Community: Tusca OaksSingle Family
Taxes:$3,052
Tax Year: 2024
Remarks: Excellent opportunity in desirable Tusca Oaks/Tuscawilla area. Spacious 4BR/2.5BA with functional floor plan, generous room sizes, and strong curb appeal. Home has been well maintained and is in mostly original condition, offering buyers the chance to update to their personal taste while gaining value in a highly desirable Seminole County location. Brand New Roof - 1 yr old. Community features including mature landscaping, sidewalks, and convenient access to parks, trails, golf, shopping, dining, and major roads. Strong owner-occupancy area with long-term neighborhood stability. Easy to show.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alexandra Arena Gil (321-228-6377)
1200 ROYAL OAK DR, WINTER SPRINGS, FL 32708
$499,99952 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
Elementary School: Rainbow Elementary
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)
975 DYSON DR, WINTER SPRINGS, FL 32708
$879,0003 Days on yellowkey MLS ID: O6417467
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2191 Built: 1980 Tax: $6,089 (2025)Community: Winter Spgs Unit 3Single Family
Taxes:$6,089
Remarks: Under contract-accepting backup offers. Nestled on nearly two private acres in coveted Old Tuskawilla, this one-of-a-kind custom estate offers a rare opportunity to enjoy space, privacy, and timeless character in one of Seminole County's most sought-after communities. Surrounded by majestic oak trees, the property feels like a private retreat while remaining just minutes from top-rated schools, parks, golf, dining, and shopping. A private driveway leads to the home's side-entry two-car garage and picturesque setting. Inside, 2,191 square feet of living space blends warmth and functionality. Solid cherry hardwood flooring flows throughout the main level, where you'll find the formal dining room, a spacious family room, two fireplaces, a breakfast nook, and a generously sized primary suite conveniently located on the first floor. Also on the main level is a flexible office space that could easily serve as a fourth bedroom with minimal modifications, offering added versatility for growing families or guests. Upstairs, two bedrooms feature large closets and share a renovated Jack-and-Jill bathroom. The second floor has been updated with luxury vinyl plank flooring. The screened porch provides the perfect place to enjoy morning coffee while overlooking the expansive backyard, offering endless possibilities for a custom pool, guest house, workshop, or simply enjoying the natural beauty of the property. Nature lovers will appreciate the trail located directly behind the property, providing access for walking, jogging, and exploring the outdoors. Major updates provide peace of mind, including a whole-house repipe (2022), a 10' x 12' storage shed added in 2025, a new roof (2026), and fresh exterior paint (2026). While the kitchen and primary suite present opportunities for cosmetic updates and personalization, the home's solid construction, exceptional lot, and desirable location create an incredible foundation for your vision. Properties with this much land, character, and potential rarely become available in Tuskawilla. Whether you're seeking room to spread out, a private estate setting, or the chance to create your forever home, this exceptional property offers a truly unique opportunity.
