Location: Winter Springs
Keyword(s): Indian Trails Middle
Keyword(s) Middle School: Indian Trails Middle
Do Not Show Listings
877 BENCHWOOD DR, WINTER SPRINGS, FL 32708
$450,00027 Days on yellowkey MLS ID: O6410431
REDUCED by $10,000 (2.2%) on 06/18/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1612 Built: 1983Monthly Fee: $3 Tax: $3,127 (2024)Community: Oak Forest Unit 3Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,127
Elementary School: Keeth Elementary
High School: Winter Springs High
Tax Year: 2024
Middle School: Indian Trails Middle
Remarks: Inviting curb appeal welcomes you into this beautifully maintained Winter Springs pool home tucked within the peaceful established subdivision of Oak Forest. Step inside to an open floor plan with immediate views of the backyard oasis, creating a light and airy feel perfect for everyday living and entertaining. The spacious kitchen opens seamlessly to the living and dining areas and features granite countertops, stainless steel appliances and a breakfast bar ideal for gathering with family and friends. The floor plan offers comfortable living spaces, while sliding doors lead out to the screened porch overlooking the private backyard retreat. Enjoy Florida living year-round with the screened patio, resurfaced pool featuring a PebbleTec finish completed in 2020, a fully fenced yard and plenty of room to relax or entertain outdoors. Major updates provide peace of mind, including the roof, AC, and water heater all replaced in 2015. Additional improvements include gutters added in 2020, pool pump replaced in 2016, new garage door opener in 2025, and updated microwave, dishwasher, and garbage disposal in 2026. This home sits on a spacious lot in a quiet, established neighborhood. Conveniently located near SR-417, shopping, dining, and top-rated Seminole County schools - walking distance to both the elementary and middle school. This home is also just minutes from Trotwood Park and Central Winds Park which features pickleball courts, sports fields, playgrounds, walking trails, and community events.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Melissa Condrey (407-505-9339)
200 BLUE CREEK DR, WINTER SPRINGS, FL 32708
$625,0007 Days on yellowkey MLS ID: O6416327
0 Days Off yellowkey (back on 6/21/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2344 Built: 1997Monthly Fee: $70 Tax: $3,467 (2025)Community: Chestnut Estates Ph 2Single Family
Taxes:$3,467
Elementary School: Lawton Elementary
High School: Oviedo High
Tax Year: 2025
Remarks: Under contract-accepting backup offers. Virtually Staged. Meticulously maintained and beautifully positioned with peaceful conservation and pond views, this 4-bedroom, 3-bathroom home in Chestnut Estates offers 2,344 square feet of spacious single-story living in the desirable Tuscawilla area. Set on an oversized 0.26-acre lot with no rear or side neighbors, this property combines a versatile floorplan, generous living spaces and inviting indoor-outdoor living. Inside, high ceilings and tons of natural light create a bright, open feel throughout the heart of the home. The layout includes a formal dining room with tray ceiling, a front living/flex room with French doors, a spacious family room and an open kitchen with granite countertops, stainless steel appliances, breakfast bar, pantry, and a sunny breakfast nook overlooking the backyard and conservation. The thoughtfully designed split-bedroom floorplan offers both privacy and flexibility. The tucked away primary suite features direct access to the screened rear porch, a large walk-in closet, dual vanities, a garden tub, and a separate shower. Two secondary bedrooms share a spacious Jack-and-Jill style bathroom with an oversized vanity and abundant storage, while the fourth bedroom is positioned near the third full bathroom, which features a walk-in shower and direct porch access. Outdoor living truly shines with a covered screened porch, custom paver patio and firepit area, mature landscaping, aluminum fencing, and peaceful pond and conservation views. The larger lot and natural backdrop create a peaceful setting for relaxing or entertaining. Pride of ownership is evident throughout, with major improvements including a new roof in 2024, Goodman HVAC system in 2021, updated outdoor living spaces, enhanced landscaping and drainage improvements, and consistent preventative maintenance over the years. Conveniently located near Tuscawilla Country Club, parks, shopping, dining, major roadways, and Seminole County schools, this well-cared-for home offers space, privacy, and an exceptional opportunity to enjoy comfortable living in a beautifully maintained home with a setting that’s becoming increasingly difficult to find. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Amanda Meyer (201-406-2900)
1105 CLINGING VINE PL, WINTER SPRINGS, FL 32708
$500,0004 Days on yellowkey MLS ID: O6416115
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2044 Built: 1993Monthly Fee: $53 Tax: $2,249 (2025)Community: Eagles LandingSingle Family
Taxes:$2,249
Elementary School: Rainbow Elementary
