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$800,000
403653 MLS
Experience the craftsmanship and character of a bygone era, all while enjoying modern comforts and convenience of this absolutely stunning brick office facility which offers a unique blend of timeless charm and modern amenities. Originally built in the early 1900’s as the historic Greenville Elementary School, this property has just recently undergone extensive renovations, such as a new roof and updated plumbing, electrical, and HVAC systems. The beautifully restored original hardwood floors, large hallways with transom windows, and the expansive auditorium complete with stage and velvet curtains evoke a sense of grandeur rarely seen in today's buildings. Soaked in natural light from oversized windows, this property showcases a perfect balance of classic architectural details and functional, updated spaces. The layout offers versatility consisting of 4 large conference rooms and over 20 individual office spaces. Two separate kitchen areas and four handicap-accessible bathrooms provide convenience, while the overall design and scale of the building make it ideal for a variety of professional uses. Whether you're looking to invest or occupy, this iconic property presents endless possibilities, and opportunities like this don’t come around often.

1476 SW Main Street, Greenville
$799,500
385635 MLS
The Little Aucilla River Runs through it! This is truly a one of a kind property. With a mix of pasture, pines and hardwood hamocks and low lands, it is ideal for hunting as well as a small farming operation. The Little Aucilla River runs through the property offering unique recreational oportunities. There are two ponds as well as a number of established food plots. There are two mobile homes on the property that are offered strictly "As Is". The primary mobile home would make an ideal hunting lodge and has been customized with rustic charm.

3282 NW US 221 Highway, Greenville
$736,951
2 Beds ⋅ 1 Baths ⋅ 400557 MLS
Bring All Offers!!! Sportsman's Paradise Nature Preserve Quiet Country Living (2 Ponds) Bordering Plantation on 2 sides. "Out in the country past the city limit signs"..a diamond in the rough giving "Little House on the Prairie" vibes could easily be manicured and restored to perfection. Plenty of potential with almost 30 acres. Two ponds seem to be spring fed full of water, fantastic recreational spot in rural Jefferson county Florida. Bring the horses. Plenty of room for pasture and with walking trails across the way through the dirt road development of Aucilla shores you could ride for days. Even fly into the Jefferson landing strip. The old church was moved out there and restored to a comfortable 2 Bed cottage. With pecky Cypress interior walls and a nice slate wood fireplace to keep it warm. Would need a full restoration but plenty of good bones. Deep Well and Septic are "as is" condition with right to inspect. Convenient North Florida location with easy access to Valdosta GA, Thomasville GA, Monticello FL and Tallahassee FL, and their respective medical services.

10481 ashville Highway, Greenville
$469,000
4 Beds ⋅ 2 Baths ⋅ 397009 MLS
Nestled in the peaceful Ashville Highlands fly-in community, this custom 2600+ sq. ft. all-brick home offers space, privacy and quality construction 15 min east of Monticello. Assumable VA loan available @ 2.5% for qualified veterans and non-veterans. Built with insulated concrete form walls and a metal roof, the home is designed for durability and comfort. The five acre property includes a 24x24 metal outbuilding/garage, generator, 50 amp RV plug-in and parking, and cross fencing for animals or gardens. An expansive screened porch opens to a tranquil Koi pond and cascading waterfall. Enjoy the serenity of the North Florida countryside with no HOA. Some photos are virtually staged to showcase potential use of space.

