Location: Winter Springs
Keyword(s): Winter Springs High
Keyword(s) High School: Winter Springs High
Do Not Show Listings
224 HIGHLANDS GLEN CIR, WINTER SPRINGS, FL 32708
$295,00011 Days on yellowkey MLS ID: O6409042
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1185 Built: 1986Monthly Fee: $63 Tax: $3,265 (2025)Community: Highlands GlenVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,265
Elementary School: Winter Springs Elementary
High School: Winter Springs High
Tax Year: 2025
Middle School: South Seminole Middle
Remarks: Welcome to 224 Highlands Glen Circle, a beautifully updated 3-bedroom, 2-bath villa with 1,185 sq. ft. of comfortable living space. This home features a modern kitchen with new countertops and appliances, along with fresh interior paint and new flooring throughout. Enjoy the ease of a move-in ready home with a 1-car garage. The community offers fantastic amenities, including a pool, tennis courts, playground, and park, perfect for active lifestyles and family fun. Ideally located in Winter Springs, this villa combines style, convenience, and comfort, schedule your showing today!
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Brian Hyser (407-951-2472)
65 S DEVON AVE, WINTER SPRINGS, FL 32708
$314,90019 Days on yellowkey MLS ID: O6404319
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1075 Built: 1960 Tax: $2,218 (2024)Community: North Orlando 2Nd AddSpa: NoSingle Family
Taxes:$2,218
Tax Year: 2024
Middle School: Indian Trails Middle
Remarks: Welcome to 65 S Devon Avenue, a charming 3 bedroom, 2 bath block-construction home in the heart of Winter Springs—perfect for first-time homebuyers or anyone looking for a move-in-ready home in a highly rated school district. This well-maintained property features a large fully fenced yard, ideal for pets, play, and outdoor living. Enjoy Florida evenings on your screened and covered lanai,or take advantage of the concrete patio pad—a great spot for a firepit, grilling area, or weekend entertaining. A two-car driveway provides ample parking and convenience. No HOA Inside, the home offers a functional layout with natural light throughout, comfortable living spaces, and the solid peace of mind that comes with block construction. Located in the sought-after Winter Springs school district, zoned for: • Winter Springs Elementary • Indian Trails Middle School • Winter Springs High School You’ll love the central location—just minutes to shopping, dining, parks, SR-434, the 417 Expressway, and all the everyday conveniences that make Winter Springs one of Central Florida’s most desirable communities. Affordable, well-located, and full of potential—this home is a fantastic opportunity to own in Winter Springs.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Tina Bircher (321-228-4267)
1406 BLUMBERG BLVD, WINTER SPRINGS, FL 32708
$425,00012 Days on yellowkey MLS ID: O6408695
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1476 Built: 2024Monthly Fee: $356 Tax: $6,076 (2025)Community: Hickory Grove TwnhmsTownhouse
Taxes:$6,076
Elementary School: Layer Elementary
Remarks: Welcome to this almost-new townhome in beautiful Winter Springs! Located in the desirable Hickory Grove community, where you will find a maintenance free living, relaxing pool and cabana, playground for the little ones and a dog park for your furry friend, all just a few steps away and NO CDD to pay. The monthly HOA dues also include: landscaping, irrigation, weed control, exterior paint, roof, 1GB of high speed internet and cable premium package. This stunning residence has been tastefully decorated and offers the perfect blend of modern style, comfort, and convenience. Your front door opens up to the serene parks, fountains and walkways just across the street from your favorite stores and restaurants. Enjoy an open-concept layout with plenty of natural light, a modern kitchen with state of the art SS appliances, quartz counters and a beautiful island to entertain your guests. 3 bedrooms, 2.5 bathrooms, and a 2-car garage, and much more. This home is move-in ready and designed for easy living. Upstairs, the generous primary suite offers a private retreat with an en-suite bath and ample closet space. Built with today’s lifestyle in mind, this home also includes the peace of mind of a builder warranty, this is a fantastic opportunity to own a like-new home in one of Central Florida’s most sought-after areas with top-rated schools.
