Jefferson County FL Homes for Sale

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  /44

  $629,900

  • 3 Beds
  • 2.5 Baths
  • 3,214 Sq Ft

  150 N Ojibwa Rd, Monticello, FL 32344

  Tranquil 5.1 acre retreat nestled deep in a pecan grove just outside Monticello, Florida has it all. This recently remodeled 3BR/2BA home offers space, privacy and flexibility in a rural setting only 40 minutes from the heart of Tallahassee. Take advantage of everything Tallahassee offers while paying lower Jefferson County taxes. The pecan trees qualify for an agricultural land use status,

  Hettie Spooner Hill Spooner & Elliott Inc

  150 N Ojibwa Rd, Monticello, FL 32344
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• 

  

  

  /42

  $589,900

  • 4 Beds
  • 5 Baths
  • 3,862 Sq Ft

  3873 N Jefferson St, Monticello, FL 32344

  Back on market due to no fault of the seller or home. Stunning 4 Bedroom, 3.5 Bath Home on 9.73 Acres with Large Detached Garage plus Oversized Attached 2 Car Garage Located just north of this spacious 3,862 square foot home sits on 9.73 acres with a tranquil creek running through the rear of the property. The home is built on high and dry ground, and not located in a flood zone or HOA.

  Stephanie Dobson Southern Land & Homes

  3873 N Jefferson St, Monticello, FL 32344
• 

  

  

  /11

  $499,900 New Construction

  • 4 Beds
  • 3 Baths
  • 1,798 Sq Ft

  855 S Waukeenah St, Monticello, FL 32344

  Stunning New Construction home currently being built by Southern Construction. Centrally located in downtown Monticello, with mature landscaping, and plenty of room for the family. This 4 bed and 3 bath home will feature vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Some finishes have been selected by builder,

  Jared Parramore Coastwise Realty

  855 S Waukeenah St, Monticello, FL 32344
• 

  

  

  /41

  $455,995 New Construction

  • 3 Beds
  • 2 Baths
  • 1,806 Sq Ft

  47 Mire Ct, Monticello, FL 32344

  Amazing new construction 3 bedroom 2 bathroom by Nailed It Tallahassee LLC Come pick out all your finishes, home scheduled for completion August 2025. Luxurious master suite, Kitchen made of dreams, this is a must see! Preferred Lender offering 1% in closing costs! Photos of previous home come make this one your own!

  Amber McKinney Hamilton Realty Advisors LLC

  47 Mire Ct, Monticello, FL 32344
• 

  

  

  /23

  $325,000

  • 5 Beds
  • 2 Baths
  • 2,659 Sq Ft

  2664 W Washington Hwy, Monticello, FL 32344

  FULLY RENOVATED SPACIOUS HOUSE, 1.3 acres, on picturesque US 90 near Monticello. This move-in-ready home in good condition is a 1950’s era brick ranch-style home with new plumbing, new electric, fresh paint, new roof, and a whole home generator. The main living area is 2,659 sf with a unique two levels. 5 bedrooms and 2 baths with plenty of character, including the "Captain's Room" with built-in

  Heather Boyd FL-GA Realty & Auction

  2664 W Washington Hwy, Monticello, FL 32344
• 

  

  /25

  $85,000

  • Land
  • 5.01 Acres
  • $16,966 per Acre

  687 Smokehouse Farms Dr Unit na, Greenville, FL 32331

  Fly into your new neighborhood. Take the side by side(RUV) to your Florida mountain home. Get on the horses and explore. Owners have done a lot of homework on preparing to build their home including well installation and site prep. Driveway and home-site cleared. Horse/farmhouse friendly 5 Acres naturally wooded & secluded on the back road of smokehouse farms. Giant oaks and deer abundant, Across

  Starbuck Rissman Steve C. Walker Realty, LLC

  687 Smokehouse Farms Dr Unit na, Greenville, FL 32331
• 

  

  /9

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,290 Sq Ft

  1125 E Dogwood St, Monticello, FL 32344

  Must see this brand new home being built by Southern Construction in the downtown Monticello area. Home features 3 bed, 2 baths, granite countertops, upgraded trim package, vinyl plank flooring throughout, tile bathroom and laundry floors, and stainless appliance package. Pics are of previous build, buyer may have time to pick finishes pending time of contract. Home expected to be completed in