Listing is courtesy of: VAN DEN BERG REAL ESTATE GROUP (407-739-9970)
Listing Agent: Caroline Van Den Berg (407-739-9970)
472 DEWARS CT, WINTER SPRINGS, FL 32708
$499,90016 Days on yellowkey MLS ID: O6413206
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2222 Built: 1995Monthly Fee: $13 Tax: $2,066 (2025)Community: Highland Lake Ph 2Single Family
Taxes:$2,066
Elementary School: Highlands Elementary
Middle School: South Seminole Middle
Remarks: Under contract-accepting backup offers. Welcome to 472 Dewars Court, a beautifully maintained 4-bedroom, 2.5-bath pool home offering over 2,200 square feet of living space in one of Winter Springs' most desirable communities. Tucked away at the end of a quiet cul-de-sac, this exceptional property provides the perfect combination of privacy, comfort, and convenience with a serene wooded backdrop and no rear neighbors. Inside, you'll find a spacious and functional floor plan designed for both everyday living and entertaining. The kitchen features a gas stove for the home chef, while the home's whole-house Generac gas generator provides peace of mind and uninterrupted comfort year-round. Multiple living and dining spaces offer flexibility for growing families, remote work, or hosting guests. Step outside to your private backyard oasis featuring a sparkling pool, expansive patio space, and tranquil wooded views—perfect for relaxing, entertaining, or enjoying Florida's beautiful weather. Located within The Highlands, one of Winter Springs' most sought-after communities, residents enjoy access to incredible amenities including a large Olympic-sized community pool, scenic nature trails, multiple parks, playgrounds, and recreation areas surrounded by mature oak trees that create a picturesque neighborhood setting. The Highlands is known for its strong sense of community, low traffic streets, and family-friendly atmosphere. Winter Springs consistently ranks among the most desirable places to live in Seminole County thanks to its highly rated schools, beautiful parks, excellent shopping and dining options, and convenient access to Lake Mary, Oviedo, Winter Park, Downtown Orlando, and major highways. This is a rare opportunity to own a private pool home on a cul-de-sac lot with wooded views in one of Central Florida's most established and sought-after communities. Schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: David Coker (407-923-8290)
1016 WALNUT CREEK CV, WINTER SPRINGS, FL 32708
$539,9004 Days on yellowkey MLS ID: O6414948
1 Days Off yellowkey (back on 6/19/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2375 Built: 2003Monthly Fee: $150 Tax: $3,482 (2025)Community: Parkstone Unit 4Spa: NoSingle Family
Taxes:$3,482
Elementary School: Layer Elementary
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home nestled on a quiet cul-de-sac in the highly desirable gated community of Parkstone. From the moment you arrive, you'll appreciate the inviting curb appeal, fresh exterior paint, and the pride of ownership throughout. Step inside to discover a light and bright interior filled with airy, spacious living areas designed for both everyday comfort and effortless entertaining. Gorgeous luxury vinyl plank flooring flows throughout the main living spaces, while brand-new carpet adds warmth and comfort to the upstairs bedrooms. Entertaining is a breeze in the large dining room with easy access to the kitchen and family room. The heart of the home opens seamlessly to your private backyard retreat, featuring a sparkling saltwater pool, new sod, and a fully fenced yard that offers both privacy and space to relax, play, or entertain. Whether enjoying a morning coffee poolside or hosting weekend gatherings, this outdoor space is sure to impress. Soaring ceilings on the first floor add to the spacious feeling throughout. Step into the pristine primary suite located on the first floor as an added bonus! Primary bath with separate soaking tub, glass enclosed shower and dual sink vanity make this an owner's dream. Major updates provide peace of mind, including ROOF 2019, AC 2024, FRESHLY PAINTED INTERIOR 2021, HOT WATER HEATER 2021,transferable TERMITE BOND, NEW CARPETS in all bedrooms, NEWLY PAINTED POOL DECK and Taexx, an inovative built-in "tubes in the wall" pest control system .....what more could you ask for? One of the many perks of living in Parkstone is that the HOA takes care of lawn maintenance, giving you more time to enjoy the community and everything the area has to offer. Located just minutes from the popular Central Winds Park, you'll have easy access to festivals, sporting events, walking trails, and community activities year-round. You'll also love being close to Winter Springs Town Center, where shopping, dining, and everyday conveniences are just around the corner. This welcoming home offers the perfect blend of comfort, convenience, and lifestyle in one of Winter Springs' most sought-after gated communities.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Colleen Kahl (407-630-0027)
1335 SAN FELIPE CT, WINTER SPRINGS, FL 32708
$450,0003 Days on yellowkey MLS ID: O6417601
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1571 Built: 1987 Tax: $5,051 (2025)Community: Sunrise Village Unit 6Spa: YesSingle Family
Taxes:$5,051
Remarks: Welcome home to this move-in-ready 4-bedroom, 2-bathroom pool home with a 2-car garage, situated on a quiet cul-de-sac with no through traffic. This solid-block-construction home offers an open floor plan and exceptional curb appeal, featuring fresh exterior paint, updated stucco, professional landscaping, and a brand-new roof installed in June 2026. Inside, you'll find fresh interior paint, updated lighting and ceiling fans throughout, and a beautifully renovated kitchen and bathrooms. The spacious kitchen opens to the main living areas and features new stainless steel appliances, making it ideal for both everyday living and entertaining. The living room is anchored by a stunning fireplace that has been transformed with a custom stucco finish, elegant marble accents, and a floating mantel. Major mechanical updates include a 2022 AC system, a brand-new 2026 water heater, and updated plumbing with the home fully repiped, providing added value and peace of mind for years to come. Step outside to enjoy your private screened pool area and fully fenced backyard with no rear neighbors, offering exceptional privacy and the perfect space for relaxation, pets, and outdoor gatherings. With block construction, a brand-new roof, and a location outside of a flood zone, this home offers the potential for lower insurance costs and added peace of mind. For additional buyer confidence, a 4-Point Inspection, Wind Mitigation Report, Wood Destroying Organism (WDO) Report, and Energy Report are attached to the MLS for review. Conveniently located with a low HOA of just $345 per year, this home combines style, comfort, and value in one complete package.
