Chester County, TN Homes

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  /53

  $359,900

  • 3 Beds
  • 2.5 Baths
  • 1,897 Sq Ft

  170 Tall Pines Rd, Henderson, TN 38340

  LOVELY BRICK HOME WITH 3 BEDROOMS, 2.5 BATHS LOCATED IN A FANTASTIC NEIGHBORHOOD. THE MASTER BATH HAS A WHIRLPOOL TUB, SEPARATE SHOWER, DOUBLE VANITIES, BEDROOM 2 AND 3 HAS A JACK AND JILL BATHROOM, BEAUTIFUL DINING ROOM, ALSO A GREAT BREAKFAST NOOK, KITCHEN HAS QUARTZ COUNTER TOPS, THIS HOME HAS A LARGE BACK FENCED IN-YARD, LARGE PATIO WITH AN OUTSIDE GRILL, STORAGE BUILDING OUTSIDE FENCED IN

  Linda Carter Casey Realtors

  170 Tall Pines Rd, Henderson, TN 38340
• 

  

  

  /23

  $203,900 Sold May 30, 2025

  • 2,809 Sq Ft
  • $73/SF
  • 90 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1969

  154 N Carolina Ave, Henderson, TN 38340

  A lot of house for the money with this 4 bedroom which is set up as 5 now. FLR, Den, DR and kitchen bar with big back yard and above ground pool. Metal roof, oak kitchen cabinets and a whole lot more. Call to schedule your showing today while it's still here.

  Betty Brown Vantage Real Estate Services

  154 N Carolina Ave, Henderson, TN 38340
• 

  

  

  /20

  Est $313,490 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,768 Sq Ft

  2755 Sanford Rd, Henderson, TN 38340

  2755 Sanford Rd, Henderson, TN 38340
• 

  

  

  /28

  $295,000

  • 3 Beds
  • 3 Baths
  • 2,312 Sq Ft

  511 White Ave, Henderson, TN 38340

  Take a look at this nicely remodeled 3-bedroom, 3-bath stone exterior home in a great location. Within walking distance to Freed-Hardeman University, schools, and shopping, this home offers both convenience and comfort.Inside, the home features beautiful restored hardwood floors that bring out its original charm. The master bedroom includes an adjoining bath, and the large secondary

  Richard Emison NextHome 383 Real Estate

  511 White Ave, Henderson, TN 38340
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  /9

  $605,000 Sold May 30, 2025

  • 8,975 Sq Ft
  • $67/SF
  • 251 Days On Market

  • Built 1972

  974 Woodland Dr, Henderson, TN 38340

  Total of 2 Quadplexes and 1 Duplex. 10 Units. Each unit is 2BR 1 Bath. Longterm tenants. $600 per unit rent. 952A-D 4 units 962A-B 2 units 974A-D 4 units Please do not disturb the tenants

  Larry Roberts Casey Realtors

  974 Woodland Dr, Henderson, TN 38340
• 

  

  /21

  Est $232,703 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  230 Sugar Creek Dr, Henderson, TN 38340

  230 Sugar Creek Dr, Henderson, TN 38340
• 

  

  /66

  $525,000

  • 4 Beds
  • 2 Baths
  • 2,744 Sq Ft

  320 Rabbit Ranch Rd, Henderson, TN 38340

  Welcome to your private retreat—this charming 4-bedroom, 2-bath brick home is nestled on a sprawling 57-acre estate offering a rare combination of space, seclusion, and opportunity. Whether you’re looking for a forever home, hobby farm, or hunter’s paradise, this property delivers.Step inside to find a warm and inviting interior with spacious living areas, a functional kitchen, and a cozy

  ERICA MAXWELL Tiffany Jones Realty Group, LLC

  320 Rabbit Ranch Rd, Henderson, TN 38340
• 

  

