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:
This striking Victorian home built in 1892 and located near downtown Monticello. The home features original hardwood pine floors, soaring 12-foot ceilings, a large bay window with bench seating (and storage) and several fireplaces. The master bathroom has been completely redone and complements the spacious master bedroom. The exterior of the home has a wraparound front deck, a rear screened porch, a spacious detached workshop with electricity and fully fenced grounds. The home will need renovation and repair, but it is a beauty!

$199,900

3 beds2.5 baths2,467 sq ft

490 E Palmer Mill Rd, Monticello, FL 32344

Bench seating • Victorian home • 12-foot ceilings

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Go Back in time in this traditional farmhouse nestled on 4.44 acres totally fence and cross fenced. Over 1110 sq ft of screened porch for entertaing, relaxing, or looking at the 20x30 Koi pond. Sparkling wood foors throughout create warmth to the spacious rooms. 9x32 central hallway, large living room, family room, and all bedrooms are oversized. 600 sq ft garage with loft and attached 1 car carport. New Generac whole house generator, doggie door opens to fenced in area, outdoor patio with seating and grill station.

$595,000

3 beds2.5 baths3,054 sq ft

79 Lakeside Rd, Monticello, FL 32344

Koi pond • Central hallway • Wood floors

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Charming 1955 Cottage in the Heart of Monticello, Fl. Welcome home to this cozy yet surprisingly spacious 3-bedroom 1.5 -bath cottage on beautiful Oak Lined Pearl Street. Just a short walk or golf cart ride to historic downtown Monticello. Features include original hardwood floors, new windows, updated electrical and a sunroom with brick paver flooring- perfect for relaxing with morning coffee. Roomy master suite features French doors leading to master bath, while the cozy den sits at the heart of the home. The 1/2 bath could easily be converted back to a full bath. Outside, you will find a large . 66 fenced lot along with storage shed with plenty of space for pets or gardening. Backyard i

$319,000

3 beds1.5 baths1,855 sq ft

950 E Pearl St, Monticello, FL 32344

Updated electrical • Large fenced lot • Storage shed

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Full of character, this spacious 1950s home offers 4 bedrooms and 3 full bathrooms on a generous 0.60-acre lot in the heart of Monticello. With over 2,200 square feet—including two bedrooms with ensuite baths—it also features flexible zoning for residential, business, or mixed use. The layout includes a cozy living room with a fireplace and an airy sunroom, perfect for an office or casual dining. Tongue-and-groove ceilings run throughout, with coffered details adding charm in the main living and dining areas. Updates include a 2019 roof and 2022 HVAC. French doors open to the cleared back yard with a wood deck—great for entertaining or gardening. A detached one-car garage/

$355,000

4 beds3 baths2,223 sq ft

155 E Seminole Ave, Monticello, FL 32344

Wood deck • Cleared back yard • Huge side yard

OPEN THU, 12PM TO 2PM

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Charming Traditional Brick Home with Spectacular Sunset Views on 1.5 Acres Experience classic Florida living with this charming, traditional 3,126-square-foot brick home, perfectly nestled on one of the highest elevations in Jefferson County. Enjoy a blend of vintage character and modern functionality in this beautifully detailed residence, offering an ideal setting for relaxation and entertaining while capturing gorgeous sunset views each day. Fresh paint has been applied throughout the house, excluding the laundry and mud room, giving the interior a clean, updated feel, and the home features beautiful hardwood floors throughout. A unique local fact: this is located in the only county in

