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$990,000
4 Beds ⋅ 3 Baths ⋅ Cypress Isles SubDv. ⋅ 32764 Zip Code
Set on 10 ACRES in Osteen, this unique property combines a spacious residence, an ATTACHED 1-BEDROOM APARTMENT, extensive agricultural improvements, and plenty of room to enjoy acreage living. The main home offers 3 bedrooms, 2 bathrooms, 10-foot ceilings, a fireplace, an open kitchen with reverse osmosis, a gas range installed in 2025, and a large pantry/laundry area. The primary suite features a spacious three-head walk-in shower and direct access to the EXPANSIVE SCREENED PORCH overlooking the property. The attached apartment includes 1 bedroom, 1 bathroom, a full kitchen, walk-in closet, tub/shower, and separate entrance, providing flexible additional living space. Outside, the property is FENCED AND CROSS-FENCED and includes THREE PONDS STOCKED WITH CATFISH AND TILAPIA, a detached 3-car garage with attic storage, a whole-home propane generator installed in 2025, a utility barn with power and water, fenced garden area with raised beds, multiple livestock pens and coops, cattle chute and corral, feeders, and water troughs throughout the fields. Mature bamboo, large live oaks, and an extensive variety of fruit trees and plants add privacy and character across the acreage. Additional features include a 16-foot swim spa with deck, 190-yard shooting range, covered front porch, exterior paint completed in 2024, and fresh interior paint in 2026. The property also offers CONVENIENT ACCESS TO THE RIVER-TO-SEA LOOP BIKE TRAIL along Osteen Maytown Road, adding another way to enjoy the surrounding outdoor lifestyle. The Cypress Isles community has a private St. Johns Riverfront Park with a boat ramp, playground and pavilion. The HOA fee also goes to cover the maintenance of the community roads. Call to schedule your private showing today!

615 Deer Pond Road, Osteen
$750,000
4 Beds ⋅ 3 Baths ⋅ Cove At Lemon Bluff Unrec SubDv. ⋅ 32764 Zip Code
Experience refined country living with convenient access to major commuter routes. Situated on 10.32 acres with a private pond, this four-bedroom, three-bath log cabin offers a distinctive combination of space, privacy, and accessibility. The main level features a spacious living area with high ceilings and a wood-burning fireplace. At the rear of the home, two bedrooms, a full bathroom, and a versatile nook provide direct access to an expansive screened porch. The kitchen adjoins the dining room and connects to a generously sized interior mudroom and laundry area. The upper level includes the primary bedroom, an additional bedroom, a full bathroom, and a great room overlooking the main living space. Recent improvements include exterior painting and resealing, new exterior doors and windows, and 2024 upgrades to the air-conditioning system and water heater. A durable metal roof provides additional long-term value. With agricultural zoning and no homeowners association, the property offers considerable flexibility and privacy. Convenient access to SR 415, SR 417, and I-4 supports efficient travel to Sanford, Orlando, and destinations farther south. A nearby boat ramp provides access to the St. Johns River, Lake Monroe, Lake Jesup, Puzzle Lake, and surrounding waterways, making this an exceptional property for those who value outdoor recreation.

698 Wild Acres Road, Osteen
$675,000
3 Beds ⋅ 2 Baths ⋅ Cypress Isles SubDv. ⋅ 32764 Zip Code
Virtually Staged. Location Location Location! Private, yet close to everything for those seeking quiet country living with modern comforts. Minutes from local walking, hiking and horse trails. LOW HOA and Key access to St. Johns Community Park. Come see this Charming 3 bedroom 2 bath Country home, situated on 10 Acres of pristine land! Large private pond stocked with brim, catfish and tilapia. On the land, you will find a huge barn/workshop, 2 pole barns for your boats, RV’s and other recreational vehicle's. All fully equipped with electricity. Whole house, 500 LB generator with propane tank underground, installed 2022. Roof replaced in 2022, HVAC system replaced in 2023. Water filtration system installed in 2026. The interior boasts of, vaulted ceilings with an open concept floor plan. Creating a natural flow for everyday living and entertaining. The kitchen offers stainless Steele appliances with solid wood cabinetry. Refrigerator replaced 2026 along with new laminate flooring through out, replaced in 2025. Master bath remodeled in 2022. As a bonus, this home also offers a safe room for Florida’s seasonal changes. Enjoy morning sunrise and sunsets from the front/back porch areas. Easy access to SR 415, just minutes to airports, hospitals, beaches, restaurants and shopping. Call today, to schedule a private showing.

806 Bayhead Road, Osteen
$750,000
4 Beds ⋅ 4 Baths ⋅ N/A SubDv. ⋅ 32764 Zip Code
Exceptional 5+ acre property located just off SR-415 with excellent access and strong potential for agricultural, residential, or business use. The ranch-style home features a downstairs primary suite, two stone fireplaces, laminate flooring, an open-concept living and kitchen area, an upstairs overlook to the dining space, a downstairs office, an oversized laundry room, and both front and back porches with peaceful pond views. Recent upgrades include a NEW A/C system and a NEW water heater, offering added efficiency and peace of mind. The property includes two barns: a 2,292 sq ft barn with insulated flooring, concrete slab, and walk-in cooler, plus a 950 sq ft barn ideal for storage or workspace. Additional features include 2 RV pads with their own septic system, well water, two A/C units, and a rear pond with trails leading into a wooded area. Excellent opportunity for a home-based business, agricultural use, or potential barn-style event venue, conveniently located near Orlando, Daytona, New Smyrna, and Jacksonville