Remarks: Virtually Staged. Eagles Landing is calling and this one has the pool to prove it. Set on a lush quarter-acre lot in one of Winter Springs' most established neighborhoods, this 3-bed, 2-bath stunner checks every box: soaring vaulted ceilings, separate formal living and dining, a kitchen that opens to the family room, and a screened pool with spa just steps from your back door. The primary suite has a walk-in closet, dual vanity, soaking tub, separate shower, and marble finishes that make it feel like a true retreat. Big secondary bedrooms. Full laundry room. Washer and dryer stay. The big stuff is done: brand-new AC (2025), 5-year-old water heater, newer pool pump, solar + propane pool heater (both owned no leases). Swim year-round without the utility sticker shock. Tile flooring throughout the main living areas. Low HOA at just $158/quarter. Zoned for Seminole County schools. Minutes to SR 434, the 417, shopping, dining, and everything Central Florida has to offer. Calling all investors and savvy buyers with vision! This home has incredible bones, a layout that buyers love, and a backyard that sells itself. Add your cosmetic touches and watch the value follow. This is the kind of home people drive through a neighborhood hoping to find. Come see it before someone else does.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Heather Pryor (321-303-5393)
1107 WINTER SPRINGS BLVD, WINTER SPRINGS, FL 32708
$570,0007 Days on yellowkey MLS ID: O6417844
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2345 Built: 1973Monthly Fee: $3 Tax: $2,525 (2025)Community: Winter Spgs Unit 4Single Family
Taxes:$2,525
Remarks: Welcome to this beautifully maintained, freshly painted 4-bedroom, 3-bathroom home situated on a picturesque wooded lot in the heart of Tuscawilla, one of Winter Springs' most sought-after communities. Built with quality craftsmanship and designed for comfortable living, this spacious residence features brand-new engineered wood flooring, generously sized bedrooms, multiple living areas, and a layout ideal for both everyday life and entertaining. For added peace of mind, the roof was replaced in August 2021. The expansive backyard provides endless opportunities to enjoy the Florida lifestyle. Whether you dream of creating a garden, playing ball with family and friends, hosting outdoor gatherings, or simply relaxing beneath the shade of mature trees, you'll appreciate the privacy and space this property offers. Located within the highly rated Seminole County School District, this home is also part of Tuscawilla's unique golf cart-friendly community. Enjoy the convenience of taking your golf cart to Tuscawilla Country Club for golf, tennis, dining, and social events. The club is also home to the renowned Tiger Sharks Swim Team, one of the area's most respected youth swim programs and a source of pride for the community. Outdoor enthusiasts will love being just moments from the Cross Seminole Trail, offering miles of scenic pathways for biking, walking, jogging, and enjoying the natural beauty of Central Florida. Conveniently located near SR 417, this home provides easy access to Orlando, area employers, shopping, dining, healthcare, Florida's beautiful beaches, and world-famous attractions. Restaurants, retail centers, and everyday conveniences are all just minutes away. If you're searching for a spacious home on a beautiful wooded lot with top-rated schools, outstanding recreational amenities, and the unmatched lifestyle that Tuscawilla offers, this is an opportunity you won't want to miss.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Laura Leigh Wood (407-310-4908)
995 DYSON DR, WINTER SPRINGS, FL 32708
$750,0005 Days on yellowkey MLS ID: O6418233
0 Days Off yellowkey (back on 6/20/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2855 Built: 1979 Tax: $9,147 (2025)Community: Winter Spgs Unit 3Single Family
Taxes:$9,147
Remarks: Tucked behind dual steel security gates on more than 1.6 wooded acres in sought after Tuscawilla, this one of a kind gated estate offers exceptional privacy just three blocks from the Tuscawilla Country Club and golf course. Surrounded by mature trees and natural beauty, the property feels like a private park while remaining minutes from shopping, parks, top rated Seminole County schools, major highways, dining, golf, swimming, and tennis. This custom-built California contemporary home features 3 bedrooms, 2.5 baths, and a loft. The dramatic great room showcases soaring two story vaulted ceilings, expansive windows with tranquil wooded views, a polished granite fireplace with gas logs, built-in bookcases, and a wine rack. The adjoining dining and entertaining area includes granite countertops, a wet bar, and a built-in wine cabinet. The kitchen is designed for both everyday living and entertaining, offering cherry cabinetry, solid surface countertops with an integrated sink, an oversized breakfast nook, and a large walk-in pantry. An artistic steel staircase leads to the loft, an ideal space for a home office, studio, or flex room with elevated views of the surrounding landscape. The spacious primary suite features a large walk-in closet and a spa-inspired bath finished in slate with a built-in Jacuzzi tub and waterfall feature, a walk-in shower with fixed glass enclosure, bidet, and updated dual vanity. Additional upgrades include a tankless water heater, updated HVAC system, upgraded plumbing, a large interior laundry room, oversized two car garage, and a separate workshop. The Florida friendly landscape requires minimal maintenance, and the expansive grounds provide ample room for a future pool, tennis court, guest house, or additional outdoor amenities. New septic 2025, part of roof replaced 2025. A rare opportunity to own a private estate property in the heart of Tuscawilla with unmatched natural surroundings and modern conveniences close at hand. Zoned PUD!