Listing is courtesy of: RALISTO, LLC (407-493-6032)
Listing Agent: Kalex Espinosa (407-493-6032)
1128 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708
$478,50058 Days on yellowkey MLS ID: O6395600
REDUCED by $10,500 (2.1%) on 05/12/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2344 Built: 2021Monthly Fee: $236 Tax: $2,985 (2025)Community: Seminole Crossing TwnhmsTownhouse
Taxes:$2,985
Remarks: One or more photo(s) has been virtually staged. Welcome to an exceptional opportunity in the heart of Winter Springs, where lifestyle, location and luxury converge at 1128 Spotted Sandpiper Loop. Positioned in a thoughtfully planned community, this residence offers the ideal balance of elegance and everyday convenience. From moment you arrive, you are embraced by a neighborhood designed for connection and ease, tree-lined streets, inviting trails and a sense of community that makes this address desirable. Ideally just moments from Winter Springs Town Center, this residence offers an accessible lifestyle. Natural light fills the interiors, creating a warm and welcoming ambiance suited for relaxed living and stylish entertaining. Thoughtfully designed across three levels, the first floor offers a private retreat ideal for guests, complete with its own en suite. The second level unfolds into the heart of the home, featuring an open concept living space with a well-appointed kitchen, dining area and inviting family room. The third floor is dedicated to restful living, showcasing three bedrooms, two full baths and a convenient laundry area. Updates include new carpeting throughout with transferable warranty and fresh interior paint reflecting the home's meticulous maintenance. Beyond your doorstep, accessibility becomes a defining feature of this lifestyle. Enjoy proximity to local shops, dining, parks and top-rated Seminole County schools, all just moments away. With easy access to major roadways, commuting to downtown Orlando, nearby business hubs, or weekend destinations is simple and efficient. Amenities include community pool, trails and accessibility to area favorites.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Jackie Hughes (407-247-0030)
721 GALLOWAY CT, WINTER SPRINGS, FL 32708
$359,90016 Days on yellowkey MLS ID: G5112246
0 Days Off yellowkey (back on 5/18/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1840 Built: 1977Monthly Fee: $35Community: Highlands Sec 4Spa: YesSingle Family
Taxes:$0
Elementary School: Highlands Elementary
Remarks: Under contract-accepting backup offers. Welcome to this charming home with a beautiful Winter Springs address! Nestled on a quiet, tree-lined cul-de-sac in the legendary Highlands community, this updated two-story 3 bedroom, 2.5 bathroom custom home offers the perfect blend of warmth, comfort, privacy, and functionality — all backing up to a stunning natural spring preserve with trails and no rear neighbors! Offering an inviting layout filled with natural light, this home immediately makes you feel at ease the moment you walk through the door. The great room features soaring ceilings and warm wood accents that reflect character and charm rarely found at this price point. The updated kitchen is designed for both everyday living and entertaining, featuring granite countertops, recessed lighting, pantry storage, and newer modern stainless appliances. The kitchen flows seamlessly into the dining area. Sliding glass doors lead you to your private outdoor retreat. Step outside and enjoy true Florida living with a peaceful wooded view, oversized patio space, luxury hot tub spa with massage jets, grill, and patio table with umbrella— all included! Whether you're hosting guests or unwinding after a long day, this backyard setting is virtually impossible to beat. Upstairs, you’ll find three bedrooms, including a spacious Primary Suite with a huge walk-in closet. The Primary bath offers excellent potential, needing just a touch of TLC. Major updates provide peace of mind, including a Roof (2020), Hot Water Heater (2022), Electrical (2015), Kitchen Renovation (2015), first floor Windows replaced (2015), and AC (2017). Located in the amenity-rich Highlands, residents enjoy access to a community pool, clubhouse, tennis courts, playgrounds, scenic walking trails, and beautiful boardwalks — all with low HOA fees. Add in top-rated Seminole County schools and a location near shopping, dining, parks, and major roadways, and you have an incredible opportunity to own in one of Central Florida’s most loved communities. This is the kind of home buyers wait for — updated, private, full of character, and located in one of the best communities in the area. Don’t miss out!
