Homes for Sale Near Winter Springs High in Longwood - 8 homes

Remarks: Charming Renovated 3-Bedroom Home with Spacious Yard — Move-In Ready! Welcome home to this beautifully updated 3-bedroom, 2-bath residence full of charm and modern touches! Perfectly situated in a friendly, working-class neighborhood, this home offers the perfect blend of comfort, style, and everyday practicality. Step inside to find a bright, open layout featuring fresh paint, updated flooring, and a thoughtfully renovated kitchen and bathrooms. Every detail has been designed to make daily living easy and enjoyable — from the comfortable living spaces to the convenient single-car garage for parking or extra storage. Outside, you’ll love the .24-acre lot with no trees and a huge shed INCLUDED, offering a wide-open yard that’s perfect for pets, play, or creating your dream outdoor space. There’s plenty of room to add a patio, garden, the possibilities are endless! Whether you’re a first-time buyer, small family, or someone looking to downsize, this home offers an affordable and move-in-ready opportunity to put down roots and make it your own. Don’t miss your chance to own this charming, renovated gem — schedule your showing today!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Uwem Akpan (689-837-2197)

Remarks: Under contract-accepting backup offers. Welcome to your FLORIDA dream oasis in the heart of Longwood where comfort meets leisure in a single-family residence nestled on a generous .40-acre lot. VIEW VIRTUAL WALK THRU TOUR. Seller is currently in the process of doing a full re-pipe. This charming 3/2 POOL home is designed for both everyday living with entertainment options for everyday or just the weekends. Make everyday a holiday with a HUGE screened porch/pool area. Incredible lifestyle opportunities with this home that has so much potential. As you approach the property, the beautifully oversized lot greets you with a circular driveway, providing ample parking for up to 6 vehicles. The absence of an HOA means you can bring your RV, boat, and all your toys, enjoying the unlimited parking space and the convenience of a double gate leading to a fully fenced backyard. Step inside to find an updated kitchen boasting modern appliances, perfect for crafting delicious meals for family and friends. The all-tile flooring throughout the home ensures easy maintenance and a timeless appeal. Enjoy the luxury of an in-ground swimming pool, where you can take a refreshing dip or simply lounge by the water on sunny Florida days. If you want a pool you need to buy a home with an existing pool. Entertain in style within the large screened area, ideal for hosting gatherings or simply relaxing in the serene outdoor environment. Even has a dart board for fun! The single-car garage, upgraded electrical system, and outdoor shower add to the practicality and charm of this delightful home. Perfect for all lifestyle and family needs with the entire home on ONE FLOOR. Located in the highly sought-after Seminole County School district and conveniently close to shopping, restaurants, and I-4, 821 Raven provides the perfect blend of tranquility and accessibility. Make this your new haven for family fun and a relaxing new lifestyle in your own home! Why rent when you can own your own FLORIDA home. This one is about the pool and the fenced large yard with no HOA! Make it your own!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Laurie Cain (407-484-9944)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to 1508 Meadowlark Street — a beautifully updated home offering comfort, style, and peace of mind. Tucked away with a serene conservation view and no rear neighbors, this property offers the kind of backyard privacy that’s hard to find. Inside, you’ll love the spacious main bedroom with a walk-in closet and built-in organizer system, along with an updated kitchen featuring modern countertops and a stylish backsplash that adds a fresh, contemporary feel. Also enjoy the luxury of a SMART thermostat and solar light. Major improvements have already been completed, including a new roof (2022), A/C (2022), A/C ducts (2024), electrical panel (2022), re-pipe (2022), appliances (2022) including a SMART washer and dryer, new carpet (2022), and fresh paint (2022). With no HOA and so many big-ticket updates already taken care of, this move-in ready Longwood home is an exceptional opportunity. Close to downtown Longwood and Winter Springs offering a plethora of shopping, dining, and entertainment options. Near major highways such as the I4 making commute to major theme parks, downtown Orlando, Orlando International or Sanford International Airports, beaches and more a breeze! Perfect for everyone from 1st time home buyers to investors alike! Come see today before it's gone!

