Vintage homes for sale & real estate in Madison County, FL

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ABOUT THIS HOME
Vintage Home for sale in Madison County, FL:
One of those "glass half full" places! You will need your rose-colored glasses on for sure. Some people will want to tear it down and others will see potential. It is being lived in but the appliances belong to the tenant as well as the air conditioning units. This home will NOT be financeable, and it does NOT have casualty insurance coverage NOR could you obtain insurance on it in its present condition. There is a huge Magnolia tree growing into the front center edge of the roof line on the 8x16 front porch. Numerous areas of wood rot and foundation issues. Electrical and Plumbing issues. Well and Septic is very old. Some windows do not operate. Roof is not leaking but it is very

$40,000

2 beds1 bath1,050 sq ft

4285 NW Us 221, Greenville, FL

0.34 acre lot • Parking • Built 1960

ABOUT THIS HOME
Vintage Home for sale in Madison County, FL:
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

$299,000

4 beds2 baths2,862 sq ft

1534 SW Main St, Greenville, FL 32331

0.75 acre lot • 2 garage spots • Built 1915

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Madison County, FL:
This beautifully restored early-1900s home in the heart of Pinetta, Florida blends timeless character with thoughtful modern updates while preserving many original features. Renovations include updated wiring and plumbing, vinyl siding, insulated windows, and a brand new metal roof. The kitchen offers a gas stove and existing appliances, and a tankless water heater provides continuous hot water. Inside, you’ll find high ceilings, some original wood walls, and two and a half updated bathrooms, including a walk-in shower and a Jacuzzi tub in the second bath. A large screened front porch overlooks the fenced yard, which offers plenty of space for gardening, outdoor activities, or simply

$177,500

3 beds2.5 baths1,444 sq ft

242 NE Bellville Rd, Pinetta, FL 32350

Metal roof • Updated wiring • Insulated windows

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Madison County, FL:
Welcome to the charming town of Madison, where small-town character and rich history create a wonderful place to call home. This spacious 4-bedroom, 3-bathroom property offers plenty of room to grow along with exciting opportunities to add your own personal style. Inside, you’ll immediately notice the beautiful vaulted wood ceilings that stretch across the living, dining, and kitchen areas, creating a warm and inviting space perfect for everyday living and gatherings with family and friends. Built with durable concrete block construction and topped with a metal roof, the home offers long-lasting quality and peace of mind. Tucked away on a cul-de-sac at the end of a quiet, private road

$231,500

4 beds3 baths2,480 sq ft

493 NE Shelby Ext, Madison, FL 32340

Metal roof • Large backyard • Workshop in backyard

ABOUT THIS HOME
Vintage Home for sale in Madison County, FL:
Charming Country Cottage on 3.67 Acres! Welcome home to peaceful country living! This charming 3-bedroom, 1-bath cottage sits on 3.67 beautiful acres, offering plenty of room to enjoy the outdoors, keep animals or horses, or simply relax in a quiet setting. A welcoming wraparound deck enhances the home’s charm, providing the perfect space for morning coffee, evening sunsets, entertaining guests, or simply taking in the peaceful country views that surround the property. Inside, you’ll find a spacious living room, a large laundry/utility room with extra storage, and the potential to add a second bathroom. The oversized workshop/garage is ideal for hobbies, equipment, or additiona

$270,000

3 beds1 bath1,451 sq ft

839 NE Post Rd, Madison, FL 32340

Wraparound deck • Oversized workshop • 3.67 acres

Property at 383 NE Ridge Loop, Madison, FL 32340, 4 beds, 2 baths

$129,900

4 beds2 baths1,794 sq ft

383 NE Ridge Loop, Madison, FL 32340

Property at 219 NE Livingston St, Madison, FL 32340, 6 beds, 4.5 baths

$715,000

6 beds4.5 baths3,744 sq ft

219 NE Livingston St, Madison, FL 32340

Property at 485 SW Jordan St, Madison, FL 32340, 4 beds, 3.5 baths

$235,000

4 beds3.5 baths2,688 sq ft

485 SW Jordan St, Madison, FL 32340

Property at 4087 NW Honey Lake Rd, Greenville, FL 32331, 3 beds, 3 baths

$700,000

3 beds3 baths1,540 sq ft

4087 NW Honey Lake Rd, Greenville, FL 32331

Property at 277 SE Woodlawn St, Madison, FL 32340, 4 beds, 3 baths

$259,000

4 beds3 baths2,632 sq ft

277 SE Woodlawn St, Madison, FL 32340

Property at 146 SE Bunker St, Madison, FL, 3 beds, 2 baths

$195,000

3 beds2 baths1,500 sq ft

146 SE Bunker St, Madison, FL

Property at 231 SW Rutledge St, Madison, FL 32340, 4 beds, 3 baths

$500,000

4 beds3 baths3,910 sq ft

231 SW Rutledge St, Madison, FL 32340

Property at 1055 NE Cherry Lake Cir, Madison, FL 32340, 3 beds, 3 baths

$675,000

3 beds3 baths2,040 sq ft

1055 NE Cherry Lake Cir, Madison, FL 32340

Property at 227 SW Range Ave, Madison, FL 32340, 3 beds, 7 baths

$474,999

3 beds7 baths7,375 sq ft

227 SW Range Ave, Madison, FL 32340

Property at 610 SE Askew Ave, Madison, FL 32340

$16,900

Land1.00 acre (lot)

610 SE Askew Ave, Madison, FL 32340

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ABOUT THIS HOME
Vintage Home for sale in Madison County, FL:
Investor special! Cash only!