  /19

  $189,900 Sold May 29, 2025

  • 1,112 Sq Ft
  • $171/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1969

  639 Mifflin Ave, Henderson, TN 38340

  THIS HOME IS FOR ITS NEW FAMILY, WITHIN WALING DISTANCE TO FHU, GROCERY STORE, WHATEVER YOU NEED, SO MUCH REMODELING HAS BEEN DONE, CALL FOR ALL ITEMS NEW PAINT INSIDE AND HOUSE ON OUTSIDE HAS BEEN PAINTED, , NEW WINDOWS, NEW FLOORING, SOME NEW CENTRAL H V/VENTS, 2 CAR GARAGE WITH GARAGE DOOR, NEW COUNTERTOP IN KITCHEN , NEW KITCHEN SINK LOTS OF REMODELING, REFRIGERATOR CAN STAY (ICE MAKER

  Linda Carter Casey Realtors

  639 Mifflin Ave, Henderson, TN 38340
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  /27

  Est $226,093 Not Listed For Sale

  • Studio
  • 572 Sq Ft

  445 Smith Ln Unit 590, Henderson, TN 38340

  445 Smith Ln Unit 590, Henderson, TN 38340
• 

  

  /20

  $289,900

  • 3 Beds
  • 2 Baths
  • 1,465 Sq Ft

  4745 Enville Rd, Henderson, TN 38340

  This Charming 2012 Build in Henderson, TN on 1.00+- Acres is Hitting the Market! This Home Was Remodeled in 2024 with New Roof, LVP Flooring, Custom Cabinetry with Stunning Countertops, Tiled Shower in Primary, Large Living Room Semi Open to Kitchen with Dining Area ; This Home HVAC Was Updated in 2025 with New Ductwork with Extra in Primary Bedroom, UV Lighting and Ozone Generator, Polarized

  Drake Harber Blue Suede Realty

  4745 Enville Rd, Henderson, TN 38340
• 

  

  /51

  $380,000 Sold May 29, 2025

  • 2,080 Sq Ft
  • $183/SF
  • 11 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1976

  5160 Sunshine Rd, Henderson, TN 38340

  Experience country living at its finest with this stunning, newly renovated home on nearly eight acres in Chester County! Enjoy breathtaking sunsets over the pond from the gorgeous wraparound porch or take in the serene views of the rolling pastures. Inside, the open-concept floor plan features over 2,000 sq ft of beautifully designed living space, including a spacious kitchen with an oversized

  Madison Balding Town and Country

  5160 Sunshine Rd, Henderson, TN 38340
• 

  

  /31

  Est $225,802 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  6450 Old Jacks Creek Rd, Henderson, TN 38340

  6450 Old Jacks Creek Rd, Henderson, TN 38340
• 

  

  /32

  $474,900

  • 4 Beds
  • 3 Baths
  • 2,720 Sq Ft

  137 Gibson Dr, Henderson, TN 38340

  Step into history with this exquisite Chester County landmark, built in 1952 and was once the home of Former Circuit Court Judge Willard E. Smith. This stunning home, a testament to timeless elegance, has been lovingly renovated to offer modern amenities while preserving its historic charm.Property Highlights:-Size: 2,650 sqft of meticulously renovated living space-Bedrooms: 4

  Brent West Crye-Leike Elite

  137 Gibson Dr, Henderson, TN 38340
• 

  

  /73

  $474,500 Sold May 28, 2025

  • 5,944 Sq Ft
  • $80/SF
  • 203 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 2001

  230 Oak Ridge Dr, Henderson, TN 38340

  THIS BEAUTIFUL HOME HAS SO, SO , SO TO OFFER A FAMILY, SO MUCH SPACE WITH 6 ACRES MORE OR LESS IN A WONDERFUL SUBDIVISION, THIS HOME HAS A MAIN LEVEL PLUS A FINISHED BASEMENT WITH 4 BEDROOM , 2 BATHS, L/R,DEN,KITCHEN, OFFICE AND SO MUCH MORE, MAIN LEVEL HAS THE MASTER BEDROOM, AND 1 MORE BEROOM, 2 BATHS, LIVING ROOM W/FIRPLACE,, DINING ROOM, DEN, AND SO MUCH MORE, PERMANENT STAIRS TO A FANTASTIC

  Linda Carter Casey Realtors

  230 Oak Ridge Dr, Henderson, TN 38340
• 

  

  /18

  Est $189,653 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,603 Sq Ft

  655 Glendale Rd, Henderson, TN 38340

  655 Glendale Rd, Henderson, TN 38340
• 

  

