Vintage homes for sale & real estate in Chester County, TN

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ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
WANT TO BE IN TOWN BUT NEED A HOME WITH GOOD SQ. FT, AND PRICED GREAT. THEN THIS COULD BE THE ONE. THIS IS THE CUTEST HOUSE. COULD HAVE 4 BEDROOMS, 2 BATHS, OFFICE, EXTRA AREA, GREAT LIVING ROOM, DINING ROOM, AND A GREAT KITCHEN. LAUNDRY ROOM IS A GOOD SIZE, NEW FLOORING AND PAINT AND GREAT WALK-IN SHOWER IN MASTER BATHROOM, EXTERNAL STORM SHELTER, DETACHED GARAGE/SMALL WORKSHOP, AND LARGE LOT, ( large hole in backyard where owners Son started to put a small pond in but never finished) WITHIN WALKIN DISTANCE TO STORES, DOWNTOWN, CHURCHES ETC. CALL FOR A GREAT SHOWING ON THIS ONE. SOME FOUNDATION ISSUE ON SOUTH WALL OF HOUSE

$164,500

4 beds2 baths1,832 sq ft

323 N Church Ave, Henderson, TN 38340

4 parking spots • Built 1940 • Listed 15 days

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Charm, Character & Space Right in Town! Updated 3BR Home on 0.38 Acres Welcome home to this charming home with timeless character! Situated on a rare, generous 0.38-acre city lot, this beautifully updated 3-bedroom, 1-bathroom home offers the peace of a large yard with all the conveniences of living right in town. Standout Interior Features: • Warm & Inviting Living Spaces: Fall in love with the stunning, rich hardwood floors that flow through the main living areas, offering durability and classic style. • Stunning Wood Ceilings: The gorgeous character-rich wood ceilings add incredible warmth, architectural detail, and unmatched charm to the home. • Dedicated La

$189,900

3 beds1 bath944 sq ft

301 Fourth St, Henderson, TN 38340

Attached carport • Wood ceilings • Storage shed

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Four-bedroom, 1.5-bath home with an oversized living room, separate den, and huge laundry room. Built back when wood was the real deal, this solid, well-built home features original hardwood floors, tongue-and-groove details, and beautiful woodwork throughout. The substantial construction gives the home a remarkably quiet feel indoors. With generous living spaces and timeless character, this home is ready for its next chapter. Text or call me to show you your home, investment property, or the place to start your dream business in.

$234,900

4 beds1.5 baths2,351 sq ft

563 E Main St, Henderson, TN 38340

Separate den • Huge laundry room • 0.69 acre lot

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
This two-bedroom, one-bath home has been completely remodeled and is ready to move into. Inside, you'll find fresh updates throughout, including new kitchen cabinets, new flooring, new light fixtures, new faucets, and new paint, along with much more. Outside, the home features a new roof and new vinyl siding, giving you great curb appeal and added peace of mind. Make this completely remodeled home yours—schedule a showing today!

$99,900

2 beds1 bath725 sq ft

405 Baughn St, Henderson, TN 38340

Completely remodeled • New faucets • New flooring

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
LOCATION, LOCATION, LOOKING FOR A HOUSE WITHIN WALKING DISTANCE TO DOWNTOWN, FHU, ETC, THEN THIS COULD BE THE ONE FOR YOU. 1304 HEATED SQUARE FEET, THIS HOME HAS 3 BEDROOMS, /2 BATHS, KITCHEN, DINING ROOM, OFFICE, SMALL COVERED BACK PORCH, LARGE PATIO AND A GREAT LOT, THE MASTER BEDROOM IS A GREAT SIZE, WITH WASHER/DRYER CONNECTION LOCATED IN THE MASTER BATHROOM. NEW DISHWASHER, NEW STOVE, NEW REFRIGERATOR, SOME NEW FLOORING, (CARPET IN MASTER B/R NEW), HARDWOOD FLOORS REDONE, TILE, NEW PAINTING INSIDE AND NEW PAINT OUTSIDE, ROOF (METAL) - 9 YEARS OLD, CH/A - 8 YEARS OLD, NEW VANITY IN HALL BATHROOM. CALL FOR A SHOWING ON THIS PROPERTY. WONDERFUL FUTURE HOME FOR YOU AND YOUR FAMILY

