Location: Winter Springs
Keyword(s): Winter Springs High
Keyword(s) High School: Winter Springs High
Do Not Show Listings
276 SAN GABRIEL ST, WINTER SPRINGS, FL 32708
$285,00063 Days on yellowkey MLS ID: O6399623
REDUCED by $5,000 (1.7%) on 05/20/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1089 Built: 1994Monthly Fee: $127 Tax: $3,719 (2025)Community: Deersong 2Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,719
Elementary School: Layer Elementary
High School: Winter Springs High
Tax Year: 2025
Middle School: Indian Trails Middle
Remarks: Price Improvements. This 3-bedroom, 2-bathroom home in Deersong-2 is a fantastic opportunity for anyone looking for a move-in-ready property in Winter Springs. With its newly updated kitchen, Modern faucet, granite countertops, and indoor laundry. High ceilings at living room, the home feels both modern and spacious. The community offers excellent amenities, including a gated pool and tennis courts, all for a low HOA fee. It is zoned A+ Seminole county public schools, . Its prime location near top-rated Seminole County schools and the popular Torcaso Cove park makes it ideal for daily living. will not last long, Schedule your private showing today!!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Mariam Sherkawy (407-272-4234)
180 CONSTITUTION WAY, WINTER SPRINGS, FL 32708
$304,99929 Days on yellowkey MLS ID: O6408927
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1275 Built: 2005Monthly Fee: $300 Tax: $4,266 (2025)Community: Heritage Park TwnhmsTownhouse
Taxes:$4,266
Remarks: Welcome to the highly sought-after gated community of Heritage Park Townhomes in Winter Springs! This tastefully remodeled 2-bedroom, 2.5-bathroom townhome is completely move-in ready and filled with stylish custom upgrades throughout. Step inside to find a warm and inviting living space featuring a custom-built wooden mantle over the electric fireplace, creating the perfect focal point for relaxing or entertaining. The dining area showcases a stunning custom 3D accent wall adding a modern designer touch to the home. The kitchen is beautifully upgraded with quartz countertops, stainless steel appliances, and a pantry providing additional storage space. Upstairs you’ll find both bedrooms thoughtfully laid out in a split floor plan for added privacy. The spacious primary suite features a walk-in closet and an ensuite bathroom complete with quartz countertops and a stand-alone shower. The laundry area is located upstairs in its own designated hallway closet for easy access. When you step outside to your back patio, you'll notice the owners added pavers creating the perfect cozy outdoor space for relaxing evenings or late-night movies under the stars. A/c is 2022! Enjoy low-maintenance living with an HOA fee of only $300/month which includes exterior grounds maintenance, gated community access, community pool, and a playground. This unit also offers a 1-car garage, private driveway parking, and additional guest parking spaces designated for visitors. Located near shopping, dining, parks, and major roadways, this beautifully updated townhome is ready for its next owner to call home!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jeavanna Lanza Pa (585-313-3408)
1513 GRACEFUL DOE LOOP, WINTER SPRINGS, FL 32708
$679,90035 Days on yellowkey MLS ID: O6408012
1 Days Off yellowkey (back on 5/23/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2995 Built: 2020Monthly Fee: $135 Tax: $6,580 (2025)Community: Tuskawilla Crossings 50'SSingle Family
Taxes:$6,580
Remarks: Under contract-accepting backup offers. From the moment you walk in, this beautifully appointed 2020 built home in Tuskawilla Crossings and backing up to wooded conservation, feels warm, inviting, and effortlessly functional. This expansive two-story residence offers 4 bedrooms, 2.5 bathrooms, a spacious loft, and the open-concept layout today’s buyers are hunting for. The heart of the home is a bright, beautifully connected living space where the family room, dining area, and kitchen flow effortlessly together—perfect for entertaining, holidays, or laid-back nights at home. The kitchen delivers serious style with 42” cabinetry, quartz countertops, slate appliances, and oversized prep space that makes everyday living feel elevated. Upstairs, the primary suite is oversized and calming with a spa-style bath featuring dual sinks, soaking tub, walk-in shower, and a massive walk-in closet, while the upstairs laundry room adds convenience exactly where you need it. This home includes a whole-house Brita Pro water filtration and softener system, transferable Taexx in-wall pest defense system through Home Team Security, Ring doorbell, security system, faux wood blinds, extended tile flooring, and washer & dryer. Outside, enjoy peaceful conservation views and no rear neighbors! The large backyard, covered lanai and recently added pavers create the perfect setup for cookouts, playtime, pets, or future outdoor dreams with the swing set included too. Located in one of Winter Springs’ most sought-after areas with a community pool, playground and quick access to shopping, dining and major roadways—this home checks boxes buyers didn’t even know they had. Homes this clean, this upgraded, and this move-in ready don’t stay quiet for long. Schedule your exclusive showing today!!