  /27

  $289,900

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  380 Melodie Cir, Henderson, TN 38340

  MOTIVATED SELLER! Built in 2024, this beautiful barndominium offers 3 bedrooms, 2.5 bathrooms, and nearly 1,700 sq ft of modern living on a 0.78-acre lot. Enjoy 10-foot ceilings throughout and an open-concept layout with a vaulted living room that adds warmth and charm.The kitchen features butcher block countertops and a spacious walk-in pantry with a sliding barn door. Epoxy floors run

  Michelle Lilly Lilly Realty

  380 Melodie Cir, Henderson, TN 38340
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  /5

  $100,900 Sold May 20, 2025

  • 606 Sq Ft
  • $167/SF
  • 24 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1950

  580 Sanford St, Henderson, TN 38340

  Welcome to this beautifully remodeled 2-bedroom, 1-bath home! Freshly updated with new flooring, paint, and light fixtures, this inviting residence is ready for you to move in and make it your own.Enjoy the spacious large backyard, perfect for outdoor activities, gardening, or simply relaxing.Located in a convenient area of town, you'll have easy access to shops, dining, and local amenities.

  Zach Hannis Casey Realtors

  580 Sanford St, Henderson, TN 38340
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  /42

  Est $405,799 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,041 Sq Ft

  470 Ludell Ross Rd, Enville, TN 38332

  470 Ludell Ross Rd, Enville, TN 38332
• 

  

  /43

  $315,000

  • 4 Beds
  • 2.5 Baths
  • 1,948 Sq Ft

  2925 Tennessee 100, Henderson, TN 38340

  Welcome to 2925 State Route 100 W in Henderson! This beautifully updated 4 bedroom, 2.5 bath home is tucked away on a peaceful 2.65 acre lot. Located just half a mile from West Chester Elementary., This home provides both convenience and a serene setting. Inside, you will find nearly 2,000 square feet of living space with modern upgrades throughout-including updated (LVP) flooring. The

  Jennifer Scott RE/MAX Realty Source

  2925 Tennessee 100, Henderson, TN 38340
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  /27

  $149,000 Sold May 16, 2025

  • 1,002 Sq Ft
  • $149/SF
  • 84 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1949

  950 Old Montezuma Rd, Henderson, TN 38340

  This charming two bedroom, one bath home built in 1949 certainly boasts vintage appeal! Sitting on 4.63 acres, this property offers ample space for outdoor activities & potential expansion. It's inviting character & cozy layout make this home an ideal starter home for first-time buyers or an excellent investment opportunity for those looking to tap into the real estate market. Conveniently

  Jennifer Maness-Scott Stellar Realty Group

  950 Old Montezuma Rd, Henderson, TN 38340
• 

  

  /16

  Est $154,739 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  740 Smith Rd, Luray, TN 38352

  740 Smith Rd, Luray, TN 38352
• 

  

  /31

  $330,000

  • 3 Beds
  • 2 Baths
  • 2,059 Sq Ft

  836 Hill Ave, Henderson, TN 38340

  FANTASTIC BRICK HOME IN AN EXCELLENT LOCATION JUST WAITING ON ITS NEW FAMILY, 3 BR., 2 BATHS, FORMAL DINING ROOM, LARGE GARAGE, LOTS OF BEAUTIFUL FLOWER BEDS, LARGE DECK AND GREAT BACK FENCED IN YARD

  Linda Carter Casey Realtors

  836 Hill Ave, Henderson, TN 38340
• 

  

  /24

  $255,000 Sold May 16, 2025

  • 1,679 Sq Ft
  • $152/SF
  • 49 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  734 Mason Ave, Henderson, TN 38340

  A well built 2006 brick home with over 1670 heated square foot including 3BR, 2BA, kitchen, den and dining room. A nice size lot located on a dead end street in Quail Run Estates, In downtown Henderson, close to shopping areas, Freed Hardeman University and Chester county great school system. The home is just 15 minutes from Jackson, TN with its larger shopping, work centers and outstanding

  Mike Singleton McIver Land & Realty

  734 Mason Ave, Henderson, TN 38340
• 

  