Listing Agent: Denise Mckinley (407-625-0635)
1160 CITRUS OAKS RUN, WINTER SPRINGS, FL 32708
$825,00037 Days on yellowkey MLS ID: O6408959
0 Days Off yellowkey (back on 6/12/2026)
REDUCED by $25,000 (2.9%) on 06/04/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3118 Built: 2001Monthly Fee: $127 Tax: $8,339 (2025)Community: Citrus OaksSingle Family
Taxes:$8,339
Remarks: Under contract-accepting backup offers. Exceptional luxury living awaits in this beautifully reimagined 5-bedroom, 3.5-bath residence located within an exclusive gated community. Offering over 3,100 square feet of refined living space, this impressive home showcases luxury finishes and thoughtful upgrades throughout, including elegant travertine flooring, rich oil-rubbed plank floors, and a stunning updated kitchen appointed with stainless steel appliances. Designed for both elevated entertaining and everyday comfort, the floorplan of his home is designed to be a “forever home” and serve you through all stages of life. The 5th bedroom/flex space is conveniently located adjacent to the Primary Bathroom, making it the perfect spot for a nursery or a home office. There are 2 bedrooms connected by a “Jack and Jill” bathroom on the opposite side of the residence, and a spacious, secluded guest suite tucked away on the back of the home; providing guests with a quiet space away from the hustle and bustle of daily life. The spacious interior flows seamlessly to a private screen-enclosed pool retreat featuring a resurfaced finish, travertine pavers, and a fully fenced backyard oasis. The luxurious primary and guest baths have been tastefully updated, while major improvements such as a 2019 roof, hurricane impact slider doors, and fresh exterior paint provide peace of mind and timeless appeal. Perfectly positioned near top-rated schools, upscale shopping, dining, and convenient 417 access, this exceptional residence delivers the ideal blend of luxury, comfort, and location.
Listing is courtesy of: JULIAN PROPERTIES, INC. (407-291-4900)
Listing Agent: Bo Julian (407-694-5843)
1385 SAN DIEGO CT, WINTER SPRINGS, FL 32708
$320,00076 Days on yellowkey MLS ID: O6397680
REDUCED by $29,000 (8.3%) on 06/17/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1518 Built: 1983Monthly Fee: $29 Tax: $1,283 (2025)Community: Sunrise Village Unit 1Spa: NoSingle Family
Taxes:$1,283
Remarks: HUGE PRICE REDUCTION! LOWEST PRICED HOME IN SUNRISE VILLAGE! 2/2 UPDATED HOME! PLUS A BONUS ROOM PERFECT FOR OFFICE, NURSERY, PLAYROOM, HOBBY ROOM, FLORIDA ROOM OR JUST ADDITIONAL LIVING SPACE! OPEN FLOOR PLAN! KITCHEN FEATURES TILE FLOORS, EAT IN KITCHEN AND LIGHT WOOD CABINETRY! ROOF 2022, A/C 2023, WATER HEATER 2025! MAIN BATH UPDATED WITH DECORATIVE TILE, GRANITE COUNTER, TILE FLOOR! DOUBLE PANED WINDOWS! WIDE BLINDS! KNOCKDOWN CEILINGS! NO CARPETING THRU OUT! LARGE SCREENED PATIO WITH TILE FLOOR! LOTS OF NATURAL LIGHT! FANS! LAUNDRY IN GARAGE! GREAT LOCATION, HIGHLY RATED SCHOOLS, LOW HOA DUES ($345 YEAR), COMMUNITY BASKETBALL, TENNIS AND PLAYGROUND!. CONVENIENT TO ALL AREAS OF TOWN! PLEASE NOTE: SOLAR PANELS ON ROOF ARE LEASED, AND LEASE IS TRANSFERABLE! APPROX $80 MONTH! SELLER NOTES WITH POWER COMPANY CREDITS, BILL HAS BEEN APPROX. $30 MONTH!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Diane Fuller (407-923-2090)
1208 CHEETAH TRL, WINTER SPRINGS, FL 32708
$669,9005 Days on yellowkey MLS ID: O6416652
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2837 Built: 1979 Tax: $3,887 (2025)Community: Tuscawilla Unit 06Single Family
Taxes:$3,887
Remarks: Under contract-accepting backup offers. Come fall in love with this versatile 5 bedroom 3 bath home on over 1/2 acre beautifully landscaped property with lush trees and gardens....your very own private oasis in the heart of Tuscawilla! With two large master suites, two spacious guest bedrooms plus a fifth bedroom/ home office with exterior door, the opportunities are endless! In addition, most of the home is very tastefully handicapped accessible. Tinker in your oversized 2 car garage, take a stroll to the neighborhood park or the country club, or sit on your covered back porch watching nature dance in your gorgeous and private backyard. Perhaps you could just float in your recently resurfaced screened, solar heated pool with artful brick paver deck and outdoor shower. Rest easy with a newer roof (2025) two new AC systems (2026 and 2024) updated plumbing, complete window replacement and gorgeous new sliding doors. Your parents, guests or special