Listing is courtesy of: BEACON REAL ESTATE & ASSOC (352-253-9200)
Listing Agent: Al Spry (407-310-3064)
201 BURGESS DR, WINTER SPRINGS, FL 32708
$650,00037 Days on yellowkey MLS ID: O6401349
REDUCED by $10,000 (1.5%) on 05/15/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 3046 Built: 2003Monthly Fee: $195 Tax: $7,948 (2025)Community: Avery ParkSingle Family
Taxes:$7,948
Elementary School: Keeth Elementary
Remarks: Welcome HOME, to the BEST VALUE in Winter Springs, a 4-bedroom, 2.5-bath colonial-inspired residence in the LOW MAINTENANCE community of Avery Park. EASY LIVING meets modern comfort across more than 3,000 SQUARE FEET of impeccably maintained living space. Perfectly positioned on a CORNER LOT within a GATED enclave, this home offers an exceptional combination of sophistication, warmth, and nostalgic community charm. From the moment you arrive, the GRACIOUS FRONT PORCH, enhanced by FRESH LANDSCAPING (2026) and UPDATED RAILINGS (2025), sets a refined and inviting tone. Step through the DECORATIVE GLASS-PANELED ENTRY into a light-filled interior adorned with PLANTATION SHUTTERS throughout and rich ARCHITECTURAL DETAILING, creating an atmosphere that feels both elevated and welcoming. The formal Living and Dining Rooms offer elegant spaces for hosting, while the home gracefully transitions into a more relaxed yet equally impressive setting. The CHEF-INSPIRED KITCHEN is truly a centerpiece, beautifully updated with RESURFACED CABINETRY with NEW HARDWARE and PULL-OUT SHELVING (2024), glass-front accents, granite countertops, a sleek tile backsplash, stainless steel appliances (NEW REFRIGERATOR in 2025), a center island, breakfast bar, and pantry closet. The SUNLIT BREAKFAST NOOK, framed by sliding doors, invites you to enjoy morning coffee with views of the outdoor living space. The Family Room exudes comfort and style, featuring a TRAY CEILING and corner sliding doors that open to a paver patio within a PANORAMIC SCREENED ENCLOSURE, seamlessly blending indoor and outdoor living. The Primary Suite, thoughtfully located on the main level, is a true retreat, offering GENEROUS PROPORTIONS, a tray ceiling, abundant natural light, and a LUXURIOUS EN SUITE BATH complete with dual vanities, a soaking garden tub, a step-in shower, and a spacious walk-in closet. A well-appointed Laundry Room and stylish half bath complete the first floor. Upstairs, a SPACIOUS LOFT provides a versatile gathering space, perfect for a media room, game room, or additional lounge. Three additional bedrooms and a full bath offer comfort and flexibility for family or guests, with PROFESSIONALLY CLEANED CARPETING enhancing the move-in-ready appeal. This home is further elevated by an impressive list of updates, including NEW LUXURY VINYL PLANK FLOORING throughout the main floor (2025), FRESH INTERIOR PAINT (2025), EXTERIOR PAINT (2023), a NEWER ROOF (2020), UPDATED LIGHTING, and multiple AC SYSTEMS (2016 & 2018). The THREE-CAR GARAGE with built-in storage racks adds both practicality and visual appeal. Residents of Avery Park enjoy a vibrant lifestyle with AMAZING AMENITIES, including a sparkling community pool, playground, basketball court, gazebo, and a scenic pond with fountain, along with FREQUENT COMMUNITY EVENTS that foster a true sense of belonging. Ideally located near CENTRAL WINDS PARK and WINTER SPRINGS TOWN CENTER, this home offers easy access to shopping, dining, recreation, and everyday conveniences. Families will appreciate proximity to TOP-RATED SCHOOLS, while commuters benefit from NEARBY ACCESS to State Road 417, connecting you quickly to surrounding areas including Orlando. With its classic charm, modern updates, spacious layout, and EXCEPTIONAL LOCATION, this Avery Park home provides a lifestyle that is both elegant and welcoming—truly a place to feel at home. Act quickly—this GEM won't last long!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
408 AVONDALE CT, WINTER SPRINGS, FL 32708
$1,250,00045 Days on yellowkey MLS ID: O6398566
0 Days Off yellowkey (back on 5/17/2026)
