Location: Winter Springs
Do Not Show Listings
476 CLUB DR, WINTER SPRINGS, FL 32708
$275,00095 Days on yellowkey MLS ID: O6392856
REDUCED by $10,000 (3.5%) on 04/22/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1460 Built: 1995Monthly Fee: $520 Tax: $1,765 (2025)Community: Cypress ClubTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,765
Elementary School: Highlands Elementary
High School: Winter Springs High
Tax Year: 2025
Middle School: South Seminole Middle
Remarks: Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy the benefits of a new roof 2026, new water heater 2026, 2020 A/C system, a full repipe completed in 2016, and a 2016 whole home water softener. Inside, you’ll find an inviting layout with knockdown ceilings throughout the main level and an open living and dining area tucked toward the rear of the home for added privacy. Updated recessed lighting enhances the space, creating a warm and welcoming atmosphere. Just beyond, a step-down enclosed patio offers a serene retreat overlooking wooded views—perfect for relaxing or entertaining. The flexible floor plan includes a downstairs bedroom with an adjacent full bath, ideal for guests, a home office, or multi-generational living. Upstairs, two generously sized bedrooms feature soaring ceilings and abundant natural light. The primary suite offers ample closet space and tranquil views of the surrounding greenery, along with a spacious en-suite bath complete with a Jacuzzi tub and separate shower—perfect for unwinding after a long day. Cypress Club stands out as the only neighborhood within The Highlands with its own private pool, in addition to access to the community’s extensive amenities. Residents enjoy multiple pools, tennis courts, scenic walking trails, parks, pavilions, BBQ areas, a clubhouse, as well as volleyball and basketball courts—delivering a true Florida lifestyle right outside your door. Don’t miss this opportunity to own a move-in-ready home in one of Winter Springs’ most desirable communities!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Jeff Singletary (407-383-1933)
1320 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708
$475,00016 Days on yellowkey MLS ID: A4696204
REDUCED by $5,000 (1.0%) on 06/26/2026
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
Elementary School: None
High School: None
Middle School: None
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)
725 LAKESIDE DRIVE, WINTER SPRINGS, FL 32708
$255,0001 Day on yellowkey MLS ID: O6419715
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1168 Built: 1984Monthly Fee: $95 Tax: $3,856 (2025)Community: WildwoodTownhouse
Taxes:$3,856
Remarks: Enjoy easy living in this beautifully maintained townhome. Ideally located in the sought-after Wildwood community in Winter Springs. This home features 2 bedrooms and 2 bathrooms, freshly painted interior and new blinds in the living room. Tile floors throughout make cleaning a breeze. Enjoy sitting out on the screened in lanai with your favorite beverage. The spacious primary suite serves as a private retreat, complete with a wall closet, and a walk-in closet, and an en-suitebathroom. The well appointed kitchen offers ample cabinetry and counter space and flows seamlessly into the dining and living areas. Residents enjoy access to a variety of community amenities, including a swimming pool, tennis courts, playground and clubhouse. Conveniently located with easy access to major roadways. This home makes commuting throughout Central Florida simple while allowing you to enjoy a charming lifestyle in a prime location.
Listing is courtesy of: GLOBAL PROPERTIES SALES & MGMT (407-675-6999)
Listing Agent: Irene Hayden, Pa (407-376-4355)
161 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$444,990115 Days on yellowkey MLS ID: O6386458
5 Days Off yellowkey (back on 6/23/2026)
REDUCED by $40,000 (8.2%) 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
Taxes:$1,457
Elementary School: Layer Elementary
Middle School: Indian Trails Middle
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.
Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)
Listing Agent: Amanda Warren (321-662-0779)
497 CLUB DR, WINTER SPRINGS, FL 32708
$218,00042 Days on yellowkey MLS ID: O6408474
REDUCED by $14,800 (6.4%) on 05/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1224 Built: 1987Monthly Fee: $520 Tax: $3,344 (2025)Community: Cypress ClubTownhouse
Taxes:$3,344
Remarks: Beautiful 2/2 townhome in highly desirable Cypress Club community in The Highlands of Winter Springs, located in close proximity to SR 434! Light and neutral colors throughout, freshly painted approximately two years ago! *Vaulted ceiling in the spacious family/great room with a wood burning fireplace! Tile flooring in the living areas and laminate in the bedrooms. Split bedroom floorplan, with one bedroom downstairs. Tub and shower combination in both bathrooms. **Brand New Lennox A/C system* and a washer and dryer included! Screened and Covered porch and an additional outside storage closet for additional storage. Community pool in addition the master community pool! Brand new roofs in the community, HOA covers building insurance and grounds maintenance. Two assigned parking spaces and additional visitor parking. The community offers a fabulous club house, nature walking trails, parks, playground and tennis courts. Located close to shops and restaurants and very close to SR 434, SR 17/92 and SR 417 for easy commuting.
Listing is courtesy of: WATSON REALTY CORP (407-323-3200)
Listing Agent: Edyta Olejnik (407-474-0213)
1406 BLUMBERG BLVD, WINTER SPRINGS, FL 32708
$420,00040 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
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)
1357 MILL STREAM LN, WINTER SPRINGS, FL 32708
$399,90010 Days on yellowkey MLS ID: O6417015
REDUCED by $100 (0.0%) on 06/25/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1606 Built: 2015Monthly Fee: $230 Tax: $4,811 (2025)Community: Jesups LandingTownhouse
Taxes:$4,811
Remarks: Welcome to this beautifully updated 3-bedroom, 2.5-bath end-unit townhome in the desirable Jesups Landing community of Winter Springs! Recent updates include new flooring, new exterior paint and a new roof creating a fresh, modern feel. The thoughtfully designed layout features generous living and dining areas that flow seamlessly into the kitchen, making entertaining easy. Upstairs, you'll find all three bedrooms, the laundry area, and a gorgeous patio, in addition to a spacious primary suite that offers a relaxing retreat with ample closet space and an en-suite bath. One of the home's most attractive features is its unbeatable location adjacent to Central Winds Park, where residents can enjoy pickleball courts, a baseball diamond, basketball court, a fishing pier, nature trail, picnic facilities and pavilion, a soccer field, playground, volleyball cours, NEW PICKLEBALL COURTS AND A GREAT DOG PARK in additiona to year-round community events. Families will also appreciate the proximity to highly rated Seminole County schools, shopping, dining, and major commuter routes. Whether you're a first-time homebuyer, downsizing, or seeking a low-maintenance lifestyle in one of Winter Springs' most desirable locations, this beautifully maintained townhome is a must-see!
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Michelle Richardson (321-299-8490)
498 GREEN SPRING CIR, WINTER SPRINGS, FL 32708
$249,0008 Days on yellowkey MLS ID: O6418425
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1363 Built: 1987Monthly Fee: $190 Tax: $1,639 (2025)Community: Mount Greenwood Unit 4 OfTownhouse
Taxes:$1,639
Elementary School: Winter Springs Elementary
Remarks: Welcome to 498 Green Spring Circle in the desirable Mount Greenwood community of Winter Springs! This beautifully maintained 2 bedroom, 1.5 bath end-unit townhome offers peaceful pond views, low-maintenance living, and access to top-rated Seminole County schools. Step inside to an open and inviting floor plan featuring ceramic tile flooring throughout the main living areas and fresh interior paint. The spacious living and dining areas flow seamlessly to the oversized screened patio with paver flooring, creating the perfect space to relax, entertain, or enjoy your morning coffee while overlooking the tranquil water and mature trees. The kitchen opens to the main living space, creating a bright and functional layout ideal for everyday living. Upstairs, you'll find two generously sized bedrooms with large closets and ample storage. An additional exterior storage closet off the patio provides even more convenience. Residents of Mount Greenwood enjoy a low HOA and outstanding community amenities, including a sparkling pool, tennis courts, playground, and scenic walking and biking trails. Ideally located just off SR 434 and minutes from Winter Springs Town Center, shopping, dining, parks, and major commuter routes. Whether you're a first-time homebuyer, downsizing, or searching for the perfect Florida retreat, this move-in-ready townhome offers comfort, convenience, and beautiful waterfront views. Don't miss this opportunity to enjoy the Florida lifestyle in one of Winter Springs' most desirable locations. Schedule your private showing today!