445 S State Road 415, Osteen
$799,900
4 Beds ⋅ 3 Baths ⋅ Osteen SubDv. ⋅ 32764 Zip Code
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
$690,000
3 Beds ⋅ 3 Baths ⋅ Acreage SubDv. ⋅ 32764 Zip Code
Escape to Your Private Almost 5-Acre Country Retreat Discover the perfect balance of serenity and convenience in this beautifully updated country home. Nestled on nearly five acres of lush, wooded land, this spacious residence offers a peaceful sanctuary away from the hustle and bustle without sacrificing proximity to shopping and local amenities. The interior features large, light-filled rooms with high-end finishes and a cozy fireplace, making the home entirely move-in ready. Step outside to the screened-in porch—the ideal spot for morning coffee while watching local wildlife, including deer and birds, roam through the trees. Practicality meets curb appeal with a recently added asphalt circular driveway (no dirt roads here!) and additional storage space in the rear. Located steps from local walking trails, this property is a rare find for those seeking quiet country living with modern comforts.

1395 Maytown Road, Osteen
$669,900
3 Beds ⋅ 2 Baths ⋅ Cypress Isles SubDv. ⋅ 32764 Zip Code
Bring the horses, chickens, boats, and toys—this fully fenced 13.30-acre Osteen property is ready for it all. This move-in-ready 3-bedroom, 2-bath home features granite countertops, wood cabinetry, tile flooring throughout, fresh interior paint, updated fixtures, and a new roof (2024). Designed for equestrian living, the property includes 3 paddocks, a 3-stall barn with oversized 16x12 stalls and private runs, water and electric service, covered equipment storage, a tack/feed room, and a built-in chicken coop. Recent upgrades also include a new water softener, chlorinator, filtration system, and updated landscaping. Enjoy peaceful views from the oversized screened lanai and take advantage of direct access to nearby riding trails, including Hickory Bluff and Palm Bluff. Residents also enjoy access to a private St. Johns River boat launch, pavilion, and playground. Rarely does a property provide this combination of acreage, horse facilities, modern updates, trail access, and river community amenities—all in one turnkey package.

430 Cypress Isles Road, Osteen
$800,000
4 Beds ⋅ 3 Baths ⋅ Cambridge Villas SubDv. ⋅ 32764 Zip Code
Set on over 4 fully usable acres in Osteen, this custom-built estate offers a rare combination of privacy, space, and long-term potential that’s nearly impossible to replicate today. This 4-bedroom, 3-bathroom home spans over 3,100 square feet of living space, designed with functionality and scale in mind. From the moment you pull in, you feel the separation—no tight subdivisions, no HOA, just open land and the ability to live the way you want. Inside, the layout delivers both comfort and practicality. A spacious kitchen with solid wood cabinetry and an island opens into the main living areas, creating a natural flow for everyday living and entertaining. The primary suite is positioned upstairs with generous proportions, dual sinks, and separation from guest bedrooms—ideal for families or multi-generational living. Step outside and this is where the property really takes over. A true resort-style pool With Waterfalls anchors the backyard, complete with a jacuzzi—built for year-round use whether you’re hosting, unwinding after a long day, or spending weekends at home. This setup feels intentional and designed for the lifestyle, not added as an afterthought. Surrounding the home is over 4 acres of private, buildable land—giving you the flexibility most buyers are searching for right now. Add a guest house, detached garage, barn, or workshop. Create a full family compound. Bring animals. Park your equipment. Or keep it simple and enjoy the space, the quiet, and the freedom. There’s already a private trail running through the property—perfect for riding, walking, or letting the dogs run without ever worrying about traffic or neighbors. This is the kind of land where you can actually use every inch. The wrap-around porch ties it all together, giving you a place to slow down and take in what you own—something that’s becoming harder to find in Central Florida. From a structural standpoint, the home is built to last with block construction, a durable metal roof, well and septic, and no HOA restrictions—giving you full control over how the property evolves over time. Location-wise, you’re positioned for both privacy and accessibility—just a short drive to shopping, dining, and major roadways, while still feeling completely removed from the noise. Nearby natural areas and trails only add to the lifestyle this property offers. Properties like this aren’t just homes—they’re long-term holds. With limited inventory offering acreage, a pool, jacuzzi, and buildable land together, opportunities like this don’t come around often. If you’re looking for space, privacy, and the ability to create something beyond a standard home—this is where it starts.

326 Enterprise Osteen Road, Osteen
$525,000
3 Beds ⋅ 2 Baths ⋅ Westside SubDv. ⋅ 32764 Zip Code
Virtually Staged. Price reduction! This exceptional, custom-built home stands in a class of its own. The property features brand-new textured ceilings and walls, complemented by fresh paint throughout. The upgraded kitchen is a chef's delight, boasting all-wood, soft-close cabinetry, two lazy Susans, a deep sink, premium stone countertops, an expansive pantry, and modern recessed lighting. A convenient snack bar adjacent to the dining room leads through sliding glass doors to a covered patio, perfect for grilling and outdoor relaxation. The upstairs primary suite includes private balcony access, offering scenic views of the expansive backyard and mature oak trees. The home’s interior is highlighted by a stunning stone fireplace, making this two-story residence a true standout. Situated on approximately 2.5 acres, this property offers significant potential with its partially cleared landscape. Additional features include city water, a septic system, a metal roof installed in December 2025, an RV pad with hookups, and a newly installed driveway. This property is zoned for horses and livestock, with ample space for trucks and equipment. Huge Oversized Garage with ample room for toys and tools! A survey is available in the office; this unique property is a must-see.

2598 Enterprise Osteen Road, Osteen
$1,111,000
3 Beds ⋅ 3 Baths ⋅ Osteen SubDv. ⋅ 32764 Zip Code
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