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:
Charming country home situated on a spacious lot in Henderson! This inviting property offers approximately 1,526 square feet of living space and features a welcoming covered front porch, metal roof, and peaceful setting surrounded by mature trees. The home provides plenty of potential for an owner-occupant or investor looking to make it their own. Conveniently located near local amenities while offering a more private, rural atmosphere. Don't miss the opportunity to see all this property has to offer!

$125,000

3 beds1.5 baths1,526 sq ft

1341 Old Jacks Creek Rd, Henderson, TN 38340

Covered front porch • Metal roof • Mature trees

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
4 bedroom 2 bath Brick home on 57.6 acres that offers everything. This 2774 Sq Ft home features Luxury Vinyl floors and a very spacious Living, Dinning and Kitchen area. Other features include a single attach garage and a separate unattached storage and shop. Great place to live and the 57.6 acres offers a great place for hunting and recreation or a good hobby farm. The land also has a Creek that runs year-round.

$435,000

4 beds2 baths— sq ft

320 Rabbit Ranch Rd, Henderson, TN 38340

Year-round creek • Brick home • Luxury vinyl floors

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Welcome home! This 3-bedroom 1-bath property is a great starter home or investment property. Enjoy the convenience of being in the city limits, with shopping and everyday amenities nearby and all that Henderson has to offer right around the corner.

$99,900

3 beds1 bath816 sq ft

234 Sanford Cv, Henderson, TN 38340

0.3 acre lot • 2 parking spots • Built 1952

$109,900

3 beds1 bath756 sq ft

221 Sanford Cv, Henderson, TN 38340

0.34 acre lot • 4 parking spots • Built 1952

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
GREAT OLDER HOME WITH A LOT OF CHARACTER, THIS WONDERFUL 2 BR. , 1 BATH HOME IS GREAT FOR A YOUNG COUPLE STARTING OUT OR A COUPLE THAT WANT TO DOWNSIZE, COVERED BACK DECK (GREAT FOR EARLY MORNING COFFEE AND WATCHING THE ANIMALS, OR FRONT OF HOUSE HAS A COVERED ENCLOSED PORCH, PLUS A GREAT SUNROOM THAT HAS A WINDOW UNIT, (SO MANY CHOICES, HARDWOOD FLOORS THROUGH, BATHROOM HAS HANDICAP RAILS ON WALL AND IN TUB, LARGE DETACHED GARAGE (WALK -WAY FROM HOUSE TO GARAGE IN BACK (WASHER AND DRYER HOOKUPS IN THE GARAGE AREA, STORAGE BUILDING OUT BACK AND A GREAT GARDEN SPOT . EXTERNAL STORM SHELTER, THIS IS A MUST SEE .

$164,500

2 beds1 bath720 sq ft

7475 E State Route 100, Jacks Creek, TN 38347

Storage building • Covered back deck • Great sunroom

Property at 450 North Ave, Henderson, TN 38340, 5 beds, 4 baths

$349,900

5 beds4 baths3,631 sq ft

450 North Ave, Henderson, TN 38340

Property at 432 Galbraith Ave, Henderson, TN 38340, 2 beds, 1 bath

$191,500

2 beds1 bath1,082 sq ft

432 Galbraith 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 130 Simmons St, Henderson, TN 38340, 4 beds, 2 baths

$244,900

4 beds2 baths1,456 sq ft

130 Simmons St, Henderson, TN 38340

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

$330,000

3 beds2 baths1,985 sq ft

521 Crook Ave, 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 1295 Mayfield Rd, Henderson, TN 38340, 3 beds, 1.5 baths

$157,400

3 beds1.5 baths960 sq ft

1295 Mayfield Rd, Henderson, TN 38340

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

$55,000

2 beds1 bath1,864 sq ft

2160 Jones Rd, Luray, TN 38352

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

$189,900

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

$375,000

Land60.00 acres (lot)

795 Hill Ave, Henderson, TN 38340

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NEW 10 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Well-Maintained Jackson Home with Large Covered Back Deck Welcome to 20 Waverly Dr. in Jackson, TN! Located on a quiet back street, this spacious 3-bedroom home offers approximately 1,875 square feet of living space and a generous lot with plenty of room to enjoy. One of the home's standout features is the large covered back deck, providing a wonderful space for morning coffee, outdoor dining, entertaining, or relaxing in the shade. The property also features new fencing and gates along the front area, adding both privacy and attractive curb appeal. Several important updates provide additional peace of mind, including a 2-year-old HVAC system, a 1-year-old water heater, and a roof that was

$235,000

3 beds1.5 baths1,875 sq ft

20 Waverly Dr, Jackson, TN 38301

Close to hospitals • 0.25 acre lot • 2 parking spots

NEW 15 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Welcome to 241 N Maple St in Adamsville! This charming 2-bedroom, 2-bath home, originally built in 1942, was fully renovated in 2006 with extensive updates, including the roof, plumbing, windows, and electrical system. The home offers a comfortable blend of classic character and modern functionality. The kitchen features beautiful wood cabinetry with soft-close hinges and an inviting eat-in dining area, providing a functional space for everyday living and entertaining. A central HVAC system provides heating and cooling, while ceiling fans throughout add comfort. Accessibility features include an accessible front porch with a ramp and an accessible bedroom, making this home a great option fo

