Location: Winter Springs , 32708
Do Not Show Listings
109 CHERRY CREEK CIR, WINTER SPRINGS, FL 32708
$1,090,00026 Days on yellowkey MLS ID: O6404923
REDUCED by $60,000 (5.2%) on 05/28/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3440 Built: 1996Monthly Fee: $123 Tax: $7,388 (2024)Community: Reserve At Tuscawilla Ph 1 TheSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,388
Elementary School: Keeth Elementary
High School: Winter Springs High
Tax Year: 2024
Middle School: Indian Trails Middle
Remarks: Tucked behind the gates of The Reserve at Tuscawilla, this estate unfolds in a way that feels both grounded and quietly impressive, offering a sense of space, privacy, and ease that is increasingly rare to find. Set on over half an acre, 109 Cherry Creek Circle invites you to settle into a lifestyle where everyday living flows effortlessly into moments worth celebrating. From the moment you arrive, there is a feeling of arrival that stays with you. Mature landscaping, a side-entry three-car garage, and the understated presence of a custom Von Jacobs-built home set the tone. Inside, natural light filters through high ceilings and classic architectural details, guiding you through a layout designed for both connection and retreat. The main living areas feel open yet intimate, centered around a warm gas fireplace and views that draw your attention immediately to what makes this home so special. The backyard is not simply an amenity. It is the heart of the experience. Designed for gathering, the outdoor living space offers multiple destinations to relax, entertain, and unwind. A deep resort-style pool and spa invite long afternoons in the sun, while Tennessee River Rock accents, a dedicated fire pit lounge, and an expansive lanai create layers of texture and ambiance. Evenings here feel effortless, whether hosting friends around the summer kitchen with its Viking grill and Texas smoker or enjoying a quiet night under the stars. It is a setting that naturally becomes part of your daily rhythm. Inside, the kitchen remains connected to it all, with a layout that keeps conversations going from room to room. A gas cooktop, double ovens, and a thoughtfully designed breakfast nook provide a space that is both functional and welcoming. Formal living and dining rooms offer flexibility, whether gathering for holidays or creating a more intimate setting for guests. The primary suite is privately positioned on the first floor, offering a calm and comfortable retreat at the end of the day. Its recently remodeled bath brings a fresh, spa-like feel while honoring the home’s timeless character. Additional bedrooms on the main level are thoughtfully arranged, while an expansive upstairs suite provides flexibility for guests, multigenerational living, or a private office and lounge. There is a sense throughout the home that it has been well cared for and intentionally updated where it matters most. Major improvements including the roof (2017), HVAC (2017), whole-house replumbing (2024), and water heater (2025) allow the next owner to step in with confidence, while leaving room to personalize over time in a way that reflects their own style. Beyond the home itself, life in The Reserve at Tuscawilla offers a lifestyle many seek and few find. Quiet, tree-lined streets, a gated setting, and a strong sense of community create an environment that feels both secure and welcoming. Just moments away, Tuscawilla Country Club becomes an extension of home, with golf, tennis, dining, and social events that bring neighbors together. Nearby trails, top-rated schools, and convenient access to major roadways complete the picture of daily ease. This home represents a rare opportunity to own within one of Winter Springs’ most established and desirable communities. It is a place that feels lived in, loved, and ready for its next chapter, where the value is not only in the features, but in the life it quietly supports.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Kara Lushear (321-663-5550)
240 MOREE LOOP #3, WINTER SPRINGS, FL 32708
$187,00046 Days on yellowkey MLS ID: O6399451
REDUCED by $6,000 (3.1%) on 05/28/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1978Monthly Fee: $425 Tax: $2,103 (2024)Community: Baytree VillageCondo
Taxes:$2,103
Elementary School: Highlands Elementary
