Monroe County, KY Homes

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  /13

  $14,900

  • Land
  • 18,295 Sq Ft
  • $35,476 per Acre

  Lot #3 715 Emberton St, Tompkinsville, KY 42167

  Lot #3 offers 0.4259 +/- acres in the city limits, a partially wooded lot with room to build, plus road frontage for easy access. This prime property blends natural charm with convenient urban proximity-perfect for your next development or dream home.

  Ryan Brown United Country - Lakes and Land Realty

  Lot #3 715 Emberton St, Tompkinsville, KY 42167
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  /32

  $410,000

  Sold Apr 21, 2026

  69 AC Radio Station Rd, Tompkinsville, KY 42167

  • Land
  • 69 Acres
  • $5,942 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 314 Days On Market

  Last Listing Agent Sara Leftwich Mills Real Estate & Auction Co., LLC - Glasgow

  69 AC Radio Station Rd, Tompkinsville, KY 42167
• 

  

  

  /12

  Est $180,155

  Not Listed For Sale

  2180 Strodetown Rd, Tompkinsville, KY 42167

  • 3 Beds
  • 2 Baths
  • 2,450 Sq Ft
  • Built 1993

  2180 Strodetown Rd, Tompkinsville, KY 42167

  Last Sold Summary

  • 95% Above List Price
  • $38/SF
  • 14 Days On Market

  • Last Sold Price $92,500
  • May 18, 2020

  Last Listing Agent Steve Wilson Wilson Real Estate & Auction
• 

  

  

  /7

  $188,000

  • Land
  • 23.5 Acres
  • $8,000 per Acre

  1997 Vernon Rd, Hestand, KY 42151

  Super nice acreage located a short distance out of Tompkinsville. This property has 23.50 acres of mostly open ground with some woodland on it. It has a good older combination barn, approx. 43x64 with a 16x64 shed on it. Partially fenced, also has a nice large pond located on it. Good road frontage and several good potential building sites on it. This property is only a short distance from

  Bobby Lane Big South Realty & Auction, LLC - Gamaliel

  1997 Vernon Rd, Hestand, KY 42151
• 

  

  /2

  $162,000

  Sold Dec 30, 2025

  2241 Old Glasgow Rd, Tompkinsville, KY 42167

  • Land
  • 17 Acres
  • $9,529 per Acre

  Last Sold Summary

  • 28% Below List Price
  • 115 Days On Market

  Current Estimated Value $236,201

  Last Listing Agent Dakota Elmore Elmore Realty & Auction

  2241 Old Glasgow Rd, Tompkinsville, KY 42167
• 

  

  /17

  Est $353,048

  Not Listed For Sale

  488 Brown Cemetery Rd, Tompkinsville, KY 42167

  • 2 Beds
  • 2 Baths
  • 2,250 Sq Ft
  • Built 1978

  488 Brown Cemetery Rd, Tompkinsville, KY 42167

  Last Sold Summary

  • 128% Above List Price
  • $69/SF
  • 325 Days On Market

  • Last Sold Price $155,000
  • Aug 12, 2016

  Last Listing Agent Steve Wilson Wilson Real Estate & Auction
• 

  

  /10

  $99,500

  $15K PRICE DROP

  • Land
  • 8.5 Acres
  • $11,706 per Acre

  1100A Harlan Crossroads Red Hill Rd, Tompkinsville, KY 42167

  Beautiful 8.5-acre property 25 minutes from Dale Hollow Lake! Generous road frontage and easy access. Gently rolling terrain offers multiple ideal building sites for your dream home or barndominium. Perfect for a hobby farm, gardens, or recreational use. Enjoy privacy and wide open spaces. This 8.5-acre tract features gently rolling, open ground with productive soil currently being leased for row

  Silas Sparrow Hayden Outdoors Real Estate

  1100A Harlan Crossroads Red Hill Rd, Tompkinsville, KY 42167
• 

  

  /21

  $160,000

  Sold Aug 08, 2025

  3197 Center Point Rd, Tompkinsville, KY 42167

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1968

  Last Sold Summary

  • 6% Below List Price
  • $89/SF
  • 180 Days On Market

  Current Estimated Value $180,928

  Last Listing Agent Steve Wilson Wilson Real Estate & Auction

  3197 Center Point Rd, Tompkinsville, KY 42167
• 

  

  /18

  Est $294,755

  Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 3 Baths
  • 2,933 Sq Ft
  • Built 1966

  Unlisted Address

  Last Sold Summary

  • 75% Above List Price
  • $57/SF
  • 160 Days On Market

  • Last Sold Price $168,000
  • Nov 04, 2019

  Last Listing Agent Sharon Proffitt Proffitt Real Estate Agency
• 

  

  /30

  $159,000

  $6K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 1,219 Sq Ft

  50 Dowell Dr, Tompkinsville, KY 42167

  Super nice remodeled 2 bedroom, 1 bath, full basement brick home in the city limits of Tompkinsville. This house has new flooring thru out, fresh paint in all the rooms, and the kitchen cabinets and countertops have been redone. The basement has had the floor refinished and new LED lights installed. This house sits on a nice lot with mature trees and has a rear patio, front porch, and a side