1142 Ashville Highlands Drive, Greenville
$385,000
4 Beds ⋅ 2 Baths ⋅ 404273 MLS
Country living with room to roam! Situated on approximately 26 acres just minutes from the Georgia line, this well-maintained 2022, 4-bedroom, 2-bath home offers 1,512 square feet and a spacious open-concept floor plan. The large kitchen is the heart of the home, featuring abundant cabinetry, a center island with seating, gas range and plenty of workspace, all opening seamlessly to the dining and living areas. The primary suite offers a private bath, while three additional bedrooms provide plenty of flexibility for family, guests, a home office or hobby space. Sliding glass doors off the dining area lead to the rear deck and make it easy to enjoy the peaceful country setting. Outside is where this property really shines. Surrounded by large tracts of land, the acreage offers a beautiful combination of mature woods, open and cleared areas, and established paths and driveways—creating an ideal setting for those looking for privacy, outdoor recreation or hunting opportunities. A large pole barn with power and water, separate metal outbuilding, additional covered structure and fire pit area provide plenty of space for equipment, tractors, ATVs, boats, RVs, hunting gear, hobbies and more. A gated entrance, concrete parking pad, patio and walkways add to the property's functionality, while the generous cleared homesite provides plenty of usable space around the residence. The property consists of two separate parcels, offering additional flexibility for the next owner. According to FEMA flood maps, the parcel containing the residence is not located within a designated flood zone, while portions of the additional acreage are within a designated flood zone. Buyer to verify. Whether you're searching for a full-time country home with acreage, family hunting property, or North Florida recreational retreat, this property offers an appealing combination of a newer home, privacy, usable land and substantial improvements already in place.

1897 NW Radford Denson Road, Greenville
$349,000
5 Beds ⋅ 2 Baths ⋅ 403868 MLS
Huge Price Reduction & Short Sale Potential! Dreaming of owning your own private farm with a large house AND Solar Powered? Look no further! Beautiful and serene 16 acres with fruit trees, fields, lots of horse potential and 40 solar panels about 5 years old. Nearly free electric! 5 Bedroom, 2 Bath with Large Eat-in Kitchen, Stainless Steel Appliances, Huge Great Room, Beautiful Hardwood Floors throughout main floor of the house, TWO Large Screened-in Porches over looking your private backyard. So many options with this property! Current set up for 3 RV parking spots with power, solar and septic tanks. Also 2 outside bathrooms. Small barn with chicken coop and stall. Pig pens on the back of the 6 acres. Enjoy seeing the plenty of wild game roam the property! You really can't miss this unique property!

10283 Ashville Highway, Greenville
$349,000
3 Beds ⋅ 1 Baths ⋅ 395498 MLS
Back On Market! Just in time for hunting season! Tucked away at the end of a privately maintained dirt road, this hidden North Florida retreat offers the kind of peace that's becoming harder to find. Whether you are searching for a hunting camp, weekend getaway, homestead or full time escape from the demands of city life, this property lives large with 40 acres of wildlife, birds, flora, fauna and unexplored woodlands and nooks. Located between Valdosta, Georgia and the Gulf of America is this extremely rural, 2 story 3 Bdrm, 2 Bth, downstairs needs paint and floor covering or if this place is going to be a hunting lodge for the boys...just leave it as it is and bring the bunk beds, the cow hide rugs, deer heads and let it rip! Bring the bulldozer! This land is very thick, you will need side by sides, buggies, ATV's and other fun toys to come look and enjoy. No HOA, No Restrictions! Outdoorsman's paradise! Room measurements are approximate. Furniture and TV included in the sale.

777 SW Wacissa Terrace, Greenville
$339,000
398952 MLS
Located within the gated and highly sought-after Aucilla Plantation, this 41-acre property offers the kind of setup serious outdoorsmen are always searching for but rarely find ready to go. Tucked away for privacy, this tract is well known for its strong deer and turkey presence, with two established stand and feeder locations already in place. The land itself is thoughtfully laid out with a solid trail system for easy access throughout the property, a small dug pond that adds both function and wildlife appeal, and a large cleared yard area that creates a central hub for gatherings and day-to-day use. At the heart of the property sits a fully finished metal building designed for comfort, functionality, and hosting. The structure is framed in and insulated, featuring a full bathroom, kitchen, and sleeping accommodations for up to 12. Whether you're using it for hunting season or extended stays, the setup is built to handle a crowd with ease. Multiple large bay doors provide excellent access for equipment, ATVs, and gear, while a dedicated back storage and laundry room adds convenience for longer stays. The layout is practical, clean, and built with the lifestyle in mind. This is a turn-key hunting camp with the privacy of a gated community, quality improvements already in place, and the kind of land that keeps wildlife moving. Properties like this don’t come around often in Aucilla Plantation.