Listing is courtesy of: SUNDIAL REAL ESTATE LLC (407-601-2200)
Listing Agent: Nicole Van Treese (407-462-9050)
1326 TARFLOWER DR, WINTER SPRINGS, FL 32708
$430,0009 Days on yellowkey MLS ID: O6416617
REDUCED by $5,000 (1.1%) on 06/23/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1678 Built: 2025Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory Grove TwnhmsTownhouse
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)
173 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$439,990115 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
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.
180 CONSTITUTION WAY, WINTER SPRINGS, FL 32708
$294,99937 Days on yellowkey MLS ID: O6408927
REDUCED by $10,000 (3.3%) on 06/22/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1275 Built: 2005Monthly Fee: $300 Tax: $4,266 (2025)Community: Heritage Park TwnhmsTownhouse
Taxes:$4,266
Remarks: It doesn't get more move in ready than this! Welcome to the highly sought-after gated community of Heritage Park Townhomes in Winter Springs within Seminole County! This tastefully remodeled 2-bedroom, 2.5-bathroom townhome is completely move-in ready and filled with stylish custom upgrades throughout. Step inside to find a warm and inviting living space featuring a custom-built wooden mantle over the electric fireplace, creating the perfect focal point for relaxing or entertaining. The dining area showcases a stunning custom 3D accent wall adding a modern designer touch to the home. The kitchen is beautifully upgraded with quartz countertops, stainless steel appliances, and a pantry providing additional storage space. Upstairs you’ll find both bedrooms thoughtfully laid out in a split floor plan for added privacy. The spacious primary suite features a walk-in closet and an ensuite bathroom complete with quartz countertops and a stand-alone shower. The laundry area is located upstairs in its own designated hallway closet for easy access. When you step outside to your back patio, you'll notice the owners added pavers creating the perfect cozy outdoor space for relaxing evenings or late-night movies under the stars. A/c is 2022! Enjoy low-maintenance living with an HOA fee of only $300/month which includes exterior grounds maintenance, gated community access, community pool, and a playground. This unit also offers a 1-car garage, private driveway parking, and additional guest parking spaces designated for visitors. Located near shopping, dining, parks, and major roadways, this beautifully updated townhome is ready for its next owner to call home, bring your offers!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jeavanna Lanza Pa (585-313-3408)
504 GREEN SPRING CIR, WINTER SPRINGS, FL 32708
$250,00023 Days on yellowkey MLS ID: O6413016
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1363 Built: 1987Monthly Fee: $190 Tax: $4,030 (2025)Community: Mount Greenwood Unit 2 OfTownhouse
Taxes:$4,030
Remarks: Welcome to 504 Green Spring Circle, a beautifully maintained 2 bedroom 2.5 bath townhome nestled in the heart of Winter Springs, where comfort, charm, and everyday functionality come together effortlessly. Inside, the UPDATED KITCHEN features modern finishes, GRANITE countertops, ample prep space, and room for a dine-in table. The home has been thoughtfully maintained, offering peace of mind and move-in-ready convenience. Step outside to one of this home’s standout features a SERENE BACKYARD retreat complete with a screened in porch perfect for morning coffee, evening unwinding, or hosting friends and family. Surrounded by mature landscaping and a peaceful setting, this outdoor space offers the privacy and tranquility you've been searching for. Located in an established community with a LOW HOA FEE, residents enjoy affordability without sacrificing location or lifestyle. A community playground, tennis courts and pool to use as you wish. Conveniently situated near shopping, dining, parks, and top-rated Seminole County amenities, this Winter Springs gem is one you won’t want to miss.
