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

11 homes

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NEW 32 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Great opportunity to be in the lovely town of Monticello off of Pearl Street. Acre lot & Concrete swimming pool with this single story home. Large rooms, hardwood floors throughout much of the house, updated kitchen cabinetry, large detached garage. House has been cleaned up & some fresh painting done but does need work and is priced accordingly. Being sold AS-IS w/ right to inspect.

$299,900

3 beds2 baths2,583 sq ft

515 Sunset Dr, Monticello, FL 32344

Acre lot • Hardwood floors • Detached garage

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

$108,000

5 beds2 baths2,612 sq ft

1150 Sage St, Monticello, FL 32344

0.63 acre lot • Built 1914 • Listed 18 days

ABOUT THIS HOME
Vintage Home for sale in Jefferson 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 Jefferson 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 Jefferson County, FL:
For generations, this beautifully maintained, one-family owned brick home has been a place where holidays were celebrated, children were raised, and life's everyday moments became treasured memories. Today, with only one family member remaining, the home has simply become more space than one person needs. Rather than seeing it sit too quietly, she hopes to pass it on to another family who will fill its rooms with laughter, traditions, and memories of their own. It is a home that has been deeply loved, carefully preserved, and is ready for its next chapter. Situated on 1.5 peaceful acres along North Jefferson Highway, this neo-classic 3-bedroom, 2 and a 1/2 bath home offers 3127 square feet

$398,900

3 beds2.5 baths3,127 sq ft

1628 N Jefferson Hwy, Monticello, FL 32344

Original oak floors • Screened porch • Wide baseboards

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 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 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 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 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 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

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ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Home is being offered AS-IS.

$59,900

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:
Well-cared-for brick home on 7.04 acres, offering 3 bedrooms, 2 full bathrooms, and 1659 square feet of living space. This one owner home since 1995 has been lovingly maintained and offers character and durability of a 1960's brick home with important recent updates, including a new roof in 2024 and new A/C in 2023. The property also features a two-car garage with two workbenches that will remain, providing excellent space for projects or hobbies. A rare opportunity to enjoy a well-maintained home with plenty of land and room to make it your own. Room dimensions are approximate. Acreage is partially cleared and partially wooded.

$299,500

3 beds2 baths1,659 sq ft

490 Roberts Aman Rd E, Perry, FL 32347

Brick home • New a/c • 7.04 acres

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
This Classic 1944 Brick Home sits proudly on 1 acre and has been the heart of several generations. Filled with memories, laughter, and decades of family gatherings, it’s now ready to welcome its next chapter — and the next family to make new memories of their own. Enjoy meaningful updates including a brand-new roof (June 2025), updated HVAC (2023), new French-door refrigerator (2024), and a complete electrical overhaul (2025). The original three-bedroom layout has been thoughtfully reimagined into a private primary suite with sitting area and en-suite, creating a peaceful retreat within the home. The converted back porch now serves as a cozy den with a wall-mounted electric fire

$185,000

3 beds2 baths2,123 sq ft

1946 N Us 221, Perry, FL 32347

Brand new roof • Updated hvac • 1.02 acre lot

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Located in downtown Perry, close to virtually everything. Nice and need corner lot. Move in ready.

$134,500

2 beds1 bath1,056 sq ft

701 E Morgan Ave, Perry, FL 32347

Move in ready • Corner lot • 0.25 acre lot

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Step into timeless Southern elegance in this beautifully restored historic home where original character and modern luxury blend seamlessly. From the moment you enter, you'll be captivated by the grand foyer, soaring ceilings, rich original woodwork, stunning staircase, and beautifully preserved hardwood floors throughout. The spacious living areas showcase classic architectural details, including a charming fireplace, and abundant natural light. The thoughtfully updated kitchen offers modern conveniences while honoring the home's historic charm, featuring cabinetry, premium finishes, two refrigerators, two dishwashers, and generous workspace designed for both everyday living and large-scal

$538,900

8 beds4 baths5,548 sq ft

1103 N Jefferson St, Perry, FL 32347

Grand foyer • Charming fireplace • Soaring ceilings

ABOUT THIS HOME
Vintage Home for sale in Jefferson 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

Property at 11343 Eva Ln, Tallahassee, FL 32317, 3 beds, 1 bath

$250,000

3 beds1 bath1,948 sq ft

11343 Eva Ln, Tallahassee, FL 32317

Property at 1534 SW Main St, Greenville, FL 32331, 4 beds, 2 baths

$299,000

4 beds2 baths2,862 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 212 Cypress Rd, Perry, FL 32348, 3 beds, 1 bath

$198,000

3 beds1 bath955 sq ft

212 Cypress Rd, Perry, FL 32348

Property at 3586 Old Dixie Hwy, Perry, FL 32348, 3 beds, 2 baths

$289,000

3 beds2 baths1,675 sq ft

3586 Old Dixie Hwy, Perry, FL 32348

Property at 804 N Calhoun St, Perry, FL 32347, 3 beds, 2 baths

$75,000

3 beds2 baths1,748 sq ft

804 N Calhoun St, Perry, FL 32347

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

$283,999

3 beds2.5 baths2,036 sq ft

507 Plantation Rd, Perry, FL 32348

Property at 512 Wilder St, Perry, FL 32347, 3 beds, 1 bath

$165,000

3 beds1 bath1,337 sq ft

512 Wilder St, Perry, FL 32347

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 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

Property at 515 N Quincy St, Perry, FL 32347, 5 beds, 3.5 baths

$249,000

5 beds3.5 baths2,309 sq ft

515 N Quincy St, Perry, FL 32347

Property at 4890 Chaires Cross Rd, Tallahassee, FL 32317, 5 beds, 2 baths

$359,900

5 beds2 baths2,652 sq ft

4890 Chaires Cross Rd, Tallahassee, FL 32317

Property at 317 N Orange St, Perry, FL 32347, 3 beds, 1 bath

$89,900

3 beds1 bath2,880 sq ft

317 N Orange St, Perry, FL 32347

Property at 210 S Center St, Perry, FL 32347, 2 beds, 1 bath

$69,500

2 beds1 bath968 sq ft

210 S Center St, Perry, FL 32347

Vintage Homes for Sale in Jefferson County

There are currently 11 vintage homes for sale in Jefferson County at a median listing price of $425K. 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 102 days. This map is refreshed with the newest listings in Jefferson County every 15 minutes.

In the past month, 12 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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