$505,500

3 beds2.5 baths3,126 sq ft

1628 N Jefferson Hwy Hwy, Monticello, FL 32344

Functional carport • Entertainment deck • Florida room

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

$449,000

4 beds3 baths3,188 sq ft

930 E Pearl St, Monticello, FL 32344

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

$585,000

3 beds3 baths2,187 sq ft

515 E Palmer Mill Rd, Monticello, FL 32344

Property at 12447 Gamble Rd, Monticello, FL 32344, 2 beds, 2 baths

$169,000

2 beds2 baths1,440 sq ft

12447 Gamble Rd, Monticello, FL 32344

Property at 660 N Jefferson St, Monticello, FL 32344, 2 beds, 2 baths

$275,000

2 beds2 baths1,672 sq ft

660 N Jefferson St, Monticello, FL 32344

Property at 425 N Mulberry St, Monticello, FL 32344, 5 beds, 2 baths

$315,000

5 beds2 baths3,320 sq ft

425 N Mulberry St, Monticello, FL 32344

Property at 300 Cedar St, Monticello, FL 32344, 3 beds, 2 baths

$269,900

3 beds2 baths2,044 sq ft

300 Cedar St, Monticello, FL 32344

Property at 2436 N Jefferson, Monticello, FL 32344, 3 beds, 2 baths

$198,000

3 beds2 baths2,390 sq ft

2436 N Jefferson, Monticello, FL 32344

Property at 1515 Tennessee Ave, Monticello, FL 32344, 2 beds, 2 baths

$185,000

2 beds2 baths1,096 sq ft

1515 Tennessee Ave, Monticello, FL 32344

Property at 2664 A W Washington Hwy, Monticello, FL, 5 beds, 2 baths

$325,000

5 beds2 baths2,659 sq ft

2664 A W Washington Hwy, Monticello, FL

Property at 205 N Rhodes St, Monticello, FL 32344, 3 beds, 2 baths

$365,000

3 beds2 baths2,766 sq ft

205 N Rhodes St, Monticello, FL 32344

Property at 4618 E Capps, Lamont, FL 32336, 4 beds, 1 bath

$65,000

4 beds1 bath1,232 sq ft

4618 E Capps, Lamont, FL 32336

Property at 130 Simpson Ave, Monticello, FL 32344, 3 beds, 2 baths

$249,900

3 beds2 baths1,654 sq ft

130 Simpson Ave, Monticello, FL 32344

Property at 740 Kinsey Rd, Monticello, FL 32344, 3 beds, 1 bath

$1,125,000

3 beds1 bath1,146 sq ft

740 Kinsey Rd, Monticello, FL 32344

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

$240,000

3 beds3 baths1,617 sq ft

43 Depot St, Lamont, FL 32336

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ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Tiny house but with 3 Bedrooms and 3 Bathrooms. Yes you read that right. .. there are three BEAUTIFUL bathrooms. Easy to maintain city lot sized 40 ft. deep by 100 ft. wide. Located in the heart of Greenville, Florida this home is thoughtfully updated offering a delightful blend of old character and modern design. The brand new kitchen features beautiful cabinetry, sleek countertops, pendant lighting, all new appliances and a spacious island perfect for casual dining or entertaining. Two of the bathrooms are private ensuite retreats, while the third bathroom conveniently serves guests from the kitchen area. With a combination of shingle and metal roofing, its both practical and enduring. Co

$89,000

3 beds3 baths934 sq ft

409 SW Obadiah St, Greenville, FL 32331

Brand new kitchen • Thoughtfully updated • Heart of greenville

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
This beautifully remodeled home is located just minutes from everything the city of Perry has to offer! The 10-foot ceilings create a spacious and luxurious feel, and the hardwood floors add timeless charm. The kitchen offers generous counter space, ample cabinetry, and two stoves — perfect for cooking and entertaining. A versatile bonus space can easily serve as a third bedroom, second master, or entertainment room, giving this home incredible flexibility. Major updates include a roof installed in 2020, updated electrical and plumbing, and a 2016 hot water heater. A new pool pump has just been installed; the in-ground pool will still need refinishing, cleaning, and filling to reach i

$255,000

3 beds2 baths1,749 sq ft

608 Plantation Rd, Perry, FL 32348

In-ground pool • Ample cabinetry • Two stoves

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Step back in time with this charming 1901 historic 3 bedroom 2 bath home located near the heart of downtown Greenville, FL sitting on a 1/2 acre of land. Once the residence of the well-known Red Braswell, this property is full of rich character, local history, and endless potential. Nestled in a quiet, established neighborhood, this home offers a peaceful setting with convenient access to shops, and community events. The home needs some repairs, but is full of unique features and timeless appeal. This gem can be beautifully restored to its former glory — the possibilities are endless for the right owner ready to bring it back to life.

$54,000

3 beds1 bath1,096 sq ft

237 NW Leggett Ave, Greenville, FL 32331

Unique features • Heart of downtown • Timeless appeal

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Welcome to this historic charming gem that is a step back in time with modern comforts! Original hardwood floors throughout most of the home! This is more than a home-it's a piece of history! Walk into the foyer with your view of the beautiful hardwood floors in the living room flowing into the dining room. Designed for both everyday living and entertaining, the home features a dining room plus a large eat in kitchen and loads of historic character! The kitchen has the original farm sink and metal cabinet with new butcher block countertops. All 4 bedrooms are great sizes & feature wall reach-in closets. Both bathrooms are in excellent vintage condition! Huge bonus carriage house with