1193 SW Oregon Trail, Greenville
$315,000
5 Beds ⋅ 3 Baths ⋅ 395759 MLS
Property is being sold with 4 acres.

7638 Sundown Creek Road, Greenville
$299,000
398840 MLS
Set on an expansive 75 acres of pristine land, this exceptional parcel is a hunter’s dream and an outdoor enthusiast’s private retreat. Thoughtfully developed with a network of well-maintained trails, the property offers easy access throughout, whether you’re navigating by ATV, hiking, or scouting game. Strategically placed hunting stands are already in position, providing optimal vantage points across diverse terrain and natural wildlife corridors. The landscape offers a balanced mix of wooded areas and open spaces, creating ideal conditions for attracting and sustaining game. Whether you’re looking for a turnkey hunting property, a recreational getaway, or a long-term land investment, this tract delivers both functionality and natural beauty. With ample space, privacy, and infrastructure already in place, it’s ready for immediate use and endless possibilities.

0000 Madison Main Line Road, Greenville
$275,000
3 Beds ⋅ 2 Baths ⋅ 402654 MLS
Looking for peaceful country living with room to spread out? This spacious 3-bedroom, 2-bath home sits on 2.75 beautiful acres, offering over 2,000 square feet of comfortable living space. The thoughtful split-bedroom floor plan features a large living room, formal dining room, eat-in kitchen, dedicated office/flex space, and generous walk-in closets in every bedroom. The private primary suite includes a double vanity, garden tub, separate shower, and water closet. Outside, enjoy the open yard with plenty of space for gardening, recreation, or simply relaxing in the quiet surroundings. If you've been searching for acreage and a home with endless potential, this property is ready for you to make it your own.

6801 NW Lovett Road, Greenville
$269,000
4 Beds ⋅ 2 Baths ⋅ 402808 MLS
Curb appeal meets country charm. Step into a piece of North Florida history with this 1915 home in Greenville, FL. Situated on a spacious 0.75 acre corner lot, this 4 bedroom, 2 bath home offers over 3000 square feet of living space and original hardwood floors throughout. Home has been in a full renovation status since 2022. Major improvements include replaced electrical and plumbing systems, 2018 complete roof replacement, spacious living and dining rooms, a striking octagon addition with multiple French doors offering a spectacular sanctuary. Exterior standouts includes, 1,460 square feet of covered wraparound porches and a 560-square-foot composite back deck. Additional features include a 22x32 oversized garage, cleared and leveled grounds, citrus trees, reinforced 2x6 construction, hurricane straps and added structural supports. An excellent opportunity for an investor or fixer-upper enthusiast, this unique property also offers potential as a bed-and-breakfast, intimate event venue, room-rental property or multigenerational residence, subject to local zoning and approvals.

1534 SW Main Street, Greenville
$265,000
3 Beds ⋅ 2 Baths ⋅ 404951 MLS
Welcome home! This charming 3-bedroom, 2-bath home offers a bright and inviting open floor plan, providing plenty of space for comfortable everyday living and entertaining. The spacious family room is centered around a beautiful stone fireplace, creating a warm and inviting gathering space. The kitchen is both functional and charming, featuring stainless steel appliances, skylights, a large island, and ample workspace. The primary suite offers a walk-in closet and an updated walk-in tile shower, while the oversized laundry and utility room provides even more convenient functional space. Step outside and enjoy everything this beautiful property has to offer. Relax on the covered back deck, take in the peaceful surroundings, watch the sunset, and keep an eye out for deer wandering through the property. With 5 private acres and gorgeous mature oaks providing shade and character, this is a place where you can truly slow down and enjoy the peace and quiet of rural living. And while the setting feels wonderfully private and secluded, you're still close to town and all the amenities you need. Located just 11 miles from Monticello, FL, you'll have easy access to everyday essentials, along with Monticello's adorable downtown area featuring local shopping and restaurants. You're also approximately 38 miles from Tallahassee and 34 miles from Thomasville, GA, making trips to larger cities and additional shopping, dining, and services​​‌​​​​‌​‌​​​​‌‌​​‌‌​‌‌​​‌​​​‌​‌ convenient.

