Osteen Homes for Sale

AN AMAZING OPPORTUNITY FOR SOMEONE WITH VISION!!! Unleash your imagination with this incredibly unique, historic property situated on a sprawling 0.39-acre double lot in the heart of Osteen. Built in 1901 and brimming with old-world charm, this mixed-use compound (Zoned 01B4) is the ultimate blank canvas for an investor, entrepreneur, or creative owner. The massive, approximately 4,800 sq. ft. 3-story main building features a spectacular, wide-open floorplan on the ground level—providing an incredible footprint for your business or community concepts. Upstairs, you'll find charming loft bedrooms and ample storage space to suit your residential or office needs.The value doesn't stop at the main building! This parcel is a true compound, featuring a complete 2nd house on the property that is perfect for generating immediate rental income, hosting guests, or serving as a caretaker's residence. Multiple storage sheds surround the perimeter, making this a dream setup for housing equipment, excess inventory, or creating dedicated workshop spaces.With its classic frame construction, durable metal roof, and incredible footprint, the possibilities here are truly limitless. Transform this expansive space into a lively dancehall, a community church, a unique general store, a quaint bed & breakfast, or capitalize on individual rental rooms. Only your imagination limits you. Properties with this much square footage, flexibility, and character rarely hit the market. Bring your vision and make this Osteen landmark your very own!

195 Railroad Avenue, Osteen

Listing courtesy of WORTH CLARK REALTY. 352-988-7777

$599,000

4 Beds ⋅ 3 Baths ⋅ O6427266 MLS

NEWER CONSTRUCTION + OVER HALF AN ACRE + NO HOA! Why settle for a small lot and HOA restrictions when you can have a beautifully maintained 2022-built home with room to spread out? Offering 4 bedrooms, 2.5 baths and over 2,100 square feet, this Osteen home combines the modern finishes buyers want with the space and freedom that's becoming harder to find. The open kitchen features quartz countertops, stainless steel appliances, a large center island, pantry and abundant cabinetry, all flowing into the dining and living areas. The split-bedroom floor plan provides privacy for the spacious primary suite with a beautifully finished ensuite bath and custom walk-in closet. Outside is where this property really separates itself. Enjoy more than half an acre with a fully fenced backyard, mature citrus trees, a powered storage shed, covered lanai with a remote-controlled retractable screen and a custom pergola that's ready for grilling, entertaining or relaxing outdoors. And the upgrades go well beyond appearances. A Generac whole-house generator installed in 2025, Andersen Low-E windows, spray-foam insulated garage, water softener, high-capacity water heater and upgraded laundry room add comfort, efficiency and peace of mind. If you've been searching for newer construction without giving up land, privacy and flexibility, this is the opportunity you've been waiting for. Come experience what makes 125 Longwood Drive different.

125 Longwood Drive, Osteen

Listing courtesy of COLDWELL BANKER REALTY. 407-352-1040

$799,900

4 Beds ⋅ 3 Baths ⋅ O6419863 MLS

Welcome to your private country retreat in desirable Osteen! Nestled on over 10.66 acres, this spacious 4-bedroom, 3-bathroom home offers the perfect blend of comfort, functionality, and peaceful rural living. Step inside to discover a thoughtfully designed split-bedroom floor plan featuring a formal living room, a spacious family room, and a dedicated dining area—ideal for both everyday living and entertaining. The open kitchen is the heart of the home, boasting stainless steel appliances, abundant counter space including an island, and plenty of room to prepare meals while staying connected with family and guests. The oversized primary suite easily accommodates king-size furniture and provides a relaxing escape at the end of the day. The private, ensuite bathroom features a walk-in shower, a garden soaking tub, and ample space to unwind. The guest bedrooms are located on the other side of the home and offer spacious closets. One of the rooms provides a double primary suite with a walk in closet and its own bathroom. An inside laundry room is an added feature that adds everyday convenience. Step outside to the covered, screened lanai overlooking the sparkling pool—an ideal place to enjoy your morning coffee, host gatherings, or simply take in the peaceful surroundings. Bring your horses, goats, chickens, and more! With over 10.66 acres of usable land, this property offers endless possibilities for farming, recreation, or creating your own private estate. Enjoy the tranquility of country living while remaining conveniently located near shopping, dining, and major roadways. Don't miss this rare opportunity to own acreage in one of Osteen's most sought-after locations!

1005 Whispring Creek Way, Osteen

Listing courtesy of HUGHES HOMES REALTY. 407-557-8775

$1,111,000

3 Beds ⋅ 3 Baths ⋅ NS1086140 MLS

HIGH-EXPOSURE RESIDENTIAL / COMMERCIAL CORNER – OSTEEN GROWTH CORRIDOR Strategically positioned 1.09-acre corner lot with triple road frontage, including SR 415, delivering maximum visibility, accessibility, and long-term upside. Located in the core of Osteen, next to the Osteen Trailhead and directly in the path of growth, part of the future Osteen Commercial Village, this site is primed for commercial expansion and increasing demand. Flexible zoning supports multiple income-producing uses: retail, QSR/fast food, contractor operations, storage, and service businesses. Existing improvements add immediate value: • Main structure with solid bones ready for renovation or repurposing • Corner building with historic character, ideal for office, retail, or specialty use Ideal for investors, owner-users, or developers seeking a high-visibility site with redevelopment potential and future appreciation. Available for SALE or LEASE – strong opportunity to secure a key position in Osteen’s commercial expansion.

120 Railroad Avenue, Osteen

Listing courtesy of THE KEYES COMPANY. 386-428-5723

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Osteen - Osteen Florida Homes for Sale

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