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

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ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Classic 1926 Craftsman in Beautiful Monticello, Florida. Step into the timeless charm of this beautiful home offering more than 2,700 square feet of heated and cooled living space and approximately 3,248 square feet under roof. Set on a spacious one-acre lot, this distinctive home combines historic character, generous living spaces, and the convenience of small town living. Inside, you'll find high ceilings and large, inviting rooms throughout, along with beautiful architectural details that give the home its warm and gracious character. The heart of the home is a large eat-in kitchen, complemented by a formal dining room and spacious living room perfect for cozy evenings and entertaining.

$385,000

4 beds2 baths2,750 sq ft

1410 E Pearl St, Monticello, FL 32344

One acre lot • Large eat-in kitchen • Formal dining room

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Experience the charm of an established home with the modern comfort and appeal of new construction in historic district with a short walk to downtown, This beautifully transformed LIKE NEWCONSTRUCTION 4-bedroom, 2-bath brick home offering 1,844 heated and cooled square feet has undergone an extensive renovation, delivering a fresh, updated living experience from the inside out. New metal roof, and granite countertops. Why settle for an ordinary remodel when you can own a home practically rebuilt from the inside out?

$349,900

4 beds2 baths1,844 sq ft

1015 S Jefferson St, Monticello, FL 32344

Extensive renovation • New metal roof • Granite countertops

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Come check out this sweet cottage nestled in charming Monticello! This 1947 property is ready for the next chapter of its distinguished journey. Move in ready with tons of updates including recent kitchen appliances, HVAC and hot water. Tucked in on desirable Pearl St this house lives bigger than it looks with open kitchen, dining and living spaces. Sip coffee in the mornings under your very own century oak tree! Walking distance to historic Monticello’s downtown for shopping, restaurants and local butcher and farmers markets. Small town living at its best, but convenient to Tallahassee and Thomasville.

$274,500

2 beds1 bath1,090 sq ft

1195 E Pearl St, Monticello, FL 32344

Hvac • Century oak tree • Hot water

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Situated on over half an acre and within walking distance of charming downtown Monticello, this carefully maintained home offers great bones, plenty of space, and so much potential to make it your own. The fully fenced yard is lined with mature greenery, creating a wonderful sense of privacy while still giving you plenty of room to enjoy the outdoors. Inside, you’ll find an open kitchen, living, and dining area, plus a large separate family room perfect for entertaining, hosting family and friends, or creating an additional flex space. A two-car carport provides covered parking, while a ramp to the entrance offers easy accessibility. Major updates include a 2014 roof and 2016 HVAC, wa

$175,000

3 beds1 bath1,300 sq ft

380 Poplar St, Monticello, FL 32344

Over half an acre • Mature greenery • Two-car carport

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Discover the charm and versatility of this cozy cottage style home conveniently located on S. Jefferson Street in Monticello, Fl. Zoned B2 Business use, this property offers flexibility for both personal use and potential business opportunities. The home features one bedroom and one bathroom, a cozy kitchen, and a large open living/family/dining room that creates a comfortable, inviting space for relaxing or entertaining. Private backyard is perfect for enjoying outdoors with good space for grilling and relaxing. With its cottage charm, flexible zoning, convenient location, and private outdoor space, this property offers a unique opportunity for a homeowner, investor, or entrepreneur looki

$179,000

1 bed1 bath806 sq ft

620 S Jefferson St, Monticello, FL 32344

Private backyard • Convenient location • Cottage style home

Property at 185 W Walnut St, Monticello, FL 32344, 3 beds, 2.5 baths

$279,000

3 beds2.5 baths1,880 sq ft

185 W Walnut St, Monticello, FL 32344

Property at 43 Depot St, Lamont, FL 32336, 3 beds, 3 baths

$239,900

3 beds3 baths1,617 sq ft

43 Depot St, Lamont, FL 32336

Property at 515 Sunset Dr, Monticello, FL 32344, 3 beds, 2 baths

$299,900

3 beds2 baths2,583 sq ft

515 Sunset Dr, Monticello, FL 32344

Property at 1550 E Washington St Unit -, Monticello, FL 32344, 8 beds, 8 baths

$525,000

8 beds8 baths5,027 sq ft

1550 E Washington St Unit -, Monticello, FL 32344

Property at 520 E High St, Monticello, FL 32344, 3 beds, 2 baths

$175,000

3 beds2 baths1,825 sq ft

520 E High 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 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 1550 Tennessee St, Monticello, FL 32344, 3 beds, 1.5 baths

