Location: Winter Springs , 32708
Do Not Show Listings
1406 BLUMBERG BLVD, WINTER SPRINGS, FL 32708
$420,00033 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,076
Elementary School: Layer Elementary
High School: Winter Springs High
Tax Year: 2025
Middle School: Indian Trails Middle
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)
1326 TARFLOWER DR, WINTER SPRINGS, FL 32708
$435,0001 Day on yellowkey MLS ID: O6416617
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1678 Built: 2025Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory Grove TwnhmsTownhouse
Taxes:$1,457
Remarks: Welcome to 1326 Tarflower Drive, a stunning 2025-built townhome located in the highly sought-after Hickory Grove community in Winter Springs. Perfectly positioned on one of the most desirable lots in the neighborhood, this rare corner-unit offers exceptional privacy, abundant natural light, and beautiful green space views. With no neighboring building on one side, two mature magnolia trees, and no directly facing homes behind, this home provides a bright, open, and peaceful setting that is hard to find. Inside, you'll find an open-concept floor plan featuring wood-look plank tile flooring, a spacious living room, dedicated dining area, and a beautifully appointed kitchen complete with a large peninsula island, marble countertops, modern cabinetry, and upgraded Charcoal stainless steel appliances—a premium upgrade not typically found. The first floor also features a convenient drop zone and half bath. Upstairs offers four spacious bedrooms, providing flexibility for guests, a home office, nursery, or playroom. The primary suite is filled with natural light and features dual vanities, a large walk-in shower, private water closet, and an walk-in closet. A guest bathroom with dual sinks and a tiled tub/shower combination serves the additional bedrooms. Residents of Hickory Grove enjoy amenities including a community pool, playground, and dog park. The HOA also includes high-speed fiber internet and cable, providing added value and convenience. Located just steps from Winter Springs Town Center, you'll enjoy walkable access to Publix, restaurants, shopping, and everyday conveniences. Central Winds Park, Winter Springs High School, Tuskawilla Road, and SR-417 are all just minutes away. Opportunities to own a premium corner-unit in one of Winter Springs' newest communities are rare. Combining modern construction, upgraded finishes, privacy, natural light, and an unbeatable location, this move-in-ready home is one you won't want to miss.
Listing is courtesy of: DOUGLAS EDMUND REAL ESTATE LLC (407-853-4402)
Listing Agent: Yuly Rodriguez (407-879-0720)
200 BLUE CREEK DR, WINTER SPRINGS, FL 32708
$625,0003 Days on yellowkey MLS ID: O6416327
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2344 Built: 1997Monthly Fee: $70 Tax: $3,467 (2025)Community: Chestnut Estates Ph 2Single Family
Taxes:$3,467
Elementary School: Lawton Elementary
High School: Oviedo High
Remarks: Virtually Staged. Meticulously maintained and beautifully positioned with peaceful conservation and pond views, this 4-bedroom, 3-bathroom home in Chestnut Estates offers 2,344 square feet of spacious single-story living in the desirable Tuscawilla area. Set on an oversized 0.26-acre lot with no rear or side neighbors, this property combines a versatile floorplan, generous living spaces and inviting indoor-outdoor living. Inside, high ceilings and tons of natural light create a bright, open feel throughout the heart of the home. The layout includes a formal dining room with tray ceiling, a front living/flex room with French doors, a spacious family room and an open kitchen with granite countertops, stainless steel appliances, breakfast bar, pantry, and a sunny breakfast nook overlooking the backyard and conservation. The thoughtfully designed split-bedroom floorplan offers both privacy and flexibility. The tucked away primary suite features direct access to the screened rear porch, a large walk-in closet, dual vanities, a garden tub, and a separate shower. Two secondary bedrooms share a spacious Jack-and-Jill style bathroom with an oversized vanity and abundant storage, while the fourth bedroom is positioned near the third full bathroom, which features a walk-in shower and direct porch access. Outdoor living truly shines with a covered screened porch, custom paver patio and firepit area, mature landscaping, aluminum fencing, and peaceful pond and conservation views. The larger lot and natural backdrop create a peaceful setting for relaxing or entertaining. Pride of ownership is evident throughout, with major improvements including a new roof in 2024, Goodman HVAC system in 2021, updated outdoor living spaces, enhanced landscaping and drainage improvements, and consistent preventative maintenance over the years. Conveniently located near Tuscawilla Country Club, parks, shopping, dining, major roadways, and Seminole County schools, this well-cared-for home offers space, privacy, and an exceptional opportunity to enjoy comfortable living in a beautifully maintained home with a setting that’s becoming increasingly difficult to find. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Amanda Meyer (201-406-2900)
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
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)
173 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$439,990108 Days on yellowkey MLS ID: O6386437
0 Days Off yellowkey (back on 6/18/2026)
REDUCED by $45,000 (9.3%) on 06/01/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1704 Built: 2026Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Remarks: Under Construction. With an open concept ground floor and spacious living areas, the Sofia is ideal for entertaining and everyday life. Dedicated as an end unit, this floorplan features 3 bedrooms, 2.5 bathrooms and a rear-loading 2-car garage. The 2nd floor features a loft, abundant storage, and laundry space. Located on the 1st floor, the owner's suite that has it all - a spacious walk-in closet, great natural light, and private bath. Stainless steel appliances, a walk-in pantry and a breakfast bar are all featured in this floorplan's thoughtfully designed kitchen.
Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)
Listing Agent: Amanda Warren (321-662-0779)
161 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$444,990108 Days on yellowkey MLS ID: O6386458
REDUCED by $40,000 (8.2%) on 06/01/2026
Remarks: Under Construction. A standout feature of this end-unit home is the owner’s suite, conveniently located on the first floor, providing privacy and ease of access. This inviting retreat includes abundant natural light, a generous walk-in closet, and a well-appointed private bath. The open-concept main floor features expansive living and dining areas that flow seamlessly into a thoughtfully designed kitchen—complete with stainless steel appliances, including a refrigerator, a walk-in pantry, and a spacious breakfast bar—ideal for entertaining or everyday living. Laundry room, complete with washer and dryer is conveniently located on the main floor. Upstairs, you’ll find two additional bedrooms, a versatile loft perfect for a home office or media space, along with ample storage and a dedicated laundry area. A rear-loading 2-car garage adds both functionality and curb appeal. Located in desirable Winter Springs near the vibrant Town Center, residents enjoy a highly sought-after lifestyle with walkable access to shopping, dining, and community events. Known for its top-rated schools, scenic parks, and extensive trail system, Winter Springs offers a perfect balance of small-town charm and modern convenience—just a short drive from Orlando. Discover low-maintenance townhome living in one of Central Florida’s most connected and livable communities.
4209 LORI LOOP, WINTER SPRINGS, FL 32708
$625,00042 Days on yellowkey MLS ID: O6406486
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2428 Built: 1986Monthly Fee: $17 Tax: $6,046 (2024)Community: Willow RunSingle Family
Taxes:$6,046
Elementary School: Red Bug Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: Tuskawilla Middle
Remarks: Professional Photos Coming Soon! New Roof Being Installed June 17, 2026! A home this loved is hard to find. Lovingly maintained and thoughtfully improved over the years, this traditional 4-bedroom, 3-bath heated saltwater pool home in the desirable Willow Run community of Winter Springs showcases true pride of ownership throughout. The desirable three-way split floor plan offers exceptional privacy and flexibility for families, guests, multi-generational living, or a home office setup. Surrounded by lush, mature landscaping cultivated with care, this Seminole County pool home blends timeless character with thoughtful updates designed for comfortable everyday living and effortless entertaining. Freshly painted throughout, the interior offers a bright, clean backdrop ready for your personal style. Newer windows fill the home with natural light, while solid wood bedroom doors add warmth and quality craftsmanship throughout. The spacious family room is anchored by a classic wood-burning fireplace, creating an inviting gathering space for family and friends. Major updates provide valuable peace of mind, including a newer HVAC system (2020) with Blue Light air purification and service contract, Water Heater (2026), and a brand-new roof being installed June 17, 2026. Florida outdoor living takes center stage with a heated saltwater pool, safety fence, expansive stone-finished pool deck, oversized rear porch, widened driveway, charming front porch, and decorative wrought iron fencing. Whether hosting gatherings, tending the garden, relaxing poolside, or enjoying year-round outdoor living, this property offers the lifestyle many Central Florida buyers are seeking. Located in the heart of Winter Springs, this home offers exceptional convenience with quick access to SR-417, making commuting throughout Central Florida a breeze. Residents enjoy proximity to Winter Springs Town Center, Tuscawilla Country Club, Central Winds Park, the Cross Seminole Trail, shopping, dining, and highly regarded Seminole County schools. Winter Park is approximately 20 minutes away, while Orlando's major theme parks and Florida's east coast beaches can be reached in about 55 minutes, providing easy access to some of the region's most popular destinations. If you're searching for a meticulously maintained pool home in Winter Springs with major updates already completed, exceptional outdoor living spaces, and a location that combines convenience with community, this Willow Run gem deserves your attention. Schedule your private showing today.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Laura Leigh Wood (407-310-4908)
