Location: Winter Springs
Do Not Show Listings
1165 ORANGE AVE, WINTER SPRINGS, FL 32708
$390,00036 Days on yellowkey MLS ID: O6398101
0 Days Off yellowkey (back on 5/15/2026)
REDUCED by $10,000 (2.5%) on 05/08/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2094 Built: 2015Monthly Fee: $233 Tax: $4,666 (2025)Community: Jesups LandingSpa: NoTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,666
Elementary School: Layer Elementary
High School: Winter Springs High
Tax Year: 2025
Middle School: Indian Trails Middle
Remarks: Under contract-accepting backup offers. Welcome to this stunning, modern end-unit townhome located in the highly sought-after community of Jesup’s Landing in Winter Springs. This beautifully designed 3 bedroom, 3.5 bathroom residence with a spacious 2-car garage offers an exceptional blend of comfort, style, and convenience, making it the perfect choice for buyers seeking luxury townhome living in a prime location. From the moment you arrive, you’ll appreciate the added privacy and natural light that comes with being an end unit, along with the home’s contemporary design and thoughtful layout. The first floor features a full suite that is ideal as a secluded primary bedroom, for guests, multigenerational living, or a home office. This space is complete with elegant granite countertops, a large walk-in shower, and direct access to a private balcony, creating a peaceful retreat. You’ll also find a convenient drop station and easy access to the attached garage, adding functionality to everyday living. As you move to the second level, you’re welcomed into an expansive open-concept living area designed for both entertaining and relaxation. The gourmet kitchen is a true centerpiece, featuring sleek granite countertops, a large center island for gathering, and ample cabinetry for storage. The adjoining dining area flows seamlessly into a spacious living room filled with natural light, while a half bath and two separate private balconies enhance the indoor-outdoor living experience. This level is perfect for hosting guests or enjoying quiet evenings at home. The third floor offers even more versatility with a generous loft area that can serve as a media room, office space, or bonus family room. Two well-appointed bedrooms, each with access to full bathrooms, provide comfort and privacy for family members or guests. Throughout the home, you’ll notice numerous upgrades, meticulous maintenance, and modern finishes that elevate the overall living experience. Residents of Jesup’s Landing enjoy resort-style amenities including a sparkling community pool, a fully equipped fitness center, and a stylish billiards lounge. Outdoor enthusiasts will love the direct access to the Seminole Cross Trail, ideal for biking, jogging, and enjoying Florida’s natural beauty. The home is also centrally situated close to popular restaurants, shopping destinations, entertainment options, and Central Winds Park. Located in top-rated Seminole County school zones and offering convenient access to major highways, this property combines luxury, location, and lifestyle. This move-in ready townhome is a rare opportunity to own a modern, spacious property in one of Winter Springs’ most desirable communities. Don’t miss your chance to experience the best of Florida living in Jesup’s Landing.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Thomas Mcnamara, Jr (407-754-6412)
299 WOODGREEN LN, WINTER SPRINGS, FL 32708
$285,00028 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
Elementary School: None
High School: None
Middle School: None
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)
572 PINEBRANCH CIR, WINTER SPRINGS, FL 32708
$330,00038 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
Tax Year: 2024
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)
506 CLUB DR, WINTER SPRINGS, FL 32708
$232,000183 Days on yellowkey MLS ID: O6362326
REDUCED by $5,000 (2.1%) on 05/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1002 Built: 1987Monthly Fee: $398 Tax: $1,908 (2024)Community: Cypress ClubTownhouse
Taxes:$1,908
Elementary School: Highlands Elementary
Middle School: South Seminole Middle
Remarks: Move-in ready 2-bedroom, 2-bathroom single-level townhome in the heart of Winter Springs! Enjoy an updated kitchen with granite countertops, freshly painted interior, and new flooring. Relax on the screened and tiled lanai overlooking serene greenspace. This quiet, secluded community offers two assigned parking spaces and a community pool just steps from your front door. Residents enjoy amenities including community pool, tennis courts, lush parks, and scenic walking trails throughout the neighborhood. Conveniently located near shopping, dining, entertainment, major highways, and all the area’s conveniences.
Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)
Listing Agent: Kathleen Harrison (407-435-9565)
446 CLUB DR, WINTER SPRINGS, FL 32708
$269,00099 Days on yellowkey MLS ID: O6380694
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1460 Built: 1994Monthly Fee: $520 Tax: $886 (2024)Community: Cypress ClubTownhouse
Taxes:$886
Remarks: Discover effortless living in this immaculate 3-bedroom, 2-bath townhome nestled in the desirable Cypress Club at The Highlands. Thoughtfully maintained and beautifully updated, this residence offers the perfect blend of comfort, style, and convenience with a desirable split-bedroom floor plan—featuring one bedroom and a full bathroom on the main level, and the primary suite along with a third bedroom upstairs. Sliding glass doors open to a private screened porch, ideal for morning coffee, evening relaxation, or entertaining guests. This inviting space offers seamless indoor-outdoor living along with additional storage. The upgraded kitchen is a true highlight, showcasing solid wood cabinetry, modern countertops, and a breakfast bar perfect for casual dining or hosting friends and family. Two reserved parking spaces are conveniently located directly at your front door. Enjoy the resort-style lifestyle The Highlands is known for, offering a community pool, recreational building, tennis courts, and scenic hiking trails. Ideally located near I-4 and SR-417, commuting and weekend adventures are effortless. HOA fees provide exceptional value, covering exterior building and grounds maintenance, community amenities, —delivering peace of mind and truly low-maintenance living. IMPORTANT MESSAGE- While this townhouse HOA fees may seem higher, it covers roof replacement and maintenance (brand new 2026), exterior maintenance, landscaping, and more. A single-family home may have lower HOA fees, but usually comes with higher maintenance costs, more upkeep, and added stress - making the overall expense very similar in the end, with far less hassle in a townhouse community. Schedule your private showing today and make this exceptional townhome yours.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Hanoi Burgos (407-342-1539)
445 GEE HAMMOCK LN, WINTER SPRINGS, FL 32708
$404,00018 Days on yellowkey MLS ID: O6404500
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1682 Built: 2016Monthly Fee: $233 Tax: $3,714 (2025)Community: Jesups LandingTownhouse
Taxes:$3,714
Remarks: Immaculately maintained end-unit townhome, ready for you to make it yours! Bright and airy with plenty of windows, this home offers newly installed luxury vinyl on the stairs and second level, providing a modern, seamless look from top to bottom. The kitchen features stainless steel appliances, quartz countertops, and 42" cabinets, with plenty of counter space and an open floorplan that’s perfect for entertaining. Upstairs, you’ll find 3 bedrooms plus a versatile loft and a private balcony where you can enjoy both sunrises and sunsets over the water. The spacious primary suite includes a tray ceiling and a stylish en-suite bath with a large walk-in shower. The secondary bath offers dual sinks, a convenient feature for busy households. Designer lighting and crown molding throughout the home add an extra touch of elegance. Major systems have been thoughtfully updated, including a brand-new A/C unit installed within the last year and community roofs replaced in 2025 for added peace of mind. No neighbors directly in front—just a calming water view to enjoy from your home. The community pool is just a short walk away, as is the Cross Seminole Trail—perfect for morning and evening walks just steps from your door. The community clubhouse also offers a fitness center and flexible gathering space for working, parties, or events. Follow Orange Avenue for a short walk to Central Winds Park, with sprawling green space, baseball and soccer fields, playgrounds, and year-round community events. You’re also close to top-rated Seminole County schools and Winter Springs Town Center, with easy access to the expressway for commuting. Don’t miss your chance to see this beautiful townhome.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: John Harbuck (407-538-2841)
712 LINDEN DR, WINTER SPRINGS, FL 32708
$310,00074 Days on yellowkey MLS ID: O6388467