$259,000

4 beds2 baths2,474 sq ft

415 W Main St, Perry, FL 32347

Bonus carriage house • Original farm sink • 0.31 acre lot

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, FL:
Step into this beautifully decorated brick home boasting 4 bedrooms and 2 baths. This home is the definition of cozy and relaxing, with exposed beams and pine ceilings adding charming accent touches. The nicely sized kitchen, featuring stainless steel appliances, sets the tone for entertaining guests. Built in 1958, this brick home offers 1,612 sq. ft. of living space and sits on a 0.31-acre lot. Conveniently located close to the middle school, it provides ample room for the entire family. The fenced-in yard offers plenty of space for boat storage and a secure place for kids and pets to play. This home exudes southern charm with a warm, inviting atmosphere. With a brand new roof installed i

$195,000

4 beds2 baths1,612 sq ft

301 N Manila Ave, Perry, FL 32347

Pine ceilings • Brand new roof • Exposed beams

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, GA:
RARE OPPORTUNITY! This late 1800 early 1900 era home boast historic character with farmhouse details in every room. This twin gabled farmhouse perched on 9.41 acres of high and dry land is fantastic for a homestead. Two pastures are fenced and cross fenced for horses or livestock, a garden area is in place, and a chicken coop for fresh eggs. The handcrafted front doors welcome you into a home where history meets everyday living, with wide open spaces, warm wood tones, and character in every detail. The foyer leads to the staircase and central hall. Inside, there's room for everyone — 5 bedrooms and 3 baths, plus a dining room made for entertaining and a eat-in kitchen where homemade b

$495,000

5 beds3 baths2,819 sq ft

2156 County Rd. 78, Dixie, GA 31629

Farmhouse details • Garden area • Fenced pastures

Property at 515 N Quincy St, Perry, FL 32347, 5 beds, 2 baths

$289,000

5 beds2 baths2,309 sq ft

515 N Quincy St, Perry, FL 32347

Property at 611 W Green St, Perry, FL 32347, 2 beds, 2 baths

$169,000

2 beds2 baths2,194 sq ft

611 W Green St, Perry, FL 32347

Property at 802 N Quincy St, Perry, FL 32347, 2 beds, 2 baths

$195,000

2 beds2 baths1,312 sq ft

802 N Quincy St, Perry, FL 32347

Property at 1764 Dice Rd, Perry, FL 32348, 2 beds, 1 bath

$92,900

2 beds1 bath616 sq ft

1764 Dice Rd, Perry, FL 32348

Property at 1341 Us Highway 98 W, Perry, FL 32347, 3 beds, 1.5 baths

$90,000

3 beds1.5 baths1,100 sq ft

1341 Us Highway 98 W, Perry, FL 32347

Property at 1775 N Us 19 Hwy, Perry, FL 32347, 4 beds, 3 baths

$435,000

4 beds3 baths3,473 sq ft

1775 N Us 19 Hwy, Perry, FL 32347

Property at 117 Ridge Rd, Perry, FL 32348, 4 beds, 4 baths

$459,000

4 beds4 baths2,613 sq ft

117 Ridge Rd, Perry, FL 32348

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

$120,000

3 beds1 bath2,880 sq ft

317 N Orange St, Perry, FL 32347

Property at 305 W High St, Perry, FL 32347, 2 beds, 0.5 baths

$140,000

2 beds0.5 baths960 sq ft

305 W High St, Perry, FL 32347

Property at 1008 E Julia St, Perry, FL 32347, 4 beds, 2 baths

$175,000

4 beds2 baths1,431 sq ft

1008 E Julia St, Perry, FL 32347

Property at 13996 Godbold Rd, Tallahassee, FL 32309, 3 beds, 3 baths

$450,000

3 beds3 baths1,794 sq ft

13996 Godbold Rd, Tallahassee, FL 32309

Property at 315 W Green St, Perry, FL 32347, 3 beds, 1 bath

$205,000

3 beds1 bath2,746 sq ft

315 W Green St, Perry, FL 32347

Property at 1118 W Green St, Perry, FL, 5 beds, 2 baths

$250,000

5 beds2 baths2,815 sq ft

1118 W Green St, Perry, FL

Property at 1100 S Wilder St, Perry, FL 32348

$24,000

— beds— baths100 sq ft

1100 S Wilder St, Perry, FL 32348

Based on information submitted to the MLS GRID as of Wed Dec 03 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Jefferson County

There are currently 19 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 101 days. This map is refreshed with the newest listings in Jefferson County every 15 minutes.

In the past month, 7 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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