$199,999

3 beds2 baths1,304 sq ft

128 E 6th St, Henderson, TN 38340

New stove • Large patio • New refrigerator

Property at 130 N State Route 22a Hwy N, Jacks Creek, TN 38347, 3 beds, 2 baths

$245,000

3 beds2 baths1,648 sq ft

130 N State Route 22a Hwy N, Jacks Creek, TN 38347

Property at 221 Sanford Cv, Henderson, TN 38340, 3 beds, 1 bath

$99,500

3 beds1 bath756 sq ft

221 Sanford Cv, Henderson, TN 38340

Property at 234 Sanford Cv, Henderson, TN 38340, 3 beds, 1 bath

$89,900

3 beds1 bath816 sq ft

234 Sanford Cv, Henderson, TN 38340

Property at 521 Crook Ave, Henderson, TN 38340, 3 beds, 2 baths

$318,700

3 beds2 baths1,985 sq ft

521 Crook Ave, Henderson, TN 38340

Property at 137 Fourth St, Henderson, TN 38340, 3 beds, 2 baths

$214,900

3 beds2 baths1,356 sq ft

137 Fourth St, Henderson, TN 38340

Property at 241 Crook Ave, Henderson, TN 38340, 4 beds, 2 baths

$226,250

4 beds2 baths1,949 sq ft

241 Crook Ave, Henderson, TN 38340

Property at 2160 Jones Rd, Luray, TN 38352, 2 beds, 1 bath

$45,000

2 beds1 bath1,864 sq ft

2160 Jones Rd, Luray, TN 38352

Property at 454 White Ave, Henderson, TN 38340, 3 beds, 1 bath

$177,900

3 beds1 bath1,272 sq ft

454 White Ave, Henderson, TN 38340

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 795 Hill Ave, Henderson, TN 38340, 2 baths

$375,000

Land60.00 acres (lot)

795 Hill Ave, Henderson, TN 38340

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NEW 22 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Step back in time with this charming historic home full of character and potential! Built in 1906, this spacious home offers 4-5 bedrooms, a bonus room, two kitchens, three fireplaces, and a sunroom. With its inviting front porch, beautiful architectural charm, and unique features throughout, this property is ready for someone to bring it back to life. Additional highlights include two storage buildings and electrical wiring upgraded in 2005. While the home needs some TLC, it offers a wonderful opportunity to restore its historic charm while making it your own. * * Bring your vision and make this one-of-a-kind property shine again! * * . Enjoy the added convenience of a brand-new childre

$97,900

4 beds4 baths2,792 sq ft

249 S Main St, Lexington, TN 38351

Two kitchens • Three fireplaces • Front porch

NEW 31 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
INVESTOR ALERT! TWO INCOME-PRODUCING HOMES ON ONE PARCEL! Located in the heart of Jackson, just minutes from Jackson General Hospital and downtown! The main home is a charming 2-bedroom, 1-bath long-term rental featuring original hardwood floors, French doors, and an updated kitchen. The second home is a fully furnished 1-bedroom, 1-bath currently operating as a successful Airbnb. Both homes underwent extensive renovations in 2021/2022, with new flooring added to the Airbnb in 2026. With two established income streams and a strong rental history, this property is a great opportunity to expand your investment portfolio! Contact the Listing Agent for rental income details.

$255,000

2 beds1 bath1,611 sq ft

114 Roland Ave, Jackson, TN 38301

Updated kitchen • 7,405 sq ft lot • 4 parking spots

NEW 35 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Jackson Renters: DATE THE RATE AND MARRY THE HOME! Call to schedule your showing today for this 2 bedroom/1 bath home. This home has a new roof, tile countertops, Stainless steel double sink, tile floors in the kitchen & bathroom, beautiful hardwood floors in bedrooms/living room. The living room has built in bookcases and a nice wood burning stove. This home has a very large backyard for those family get-togethers and will great for grilling-out on the weekends! Why rent when you can own your own home! Close to downtown! Call Jimmy Bizzell today to schedule your private showing: 731.443.6911.

$129,000

2 beds1 bath1,118 sq ft

28 Mitchell St, Jackson, TN 38301

Tile floors • Built in bookcases • Tile countertops

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
INVESTMENT OPPORTUNITY! Nine-property, 10-unit residential portfolio offered exclusively as one package for a total asking price of $750,000. The portfolio consists of one duplex and eight single-family residences located throughout Jackson and the surrounding area. This offering is intended for investors seeking to acquire multiple residential rental properties in a single transaction. The entire portfolio must be purchased together. Individual properties are not being offered for separate sale. Several properties offer existing rental income, providing an opportunity to expand an investment portfolio. For additional properties included and further rental income / occupancy information, pl