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3850 Built: 2003Monthly Fee: $167 Tax: $9,316 (2025)Community: Wicklow Greens At TuscawillaSpa: YesSingle Family
Taxes:$9,316
Elementary School: Rainbow Elementary
Remarks: Under contract-accepting backup offers. Welcome to 408 Avondale Court, a custom estate built by Von Jacobs in 2003 & located in the highly desirable, gated Wicklow Greens community in Winter Springs. Set among just 48 custom homes, this stunning residence sits on arguably one of the best lots in Tuscawilla. This .48 acre property is situated in the rear of the neighborhood, on a quiet cul-de-sac where you can enjoy serene views of conservation & Howell Creek in the back. This home features 5 bedrooms, 4.5 bathrooms, and 3,850 square feet of thoughtfully designed living space. From the moment you enter, you’ll appreciate the elegance of wood flooring throughout the first floor, soaring ceilings, and the ideal layout for both everyday living and entertaining. The generously sized kitchen features wood cabinetry, a long center island that offers plenty of countertop space for meal prep, a wet bar, and ample seating space. All 5 bedrooms are conveniently situated on the lower level, with an oversized 650 sq ft loft & 4th full bathroom upstairs. This layout is ideal, offering several options no matter your stage of life. Step outside to your private backyard retreat, which features pavers, a pool and a gas-heated spa, surrounded by peaceful conservation views—the perfect place for relaxing evenings or weekend gatherings.This home has been meticulously maintained by its original owner and updated with major improvements including a new roof (2022), exterior paint (2022), and newer mechanical systems such as A/C units (2015 & 2016) and water heaters (2022 & 2016). A 3-car side-entry garage completes the picture, offering both convenience and curb appeal. Ideally located just minutes from the Tuscawilla Country Club, residents can enjoy convenient access to golf, dining, and social membership opportunities, making this home perfect for those seeking an elevated Central Florida lifestyle. The community is zoned for top-rated schools including Winter Springs High, Indian Trails Middle, and Rainbow Elementary, with additional private school options nearby, such as The Geneva School, Masters Academy, St. Luke’s, Trinity Prep, and Choices in Learning charter school. This is a rare opportunity to own a luxury home in one of Winter Springs’ most coveted gated neighborhoods. So hop onto your golf cart, and zip on by to see this beauty before it's too late!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Jennifer Christ (407-474-7823)
934 TORREY PINE DR, WINTER SPRINGS, FL 32708
$519,000237 Days on yellowkey MLS ID: O6349893
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1678 Built: 2000Monthly Fee: $126 Tax: $2,280 (2024)Community: Greenbriar Sub Ph 2Single Family
Taxes:$2,280
Remarks: One or more photo(s) has been virtually staged. Beautifully remodeled golf course home in the highly desirable Tuscawilla community! This move-in ready residence has been extensively updated with a fresh modern design throughout, including all new flooring, new interior paint, new granite countertops, custom designer backsplash, stainless steel appliances, and an updated interior lighting package. The spacious primary suite features a fully renovated bath with a new granite vanity, updated hardware and lighting, and a completely redesigned custom glass-enclosed walk-in shower. The guest bath has also been tastefully updated with a new vanity. Enjoy peaceful golf course living with scenic surroundings and a spacious screened patio perfect for relaxing or entertaining. The roof has been recently inspected and is reported to be in fantastic condition, providing added peace of mind for the next owner. Conveniently located near top-rated Seminole County schools, parks, shopping, dining, and major roadways, this is an exceptional opportunity to own a beautifully updated home in one of Tuscawilla’s most sought-after golf course communities.