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)
600 NORTHERN WAY #502, WINTER SPRINGS, FL 32708
$249,900464 Days on yellowkey MLS ID: O6286935
REDUCED by $15,100 (5.7%) on 06/18/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1425 Built: 1985Monthly Fee: $397 Tax: $766 (2024)Community: Tuscany Place Ph 1Spa: NoCondo
Taxes:$766
Elementary School: Keeth Elementary
Remarks: MOTIVATED SELLER!!! Seller offering concession toward buyer closing cost. Location! Location! Location! This pristine condo nestled in the heart of Tuscawilla offers an incredible opportunity for low maintenance living in a serene and gated community. Enjoy summer days by the beautiful community pool and relax in the cabana. Across the way you will find access to Trotwood Park, with its picturesque settings ideal for picnics and recreational activities. Featuring a pavilion, playground, splash pad, tennis courts, and sports fields, it's a hub for family fun. For outdoor enthusiasts, the nearby Seminole County Cross Trail is perfect for biking and walking. As you tour the well maintained 3-bedroom, 2-bathroom condo, it encompasses 1425 sqft of second level living with private screened balconies overlooking the courtyard. Well-appointed kitchen equipped with brand-new stainless-steel appliances: Counter-depth Smart French Door Refrigerator, Smart SLIM Microwave, Bespoke Induction Range with self and steam cleaning Air Fry Convection Oven. A generous living and dining area that are inviting and ideal for entertaining. The split floor plan offers privacy for the owner suite, complete with its own screened balcony. The secluded and spacious secondary bedrooms are delightful for guests, office space or a growing family. New AC installed 7/2025 (16 seer AC unit with 1 year maintenance and 10yr-parts/2yr-labor). Families are drawn to the area thanks to its top-rated schools, making this condo not just a home, but a gateway to a vibrant community. Recently refreshed and ready for its new owners to display their personal touches.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Bob Bretz, Pa (407-797-9500)
1702 DAVENPORT CT, WINTER SPRINGS, FL 32708
$569,90064 Days on yellowkey MLS ID: O6398359
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
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
Elementary School: Highlands Elementary
Middle School: South Seminole Middle
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)
724 BARRINGTON CIR, WINTER SPRINGS, FL 32708
$399,900393 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 Tuskawilla! Updated kitchen with Granite countertops, Elegant mirrored wall, Ceramic Tile throughout. Double sinks in beautiful master bathroom with garden shower tub! Owners 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 Tuskawilla 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)
4431 BROOK HOLLOW CIR, WINTER SPRINGS, FL 32708
$220,000156 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)
4490 BROOK HOLLOW CIR, WINTER SPRINGS, FL 32708
$230,00046 Days on yellowkey MLS ID: O6405179
REDUCED by $15,000 (6.1%) on 06/18/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1359 Built: 1991Monthly Fee: $275 Tax: $2,913 (2024)Community: Deer Run Unit 19ATownhouse
Taxes:$2,913
Remarks: Welcome to 4490 Brook Hollow, a beautifully maintained property nestled in a quiet and desirable Florida community. This home offers the perfect blend of comfort, functionality, and Florida lifestyle living. Step inside to find a light-filled interior with an open and inviting floor plan, ideal for both everyday living and entertaining. The spacious living areas flow seamlessly into a well-appointed kitchen featuring ample cabinetry, generous counter space, and a layout designed for convenience. The primary suite provides a relaxing retreat with a private bath and ample closet space, while additional bedrooms offer flexibility for guests, a home office, or growing households. Outside, enjoy a peaceful setting with room to relax or entertain—perfect for enjoying Florida’s year-round sunshine. Whether you’re hosting gatherings or unwinding after a long day, this outdoor space delivers. Conveniently located near shopping, dining, major roadways, and local attractions, this home combines tranquility with accessibility. Don’t miss the opportunity to make this charming property your next home.