REDUCED by $5,000 (1.6%) on 05/09/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1366 Built: 1981Monthly Fee: $95 Tax: $3,298 (2024)Community: WildwoodTownhouse
Taxes:$3,298
Remarks: One or more photo(s) has been virtually staged. Welcome to this well-maintained 3-bedroom, 2-bathroom block townhome offering 1,366 square feet of comfortable living space in the desirable Wildwood community of Winter Springs. Tucked along a quiet tree-lined street. Inside, the home features an open and inviting layout highlighted by vaulted ceilings, neutral tones, and vinyl flooring that create a bright and airy living space filled with natural light. The living and dining areas flow seamlessly into the kitchen, making the home ideal for both everyday living and entertaining. The kitchen is well-appointed with white cabinetry, stainless steel hardware, solid surface countertops, a grey glass tile backsplash, ceramic tile flooring, a spacious pantry, and a full appliance package. Just off the kitchen, the dining area is enhanced with plantation shutters that add character and style. The primary bedroom offers a private retreat with carpeting and large windows that bring in natural light, while the en-suite bathroom features a vanity with a Carrara marble countertop, framed mirror, and a walk-in shower finished with neutral ceramic tile. Step outside to enjoy two private outdoor areas with screened-in lanai, and a patio providing space for relaxing, grilling, or entertaining while overlooking a peaceful treed meadow that offers additional privacy. This home has been carefully maintained and includes important updates such as interior paint completed in 2024, an AC system replaced in 2019, and a roof replaced in 2012. Residents of Wildwood enjoy access to community amenities including a pool, tennis courts, playground, picnic pavilion, volleyball court, and dog park with affordable HOA dues. The home is also located within the highly rated Seminole County school district, including Highlands Elementary, South Seminole Middle, and Winter Springs High School. Conveniently positioned near major roadways, historic downtown Winter Springs, Altamonte Mall, Orlando Sanford International Airport, SunRail, Seminole State College, hospitals, and a wide variety of dining and shopping options, this property offers excellent access to everything Central Florida has to offer. With Orlando’s world-famous theme parks and Florida’s beautiful beaches within about an hour’s drive, this location provides the perfect balance of comfort, convenience, and lifestyle.
Listing is courtesy of: SHAW SIGNATURE RE (407-910-9615)
Listing Agent: Kaleb Shaw (407-910-9615)
1275 MARLEY LN, WINTER SPRINGS, FL 32708
$355,00065 Days on yellowkey MLS ID: O6391943
1 Days Off yellowkey (back on 5/9/2026)
REDUCED by $5,000 (1.4%) on 04/13/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1425 Built: 2015Monthly Fee: $233 Tax: $2,895 (2025)Community: Jesups LandingTownhouse
Taxes:$2,895
Remarks: Welcome to Jesup’s Landing, where style, convenience, and community come together in the heart of Winter Springs—one of Central Florida’s most charming and sought-after towns. This beautifully maintained two-story townhome offers peaceful Seminole Trail views and a lifestyle that feels both relaxed and connected. Inside, the open layout is designed for real life and effortless entertaining. The kitchen steals the show with granite countertops, stunning 42” cabinets with crown molding, an extended double sink, pull-out garbage, and a huge pantry—all flowing seamlessly into the main living space. Upgrades like the Taexx built-in pest control system and keypad garage entry add ease and peace of mind. The best part is this home has a brand new roof! Upstairs, the primary suite feels elevated with a 10-foot vaulted ceiling, spacious walk-in closet, and en-suite bath with dual sinks. Step outside and take in serene Seminole Trail views—perfect for morning walks, bike rides, or unwinding at sunset. Residents enjoy access to a community pool and clubhouse, all just minutes from everything that matters. The location is a standout—close to UCF, Research Park, Lockheed Martin, Siemens, with quick access to the beltway for an easy commute to downtown Orlando, area airports, and beyond. Plus, you’re moments from Central Winds Park, top-rated trails, shopping, dining, and the Winter Springs Town Center. Homes in Jesup’s Landing don’t last—especially ones like this. Come see it before someone else does.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: David Weiss (407-765-9020)