  Jared Parramore Coastwise Realty

  1125 E Dogwood St, Monticello, FL 32344
• 

  

  /43

  $259,900

  • 2 Beds
  • 2 Baths
  • 1,922 Sq Ft

  2029 Boston Hwy, Monticello, FL 32344

  Looking to downsize but not ready to give up your space and privacy? Welcome to 2029 Boston Hwy—the perfect blend of comfort, convenience, and country charm. This beautifully maintained home sits on a fully fenced 1-acre lot, offering plenty of room to breathe without the hassle of a large property. Inside, you’ll love the open layout, cozy fireplace, and spacious kitchen with island and

  Alex Nunez Twelve Points Real Estate, LLC

  2029 Boston Hwy, Monticello, FL 32344
• 

  

  /37

  $135,000

  • 3 Beds
  • 2 Baths
  • 1,376 Sq Ft

  1150 Old Lloyd Rd, Monticello, FL 32344

  This mobile home is a serene retreat on a spacious 1-acre lot, blending comfort and nature located between Tallahassee and Monticello Fl. With 3 bedrooms and 2 bathrooms, it offers ample space for relaxation and entertainment. The screened porch invites tranquility, allowing you to unwind surrounded by nature while the sunroom bathes your home in natural light. Theres an expansive back porch

  Alicia Radtke All Realty Services

  1150 Old Lloyd Rd, Monticello, FL 32344
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  /7

  $150,000

  • Land
  • 10 Acres
  • $15,000 per Acre

  576 Cox Rd, Monticello, FL 32344

  Discover a fantastic future homesite on a secluded 10-acre parcel in northern Jefferson County, Florida! Accessed via a 15-foot-wide easement off a private road, the property opens up to a beautiful, private clearing ideal for building your dream home. The land features a mix of large pines, hardwoods, and magnolias, creating a serene, natural setting. Key utilities are already in place or

  Gabriela Sacco All Realty Services

  576 Cox Rd, Monticello, FL 32344
• 

  

  /50

  $1,050,000

  • 5 Beds
  • 3 Baths
  • 3,656 Sq Ft

  240 Valley View Ct, Monticello, FL 32344

  Spanning four full lots and over 20 acres, this private country estate offers two homes and endless possibilities—whether for horses, hobby farming, entertaining, or simply enjoying the peace of rural living. The 2,621 sq. ft. main home features 3BR/2BA with a split floor plan, two living areas with propane fireplaces, an updated primary suite with walk-in closet and renovated bath, multiple

  Hettie Spooner Hill Spooner & Elliott Inc

  240 Valley View Ct, Monticello, FL 32344
• 

  

  /22

  $219,000

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft

  185 Mallard Ln, Monticello, FL 32344

  Newer 2020 mobile home on 1.95 acres. This simple but beautiful property backs up to a lake. Property is mostly wooded at the moment but if cleared would have a lovely view of the lake and the Monticello sunsets. Located in a quiet neighborhood in Lloyd Acres. Convenient access to Tallahassee and the quaint historical district of downtown Monticello with many boutiques for shopping and

  Jennifer Weeks J. D. Salley & Associates, Inc

  185 Mallard Ln, Monticello, FL 32344
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  /43

  $185,000

  • 4 Beds
  • 2 Baths
  • 2,128 Sq Ft

  77 E 6th Ct, Greenville, FL 32331

  Enjoy the freedom of country living with this 4 bedroom, 2 bathroom mobile home on 10 acres in Jefferson County. With 2,128 square feet of living space, there’s plenty of room for everyone to spread out. The property is located on the state’s largest private airstrip, measuring 6,000 feet long, with two taxiways on the western side of the acreage for direct access. There’s ample space to build

  Catherine Hope All Realty Services

  77 E 6th Ct, Greenville, FL 32331
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  /11

  $95,000

  • Land
  • 3 Acres
  • $31,667 per Acre

  1309 Cook Rd, Lamont, FL 32336

  Looking for a peaceful retreat or a smart investment opportunity? This 3 acre lot in Monticello, Florida, might be just what you need! The property comes with a mobile home (which can be renovated or replaced according to your vision), well, septic, electric already in place! Beautiful mature oak trees, pines, and more! There is already an established deer food plot with an abundance of fresh