needs family member will enjoy the massive secondary primary suite with tasteful and versatile handicapped accesible bathroom with roll in shower,double sink vanity, and large accessible walk in closet. Tons of storage is found throughout the home including in the oversized laundry room with utility sink, and cabinets galore. Hey, imagine peace and quiet in a potentially chaotic household…. The main primary bedroom is completely separate from all of the others and includes a walk-in closet and a space large enough for all your dressers, nightstands and even a quiet sitting area to enjoy your favorite book. The ensuite Primary bath has Double doors, updated double vessel sinks and other delightful upgrades. As a bonus, you can open your sliding doors in your bedroom to the pool for a moonlight dip! Newer wood ceilings adorn the rear covered porch for daydreaming or making entertaining special. Guests, family and friends will appreciate the additional parking on the expansive driveway (we just know you're going to have a lot of company). Trotwood Park is a fun place to experience the farmer's market and your kiddos can get to school without accessing the major roads!! Tuscawilla isn't just a place to live.....it's a place to call home. This is truly a once in a lifetime opportunity at a very reasonable price. Hurry to see it now before someone else snatches it up!
Listing Agent: Colleen Kahl (407-630-0027)
724 BARRINGTON CIR, WINTER SPRINGS, FL 32708
$399,900397 Days on yellowkey MLS ID: O6312092
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1450 Built: 1987Monthly Fee: $120 Tax: $1,771 (2024)Community: Georgetowne Unit 1Single Family
Taxes:$1,771
Remarks: Very well maintained home in Tuscawilla! Updated kitchen with Granite countertops, Elegant mirrored wall, Ceramic Tile throughout. Double sinks in beautiful master bathroom with garden shower tub! Owners. Replace all new appliance, have access to the neighborhood clubhouse and Community pool, HOA takes care of front yard lawn maintenance. Two parks and a nature, trail are walking distance from the home. Walk to Trotwood Park and to Tuscawilla Country Club for a round of golf or tennis or to just socialize at the café and bar. This is a great opportunity to own an adorable low maintenance single-family home in the most affordable sought-after Country Club community in Seminole county. A rated school district! Short drive to Oviedo Marketplace and restaurants! Seller willing to contribute $2000 towards closing costs!! Don't miss this opportunity!! --
Listing is courtesy of: DIAMOND 2000 REALTY, INC (321-231-4195)
Listing Agent: Ramon Ortiz Cruz (321-231-4195)
1406 BLUMBERG BLVD, WINTER SPRINGS, FL 32708
$420,00037 Days on yellowkey MLS ID: O6408695
REDUCED by $5,000 (1.2%) on 06/19/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1476 Built: 2024Monthly Fee: $356 Tax: $6,076 (2025)Community: Hickory Grove TwnhmsTownhouse
Taxes:$6,076
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)
270 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$249,900224 Days on yellowkey MLS ID: O6359666
REDUCED by $9,100 (3.5%) on 06/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1089 Built: 1994Monthly Fee: $121 Tax: $327 (2024)Community: Deersong 2Spa: NoSingle Family
Taxes:$327
Remarks: Price Improvement to $259,000 * Quick Closing Available. Welcome to 270 San Gabriel Street in Winter Springs—now offered at an updated price and ready for its next owner. This well-maintained, single-story home features vaulted ceilings and a bright, open layout that creates a comfortable and inviting living space. With neutral finishes and ceramic tile flooring throughout, the home is truly move-in ready. All appliances are included for added convenience. Enjoy morning coffee or unwind in the evening on the oversized screened patio, offering a private outdoor retreat. Additional exterior storage provides practical space for bikes, tools, and seasonal items. Located just minutes from the scenic Cross Seminole Trail, the Deersong community also offers access to a pool and cabana for residents to enjoy. Nearby parks, shopping, dining, and top-rated Seminole County schools add to the home’s appeal. Considering making a move to downsize? First-time homebuyer? investor? or seeking a low-maintenance second home in Central Florida? Schedule your private showing today. With a newly reduced price and quick closing available, this is an excellent opportunity to own a well-cared-for home in a desirable location..