476 CLUB DR, WINTER SPRINGS, FL 32708
$275,00059 Days on yellowkey MLS ID: O6392856
2 Days Off yellowkey (back on 5/8/2026)
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
Taxes:$1,765
Remarks: Under contract-accepting backup offers. 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 2020 A/C system, a full repipe completed in 2016, a 2016 water softener, and an electric water heater approximately 9 years old. Even better, a brand-new roof is currently being installed and is fully covered by the HOA—adding long-term value and convenience. 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)
444 BLUE BAYOU LN, WINTER SPRINGS, FL 32708
$390,00015 Days on yellowkey MLS ID: O6405666
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1854 Built: 2007 Tax: $4,488 (2025)Community: Jesups Reserve Twnhms RepTownhouse
Taxes:$4,488
Remarks: Welcome to 444 Blue Bayou Lane, a fully renovated 3-story end-unit townhome in a prime location in Winter Springs. Renovated within the past 2 years, this home has a modern, light-filled layout with thoughtful updates throughout. The kitchen flows seamlessly into the main living space, opening to a second-floor balcony. Upstairs, the primary bedroom features its own private balcony on the third floor. All bedrooms are well-sized, and the home shows consistent care and quality. The home includes all new appliances, along with a new washer and dryer. A transferable home warranty covers everything inside the home, including appliances and HVAC, for the next 2.5 years, providing added peace of mind. Additional upgrades include a whole-home water filtration system, a valuable feature in this area. A recent appraisal is also available upon request. Conveniently located just minutes from Central Winds Park, Winter Springs Town Center.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
1384 MILL STREAM LN, WINTER SPRINGS, FL 32708
$404,90018 Days on yellowkey MLS ID: TB8504740
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1932 Built: 2015Monthly Fee: $233 Tax: $5,288 (2024)Community: Jesups LandingTownhouse
Taxes:$5,288
Remarks: One or more photo(s) has been virtually staged. Do not miss out on this opportunity for a spacious, tastefully updated, move-in ready townhome in the heart of Winter Springs! This is a low maintenance 3-bed, 3.5 bath end unit with quaint landscaping leading you up the stairs to your classy entry. The interior boasts recent vinyl flooring and no carpet anywhere, perfect for all season in FL. The kitchen and living room are on the main level creating a seamless relaxing or entertaining experience with the ability for residents and guests to have privacy in bedrooms. All modern stainless steel appliances convey! The spacious primary bed/bath is on the 3rd floor and provides a large walk-in closet and dual sinks. Enjoy paradise from your key west style balcony above the 2-car garage. The community amenities include a fitness center and pool overlooking the neighborhood pond. Enjoy quick and easy access to shopping, dining, outdoor activities and entertainment, many of these steps from your front door.
Listing is courtesy of: TAH FLORIDA LLC (844-874-2661)
Listing Agent: Joshua Nogowski (754-234-9626)
1276 CRAB APPLE LN, WINTER SPRINGS, FL 32708
$381,990122 Days on yellowkey MLS ID: O6375116
1 Days Off yellowkey (back on 4/29/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1476 Built: 2025Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Taxes:$1,457
Remarks: As you step inside the Aurora, you are greeted by an inviting open-concept gathering room, seamlessly connecting the dining room and kitchen. The flowing layout creates an expansive and airy atmosphere, perfect for both entertaining guests and enjoying everyday life. The owner's suite is a true retreat, offering a sanctuary of relaxation and tranquility. The spacious bedroom is complemented by a large walk-in closet, providing plenty of storage for your wardrobe and personal items. With two additional bedrooms, this townhome provides flexibility for a growing family, a home office, or a guest room.
Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)
Listing Agent: Amanda Warren (321-662-0779)
607 CASA PARK COURT K, WINTER SPRINGS, FL 32708
$239,90024 Days on yellowkey MLS ID: O6402801
0 Days Off yellowkey (back on 5/5/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1088 Built: 1985Monthly Fee: $207 Tax: $1,556 (2024)Community: Casa Park Villas Ph 2Townhouse
Taxes:$1,556
Elementary School: Keeth Elementary
Remarks: Under contract-accepting backup offers. Welcome home to this beautifully reimagined 2-bedroom, 2-bath townhome in the heart of Winter Springs. From the moment you step inside, you’re greeted by a bright, open-concept layout that seamlessly connects the family room, dining area, and kitchen—creating a warm, inviting space perfect for both everyday living and entertaining. Every detail has been thoughtfully updated, featuring luxury vinyl flooring throughout, fresh modern paint, and a stunning, fully renovated kitchen complete with brand-new cabinetry, sleek countertops, and stainless steel appliances. The result is a clean, contemporary feel that’s as stylish as it is functional. Upstairs, you’ll find a serene primary suite along with a spacious second bedroom, offering comfort and privacy. The bathroom has been completely transformed with elegant marble flooring, adding a touch of luxury to your daily routine. Step outside to your large, screened-in covered patio—an ideal retreat for morning coffee, evening relaxation, or hosting friends in a peaceful outdoor setting. Beyond the beauty, this home offers peace of mind with major upgrades already taken care of, including a brand-new A/C (2026), new Pella double-pane high-impact windows, and a tankless water heater (2026). Located in a desirable community close to parks, scenic trails, dining, shopping, top-rated schools, and major highways, this home truly delivers the perfect blend of comfort, convenience, and value. This isn’t just a townhome—it’s a place where you can settle in, unwind, and feel at home from the very first moment.
Listing is courtesy of: KGV REALTY GROUP (407-474-0844)
Listing Agent: Kristin Vogt Pllc (407-417-7206)
4490 BROOK HOLLOW CIR, WINTER SPRINGS, FL 32708
$245,00017 Days on yellowkey MLS ID: O6405179
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.
Listing Agent: Nicolas Merino (954-226-4314)
326 ROBERTS FAMILY LN, WINTER SPRINGS, FL 32708
$374,90066 Days on yellowkey MLS ID: S5144978
2 Days Off yellowkey (back on 5/5/2026)
REDUCED by $12,000 (3.1%) on 04/16/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1622 Built: 2013Monthly Fee: $300 Tax: $2,266 (2024)Community: Jesups Reserve Twnhms RepTownhouse
Taxes:$2,266
Remarks: Under contract-accepting backup offers. Beautiful three-story townhome offering 3 bedrooms and 3 full bathrooms, thoughtfully designed for comfort, privacy, and flexible living. A unique multi-level layout features one bedroom and full bathroom on each floor, making it ideal for guests, multi-generational living, or working from home. The second-floor bedroom with French doors creates a bright and inviting space, perfect as an office or lounge. The top level showcases a spacious primary suite complemented by a loft area, ideal for a home office or sitting space, along with two walk-in closets providing ample storage. Enjoy open and welcoming living areas, a well-appointed kitchen, and natural light throughout the home. Recent updates include A/C, washer and dryer, and a garage door opener (2025), offering added value and peace of mind. The home also features a modern all-in-one washer and dryer unit for added convenience. Conveniently located near shopping, dining, gyms, and major highways for easy commuting. Move-in ready and a fantastic opportunity to own a well-maintained home with a versatile layout in a desirable location.
