Location: Winter Springs
Do Not Show Listings
472 DEWARS CT, WINTER SPRINGS, FL 32708
$499,90019 Days on yellowkey MLS ID: O6413206
0 Days Off yellowkey (back on 6/19/2026)
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,066
Elementary School: Highlands Elementary
High School: Winter Springs High
Tax Year: 2025
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
$539,9007 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
Middle School: Indian Trails Middle
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
$450,0006 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
Elementary School: None
High School: None
Middle School: None
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
$215,90019 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
$569,90067 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
Tax Year: 2024
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
$565,00047 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
$329,90049 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)
1055 CHESTERFIELD CIR, WINTER SPRINGS, FL 32708
$510,00019 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
Elementary School: Rainbow Elementary
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)
724 LAKESIDE DR, WINTER SPRINGS, FL 32708
$264,90020 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
$543,888223 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
$589,90041 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
$485,9007 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)
448 MACGREGOR RD, WINTER SPRINGS, FL 32708
$350,00076 Days on yellowkey MLS ID: O6397231
0 Days Off yellowkey (back on 6/17/2026)
REDUCED by $10,000 (2.8%) on 05/27/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1477 Built: 1993Monthly Fee: $6 Tax: $1,141 (2024)Community: Highland Village 2Spa: NoSingle Family
Taxes:$1,141
Remarks: Explore 448 MacGregor Rd, a individual residence with a straightforward design and integrated features. The interior includes a fireplace, and the primary bedroom features a walk in closet; the primary bathroom provides double sinks and a Jacuzzi. The exterior includes a covered patio and a fenced in backyard, providing an enclosed outdoor area. This property contains practical elements for daily living. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
1233 STONE HARBOUR RD, WINTER SPRINGS, FL 32708
$729,900119 Days on yellowkey MLS ID: O6384753
0 Days Off yellowkey (back on 4/2/2026)
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2908 Built: 2003Monthly Fee: $150 Tax: $2,062 (2025)Community: Parkstone Unit 3Single Family
Taxes:$2,062
Remarks: Under contract-accepting backup offers. Experience the ultimate Florida lifestyle at this stunning 4-bedroom (plus home office) or 5-bedroom, 3.5-bathroom retreat nestled in the exclusive gated community of Parkstone. Come home to soaring, high ceilings and a bright, open floorplan that’s an entertainers dream. The Chef’s kitchen features stainless steel appliances, and a breakfast bar as well as a window enjoying views of the screen patio and beautiful backyard. You will love the oversized primary suite that features stunning conservation views, and connects to a private, flexible room perfect for an office or nursery, or even a fifth bedroom. One of the additional bedrooms has an on suite bathroom and walk in closet as well. Wake up to breathtaking sunrises and spend your evenings watching wildlife. This exceptional property features a private 300ft boardwalk that winds through Florida Hammock vegetation and leads to your own personal boathouse. This incredible, covered boat dock features both electric and water access, plus a boat lift for effortless access to the scenic, expansive Lake Jesup. Enjoy relaxing on the screened lanai or the open paver patio while enjoying the sounds of nature. NEW ROOF IN 2024 (House and Boat Dock), NEW PORCH ROOF 2025, NEW WATER HEATER 2025, NEW A/C 2021, FRESHLEY PAINTED 2021, RAIN GUTTERS 2020. Relish your time at the private community fishing pier, tennis court, take a dip in the gorgeous community pool or enjoy the splash pad. Lawn Maintenance is even included in your HOA (Lawncare includes mowing of lawn, trimming of bushes and fertilizer). Parkstone is a gated community with walking trails, scenic ponds, tennis court, community dock, two playgrounds, a splash pad and community pool to enjoy. The Cross Seminole Trail borders Parkstone and you are just a short walk from Central Winds Park, the Dog park and the Newly opened Pickleball Facility! Minutes from grocery stores, The Town Center, shopping and dining, this home has it all! Welcome home!
Listing is courtesy of: SHORESTONE PROPERTY GROUP (407-452-9818)
Listing Agent: Tania Crandall (407-452-9818)
1024 DINERO DR, WINTER SPRINGS, FL 32708
$419,00053 Days on yellowkey MLS ID: O6404240
REDUCED by $5,000 (1.2%) on 06/17/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1463 Built: 1986Monthly Fee: $29 Tax: $4,882 (2024)Community: Sunrise Estates Unit 2Spa: YesSingle Family
Taxes:$4,882
Remarks: Beautiful 3-bedroom, 2-bath pool/spa home located in the highly desirable Sunrise Estates in Winter Springs, featuring a split floor plan on nearly ¼ acre with no front neighbors for added privacy. This home boasts a newer roof and newer pool/spa heater, making it perfect for entertaining family and friends, while the oversized backyard and large covered screened-in patio provide an ideal outdoor living space. Inside, enjoy a wood-burning fireplace for warmth and ambiance on cooler evenings, along with no carpet throughout for easy maintenance. Sunrise Estates offers open parks, tennis courts, basketball courts, and softball fields, and is zoned for A-rated Seminole County schools, making it perfect for a growing family. Conveniently located near major highways, dining, shopping, and just minutes from Oviedo and Winter Park—schedule your private tour today!
Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)
Listing Agent: Antonio Salinger (407-304-9867)
1204 SWAN ST, WINTER SPRINGS, FL 32708
$624,0007 Days on yellowkey MLS ID: O6417440
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3334 Built: 1973 Tax: $3,677 (2024)Community: Winter Spgs Unit 4Spa: YesSingle Family
Taxes:$3,677
Remarks: Rare opportunity in the heart of Winter Springs! Situated on an expansive 0.72-acre lot with NO HOA, this unique 4-bedroom, 2.5-bath pool home offers endless potential for the buyer seeking space, privacy, and the chance to create something truly special. The property features a recently resurfaced pool, a fully fenced backyard, and an incredible outdoor setting designed for entertaining and enjoying Florida living. One of the standout features is the detached pizza kitchen gazebo, perfect for hosting family and friends, along with an additional outbuilding complete with A/C, power, and plumbing—ideal for a workshop, studio, home office, hobby space, or future guest accommodations. Mature landscaping and abundant outdoor space provide room for recreation, gardening, boats, RVs, and more. Inside, the home offers a functional layout with tremendous upside. While cosmetic updates could enhance the property's full potential, the major features, lot size, and unique amenities make this a rare find in Winter Springs. Whether you're looking for a personal residence, multi-generational living setup, or an investment opportunity, this property is ready for your vision.
Listing is courtesy of: EXIT REALTY PREMIER LEGACY (407-801-8219)
Listing Agent: Chandler Williams (407-702-3815)
1441 FOREST HILLS DR, WINTER SPRINGS, FL 32708
$420,0007 Days on yellowkey MLS ID: O6413957
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1731 Built: 1985Monthly Fee: $90 Tax: $2,546 (2025)Community: Wedgewood Tennis VillasSingle Family
Taxes:$2,546
Remarks: Welcome to this beautifully maintained and updated 3 bedroom, 2 bath home with a 2-car garage, ideally situated in the highly desirable Tuscawilla community of Winter Springs. Offering a combination of modern updates, timeless character and serene waterfront views, this move in ready home is a rear find. Step inside to discover an inviting floor plan, featuring ceramic tile and laminate flooring throughout, providing both style and easy maintenance. The updated kitchen is designed for everyday living and entertaining, complete with modern cabinetry, stainless steel appliances, granite countertops, with a black side by side refrigerator, skylight that fills the space with natural light and a built-in wine rack for added charm. The spacious family room serves as the heart of the home, highlighted by a striking brick wood burning fireplace and elegant exposed wood beams that adds warmth and architectural character. Sliding glass doors create a seamless connection between the indoor living spaces and the outdoors while framing beautiful views of the pond. Relax and unwind in the screened in porch overlooking the tranquil water, where you can enjoy peaceful mornings, evening sunsets and the beauty of Florida's natural surroundings. The primary suite and additional bedrooms offer comfortable living spaces, with sliding glass door access providing abundant natural light and picturesque views. The home also offers valuable peace of mind with major updates already completed, including a new roof installed in 2022 and a new HVAC system installed in 2021. Located in the sought after Tuscawilla community, residents enjoy convenient access to parks, walking trails, golf, tennis facilities, shopping, dining, and top rated Seminole County schools. Whether you are looking for your forever home or a peaceful retreat, this waterfront gem delivers comfort, convenience and lasting value. Don't miss your opportunity to own this beautifully updated pond-view home in one of Winter Springs' most desirable neighborhood.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Karen Khairullah-Wallace (407-256-3465)
811 MAPLE LEAF LOOP, WINTER SPRINGS, FL 32708
$545,00019 Days on yellowkey MLS ID: O6413927
0 Days Off yellowkey (back on 6/16/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2852 Built: 2016Monthly Fee: $100 Tax: $4,089 (2025)Community: Seven OaksSpa: NoSingle Family
Taxes:$4,089
Remarks: Explore 811 Maple Leaf Loop, recently enhanced with fresh interior paint. The kitchen includes a functional island, and the primary bathroom provides double sinks for practical use, a walk in closet and convenience of a separate tub and shower. Beyond the interior, exterior grounds feature a covered patio and a fenced in backyard. Discover modern comfort and practical living in this updated residence. Included 100-Day Home Warranty with buyer activation
