Osteen Real Estate

Welcome to Osteen, Florida – a hidden gem nestled in the heart of Volusia County. This charming community offers a perfect blend of rural tranquility and convenient access to urban amenities, making it an ideal destination for families, retirees, and anyone seeking a peaceful lifestyle.

Osteen is characterized by its picturesque landscapes, featuring lush greenery, serene lakes, and scenic trails that invite outdoor enthusiasts to explore the natural beauty of the area. Residents enjoy a slower pace of life, with plenty of opportunities for fishing, hiking, and birdwatching. The nearby St. Johns River provides a perfect backdrop for water activities, while local parks offer playgrounds and picnic areas for family gatherings.

Despite its tranquil setting, Osteen is just a short drive away from larger cities like Deltona and Sanford, where you can find shopping, dining, and entertainment options. The community is well-connected, with easy access to major highways that lead to the bustling attractions of Orlando and the beautiful beaches of the Atlantic coast.

Education is a priority in Osteen, with several highly-rated schools in the area, ensuring that families have access to quality education for their children. The friendly atmosphere and sense of community make it easy to connect with neighbors and create lasting friendships.

Whether you’re looking for a cozy family home or a sprawling estate, Osteen offers a variety of real estate options to suit your needs. Discover the charm of Osteen, where a peaceful lifestyle meets vibrant community living in sunny Florida!

Newest Listings in Osteen

$450,000

263742 MLS

Opportunities like this simply do not happen anymore this close to the heart of the Nation's Oldest City. Welcome to 2 Helen Street, a premium, oversized 0.720-acre waterfront canvas perched directly on the picturesque San Sebastian River with No HOA or CDD fees. Imagine waking up to sweeping, uninterrupted water views and watching local wildlife thrive right in your backyard. From blue herons and egrets wading gracefully through the river marsh. This property offers a front-row seat to Florida's peaceful coastal ecosystem. When you are ready for a change of pace, grab your beach cruiser for a quick, scenic 7-minute bike ride into historic downtown St. Augustine to enjoy world-class dining, eclectic shopping, and iconic historic sites. You truly get the ultimate Florida lifestyle: a private, nature-filled escape and absolute city convenience. There is an uninhabitable structure on the property that holds no value, and the property is being sold ''as-is, land value only.

2 Helen St, St Augustine

Courtesy of Coldwell Banker Premier Properties (Historic Office)

$285,000

FC320762 MLS

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

Modern construction, over half an acre, no HOA, and quality upgrades you don't often find in newer homes—welcome to this beautifully maintained 2022-built home in Osteen. Offering 4 bedrooms, 2.5 baths, and 2,118 square feet, this home was thoughtfully designed for comfortable everyday living and effortless entertaining. At the center of it all is a beautifully appointed kitchen featuring quartz countertops, stainless steel appliances, a large center island, pantry, and abundant cabinetry, all open to the dining and living areas. The split-bedroom floor plan provides privacy for the spacious primary suite, complete with a beautifully finished ensuite bath and a custom walk-in closet with built-in organization. Step outside and discover one of the home's standout features. The covered lanai is equipped with a remote-controlled retractable screen, making it easy to enjoy Florida evenings in comfort, while the custom pergola creates the perfect setting for grilling, gathering with friends, or enjoying your morning coffee. The fully fenced 0.51-acre backyard also features mature citrus trees and a powered storage shed with double doors, providing plenty of room for a riding mower, tools, and outdoor equipment. Beyond its beautiful finishes, this home is packed with upgrades designed for comfort, efficiency, and peace of mind. Andersen Low-E windows help improve energy efficiency and natural light, the spray foam insulated garage helps regulate temperatures year-round, and the Generac whole-house generator (installed in 2025) provides added confidence during Florida storm season. The home is also equipped with a water softener and an Essency high-capacity water heater, a premium system designed for exceptional efficiency and a long service life—often exceeding 25 years with proper maintenance. A spacious laundry room with quartz countertops, upper cabinetry, and a utility sink adds even more everyday convenience. If you're looking for a newer home that offers quality construction, meaningful upgrades, and the freedom of country living without sacrificing modern comforts, this Osteen property is ready to welcome you home.

125 Longwood Drive, Osteen

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

$450,000

2154818 MLS

2 Helen Street, St. Augustine

Courtesy of COLDWELL BANKER PREMIER PROPERTIES

Listing courtesy of COLDWELL BANKER PREMIER PROPERTIES.

Listing courtesy of EILEEN F STRANGE from COLDWELL BANKER PREMIER PROPERTIES.

$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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