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Miranda Earnest (321-624-0287)
702 GLASGOW CT, WINTER SPRINGS, FL 32708
$313,70077 Days on yellowkey MLS ID: O6394959
REDUCED by $4,000 (1.3%) on 05/23/2026
Bed: 4 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1878 Built: 1974Monthly Fee: $450 Tax: $3,285 (2024)Community: Highland Patio Homes Amended PlatSpa: YesCondo
Taxes:$3,285
Elementary School: Highlands Elementary
Tax Year: 2024
Remarks: Welcome to a beautifully updated patio home tucked away on a quiet, tree-lined cul-de-sac in the desirable Pebble Creek community of The Highlands in Winter Springs. Enjoy Villa-style living with a two-story layout. Offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed layout with the primary suite conveniently located on the first floor, this home blends comfort, functionality, and low-maintenance living. From the moment you arrive, you’ll appreciate the private courtyard entry—perfect for morning coffee or relaxing evenings, along with multiple outdoor spaces, including a screened-in porch and two fenced areas ideal for pets or gardening. Inside, the home features warm wood accents, soaring ceilings, and an abundance of natural light throughout. The updated kitchen is equipped with a gas double oven, modern appliances, pantry storage, and flows seamlessly into the main living areas. An interior laundry/utility room adds everyday convenience. Bathrooms have been tastefully renovated with updated vanities, tilework, and glass shower enclosures. Recent upgrades provide peace of mind, including re-piping, updated HVAC system, water heater, garage door, and energy-efficient windows and doors. Additional improvements include updated flooring, custom closet shelving, and enhanced finishes throughout the home. Located within The Highlands, residents enjoy a wide range of amenities, including a community pool, clubhouse, tennis courts, playgrounds, and miles of scenic walking trails and boardwalks. The HOA maintains exterior elements such as the roof, paint, and landscaping, allowing for easy, low-maintenance living
Listing is courtesy of: SHAWFIELD REALTY GROUP (407-963-7749)
Listing Agent: Carrie Sue Shawfield (407-963-7749)
429 SHEOAH BLVD #12, WINTER SPRINGS, FL 32708
$180,000112 Days on yellowkey MLS ID: O6386330
1 Days Off yellowkey (back on 5/22/2026)
REDUCED by $18,900 (9.5%) on 05/15/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1978 Tax: $2,420 (2024)Community: Baytree VillageCondo
Taxes:$2,420
Elementary School: Winter Springs Elementary
Middle School: South Seminole Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bathroom condo offering the perfect blend of style, comfort, and convenience in the heart of Seminole County. Inside, you’ll find quartz countertops throughout, stainless steel appliances, and stylish brick-lay tile flooring that adds character and a modern touch to the main living areas. The thoughtfully designed layout includes an interior laundry room complete with a full-size GE washer and dryer for everyday ease. The living room features double sliding glass doors that flood the space with natural light and open to your private balcony — the perfect spot for morning coffee or winding down in the evening. Enjoy a low-maintenance lifestyle with an HOA that covers exterior maintenance, roof, and common areas. Community amenities include a junior Olympic-sized pool, pickleball and basketball courts, scenic lake views with a covered pavilion, picnic areas with grills, and beautiful nature trails for outdoor enjoyment. Ideally located with easy access to UCF, 417, 17-92, SR 434, the Cross Seminole Trail, shopping, dining, and more — all while being zoned for top-rated Seminole County schools. Whether you're a first-time buyer, investor, or looking to downsize without sacrificing style, this condo checks all the boxes!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Dominick Florio (321-377-4045)
965 PAPAYA LN, WINTER SPRINGS, FL 32708
$729,90034 Days on yellowkey MLS ID: OM724828