1112 ORANGE AVE, WINTER SPRINGS, FL 32708
$3,998,000439 Days on yellowkey MLS ID: O6298615
Bed: 5 Bath: 6.5 Gar: 6 Liv Area Sq Ft: 8685 Built: 2008 Tax: $14,976 (2024)Community: Lake JessupSpa: YesSingle Family
Taxes:$14,976
Remarks: Opportunities like this are almost impossible to find in Central Florida. Situated on 5.33 pristine lakefront acres with no HOA, this extraordinary estate is commercially zoned, creating a unique opportunity for a variety of potential business uses, including a luxury wedding venue, private event space, corporate retreat, boutique hospitality concept, or an exceptional live-work estate. With its breathtaking setting, grand architecture, and resort-style amenities, the property offers a level of versatility rarely available in today's market. Inspired by the elegance of the Italian countryside, the residence makes a lasting first impression with a dramatic front waterscape, lush gardens, and timeless architectural details. Inside, guests are welcomed by a grand foyer featuring exquisite marble finishes and a spectacular custom-painted 24-karat gold dome. Designed for both entertaining and everyday luxury, the expansive living spaces showcase panoramic views of beautiful Lake Jessup, soaring ceilings, stunning chandeliers, and a grand marble fireplace. The thoughtfully designed "H" floor plan encompasses more than 8,000 square feet of air-conditioned living space, offering five spacious bedrooms and six-and-a-half bathrooms, all conveniently situated on a single level. The primary suite is a true private retreat, featuring eight sets of French doors opening directly to the pool and lakefront, a custom-designed closet that doubles as a safe room, and a spa-inspired bathroom complete with a tranquil garden retreat. The gourmet chef's kitchen is equipped with top-of-the-line appliances, custom cabinetry, and an oversized walk-in butler's pantry designed to accommodate large-scale entertaining. Additional luxury amenities include a temperature-controlled wine cellar, private movie theater, dedicated nanny or guest quarters, and a six-car garage with extensive attic storage. Outside, the estate transforms into a private resort. A spectacular sports pool with multiple water features serves as the centerpiece, complemented by a summer kitchen, wet bar, outdoor fireplace, and expansive covered veranda overlooking the serene waters of Lake Jessup. Whether hosting elegant weddings, unforgettable events, corporate gatherings, or private family celebrations, the setting is simply unmatched. Combining custom craftsmanship, Tuscan and Greek-inspired design elements, commercial zoning flexibility, and an irreplaceable waterfront location, this remarkable estate offers a truly rare opportunity to own one of Central Florida's most unique properties. Schedule your private tour today to experience the endless possibilities and extraordinary lifestyle this one-of-a-kind property provides.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Brian Hyser (407-951-2472)
613 BONITA RD, WINTER SPRINGS, FL 32708
$719,00078 Days on yellowkey MLS ID: O6395444
REDUCED by $20,000 (2.7%) on 06/03/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3281 Built: 2016 Tax: $8,389 (2025)Community: North Orlando Ranches Sec 02ASingle Family
Taxes:$8,389
Remarks: Under contract-accepting backup offers. Nestled beneath a canopy of mature trees in a charming ranch-style setting in Winter Springs, this custom-built 2016 Craftsman blends timeless architecture with today’s most sought-after design features. From the expansive front porch to the bright open-concept floor plan, every detail was designed for modern living and effortless entertaining. The chef-inspired kitchen serves as the heart of the home with quartz countertops, an oversized 9-foot center island, soft-close wood cabinetry, stainless steel appliances, and a massive walk-in pantry ideal for storage and organization. A dramatic 4-panel sliding glass door opens to the spacious wood deck and fully fenced backyard, creating seamless indoor-outdoor living perfect for gatherings, relaxing evenings, and Florida entertaining. The first-floor primary suite is a private retreat featuring a spa-style bath with a clawfoot soaking tub, oversized rain-head shower, dual vanities, and an expansive walk-in closet. Additional highlights include spacious secondary bedrooms, flexible loft space, abundant natural light, and quality craftsmanship throughout. Conveniently located near major highways, top-rated schools, shopping, dining, hospitals, and everyday conveniences, this exceptional Winter Springs home offers the ideal balance of peaceful surroundings and central Florida accessibility
Listing Agent: Victoria Myers (407-401-3249)
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