Listing Agent: Riki Cantelli (919-757-8551)
335 LANSBROOK LN, WINTER SPRINGS, FL 32708
$335,00043 Days on yellowkey MLS ID: O6407329
REDUCED by $10,000 (2.9%) on 06/22/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1129 Built: 2007Monthly Fee: $300 Tax: $3,595 (2024)Community: Jesups Reserve Twnhms RepTownhouse
Taxes:$3,595
Tax Year: 2024
Remarks: Welcome Home to 335 Lansbrook Lane! This move-in ready 2 Bed/2 Bath townhouse is ready for its new owner. Enjoy the ultimate Florida lifestyle with peaceful water views right from your front porch. Inside, you’ll find a functional and inviting layout featuring a downstairs bedroom and full bath, while upstairs offers the primary suite, kitchen, and spacious living area. Conveniently located in highly sought-after Seminole County, you’ll be just minutes from shopping, dining, entertainment, and everyday conveniences. Recent updates include a (2023) Roof and (2025) Appliances, making this home truly move-in ready. Come see all this home has to offer! Call Today to schedule your private showing!
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Trace Christian, Iii (407-202-8135)
498 CLUB DR, WINTER SPRINGS, FL 32708
$225,000323 Days on yellowkey MLS ID: O6332792
REDUCED by $10,000 (4.3%) on 06/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1224 Built: 1987Monthly Fee: $524 Tax: $2,970 (2024)Community: Cypress ClubTownhouse
Taxes:$2,970
Remarks: Welcome to Cypress Club, a townhome community located in The Highlands within Winter Springs. New shingle roofing installed within the past months. Freshly painted and new luxury vinyl flooring throughout the unit. Two bedrooms/two bath home is two stories offering split bedrooms. The living room/dining room combo provides high lofty ceilings with celestial windows providing natural sunlight to the home. Sliding glass doors open to a screen enclosed patio to the rear of the property that overlooks Winter Springs peaceful conservation area. Open stairwell that leads to the loft where you will find a spacious laundry arrangement set up. The master bedroom and bath are on the second floor. The home has been freshly painted. The Highlands offers many amenities to include tennis/pickle ball courts, basketball and volleyball, park with BBQ areas and a covered pavilion and boasts its Junior Olympic size swimming pool. Playgrounds throughout the community. Cypress Club also provides a community pool.
Listing is courtesy of: PAINE-ANDERSON PROPERTIES, INC (407-695-7898)
Listing Agent: Joyce Gary (407-782-3276)
471 HARBOR WINDS CT, WINTER SPRINGS, FL 32708
$330,000114 Days on yellowkey MLS ID: O6387316
REDUCED by $5,000 (1.5%) on 04/16/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1680 Built: 2008Monthly Fee: $298 Tax: $4,552 (2024)Community: Harbor WindsTownhouse
Taxes:$4,552
Remarks: Welcome to your own slice of Winter Springs paradise at 417 Harbor Winds Court! Tucked away inside a secure gated community, this beautiful home offers the perfect blend of privacy and suburban tranquility. Step inside to a bright, open-concept floor plan designed for seamless everyday living and effortless entertaining. This home is thoughtfully designed with the primary bedroom suite privately located on the main floor, offering a peaceful retreat complete with a spacious layout and ensuite bath. The heart of the home features a light-filled kitchen that flows beautifully into the main living areas, making it ideal for gatherings. Beyond the gates lies a lifestyle that is hard to match. This property places you right in the center of everything that makes Seminole County so desirable like some of the most sought-after, highly-rated Seminole County Schools, providing a premier educational foundation. This townhome is just minutes from local dining, boutique shopping, seasonal community events, and your weekly grocery runs. Enjoy effortless access to one of the area's best parks, featuring pavilions, playgrounds, sports fields, nature trails, and breathtaking waterfront views. Looking for nature Outdoor enthusiasts will love being steps away from miles of paved trails perfect for morning runs, weekend bike rides, and peaceful walks. With easy access to major highways (417) for a smooth commute around the Orlando metro area, this home truly checks every single box for safety, convenience, and lifestyle. Schedule your private tour today!**BUYER INCENTIVE: Closing costs a concern? The seller's preferred lender is offering a 1% Lender Credit toward the buyer's closing costs or rate buy-down!**