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Alie Gattis (407-760-1488)
1200 ROYAL OAK DR, WINTER SPRINGS, FL 32708
$499,99956 Days on yellowkey MLS ID: O6401888
REDUCED by $10,001 (2.0%) on 05/26/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2378 Built: 1981Monthly Fee: $118 Tax: $4,618 (2025)Community: Fairway Oaks Unit 1Single Family
Taxes:$4,618
Remarks: Welcome to the highly sought after Fairway Oaks at Tuscawilla community, where homes like this rarely come available! This spacious home features 3 bedrooms and 3 full bathrooms, 2,378 square feet of thoughtfully designed living space, and a private pool in the generously sized, fenced-in backyard oasis. As you enter through the private courtyard, discover the details that make this home so special. The luxury vinyl floors throughout the first floor are not only beautiful but designed for durability. The great room features a floor to ceiling wood burning stone fireplace, soaring cathedral ceilings, and stunning oversized windows which fill the home with natural light throughout. Granite countertops, a breakfast bar, ample storage, and ALL NEW black stainless-steel appliances are just some of the reasons you’ll love this kitchen, which flows naturally into the formal dining room. The first bedroom is situated downstairs, and includes its own ensuite full bathroom, perfect for those needing an in-law suite or multigenerational living. Upstairs you’ll find another full bathroom with a shower/tub combo, the second bedroom, and the primary suite. The primary bathroom includes a walk-in shower and separate bathtub, and the bedroom showcases a private balcony with recently updated flooring; the perfect place to relax and unwind while overlooking the 15th hole of the Tuscawilla golf course! At the back of the house an enclosed Florida room adds additional flex space to fit any lifestyle. Enjoy Florida living in the private pool and large fenced-in backyard, with peace of mind knowing that lawncare (front and back) is covered by the very reasonable, low-cost HOA! Additional features include updated electric panel (2024), new vent fans in all 3 bathrooms, and UV lights installed in both AC intakes to improve the air quality throughout the house and increase energy efficiency. Zoned for some of the best schools Central Florida has to offer, just minutes away from the Oviedo Mall, and right around the corner from the Tuscawilla country club which offers a fitness center, tennis courts, a junior Olympic sized swimming pool, and an 18-hole golf course, you really can’t beat this location! Schedule a showing today!
Listing is courtesy of: THE PALMS PROPERTY GROUP (407-476-4202)
Listing Agent: Austin Masi (407-476-4202)
975 DYSON DR, WINTER SPRINGS, FL 32708
$879,0007 Days on yellowkey MLS ID: O6417467
0 Days Off yellowkey (back on 6/19/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2191 Built: 1980 Tax: $6,089 (2025)Community: Winter Spgs Unit 3Single Family
Taxes:$6,089
Remarks: Under contract-accepting backup offers. Nestled on nearly two private acres in coveted Old Tuskawilla, this one-of-a-kind custom estate offers a rare opportunity to enjoy space, privacy, and timeless character in one of Seminole County's most sought-after communities. Surrounded by majestic oak trees, the property feels like a private retreat while remaining just minutes from top-rated schools, parks, golf, dining, and shopping. A private driveway leads to the home's side-entry two-car garage and picturesque setting. Inside, 2,191 square feet of living space blends warmth and functionality. Solid cherry hardwood flooring flows throughout the main level, where you'll find the formal dining room, a spacious family room, two fireplaces, a breakfast nook, and a generously sized primary suite conveniently located on the first floor. Also on the main level is a flexible office space that could easily serve as a fourth bedroom with minimal modifications, offering added versatility for growing families or guests. Upstairs, two bedrooms feature large closets and share a renovated Jack-and-Jill bathroom. The second floor has been updated with luxury vinyl plank flooring. The screened porch provides the perfect place to enjoy morning coffee while overlooking the expansive backyard, offering endless possibilities for a custom pool, guest house, workshop, or simply enjoying the natural beauty of the property. Nature lovers will appreciate the trail located directly behind the property, providing access for walking, jogging, and exploring the outdoors. Major updates provide peace of mind, including a whole-house repipe (2022), a 10' x 12' storage shed added in 2025, a new roof (2026), and fresh exterior paint (2026). While the kitchen and primary suite present opportunities for cosmetic updates and personalization, the home's solid construction, exceptional lot, and desirable location create an incredible foundation for your vision. Properties with this much land, character, and potential rarely become available in Tuskawilla. Whether you're seeking room to spread out, a private estate setting, or the chance to create your forever home, this exceptional property offers a truly unique opportunity.