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

Listing Agent: Christina Rampersad (407-995-6788)

Remarks: Step into modern living in the heart of Historic Longwood! Built in 2023, this beautifully designed townhome at 553 John L. Mica Way blends contemporary comfort with the charm and convenience of one of Longwood’s most beloved districts. Clean lines, energy-efficient construction, and thoughtful finishes create a home that feels both stylish and effortless from the moment you walk in. Located just moments from Downtown Longwood, you’re perfectly positioned to enjoy the city’s vibrant local scene—farmers markets, community events, boutique shops, parks, and the SunRail station are all within easy reach. Whether you’re commuting, exploring, or savoring the neighborhood’s historic character, this address puts you right where you want to be. Inside this end unit, the open-concept layout, modern kitchen, and 3 spacious bedrooms provide a turnkey lifestyle with all the benefits of newer construction: low maintenance, smart design, and peace of mind. With its unbeatable location and fresh, contemporary feel and low monthly HOA, this townhome is an ideal fit for anyone looking to enjoy the best of Longwood living. Schedule your showing today!

Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)

Listing Agent: Michelle Deleon (407-619-7056)

Remarks: Beautifully Maintained Pool Home – No HOA! This inviting pool home blends comfort, style, and updates throughout – plus the freedom of no homeowners association. Freshly painted interior with a bright, welcoming feel, New appliances in the kitchen with solid wood cabinetry and pull-out drawers Newly resurfaced pool (2017 - 2025) – sparkling and ready for year-round enjoyment,New ceiling fans.bathrooms were remodeled 2021. Expansive screened pool deck ideal for entertaining or relaxing outdoors,Updated master bath with modern finishes Air handler replaced i 2019 .Master suite with sliding glass doors opening to the pool and patio Large backyard shed for storage plus a side workshop for hobbies or projects for peace of mind Fantastic Location: Near major roads 17-92 and 434, just 10 minutes to I-4, close to hospitals, restaurants, shopping, and more. Don’t miss the opportunity to own this move-in ready pool home in one of the most convenient areas of Central Florida!

Listing is courtesy of: INVESTOR'S REAL ESTATE LLC (407-688-4355)

Listing Agent: Patty Perez Renteria (407-927-4731)

Remarks: Investor opportunity in Longwood. This 1/2 duplex offers 2 bedrooms, 2 bathrooms, a private 1-car garage, and its own backyard. Best part: it is tenant occupied, so you already have built-in income in place. No HOA means no monthly dues cutting into your return. That is one less headache and one less bill, which feels almost suspiciously efficient. Located in desirable Seminole County, this property puts you close to everyday essentials, shopping, dining, and major roadways including 417 and I-4 for easy access across Central Florida. Property highlights: 1/2 duplex in Longwood 2 bedrooms, 2 bathrooms Private 1-car garage Private backyard Tenant occupied for immediate rental income No HOA Convenient Seminole County location Near shopping, dining, 417, and I-4 Whether you are growing your portfolio or looking for a smart, low-maintenance investment, this property checks the boxes. Submit your offer today!

Listing is courtesy of: ALL COUNTY CFL PROPERTY MGMT (407-802-2379)

Listing Agent: Vicky Ramos (689-231-6171)

Remarks: Welcome to this well-maintained property located in the heart of Longwood! This home offers a functional layout with comfortable living spaces, ideal for a variety of lifestyles. Conveniently situated near SunRail, major shopping centers, hospitals, and with easy access to Orlando International Airport, making daily commuting and travel simple and efficient. Enjoy the benefit of no HOA and low annual property taxes. Whether you're looking for a primary residence or a property with great long-term potential, this home is a must-see. Schedule your private showing today!

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Celines Pomales (407-373-8250)

Remarks: Under contract-accepting backup offers. This fully renovated home blends style and functionality with a bright, open layout designed for today’s lifestyle. From the moment you step inside, you’ll notice the fresh finishes, updated flooring, and abundant natural light that create a warm and inviting atmosphere. The kitchen has been completely upgraded and serves as the centerpiece of the home, featuring sleek countertops, modern cabinetry, stainless steel appliances, and ample prep space, perfect for both everyday living and entertaining. The spacious living and dining areas flow seamlessly, making the home feel open yet comfortable. The primary suite offers a private retreat with an updated en-suite bathroom and two additional bedrooms, providing flexibility for guests. Both bathrooms have been thoughtfully remodeled with contemporary finishes. With major updates already completed, this home offers the peace of mind today’s buyers are looking for, move-in ready and designed for low-maintenance living. Conveniently located in Longwood, just minutes from major highways, shopping, dining, and entertainment, this property combines modern upgrades with an unbeatable location. If you’re searching for a fully renovated home in Longwood with 3 bedrooms and nearly 1600 square feet, 410 Georgia Ave is one you won’t want to miss. New roof (2026), New AC (2026), Water Heater (2026).

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Mario Zendeli (407-325-3893)