  /24

  Est $226,833 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft

  6650 State Route 22, Enville, TN 38332

  6650 State Route 22, Enville, TN 38332
• 

  

  /22

  $284,500

  • 3 Beds
  • 3 Baths
  • 2,440 Sq Ft

  225 E Third St, Henderson, TN 38340

  BEAUTIFUL BRICK HOME WITHIN 2 BLOCKS FROM FHU, WITH SO MUCH TO OFFER A FAMILY, DEN, LIVING,ROOM, SUNROOM, 2 BEDROOMS,DOWN WITH 2 BATHS, LARGE BONUS ROOM UP WITH BATH, PLUS AN OFFICE AREA, FIREPLACE W/GAS LOGS IN DEN, LARGE FENCED IN BACKYARD FOR OUR FUR BABIES OR YOUR REGULAR BABIES AND SO MUCH MORE. THIS IS A MUCH SEE.

  Linda Carter Casey Realtors

  225 E Third St, Henderson, TN 38340
• 

  

  /59

  $247,500 Sold May 16, 2025

  • 2,048 Sq Ft
  • $121/SF
  • 370 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  15 Mitchell Ln, Henderson, TN 38340

  Strategically positioned just beyond the city limits, this meticulously renovated 3 bedroom, 2 bathroom residence epitomizes modern sophistication. Boasting top-of-the-line appliances, fresh paint, and high-end luxury vinyl plank flooring, this property exudes luxury and refinement. The fenced yard and covered back porch provide serene outdoor retreats, while the sunken den adds a distinctive

  Larry Roberts Casey Realtors

  15 Mitchell Ln, Henderson, TN 38340
• 

  

  /28

  Est $276,333 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,848 Sq Ft

  2240 State Route 225, Henderson, TN 38340

  2240 State Route 225, Henderson, TN 38340
• 

  

  /47

  $479,000

  • 3 Beds
  • 2 Baths
  • 2,201 Sq Ft

  480 Ridgewood Dr, Henderson, TN 38340

  Beautiful all brick home w/neutral paint color, 3 bedrooms, 2 baths w/ bonus room w/carpet upstairs, w/separate heat/air units. Wonderful 24 x 30 shop within a few steps of the house(extra clean) Hardwood floors throughout w/ carpet only in the two additional bedrooms. Tile in bathrooms and laundry room. Very large Laundry room. Home sits on 1.3 acres of beautiful fully sodded Bermuda hybrid

  Linda Carter Casey Realtors

  480 Ridgewood Dr, Henderson, TN 38340
• 

  

  /16

  $195,000 Sold May 15, 2025

  • 1,079 Sq Ft
  • $181/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2022

  365 E 4th St, Henderson, TN 38340

  Looking for an established short-term investment property? This beautiful 3 bed 2 bath home may be just the one for you! Located minutes from Freed Hardeman University and downtown Henderson, your guests will be able to easily access the amenities Henderson has to offer. Do not miss the opportunity to make this short term rental yours! Looking for an established short-term investment property?

  Aaliyah Cupples Stellar Realty Group

  365 E 4th St, Henderson, TN 38340
• 

  

  /25

  Est $161,242 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,175 Sq Ft

  419 Regina Dr, Henderson, TN 38340

  419 Regina Dr, Henderson, TN 38340
• 

  

  /33

  $279,900

  • 6 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  208 Fourth St, Henderson, TN 38340

  Charming 6 BR 2.5 BA Home w/Office in Henderson, TN - Prime Location near Freed Hardemon UniversityWelcome to your dream home in the heart of Henderson! This exquisite property, ideally situated on a corner lot, offers unparalleled convenience, being within walking distance to Freed Hardemon University, Main St, and all that Henderson has to offer.Key Features:Complete

  Richard Emison NextHome 383 Real Estate

  208 Fourth St, Henderson, TN 38340
• 

  

  /15

  $259,000 Sold May 05, 2025

  • 2,100 Sq Ft
  • $123/SF
  • 90 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1960