Listing is courtesy of: CENTURY 21 ALTON CLARK (407-636-4637)
Listing Agent: James Clark (407-575-7011)
1165 ORANGE AVE, WINTER SPRINGS, FL 32708
$390,00044 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
Taxes:$4,666
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)
222 W PANAMA RD, WINTER SPRINGS, FL 32708
$310,000115 Days on yellowkey MLS ID: V4947103
1 Days Off yellowkey (back on 5/14/2026)
REDUCED by $10,000 (3.1%) on 04/14/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1044 Built: 1978 Tax: $4,383 (2024)Community: Foxmoor Unit 2Single Family
Taxes:$4,383
Remarks: POOL HOME + NEW ROOF! Welcome to this beautifully upgraded 3-bedroom, 2-bath residence with a 2-car garage, perfectly positioned in one of Winter Springs’ most sought-after, established neighborhoods with NO HOA. This home features a private, fully fenced backyard oasis with a sparkling pool—ideal for entertaining, relaxing, and enjoying Florida living year-round. A brand-new roof will be installed, offering added value and peace of mind. Conveniently located just minutes from top-rated Seminole County schools, scenic parks, premier shopping, dining, and major highways for an easy commute. Rare opportunity to own a move-in-ready pool home in a prime location—schedule your showing today
Listing is courtesy of: CENTURY 21 MCBRIDE REALTY GROUP (386-866-1007)
Listing Agent: Melissa Maldonado (646-943-4002)
859 BENCHWOOD DR, WINTER SPRINGS, FL 32708
$454,90051 Days on yellowkey MLS ID: O6397781
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1632 Built: 1984 Tax: $1,787 (2025)Community: Oak Forest Unit 3Single Family
Taxes:$1,787
Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated 4-bedroom, 2-bath home nestled in one of Winter Springs’ most sought-after neighborhoods! Perfectly positioned next to a quiet dead-end street, this move-in ready property offers both privacy and convenience—ideal for hosting guests with extra parking or enjoying peaceful, low-traffic surroundings. Step inside to discover a thoughtfully upgraded interior featuring brand-new luxury vinyl plank (LVP) flooring installed in 2025 and elegant 5½-inch baseboards throughout. The heart of the home is the STUNNING, FULLY REMODELED KITCHEN (2022), designed for both everyday living and entertaining. It boasts STAINLESS STEEL APPLIANCES, a LARGE QUARTZ ISLAND WITH BUILT-IN CABINETRY, 42-inch maple wood cabinets in a rich cashew finish with cabinet molding, SOFT CLOSE DRAWERS, and abundant horizontal storage with convenient pull-outs. A double oven, eat-in kitchen space, and open flow into the family room make this layout as functional as it is inviting. Both bathrooms were tastefully updated in 2025, featuring custom lighting and soft-close cabinetry, creating a modern feel in both the primary and secondary baths. Major system upgrades provide peace of mind, including a roof replaced in 2016, ANDERSON DOUBLE PANE LOW-E WINDOWS, Andersen French sliding patio door added in 2021, enhancing energy efficiency and natural light throughout the home. Step outside to your expansive 27’ x 10’ covered and screened lanai—perfect for relaxing or entertaining—with no rear neighbors for added privacy. The backyard also includes a storage shed on a durable 4-inch concrete slab, installed in 2018. With its extensive upgrades, prime location, and turnkey condition, this home truly checks every box. Don’t miss your opportunity to own a beautifully maintained property in the heart of Winter Springs!