$117,900

5 beds2 baths2,612 sq ft

1150 Sage St, Monticello, FL 32344

0.63 acre lot • Built 1914 • Listed 13 days

ABOUT THIS HOME
Vintage Home for sale in Madison County, FL:
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 high ceilings, and architectural details rarely found in modern construction. , this historic gem is full of warmth and personality. A spacious covered front porch provides the perfect place to relax and enjoy the charm of one of North Florida's most picturesque downtown neighborhoods. While the pr

$279,000

3 beds1.5 baths1,880 sq ft

380 N Jefferson St, Monticello, FL 32344

Flexible zoning • Original wood floors • 9,583 sq ft lot

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Madison County, FL:
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 fireplace in the living room and primary bedroom, soaring ceilings, and charming details throughout. Situated on a spacious . 23 acre in-town lot, the property offers convenient access to Monticello's historic downtown, where you'll enjoy locally owned shops, dining, and community events. The spacious b

$235,000

3 beds1 bath1,700 sq ft

810 E Dogwood St, Monticello, FL 32344

Large deck • Spacious backyard • Fully fenced

ABOUT THIS HOME
Vintage Home for sale in Madison County, FL:
Country living with room to spread out! Nestled on 2 peaceful acres, this well-maintained property offers the perfect blend of functionality and outdoor enjoyment. Inside, you'll find fresh updates including newer flooring and interior paint, creating a clean and inviting atmosphere. The durable metal roof adds long-term value and peace of mind. Step outside to enjoy the covered patio overlooking the spacious grounds, ideal for relaxing or entertaining. The property is equipped with irrigation across much of the acreage, providing excellent opportunities for gardening, landscaping, or hobby farming. A detached workshop/shed with welding hookups offers a versatile space for equipment, projec

$194,500

3 beds2.5 baths1,152 sq ft

4298 River Rd, Live Oak, FL 32060

Durable metal roof • 2 peaceful acres • Welding hookups

ABOUT THIS HOME
Vintage Home for sale in Madison County, FL:
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.

$200,000

3 beds1.5 baths1,304 sq ft

1550 Tennessee St, Monticello, FL 32344

New water heater • Nobles subdivision • New ac

ABOUT THIS HOME
Vintage Home for sale in Madison County, FL:
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 ther

$736,951

2 beds1 bath1,296 sq ft

10481 Ashville Hwy, Greenville, FL 32331

Recreational spot • Two ponds • Room for pasture

Property at 480 S Jefferson St Unit -, Monticello, FL 32344, 4 beds, 4 baths

$364,900

4 beds4 baths2,750 sq ft

480 S Jefferson St Unit -, Monticello, FL 32344

Property at 209 Island St, Lake Park, GA 31636, 5 beds, 3 baths

$595,000

5 beds3 baths4,342 sq ft

209 Island St, Lake Park, GA 31636

Property at 365 S Mulberry St, Monticello, FL 32344, 6 beds, 3.5 baths

$699,000

6 beds3.5 baths3,114 sq ft

365 S Mulberry St, Monticello, FL 32344

Property at 1628 N Jefferson Hwy, Monticello, FL 32344, 3 beds, 2.5 baths

$398,900

3 beds2.5 baths3,127 sq ft

1628 N Jefferson Hwy, Monticello, FL 32344

Property at 625 E Washington St, Monticello, FL 32344, 7 beds, 7 baths

$599,000

7 beds7 baths5,139 sq ft

625 E Washington St, Monticello, FL 32344

Property at 220 Eaton St, Monticello, FL 32344, 3 beds, 1 bath

$239,000

3 beds1 bath1,164 sq ft

220 Eaton St, Monticello, FL 32344

Property at 701 N Barber Hl, Lamont, FL 32336, 4 beds, 2 baths

$425,000

4 beds2 baths2,314 sq ft

701 N Barber Hl, Lamont, FL 32336

Property at 4651 NW 49th Pl, Jennings, FL 32052, 5 beds, 5 baths

$1,249,900

5 beds5 baths3,509 sq ft

4651 NW 49th Pl, Jennings, FL 32052

Property at 7091 River Rd, Live Oak, FL 32060, 2 beds, 1 bath

$550,000

2 beds1 bath1,112 sq ft

7091 River Rd, Live Oak, FL 32060

Property at 1239 Ben Bates St, Jennings, FL 32053, 2 beds, 2 baths

$159,000

2 beds2 baths1,513 sq ft

1239 Ben Bates St, Jennings, FL 32053

Property at 515 E Palmer Mill Rd, Monticello, FL 32344, 3 beds, 3 baths

$529,000

3 beds3 baths2,187 sq ft

515 E Palmer Mill Rd, Monticello, FL 32344

Property at 930 E Pearl St, Monticello, FL 32344, 4 beds, 3 baths

$395,000

4 beds3 baths3,188 sq ft

930 E Pearl St, Monticello, FL 32344

Property at 4546 NW 24th Ave, Jasper, FL 32052

$55,000

Land2.50 acres (lot)

4546 NW 24th Ave, Jasper, FL 32052

Property at 5731 NW 47th Way, Jennings, FL 32053

$109,900

Land10.00 acres (lot)

5731 NW 47th Way, Jennings, FL 32053

Vintage Homes for Sale in Madison County

There are currently 15 vintage homes for sale in Madison County at a median listing price of $300K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Madison County stay on the market for 85 days. This map is refreshed with the newest listings in Madison County every 15 minutes.

In the past month, 8 homes have been sold in Madison County. In addition to houses in Madison County, there were also 0 condos, 1 townhouse, and 1 multi-family unit for sale in Madison County last month. Find your dream home in Madison County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Madison County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Madison County. If you're looking to sell your home in the Madison County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Madison County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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