  Alicia Radtke All Realty Services

  1309 Cook Rd, Lamont, FL 32336
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  /42

  $459,900

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft

  952 Turney Anderson Rd, Monticello, FL 32344

  Time travel back to 2021 Interest rates with this assumable loan for +/- $250k at 2.95% interest for qualified buyers. If any property has it all, this one does. Spacious house with huge kitchen and tons of storage, fire pit in the back yard for marshmallow roasts. Generac generator to run the whole property during power outages. A 400 mph rated hurricane vault located in the 1500 sgft

  Katherine Hansli Searcy The Naumann Group Real Estate

  952 Turney Anderson Rd, Monticello, FL 32344
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  /17

  $12,999

  • 3 Beds
  • 2 Baths

  3 S Back Ct, Monticello, FL 32344

  FALL INTO SAVINGS! 2 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 10/31/25! ACT FAST! *Restrictions Apply. Opportunity is knocking in this LASSO Community in Monticello, Florida! This 3 bed, 2 bath home is being sold AS-IS-a true handyman special with unlimited potential. With solid bones and a spacious layout, this property is the perfect blank canvas for: Investors looking for their

  Patty Davis Jefferson Pines

  3 S Back Ct, Monticello, FL 32344
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  /7

  $7,999

  • 3 Beds
  • 2 Baths

  3 N Back Ct, Monticello, FL 32344

  Opportunity is just around the corner! This 3 bedroom, 2 bathroom handyman special is available. This home is being sold AS-IS, making it the perfect fit for: Investors looking for their next profitable project Contractors ready for a starter property to transform Handy buyers who love the idea of customizing their own home With a spacious layout, a private yard shaded by mature trees, and the

  Patty Davis Jefferson Pines

  3 N Back Ct, Monticello, FL 32344
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  /36

  $195,000

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft

  418 Quail Ln, Monticello, FL 32344

  Enjoy this quaint, well kept 2/2 mobile home on 1.5 acres of usable land. This homestead is perfect for a small family, or retired couple who want to be in nature, without sacrificing community. Convenient to both I-10 and Monticello, this home has lots to offer. Spend hours on the screened porch watching the birds and wildlife, work in the large on-site shop, float in the above ground pool in

  Heather Boyd FL-GA Realty & Auction

  418 Quail Ln, Monticello, FL 32344
• 

  

  /14

  $65,000

  • Land
  • 5 Acres
  • $13,000 per Acre

  000 Ashville Highlands Dr, Greenville, FL 32331

  Step into the wild with this 5 acre lot located just 10 minutes from downtown Monticello! This tract holds beautiful mature live oaks, as well as hardwoods, and pines! Use this exceptional tract of land for hunting or build your forever home! Just 2 minutes from Sneads Smoke House which offers an abundance of fishing opportunities! The land is your oyster!!!!

  Alicia Radtke All Realty Services

  000 Ashville Highlands Dr, Greenville, FL 32331
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  /64

  $1,200,000

  • 8 Beds
  • 6.5 Baths
  • 5,560 Sq Ft

  237 Valley View Ct, Monticello, FL 32344

  Unbelievable opportunity in Valley View Estates! Situated on 15+ (10+5) high-and-dry acres along the Leon/Jefferson County line, this unique property features two full-sized homes, a barn with additional living space, a heated/cooled workshop, and a screened pool with lanai. The custom-built main residence (~4000sf) offers 12’ ceilings, 3 bedrooms with ensuite baths, 2 additional bedrooms/flex

  Kelly Vinson Keller Williams Town & Country

  237 Valley View Ct, Monticello, FL 32344
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  /48

  $369,000

  • 3 Beds
  • 2 Baths
  • 1,722 Sq Ft

  525 Devane Rd, Monticello, FL 32344

  2024 custom-built, single story home on 3 acres near Jefferson Country Club with no HOA. Features 3 bedrooms plus a flexible bonus room—perfect for an office, studio, or guest space. Open floor plan with great room, bar seating, stainless appliances, high-end countertops, and LVP flooring throughout. Primary bath offers both a soaking tub and low-entry shower for accessibility. Storage