Middle School: South Seminole Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to Baytree Village in the heart of Winter Springs—where beautifully landscaped grounds and a welcoming atmosphere create the perfect place to call home. This MOVE-IN READY second-floor condo offers 3 bedrooms, 2 full baths, and added privacy, all in a prime location close to top-rated schools, parks, shopping, dining, and major roadways for an easy commute. Step inside to a bright, open-concept living and dining area featuring a wall of windows and two sets of triple sliding glass doors, filling the space with natural light and providing seamless access to a large screened balcony with peaceful garden views—perfect for relaxing or entertaining. The kitchen is well-equipped with stainless steel appliances, ample cabinet and countertop space, and easy-care tile flooring. The spacious primary suite offers a comfortable retreat, while two additional bedrooms provide flexibility for guests, a home office, or additional living space. Additional highlights include in-unit laundry and extra storage off the balcony. Residents of Baytree Village enjoy well-maintained amenities and close proximity to local parks, including Audubon Park just minutes away. Whether you're a first-time buyer, downsizing, or investing, this is an opportunity you won’t want to miss. Schedule your private showing today!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Christine Landrau (407-949-1421)
417 CRUZ BAY CIR, WINTER SPRINGS, FL 32708
$435,00013 Days on yellowkey MLS ID: O6408099
2 Days Off yellowkey (back on 5/28/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2176 Built: 2006Monthly Fee: $245 Tax: $3,673 (2024)Community: The Landings At ParkstoneTownhouse
Taxes:$3,673
Elementary School: Layer Elementary
Remarks: If you are looking for a turnkey property, this home is it! A rare find end unit has been completely updated & meticulously maintained inside this secluded gated community of The Landings at Parkstone. Imagine yourself in this absolutely stunning home featuring a gourmet kitchen with a clean modern look remodeled in 2025 with premuim quartz countertops, backsplash, new custom cabinetry and new appliances that will please the chef in the family. The primary bathroom was updated in 2024 and features a modern soaking tub, a spacious shower, dual vanity with quartz countertops & new plumbing fixtures. All new flooring throughout with plank tile downstairs and luxury vinyl plank upstairs. Some additional updates include: new AC 2024, roof in 2023, exterior paint in 2023, interior paint in 2025, screened in porch & more. This floor plan offers maximum flexibility with one bedroom & full bath downstairs. The Primary bedroom located upstairs has a custom tray ceiling & an incredibly spacious walk in closet with a small window for natural light. The upstairs has a guest bedroom along with a full bathroom. This neighborhood offers a dedicated community pool for The Landings residents only, secured mailboxes & lawncare included in the quarterly dues. Convenient to the Winter Springs Town Center, Cross Seminole Trail, Dog Park, Central Winds Park & easy eaccess to 417 to shorten the commute. Highly rated Seminole Conty Schools. Bring your most discriminating Buyers as this one will not disappoint!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Ron Verzaro, Ii (407-221-5464)
820 WAKULLA LN, WINTER SPRINGS, FL 32708
$419,90024 Days on yellowkey MLS ID: TB8504175
REDUCED by $5,000 (1.2%) on 05/28/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1658 Built: 2012Monthly Fee: $167 Tax: $5,649 (2025)Community: Winter Spgs Village Ph 1Single Family
Taxes:$5,649
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Move-in ready and thoughtfully updated, this 3-bedroom, 2-bath home offers bright, comfortable living with fresh interior paint, new carpet, and new light fixtures throughout. The open main living area flows easily into the kitchen, where new quartz countertops, a new range, microwave, and dishwasher add style and everyday functionality. A new roof provides valuable peace of mind, while the spacious bedrooms, inviting natural light, and practical layout create a home that feels both polished and livable. With tasteful updates already complete, this home is ready to welcome its next owner.
