Homes for Sale in 32344

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  /48

  $254,000

  • 2 Beds
  • 2 Baths
  • 1,411 Sq Ft

  490 N Cherry Ct, Monticello, FL 32344

  This is the kind of home you can move into and simply enjoy. Located in Cherry Street Square, a desirable community in the heart of historic Monticello, this immaculate two-bedroom, two-bath townhome with a bonus room or office has been thoughtfully updated from top to bottom. The interior feels fresh, bright and completely move-in ready, with luxury vinyl plank flooring, updated doors and

  

  Lindsey Sadler

  OaksFeather Realty

  490 N Cherry Ct, Monticello, FL 32344
• 

  

  /2

  $199,000

  • Land
  • 5.85 Acres
  • $34,017 per Acre

  TBD Old Tung Grove Rd, Monticello, FL 32344

  Wooded 5.85 acre homesite. Convenient to Tallahassee. Access road has not been cleared yet to access this parcel.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD Old Tung Grove Rd, Monticello, FL 32344
• 

  

  

  /41

  $399,000

  • 5 Beds
  • 2 Baths
  • 2,184 Sq Ft

  10283 Ashville Hwy, Greenville, FL 32331

  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

  Lee Hall Bespoke Realty of Tallahassee

  10283 Ashville Hwy, Greenville, FL 32331
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  /70

  $470,000

  $34K PRICE INCREASE

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

  78 Fen Ct, Monticello, FL 32344

  Photos of previous homes. Come choose all your finishes and upgrades. Home is just finishings the framing stage of construction. Amazing new construction 3 bedroom 2 bathroom by Nailed It Tallahassee LLC. Luxurious master suite, Kitchen made of dreams, this is a must see!

  Amber McKinney Hamilton Realty Advisors LLC

  78 Fen Ct, Monticello, FL 32344
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  /68

  $695,000

  • 5 Beds
  • 3 Baths
  • 3,536 Sq Ft

  2247 Waukeenah Hwy, Monticello, FL 32344

  Just 3 miles south of Monticello, FL and only 2.5 miles from I-10, this 10.45 acre working homestead has been thoughtfully set up for country living, livestock and extended family. The 3,536 sq. ft. home features 4 bedrooms/2 baths in the main house (with the set up for an additional bath upstairs) master is conveniently located downstairs with two walk-in closets, private access, plenty of

  Alicia Radtke All Realty Services

  2247 Waukeenah Hwy, Monticello, FL 32344
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  /34

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,980 Sq Ft

  112 Long Leaf Dr, Monticello, FL 32344

  Nearly 6 Acres of Opportunity in Beautiful Monticello! If you're looking for space, privacy, and the possibility to create a home that truly reflects your vision, this property is it! This spacious 3-bedroom, 2-bathroom modular home offers a desirable open and split floor plan with generously sized living spaces. The expansive primary suite provides a private retreat and features a walk-in

  Marylou Johnston Keller Williams Town & Country

  112 Long Leaf Dr, Monticello, FL 32344
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  /50

  $117,900

  $2K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,612 Sq Ft

  1150 Sage St, Monticello, FL 32344

  Investor special! Cash only!

  Matthew Soltis Robert Slack LLC

  1150 Sage St, Monticello, FL 32344
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  /66

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft

  195 Coopers Pond Rd, Monticello, FL 32344

  Wonderful family home in great neighborhood~Located on a quiet street, this home sits on a full acre and is ready for new owners~huge walk-in shower~breakfast nook~jetted tub in 2nd bathroom~walk-in closet in master~screened porch overlooking private backyard~partially fenced~2-car garage~nice yard with large oaks ~~Zero turn lawnmower included with acceptable offer~~

  Renee Smawley Steve C. Walker Realty, LLC

  195 Coopers Pond Rd, Monticello, FL 32344
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  /70

  $915,000

  • 3 Beds
  • 2.5 Baths
  • 2,412 Sq Ft

  4216 W Washington Hwy, Monticello, FL 32344

  Tucked away on 10.87 private acres behind its own gated entrance in the sought-after Rainey Run community, this custom-built home offers the perfect balance of quality craftsmanship, modern comfort, and peaceful country living. Built by Hannon Construction in 2023, the 3-bedroom, 2.5-bath home spans 2,412 square feet and was thoughtfully designed with timeless finishes and functional spaces

  Savannah Stephens Hill Spooner & Elliott Inc

  4216 W Washington Hwy, Monticello, FL 32344
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  /6

  $39,900

  • Land
  • 1.91 Acres
  • $20,890 per Acre

  76 Barnes Rd, Monticello, FL 32344

  Discover the perfect spot to build your dream home or weekend getaway on this 1.91-acre property in Monticello! Featuring paved road frontage, a partially cleared homesite, and plenty of room to enjoy the surrounding natural beauty, this property offers the ideal balance of privacy and convenience. Located with easy access to both Monticello, FL and Thomasville, GA, you’ll enjoy peaceful country