Listing is courtesy of: NEXTDWELL (855-432-1123)
Listing Agent: Austin Cummings (407-242-8891)
71 BOMBAY AVE, WINTER SPRINGS, FL 32708
$215,90016 Days on yellowkey MLS ID: O6414087
REDUCED by $10,000 (4.4%) on 06/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1134 Built: 1960 Tax: $3,899 (2025)Community: North Orlando 1St AddSingle Family
Taxes:$3,899
Remarks: Set in the heart of Winter Springs, 71 Bombay Ave offers the kind of opportunity buyers are always looking for: an established location, a functional footprint, and the chance to create a home that reflects their own style. This property is ready for its next chapter, making it an ideal choice for those who appreciate potential, value, and the ability to personalize a space over time. Life here puts you close to the everyday conveniences and outdoor lifestyle that make Winter Springs so appealing, from nearby parks and playgrounds to community favorites like Central Winds Park, nature trails, sports fields, dog-friendly spaces, and access to the Cross Seminole Trail for biking, walking, and weekend exploring. The area offers a relaxed residential feel while still keeping you connected to Oviedo, Tuscawilla, Winter Springs Town Center, shopping, dining, and major Central Florida corridors. Whether you are looking to renovate, invest, or design a home that feels entirely your own, this property offers a rare chance to bring fresh vision to a well-located Winter Springs address.
Listing is courtesy of: ACME REAL ESTATE FLORIDA LLC (407-601-4958)
Listing Agent: Heather Unger, Pa (407-810-6304)
1702 DAVENPORT CT, WINTER SPRINGS, FL 32708
$569,90064 Days on yellowkey MLS ID: O6398359
0 Days Off yellowkey (back on 6/18/2026)
REDUCED by $10,000 (1.7%) on 06/12/2026
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2101 Built: 1994Monthly Fee: $42 Tax: $7,266 (2024)Community: Davenport GlenSpa: NoSingle Family
Taxes:$7,266
Remarks: Under contract-accepting backup offers. Discover the perfect blend of comfort and convenience in this beautifully refreshed 3-bedroom, 2-bathroom pool home. Boasting a spacious 3-car garage and a sought-after split floor plan, this residence has been revitalized with fresh interior and exterior paint. Experience the ultimate Florida lifestyle—spend your weekends lounging by your private pool or walk across the street to Sam Smith Park. Located just one mile from t Tuscawilla Country Club and zoned for top-rated Seminole County schools (Oviedo High and Indian Trail Middle), this home offers the lifestyle you’ve been searching for.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Hossin Mosaddad (407-949-1249)
805 LEOPARD TRL, WINTER SPRINGS, FL 32708
$565,00044 Days on yellowkey MLS ID: O6405925
REDUCED by $10,000 (1.7%) on 05/25/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2608 Built: 1978 Tax: $2,946 (2024)Community: Winter Spgs Unit 4Single Family
Taxes:$2,946
Elementary School: Keeth Elementary
Remarks: Welcome to 805 Leopard Trail in Winter Springs, a 4-bedroom, 2-bath pool home located in a quiet, established no HOA community. Situated on approximately half an acre, this property offers a rare combination of space, privacy, and natural surroundings. The home features a functional layout with comfortable living areas, while large windows and sliding glass doors provide natural light and seamless access to the backyard. Step outside to a truly special outdoor setting, where mature trees, natural surroundings, and the sounds of nature create a peaceful and private atmosphere. The backyard is a standout feature, complete with a private pool and plenty of space to relax or entertain. The pool area is also plumbed for a future outdoor kitchen, offering additional potential. With a generous lot size, there is ample room for recreation, storage, or future improvements. Conveniently located near University of Central Florida, Central Winds Park, Oviedo Mall, as well as shopping, dining, and major roadways including SR 434 and SR 417, this property offers both tranquility and accessibility in a desirable Winter Springs location.