  603 Luray Ave, Henderson, TN 38340

  **For Sale: Beautifully Renovated 4-Bedroom, 2-Bath Home**Welcome to your dream home! This stunning newly renovated 4-bedroom, 2-bathroom residence combines modern elegance with comfort, making it the perfect sanctuary for you and your family.Spacious Open Living area boasts an open floor plan that seamlessly connects the living room, dining area, and kitchen, providing an ideal space for

  Anthony Mannie KAIZEN Realty, LLC

  603 Luray Ave, Henderson, TN 38340
• 

  

  /19

  Est $218,140 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,949 Sq Ft

  241 Crook Ave, Henderson, TN 38340

  241 Crook Ave, Henderson, TN 38340
• 

  

  /17

  $289,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  454 Old Jackson Rd, Henderson, TN 38340

  Don't miss your chance to own this beautifully designed 3 bed, 2 bath home with 1,560 sqft of modern comfort at 454 Old Jackson Rd in Henderson, TN! Step into a spacious open-concept layout that's perfect for entertaining and everyday living. The heart of the home is the luxurious kitchen—featuring sleek finishes, ample counter space, and premium appliances that will impress any home chef. With

  Brent West Crye-Leike Elite

  454 Old Jackson Rd, Henderson, TN 38340
• 

  

  /26

  $235,000 Sold May 02, 2025

  • 1,477 Sq Ft
  • $159/SF
  • 46 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  722 Hearn St, Henderson, TN 38340

  This adorable 3-bedroom, 2-bath home is move-in ready with fresh paint throughout and beautiful hardwood flooring. Step outside to enjoy the spacious backyard, complete with a brand-new oversized deck—perfect for entertaining or relaxing. Conveniently located just 15 minutes from South Jackson and less than 5 minutes from Main Street in Henderson, this home offers both comfort and convenience.

  Madison Balding Town and Country

  722 Hearn St, Henderson, TN 38340
• 

  

  /46

  Est $484,474 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,814 Sq Ft

  4125 Old Jacks Creek Rd, Henderson, TN 38340

  4125 Old Jacks Creek Rd, Henderson, TN 38340
• 

  

  /21

  $280,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  1510 Talley Store Rd, Henderson, TN 38340

  Welcome to your dream retreat where country charm meets convenience! This immaculately kept one-level, 3-bedroom, 2-bath home sits on a spacious 1-acre lot with a privacy fence, offering the perfect blend of seclusion and accessibility. Step outside and enjoy the huge covered deck, ideal for relaxing, entertaining, or simply taking in the peaceful surroundings.Inside, you'll find a bright and

  Scott Shelton Crye-Leike Elite

  1510 Talley Store Rd, Henderson, TN 38340
• 

  

  /13

  $38,000 Sold May 01, 2025

  • Land
  • 5 Acres
  • $7,525 per Acre

  • 52 Days On Market

  TRACT 4 Tennessee 225, Henderson, TN 38340

  OWNER FINANCE LAND - $42K - $1000 DOWN & $360/MTH NO CREDIT CHECKS BEAUTIFUL TENNESSEE LAND IN CHESTER COUNTY, TN. NICE 5.05 ACRES LOT SR 225 BETHEL SPRINGS TN. LAND IS UNRESTRICTED AND POWER IS AVAILABLE THIS IS VERY USABLE LAND! Build a house, mobile home or many different uses If you notice in the survey, there is a gas pipeline easement going thru a portion of the middle of the property,

  Timothy Crane 2 Cranes Realty

  TRACT 4 Tennessee 225, Henderson, TN 38340
• 

  

  /38

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,277 Sq Ft

  2600 Silerton Rd, Henderson, TN 38340

  2600 Silerton Rd, Henderson, TN 38340
• 

  

  /26

  $319,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,940 Sq Ft

  145 Dlynn Cove, Henderson, TN 38340

  Charming and spacious 4-bedroom, 2-bathroom home situated on a full acre lot! Enjoy outdoor living with a large backyard that includes a deck and a storage shed with electricity available and pull down stairs. The backyard is perfect for relaxing or entertaining. Inside, the home features tall ceilings and a cozy fireplace in the living room, all conveniently located on a single level. The

  Kristen Londe Town and Country

  145 Dlynn Cove, Henderson, TN 38340

Showing Results 161 - 200, Page 5 of 18