  Crystal Bochnia Madison Realty Group, LLC

  76 Barnes Rd, Monticello, FL 32344
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  /4

  $39,900

  • Land
  • 1.91 Acres
  • $20,890 per Acre

  Vacant Barnes Rd, Monticello, FL 32344

  Discover the perfect spot to build your dream home or weekend getaway on this 1.91-acre property in Monticello! Featuring paved road frontage, a partially cleared homesite, and plenty of room to enjoy the surrounding natural beauty, this property offers the ideal balance of privacy and convenience. Located with easy access to both Monticello, FL and Thomasville, GA, you’ll enjoy peaceful country

  Crystal Bochnia Madison Realty Group, LLC

  Vacant Barnes Rd, Monticello, FL 32344
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  /9

  $175,000

  • Land
  • 37 Acres
  • $4,730 per Acre

  Vacant E Washington Hwy, Monticello, FL 32344

  37 ACRES, AUCILLA RIVER HUNTING TRACT NEAR MONTICELLO. FL. Fronts on US 90 ½ mile west of the Aucilla River—perhaps the most prolific wildlife corridor in the county. The NE half of the property is an extension of the river’s drainway and borders SRWMD land on two sides. It’s a great wildlife habitat. The SW half along US 90 and Gramling Road is composed of a soil type (Plummer) suitable for

  Hines Boyd FL-GA Realty & Auction

  Vacant E Washington Hwy, Monticello, FL 32344
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  /36

  $279,000

  • 3 Beds
  • 1.5 Baths
  • 1,880 Sq Ft

  380 N Jefferson St, Monticello, FL 32344

  Step into the timeless charm of historic downtown Monticello, Florida, with this unique property offering nearly 2000 square feet of character and endless potential. Located within walking distance of downtown shopping, dining, and community events, this property is perfectly suited for residential living, commercial use, or a combination of both. Featuring beautiful original wood floors, soaring

  

  Pam Kelly

  Kelly & Kelly Properties, Inc

  380 N Jefferson St, Monticello, FL 32344
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  /7

  $104,000

  $5K PRICE DROP

  • Land
  • 5 Acres
  • $20,800 per Acre

  130 Sweetfield Rd, Monticello, FL 32344

  Mobile-home-friendly property with a cleared homesite and an existing well, septic system, and electrical service already on the property. Seller financing is available. Conveniently located near I-10 and approximately 30 minutes from Tallahassee. Bring your home plans and enjoy a quiet country setting with room for animals, gardening, outdoor projects, and additional storage. Fence the property

  Moe Mossa Savvy Avenue, LLC

  130 Sweetfield Rd, Monticello, FL 32344
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  /44

  $235,000

  • 3 Beds
  • 1 Bath
  • 1,700 Sq Ft

  810 E Dogwood St, Monticello, FL 32344

  Step back in time and discover the charm of this classic Monticello home, offering timeless character and endless possibilities. Built in 1915, this Craftsman-style residence features 1,700 square feet of living space with hardwood floors, separate living and dining areas that reflect the home's historic appeal, 3 full bedrooms, with a large mud room and separate sitting room, a wood-burning

  Michael Balanoff Re/Max Professionals Realty

  810 E Dogwood St, Monticello, FL 32344
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  /47

  $949,000

  • 3 Beds
  • 2.5 Baths
  • 2,790 Sq Ft

  307 Crabapple Ln, Monticello, FL 32344

  A rare opportunity to own a truly one-of-a-kind custom estate! Nestled on a private, fully fenced homesite overlooking 26 acres of golf course-like grounds, this 2021 custom-build home offers over 2,700 square feet of thoughtfully designed living space with breathtaking 270° views, including peaceful creek frontage. Built for both luxury and peace of mind, the home features hurricane shutters, a

  Shelley Poppell Clover Key Realty

  307 Crabapple Ln, Monticello, FL 32344
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  /2

  $125,000

  • Land
  • 5.96 Acres
  • $20,973 per Acre

  0 Eastwood Unit 402606, Monticello, FL 32344

  Back on the market - Discover the perfect place to build your dream home on this beautiful nearly 6-acre parcel! Enjoy the peace and privacy of country living with the convenience of being just minutes from the interstate and a short drive to Tallahassee. With plenty of room for your custom home, workshop, gardens, or recreational space, the possibilities are endless! Whether you’re looking to

  D. Scott Kilgore Superior Realty Group LLC

  0 Eastwood Unit 402606, Monticello, FL 32344
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  /2

  $79,000

  • Land
  • 19,602 Sq Ft
  • $175,556 per Acre

  Lot 12 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes BOTH Lot 12 & 23 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 12 E Washington St, Monticello, FL 32344
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  /2