Listing is courtesy of: OFFERPAD BROKERAGE FL, LLC (813-534-6326)
Listing Agent: Rob Jones (844-448-0749)
439 OLD FARM LN, WINTER SPRINGS, FL 32708
$329,90032 Days on yellowkey MLS ID: O6403125
REDUCED by $10,000 (2.9%) on 05/28/2026
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)
444 BLUE BAYOU LN, WINTER SPRINGS, FL 32708
$385,00024 Days on yellowkey MLS ID: O6405666
0 Days Off yellowkey (back on 5/27/2026)
REDUCED by $5,000 (1.3%) on 05/22/2026
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)
907 GLEN ABBEY CIR, WINTER SPRINGS, FL 32708
$420,0004 Days on yellowkey MLS ID: O6411321
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1791 Built: 1997Monthly Fee: $126 Tax: $2,093 (2025)Community: Greenbriar Sub Ph 2Single Family
Taxes:$2,093
Remarks: Welcome home to this beautiful, move-in-ready residence nestled in the highly sought-after Greenbriar at Tuscawilla community! This charming 3-bedroom, 2-bath home offers a highly functional single-story layout with an open floor plan and split-bedroom design, creating both comfortable everyday living and added privacy. The spacious living and dining areas feature vaulted ceilings and abundant natural light, making the home feel bright and inviting. The oversized primary suite offers a relaxing retreat complete with a large walk-in closet and private bath. Enjoy low-maintenance living with a low HOA that includes lawn maintenance, plus access to the community pool. As an added option, Tuscawilla Country Club offers dining, fitness facilities, a junior Olympic pool, tennis courts and leagues, pickleball, golf, and social events. Conveniently located near SR 417, SR 434, and Red Bug Lake Road, you'll have easy access to shopping, dining, and entertainment. Don’t miss your opportunity to own this sweet home in one of Winter Springs’ most desirable communities. Schedule your private showing today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Jennifer Draper (321-439-7204)
448 MACGREGOR RD, WINTER SPRINGS, FL 32708
$350,00053 Days on yellowkey MLS ID: O6397231
REDUCED by $10,000 (2.8%) on 05/27/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1477 Built: 1993Monthly Fee: $6 Tax: $1,141 (2024)Community: Highland Village 2Spa: NoSingle Family
Taxes:$1,141
Remarks: Explore 448 MacGregor Rd, a individual residence with a straightforward design and integrated features. The interior includes a fireplace, and the primary bedroom features a walk in closet; the primary bathroom provides double sinks and a Jacuzzi. The exterior includes a covered patio and a fenced in backyard, providing an enclosed outdoor area. This property contains practical elements for daily living. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
1534 WESCOTT LOOP, WINTER SPRINGS, FL 32708
$735,000113 Days on yellowkey MLS ID: O6380652
REDUCED by $10,000 (1.3%) on 05/25/2026
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3426 Built: 2004Monthly Fee: $100 Tax: $5,527 (2025)Community: Barrington EstatesSpa: YesSingle Family
Taxes:$5,527
Remarks: At ADJUSTED price of $735,000 for this stunning six-bedroom, four-bath home in a gated community, perfectly positioned with a view of a conservation lot without rear neighbors. Winter Springs address, with top-rated Oviedo Schools! Soak up the Florida lifestyle in this stunning backyard retreat with a sparkling pool and spa. Brand new pool heater plus a spacious outdoor kitchen, complete with a dedicated gas grill area, seating space, and brand new refrigerator. It is the ideal place to enjoy warm Florida days and breezy nights. Inside, the home offers a highly desirable layout, with both the primary suite and an additional bedroom on the first floor, perfect for a mother-in-law suite, guests, or a home office. The open living areas feature tile flooring throughout the main level, while the kitchen is finished with granite countertops and ample workspace for everyday living and hosting. Upstairs, you’ll find generously sized secondary bedrooms and baths, providing flexibility for large families, multigenerational living, or vacation use. The peaceful conservation views create a private, serene backdrop both indoors and out. Located in a gated community, this home combines space, privacy, and resort-style amenities in one exceptional property.