Listing is courtesy of: VAN DEN BERG REAL ESTATE GROUP (407-739-9970)
Listing Agent: Caroline Van Den Berg (407-739-9970)
600 NORTHERN WAY #302, WINTER SPRINGS, FL 32708
$269,90077 Days on yellowkey MLS ID: O6396912
1 Days Off yellowkey (back on 6/19/2026)
REDUCED by $5,100 (1.9%) on 06/03/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1425 Built: 1981 Tax: $4,268 (2025)Community: Tuscany Place Ph 1Condo
Taxes:$4,268
Remarks: Under contract-accepting backup offers. Virtually Staged. Seller may consider buyer concessions if made in an offer ~ Welcome to Tuscany Place, a GATED COMMUNITY in the heart of Tuskawilla – one of Winter Springs’ most desirable and established areas! This UPDATED second-floor condo delivers the perfect blend of modern style, LOW MAINTENANCE LIVING, and an unbeatable Central Florida location. Major updates are already done for you, including the kitchen and both bathrooms, plus a NEWER A/C (2020), giving peace of mind from day one. Inside, the home has been tastefully updated with modern finishes and fixtures, creating a clean, MOVE-IN READY space that feels both fresh and inviting. WOOD LAMINATE FLOORING flows throughout the entire unit, enhancing the seamless, low-maintenance lifestyle. The OPEN CONCEPT living and dining area is filled with NATURAL LIGHT thanks to a wall of SLIDING GLASS DOORS that lead to a SCREENED BALCONY overlooking peaceful green space – perfect for morning coffee or winding down in the evening. The UPDATED KITCHEN stands out with a fresh, modern color palette and a pop of personality, featuring sleek countertops, STAINLESS STEEL APPLIANCES, ample cabinet storage, a breakfast bar, and a window that brings in even more natural light. The SPLIT BEDROOM layout offers both comfort and privacy with the primary suite tucked away at the back of the home, complete with a WALK-IN CLOSET, updated en-suite bath, and its own private access to a SECOND BALCONY. Two additional bedrooms are positioned at the front of the unit and share a beautifully updated full bath, ideal for guests, family, or a home office setup. Tuscany Place residents enjoy a gated entrance along with added conveniences like lawn care and pest control, making this a truly low-maintenance option. The location is hard to beat – just minutes from Tuskawilla Road, SR 434, and 417, with easy access to TROTWOOD PARK, Central Winds Park, Tuscawilla Country Club, and all the shopping and dining options in Winter Springs and nearby Oviedo. Whether you are looking for your next home or a smart investment, this updated condo is priced to sell and ready for its next owner. Call today to schedule a tour!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
1016 WALNUT CREEK CV, WINTER SPRINGS, FL 32708
$539,9008 Days on yellowkey MLS ID: O6414948
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2375 Built: 2003Monthly Fee: $150 Tax: $3,482 (2025)Community: Parkstone Unit 4Spa: NoSingle Family
Taxes:$3,482
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home nestled on a quiet cul-de-sac in the highly desirable gated community of Parkstone. From the moment you arrive, you'll appreciate the inviting curb appeal, fresh exterior paint, and the pride of ownership throughout. Step inside to discover a light and bright interior filled with airy, spacious living areas designed for both everyday comfort and effortless entertaining. Gorgeous luxury vinyl plank flooring flows throughout the main living spaces, while brand-new carpet adds warmth and comfort to the upstairs bedrooms. Entertaining is a breeze in the large dining room with easy access to the kitchen and family room. The heart of the home opens seamlessly to your private backyard retreat, featuring a sparkling saltwater pool, new sod, and a fully fenced yard that offers both privacy and space to relax, play, or entertain. Whether enjoying a morning coffee poolside or hosting weekend gatherings, this outdoor space is sure to impress. Soaring ceilings on the first floor add to the spacious feeling throughout. Step into the pristine primary suite located on the first floor as an added bonus! Primary bath with separate soaking tub, glass enclosed shower and dual sink vanity make this an owner's dream. Major updates provide peace of mind, including ROOF 2019, AC 2024, FRESHLY PAINTED INTERIOR 2021, HOT WATER HEATER 2021,transferable TERMITE BOND, NEW CARPETS in all bedrooms, NEWLY PAINTED POOL DECK and Taexx, an inovative built-in "tubes in the wall" pest control system .....what more could you ask for? One of the many perks of living in Parkstone is that the HOA takes care of lawn maintenance, giving you more time to enjoy the community and everything the area has to offer. Located just minutes from the popular Central Winds Park, you'll have easy access to festivals, sporting events, walking trails, and community activities year-round. You'll also love being close to Winter Springs Town Center, where shopping, dining, and everyday conveniences are just around the corner. This welcoming home offers the perfect blend of comfort, convenience, and lifestyle in one of Winter Springs' most sought-after gated communities.