  $79,000

  • Land
  • 19,602 Sq Ft
  • $175,556 per Acre

  Lot 13 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes BOTH Lot 13 & 22 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 13 E Washington St, Monticello, FL 32344
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  /2

  $69,000

  • Land
  • 19,602 Sq Ft
  • $153,333 per Acre

  Lot 14 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes BOTH Lot 14 & 21 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 14 E Washington St, Monticello, FL 32344
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  /2

  $85,000

  • Land
  • 19,602 Sq Ft
  • $188,889 per Acre

  Lot 11 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes BOTH Lot 11 & 24 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 11 E Washington St, Monticello, FL 32344
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  /2

  $85,000

  • Land
  • 2.05 Acres
  • $41,463 per Acre

  Lot 25 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes 10 Lots- 25-35 (Survey) totaling 2.05 Acres.

  Liz Kuntz Keller Williams Town & Country

  Lot 25 E Washington St, Monticello, FL 32344
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  /2

  $69,000

  • Land
  • 19,602 Sq Ft
  • $153,333 per Acre

  Lot 16 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes 4 Lots- 16 & 17 with 18 & 19 directly behind it, totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 16 E Washington St, Monticello, FL 32344
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  /2

  $69,000

  • Land
  • 19,602 Sq Ft
  • $153,333 per Acre

  Lot 15 E Washington St, Monticello, FL 32344

  Brand New Home Options Available starting in the $300's or Build to Suit! Fantastic Location on almost 1/2 an Acre in Town! Super Convenient walking distance to restaurants, shopping, and entertainment. Lots of possibilities! Come Check it out! Water & Sewer Available. Owner Financing Options too. This Listing includes BOTH Lot 15 & 20 directly behind it totaling .45 Acre.

  Liz Kuntz Keller Williams Town & Country

  Lot 15 E Washington St, Monticello, FL 32344
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  /69

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 4,762 Sq Ft

  974 Rainey Run, Monticello, FL 32344

  **Some Photos are Virtually Enhanced** Experience luxury living in the prestigious gated community of Rainey Run. This is where privacy, nature, and convenience come together on 10 breathtaking acres. Surrounded by towering hardwoods and abundant wildlife, this remarkable property offers a convenient peaceful retreat. Built in 2020, this custom home showcases quality craftsmanship with a highly

  Renee Dawkins Dawkins Realty LLC

  974 Rainey Run, Monticello, FL 32344
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  /2

  $95,000

  • Land
  • 2.22 Acres
  • $42,793 per Acre

  450 Oconee Ln, Monticello, FL 32344

  Vacant building lot; inside the city limits, city water and sewer are available, all high and dry; very nice neighborhood, no HOA.

  Steve Walker Steve C. Walker Realty, LLC

  450 Oconee Ln, Monticello, FL 32344
• 

  /2

  $254,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,235 Sq Ft

  360 Bowman St, Monticello, FL 32344

  New construction; very convenient to downtown; house is close to completion - should be ready in about 45 days.

  Steve Walker Steve C. Walker Realty, LLC

  360 Bowman St, Monticello, FL 32344
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  /2

  $350,500

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  1565 Sweetbay Ct, Monticello, FL 32344

  This home is currently coming out of the permitting phase. New construction will start in the next week. Completion date should be approx 4 months or less. We will update the comments as the construction progresses. Picture is virtual. More to come as construction continues.

  Steve Walker Steve C. Walker Realty, LLC

  1565 Sweetbay Ct, Monticello, FL 32344
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  /19

  $424,900

  New Construction $20K PRICE DROP

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

  855 S Waukeenah St, Monticello, FL 32344

  Stunning New Construction recently 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 features vinyl plank flooring, granite countertops, walk in tile shower and tub in master, upgraded trim package, and stainless appliances. Nice large back porch with deck, over looking the large

  Jared Parramore Coastwise Realty

  855 S Waukeenah St, Monticello, FL 32344
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  /46

  $325,000

  • 4 Beds
  • 2 Baths
  • 2,304 Sq Ft

  947 Piney Woods Rd, Monticello, FL 32344

  Charming 2022 Mobile Home on 5 Peaceful Acres A rare blend of modern comfort and wide-open space, this 2022 mobile home sits on 5+ acres—perfect for anyone craving privacy, freedom, and room to grow. Whether you dream of a hobby farm, a quiet country retreat, or simply a place with no close neighbors, this property delivers. Embrace freedom of country living with the convenience of a modern home.

