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$990,000
4 Beds ⋅ 3 Baths ⋅ V4951177 MLS
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 ⋅ V4951263 MLS
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
$400,000
4 Beds ⋅ 2 Baths ⋅ O6437347 MLS
If you've dreamed of owning acreage along a winding dirt road with a peaceful country feel, this is the property for you! Situated on 10 beautiful acres, this spacious 4-bedroom, 2-bath home offers privacy, room to roam, and endless possibilities. The inviting split-bedroom floor plan is ideal for both everyday living and entertaining. The open kitchen flows seamlessly into the dining area and family room, creating a wonderful gathering space highlighted by a cozy wood-burning fireplace. The spacious primary suite features an en-suite bathroom with dual vanities, a garden tub, and a separate shower. Three additional bedrooms are located on the opposite side of the home, along with a full bathroom and convenient utility room. The home's roof is approximately 8 years old. Outside, the possibilities are truly endless. The expansive 10-acre property offers plenty of room for outdoor activities, recreation, gardening, animals, or simply enjoying the peaceful surroundings. Surrounded by nature and tranquility, this property is a nature lover's dream and provides a rare opportunity to enjoy the privacy and freedom that acreage offers. This property backs up to a nature preserve so you do not have any rear neighbors. Come experience the serenity, space, and country lifestyle this property has to offer. Schedule your private showing today!

680 Wild Acres Road, Osteen
$750,000
4 Beds ⋅ 4 Baths ⋅ O6435418 MLS
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
$162,000
2 Beds ⋅ 2 Baths ⋅ O6417703 MLS
WELCOME to 938 Blue Heron Blvd. Kove Estates a premier 55+ community in Osteen Fl. Updated Subfloors, New Flooring throughout, Freshly Painted interior, New Water Heater. Newer Windows, Large Kitchen with plenty of cabinet storage, Eat-in Breakfast space with built in Cabinets. Indoor Laundry Room/Office, Large Primary bedroom with walk-in Closet, Primary bathroom features dual vanity sinks, walk-in shower. new toilet. Secondary Bedroom with walk-in closet, tons of natural light. Secondary bathroom features new vanity and toilet. Large Screened in Porch with Storage room, Back covered patio providing lots of shade and plenty of privacy. Large Storage room (no power) for all your extra things. Kove Estate, a 55+ Co-Op community, friendly active environment offering resort-style living in a Gated Golf community. There is NO lot rent, as a share in the community conveys with the sale. LOW monthly HOA FEE. As a resident of The Kove Estate, you will enjoy free 9-hole golf, two pools (one heated), tennis courts, pickleball, community events, Clubhouse, Library, and Gated security. The community is conveniently located off SR415, minutes to Sanford, Deltona, New Smyrna Beach, close to shopping, dining, medical facilities, and attractions such as the Daytona International Speedway, the Kennedy Space Center, and the Orlando theme parks. This is a must see for anyone looking for a peaceful and convenient lifestyle. Water, Sewer and trash pickup is included in the LOW HOA. Call today to view!

938 Blue Heron Boulevard, Osteen
$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
$690,000
3 Beds ⋅ 3 Baths ⋅ O6411770 MLS
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
$800,000
4 Beds ⋅ 3 Baths ⋅ V4948058 MLS
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 ⋅ V4947250 MLS
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
$89,900
1 Beds ⋅ 1 Baths ⋅ O6365050 MLS
ATTENTION!! LOT and TRAILER can be SOLD Separately. Call for details. LAKEFRONT LIVING! RETIRE WITH CONFIDENCE!! Welcome to Kove Estate, a 55+ Co-Op community, a friendly active environment offering resort-style living in a gated Golf community. This lakefront 2023 Keystone Retreat features a Primary Bedroom with built in cabinets and nice size closet. Additional sleeping quarters (Loft) and storage upstairs perfect for overnight guest. 1 Full Bathroom with Walk in Shower and additional storage, a spacious Open Living Room, Dining room Kitchen area. Kitchen features, Gas Range, Microwave, Oven, nice size Refrigerator/Freezer and closet pantry. Living Room features a sleeper sofa, built in TV console with Electric Fireplace. Beautiful new Deck overlooking Little Lake. Wash/Dryer combination. Plenty of parking for your and your guest. As a resident of The Kove Estate, you will enjoy free 9-hole golf, two pools (one heated), tennis courts, pickleball, community events, Clubhouse, Library, and Gated security. The community is conveniently located off SR415, minutes to Sanford, Deltona, New Smyrna Beach, close to shopping, dining, medical facilities, and attractions such as the Daytona International Speedway, the Kennedy Space Center, and the Orlando theme parks. The Keystone unit itself can be financed call for details. This is a perfect spot for a peaceful and convenient lifestyle. Trash, Sewer and trash pickup is included in the LOW HOA. There is no lot rent, as a share in the community conveys with the sale. Call today to view!

57 Kove Boulevard, Osteen