$200,000

3 beds1.5 baths1,304 sq ft

1550 Tennessee St, Monticello, FL 32344

Property at 10481 Ashville Hwy, Greenville, FL 32331, 2 beds, 1 bath

$736,951

2 beds1 bath1,296 sq ft

10481 Ashville Hwy, Greenville, FL 32331

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

$239,000

3 beds1 bath1,164 sq ft

220 Eaton St, Monticello, FL 32344

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NEW 17 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Charming 3-Bedroom Home on a Spacious Corner Lot in Perry, Florida! Discover the possibilities in this inviting 3-bedroom, 1-bath home located within the city limits of Perry, Florida. Full of character and classic Southern charm, this property features beautiful hardwood floors, warm pine walls, and distinctive redwood kitchen cabinetry that give the home a unique, timeless feel. The kitchen comes equipped with a stove, oven, and refrigerator, while central heat, an existing A/C unit, and several updated windows offer added everyday convenience. Outside, the combination of wood and vinyl siding adds to the home's appeal, and the spacious corner lot provides room to garden, entertain, or cr

$149,000

3 beds1 bath1,337 sq ft

512 Wilder St, Perry, FL 32347

Central heat • Existing a c unit • Updated windows

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
COUNTRY CHARM AT ITS FINEST! Absolutely charming country home nestled among majestic, centuries-old oak trees, lush native vegetation, and beautiful fruit trees! This picturesque property offers the perfect blend of peaceful country living, natural beauty, and everyday comfort, with no neighbors in sight! Deer and other native wildlife frequently roam the property, adding to the peaceful, natural setting and making this a true country retreat. Originally built in 1940, with an addition completed in the late 1970s, this home offers a wonderful combination of historic character and comfortable living. Featuring 4 bedrooms, 1 bath, and 1,749 heated and cooled square feet, the home showcases so

$269,000

4 beds1 bath1,749 sq ft

12110 Morris Steen Rd, Greenville, FL 32331

Mature landscaping • 1.7 acre lot • 2 parking spots

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Fresh updates. Small-town charm. Just $145,000. This CONCRETE BLOCK 3-bedroom home in beautiful Greenville, Florida, offers a long list of improvements: a new roof, flooring, windows, ceilings, doors, kitchen, and lighting fixtures. Situated on . 54 acres with city water and city sewer, it also features a detached 12x12 man cave with a brick barbecue pit. A 10x16 south facing screened porch gives additional living space perfect for gathering, relaxing, and enjoying a window on the world. Plus 12x14 storage building also. Set in a lovely section of this charming North Florida town, this home offers an appealing combination of updates, outdoor space, and affordability. Want loved ones close

$145,000

3 beds1 bath1,271 sq ft

147 SW Harby Ave, Greenville, FL 32331

New ceilings • New kitchen • New doors

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Fixer-Upper with Potential! Bring your vision and creativity to this property! This home is in need of repairs and updates but offers a great opportunity for investors or buyers looking for a renovation project. With some TLC, this property could be transformed into something special. Don’t miss the opportunity to make it your own!

$80,000

3 beds1.5 baths1,140 sq ft

201 Alice St, Perry, FL 32348

0.24 acre lot • Parking • Built 1958

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
PRICED TO SELL! THIS IS THE DEAL OF THE YEAR! Multi generational estate with detached guest quarters, both concrete block structures fully fenced, 3 bdrms, 1.5 baths in the main home, 1 Bdrm/1 Bth in guest quarters plus a double car garage. City water, city sewer, new metal roof, new electric, new plumbing, new fixtures, new flooring, new HVAC in main home, new mini split in guest home, new multi level wooden deck plus front and back stairways to guest home, both have new kitchens and new baths, all appliances are new. Take your golf cart to the post office, enjoy evening strolls on the quiet, small town, city streets, nearby city park with kiddie slash pad. Interstate close by with easy ac