1120 deerwood, Greenville
$235,000
389069 MLS
Lot 121 40.49 Acres in Gated Aucilla Plantation Greenville, FL Lot 115 is also available! Discover the perfect blend of seclusion, recreation, and investment potential with this beautiful 40.49-acre parcel located in Aucilla Plantation, a private, gated subdivision in Greenville, FL. This exclusive, monitored community spans over 3,000 acres and offers miles of private roads ideal for horseback riding, outdoor exploration, and peaceful country living. Hunting is permitted, making this an ideal retreat for outdoor enthusiasts or those looking to build a homestead surrounded by nature. Community Highlights: Minimum 1,400 sq ft site-built homes required (no mobile homes) Horses allowed (1 per acre) No swine, poultry, or livestock Power is available throughout the subdivision HOA dues are $425/year This property is part of a gated, live-monitored community, and an agent must be present to show. Buyer should verify lot dimensions. Don't miss this opportunity to own a premium lot in one of North Floridas most beautiful rural communities.

Lot 121 SW Pacific Drive, Greenville
$220,000
5 Beds ⋅ 3 Baths ⋅ 404908 MLS
PRICED TO SELL — HOME NEEDS A COMPLETE ELECTRICAL REWIRE. The list price reflects the electrical work needed, creating an opportunity to purchase nearly 3,400 square feet with five bedrooms, three bathrooms, an inground pool, and a highly versatile floor plan. Situated on approximately one acre, this spacious two-story home offers plenty of room inside with multiple living and gathering areas. The main level features a formal living room, large family room with a wood-burning fireplace, separate dining room, and a bright sunroom overlooking the pool. The kitchen offers abundant cabinetry and counter space, a breakfast bar, and a casual breakfast area. A guest bedroom and full bathroom are conveniently located downstairs, making the layout well suited for visitors, extended family, or multi-generational living. Upstairs, the private primary suite is tucked away from the main living areas, along with additional bedrooms offering flexibility for family, office, or hobby space. Outside, the inground swimming pool takes center stage, complemented by a patio and several covered areas that make it easy to enjoy the outdoors. Two covered porches and two covered patios provide additional spots for relaxing, entertaining, or gathering around the pool. Additional features include covered carport parking, a large laundry room with extensive storage, and an abundance of living space throughout. With five bedrooms, three bathrooms, nearly 3,400 square feet, and a private inground pool, this home offers tremendous potential at a price that takes the needed electrical rewire into consideration. Bring your vision and make this spacious property your own.

538 NW US Highway 221, Greenville
$220,000
402933 MLS
Formerly a bank in Greenville, Florida with ballistic proof glass and a large "walk in" bank vault included, built in 1980 and is a well maintained brick structure. The land and building is on the corner of Haffye Drive and US 90 West. With concrete driveway that loops around and through to a covered "drive through" with transaction drawer or sliding tray box. Two inside bathrooms and a kitchenette. Parking lanes with stripes plus handicap space already clearly painted and identified. Lots of security lighting on all four sides. Flag pole. New Roof in Feb of 2022. Functioning HVAC that works great. City water and city sewer. Lot size is 185x200 which calculates out to 37,000 sq. ft. which leaves plenty of room for expansion or additional use of the land which is all high, dry and well drained. Signage visibility for 1/4 mile in both directions. Located between Monticello, Florida and Madison, Florida. Quitman, Georgia is 23.9 miles. Interstate 10 Exit #241 is 3 miles away. Ready for quick closing.

13796 W US 90, Greenville
$215,000
389068 MLS
Lot 115 - 49.54 Acres in Gated Aucilla Plantation - Greenville, FL Lot 121 is also available in Aucilla Plantation just down the road! Discover the perfect blend of seclusion, recreation, and investment potential with this beautiful 49.54-acre parcel located in Aucilla Plantation, a private, gated subdivision in Greenville, FL. This exclusive, monitored community spans over 3,000 acres and offers miles of private roads ideal for horseback riding, outdoor exploration, and peaceful country living. Hunting is permitted, making this an ideal retreat for outdoor enthusiasts or those looking to build a homestead surrounded by nature. Community Highlights: Minimum 1,400 sq ft site-built homes required (no mobile homes). Horses allowed (1 per acre). No swine, poultry, or livestock. Power is available throughout the subdivision. HOA dues are $425/year. This property is part of a gated, live-monitored community, and an agent must be present to show. Buyer should verify lot dimensions. Lots 121 is also available and can be purchased separately or as a package. Don't miss this opportunity to own a premium lot in one of North Florida's most beautiful and scenic rural communities.