Listing is courtesy of: VALENCE REALTY GROUP (407-797-5034)
Listing Agent: Chuck Valence (407-797-5034)
114 SUNDANCE CT, WINTER SPRINGS, FL 32708
$305,500197 Days on yellowkey MLS ID: O6359275
REDUCED by $10,000 (3.2%) on 04/23/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1356 Built: 1997Monthly Fee: $120 Tax: $4,059 (2024)Community: Seasons TheSpa: NoSingle Family
Taxes:$4,059
Remarks: One or more photo(s) has been virtually staged. If you’ve been searching for space, location, and opportunity without overpaying, this cul-de-sac home delivers. Tucked away on a quiet cul-de-sac and backing to a peaceful conservation area with no rear neighbors, this 4-bedroom home offers a rare combination of privacy and value in one of Winter Springs’ most desirable locations. Inside, you’ll find a functional split-bedroom layout, vaulted ceilings, and an open living and dining space designed for everyday comfort. The kitchen flows into a bright dining nook and screened patio, creating an ideal setup for indoor-outdoor living. With major updates already completed, including a 2022 roof, and 2026 water heater, buyers can move in with confidence while still having the flexibility to personalize finishes over time. Additional highlights include dedicated driveway parking for two vehicles, low HOA, and access to community amenities such as a pool, tennis courts, and playground. Located within top-rated Seminole County school zones and just minutes from parks, trails, shopping, and major roadways, this home is perfectly suited for buyers looking to maximize space, location, and long-term value. Back on market due to buyer financing — no inspection concerns.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-841-0888)
Listing Agent: Nora Rios (407-274-1174)
1331 AUGUSTA NATIONAL BLVD, WINTER SPRINGS, FL 32708
$450,00079 Days on yellowkey MLS ID: O6389425
2 Days Off yellowkey (back on 5/12/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1657 Built: 1988Monthly Fee: $125 Tax: $4,965 (2025)Community: Country Club Village Unit 3Single Family
Taxes:$4,965
Remarks: Under contract-accepting backup offers. 3 BED + OFFICE | BRAND NEW ROOF | WOODED LOT | TUSCAWILLA GOLF COMMUNITY - Experience modern, low-maintenance living in the heart of Winter Springs. This fully updated residence in Tuscawilla combines high-efficiency upgrades with a flexible, open-concept floor plan. MAJOR UPGRADES & EFFICIENCY: Brand New Tile Barrel Roof (2026), Carrier HVAC (2016), Whole House Re-pipe, and New Energy-Efficient Water Heater (2024). This home also features Dual Pane Energy-Efficient Windows throughout and an oversized 2-car garage with Epoxy Floors, a utility sink, and decked attic storage. INTERIOR HIGHLIGHTS: The bright, open layout features Vaulted Ceilings, Ceramic Tile + Luxury Vinyl Plank (LVP) flooring (no carpet in sight!) and beautiful updates throughout. You will love the remodeled kitchen that is not only beautiful- but functional! Boasting custom cabinetry, granite countertops, and stainless steel appliances; plus slide-out drawers, a water-filter system and breakfast nook. The spacious great room/dining combo provides a perfect blend of comfort and design, while the dedicated Den/Office provides a private workspace separate from the main bedrooms. OUTDOOR & MORE: Enjoy the all-season Enclosed Florida Room with dedicated A/C overlooking a private wooded lot, plus a paver driveway, rear paver patio, and a kitchen water filtration system. LOCATION & LIFESTYLE: Zoned for top-rated Seminole County Schools and located minutes from TCC (Tuscawilla Country Club) (Golf, Tennis, Olympic Pool), Cross Seminole Trail, and local dining. This home offers the perfect blend of location, lifestyle, and smart updates. Bring your golf cart and move right in!
Listing Agent: Allison Day (407-617-2881)
630 FALCON CT, WINTER SPRINGS, FL 32708
$419,00044 Days on yellowkey MLS ID: O6396134
2 Days Off yellowkey (back on 5/13/2026)
REDUCED by $6,000 (1.4%) on 05/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1360 Built: 1986Monthly Fee: $64 Tax: $1,454 (2024)Community: GreenspointeSingle Family
Taxes:$1,454