  Victoria Wilde Xcellence Realty

  525 Devane Rd, Monticello, FL 32344
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  /61

  $40,000

  • Land
  • 3 Acres
  • $13,333 per Acre

  Vacant N Forest Ct, Monticello, FL 32344

  Check out this amazing 3+/- acre lot in the Aucilla Forest & Meadows Subdivision in beautiful Jefferson County, FL! This spacious lot would be the perfect place to build your dream home, or place your new manufactured/mobile home! Site built, or manufactured homes must be a minimum of 720 heated square feet. The land is currently wooded with some beautiful Florida hardwoods and pines. Clear out

  Jerrod Trainer Jerrod A Trainer & Associates

  Vacant N Forest Ct, Monticello, FL 32344
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  /9

  $120,000

  • Land
  • 2.01 Acres
  • $59,701 per Acre

  40 Westview Ln, Monticello, FL 32344

  Load up and take a ride to Lloyd Fl. located between Tallahassee and Monticello Fl. Being offered "AS IS" two 1 acre parcels 18-1N-4E-0108-000G-0030 & 18-1N-4E-0108-000G-0040 for a total of 2.01 acres! Power, septic and well on site, as well as access to city water. There is a 1989 mobile home on site that may be salvageable to the right buyer, or haul it off and prepare for a new build! Bring

  Alicia Radtke All Realty Services

  40 Westview Ln, Monticello, FL 32344
• 

  

  /31

  $105,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  572 Deerwood Blvd, Greenville, FL 32331

  Handyman Opportunity! Bring your tools and check out this 3 bedroom, 2 bath, mobile home on 5 acres. Large open floorplan offers plenty of space to entertain. Screened front porch, along with a metal workshop. Home is being offered As-Is and will need some repairs as there is mildew present.

  Crystal Bochnia Madison Realty Group, LLC

  572 Deerwood Blvd, Greenville, FL 32331
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  /8

  $4,500,020

  • Land
  • 85.26 Acres
  • $52,780 per Acre

  0 Big Joe Rd Unit 2025007616, Monticello, FL 32344

  Known for its white tail deer, hog and turkey populations, this 85.26 acres in Jefferson County, FL would make a perfect hunting camp. Pristine pine tree property just minutes from Interstate 10 / Exit 225. Ideal Country Estate or weekend get-away. Seller financing available to qualified buyer.

  Florie Gage Cornerstone Coastal Properties

  0 Big Joe Rd Unit 2025007616, Monticello, FL 32344
• 

  

  /21

  $270,000

  • 4 Beds
  • 2 Baths
  • 2,310 Sq Ft

  1181 Smokehouse Farms Dr, Greenville, FL 32331

  HOME FOR SALE NEAR MONTICELLO FL. At just $117/s.f., this is a GREAT HOUSING BUY on a late model 4/2 manufactured home on 5 acres NE of charming Monticello near the Aucilla River. The move-in ready 2021-built home includes a split floor plan with a large master bedroom and walk in closet, as well as a big kitchen with a beautiful island. The 5 acre lot is mostly wooded, with well-drained soils.

  Grayson Boyd FL-GA Realty & Auction

  1181 Smokehouse Farms Dr, Greenville, FL 32331
• 

  

  /46

  $178,000

  • 3 Beds
  • 3 Baths
  • 2,635 Sq Ft

  18 Perkins Williams Rd, Monticello, FL 32344

  Opportunity to finish a traditional-style home on 2.02 acres in the Monticello countryside. Built in 2001 by a local contractor, the home is approximately 80% complete and has never been lived in. The structure needs a new roof, HVAC system, water heater, bedroom flooring, and completion of the master bath. There is visible foundation settlement—cause and extent unknown. Located in a flood

  Ashley Hartsfield Keller Williams Town & Country

  18 Perkins Williams Rd, Monticello, FL 32344
• 

  

  /70

  $1,050,000

  • 4 Beds
  • 4.5 Baths
  • 3,696 Sq Ft

  825 Rainey Run, Monticello, FL 32344

  This private 10-acre retreat is where luxury, comfort, and nature come together in perfect harmony. This stunning 4-bedroom, 4.5-bath home offers 3,696 sq. ft. of bright, open-concept living designed for both relaxation and entertaining. Step inside to find soaring ceilings, gleaming floors, and walls of windows that frame the peaceful beauty of your estate grounds and private creek. The gourmet

  Renee Dawkins Ketcham Realty Group, Inc.

