Homes for Sale Near South Seminole Middle in Winter Springs - 29 homes

Remarks: Under contract-accepting backup offers. Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy the benefits of a new roof 2026, new water heater 2026, 2020 A/C system, a full repipe completed in 2016, and a 2016 whole home water softener. Inside, you’ll find an inviting layout with knockdown ceilings throughout the main level and an open living and dining area tucked toward the rear of the home for added privacy. Updated recessed lighting enhances the space, creating a warm and welcoming atmosphere. Just beyond, a step-down enclosed patio offers a serene retreat overlooking wooded views—perfect for relaxing or entertaining. The flexible floor plan includes a downstairs bedroom with an adjacent full bath, ideal for guests, a home office, or multi-generational living. Upstairs, two generously sized bedrooms feature soaring ceilings and abundant natural light. The primary suite offers ample closet space and tranquil views of the surrounding greenery, along with a spacious en-suite bath complete with a Jacuzzi tub and separate shower—perfect for unwinding after a long day. Cypress Club stands out as the only neighborhood within The Highlands with its own private pool, in addition to access to the community’s extensive amenities. Residents enjoy multiple pools, tennis courts, scenic walking trails, parks, pavilions, BBQ areas, a clubhouse, as well as volleyball and basketball courts—delivering a true Florida lifestyle right outside your door. Don’t miss this opportunity to own a move-in-ready home in one of Winter Springs’ most desirable communities!

Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)

Listing Agent: Jeff Singletary (407-383-1933)

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)

Remarks: NEW TILE ROOF INSTALLED APRIL 2026 + TRANSFERABLE 4-POINT INSPECTION + APPROXIMATELY 5-MINUTE WALK TO HIGHLANDS ELEMENTARY! Welcome to 622 Anhinga Road, a move-in-ready home located in the highly desirable Greenspointe community of Winter Springs. One of the most expensive updates a homeowner can face has already been completed with a BRAND-NEW TILE ROOF installed in April 2026, providing long-term value, durability, and peace of mind for years to come. To make the buying process even easier, the seller has already completed a transferable 4-Point Inspection available to the new owner. This beautiful 3-bedroom, 2.5-bathroom home offers over 1,700 square feet of living space and a highly desirable floor plan with the primary suite conveniently located on the first floor. The spacious owner's retreat features a large walk-in closet and a private bathroom with dual vanities, a soaking tub, separate shower, and private water closet. As you enter the home, you'll immediately notice the soaring ceilings, abundant natural light, and open-concept layout that creates a bright and welcoming atmosphere. The main living areas feature tile flooring throughout, while the kitchen offers granite countertops, stainless steel appliances, light cabinetry, a breakfast bar, and views of the living and dining areas—perfect for everyday living and entertaining. Sliding glass doors lead to a shaded backyard, creating the perfect space for relaxing, grilling, entertaining guests, or simply enjoying Florida evenings. Upstairs, you'll find a spacious loft that can easily serve as a home office, media room, playroom, gym, or second living area, along with two additional bedrooms and a full bathroom. Families will love the location within the highly rated Seminole County School District. Highlands Elementary School is just a short walk from the home, allowing many residents to enjoy the convenience of walking their little ones n to school in approximately 5 minutes. South Seminole Middle School and Winter Springs High School are also nearby. Residents enjoy access to The Highlands community amenities, including a community pool, tennis courts, pickleball courts, basketball courts, playgrounds, parks, clubhouse, walking trails, and recreational facilities designed for an active Florida lifestyle. Conveniently located near Winter Springs Town Center, UCF, Valencia College, shopping, dining, SR-417, SR-434, I-4, Downtown Orlando, and Central Florida attractions, this home offers both comfort and convenience in one of Seminole County's most sought-after communities. Vacant and easy to show. Major updates already completed, including a NEW TILE ROOF (April 2026), HVAC (2017–2018), WATER HEATER (2022), and a TRANSFERABLE 4-POINT INSPECTION. A rare opportunity to own a move-in-ready home in Winter Springs with top-rated schools, outstanding community amenities, and important updates already taken care of.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)

Listing Agent: Alexa Monasterio Flores (786-915-9294)

Remarks: BACK ON THE MARKET DUE TO BUYERS FINANCING FALL TROUGH!! Beautifully maintained home located in one of the most desirable areas of Winter Springs, offering the perfect blend of comfort, convenience, and outdoor living. Surrounded by scenic walking and biking trails throughout the neighborhood, this home delivers a peaceful setting while staying close to everything you need. This property features 3 bedrooms and 2 bathrooms with a bright open floor plan ideal for both everyday living and entertaining. The kitchen is equipped with stainless steel appliances and flows seamlessly into the main living areas, creating a spacious and inviting atmosphere. Step outside to your private screened pool area, perfect for relaxing or hosting gatherings, all within a fully fenced backyard that provides excellent privacy. Whether enjoying Florida sunshine or evening outdoor dining, this space is designed for year-round enjoyment. Conveniently located near shopping centers, restaurants, and major highways, offering easy access to Orlando, employment hubs, and surrounding communities while still enjoying the charm of a sought-after residential area. This home combines a desirable location, functional layout, and outdoor lifestyle — making it an excellent opportunity for homeowners and long-term value. Some photos were virtually staged.

Listing is courtesy of: CAISSA REALTY INVESTMENT INC (407-364-3056)

Listing Agent: Elizabeth Rodriguez (407-480-8829)

Remarks: One or more photo(s) has been virtually staged. ONE OF A KIND! Stunning Renovated Lakefront Home on Private Peninsula – Welcome to your fully reimagined lakefront retreat at 1444 Bird Road in the heart of Winter Springs. Nestled along the serene shores of Lake Tony, this highly detailed, professionally rehabbed home blends modern luxury with timeless Florida charm. From the moment you arrive, you’ll notice the thoughtful craftsmanship and attention to detail throughout. The home has been completely renovated from top to bottom, featuring a bright, open-concept layout with abundant natural light and stunning lake views from multiple living spaces. The designer kitchen is a true centerpiece, showcasing amazing cabinetry, premium quartz countertops, stainless steel appliances, and a spacious island perfect for entertaining. The living and dining areas flow seamlessly, creating an inviting space for gatherings or quiet evenings overlooking the water. Retreat to the primary suite, where you’ll find a spa-inspired bathroom with high-end finishes, elegant tile work, and a relaxing atmosphere designed for comfort. Additional bedrooms offer flexibility for guests, family, or a home office. Step outside to your private backyard oasis, where you can enjoy peaceful mornings or breathtaking sunsets on Lake Tony. Whether you’re kayaking, fishing, or simply unwinding by the water, this property offers the ultimate lakefront lifestyle. Additional upgrades include updated systems, modern fixtures, and quality finishes throughout—providing peace of mind and move-in-ready convenience. Located in a desirable Winter Springs neighborhood with easy access to top-rated schools, parks, shopping, and dining, this home is a rare opportunity to own a turnkey lakefront property. Don’t miss your chance to experience luxury living on Lake Tony—schedule your private showing today.

Listing is courtesy of: KEEN REALTY GROUP, INC. (407-699-2127)

Listing Agent: Bobby Keen (407-951-2300)

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)

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)

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)

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)