Remarks: Under contract-accepting backup offers. PRICE IMPROVEMENT! Welcome to 630 Falcon Ct in the Greenspointe section of The Highlands community in Winter Springs. Located just north of Orlando, this beautiful three-bedroom, two-bathroom home is now available. It features an open layout with abundant natural light, a cozy fireplace, and a custom chef’s kitchen designed for entertaining. One of the property's standout features is the screened-in back porch, which provides a peaceful setting to enjoy sunsets and nature within the large, partially fenced-in backyard. For added peace of mind, the home includes a brand-new tile roof and a clean four-point inspection completed in February 2026. As a resident of The Highlands, you will enjoy access to a private clubhouse, pool, pickleball and tennis courts, and a nature trail. For outdoor enthusiasts, there is also a public mountain bike trail located directly behind the clubhouse. The location is ideally situated for a well-connected lifestyle, offering easy access to the 417, I-4, 17-92, and 434, and is just minutes from the Winter Springs Town Center. Don’t Miss This Exceptional Opportunity - Schedule Your Private Showing Today!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Lisa Eichenblatt (407-595-2592)
1327 AUGUSTA NATIONAL BLVD, WINTER SPRINGS, FL 32708
$448,00044 Days on yellowkey MLS ID: O6399111
1 Days Off yellowkey (back on 5/13/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2128 Built: 1994Monthly Fee: $117 Tax: $2,755 (2024)Community: Country Club Village Unit 3Single Family
Taxes:$2,755
Remarks: Under contract-accepting backup offers. Welcome to Country Club Village, one of Tuscawilla’s most sought-after communities. This light and bright 3-bedroom, 2-bath home is one of the largest one-story floor plans in CCV and one of the most popular, with no step downs. It offers a seamless layout, an eat-in kitchen, a separate indoor laundry, and a spacious primary suite with a sitting area. Come check out the spacious primary bedroom and the remodeled primary bath, featuring a soaking tub and a separate shower. Designed for both comfort and entertaining, the home features a generous living space with a fireplace, an inviting open porch, and an easy indoor-outdoor flow. The HOA-maintained lawn allows for low-maintenance living, while the location places you just moments from the private Tuscawilla Country Club & home of the award-winning, Tiger Sharks Swmin Team, Trotwood Park, where you can play pickleball and enjoy the splash pad, Bear Creek Nature Trail, and the Cross Seminole Trail, with convenient access to top-rated Seminole County schools, dining, SR 417, and both beaches and attractions within about an hour.
Listing Agent: Laura Leigh Wood (407-310-4908)
506 CLUB DR, WINTER SPRINGS, FL 32708
$232,000191 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
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
$269,000107 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)
118 PARTRIDGE CIR, WINTER SPRINGS, FL 32708
$560,00024 Days on yellowkey MLS ID: O6405183
0 Days Off yellowkey (back on 5/9/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2456 Built: 1973 Tax: $2,913 (2024)Community: Winter Spgs Unit 4Spa: NoSingle Family
Taxes:$2,913
Remarks: Under contract-accepting backup offers. Traditional Two-Story 4 Bedroom, 2.5 Bath Pool Home in Tuscawilla offering plenty of room to spread out with an oversized backyard and mature landscaping. Nestled along a beautiful tree-lined street, this home is just minutes from the private Tuscawilla Country Club, home of the champion Tiger Sharks swim team, and everything the Tuscawilla community has to offer. Recent upgrades include new windows, a B-hyve smart irrigation system with remote access connected to a well-fed irrigation system, camera/security system, and a 2026 HVAC system featuring separate upstairs and downstairs compressors for enhanced efficiency and comfort control. Brand new interior and exterior electrical panels have also been installed. Inside, you’ll find elegant details including judges paneling in the dining and living rooms, crown molding in the entry hall, dining room, and living room, along with custom upgraded kitchen lighting. Tuscawilla offers an exceptional lifestyle with top-rated Seminole County schools and nearby Trotwood Park featuring pickleball courts, playgrounds, swings, slides, and a splash pad for the kids. Conveniently located approximately 50 minutes from both Central Florida beaches and the theme parks. Inside, you’ll find elegant details including judges paneling in the dining and living rooms, crown molding in the entry hall, dining room, and living room, along with custom upgraded kitchen lighting. Tuscawilla offers an exceptional lifestyle with top-rated Seminole County schools and nearby Trotwood Park featuring pickleball courts, playgrounds, swings, slides, and a splash pad for the kids. Conveniently located approximately 50 minutes from both Central Florida beaches and the theme parks.