Listing is courtesy of: PROPERTY OUTLET INTERNATIONAL (407-723-7000)
Listing Agent: Debbie Clavell (321-274-2024)
167 CONSTITUTION WAY, WINTER SPRINGS, FL 32708
$299,00088 Days on yellowkey MLS ID: O6383981
REDUCED by $9,000 (2.9%) on 04/14/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1275 Built: 2005Monthly Fee: $300 Tax: $2,666 (2025)Community: Heritage Park TwnhmsTownhouse
Taxes:$2,666
Remarks: One or more photo(s) has been virtually staged. ROOF & ELECTRICAL UPDATED (2023) – this well-maintained townhome in the gated Heritage Park community of Winter Springs offers peace of mind along with stylish, LOW MAINTENANCE LIVING in one of Seminole County’s most convenient locations! Thoughtfully designed with TILE & LUXURY VINYL PLANK FLOORING throughout, this home feels light, bright, and MOVE-IN READY from the moment you step inside. The OPEN CONCEPT main floor is ideal for everyday comfort and easy entertaining, featuring a comfortable living area that flows seamlessly into the kitchen. The home chef will appreciate the long breakfast bar for casual dining, STAINLESS STEEL APPLIANCES, rich cabinetry, and generous prep space, while a convenient half bath downstairs adds functionality for guests. Sliding glass doors open to a SCREENED LANAI finished with wood look tile, where mature landscaping and tranquil POND VIEWS create a peaceful outdoor retreat – perfect for morning coffee or unwinding at the end of a long day. Upstairs, both bedrooms offer private en-suite full baths, creating an ideal layout for homeowners, guests, or roommates. The PRIMARY SUITE includes a large WALK-IN CLOSET and relaxing water views, while the overall layout provides comfort and privacy for everyday living. Perfectly positioned across from the COMMUNITY POOL while enjoying serene views out back, this home delivers the best of both worlds. Heritage Park is a GATED COMMUNITY in the heart of Winter Springs, ideally located just off SR-434 and directly across from Central Winds Park, with access to walking trails, lakes, and endless outdoor space to explore. Spend weekends biking the Cross Seminole Trail, boating on Lake Jesup, or checking out the many nearby parks and recreation areas. Residents enjoy access to a community pool, park, and playground, all just minutes from shopping, dining, and major roadways for an easy commute throughout Central Florida. Whether you are searching for your first home, a low-maintenance lifestyle, or a strong rental opportunity, this Constitution Way townhome checks all the boxes with location and lifestyle appeal! Call today to schedule your tour!
585 SHADOW GLENN PL, WINTER SPRINGS, FL 32708
$269,90020 Days on yellowkey MLS ID: O6404267
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1348 Built: 1991Monthly Fee: $493 Tax: $2,550 (2024)Community: Deer Run Unit 19BTownhouse
Taxes:$2,550
Remarks: Welcome home to this move in ready 3 bedroom, 2 bathroom end unit townhome nestled in the heart of Winter Springs! With 1,350 sq ft of well utilized living space, this charming residence offers the perfect blend of comfort and convenience — ideal for first-time buyers looking to plant roots in one of Seminole County's most sought-after communities. As an end unit, enjoy added privacy, extra natural light, and more breathing room than a typical townhome. Step inside to an updated interior that's truly ready for you from day one, no projects, no hassle, just home. Unwind after a long day on your screened patio/lanai, the perfect private retreat for morning coffee or evening relaxation year round. The community offers access to a pool and amenities that make it easy to relax and connect with neighbors. Located in Winter Springs, you're minutes from top-rated Seminole County schools, SR-417, Tuscawilla Country Club, and the vibrant dining and shopping of the Oviedo/Winter Springs area. 3 Beds | 2 Baths | 1,350 Sq Ft | End Unit | Screened Lanai | Community Pool | Move In Ready Don't miss your chance to own in Shadow Glenn — this one won't last! ?? Schedule your private showing today.
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Rodrigo Marsal (407-431-8503)
477 GREEN SPRING CIR, WINTER SPRINGS, FL 32708
$234,99929 Days on yellowkey MLS ID: O6401530
1 Days Off yellowkey (back on 5/2/2026)
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1280 Built: 1989Monthly Fee: $185 Tax: $1,834 (2025)Community: Mount Greenwood Unit 4 OfTownhouse
Taxes:$1,834
Remarks: Under contract-accepting backup offers. Conveniently located in Winter Springs, this property is a Charming end-unit townhome offering extra privacy and a bright, open layout! This well-maintained home features a spacious living area, updated kitchen with modern cabinetry and stainless steel appliances, and a separate dining/flex space perfect for entertaining or working from home. Enjoy durable tile flooring throughout the main living areas, plenty of natural light, and a functional floor plan that feels both comfortable and inviting. The end-unit location provides added yard space and a more private feel. Nearby Attractions: Central Winds Park & Lake Jessup – 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).