724 LAKESIDE DR, WINTER SPRINGS, FL 32708
$264,90021 Days on yellowkey MLS ID: O6412679
2 Days Off yellowkey (back on 6/17/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1168 Built: 1985Monthly Fee: $95 Tax: $2,675 (2025)Community: WildwoodSingle Family
Taxes:$2,675
Elementary School: Highlands Elementary
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 724 Lakeside Dr, nestled in the highly sought-after Wildwood community. This beautifully maintained 2-bedroom, 2-bathroom home offers 1,168 square feet of comfortable living space and presents an excellent opportunity for first-time homebuyers, downsizers, or anyone seeking a move-in-ready home in one of Winter Springs' most established neighborhoods. As you step inside, you'll immediately notice the fresh updates throughout, including brand-new carpet that adds warmth and comfort to every room. The functional floor plan offers a spacious living and dining area filled with natural light, creating an inviting atmosphere for both everyday living and entertaining guests. The kitchen provides ample cabinet and countertop space with easy access to the main living areas, making meal preparation and gatherings effortless. The primary suite offers a private retreat complete with an en-suite bathroom and generous closet space. A well-sized secondary bedroom and full guest bathroom provide flexibility for family members, guests, or a home office setup. The guest bathroom has been enhanced with a newly installed backsplash, adding a stylish and modern touch. Step outside and enjoy all that the Wildwood community has to offer. Residents have access to a community swimming pool, tennis courts, playground, and a community clubhouse, providing plenty of opportunities for recreation and social gatherings. The neighborhood's mature landscaping, tree-lined streets, and established character create a welcoming environment that homeowners have enjoyed for years. Conveniently located in the heart of Winter Springs, this home is just minutes from the Cross Seminole Trail, Central Winds Park, Winter Springs Town Center, shopping, dining, and top-rated Seminole County schools. Easy access to major roadways makes commuting throughout Central Florida a breeze while still allowing you to enjoy the charm and tranquility of this sought-after community. Whether you're searching for your first home, looking to downsize, or seeking a low-maintenance lifestyle in a prime location, this property offers the perfect combination of comfort, convenience, and community. Schedule your private showing today and discover everything 724 Lakeside Dr has to offer.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Eric Campbell (321-279-8941)
116 PHILADELPHIA WAY, WINTER SPRINGS, FL 32708
$310,000142 Days on yellowkey MLS ID: O6379053
REDUCED by $15,000 (4.6%) on 06/17/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1468 Built: 2005Monthly Fee: $300 Tax: $4,182 (2024)Community: Heritage Park TwnhmsTownhouse
Taxes:$4,182
Remarks: Well-appointed 3-bedroom, 2.5-bath townhome for sale in a gated community, offering a great combination of functionality, privacy, and location. Designed for comfortable living, this home includes energy-efficient double-pane windows that enhance interior comfort and help reduce outside noise. The primary suite features a spacious walk-in closet with natural light, creating a bright and welcoming retreat. The kitchen is fully outfitted with appliances and provides ample workspace and storage. The second-floor laundry area adds everyday convenience with washer and dryer included. Residents enjoy access to community amenities such as a swimming pool and playground, all within a controlled-access neighborhood. Zoned for Layer Elementary, Indian Trails Middle School, and Winter Springs High School. Conveniently located near shopping centers, restaurants, parks, and major roadways, with an easy drive to UCF and Orlando International Airport. A great opportunity for a primary residence or investment property — schedule your private showing today.