0 Days Off yellowkey (back on 5/22/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3514 Built: 1986Monthly Fee: $3 Tax: $3,805 (2025)Community: Oak Forest Unit 5Single Family
Taxes:$3,805
Elementary School: Keeth Elementary
Remarks: Under contract-accepting backup offers. Nestled in the highly sought-after Oak Forest community of Winter Springs, this beautifully maintained and fully remodeled 5-bedroom, 4-bath pool home offers more than 3,500 square feet of versatile living space designed for luxury, comfort, and flexibility. The main residence features a spacious open-concept kitchen, living and dining area, plus a separate family room and dedicated office/gym space. Adding exceptional value and versatility, the property also includes an attached bonus home with a private entrance. The lower level offers a in-law one-bedroom floor plan with an open living, kitchen, and dining area along with its own patio, while the upstairs studio suite includes a kitchenette and full bath — creating incredible opportunities for multi-generational living, guest accommodations or a home office setup. Inside the main home, the updated kitchen showcases solid wood cabinetry, quartz countertops, high-end stainless steel appliances, and abundant natural light throughout. The luxurious primary suite has been thoughtfully remodeled with custom millwork, shiplap accents, built-in storage, recessed lighting, warm wood-grain tile flooring, designer finishes, and direct patio access for a true private retreat. Step outside and experience Florida living at its finest in the screened-in pool area overlooking a fully fenced backyard and peaceful wooded preserve. Designed for entertaining, the outdoor space features a fully equipped outdoor kitchen including concrete countertops, sink, and refrigerator, built-in fireplace, TV, pool, poolside entertaining areas, low-maintenance artificial turf, a gazebo seating area with TV and fans, and an additional storage shed. Additional highlights include a 2-car garage, abundant parking, solar energy panels, wood-grain tile flooring throughout the main living areas, and well-maintained systems. Ideally located near top-rated Seminole County schools, shopping, dining, parks, and major roadways, this exceptional move-in ready property perfectly combines style, functionality, and an unbeatable location.
Listing is courtesy of: REAL ESTATE RESOLUTIONS OF FLO (813-849-8918)
Listing Agent: Josh Mclennan (813-849-8918)
1422 SPALDING RD, WINTER SPRINGS, FL 32708
$425,000386 Days on yellowkey MLS ID: O6313691
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1456 Built: 1983Monthly Fee: $95 Tax: $1,306 (2024)Community: Wedgewood Tennis VillasSpa: NoSingle Family
Taxes:$1,306
Remarks: PRICE REDUCTION!!!Ready to move into! Well maintained and updated 3-bedroom Tuskawilla villa, HOA maintains the lawn. This home boasts an open floor plan featuring beamed vaulted ceilings, a wood burning stone fireplace, an eat in kitchen and a spacious screened porch ROOF INSTALLED IN 2023, AC INSTALLED IN 2021, Resurfaced bath tub, shower and vanity countertops. Professional tennis courts and a clubhouse facility right across the street. Opportunity to join the Tuskawilla Country Club for golf, swimming, dining and more! NEW KITCHEN INSTALLED IN 2023! WITH UPDATED CABINETRY, QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES! CLOSET PANTRY & QUARTZ BREAKFAST BAR! Eat-in kitchen, vaulted ceilings with elegant wooden beams. Enjoy the living space outdoors in a large screened-in patio, enjoy your backyard, with 12 inch concrete tiles, vinyl fence for privacy, creating a relaxed setting for entertaining . Relax and enjoy the enclosed front porch with sliding door access to both bedrooms. Sliding door in the master bedroom with access to the ceramic tiled back screened porch. This home is near Trotwood Park, Cross Seminole Trail and Bear Creek Nature Trail. A short drive to Oviedo Mall, Winter Springs Town Center and the many parks in the area. The location is one of the best with quick access to the 417. The schools include some of the top-rated schools in all of Central Florida. Schedule your showing today, before it’s too late!
