Location: Winter Springs
Do Not Show Listings
1208 CHEETAH TRL, WINTER SPRINGS, FL 32708
$669,9006 Days on yellowkey MLS ID: O6416652
0 Days Off yellowkey (back on 6/20/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2837 Built: 1979 Tax: $3,887 (2025)Community: Tuscawilla Unit 06Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,887
Elementary School: Keeth Elementary
High School: Winter Springs High
Tax Year: 2025
Middle School: Indian Trails Middle
Remarks: Under contract-accepting backup offers. Come fall in love with this versatile 5 bedroom 3 bath home on over 1/2 acre beautifully landscaped property with lush trees and gardens....your very own private oasis in the heart of Tuscawilla! With two large master suites, two spacious guest bedrooms plus a fifth bedroom/ home office with exterior door, the opportunities are endless! In addition, most of the home is very tastefully handicapped accessible. Tinker in your oversized 2 car garage, take a stroll to the neighborhood park or the country club, or sit on your covered back porch watching nature dance in your gorgeous and private backyard. Perhaps you could just float in your recently resurfaced screened, solar heated pool with artful brick paver deck and outdoor shower. Rest easy with a newer roof (2025) two new AC systems (2026 and 2024) updated plumbing, complete window replacement and gorgeous new sliding doors. Your parents, guests or special needs family member will enjoy the massive secondary primary suite with tasteful and versatile handicapped accesible bathroom with roll in shower,double sink vanity, and large accessible walk in closet. Tons of storage is found throughout the home including in the oversized laundry room with utility sink, and cabinets galore. Hey, imagine peace and quiet in a potentially chaotic household…. The main primary bedroom is completely separate from all of the others and includes a walk-in closet and a space large enough for all your dressers, nightstands and even a quiet sitting area to enjoy your favorite book. The ensuite Primary bath has Double doors, updated double vessel sinks and other delightful upgrades. As a bonus, you can open your sliding doors in your bedroom to the pool for a moonlight dip! Newer wood ceilings adorn the rear covered porch for daydreaming or making entertaining special. Guests, family and friends will appreciate the additional parking on the expansive driveway (we just know you're going to have a lot of company). Trotwood Park is a fun place to experience the farmer's market and your kiddos can get to school without accessing the major roads!! Tuscawilla isn't just a place to live.....it's a place to call home. This is truly a once in a lifetime opportunity at a very reasonable price. Hurry to see it now before someone else snatches it up!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Colleen Kahl (407-630-0027)
1201 WOLVERINE TRL, WINTER SPRINGS, FL 32708
$500,000158 Days on yellowkey MLS ID: O6374676
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1979 Built: 1977 Tax: $5,709 (2024)Community: Winter Spgs Unit 4Single Family
Taxes:$5,709
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Welcome to this charming 4-bedroom, 2-bath home tucked away in a quiet, tree-lined neighborhood in desirable Winter Springs. Surrounded by mature trees, this property offers a peaceful atmosphere and a spacious backyard, ideal for entertaining, relaxing, or enjoying Florida outdoor living. Inside, you’ll find a warm and inviting layout highlighted by an original masonry fireplace, adding timeless character and charm. Skylights in the living room and hallway flood the home with natural light, creating a bright and airy feel throughout the main living spaces. Conveniently located near schools, parks, shopping, dining, and major roadways, this home offers the perfect blend of tranquility and accessibility in an established community.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Nairobi Rondon (786-935-0365)
724 BARRINGTON CIR, WINTER SPRINGS, FL 32708
$399,900398 Days on yellowkey MLS ID: O6312092
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1450 Built: 1987Monthly Fee: $120 Tax: $1,771 (2024)Community: Georgetowne Unit 1Single Family
Taxes:$1,771
Remarks: Very well maintained home in Tuscawilla! Updated kitchen with Granite countertops, Elegant mirrored wall, Ceramic Tile throughout. Double sinks in beautiful master bathroom with garden shower tub! Owners. Replace all new appliance, have access to the neighborhood clubhouse and Community pool, HOA takes care of front yard lawn maintenance. Two parks and a nature, trail are walking distance from the home. Walk to Trotwood Park and to Tuscawilla Country Club for a round of golf or tennis or to just socialize at the café and bar. This is a great opportunity to own an adorable low maintenance single-family home in the most affordable sought-after Country Club community in Seminole county. A rated school district! Short drive to Oviedo Marketplace and restaurants! Seller willing to contribute $2000 towards closing costs!! Don't miss this opportunity!! --
Listing is courtesy of: DIAMOND 2000 REALTY, INC (321-231-4195)
Listing Agent: Ramon Ortiz Cruz (321-231-4195)
221 SHERRY AVE, WINTER SPRINGS, FL 32708
$359,90049 Days on yellowkey MLS ID: O6404854
REDUCED by $7,000 (1.9%) on 06/17/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1700 Built: 1971 Tax: $523 (2025)Community: North Orlando Townsite Fourth Add ReplatSingle Family
Taxes:$523
Remarks: Beautiful fully renovated property featuring 4 spacious bedrooms, 2 modern bathrooms, and an additional room perfect for an office or play room. The home has been completely updated, including a new roof and new windows, providing improved energy efficiency and peace of mind. Open layout with excellent natural light and modern finishes throughout. Move-in ready, ideal for a family home or investment opportunity. Conveniently located with easy access to schools, shopping, and major roads.
Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)
Listing Agent: Rodrigo Chavez (407-652-8430)
203 SWEETGUM, WINTER SPRINGS, FL 32708
$420,0006 Days on yellowkey MLS ID: O6417974
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1218 Built: 1973 Tax: $925 (2025)Community: North Orlando Terrace Unit 2 Sec 8Spa: NoSingle Family
Taxes:$925
Remarks: This meticulously maintained home offers an impressive combination of recent upgrades, thoughtful features, and exceptional outdoor living. The curb appeal is enhanced by professional landscape lighting, while 10-foot access gates on both sides of the property provide convenience and flexibility. A three-zone irrigation system helps maintain the beautifully landscaped grounds year-round. The backyard is designed for relaxation and enjoyment, featuring a sparkling pool with a removable safety fence, a LED pool light replaced in 2025, and a new pool pump and filter installed in 2026. For additional storage, workshop space, or hobby use, the property also includes a substantial 12’ x 20’ steel accessory building. No HOA, so bring your toys, Rv, camper etc! Inside, the garage has been refreshed with newly painted floors and walls and is illuminated by six custom LED light fixtures, creating a bright and functional space. Major system updates provide peace of mind, including a new roof installed in March 2026, a new central air conditioning system installed in March 2025, and a new hot water heater installed in May 2026. Additional recent improvements include a refrigerator replaced in 2024, a dishwasher installed in 2024, a garbage disposal added in 2025, a Google Nest smart thermostat installed in 2026, and an updated master bathroom toilet. With extensive recent improvements, modern conveniences, and pride of ownership evident throughout, this move-in-ready home offers outstanding value and is ready for its next owner to enjoy.
Listing is courtesy of: CENTURY 21 ALTON CLARK (407-636-4637)
Listing Agent: Joseph Connolly (631-365-6085)
1406 BLUMBERG BLVD, WINTER SPRINGS, FL 32708
$420,00038 Days on yellowkey MLS ID: O6408695
REDUCED by $5,000 (1.2%) on 06/19/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1476 Built: 2024Monthly Fee: $356 Tax: $6,076 (2025)Community: Hickory Grove TwnhmsTownhouse
Taxes:$6,076
Elementary School: Layer Elementary
Remarks: Welcome to this almost-new townhome in beautiful Winter Springs! Located in the desirable Hickory Grove community, where you will find a maintenance free living, relaxing pool and cabana, playground for the little ones and a dog park for your furry friend, all just a few steps away and NO CDD to pay. The monthly HOA dues also include: landscaping, irrigation, weed control, exterior paint, roof, 1GB of high speed internet and cable premium package. This stunning residence has been tastefully decorated and offers the perfect blend of modern style, comfort, and convenience. Your front door opens up to the serene parks, fountains and walkways just across the street from your favorite stores and restaurants. Enjoy an open-concept layout with plenty of natural light, a modern kitchen with state of the art SS appliances, quartz counters and a beautiful island to entertain your guests. 3 bedrooms, 2.5 bathrooms, and a 2-car garage, and much more. This home is move-in ready and designed for easy living. Upstairs, the generous primary suite offers a private retreat with an en-suite bath and ample closet space. Built with today’s lifestyle in mind, this home also includes the peace of mind of a builder warranty, this is a fantastic opportunity to own a like-new home in one of Central Florida’s most sought-after areas with top-rated schools.
Listing is courtesy of: RALISTO, LLC (407-493-6032)
Listing Agent: Kalex Espinosa (407-493-6032)
270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$249,900225 Days on yellowkey MLS ID: O6359666
REDUCED by $9,100 (3.5%) on 06/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1089 Built: 1994Monthly Fee: $121 Tax: $327 (2024)Community: Deersong 2Spa: NoSingle Family
Taxes:$327
Remarks: Price Improvement to $259,000 * Quick Closing Available. Welcome to 270 San Gabriel Street in Winter Springs—now offered at an updated price and ready for its next owner. This well-maintained, single-story home features vaulted ceilings and a bright, open layout that creates a comfortable and inviting living space. With neutral finishes and ceramic tile flooring throughout, the home is truly move-in ready. All appliances are included for added convenience. Enjoy morning coffee or unwind in the evening on the oversized screened patio, offering a private outdoor retreat. Additional exterior storage provides practical space for bikes, tools, and seasonal items. Located just minutes from the scenic Cross Seminole Trail, the Deersong community also offers access to a pool and cabana for residents to enjoy. Nearby parks, shopping, dining, and top-rated Seminole County schools add to the home’s appeal. Considering making a move to downsize? First-time homebuyer? investor? or seeking a low-maintenance second home in Central Florida? Schedule your private showing today. With a newly reduced price and quick closing available, this is an excellent opportunity to own a well-cared-for home in a desirable location..