Listing is courtesy of: PALMANO GROUP RE BROKERAGE LLC (321-214-1211)
Listing Agent: Denise Pohlmann (407-701-3346)
600 NORTHERN WAY #906, WINTER SPRINGS, FL 32708
$310,000122 Days on yellowkey MLS ID: O6375918
INCREASED by $11,000 (3.7%) on 05/01/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1609 Built: 2016 Tax: $4,259 (2024)Community: Tuscany Place Ph 1Condo
Taxes:$4,259
Remarks: *SELLER SHALL PAY UP TO $10,000.00 TOWARDS BUYER'S CLOSING COSTS AND PRE-PAIDS WITH FULL PRICE OFFER AND FULLY EXECUTED NO LATER THAN MAY 30, 2026* *Turnkey townhouse, exclusivity, gated community, & close proximity to local parks,* in Tuscany Place located in beautiful Winter Springs. The townhouse style is limited to only a few homes in the new phase of this great community. Spacious open-concept kitchen and overall excellent layout—all bedrooms have their own private full bathroom—one of the bedrooms with en-suite full bath is on the ground level so it’s perfect for an office or a mother-in-law suite. This home's natural focal point is the kitchen with granite countertops, and there's an extra-large kitchen island, which provides essential counter space and storage, cabinets and drawers, and room for a breakfast bar. The kitchen leads to the rest of the living and family room combination, which features glass sliding doors to the patio and a staircase to a great split plan layout for the bedrooms upstairs. This home has all the features you’re looking for including a laundry room with large-size appliances, walk-in closets, a huge refrigerator, dedicated trash drawer in the kitchen, blinds and window treatments, and modern fixtures throughout the home. HVAC 2020, water heater 2017, and a new roof as of March 2026. Low monthly fee covers access to the community pool, exterior maintenance and landscaping, sewer, and trash services. Very close to all the shopping and restaurants at Winter Springs Town Center, and Trotwood Park is right at your doorstep. Contact us today to schedule a private tour! Please allow up to 24 hours for a response to any inquiry and request received on a Sunday will be processed on the following business day. Assigned parking space is 906 and additional parking available. Note: Buyer is responsible for all due diligence including but not limited to verifying community information and rules, transfer fees, square footage, room dimensions, taxes, utility data, school assignment, etc.
Listing is courtesy of: JR REALTY GROUP LLC (407-920-4624)
Listing Agent: John Vincent (407-534-9764)
805 LEOPARD TRL, WINTER SPRINGS, FL 32708
$565,00024 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: Under contract-accepting backup offers. 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)
1384 MILL STREAM LN, WINTER SPRINGS, FL 32708
$399,90027 Days on yellowkey MLS ID: TB8504740
REDUCED by $5,000 (1.2%) on 05/27/2026
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)
1513 BLACK BEAR CT, WINTER SPRINGS, FL 32708
$1,479,50087 Days on yellowkey MLS ID: O6385058
1 Days Off yellowkey (back on 5/27/2026)
REDUCED by $69,500 (4.5%) on 04/16/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 6175 Built: 1989Monthly Fee: $142 Tax: $23,523 (2025)Community: Bear Creek EstatesSingle Family
Taxes:$23,523
Remarks: Under contract-accepting backup offers. Welcome to this exceptional home in the exclusive gated community of Bear Creek Estates, set on over an acre of lush wooded greenbelt with beautiful landscaping and a circular driveway that creates outstanding curb appeal. The over 6,000 sq. ft. (includes 1 car garage/hobby room of approx. 280 sq.ft.) home features a new architectural tile roof (less than one year old) and 10-foot ceilings throughout the first floor, creating a bright and spacious feel. Inside, you’ll find elegant formal living and dining spaces, a private home office, and a comfortable family room overlooking the sparkling pool and lanai. The home offers oversized secondary bedrooms with seating areas, plus a large additional bedroom that can serve as an office, art studio or flex space. Entertainment is exceptional with two theater spaces, The main floor home theater is projector-ready, with acoustic panels, granite snack counter, an electronic masking screen and wiring for 7.1 sound. The