Chester County Real Estate for Sale

Living in Chester County

Life in Chester County is characterized by a peaceful, tight-knit small-town charm with sparse suburban appeal. Residents enjoy a low cost of living, no state income tax, and highly rated public schools, making it an ideal, affordable haven for first-time homebuyers, families, and retirees alike.

Locals love the abundant outdoor recreation centered around Chickasaw State Park, which features a 1,400-acre forest, Lake Placid, and miles of scenic trails. While providing a quiet country lifestyle with little to no crime, the county seat of Henderson is conveniently located just 18 miles south of Jackson, giving residents easy access to larger retail and dining options.

See what your Chester County home is worth

Get a real number for your Chester County home, farm, or land

Talk with Tennessee Home & Farm Real Estate

Tennessee Home & Farm Real Estate pairs valuation technology with practical Chester County pricing guidance, seller preparation advice, land context, and listing strategy based on the property details buyers evaluate in Chester County. Use the estimate as a starting point, then talk with a THFRE agent about condition, timing, acreage, access, utilities, recent comparable sales, and how your property compares with similar Tennessee homes, farms, or land.

Chester County real estate market stats — last 6 months

$224,000Median list price
$3,400Median price per acre
17Active listings
47Median days on market

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Talk with the top Chester County real estate agents

Tennessee Home & Farm Real Estate helps clients with clear communication, local knowledge, seller preparation, negotiation support, land-aware diligence, and smoother closings. For Chester County, that means practical help with pricing, preparation, negotiations, inspections, and closing details. Contact THFRE about Chester County.

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Chester County real estate FAQs

Price is just the starting point. In Chester County, buyers should also weigh road access, well and septic condition, survey status, fencing, timber rights, and any deed restrictions. For homes in town, focus on condition and financing fit. For rural tracts, the due diligence list gets longer fast. A local agent who knows the difference between a clean country home and a complicated rural parcel can save you real money and time.

Buyers should have financing reviewed, know their preferred property type, and understand the due-diligence items that matter in Chester County. Before writing an offer, compare condition, acreage, access, utilities, inspection needs, title questions, and comparable sales. That preparation helps you choose terms that fit the property without skipping important safeguards.

We work with buyers and sellers across the full range of Chester County property: in-town homes, country homes with acreage, working farms, recreational tracts, hunting land, and raw acreage that needs a closer look at utilities, access, and use. If the property has a rural component, we bring the local knowledge to help you evaluate it honestly rather than just close a transaction.

Sellers should address obvious repairs, clean up the home and exterior, gather records for major systems, and make sure acreage, utilities, access, and improvements are clearly documented. Pricing should be based on comparable sales, condition, setting, and property-specific features rather than broad averages. Good preparation helps buyers evaluate the property with fewer surprises.

That depends on the specific parcel and your lender. Rural land in Chester County may qualify for USDA, farm credit, or conventional land loans, but lenders will look hard at legal access, survey, and intended use before approving anything. Raw land without road frontage or utilities is harder to finance than a tract with a well, septic, and a clear survey. Talk to a lender familiar with rural Tennessee property before you make an offer.

140 Lake Shore Lane, Henderson $3,499,000

Nestled on 51 pristine acres, this sprawling 8,264 square-foot estate offers unparalleled luxury and privacy. A true masterpiece of design and craftsmanship, the home fea...

5 Beds
8 Baths
3529035 MLS
ACTIVE Status
51 Acres
38340 Zip Code

80 Proctor Rd, Henderson $899,900

Discover a gorgeous 108 acres offering the perfect blend of open pasture, water, woods, and functionality. The property features cross fencing with seperated pastures, po...

3506115 MLS
ACTIVE Status
108 Acres
38340 Zip Code

Center Point Rd S, Reagan $99,900

Escape to the peace and beauty of rural Tennessee with this 9.05-acre surveyed property in Reagan. Featuring a blend of wooded terrain, rolling slopes, and approximately ...

3333534 MLS
ACTIVE Status
9.05 Acres
38368 Zip Code

460 Kendyl Cv, Henderson $209,000 ▼

Unlock the Potential at 460 Kendyl Cove, Henderson, TN! Bring your vision and transform this 3-bedroom, 2-bath home offering 1,471 square feet on a spacious half-acre lo...

3 Beds
2 Baths
3298153 MLS
ACTIVE Status
0.44 Acres
38340 Zip Code

Arl Bailey Road, Finger $159,900 ▼

Located entirely in Chester County, TN, this approximately 50.1 acre parcel was surveyed in 2021 and features roughly a quarter mile of road frontage with power and fiber...

3247974 MLS
ACTIVE Status
50.1 Acres
38334 Zip Code

454 White Ave, Henderson $189,900 ▼

Adorable 3 br Brick home sitting on large city lot with lots of character, Built ins and Mantle in living room, Hardwood floors throughout, Newly remodeled Kitchen with ...

3 Beds
1 Baths
3230112 MLS
ACTIVE Status
0.5 Acres
38340 Zip Code

100 Mary Kate Ln, Henderson $410,000 ▼

Located in an established and desirable Henderson neighborhood, this spacious home offers the perfect blend of suburban comfort, functional living, and sustainable, farm-...

5 Beds
2 Baths
3208441 MLS
ACTIVE Status
1 Acres
38340 Zip Code

S Hwy 22A, Enville $480,000

Don’t miss this rare opportunity to own 143.34 unrestricted acres in a fantastic location just off Hwy 22 in Enville, Tennessee. This versatile tract offers convenient ac...

3183906 MLS
ACTIVE Status
143.34 Acres
38332 Zip Code

Enville Road, Henderson $95,000

Own 10.30 fully wooded acres with total privacy in Sweet Lips, Tennessee. This unrestricted property features mature oak and pine hardwoods, flat terrain with only 1-5% s...

3183286 MLS
ACTIVE Status
10.3 Acres
38340 Zip Code

5030 Sand Mountain Rd, Enville $89,900 ▼

Beautiful 12+/- acre parcel located on Sand Mountain Road in Enville. This property offers a great opportunity to build your dream home or place a manufactured home in a ...

3147736 MLS
ACTIVE Status
12 Acres
38332 Zip Code

341 Melodie Cir, Henderson $242,500 ▼

Welcome to 341 Melodie Circle in Henderson, Tennessee — where comfort, updates, and privacy come together. This well-maintained home features beautifully updated bathroo...

3 Beds
2 Baths
3136958 MLS
ACTIVE Status
0.71 Acres
38340 Zip Code

S State Route 22A, Enville $225,550

Escape to Tennessee Country Living on this 45.11 parcel situated in Enville, TN. Ideally located just 20 miles from Lexington, Henderson, and Savannah, TN, this property ...

3047408 MLS
ACTIVE Status
45.11 Acres
38332 Zip Code

Information Is Believed To Be Accurate But Not Guaranteed. Some or all listings may or may not be listed by the office/agent presenting these featured properties. Copyright 2026 MTRMLS, Inc. RealTracs Solutions.