  825 Rainey Run, Monticello, FL 32344
• 

  

  /70

  $989,000

  • 4 Beds
  • 3 Baths
  • 4,600 Sq Ft

  2024 Old Lloyd Rd, Monticello, FL 32344

  Square footage includes both the main house is 3200 square feet with 4 bedrooms and 3 baths. New barn apartment is 1400 square feet with 2 bedrooms and 1 bath. This would be an amazing income producing property for short and/or long term rental property of barn apt, horse boarding stables ... or even a wedding venue. This breathtaking property checks ALL of the boxes! Please see associated

  Katherine Hansli Searcy The Naumann Group Real Estate

  2024 Old Lloyd Rd, Monticello, FL 32344
• 

  

  /43

  $285,000

  • 3 Beds
  • 2 Baths
  • 2,044 Sq Ft

  300 Cedar St, Monticello, FL 32344

  Price Improvement! ~ Welcome to 300 Cedar Street ~ Located a stone's throw from Monticello's charming downtown, yet quiet & private ~ Relax in a rocking chair & enjoy sitting on your HUGE 64x8 screened in porch that runs the entire length of the back of the home & overlooks the serene 1.5 acre lot ~ Built in 1958, this single story home is a sturdy brick ranch style with 3 Bedrooms, 2 Baths,

  Jonathan Rigsby Spotlight Real Estate

  300 Cedar St, Monticello, FL 32344
• 

  

  /38

  $799,000

  • 5,139 Sq Ft

  625 E Washington St, Monticello, FL 32344

  Amazing Investment Opportunity! Own your piece of history and enjoy some great cash flow in this beautiful Downton Monticello Home. Built in 1888 and almost 4500 SF in the main house with 9 bedrooms, 7 bathrooms and common areas for the tenants. Currently set up as a rooming house with tenants. New roof 2024, new HVAC 2022 and mini splits, New kitchen and bathrooms 2022, Tankless Hot water

  Lee Hall Capital City Real Estate Group

  625 E Washington St, Monticello, FL 32344
• 

  

  /45

  $249,000

  • 4 Beds
  • 2 Baths
  • 1,812 Sq Ft

  685 E Washington St, Monticello, FL 32344

  Reduced! Perfect brick family home right downtown! Walk to the veggie stand across the street and all the Monticello shops! Renovated 4-bed, 2-bath home. New roof!! New Custom Kitchen cabinets, granite counters, and SS Appliance package perfect for all those home chefs. The open-plan kitchen opens directly into the dining and living room. New Flooring, Paint, Light fixtures, Custom closets and

  Lee Hall Capital City Real Estate Group

  685 E Washington St, Monticello, FL 32344
• 

  

  /14

  $35,000

  • Land
  • 0.09 Acre
  • $388,889 per Acre

  3C Hanger Ln, Greenville, FL 32331

  Fly in to scenic, rural north Florida, and enjoy all the area has to offer! T-Hangar is located near Monticello, FL at the longest turf runway in Florida (FL74 – 6395ft.). Pour a concrete floor and add an electric line for instant equity. Leave a car or RV in the hangar while you're back home, and take it adventuring once you arrive! 1 hour to the Gulf coast or Tallahassee, 2 hours to

  Esther Warrendorf Canopy Road Realty

  3C Hanger Ln, Greenville, FL 32331
• 

  

  /33

  $179,000

  • Land
  • 10.62 Acres
  • $16,855 per Acre

  720A Indian Hills Rd, Monticello, FL 32344

  Escape to the countryside and live your dream on this stunning 10.62-acre property! With three mobile homes currently on site, this property offers a unique opportunity for multi-generational living, rental income, or a sprawling family compound. While the mobile homes are not considered valuable, they provide a canvas for renovation or replacement. See potential in these structures or consider