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Wilfred Sierra Sosa, Pa (863-588-8303)
335 KIRKCALDY DR, WINTER SPRINGS, FL 32708
$329,90046 Days on yellowkey MLS ID: O6400818
REDUCED by $10,000 (2.9%) on 06/18/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1178 Built: 1984Monthly Fee: $36 Tax: $3,693 (2025)Community: Highland Village 1Single Family
Taxes:$3,693
Remarks: Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new electrical panel inside and outside. The generously sized primary bedroom includes a built-in California Closets system, providing stylish and highly functional custom storage. The secondary and third bedrooms are also well-sized—perfect for guests, family, or easily converted into a home office. Washer and dryer are included in the sale. Enjoy the covered and screened lanai overlooking a charming New Orleans-style courtyard with pavers, a firepit, and a lamp post. The oversized, fully fenced, and cleared backyard offers plenty of space to relax, entertain, or garden, providing a strong sense of privacy. The Highlands is a highly sought-after, established community with low HOA fees and beautiful mature trees throughout. Amenities include an Olympic-size community pool, walking trails, playground, tennis court, volleyball court, and a clubhouse. Ideally situated just off State Road 434 Florida and Tuskawilla Road, this home offers quick access to Winter Springs Town Center for shopping and dining, and is just a short stroll from Torcaso Park—a lively neighborhood park featuring basketball courts, soccer and football fields, playgrounds for all ages, a splash pad, sand play areas, and picnic pavilions, perfect for both active days and relaxed family outings.
Listing is courtesy of: MILLENIUM REALTY GROUP (407-277-1400)
Listing Agent: Irina Carp (407-969-9937)
577 WALDEN CT, WINTER SPRINGS, FL 32708
$405,00012 Days on yellowkey MLS ID: V4949540
2 Days Off yellowkey (back on 6/18/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1560 Built: 1974 Tax: $3,414 (2025)Community: Walden TerraceSingle Family
Taxes:$3,414
Elementary School: Winter Springs Elementary
Middle School: Tuskawilla Middle
Remarks: NO HOA Corner Lot Single Family Home features 4 beds, 2 baths. Open layout design home with tons of upgrades: Windows replaced back in 2020, ROOF replaced in 2022, Water Heater replaced 2025, Luxury Vinyl floors installed 2026. BRAND NEW INTERIOR PAINT gives a clean look. The kitchen is the focal point of the house. It features subway tiles EXHAUST FAN, STAINLESS STEEL APPLIANCES and cabinets. GRANITE COUNTER TOP installed in 2019 and a brand new fridge 2026. Bathroom with brand new glass doors and brand new bath tub. AC unit installed 2017. A fully fenced yard provides privacy with expansive open space ready for outdoor entertaining and dining space, gardening, play area, fire pit area and also has a chicken coop and chicken run area. All outdoor furniture plus the BBQ grill are included with the sale. 2 car garage and metal husky shelves for storage. Zoned for Seminole County top A rated schools. The property is located in a minimal flood risk area (Zone X). Schedule your viewing today.
