Browse All Winter Springs FL Historical Properties for Sale

Exceptional investment and owner-user opportunity on highly traveled SR 434. This well-maintained professional office building offers the ideal combination of income potential and flexibility in one of the Longwood/Winter Springs area's most visible commercial corridors. Designed to accommodate multiple tenants or a single owner-occupant, the building features separate first and second-floor suites, creating a variety of leasing and occupancy options. The second floor is ideally suited for professional, medical, legal, financial, or service-oriented businesses and features five private offices, spacious reception and waiting areas, two private restrooms, a large break room with abundant storage, a front-facing balcony, and private rear stair access. A shared conference room is available as part of the common area, providing added convenience for both levels. The property has been thoughtfully updated over the years and offers ample on-site parking, excellent accessibility, and outstanding frontage along SR 434 with exceptional visibility and signage opportunities. Surrounded by established businesses and just minutes from I-4, Ronald Reagan Boulevard, and the Lake Mary business corridor, this location provides convenient access for clients, customers, and employees alike. Whether you're expanding your business, seeking a value-add investment, or looking for a property that offers both immediate usability and long-term income potential, this professional office building presents an outstanding opportunity in the heart of Seminole County.

925 W Sr 434, Winter Springs

$205,900

2 Beds ⋅ 2 Baths ⋅ North Orlando 1st Add SubDv. ⋅ 32708 Zip Code

Under contract-accepting backup offers. Set in the heart of Winter Springs, 71 Bombay Ave offers the kind of opportunity buyers are always looking for: an established location, a functional footprint, and the chance to create a home that reflects their own style. This property is ready for its next chapter, making it an ideal choice for those who appreciate potential, value, and the ability to personalize a space over time. Life here puts you close to the everyday conveniences and outdoor lifestyle that make Winter Springs so appealing, from nearby parks and playgrounds to community favorites like Central Winds Park, nature trails, sports fields, dog-friendly spaces, and access to the Cross Seminole Trail for biking, walking, and weekend exploring. The area offers a relaxed residential feel while still keeping you connected to Oviedo, Tuscawilla, Winter Springs Town Center, shopping, dining, and major Central Florida corridors. Whether you are looking to renovate, invest, or design a home that feels entirely your own, this property offers a rare chance to bring fresh vision to a well-located Winter Springs address.

71 Bombay Avenue, Winter Springs

$2,299,000

3 Beds ⋅ 3 Baths ⋅ Na SubDv. ⋅ 32708 Zip Code

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.

4910 E Lake Drive, Winter Springs

$214,000

2 Beds ⋅ 1 Baths ⋅ North Orlando SubDv. ⋅ 32708 Zip Code

Under contract-accepting backup offers. Charming ranch-style home brimming with potential and ready for your personal touch! Ideally situated in a convenient location, this property offers easy access to nearby schools, shopping centers, public transportation, and everyday essentials. Inside, you’ll find a practical layout featuring 2 comfortable bedrooms and 1 full bathroom, along with durable terrazzo and tile flooring throughout—perfect for low-maintenance living. The home also boasts a spacious enclosed lanai, providing a versatile area that can be used for relaxing, entertaining, or even creating a cozy sunroom or hobby space. From here, enjoy peaceful views of the large, fenced backyard—ideal for pets, gardening, or outdoor gatherings. With its solid structure, desirable location, and endless possibilities for updates or expansion, this property is a fantastic opportunity for homeowners and investors alike.

120 N Fairfax Avenue, Winter Springs

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