upstairs primary bedroom is massive in size and the ideal retreat to unwind at end of the day! Complete with its sitting area and outdoor deck with stunning panoramic views of lush nature. The upstairs primary suite in this home also includes a projector drop-down screen and wiring for 5.1 sound. The private backyard retreat features a beautiful pool with LED lighting, waterfall feature, and updated pump and filter (2023), along with panoramic views of lush green space. Additional highlights include a smart audio system controlled by smartphone app, extensive network wiring, pre-wiring for security cameras, well-fed irrigation, and a backyard telescope pier with power and ethernet. In Winter Springs, this home offers peaceful luxury living while being close to shopping, dining and major commuting routes.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Lynda Miller (407-620-2924)
143 HAYES RD, WINTER SPRINGS, FL 32708
$479,00016 Days on yellowkey MLS ID: O6407546
REDUCED by $10,000 (2.0%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1649 Built: 1983 Tax: $1,782 (2024)Community: North Orlando Ranches Sec 02ASingle Family
Taxes:$1,782
Remarks: Welcome to 143 Hayes Rd, Winter Springs a rare opportunity to own a beautifully renovated home in one of the area’s most exclusive and sought-after locations. Situated on a huge corner lot surrounded by mature trees, this property offers privacy, space, and the freedom of no HOA with low property taxes. This home has been recently updated and is truly move-in ready, featuring a 2017 roof, brand-new AC system, fresh interior and exterior paint, new carpet, and a newly finished driveway. Every detail has been thoughtfully refreshed to provide comfort and peace of mind for the next owner. Step outside and imagine yourself enjoying your own private pool while being surrounded by peaceful natural scenery — the perfect setting for relaxing weekends, entertaining guests, or simply enjoying Florida living at its best. Conveniently located near top-rated schools, shopping, dining, and major highways while still offering the tranquility of a private retreat. Homes like this in Winter Springs rarely hit the market!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Karla De La Cruz (407-775-0268)
412 BLUE BAYOU LN, WINTER SPRINGS, FL 32708
$390,00010 Days on yellowkey MLS ID: O6407027
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1854 Built: 2007Monthly Fee: $260 Tax: $4,079 (2025)Community: Jesups Reserve Twnhms RepSpa: YesTownhouse
Taxes:$4,079
Remarks: Welcome to 412 Blue Bayou Lane in the highly desirable Jesups Reserve community, where elevated style, smart design, and an unbeatable Winter Springs location come together without the luxury price tag. This beautifully maintained 3-bedroom, 3-bathroom, three-story townhome offers low-maintenance living just steps from Winter Springs Town Center. The flexible first-floor bedroom with full bath is ideal for guests, a home office, or multi-generational living. The main level features a bright open-concept living and dining area, an oversized kitchen with like-new stainless steel appliances, a generous breakfast bar, and convenient second-floor laundry. The private third-floor owner’s suite offers a large walk-in closet, en-suite bath with soaking tub and separate shower, and peaceful separation from the main living spaces. Enjoy three outdoor living areas, including a welcoming front porch, updated second-floor patio, and private third-floor balcony perfect for relaxing evenings. Major updates include a new roof in 2022, new A/C in 2023, garage door maintenance in 2024, brand-new stair railing, and laminate flooring throughout with no carpet. The oversized 2-car garage with added storage solutions keeps everything organized and functional. Jesups Reserve residents enjoy a resort-style community pool and spa, scenic pond views, and a well-kept neighborhood setting. The location is hard to beat – you’re minutes from Central Winds Park, Trotwood Park, with convenient access to shopping, dining and major likes like SR-417. This move-in-ready home delivers style, location, and value in one exceptional package. Move-in ready, meticulously maintained, and priced to sell—this is the opportunity buyers have been waiting for.