Listing is courtesy of: RISE REALTY OF FLORIDA LLC (386-804-4114)
Listing Agent: Nicole Garcia Lozada (787-235-4293)
1055 CHESTERFIELD CIR, WINTER SPRINGS, FL 32708
$510,00016 Days on yellowkey MLS ID: O6413841
REDUCED by $5,000 (1.0%) on 06/18/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1665 Built: 1984Monthly Fee: $25 Tax: $5,048 (2025)Community: AmherstSpa: NoSingle Family
Taxes:$5,048
Remarks: Beautiful pool home located in the highly desirable Amherst community of Winter Springs! Situated on an oversized .34-acre lot, this well-maintained 3-bedroom, 2-bath home offers a spacious split-bedroom floor plan with vaulted ceilings, abundant natural light, and a cozy wood-burning fireplace in the oversized family room. Updated bathrooms and ceramic wood looking flooring in main living areas. The screened with an large pool and covered lanai create the perfect setting for year-round outdoor living and entertaining, and no rear neighbors for privacy. The primary suite features a walk-in closet and spacious bath with dual sinks newly remodeled. Additional highlights include a 2-car garage, irrigation system, rain gutters, public utilities, and low annual HOA dues. New Roof (2025), New Water Heater & A/C (2024). Conveniently located near top-rated Seminole County schools, parks, shopping, dining, major roadways, and the 417.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Brittany Zapitz (321-230-4445)
877 BENCHWOOD DR, WINTER SPRINGS, FL 32708
$450,00023 Days on yellowkey MLS ID: O6410431
REDUCED by $10,000 (2.2%) on 06/18/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1612 Built: 1983Monthly Fee: $3 Tax: $3,127 (2024)Community: Oak Forest Unit 3Single Family
Taxes:$3,127
Remarks: Inviting curb appeal welcomes you into this beautifully maintained Winter Springs pool home tucked within the peaceful established subdivision of Oak Forest. Step inside to an open floor plan with immediate views of the backyard oasis, creating a light and airy feel perfect for everyday living and entertaining. The spacious kitchen opens seamlessly to the living and dining areas and features granite countertops, stainless steel appliances and a breakfast bar ideal for gathering with family and friends. The floor plan offers comfortable living spaces, while sliding doors lead out to the screened porch overlooking the private backyard retreat. Enjoy Florida living year-round with the screened patio, resurfaced pool featuring a PebbleTec finish completed in 2020, a fully fenced yard and plenty of room to relax or entertain outdoors. Major updates provide peace of mind, including the roof, AC, and water heater all replaced in 2015. Additional improvements include gutters added in 2020, pool pump replaced in 2016, new garage door opener in 2025, and updated microwave, dishwasher, and garbage disposal in 2026. This home sits on a spacious lot in a quiet, established neighborhood. Conveniently located near SR-417, shopping, dining, and top-rated Seminole County schools - walking distance to both the elementary and middle school. This home is also just minutes from Trotwood Park and Central Winds Park which features pickleball courts, sports fields, playgrounds, walking trails, and community events.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Melissa Condrey (407-505-9339)
724 LAKESIDE DR, WINTER SPRINGS, FL 32708
$264,90017 Days on yellowkey MLS ID: O6412679
2 Days Off yellowkey (back on 6/17/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1168 Built: 1985Monthly Fee: $95 Tax: $2,675 (2025)Community: WildwoodSingle Family
Taxes:$2,675
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 724 Lakeside Dr, nestled in the highly sought-after Wildwood community. This beautifully maintained 2-bedroom, 2-bathroom home offers 1,168 square feet of comfortable living space and presents an excellent opportunity for first-time homebuyers, downsizers, or anyone seeking a move-in-ready home in one of Winter Springs' most established neighborhoods. As you step inside, you'll immediately notice the fresh updates throughout, including brand-new carpet that adds warmth and comfort to every room. The functional floor plan offers a spacious living and dining area filled with natural light, creating an inviting atmosphere for both everyday living and entertaining guests. The kitchen provides ample cabinet and countertop space with easy access to the main living areas, making meal preparation and gatherings effortless. The primary suite offers a private retreat complete with an en-suite bathroom and generous closet space. A well-sized secondary bedroom and full guest bathroom provide flexibility for family members, guests, or a home office setup. The guest bathroom has been enhanced with a newly installed backsplash, adding a stylish and modern touch. Step outside and enjoy all that the Wildwood community has to offer. Residents have access to a community swimming pool, tennis courts, playground, and a community clubhouse, providing plenty of opportunities for recreation and social gatherings. The neighborhood's mature landscaping, tree-lined streets, and established character create a welcoming environment that homeowners have enjoyed for years. Conveniently located in the heart of Winter Springs, this home is just minutes from the Cross Seminole Trail, Central Winds Park, Winter Springs Town Center, shopping, dining, and top-rated Seminole County schools. Easy access to major roadways makes commuting throughout Central Florida a breeze while still allowing you to enjoy the charm and tranquility of this sought-after community. Whether you're searching for your first home, looking to downsize, or seeking a low-maintenance lifestyle in a prime location, this property offers the perfect combination of comfort, convenience, and community. Schedule your private showing today and discover everything 724 Lakeside Dr has to offer.