Listing is courtesy of: DIAMOND 2000 REALTY, INC (321-231-4195)
Listing Agent: Ramon Ortiz Cruz (321-231-4195)
721 GALLOWAY CT, WINTER SPRINGS, FL 32708
$359,90036 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
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)
408 AVONDALE CT, WINTER SPRINGS, FL 32708
$1,250,00065 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 Agent: Jennifer Christ (407-474-7823)
222 W PANAMA RD, WINTER SPRINGS, FL 32708
$310,000135 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
$454,90071 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)
506 CLUB DR, WINTER SPRINGS, FL 32708
$232,000211 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)
130 E BAHAMA RD, WINTER SPRINGS, FL 32708
$725,00064 Days on yellowkey MLS ID: O6398011
0 Days Off yellowkey (back on 5/9/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2158 Built: 1991 Tax: $3,366 (2024)Community: Bahama RanchesSingle Family
Taxes:$3,366
Remarks: Under contract-accepting backup offers. Don’t miss the opportunity to see this exceptional property! Located in the desirable Ranchlands neighborhood of Winter Springs, this exceptional property sits on over 1.5 acres of land, offering both space and privacy. A large circular driveway provides easy access and ample parking. This well-maintained home features 4 bedrooms, 2 bathrooms, and over 2,100 square feet of living space, with a split floor plan ideal for both everyday living and entertaining. As you enter, you’re welcomed by a bright, open interior showcasing tile flooring throughout the home, high ceilings, and an abundance of natural light. The upgraded kitchen is a standout, featuring stainless steel appliances, granite countertops, plenty of cabinet storage and a kitchen nook. The spacious family room includes a cozy fireplace, along with a mounted TV and surround sound system that will convey with the home. The primary suite offers private access to the backyard through sliding glass doors, a walk-in closet, and a generously sized en-suite bathroom complete with dual sinks, and a tub/shower combo. Step outside to enjoy the expansive covered lanai—perfect for relaxing or entertaining—along with a 30' above-ground pool to enjoy Florida’s warm weather and a play area for the little ones. Additional upgrades include a home generator, AC and septic tank and pump all installed in 2017, a water heater in 2018, pool in 2020, roof in 2021 and pool pump in 2026. In addition to the attached 2-car garage, the property also features a 25' x 30' detached garage equipped with electricity and AC—ideal for extra vehicles, a workshop, or storage. A side-entry gate provides access for RV or boat parking to store in your backyard. With no HOA, you’ll enjoy the flexibility to use the property as a primary residence, investment, or income-producing opportunity. This hidden gem offers a peaceful, country-style setting while still being conveniently located near major roads, shopping, and dining. Come see it today and make it yours!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Zac Hernandez (407-576-7622)
4910 E LAKE DR, WINTER SPRINGS, FL 32708
$2,399,00049 Days on yellowkey MLS ID: O6398929
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3657 Built: 1964 Tax: $6,256 (2024)Community: NaSingle Family
Taxes:$6,256
Elementary School: Sterling Park Elementary
Remarks: A truly rare find in Winter Springs. This equestrian-friendly, lakefront estate is complete with its own private tennis court, a solid block-constructed horse barn, and room to enjoy every part of the lifestyle. All of this, tucked in a quiet setting that keeps you close to the heart of Orlando, with the added benefit of being just 2 miles from The Geneva School, one of the area’s premier private education options. Originally built in 1964, the home was thoughtfully expanded in 1994, creating a larger, more functional layout while preserving its character. Today it offers over 3,000 SF overlooking the shimmering waters of Little Lake Howell. Enjoy west-facing sunset views framed by mature cypress trees. Host friends for tennis or pickleball right in your backyard. The sizeable horse barn was engineered for exceptional durability, built with block construction and poured concrete for maximum strength. The main home includes a 3-car garage, and the barn adds an oversized carport that can easily double as covered boat storage.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Kris Kennedy (813-947-3509)