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
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)
314 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$279,990253 Days on yellowkey MLS ID: O6350799
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1091 Built: 1992Monthly Fee: $127 Tax: $2,209 (2024)Community: DeersongSpa: NoSingle Family
Taxes:$2,209
Remarks: **BUYER INCENTIVE AVAILABLE!! Preferred Lender is offering a COMPLIMENTARY TEMPORARY RATE BUY DOWN for qualified buyers on new loan locks completed on or before 6/30/26!!** Seller offering $2,500.00 toward Buyers Closing costs with an acceptable offer. Welcome to your dream home, perfectly positioned for easy commuting in Central Florida. This 3 bedroom, 2 full baths, split bedroom plan and screen enclosed side porch home boasts upgrades that make it shine brighter than most — capturing attention with these enhancements: Water Heater (Installed 03/2026), Roof (installed 2021) replaced in recent years for added peace of mind, insurance savings, and easier loan approval, Air Conditioning (2022) allowing you to stay comfortable year-round with a modern, energy-efficient system,Total Re-piping (2021) ensures smooth water flow and reduces future maintenance needs, Dishwasher (2021) for easy clean up. Stove & Refrigerator (2022) updated appliances for a sleek, functional kitchen, ready for your culinary adventures, Extra Kitchen Cabinets (2022) for extra space for all your kitchen storage needs, Luxury Vinyl in Bedrooms 2 & 3 provide a stylish, durable flooring that’s easy to maintain, Interior Paint (2021) fresh and neutral color walls throughout the home, Water-softener allows you to enjoy softer water for bathing, reduced hard water scale buildup, extended appliance life, and easier cleaning. This home is ideal for efficient daily living. Recent improvements mean less upkeep and more relaxation for you as well as the low HOA fees cover front and right side mowing, maintenance on the fence and shed, and a sparkling community pool — giving you more time to enjoy life! Newer systems and structural elements help lower insurance premiums and provide added security of your home. Close to local parks, Seminole County "A" Rated Schools, main shopping areas, major roadways for easy commuting. and exciting attractions and destinations for all ages. Perfect for every kind of buyer: seasonal residents can enjoy locking up and leaving, not having to worry about maintenance, collegiate students, checks all the boxes for first time home-buyers, empty-nesters downsizing, or anyone looking for comfortable carefree living.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-585-0500)
Listing Agent: Linda Bain (407-474-5269)
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
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)
1320 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708
$480,0009 Days on yellowkey MLS ID: A4696204
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2359 Built: 2023Monthly Fee: $235 Tax: $6,235 (2025)Community: Seminole Crossing TownhomesTownhouse
Taxes:$6,235
Remarks: Perfectly positioned in one of Winter Springs' most convenient and desirable locations, this fabulous home offers a sophisticated blend of modern design, flexible living spaces, and low-maintenance comfort. Situated within a beautifully maintained community just steps from Winter Springs Town Center, this three-story residence places shopping, dining, entertainment, and everyday conveniences right at your fingertips. Designed with both functionality and style in mind, the thoughtfully crafted floor plan offers exceptional versatility. The first level features a private bedroom suite, ideal for guests, a home office, multigenerational living, or anyone seeking additional privacy. Upstairs, the main living level serves as the centerpiece of the home, where an open-concept design seamlessly connects the kitchen, dining area, and spacious gathering room. The open floor plan creates an inviting atmosphere perfect for both everyday living and entertaining. The upper level is dedicated to comfort and relaxation, featuring three additional bedrooms, two full bathrooms, and a conveniently located laundry room. The spacious primary suite provides a peaceful retreat, while the secondary bedrooms offer flexibility for family, guests, or workspace needs. Beyond the home itself, residents enjoy access to community amenities including a sparkling pool, walking trails, and beautifully landscaped common areas. Top-rated Seminole County schools, local parks, and major commuter routes are all nearby, providing easy access to downtown Orlando, area employers, and Central Florida's many attractions. Whether you're seeking a primary residence, a lock-and-leave lifestyle, or a home that offers both convenience and comfort, this wonderful home delivers an exceptional opportunity in the heart of Winter Springs.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Sue Silberbusch (407-252-3157)
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)
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