Listing is courtesy of: SUNNY 365 REALTY GROUP (407-574-7048)
Listing Agent: Isabel Sirizzotti (407-361-8236)
1421 HAPPY BIRD LN, WINTER SPRINGS, FL 32708
$543,888224 Days on yellowkey MLS ID: O6359884
REDUCED by $19,520 (3.5%) on 06/17/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2502 Built: 2019Monthly Fee: $130 Tax: $4,781 (2024)Community: Tuskawilla Crossings 34'SSingle Family
Taxes:$4,781
Remarks: Welcome home! Fall in love this welcoming two-story home that features 4 bedrooms and 3.5 bathrooms, perfectly positioned across from the Cross Seminole Trail. Start your day with a cup of coffee on the charming covered front porch, where you can take in the refreshing breeze and picturesque views of the 13-mile trail that winds through Seminole County and connects to other scenic trails. Step inside to discover an inviting open floor plan enhanced by beautiful wood-style tile flooring. Prepare your favorite meals in the gourmet kitchen with stainless steel appliances, pantry, modern fixtures, and breakfast bar ideal for casual dining. The open-concept living and dining areas create the perfect setting for effortless entertaining. The primary suite, conveniently located on the first floor, includes a walk-in closet and a private ensuite bathroom with dual sinks and a walk-in shower. Ascend to versatile loft area upstairs offering additional space for work, play, or relaxation. You will also appreciate the secondary primary suite on this level, complete with a walk-in closet, dual sinks, and shower. Additionally, two generously sized bedrooms await your use along with a full bathroom. Outside, unwind on the covered back patio, surrounded by vinyl fencing for added privacy. A rear-facing two-car garage with a paver driveway completes the property. This home is part of the Tuskawilla Crossing community, which includes a dog park, a sparkling community pool for leisurely fun, and a playground. The area is rich in dining and shopping options and provides easy access to the 417. Situated in Seminole County which is well known for its public school system. Don’t miss the chance to make this exceptional home yours—schedule a showing today!
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: Brent Dehoop (407-448-8971)
1254 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708
$485,00099 Days on yellowkey MLS ID: O6390820
REDUCED by $10,000 (2.0%) on 04/30/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2359 Built: 2023Monthly Fee: $236 Tax: $6,591 (2024)Community: Seminole Crossing TwnhmsTownhouse
Taxes:$6,591
Remarks: Live luxuriously in almost New Townhouse! Immaculate 3-story townhouse (built 2023) boasts $20,000 in builder upgrades and offers a modern living experience! Unwind while sipping your morning coffee or taking a break on the front porch overlooking serene conservation. Inside, a flexible space on the first floor can be your home office, den, or 4th bedroom with a full en-suite bathroom (including a tub!). Park with ease in the epoxy-floored garage featuring overhead storage racks and extra space for storage. The open-concept second floor features high ceilings and a perfectly sized dining area convenient for family and friends meal time. Unleash your inner chef in the gourmet kitchen with built-in oven, HUGE expansive pantry, granite countertops, soft-close drawers, upgraded cabinets (42" with crown molding), designer fixtures, and updated lighting fixtures. A convenient half bath completes this level. Relax in the spacious living room with room for a desk or play area. The third floor features a well-sized primary bedroom with a HUGE walk-in closet. Upgrades galore: Level 5 textured carpeting provides durability with a touch of luxury. Home is prewired for whole house security including camera hook up. The upgraded laundry room boasts additional storage cabinets and designer tile flooring. Two more bedrooms and a full bath with tub round out the top floor. Enjoy the Florida lifestyle! Take a dip in the community pool just 20 steps away, explore the nearby town center, or hop on the scenic 23-mile Cross Seminole bike trail directly accessible from your doorstep. Conveniently accessible to the 417 highway, local restaurants, shopping, playgrounds and parks, a splash pad, and more just minutes away!
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Sylvana Minnetto (321-946-9876)
114 STONE GABLE CIR, WINTER SPRINGS, FL 32708
$485,9008 Days on yellowkey MLS ID: O6417280
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1814 Built: 1998Monthly Fee: $50 Tax: $4,263 (2025)Community: Stone GableSingle Family
Taxes:$4,263
Remarks: Welcome to the desirable city of Winter Springs, where 114 Stone Gable Cir sits on a beautiful corner lot with peaceful pond views to the rear and side of the home. Just minutes from shopping, restaurants, theme parks, major roads, and the airport, this move-in ready residence puts convenience right at your fingertips. Inside, 1,814 square feet of bright living space welcomes you with high ceilings and an open floor plan that flows naturally from room to room. Hard flooring runs throughout, keeping upkeep easy while adding a clean, modern look. The kitchen is ready for everything from casual breakfasts to weekend gatherings, featuring sleek granite countertops and stainless steel appliances. This thoughtfully designed home offers three comfortable bedrooms and two full bathrooms. The smart split layout tucks the primary bedroom away on its own side for added privacy, creating a quiet retreat at the end of the day, while two additional bedrooms provide flexible space for family, guests, or a home office. The real showstopper waits out back. Step onto the screened-in porch and enjoy your own private pool, perfect for cooling off under the Florida sun or relaxing as you take in the serene water views. The corner-lot setting adds extra elbow room and a sense of openness rarely found. With its prime location, modern finishes, and resort-style outdoor living, this Winter Springs gem checks every box. Schedule your private showing today and make it yours before it's gone!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Kathy Williams (407-230-7305)
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