Listing Agent: Eric Campbell (321-279-8941)
1421 HAPPY BIRD LN, WINTER SPRINGS, FL 32708
$543,888220 Days on yellowkey MLS ID: O6359884
REDUCED by $19,520 (3.5%) on 06/17/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2502 Built: 2019Monthly Fee: $130 Tax: $4,781 (2024)Community: Tuskawilla Crossings 34'SSingle Family
Taxes:$4,781
Remarks: Welcome home! Fall in love this welcoming two-story home that features 4 bedrooms and 3.5 bathrooms, perfectly positioned across from the Cross Seminole Trail. Start your day with a cup of coffee on the charming covered front porch, where you can take in the refreshing breeze and picturesque views of the 13-mile trail that winds through Seminole County and connects to other scenic trails. Step inside to discover an inviting open floor plan enhanced by beautiful wood-style tile flooring. Prepare your favorite meals in the gourmet kitchen with stainless steel appliances, pantry, modern fixtures, and breakfast bar ideal for casual dining. The open-concept living and dining areas create the perfect setting for effortless entertaining. The primary suite, conveniently located on the first floor, includes a walk-in closet and a private ensuite bathroom with dual sinks and a walk-in shower. Ascend to versatile loft area upstairs offering additional space for work, play, or relaxation. You will also appreciate the secondary primary suite on this level, complete with a walk-in closet, dual sinks, and shower. Additionally, two generously sized bedrooms await your use along with a full bathroom. Outside, unwind on the covered back patio, surrounded by vinyl fencing for added privacy. A rear-facing two-car garage with a paver driveway completes the property. This home is part of the Tuskawilla Crossing community, which includes a dog park, a sparkling community pool for leisurely fun, and a playground. The area is rich in dining and shopping options and provides easy access to the 417. Situated in Seminole County which is well known for its public school system. Don’t miss the chance to make this exceptional home yours—schedule a showing today!
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: Brent Dehoop (407-448-8971)
214 PERTH CT, WINTER SPRINGS, FL 32708
$589,90038 Days on yellowkey MLS ID: O6407533
1 Days Off yellowkey (back on 6/3/2026)
Bed: 6 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2247 Built: 1980Monthly Fee: $67 Tax: $5,200 (2024)Community: Highlands Sec 6Single Family
Taxes:$5,200
Elementary School: Woodlands Elementary
Remarks: Under contract-accepting backup offers. Exceptional investment opportunity in the highly sought-after Highlands community of Winter Springs! This rare and one-of-a-kind duplex features two spacious 3-bedroom, 2-bath units, each offering a 2-car garage, fenced backyard, soaring high ceilings, and thoughtfully designed floor plans that create an open and inviting feel. Both sides are professionally leased, currently generating a combined $3,200/month in gross rental income, with tenants responsible for their own utilities — and there is strong potential to increase rents in today’s market, making this an even stronger long-term investment opportunity. Recent updates provide peace of mind for years to come, including a new roof (2021), fresh exterior paint (2021), HVAC systems replaced on both sides (2021), updated windows, replumbing, updated tile flooring, and freshly painted interiors (2024). Both bathrooms have been professionally re-glazed to look like new while adding long-term durability and extended life to the surfaces. This duplex is extremely hard to find and offers endless possibilities for both investors and owner-occupants alike. It is an ideal income-producing property or perfect opportunity for a first-time homebuyer utilizing FHA financing — allowing the owner to live in one unit while renting out the other side to help offset the mortgage payment. Located in The Highlands, one of Winter Springs’ most desirable communities, residents enjoy scenic walking trails, a waterfront playground, sparkling community pool, clubhouse, and a low HOA — all within an amazing neighborhood known for its lifestyle and convenience. Whether you’re expanding your portfolio, house hacking, or searching for a flexible multigenerational opportunity, this property truly stands out from the rest.