Lot 115 SW Pier Road, Greenville
$186,000
368051 MLS
This outstanding 46-acre tract has endless possibilities. Build your dream home, harvest deer, turkey and other small game or make it a calming retreat. The tract of land is located just a short drive from I-10 which allows easy access to the main highway yet tucked away from all the noise from the bigger cities. The property has a mix of pines and hardwoods that allow for different natural habitats as well as paved road frontage. Come and view this property and do not miss this opportunity!

2894 SW Overstreet Avenue, Greenville
$179,500
380673 MLS
Wow...take a look at this! Over 40 acres of natural paradise. This gem is located within the private, gated subdivision of Aucilla Plantation in Madison County, North Florida. The Plantation has over 3,000 acres of gated and monitored property with several miles of private roads to enjoy. You'll fall in love with it the minute you drive through the wrought iron gates! This property boasts several food plots, mowed trails throughout and wildlife galore! Acreage has several high and dry locations to build your custom home(approx 3-4 acres not in the flood zone), make a vacation/hunting retreat or use as an investment. It also has several acres of planted pines which allows you keep it under greenbelt(agricultural exemption) classification; keeps taxes really low and produces future income. Don't miss out on this one! No swine, livestock or poultry but horses are welcome (1 per acre). Hunting allowed. Minimum 1400 sq ft site built homes-no MH allowed. HOA fee is $425/yr. Lot dimensions are approx. and should be verified by buyer. Power runs through the subdivision. AGENT MUST BE PRESENT TO SHOW.

Lot 116 SW Pier Road, Greenville
$155,500
401537 MLS
15.5 Ac. 8-10 year old planted pines. Was previously strawed and could be again. Property is high and dry and has a good roll. Would be ideal for homesite

0000 NW US 221 N Highway, Greenville
$149,999
399158 MLS
Discover your own slice of North Florida paradise with this beautiful 40-acre tract located in the desirable Aucilla Plantation. This raw land offers endless potential for a private homestead, recreational getaway, or prime hunting property. Surrounded by natural beauty and abundant wildlife including deer, turkey, and more, it’s an ideal setting for outdoor enthusiasts. Enjoy peace, privacy, and plenty of space to build your dream home or weekend retreat while still benefiting from the community setting of Aucilla Plantation. Rare opportunity to own a versatile tract in a sought-after area!

Lot 84 SW Oregon Trail, Greenville
$149,000
390849 MLS
Seller Motivated to Sell! Discover 14.9 acres of pristine residential/recreational land along the Upper Aucilla River, near Sneads Lake in Jefferson County, Florida. This unique property offers a rare combination of upland and waterfront ownership with a portion of the property submerged by the flowing river. "Own out into & beyond the river channel (all the way to other bank) on the "Aucilla River". Outdoor enthusiasts will be in paradise—duck hunters will find world-class opportunities, deer are plentiful for stocking the freezer, and wild turkeys are abundant enough to fill your Thanksgiving table and beyond. The land is partially cleared with select hardwoods and native cypress groves remaining, providing both open areas and natural cover. The property is ready for your new construction or your manufactured home with no architectural requirements or timelines. Currently the river is in a natural draw down cycle where the river self manages cleaning out old growth and making way for fresh flow when the waters return. Now is the time to build a board walk, dock or fishing platform while the water level is down. Whether you’re looking for a homesite, a private hunting retreat, a weekend getaway, or a rare investment opportunity with natural waterfront access, this property is a true North Florida treasure. No HOA. No dues. Located between Quitman Georgia, Monticello, Florida and the Gulf of America.