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Alie Gattis (407-760-1488)
1126 TROTWOOD BLVD, WINTER SPRINGS, FL 32708
$460,000130 Days on yellowkey MLS ID: O6382859
REDUCED by $10,000 (2.1%) on 06/20/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2066 Built: 1991Monthly Fee: $11 Tax: $5,998 (2024)Community: Oak Forest Unit 8Single Family
Taxes:$5,998
Remarks: Virtually Staged. Top-Rated Schools! Beautiful and well-maintained 4-bedroom, 2-bath home located in desirable Winter Springs. This home features ceramic tile flooring throughout for easy maintenance and a spacious layout perfect for comfortable living. Enjoy a huge patio—ideal for family gatherings and entertaining guests. Brand new roof (2025) provides peace of mind for years to come. Prime location close to shopping, restaurants, and supermarkets, offering both convenience and lifestyle.
Listing is courtesy of: JOY ESTATE ENTERPRISE INC (321-754-9131)
Listing Agent: Joyce Tang (407-666-9388)
618 LOCUST CT, WINTER SPRINGS, FL 32708
$228,80037 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
Taxes:$4,436
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)
424 FLATWOOD DR, WINTER SPRINGS, FL 32708
$525,00044 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
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
$499,99957 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
$879,0008 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)
299 WOODGREEN LN, WINTER SPRINGS, FL 32708
$285,00062 Days on yellowkey MLS ID: O6401276
REDUCED by $5,000 (1.7%) on 05/14/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1326 Built: 1990Monthly Fee: $190 Tax: $2,091 (2025)Community: Mount Greenwood Unit 4 OfTownhouse
Taxes:$2,091
Remarks: Welcome to this BEAUTIFULLY UPDATED 3-bedroom, 2.5-bath townhome in the PEACEFUL Mount Greenwood community of Winter Springs, where modern upgrades and a thoughtfully designed layout create a truly inviting place to call home. As a CORNER UNIT, this residence enjoys added privacy along with a serene setting, including POND VIEWS just beyond the rear fence, best appreciated from the upstairs bedrooms. Step inside to discover an OPEN and SPACIOUS FLOOR PLAN filled with NATURAL LIGHT, enhanced by LUXURY VINYL PLANK FLOORING (2020) throughout the main level. The Kitchen is both stylish and functional, featuring STAINLESS STEEL APPLIANCES, white cabinetry, a sleek tile backsplash, a closet pantry, and a convenient laundry closet. A PASS-THROUGH WINDOW connects the Kitchen to the Dining Room, creating an easy flow for everyday living and entertaining. The Dining area seamlessly transitions into the generous Living Room, where NEWER DOUBLE DOORS WITH BUILT-IN BLINDS (2022) open to the screened patio, offering a relaxing indoor-outdoor connection. The back and side yards have been thoughtfully designed for LOW MAINTENANCE, with no grass to cut, all enclosed within a NEW WOOD FENCE (2024)—perfect for enjoying quiet evenings or weekend gatherings. A HALF BATH on the main floor adds convenience for guests. Upstairs, the Primary Suite provides a comfortable retreat, complete with an en suite bath featuring a step-in shower and UPDATED VANITY WITH GRANITE COUNTERTOP (2020). Two additional Bedrooms offer flexibility for family, guests, or a home office. These rooms are currently connected but include a framed opening that can easily be closed off to create TWO FULLY SEPARATE SPACES. A second full bath with UPDATED TILE (2023) serves the additional bedrooms. This home has been meticulously maintained and updated with major improvements, including a NEW HVAC SYSTEM (2024), NEW WATER HEATER (2023), and a NEWER ROOF (2019)—providing both style and peace of mind. Residents of Mount Greenwood enjoy LOW HOA fees and access to amenities including a community pool, playground, and included trash service, all within a friendly and WELL-KEPT NEIGHBORHOOD. IDEALLY LOCATED near Central Winds Park and Winter Springs Town Center, you’ll have EASY ACCESS to outdoor recreation, shopping, and dining. The home is also zoned for HIGHLY REGARDED SCHOOLS and offers convenient access to State Road 417, making commuting to Orlando and surrounding areas simple. With its stylish updates, low-maintenance outdoor space, and DESIRABLE LOCATION this Mount Greenwood townhome brings the perfect blend of comfort, convenience, and easy Florida living. Call and schedule your showing today!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
600 NORTHERN WAY #302, WINTER SPRINGS, FL 32708
$269,90078 Days on yellowkey MLS ID: O6396912
1 Days Off yellowkey (back on 6/19/2026)