Listing is courtesy of: COLDWELL BANKER REALTY (813-253-2444)
Listing Agent: Gislene Moorman (407-694-2246)
451 HARBOR WINDS CT, WINTER SPRINGS, FL 32708
$357,5005 Days on yellowkey MLS ID: O6406257
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1914 Built: 2008Monthly Fee: $298 Tax: $3,832 (2025)Community: Harbor WindsSpa: NoTownhouse
Taxes:$3,832
Elementary School: Winter Springs Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome to 451 Harbor Winds Court, located in the desirable Winter Springs’ gated community of Harbor Winds! This beautifully maintained and truly move-in ready two-story townhome offers 3 bedrooms, 2.5 bathrooms, and an attached 2-car garage with updates throughout. Major improvements have already been completed for peace of mind, including a new roof, gutters, A/C system, water heater, and stainless steel kitchen appliances—all installed in 2023. Step inside to discover an inviting floor plan featuring an upgraded kitchen with granite countertops, 42" wood cabinetry, stainless steel appliances, a walk-in pantry, breakfast bar, and a charming breakfast nook perfect for casual dining. The kitchen opens seamlessly to the spacious living area, where sliding glass doors lead to the rear lanai—ideal for relaxing or entertaining. Upstairs, the spacious primary suite easily accommodates a king-sized bedroom set and features a large walk-in closet along with a private ensuite bath complete with dual vanities, a soaking tub, and a separate glass-enclosed shower. The additional bedrooms provide plenty of space and flexibility for guests or a home office. Residents of Harbor Winds enjoy access to a resort-style community pool and well maintained neighborhood, all while being conveniently located near shopping, dining, and everyday conveniences. Centrally located with easy access to Orlando’s world-famous attractions, including Walt Disney World and Universal Studios, and less than an hour from the beautiful beaches of New Smyrna and Daytona. Schedule your private showing today, don't miss out!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Jeff Singletary (407-383-1933)
497 CLUB DR, WINTER SPRINGS, FL 32708
$218,00015 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. Newer a/c 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! 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)
560 PLEASANT GROVE DR, WINTER SPRINGS, FL 32708
$425,00034 Days on yellowkey MLS ID: O6401016
REDUCED by $20,000 (4.5%) on 05/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1654 Built: 1996Monthly Fee: $78 Tax: $5,669 (2024)Community: Tusca OaksSingle Family
Taxes:$5,669
Remarks: Welcome to Tuska Oaks—a well-established community in the heart of Winter Springs known for its convenience and neighborhood feel. Tucked away on a quiet cul-de-sac, this 3-bedroom, 2-bath home offers over 1,600 square feet of comfortable living space with a smart, open layout and soaring vaulted ceilings. The kitchen features granite countertops, stainless steel appliances, and ample cabinet space, opening seamlessly into the dining room area—ideal for everyday living and entertaining. Tile flooring runs throughout the home with laminate or LVP in the bedrooms and bathrooms, making maintenance simple and clean. Major updates have already been handled for you, including a roof replaced in 2018, A/C replaced in 2020, newer water heater (2024), and interior and exterior paint completed just 3 years ago. The secondary bathroom has been fully remodeled, adding a fresh, updated touch. Step outside to a screened-in back porch overlooking a fully fenced backyard, offering privacy and space for pets, play, or outdoor gatherings. Residents of Tuska Oaks enjoy a low HOA and access to a community pool , all while being conveniently located near shopping, dining, and top-rated Seminole County schools.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: David Fraser (407-920-9749)
585 SHADOW GLENN PL, WINTER SPRINGS, FL 32708
$264,90029 Days on yellowkey MLS ID: O6404267
REDUCED by $5,000 (1.9%) on 05/26/2026
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)
108 SUNDANCE CT, WINTER SPRINGS, FL 32708
$349,9009 Days on yellowkey MLS ID: O6409784
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1161 Built: 1997Monthly Fee: $140 Tax: $3,505 (2025)Community: The SeasonsSingle Family
Taxes:$3,505
Remarks: Welcome home to this beautifully remodeled gem tucked away on a quiet cul-de-sac in desirable Winter Springs! From the moment you walk in, you’ll fall in love with the bright, open-concept layout designed for easy living and effortless entertaining. With 1,161 sq ft under air, every inch of this home has been thoughtfully updated and filled with charm. The stunning fully remodeled kitchen is the heart of the home, featuring modern finishes, updated cabinetry, and a welcoming flow into the spacious living and dining areas. Both bathrooms have also been completely renovated, creating a fresh, stylish feel throughout. Step through the back doors and discover your own private retreat — a peaceful backyard backing directly to a beautiful conservation area with no rear neighbors, offering the perfect blend of privacy and nature. Imagine morning coffee with serene views or relaxing evenings enjoying the Florida breeze. Even better, the major 4 systems have all been replaced within the last 5 years, giving buyers confidence and peace of mind for years to come. Whether you’re a first-time buyer, downsizing, or simply looking for a turnkey home in an amazing location, this one checks all the boxes. Conveniently located near shopping, dining, parks, and great schools, this is the opportunity you’ve been waiting for. Sold as-is and ready for its next owner to fall in love!
Listing is courtesy of: JEMINI REALTY CORP (407-765-7292)
Listing Agent: Matias Gomez (407-535-0991)
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