1411 BORG LN, WINTER SPRINGS, FL 32708
$399,000119 Days on yellowkey MLS ID: O6378665
REDUCED by $6,000 (1.5%) on 05/09/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1368 Built: 1981Monthly Fee: $90 Tax: $1,871 (2024)Community: Wedgewood Tennis VillasSingle Family
Taxes:$1,871
Remarks: Price Reduced!! Your wait is over! Welcome to your new home! This beautiful 3 bedroom, 2 bath home delivers 1,368 sq. ft. of peaceful living area in a quiet corner lot. Located in the gorgeous Tuskawilla Country Club community, this home features luxury vinyl flooring throughout the house. Entertain effortlessly with a spacious kitchen featuring stainless steel appliances, recessed lighting, and 42” upgraded cabinets. The main floor master bedroom has walk in closet and access to the covered patio. House has been updated with a new roof in 2023, A/C unit in 2018, Water Heater in 2020, luxury vinyl floors and vinyl fencing. Enjoy the Florida outdoors with a covered and screened in porch to entertain and gaze out over the huge fenced in backyard. Winter Springs is an established community know for its A-Rated schools, "Tree lined streets", golf courses, tennis, and with easy access to shopping at Oviedo Marketplace, Trotwood park and the 417. Schedule a showing today and come experience Winter Springs living.
Listing is courtesy of: SOLID OAK REAL ESTATE LLC (321-888-9232)
Listing Agent: Trevor Laug (321-888-9232)
226 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708
$824,90043 Days on yellowkey MLS ID: O6398877
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2902 Built: 1994Monthly Fee: $44 Tax: $4,461 (2024)Community: Chestnut RidgeSpa: NoSingle Family
Taxes:$4,461
Remarks: Showcase two story gem in the heart of Tuscawilla! Come see the abundant high-end upgrades including a professionally designed chefs’ kitchen with all the bells and whistles! This 4 bedroom pool home with private study and upstairs bonus room features a recently renovated screened pool and is located on a quiet tree lined street in a sought after neighborhood. Your tour begins via newly painted leaded glass doors with a giant Palladian window above. You will be welcomed by a grand two story foyer and an artful staircase with hardwood steps and handsome millwork including 10” crown molding. Flanking the foyer, area an elegant dining space and handsome study with newly installed French doors. The recently renovated designer kitchen features custom cabinetry with double upper cabinets reaching all the way to the ceiling! You will love the quartz topped custom dining/ chef’s island, quartz counter tops, glass tile backsplash, large hidden walk-in pantry with cabinet door front, excellent upgraded appliances, and a dedicated prep sink. Two under-cabinet “Uline” beverage refrigerators add a touch of luxury and convenience. French doors in the kitchen dinette lead you to the covered patio and pool area. Because the kitchen is open to the family room, you stay connected to guests and family relaxing in the huge family room that features a soaring two story ceiling, 8’ tall sliding doors to the back patio, a huge glass transom window above and a stunning woodburning fireplace welcoming you to the heart of the home. From here, your eyes are drawn straight out the glass doors to the newly refurbished, sparkling pool, and lush backyard. The primary suite is located on the first floor and is adorned with upgraded wood flooring, plantation shutters and ample room for a dedicated sitting area. Fresh, neutral finishes and a huge travertine shower give a classic elegance to the primary bath and the updated custom closet is absolutely stunning. The second story features three additional bedrooms (two of them are 15x13) and a large loft/bonus room with storage closet (easily converted to a 5th bedroom) Now, enjoy the outside! The spacious covered lanai and renovated screened solar heated pool invite you to morning coffee, evening dinners, or weekend pool parties. The backyard is spacious and welcomes your little ones to play and pets to run freely. With the pool fully resurfaced, retiled, and upgraded with a cool-touch deck and new filter (with warranty), you can enjoy Florida living at its finest. This home is packed with meaningful upgrades: termite bond with Massey, whole-home repipe (2014), newer water heater (2020), two A/C units (2023 & 2014), new garage door opener, fiber internet with AT&T, new office French doors (2020), hardwood floors, unique terrazzo tile, Crown Molding, Closets by Design systems, new landscaping, fresh interior paint, and more. All appliances are included including the washer and dryer. Yes, you can have all of this: A gorgeous move in ready executive pool home in the highly desirable community of Tuscawilla known for its charm and convenience, a lifestyle that’s hard to beat!
Listing Agent: Colleen Kahl (407-630-0027)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.