Homes for Sale Near Winter Springs High in Longwood - 9 homes

Remarks: Priced to sell, this updated 3-bedroom, 2-bath home offers 1,101 square feet in a prime Longwood location with strong upside potential. Featuring a bright, functional layout, updated finishes, spacious bedrooms, and a private backyard, the property is move-in ready with room to further increase value through use optimization or enhancements. A standout feature is the Mixed Use Dwelling (MUD) zoning, allowing for both residential occupancy and approved light commercial use. This rare flexibility creates multiple exit strategies—live/work setup, small business operation, short- or mid-term investment hold, or future income-producing configuration (subject to local zoning regulations and approvals). With its central location near major corridors, retail, and established residential growth, this property is positioned for strong long-term demand and versatility. Conveniently situated near Historic Downtown Longwood, SunRail, shopping, dining, major roadways, and top local amenities, this property combines affordability, location, and long-term potential. Whether you're looking for a primary residence, rental property, house hack opportunity, or future investment, this home is one you won't want to miss. This home can be purchased with NO MONEY DOWN, or NO INCOME VERIFICATION!!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Eve Logan (407-227-3171)

Remarks: Under contract-accepting backup offers. Virtually Staged. Highly sought after Seminole County Pool Home on a Corner Lot for under $350,000!!! This deal can't be beat and the location is even better! Just a very short WALK to the dog park all fenced in and the famous Candyland Park! Updated kitchen and master bathroom in 2026 and the whole house was repiped in 2024. Centrally located in Longwood to enjoy all the restaurants, parks, shopping and a quick commute to downtown Orlando and less than an hour to the sandy beaches or all the theme parks! This huge corner lot home with perfectly placed shade trees also offers an oversized Florida room/Patio AND artificial turf near the pool for the ultimate hang out spot for a little putt putt and very low maintenance! If you are looking for the perfect place to call home, this is it!!

Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)

Listing Agent: Christopher Schiffermiller, Llc (407-409-5702)

Remarks: Incredible Duplex on a large lot in Longwood. With a city park, Small World Park, literally behind the house! Both sides (640 & 638) for only $285,000 with over 1,900 sq ft under air. Tenants are moving out in the next 10 to 14 days. Selling the property "As Is" Sellers say sell. Highest and best offer after 10 days.

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

Listing Agent: Tim Malone (407-765-6987)

Remarks: Virtually Staged. Welcome to 1508 Canary Street in Longwood! This charming 4-bedroom, 2-bath home features a desirable split floorplan, offering both privacy and functionality for everyday living. With no HOA, you’ll enjoy the freedom to truly make this property your own. Step outside to a spacious, fully fenced backyard with mature trees, perfect for relaxing, entertaining, or letting pets roam freely. Whether you're hosting gatherings or simply enjoying a quiet evening at home, this outdoor space offers endless possibilities. Air conditioning, water heater, electric and plumbing have been updated. Conveniently located near shopping, dining, and major roadways, this home is a great opportunity to enjoy comfortable living in the heart of Longwood.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Dawn Grigsby (407-970-9051)

Remarks: This beautifully maintained 3-bedroom, 2.5-bath townhome was built in 2023 and has been barely lived in, offering the feel of brand-new construction without the wait. Featuring approximately 1,488 square feet of thoughtfully designed living space, this home boasts an open-concept floor plan perfect for both everyday living and entertaining. The modern kitchen showcases stainless steel appliances, ample cabinetry, generous counter space, and a convenient breakfast bar overlooking the spacious living and dining areas. Upstairs, you'll find a private owner's suite with a walk-in closet and en-suite bath, along with two additional bedrooms, a full bathroom, and a dedicated laundry area. Enjoy the convenience of a 2-car garage, smart home features, and low-maintenance townhome living. Located just minutes from Historic Downtown Longwood, SunRail, shopping, dining, parks, and major roadways, this move-in ready home offers the perfect blend of comfort, style, and location. Don't miss your opportunity to own this like-new townhome in one of Longwood's most convenient locations!

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Mandy Minnetto (407-383-0006)

Remarks: Investor or first time buyer opportunity in Longwood. This 1/2 duplex offers 2 bedrooms, 2 bathrooms, a private 1-car garage, and its own backyard. 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. Tenants just vacated. Some interior updates pending. 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 home to the heart of Longwood! This charming 3-bedroom, 1.5-bath home features luxury plank tile throughout and an open, cozy living room perfect for everyday comfort. Enjoy peace of mind with major updates already completed, including a new roof in 2023, HVAC in 2019, an updated water heater, and electrical improvements. The spacious backyard offers plenty of room to relax, entertain, or create your own outdoor retreat. Centrally located near major highways and the SunRail system, commuting is a breeze with convenient access to Central Florida attractions. Nature lovers will appreciate being close to Wekiva Island and Big Tree Park, while downtown Longwood’s Reiter Park and weekly farmers market add local charm just minutes away.

Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)

Listing Agent: Crystal Yovaish (407-496-8672)

Remarks: Under contract-accepting backup offers. Situated on an oversized double lot in the heart of Longwood, this 2-bedroom, 1-bath home offers endless potential for homeowners and investors alike. Offering a spacious living room, a functional kitchen, and an updated bathroom with walk-in shower, the home also features tile flooring throughout the main living areas and carpet in the bedrooms, making it ready for someone to move in and make it their own. Just off the kitchen and dining area, a recently installed patio creates the perfect outdoor entertaining space, complete with corner posts ready for shade sails or a custom covered seating area. The large lot provides mature landscaping, beautiful shade trees, and ample space to park an RV, boat, or additional vehicles with no HOA restrictions. Additional features include a covered carport with separate laundry room and utility sink, an extra storage room at the rear of the home, and a detached storage shed with an attached covered storage area ideal for lawn equipment, tools, or outdoor gear. Roof replaced in 2015, water heater installed in 2022, New Washer & Dryer 2022, and connected to public sewer. Whether you're searching for your first home, a solid investment property, or a home with room to expand and make your own, this versatile property offers endless possibilities.

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

Listing Agent: Kerry Stafford (407-821-8600)

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)