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Terrica Francois (407-680-8268)
538 CRIMSON LN, WINTER SPRINGS, FL 32708
$369,90037 Days on yellowkey MLS ID: O6409571
REDUCED by $5,000 (1.3%) on 06/22/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1854 Built: 2007Monthly Fee: $300 Tax: $5,370 (2025)Community: Jesups Reserve Twnhms RepTownhouse
Taxes:$5,370
Elementary School: Keeth Elementary
Remarks: PRICED to Sell! Motivated Seller. Welcome to 538 Crimson Lane, a beautifully designed townhome located in the highly desirable community of Jesup’s Reserve. Meticulously maintained, this 3-bedroom, 3.5-bathroom home with a 2-car garage showcases numerous upgrades and distinctive features throughout. Ideally situated in the heart of Winter Springs, this property offers the perfect blend of comfort, style, and convenience. From the moment you arrive, the manicured landscaping and spacious front porch create inviting curb appeal. Inside, the first floor features a generously sized bedroom complete with a private bathroom and walk-in closet, making it ideal for guests, a home office, or a quiet retreat. The second floor serves as the main living space, offering an open and airy layout filled with natural light from an abundance of windows. The spacious living and dining areas flow seamlessly into the kitchen, which features granite countertops, a center island, closet pantry, breakfast bar, and ample room for entertaining family and friends. The kitchen is further enhanced with beautiful maple cabinetry. On the third floor, you’ll find the private primary suite, designed for relaxation and comfort. The oversized bedroom includes a large walk-in closet, while the ensuite bathroom features a separate shower and a luxurious oversized soaking tub. This home also includes several valuable updates and bonus features, including a new AC unit installed in 2025, a roof replaced in 2023, and fresh interior paint completed in 2026. The HOA provides added peace of mind by covering exterior maintenance, including grounds care, roof maintenance, and exterior painting. Residents of Jesup’s Reserve also enjoy access to a resort-style pool and hot tub. Conveniently located directly across from Winter Springs Town Center, you’ll have easy access to shopping, dining, fitness centers, and entertainment. The area is also known for its top-rated public and private schools, scenic parks, and walking trails, with quick access to major roadways and State Road 417. This exceptional property truly offers everything you need to feel right at home. Schedule your private showing today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Hang Kendall (407-929-8664)
572 PINEBRANCH CIR, WINTER SPRINGS, FL 32708
$330,00074 Days on yellowkey MLS ID: O6397068
REDUCED by $3,000 (0.9%) on 05/12/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1564 Built: 2005Monthly Fee: $264 Tax: $3,808 (2024)Community: Barclay Reserve TwnhmsTownhouse
Taxes:$3,808
Elementary School: Lawton Elementary
High School: Oviedo High
Middle School: Jackson Heights Middle
Remarks: This beautiful 3 bedroom 2.5 bath townhome is located in Winter Springs near 417 plenty of shopping with a premium lot. new roof 2022 updated HVAC system. includes refrigerator, range, and dishwasher, and microwave This gated community has so much to see lots of walking the balcony is private over looking the trees and nature.
Listing Agent: April Angry (407-697-0528)
299 WOODGREEN LN, WINTER SPRINGS, FL 32708
$285,00064 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)
4431 BROOK HOLLOW CIR, WINTER SPRINGS, FL 32708
$220,000163 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
$230,00053 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.
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