Chester County Homes for Sale

Searching for a Chester County home?

Chester County homes for sale should be compared by condition, updates, setting, lot size, financing fit, inspection risk, and the total monthly cost after taxes and insurance. In this part of Tennessee, the difference between a simple in-town home and a country home with acreage can change the due diligence list quickly.

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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

$245,000Median list price
$3,400Median price per acre
9Active listings
29Median days on market

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Talk with top Chester County real estate agents for homes for sale

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 home search strategy, pricing, offer terms, inspections, and negotiations. Contact THFRE about Chester County.

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Chester County homes for sale FAQs

An in-town home in Chester County typically means city water, sewer, and shorter inspection lists. A country home with acreage adds well condition, septic system age and capacity, road access, outbuildings, and lot usability to your due diligence. Both can be great purchases, but the checklist is different. Knowing which questions to ask before you make an offer keeps surprises from showing up after closing.

At minimum, plan for a full home inspection covering the roof, foundation, HVAC, electrical, and plumbing. On rural or older homes, add a well water test and septic inspection. If the home has a crawl space, moisture and structural checks matter. In Chester County, homes with acreage may also have outbuildings, fencing, or a pond that deserve a closer look. Build inspection contingencies into your offer so you can ask better questions, negotiate repairs, or walk away.

Start with condition and updates, then factor in lot size, setting, and what the monthly cost actually looks like after taxes and insurance. A newer roof, updated HVAC, and a clean inspection report are worth more than cosmetic finishes. Two homes at the same price can carry very different risk profiles. We help buyers look past the photos and compare what actually matters for long-term ownership.

Conventional, FHA, and USDA loans all see regular use in Chester County depending on the buyer's situation and the property itself. USDA rural development loans can be a strong fit for eligible buyers purchasing outside city limits, but the property and buyer both have to qualify. If the home has acreage or a well and septic, confirm your lender is comfortable with rural properties before you get too far into the process.

Start with the basics: clean, declutter, and handle any deferred maintenance that a buyer's inspector will flag. In Chester County, sellers of country homes should also make sure the well and septic are in good working order and that outbuildings and fencing are presentable. Pricing based on recent comparable sales, not what you hope the market will do, is the single biggest factor in how quickly and cleanly your home sells.

425B Second St, Henderson $70,000

Rare investment opportunity in the heart of Henderson! This historic home sits on approximately 1.2 acres in an established neighborhood and offers tremendous potential. ...

3 Beds
2 Baths
3302409 MLS
ACTIVE Status
1.2 Acres
38340 Zip Code

460 Kendyl Cv, Henderson $224,000

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

3280 Pleasant Springs Rd, Pinson $145,000

If you've been searching for an affordable home where you can simply unpack your boxes and make it your own over time, this may be exactly what you've been waiting for. S...

2 Beds
1 Baths
3287898 MLS
ACTIVE Status
1 Acres
38366 Zip Code

5885 State Route 225, Henderson $135,000

Welcome to 5885 State Route 225, Henderson, TN—a fantastic opportunity to own a solid brick home on approximately 2 acres. Offered at just $135,000, this property present...

3 Beds
2 Baths
3278521 MLS
ACTIVE Status
1.8399999999999999 Acres
38340 Zip Code

320 Benson Rd, Reagan $245,000

Welcome home to this beautifully updated 3-bedroom, 2-bath property nestled on 2.17 acres of peaceful, wooded surroundings! This home features an inviting open floor plan...

3 Beds
2 Baths
3246905 MLS
ACTIVE Status
2.17 Acres
38368 Zip Code

60 Proctor Rd, Henderson $2,100,000

Located in Henderson, Tennessee, this exceptional luxury estate offers upscale living and a premier equestrian lifestyle on approximately 30 private acres surrounded by w...

4 Beds
5 Baths
3230940 MLS
ACTIVE Status
30 Acres
38340 Zip Code

454 White Ave, Henderson $199,900 ▼

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

341 Melodie Cir, Henderson $264,900 ▼

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

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.

Chester County Homes for Sale

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Chester County Homes for Sale

Searching for a Chester County home?

See what your Chester County home is worth

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

Chester County real estate market stats — last 6 months

Talk with top Chester County real estate agents for homes for sale

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