Listing Agent: Avel Ramirez (321-304-1690)
439 OLD FARM LN, WINTER SPRINGS, FL 32708
$339,90023 Days on yellowkey MLS ID: O6403125
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1504 Built: 2007Monthly Fee: $300 Tax: $5,063 (2025)Community: Jesups Reserve Twnhms RepTownhouse
Taxes:$5,063
Remarks: One or more photo(s) has been virtually staged. Location, Location, Location! Welcome to this beautifully designed 3-level townhome in the highly sought-after Jesups Reserve community. Featuring 3 spacious bedrooms—each on its own floor—this home offers exceptional comfort, flexibility, and privacy. The top-floor primary suite is a true retreat, complete with a large private balcony, perfect for relaxing and enjoying the outdoors. The second-floor living area serves as the heart of the home, showcasing a well-appointed kitchen, bright dining space, and an inviting living room ideal for both everyday living and entertaining. Each bedroom features its own en-suite bathroom, providing convenience and thoughtful functionality for any lifestyle. Additional highlights include a 2-car rear-entry garage and a centrally located second-floor laundry room, with washer and dryer included. Major updates provide true peace of mind, including a NEW 15 SEER HVAC system (2026), NEW roof installed by the HOA (2022), a fully rebuilt, permitted and inspected balcony (2023), and a permitted hot water heater (2020). Unbeatable location—walk to Publix, restaurants, bars, and a new gym, with quick access to SR-417 just minutes away. Whether you're looking for a primary residence or a strong investment opportunity, this home checks all the boxes. Opportunities like this in Jesups Reserve are rare—schedule your showing today before it's gone! For Sale only.
Listing is courtesy of: ORLANDO REALTY & PROPERTY MGNT (407-641-5782)
Listing Agent: Brian Goodwin (321-652-4335)
502 CLUB DR, WINTER SPRINGS, FL 32708
$219,50063 Days on yellowkey MLS ID: O6390697
REDUCED by $10,000 (4.4%) on 05/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1224 Built: 1987Monthly Fee: $520 Tax: $3,355 (2025)Community: Cypress ClubTownhouse
Taxes:$3,355
Remarks: Beautiful 2 bedroom, 2 bathroom townhome in Winter Springs, located in the sought-after Cypress Club at The Highlands community, known for its lush landscaping, fantastic amenities, and serene walking trails. Step inside to a spacious open floor plan with soaring vaulted ceilings and tile flooring throughout the main living areas. The living room features a cozy wood-burning fireplace, creating a warm and inviting focal point. The galley kitchen is fully equipped with all appliances, a glass tile backsplash, and a closet pantry for added storage. This home offers double suites, thoughtfully split between the two levels, each with its own private bathroom. The upstairs loft provides the perfect flex space for a home office, reading nook, or creative studio. Step out back to a lovely screened patio overlooking a private, park-like setting with no rear neighbors, creating a peaceful outdoor retreat. An exterior storage closet offers convenient space for bikes, tools, or gardening supplies. Recent updates include a full professional re-pipe (2026), new water heater (2025), new refrigerator (2024), new interior paint in modern greige tones (2023), and new carpet in bedrooms and stairs (2023). This townhome includes two reserved parking spaces, side-by-side, including one covered carport space. Cypress Club residents enjoy their own private community pool along with full access to The Highlands’ amenities, including a lap pool, tennis courts, playground, BBQ/picnic areas, and more. Ideally located with easy access to SR-434, 17-92, SR-417, and I-4, and zoned for top-rated Seminole County schools. Outdoor recreation and weekend adventure are just minutes away with convenient access to the Cross Seminole Trail and Central Winds Park, offering miles of scenic biking and walking paths, sports fields, and community events. Everyday conveniences are equally close by, with Winter Springs Town Center and other major shopping plazas just a short drive away, providing easy access to grocery stores, fitness centers, banks, restaurants, and all your daily essentials.
Listing is courtesy of: INFINITY REAL ESTATE GROUP (407-760-0835)
Listing Agent: Tamara Martin (407-760-0835)
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