$195,000

4 beds2.5 baths1,954 sq ft

158 SW Harby Ave, Greenville, FL 32331

New metal roof • New plumbing • New electric

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
CASH DEAL ONLY! These photos have been edited to appear the home is vacant. This handyman special is full of potential and offers good, solid bones in a convenient downtown Perry location. Featuring 2 bedrooms and 1 bath, this home sits on a spacious corner lot with plenty of parking and yard space. Enjoy both a large front porch and back porch, perfect for relaxing or entertaining. Inside, you’ll find original hardwood floors, an open floor plan, and lots of natural light throughout the home. The electrical panel box appears to have been updated at some point, adding to the home’s value and potential. Connected to city water and city sewer, this property is ideally located clos

$59,000

2 beds1 bath968 sq ft

210 S Center St, Perry, FL 32347

Open floor plan • Large front porch • Spacious corner lot

Property at 3103 S Byron Butler Pkwy, Perry, FL 32348, 4 beds, 1 bath

$159,999

4 beds1 bath1,827 sq ft

3103 S Byron Butler Pkwy, Perry, FL 32348

Property at 181 E Center St, Perry, FL 32348, 4 beds, 3 baths

$195,000

4 beds3 baths1,632 sq ft

181 E Center St, Perry, FL 32348

Property at 1080 Randolph St, Metcalf, GA 31792, 2 beds, 2 baths

$300,000

2 beds2 baths1,984 sq ft

1080 Randolph St, Metcalf, GA 31792

Property at 203 Hicks Rd, Thomasville, GA 31792, 1 bed, 1 bath

$300,000

1 bed1 bath792 sq ft

203 Hicks Rd, Thomasville, GA 31792

Property at 415 W Main St, Perry, FL 32347, 4 beds, 2 baths

$219,900

4 beds2 baths2,474 sq ft

415 W Main St, Perry, FL 32347

Property at 107 Pine Tree Rd, Perry, FL 32348, 3 beds, 2 baths

$325,000

3 beds2 baths2,818 sq ft

107 Pine Tree Rd, Perry, FL 32348

Property at 207 Cypress Rd, Perry, FL 32348, 3 beds, 2 baths

$39,900

3 beds2 baths1,356 sq ft

207 Cypress Rd, Perry, FL 32348

Property at 804 W Green St Unit N/A, Perry, FL 32347, 6 beds, 3 baths

$169,900

6 beds3 baths2,146 sq ft

804 W Green St Unit N/A, Perry, FL 32347

Property at 1103 N Jefferson St, Perry, FL 32347, 8 beds, 4 baths

$538,900

8 beds4 baths5,548 sq ft

1103 N Jefferson St, Perry, FL 32347

Property at 4285 NW Us 221, Greenville, FL, 2 beds, 1 bath

$40,000

2 beds1 bath1,050 sq ft

4285 NW Us 221, Greenville, FL

Property at 1534 SW Main St, Greenville, FL 32331, 4 beds, 1 bath

$269,000

4 beds1 bath2,862 sq ft

1534 SW Main St, Greenville, FL 32331

Property at 205 Cypress Rd, Perry, FL 32348, 3 beds, 1 bath

$175,000

3 beds1 bath1,493 sq ft

205 Cypress Rd, Perry, FL 32348

Property at 507 Plantation Rd, Perry, FL 32348, 3 beds, 2.5 baths

$273,999

3 beds2.5 baths2,036 sq ft

507 Plantation Rd, Perry, FL 32348

Property at 603 W Julia St, Perry, FL 32347, 3 beds, 2 baths

$130,000

3 beds2 baths1,412 sq ft

603 W Julia St, Perry, FL 32347

Vintage Homes for Sale in Jefferson County

There are currently 16 vintage homes for sale in Jefferson County at a median listing price of $385K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Jefferson County stay on the market for 118 days. This map is refreshed with the newest listings in Jefferson County every 15 minutes.

In the past month, 10 homes have been sold in Jefferson County. In addition to houses in Jefferson County, there were also 0 condos, 1 townhouse, and 1 multi-family unit for sale in Jefferson County last month. Find your dream home in Jefferson 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 Jefferson County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Jefferson County. If you're looking to sell your home in the Jefferson County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Jefferson 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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