  Alicia Radtke All Realty Services

  720A Indian Hills Rd, Monticello, FL 32344
• 

  

  /52

  $210,000

  • Land
  • 40 Acres
  • $5,250 per Acre

  3978 Quitman Hwy S, Greenville, FL 32331

  Welcome to 3978 S Quitman Hwy – 40 beautiful acres in the heart of Jefferson County, Florida. This versatile property is ideal for those seeking a private hunting retreat, weekend getaway, or future homesite. Over a quarter of the land is planted in pines, providing both aesthetic value and future timber potential. An older mobile home sits on-site, holding little value, but all essential

  Benjamin Sadler OaksFeather Realty

  3978 Quitman Hwy S, Greenville, FL 32331
• 

  

  /34

  $269,000

  • 3 Beds
  • 2 Baths
  • 1,654 Sq Ft

  130 Simpson Ave, Monticello, FL 32344

  Beautiful home located in historic Monticello within walking distance to downtown shopping, restaurants, and farmers market. Featuring 3 spacious bedrooms with 2 large bathrooms and a walk-in closet. This charming cottage has an extra office/study area, original fireplace, glass french doors to dining room and updates throughout while staying true to its original character. Step outside to a

  Suzanna Malone Lauer Real Estate Group LLC

  130 Simpson Ave, Monticello, FL 32344
• 

  

  /11

  $22,500

  • Land
  • 2 Acres
  • $11,250 per Acre

  0 Flatwoods, Monticello, FL 32344

  Land for Sale – Flatwoods, FL 32344. Size: 2.0 Acres. Location: Flatwoods Road, Monticello, Florida 32344. Property Highlights: Buildable lot with plenty of space; Power available on the road; 411.75 feet of road frontage; Peaceful rural setting surrounded by large parcels; No HOA – flexible use for site-built or modular homes. About 40 minutes to Tallahassee. Ideal for a private

  Andrey Rossin CASH FLOW IN MIAMI REALTY

  0 Flatwoods, Monticello, FL 32344
• 

  

  /16

  $89,900

  • Land
  • 5.4 Acres
  • $16,648 per Acre

  70 E 2nd Way, Greenville, FL 32331

  BRING OFFERS!!!!Off Grid Living? Fly a plane and Bring a horse. Paved Road frontage on this 5.40 acre parcel with perimeter fencing and cross fencing. Property was a total off-grid living arrangement at one point. Deep well with gravity made pressure tank. Solar shed and station. Tiny home with air conditioning. Feed Stall for the horse. Property was being maintained as a park like setting up

  Starbuck Rissman Steve C. Walker Realty, LLC

  70 E 2nd Way, Greenville, FL 32331
• 

  

  /9

  $144,000

  • Land
  • 9.38 Acres
  • $15,352 per Acre

  402 Mistletoe Ln, Monticello, FL 32344

  Escape to tranquility with this expansive piece of raw, rural land for sale. Offering acres of untouched beauty, this property provides the perfect opportunity to build your dream home or start your next project. With no neighbors behind, you'll enjoy complete privacy and seclusion, surrounded only by nature’s peaceful serenity. Whether you're looking for a quiet retreat, hunting grounds, or

  Melissa Montalvo Engel & Völkers Tallahassee

  402 Mistletoe Ln, Monticello, FL 32344
• 

  

  /11

  $22,000

  • Land
  • 0.52 Acre
  • $42,308 per Acre

  0 E Capps Hwy, Lamont, FL 32336

  For Sale: Buildable Vacant Lot – 0.52 Acres on E Capps Hwy, Lamont, FL 32336.Discover the potential of this 0.52-acre buildable lot with 624.57 feet of road frontage on E Capps Hwy in peaceful Lamont, Florida. With power available at the road, this parcel is ready for your vision—whether you're planning a new home, a weekend retreat, or a smart investment. Zoning: Buildable residential

  Andrey Rossin CASH FLOW IN MIAMI REALTY

  0 E Capps Hwy, Lamont, FL 32336

Showing Results 41 - 80, Page 2 of 3