Homes for Sale Near Indian Trails Middle in Winter Springs - 105 homes

Remarks: Improved Price: Your Time to Win. THIS IS THE ONE you’ve been waiting for in Winter Springs. This spacious 4-bedroom, 2.5-bath home with 2,152 SqFt offers the perfect combination of space, flexibility, and income potential. Located in a non-flood zone with low HOA and NO rental restrictions, this is a rare find for both homeowners and savvy investors. Featuring a unique three-level layout, the home includes formal living and dining areas plus a versatile Family room—perfect for movie nights, game days with friends, or even unforgettable family karaoke evenings. Step outside and get ready to fall in love. The fully fenced backyard is built for lifestyle: the spacious covered and screened terrace invites you to enjoy your morning coffee by a charming gas fire pit, unwind with evening cocktails, roast marshmallows around a natural fire pit, or host the perfect BBQs. The outdoor space also features a small play area, while still offering ample room for pets to run freely. This is Florida living done right. Freshly painted, meticulously maintained, with updated bathrooms and a functional kitchen ready for immediate enjoyment. For added value and peace of mind, the property includes a water softener system throughout the home and an alkaline water filtration system at the kitchen sink—features today’s buyers truly appreciate. Located near top-rated Seminole County schools, parks, shopping, and major highways with easy access to Orlando. Opportunities like this are rare and move FAST. Schedule your private showing TODAY before it’s gone.

Listing is courtesy of: HOME PRIME REALTY LLC (813-497-4441)

Listing Agent: Fara Ramirez Labrada (813-389-1489)

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)

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)

Remarks: Under contract-accepting backup offers. Welcome to 408 Avondale Court, a custom estate built by Von Jacobs in 2003 & located in the highly desirable, gated Wicklow Greens community in Winter Springs. Set among just 48 custom homes, this stunning residence sits on arguably one of the best lots in Tuscawilla. This .48 acre property is situated in the rear of the neighborhood, on a quiet cul-de-sac where you can enjoy serene views of conservation & Howell Creek in the back. This home features 5 bedrooms, 4.5 bathrooms, and 3,850 square feet of thoughtfully designed living space. From the moment you enter, you’ll appreciate the elegance of wood flooring throughout the first floor, soaring ceilings, and the ideal layout for both everyday living and entertaining. The generously sized kitchen features wood cabinetry, a long center island that offers plenty of countertop space for meal prep, a wet bar, and ample seating space. All 5 bedrooms are conveniently situated on the lower level, with an oversized 650 sq ft loft & 4th full bathroom upstairs. This layout is ideal, offering several options no matter your stage of life. Step outside to your private backyard retreat, which features pavers, a pool and a gas-heated spa, surrounded by peaceful conservation views—the perfect place for relaxing evenings or weekend gatherings.This home has been meticulously maintained by its original owner and updated with major improvements including a new roof (2022), exterior paint (2022), and newer mechanical systems such as A/C units (2015 & 2016) and water heaters (2022 & 2016). A 3-car side-entry garage completes the picture, offering both convenience and curb appeal. Ideally located just minutes from the Tuscawilla Country Club, residents can enjoy convenient access to golf, dining, and social membership opportunities, making this home perfect for those seeking an elevated Central Florida lifestyle. The community is zoned for top-rated schools including Winter Springs High, Indian Trails Middle, and Rainbow Elementary, with additional private school options nearby, such as The Geneva School, Masters Academy, St. Luke’s, Trinity Prep, and Choices in Learning charter school. This is a rare opportunity to own a luxury home in one of Winter Springs’ most coveted gated neighborhoods. So hop onto your golf cart, and zip on by to see this beauty before it's too late!

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Jennifer Christ (407-474-7823)

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)