$176,950

2 beds2 baths1,482 sq ft

241 N Maple St, Adamsville, TN 38310

Fully renovated • Eat-in dining area • Central hvac system

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Nestled just minutes from the amenities of Downtown and Jackson General, this Midtown gem is truly unlike any other in the area. Stripped down to its bones and completely reimagined, this home has been thoughtfully renovated, with much of the home new or updated in 2017 and beyond. 140 Hawthorne St. is exquisitely prepared for its next owner—you must see it to believe it! Upgrades and improvements include new plumbing from the street with PEX piping throughout the home, updated electrical wiring, smart lighting, recessed LED lighting, insulated walls, fresh sheetrock, newer windows, updated flooring, custom cabinetry, solid-core doors, a chef's kitchen with KitchenAid appliances, gra

$490,000

5 beds4 baths2,920 sq ft

140 Hawthorne St, Jackson, TN 38301

Custom cabinetry • New plumbing • Insulated walls

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
Ranch style brick with 2.11 acres on Hwy 45 North Bethel Springs. Interior has 1646 heated sq feet with large country kitchen that includes refrigerator, cooktop, built in oven & dishwasher. Lots of cabinets & dining area. Formal living room & den. Two large bedrooms and 1 bath. Spacious laundry & storage room includes washer & dryer. Mostly original hardwoods. Metal roof. Front porch and carport that can be used as covered patio. Convenient to house is a 23z27 detached garage. Nice, big yard with plenty room for a garden. Location convenient to Selmer & Henderson with easy access to Jackson or Corinth, MS. Well kept home in great location.

$210,000

2 beds1 bath— sq ft

5738 Hwy 45 Hwy N, Bethel Springs, TN 38315

Big yard • Spacious laundry • Ranch style brick

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
This charming 4 bedroom, 2 bath brick home offers plenty of space and potential. This home offers original hardwood floors, a breakfast room, plenty of cabinets space and more.

$199,900

4 beds2 baths1,517 sq ft

43 Bemis Ln, Jackson, TN 38301

Breakfast room • 0.3 acre lot • 2 garage spots

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in Chester County, TN:
One of our favorite LANA homes is now on the market. Our friends have moved out of state, and we are sad, but this home is fabulous and you need to see it. We think you will love it. This large beautiful brick home boasts 5 bedrooms and 3 full baths. It is set up for a large family, or for someone who loves to have company and entertain! Located on the corner of beautiful Walnut Street and Lambuth Boulevard, the location is ideal for midtown living. LANA is a wonderful neighborhood, where neighbors know each other and enjoy the eclectic mix of homes and people. The rooms in this home are spacious with a perfect layout for large gatherings. The kitchen has been completely renovated with all

$449,900

5 beds3 baths3,511 sq ft

452 Walnut St, Jackson, TN 38301

Corner location • Laundry room • Renovated kitchen

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 385 Bolivar Hwy, Jackson, TN 38301, 2 beds, 1 bath

$219,700

2 beds1 bath1,293 sq ft

385 Bolivar Hwy, Jackson, TN 38301

Property at 176 Wisdom St, Jackson, TN 38301, 3 beds, 2 baths

$214,900

3 beds2 baths1,636 sq ft

176 Wisdom St, Jackson, TN 38301

Property at 5 & 7 Judson St Unit 5 & 7, Jackson, TN 38301, 9 baths

$239,900

— beds9 baths2,559 sq ft

5 & 7 Judson St Unit 5 & 7, Jackson, TN 38301

Property at 277 Good Hope Church Rd, Adamsville, TN 38310, 3 beds, 2 baths

$269,900

3 beds2 baths2,170 sq ft

277 Good Hope Church Rd, Adamsville, TN 38310

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 4 Farwell St, Jackson, TN 38301, 3 beds, 2 baths

$199,900

3 beds2 baths1,450 sq ft

4 Farwell St, Jackson, TN 38301

Property at 201 Fairgrounds St N, Jackson, TN 38301, 4 beds, 3 baths

$174,900

4 beds3 baths2,672 sq ft

201 Fairgrounds St N, Jackson, TN 38301

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 5225 Tn-22 Alt, Lexington, TN 38351, 3 beds, 2 baths

$234,900

3 beds2 baths1,296 sq ft

5225 Tn-22 Alt, Lexington, TN 38351

Property at 424 Lambuth Blvd, Jackson, TN 38301, 3 beds, 2 baths

$80,000

3 beds2 baths1,560 sq ft

424 Lambuth Blvd, Jackson, TN 38301

Property at 319 Westwood Ave, Jackson, TN 38301, 4 beds, 2.5 baths

$289,900

4 beds2.5 baths2,271 sq ft

319 Westwood Ave, Jackson, TN 38301

Property at 1907 Elmer Cox Rd, Bethel Springs, TN 38315, 2 beds, 1 bath

$114,000

2 beds1 bath738 sq ft

1907 Elmer Cox Rd, Bethel Springs, TN 38315

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 42 North Ave, Jackson, TN 38301, 2 beds, 1 bath

$163,000

2 beds1 bath1,082 sq ft

42 North Ave, Jackson, TN 38301

Property at 228 Talbot St, Jackson, TN 38301, 3 beds, 3 baths

$265,000

3 beds3 baths1,197 sq ft

228 Talbot St, Jackson, TN 38301

Property at 75 64 Hwy, Adamsville, TN 38310, 4 beds, 2 baths

$349,900

4 beds2 baths— sq ft

75 64 Hwy, Adamsville, TN 38310

Property at Rose Creek Rd, Selmer, TN 38375

$135,000

Land30.52 acres (lot)

Rose Creek Rd, Selmer, TN 38375

Vintage Homes for Sale in Chester County

There are currently 15 vintage homes for sale in Chester County at a median listing price of $245K. 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 56 days. This map is refreshed with the newest listings in Chester County every 15 minutes.

In the past month, 19 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 Tue Sep 01 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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