Listing is courtesy of: EXP REALTY LLC (407-641-2808)
Listing Agent: Jeffrey Osborn, Jr (407-221-7134)
114 STONE GABLE CIR, WINTER SPRINGS, FL 32708
$485,9004 Days on yellowkey MLS ID: O6417280
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1814 Built: 1998Monthly Fee: $50 Tax: $4,263 (2025)Community: Stone GableSingle Family
Taxes:$4,263
Remarks: Welcome to the desirable city of Winter Springs, where 114 Stone Gable Cir sits on a beautiful corner lot with peaceful pond views to the rear and side of the home. Just minutes from shopping, restaurants, theme parks, major roads, and the airport, this move-in ready residence puts convenience right at your fingertips. Inside, 1,814 square feet of bright living space welcomes you with high ceilings and an open floor plan that flows naturally from room to room. Hard flooring runs throughout, keeping upkeep easy while adding a clean, modern look. The kitchen is ready for everything from casual breakfasts to weekend gatherings, featuring sleek granite countertops and stainless steel appliances. This thoughtfully designed home offers three comfortable bedrooms and two full bathrooms. The smart split layout tucks the primary bedroom away on its own side for added privacy, creating a quiet retreat at the end of the day, while two additional bedrooms provide flexible space for family, guests, or a home office. The real showstopper waits out back. Step onto the screened-in porch and enjoy your own private pool, perfect for cooling off under the Florida sun or relaxing as you take in the serene water views. The corner-lot setting adds extra elbow room and a sense of openness rarely found. With its prime location, modern finishes, and resort-style outdoor living, this Winter Springs gem checks every box. Schedule your private showing today and make it yours before it's gone!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Kathy Williams (407-230-7305)
1385 SAN DIEGO CT, WINTER SPRINGS, FL 32708
$320,00072 Days on yellowkey MLS ID: O6397680
REDUCED by $29,000 (8.3%) on 06/17/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1518 Built: 1983Monthly Fee: $29 Tax: $1,283 (2025)Community: Sunrise Village Unit 1Spa: NoSingle Family
Taxes:$1,283
High School: Oviedo High
Remarks: HUGE PRICE REDUCTION! LOWEST PRICED HOME IN SUNRISE VILLAGE! 2/2 UPDATED HOME! PLUS A BONUS ROOM PERFECT FOR OFFICE, NURSERY, PLAYROOM, HOBBY ROOM, FLORIDA ROOM OR JUST ADDITIONAL LIVING SPACE! OPEN FLOOR PLAN! KITCHEN FEATURES TILE FLOORS, EAT IN KITCHEN AND LIGHT WOOD CABINETRY! ROOF 2022, A/C 2023, WATER HEATER 2025! MAIN BATH UPDATED WITH DECORATIVE TILE, GRANITE COUNTER, TILE FLOOR! DOUBLE PANED WINDOWS! WIDE BLINDS! KNOCKDOWN CEILINGS! NO CARPETING THRU OUT! LARGE SCREENED PATIO WITH TILE FLOOR! LOTS OF NATURAL LIGHT! FANS! LAUNDRY IN GARAGE! GREAT LOCATION, HIGHLY RATED SCHOOLS, LOW HOA DUES ($345 YEAR), COMMUNITY BASKETBALL, TENNIS AND PLAYGROUND!. CONVENIENT TO ALL AREAS OF TOWN! PLEASE NOTE: SOLAR PANELS ON ROOF ARE LEASED, AND LEASE IS TRANSFERABLE! APPROX $80 MONTH! SELLER NOTES WITH POWER COMPANY CREDITS, BILL HAS BEEN APPROX. $30 MONTH!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Diane Fuller (407-923-2090)
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