600 NORTHERN WAY #1608, WINTER SPRINGS, FL 32708
$274,900119 Days on yellowkey MLS ID: G5108558
REDUCED by $5,100 (1.8%) on 05/01/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1425 Built: 1981Monthly Fee: $373 Tax: $2,582 (2025)Community: Tuscany PlaceCondo
Taxes:$2,582
Remarks: Very motivated sellers! Condo in Tuskawilla’s Tuscany Place •Discover comfort and convenience in Winter Springs’ Tuskawilla neighborhood. Tuscany Place is a gated community with a private pool, near Trotwood Park, Cross Seminole Trail, and top-rated schools. •Double Balcony (length of condo) •Corner unit with pool view •Updated kitchen w/stainless steel appliances •New water heater (2023) •New roof (2023) •New AC (2016) •Washer/dryer (2026) •Primary bedroom with walk-in closet, en-suite, and balcony access •Split floor plan for privacy. Seize this opportunity to own a beautifully updated condo in a prime location! FHA Approved Condo complex.
Listing is courtesy of: WORTH CLARK REALTY (352-988-7777)
Listing Agent: Kelly Boulton (407-906-8348)
130 DEER SONG DR, WINTER SPRINGS, FL 32708
$310,00077 Days on yellowkey MLS ID: O6395309
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1105 Built: 1994Monthly Fee: $127 Tax: $3,102 (2025)Community: Deersong 2Single Family
Taxes:$3,102
Remarks: Welcome to 130 Deer Song Dr in the heart of Winter Springs an exceptional opportunity to own one of the most beautifully updated homes in the community! Positioned on a desirable corner lot with ample parking, this fully renovated 3-bedroom, 2-bathroom home stands out as a rare find offering both style and convenience. From the moment you step inside, you’ll notice the thoughtful upgrades throughout, including brand-new flooring, a completely redesigned kitchen, modernized bathrooms, updated plumbing, and new energy-efficient windows. all creating a truly move-in-ready experience. Major systems have already been taken care of for peace of mind, with the roof replaced in 2015 and AC updated in 2019. Step outside to your own private, fully fenced backyard oasis, featuring a paved outdoor space and covered patio perfect for entertaining, relaxing, or enjoying Florida living year-round. The property also includes a detached storage space, offering additional functionality and convenience. Located directly across from the community pool and amenities, you’ll enjoy easy access to everything this well-maintained neighborhood has to offer. The location is unbeatable just minutes from Winter Springs Town Center, Seminole County Bike Trail, Oviedo Mall, Publix, restaurants, and everyday essentials, along with nearby fire and police services for added peace of mind. This home checks all the boxes: location, upgrades, lifestyle, and value. Opportunities like this don’t come often, schedule your private showing today and see why this is truly one of the best homes in the neighborhood!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Yosseff Roman (407-394-5843)
471 HARBOR WINDS CT, WINTER SPRINGS, FL 32708
$330,000106 Days on yellowkey MLS ID: O6387316
REDUCED by $5,000 (1.5%) on 04/16/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1680 Built: 2008Monthly Fee: $298 Tax: $4,552 (2024)Community: Harbor WindsTownhouse
Taxes:$4,552