96 Sneads Drive, Greenville
$147,900
399914 MLS
40.55 Acres in Aucilla Plantation – Madison County, FL OWNER FINANCING AVAILABLE – 30% DOWN | 6.5% INTEREST | FLEXIBLE TERMS Located inside Aucilla Plantation, a deed-restricted community, this 40.55-acre tract offers the perfect blend of privacy, recreation, and future homesite potential. Gated entrances provide privacy and security Peaceful setting — escape the hustle and bustle and enjoy nature Excellent hunting opportunities with abundant deer, turkey, and hog Plenty of room to roam, relax, and enjoy the outdoors Ideal for a recreational retreat, weekend getaway, or future homesite Low $450/year association fee for road maintenance and community upkeep

Vacant SW Naples Terrace, Greenville
$147,000
401534 MLS
14.7 AC MOL. Property is planted in 8-10 year old pines. Was previously strawed and could be again with minimal clean up. There is an adjoining 15.5 acres available. Great Hwy frontage on threee sides of property.

000 NW US 221 Highway, Greenville
$144,000
405418 MLS
Escape to the quiet of Shady Grove with this 27.2 acre tract featuring a beautiful mix of planted pines and natural hardwood swamp. This versatile property offers multiple opportunities—whether you’re looking for a larger acreage homesite, a productive hunting property, or a long-term timber investment, this land checks all the boxes. Located on SW Wonderwood Street, the acreage provides a blend of open areas and wooded cover, making it ideal for both recreation and privacy. With four additional parcels of varying sizes available, buyers have the unique chance to expand and create the perfect property to fit their vision. Whether you’re seeking a weekend getaway, a rural homesite, or investment potential, this Shady Grove property offers the space and natural setting to make it happen.

Lot 2 SW Wonderwood Street, Greenville
$140,000
3 Beds ⋅ 2 Baths ⋅ 395920 MLS
Home is being offered As-Is, 3 Bedroom, 2 Bath Home, on 1.37 Acres located in the Town of Sirmans.

8955 SW US 221, Greenville
$125,000
404548 MLS
More than 14 cleared acres in Madison County, where Florida’s rolling hills begin. With power available at the road and the driveway already started, much of the groundwork is in place for whatever you have in mind. Build your dream home or bring a mobile home, then shape the property around the life you want to live. Picture horses grazing in the pasture, a barn with fenced paddocks, rows of vegetables, fruit trees, chickens, or a full homestead with room to grow. There is plenty of open space for a mini farm, workshop, garden, equipment, and outdoor living, all surrounded by peaceful countryside and wide open views. Located near Interstate 10, you can enjoy the space and quiet of country living while still having convenient access for commuting, shopping, and everyday needs.

Vacant SW Deland Loop, Greenville
$89,000
405417 MLS
Escape to the quiet of Shady Grove with this 19.4-acre tract featuring a beautiful mix of planted pines and natural hardwood swamp. This versatile property offers multiple opportunities—whether you’re looking for a larger acreage homesite, a productive hunting property, or a long-term timber investment, this land checks all the boxes. Located on SW Wonderwood Street, the acreage provides a blend of open areas and wooded cover, making it ideal for both recreation and privacy. With four additional parcels of varying sizes available, buyers have the unique chance to expand and create the perfect property to fit their vision. Whether you’re seeking a weekend getaway, a rural homesite, or investment potential, this Shady Grove property offers the space and natural setting to make it happen.

Lot 3 SW Wonderwood Street, Greenville
$89,000
403775 MLS
Opportunity awaits! Situated directly along US Highway 19, this commercial property offers excellent road frontage and visibility with plenty of potential for its next owner. The building features a spacious open interior, rustic wood finishes, a service/counter area, and a large covered front entrance that adds character and functionality. With ample outdoor space and convenient highway access, the property provides a versatile canvas for a variety of business or investment possibilities. Whether you're looking to renovate for retail, office, service, community, or another commercial concept, this property offers the opportunity to bring your vision to life. Property is being sold AS-IS. Buyer to verify zoning, permitted uses, building condition, utilities, measurements, and all information deemed important to intended use.

13125 N Us 19 Street, Greenville
$80,500
397943 MLS
This natual beauty of 5 acres with house and shed is priced for land value. The delapidated structures holds little to no value. With ownership afar, the property has been untouched for years. Hinting at what once was and what could be again, this property invites a lifestyle of peace and seclusion giving you a unique opportunity to create your own sanctuary complete with a pond that mirrors the surrounding land and open skies. Whether you envision luxury estate ,farmhouse or a private getaway the canvas is yours to create. Structures are delapidated unsafe please view from outside.

455 E DUCKPOND DR Drive, Greenville