REDUCED by $5,100 (1.9%) on 06/03/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1425 Built: 1981 Tax: $4,268 (2025)Community: Tuscany Place Ph 1Condo
Taxes:$4,268
Remarks: Under contract-accepting backup offers. Virtually Staged. Seller may consider buyer concessions if made in an offer ~ Welcome to Tuscany Place, a GATED COMMUNITY in the heart of Tuskawilla – one of Winter Springs’ most desirable and established areas! This UPDATED second-floor condo delivers the perfect blend of modern style, LOW MAINTENANCE LIVING, and an unbeatable Central Florida location. Major updates are already done for you, including the kitchen and both bathrooms, plus a NEWER A/C (2020), giving peace of mind from day one. Inside, the home has been tastefully updated with modern finishes and fixtures, creating a clean, MOVE-IN READY space that feels both fresh and inviting. WOOD LAMINATE FLOORING flows throughout the entire unit, enhancing the seamless, low-maintenance lifestyle. The OPEN CONCEPT living and dining area is filled with NATURAL LIGHT thanks to a wall of SLIDING GLASS DOORS that lead to a SCREENED BALCONY overlooking peaceful green space – perfect for morning coffee or winding down in the evening. The UPDATED KITCHEN stands out with a fresh, modern color palette and a pop of personality, featuring sleek countertops, STAINLESS STEEL APPLIANCES, ample cabinet storage, a breakfast bar, and a window that brings in even more natural light. The SPLIT BEDROOM layout offers both comfort and privacy with the primary suite tucked away at the back of the home, complete with a WALK-IN CLOSET, updated en-suite bath, and its own private access to a SECOND BALCONY. Two additional bedrooms are positioned at the front of the unit and share a beautifully updated full bath, ideal for guests, family, or a home office setup. Tuscany Place residents enjoy a gated entrance along with added conveniences like lawn care and pest control, making this a truly low-maintenance option. The location is hard to beat – just minutes from Tuskawilla Road, SR 434, and 417, with easy access to TROTWOOD PARK, Central Winds Park, Tuscawilla Country Club, and all the shopping and dining options in Winter Springs and nearby Oviedo. Whether you are looking for your next home or a smart investment, this updated condo is priced to sell and ready for its next owner. Call today to schedule a tour!
472 DEWARS CT, WINTER SPRINGS, FL 32708
$499,90021 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
$539,9009 Days on yellowkey MLS ID: O6414948
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
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.
71 BOMBAY AVE, WINTER SPRINGS, FL 32708
$215,90021 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
$569,90069 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)
335 KIRKCALDY DR, WINTER SPRINGS, FL 32708
$329,90051 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)
4431 BROOK HOLLOW CIR, WINTER SPRINGS, FL 32708
$220,000161 Days on yellowkey MLS ID: O6374194
REDUCED by $10,000 (4.3%) on 06/09/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1367 Built: 1989Monthly Fee: $275 Tax: $2,878 (2024)Community: Deer Run Unit 19ATownhouse
Taxes:$2,878
Remarks: Welcome home to 4431 Brook Hollow Circle, where clean design meets comfortable living. This light-filled residence offers an open, airy layout that feels both spacious and welcoming, with neutral finishes that create a fresh, move-in-ready atmosphere. The living and dining areas flow seamlessly, making everyday living and entertaining effortless. One of the home’s standout features is the enclosed back porch, providing a versatile extension of the living space—perfect for morning coffee and relaxing evenings. The porch overlooks a peaceful outdoor area, offering privacy and a sense of calm rarely found. is ideal for those seeking a clean, uncluttered space that feels comfortable and functional. Conveniently located in Winter Springs, this property combines easy living with a tranquil setting. Nearby Attractions: Central Winds Park & Lake Jesup – Large park with trails, sports fields, and lake views Cross Seminole Trail – Popular walking and biking trail nearby Torcaso Cove Park – Playground, splash pad, and family-friendly amenities Overlook Park (Oviedo) – Boardwalks, fishing pier, and scenic lake views Central Florida Zoo & Botanical Gardens (Sanford) – Easy family day trip Winter Springs Town Center – Community events, dining, and festivals Winter Park (20–25 min drive) – Scenic Boat Tour, museums, shopping, and dining With its open interior, thoughtful layout, and inviting indoor-outdoor connection, this home
Listing Agent: Nicolas Merino (954-226-4314)
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