$80,000

2 beds1 bath763 sq ft

32 Ingram St, Jackson, TN 38301

8,750 sq ft lot • 2 parking spots • Built 1940

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
INVESTMENT OPPORTUNITY! Nine-property, 10-unit residential portfolio offered exclusively as one package for a total asking price of $750,000. The portfolio consists of one duplex and eight single-family residences located throughout Jackson and the surrounding area. This offering is intended for investors seeking to acquire multiple residential rental properties in a single transaction. The entire portfolio must be purchased together. Individual properties are not being offered for separate sale. Several properties offer existing rental income, providing an opportunity to expand an investment portfolio. For additional properties included and further rental income / occupancy information, pl

$80,000

2 beds1 bath972 sq ft

123 Craig St, Jackson, TN 38301

8,415 sq ft lot • 2 parking spots • Built 1950

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
INVESTMENT OPPORTUNITY! Nine-property, 10-unit residential portfolio offered exclusively as one package for a total asking price of $750,000. The portfolio consists of one duplex and eight single-family residences located throughout Jackson and the surrounding area. This offering is intended for investors seeking to acquire multiple residential rental properties in a single transaction. The entire portfolio must be purchased together. Individual properties are not being offered for separate sale. Several properties offer existing rental income, providing an opportunity to expand an investment portfolio. For additional properties included and further rental income / occupancy information, pl

$80,000

2 beds1 bath804 sq ft

105 4th St, Jackson, TN 38301

8,550 sq ft lot • 2 parking spots • Built 1911

Property at 112 4th St, Jackson, TN 38301, 1 bed, 1 bath

$80,000

1 bed1 bath728 sq ft

112 4th St, Jackson, TN 38301

Property at 110 Garneal St, Jackson, TN 38301, 2 beds, 1 bath

$80,000

2 beds1 bath975 sq ft

110 Garneal St, Jackson, TN 38301

Property at 707 N Hays Ave, Jackson, TN 38301, 3 beds, 1 bath

$80,000

3 beds1 bath1,280 sq ft

707 N Hays Ave, Jackson, TN 38301

Property at 1485-1487 N Royal St, Jackson, TN 38301, 4 beds, 2 baths

$80,000

4 beds2 baths1,542 sq ft

1485-1487 N Royal St, Jackson, TN 38301

Property at 25 Monroe Ave, Jackson, TN 38301, 2 beds, 1 bath

$172,500

2 beds1 bath1,200 sq ft

25 Monroe Ave, Jackson, TN 38301

Property at 209 Bailey St, Lexington, TN 38351, 2 beds, 1 bath

$60,000

2 beds1 bath520 sq ft

209 Bailey St, Lexington, TN 38351

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 109 Weir St, Jackson, TN 38301, 2 beds, 1 bath

$120,000

2 beds1 bath1,198 sq ft

109 Weir St, Jackson, TN 38301

Property at 82 Morton Package St, Jackson, TN 38301, 1 bath

$228,000

— beds1 bath1,720 sq ft

82 Morton Package St, Jackson, TN 38301

Property at 234 Linden St, Jackson, TN 38301, 4 beds, 3 baths

$314,900

4 beds3 baths— sq ft

234 Linden St, Jackson, TN 38301

Property at 1011 N Highland Ave, Jackson, TN 38301, 3 beds, 2.5 baths

$219,500

3 beds2.5 baths2,139 sq ft

1011 N Highland Ave, Jackson, TN 38301

Property at 1120 Campbell St, Jackson, TN 38301, 3 beds, 2 baths

$229,900

3 beds2 baths1,535 sq ft

1120 Campbell St, Jackson, TN 38301

Property at 41 Webber St, Jackson, TN 38301, 2 beds, 1 bath

$69,900

2 beds1 bath1,186 sq ft

41 Webber St, Jackson, TN 38301

Property at 1335 Hwy 64, Adamsville, TN 38310, 4 beds, 2 baths

$369,000

4 beds2 baths2,400 sq ft

1335 Hwy 64, Adamsville, TN 38310

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 1335 64 Hwy, Adamsville, TN 38310, 4 beds, 2 baths

$369,000

4 beds2 baths— sq ft

1335 64 Hwy, Adamsville, TN 38310

Vintage Homes for Sale in Chester County

There are currently 14 vintage homes for sale in Chester County at a median listing price of $257K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chester County stay on the market for 61 days. This map is refreshed with the newest listings in Chester County every 15 minutes.

In the past month, 12 homes have been sold in Chester County. In addition to houses in Chester County, there were also 0 condos, 1 townhouse, and 1 multi-family unit for sale in Chester County last month. Find your dream home in Chester 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 Chester County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chester County. If you're looking to sell your home in the Chester County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chester 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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Based on information submitted to the MLS GRID as of Sat Oct 17 2026. 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.

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