  

  Brian Bachman

  Kelly & Kelly Properties, Inc

  947 Piney Woods Rd, Monticello, FL 32344
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  /36

  $584,000

  • 3 Beds
  • 3.5 Baths
  • 2,148 Sq Ft

  8250 Waukeenah Hwy, Monticello, FL 32344

  Enjoy two private year around spring fed ponds! Escape to your own private sanctuary on 30 breathtaking acres where nature, privacy, and craftsmanship come together. This custom-built retreat features soaring vaulted ceilings, expansive windows, & French doors- blurring the line between indoors and out, flooding every room with natural light and serene views. 2 Bed, 2.5 Bath, thoughtfully

  

  Bhishma Benedict

  FLORIDA HOMES REALTY & MORTGAGE GVILLE

  8250 Waukeenah Hwy, Monticello, FL 32344
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  /2

  $139,000

  • Land
  • 5 Acres
  • $27,800 per Acre

  TBD Orchard Ln, Monticello, FL 32344

  Great Location in Western Jefferson County offering country living with the convenience of Tallahassee only minutes away. Wooded 5 acres on private lane. Restricted for site built homes with minimum of 1200 sq ft heated and cooled. Adjoining 5 available for sale.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  TBD Orchard Ln, Monticello, FL 32344
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  /18

  $25,000

  • Land
  • 4 Acres
  • $6,250 per Acre

  TBD S Salt Rd, Monticello, FL 32344

  Palmetto's, Pines, Magnolia's and Titi's with native ferns! Small little piece of land 4 acres +/-, for a hunting getaway! Dry as a bone right now due to drought conditions and perfect to get your deer stand set up! This beautiful old Florida habitat is great for wildlife observation, birding, native forest growth, riding four-wheelers, building nesting boxes for ducks and bats or a hammock

  

  Lynette Sirmon

  All Realty Services

  TBD S Salt Rd, Monticello, FL 32344
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  /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
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  /34

  $425,000

  • 5,818 Sq Ft

  2664 W Washington Hwy Unit Two Homes, Monticello, FL 32344

  Two houses perfect for generational living or rental income. These move-in-ready homes are in good condition, convenient to Monticello while maintaining privacy. The larger home is a 1550's era brick ranch-style home that is well maintained with newer roof (2022), new electric (2025), new plumbing (2025), tankless water heater and whole house generator. The main living area is 2,659 sf with 5

  Heather Boyd FL-GA Realty & Auction

  2664 W Washington Hwy Unit Two Homes, Monticello, FL 32344
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  /29

  $429,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  285 Mallard Ln, Monticello, FL 32344

  *Jefferson County peaceful country living with a waterfront backdrop! Built in 2008, this well maintained 3 bedroom, 2 bath home sits on 4.89 beautifully (mostly cleared) acres offering privacy and natural beauty backing directly up to Lloyd Lake- perfect for relaxing evenings with scenic views. Pretty rocking chair front porch as well as a screened in back porch with a propane hookup for

  Shelley Duke Red Bird Realty

  285 Mallard Ln, Monticello, FL 32344
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  /3

  $1,190,000

  • 4 Beds
  • 4 Baths
  • 3,043 Sq Ft

  4264 Safari Run, Tallahassee, FL 32309

  New construction, East side of town this 4 Bedroom 4 Bath home with office and private sitting in master this home is a luxury on 2/12 acres. completion in early Aug 2026

  Robert Paynter Keller Williams Town & Country

  4264 Safari Run, Tallahassee, FL 32309
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  /14

  $200,000

  • 3 Beds
  • 1.5 Baths
  • 1,304 Sq Ft

  1550 Tennessee Ave, Monticello, FL 32344

  Charming and affordable home on the North side of Monticello in Nobles Subdivision. 3 BR 1.5 Baths. Upgrades in 2021 include new ac, new water heater, new roof. Recent interior paint. Large fenced backyard.

  

  Barry Kelly

  Kelly & Kelly Properties, Inc

  1550 Tennessee Ave, Monticello, FL 32344
• 

  

  /24

  $298,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,351 Sq Ft

  1070 Partridge Ln, Monticello, FL 32344

  Currently under construction. Interior pictures are from a previous model home. Approximately 60 days until completion. Home qualifies for USDA financing.

  Steve Walker Steve C. Walker Realty, LLC

  1070 Partridge Ln, Monticello, FL 32344
• 

  /2

  $319,900

  New Construction $2K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,550 Sq Ft

  300 Bowman St, Monticello, FL 32344

  Recently built home featuring spacious open floor plan. Kitchen has raised cabinets, granite counters, stainless steel appliances, large island with plenty of seating & a pantry....overlooks spacious family area with plenty of room for large gatherings, plus separate dining space. First floor also offers 1/2 bath and large storage area under stairs. Upstairs you are greeted with open reading area

  Steve Walker Steve C. Walker Realty, LLC

  300 Bowman St, Monticello, FL 32344

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