Remarks: Experience the perfect blend of location and low-maintenance living at 471 Harbor Winds Court. Located in a secure, gated Winter Springs community, this move-in ready home offers ultimate peace of mind with a NEW ROOF (2024). The functional interior features a rare and highly desired Large Primary Suite on the Main Floor, complete with dual closets for abundant storage. The open, inviting layout flows seamlessly to your private, screened-in patio—ideal for year-round relaxation or entertaining. Enjoy the convenience of a spacious 2-car garage and plenty of guest parking throughout the community. Harbor Winds residents enjoy amenities, including a refreshing community pool and meticulously maintained grounds. Conveniently located near top-rated Seminole County schools, shopping, and dining, this home is a great find. This is your chance to own a meticulously maintained townhome in a premier gated community!***BUYER INCENTIVE: Closing cost a concern? The seller is offering a 1% Lender Credit toward the buyer's closing costs or rate buy-down when using the seller's preferred lender!***
Listing Agent: Terrica Francois (407-680-8268)
1113 CITRUS OAKS RUN, WINTER SPRINGS, FL 32708
$685,00072 Days on yellowkey MLS ID: O6397034
0 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2353 Built: 2001Monthly Fee: $127 Tax: $3,886 (2024)Community: Citrus OaksSpa: NoSingle Family
Taxes:$3,886
Remarks: Under contract-accepting backup offers. Welcome to 1113 Citrus Oaks Run, a beautifully maintained home offering timeless style, functional space, and a private backyard retreat. This spacious 3-way split floor plan features wood flooring throughout, 8-foot doors, high ceilings, and elegant beams in the dining room, creating a warm and inviting atmosphere from the moment you enter. The living room/den showcases added French doors, while the updated kitchen overlooks the family room and features refinished cabinetry with soft-close features, updated countertops, pantry storage, and a cozy dinette area. The primary suite opens to the pool through sliding doors and includes a walk-in closet and an en-suite bath with updated counters, while the secondary wing offers two bedrooms with a beautifully remodeled bathroom and linen storage, plus a third bedroom and another fully renovated bath. Plantation shutters throughout add charm and privacy, and the laundry room is conveniently located just off the garage. Outside, enjoy a fully fenced wrought-iron yard and a screened pool area with a recently redone pool cage, perfect for relaxing or entertaining. Additional highlights include a 3-car garage with shelving and attic storage, water softener, A/C approximately 3 years old, and roof approximately 6 years old—making this move-in-ready home an exceptional opportunity in a desirable Winter Springs location.
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Abby Nelson (407-571-1445)
498 CLUB DR, WINTER SPRINGS, FL 32708
$235,000315 Days on yellowkey MLS ID: O6332792
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1224 Built: 1987Monthly Fee: $360 Tax: $2,970 (2024)Community: Cypress ClubTownhouse
Taxes:$2,970
Remarks: Welcome to Cypress Club, a townhome community located in The Highlands within Winter Springs. Two bedrooms/two bath home is two stories offering split bedrooms. The living room/dining room combo provides high lofty ceilings with celestial windows providing natural sunlight to the home. Sliding glass doors open to a screen enclosed patio to the rear of the property that overlooks Winter Springs peaceful conservation area. Open stairwell that leads to the loft where you will find a spacious laundry arrangement set up. The master bedroom and bath are on the second floor. The home has been freshly painted. The Highlands offers many amenities to include tennis/pickle ball courts, basketball and volleyball, park with BBQ areas and a covered pavilion and boasts it's Junior Olympic size swimming pool. Playgrounds throughout the community. Cypress Club also provides a community pool. The roof is new 2026.
Listing is courtesy of: PAINE-ANDERSON PROPERTIES, INC (407-695-7898)
Listing Agent: Joyce Gary (407-782-3276)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.