  Bobby Lane Big South Realty & Auction, LLC - Gamaliel

  50 Dowell Dr, Tompkinsville, KY 42167
• 

  

  /8

  $952,536

  Sold May 06, 2026

  10000 Bugtussle Rd, Fountain Run, KY 42133

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Ben Bray BHGRE, Ben Bray & Associates

  10000 Bugtussle Rd, Fountain Run, KY 42133
• 

  

  /18

  Est $205,428

  Not Listed For Sale

  2332 Old Glasgow Rd, Tompkinsville, KY 42167

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft

  2332 Old Glasgow Rd, Tompkinsville, KY 42167

  Last Sold Summary

  • 174% Above List Price
  • $39/SF
  • 106 Days On Market

  • Last Sold Price $75,000
  • Nov 09, 2017

  Last Listing Agent Steve Wilson Wilson Real Estate & Auction
• 

  /2

  $15,000

  • Land
  • 19,166 Sq Ft
  • $34,091 per Acre

  AC Rockbridge School Rd, Tompkinsville, KY 42167

  If your looking for a beautiful area to build a home, this is a great location! This lot is unrestricted with electric and water available. There is also a septic tank already on the lot. Acreage in this area does not come available often! Don't miss out on this opportunity.

  Sara Leftwich Mills Real Estate & Auction Co., LLC - Glasgow

  AC Rockbridge School Rd, Tompkinsville, KY 42167
• 

  /2

  $250,000

  Sold Jun 26, 2025

  0 Pipeline Rd, Summer Shade, KY 42166

  • Land
  • 48.97 Acres
  • $5,105 per Acre

  Last Sold Summary

  • 99% Below List Price
  • 0 Days On Market

  Last Listing Agent Sharon Proffitt Proffitt Real Estate Agency

  0 Pipeline Rd, Summer Shade, KY 42166
• 

  

  /11

  Est $161,884

  Not Listed For Sale

  172 Clementsville Rd, Gamaliel, KY 42140

  • 3 Beds
  • 1 Bath
  • 1,208 Sq Ft
  • Built 1973

  172 Clementsville Rd, Gamaliel, KY 42140

  Last Sold Summary

  • 90% Above List Price
  • $70/SF
  • 12 Days On Market

  • Last Sold Price $85,000
  • Jun 09, 2017

  Last Listing Agent Joe Murphy Big South Realty & Auction, LLC - Gamaliel
• 

  /2

  $79,900

  Pending

  • 3 Beds
  • 1 Bath
  • 1,420 Sq Ft

  2235 Elbow Bend Rd, Tompkinsville, KY 42167

  Joe Murphy Mills Real Estate & Auction Co

  2235 Elbow Bend Rd, Tompkinsville, KY 42167
• 

  /2

  $10,000

  Sold May 19, 2025

  Lot 3 Saddlebrook Estates, Tompkinsville, KY 42167

  • Land
  • 38,768 Sq Ft
  • $11,236 per Acre

  Last Sold Summary

  • 13% Below List Price
  • 662 Days On Market

  Last Listing Agent Sara Leftwich Mills Real Estate & Auction Co., LLC - Glasgow

  Lot 3 Saddlebrook Estates, Tompkinsville, KY 42167
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  /16

  Est $80,827

  Not Listed For Sale

  98 Mill St, Fountain Run, KY 42133

  • 3 Beds
  • 1 Bath
  • 672 Sq Ft

  98 Mill St, Fountain Run, KY 42133

  Last Sold Summary

  • 1,517% Above List Price
  • $7/SF
  • 142 Days On Market

  • Last Sold Price $5,000
  • Jul 27, 2018

  Last Listing Agent Greg Raymer NextHome Realty Experts
• 

  

  /9

  $246,500

  • Land
  • 17 Acres
  • $14,500 per Acre

  1 County House Rd, Tompkinsville, KY 42167

  Seventeen acres of Kentucky countryside, wide and open, with a mix of level pasture and gentle rolling hills that make it feel like something straight out of a country song. Zoned agricultural, this land is a clean slate—perfect for a dream home, mini-farm, or a quiet hideaway where you can hear your thoughts and watch the stars actually sparkle. Tompkinsville sits at the heart of Monroe County,

  MaKenzie Griffis GRATEFUL ACRES REALTY

  1 County House Rd, Tompkinsville, KY 42167
• 

  $45,000

  Sold May 14, 2026

  Lot 32 the Bend at the Cumberland, Tompkinsville, KY 42167

  • Land
  • 1.29 Acres
  • $34,884 per Acre

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Sherri Butler McIver Realty Group

  Lot 32 the Bend at the Cumberland, Tompkinsville, KY 42167
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  /9

  Est $112,121

  Not Listed For Sale

  398 Mill St, Fountain Run, KY 42133

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft
  • Built 2003

  398 Mill St, Fountain Run, KY 42133

  Last Sold Summary

  • 673% Above List Price
  • $15/SF
  • 305 Days On Market

  • Last Sold Price $14,500
  • Feb 28, 2019

  Last Listing Agent Greg Raymer NextHome Realty Experts
• 

  

  /23

  $139,900

  $35K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 2,547 Sq Ft

  200 E Main St, Gamaliel, KY 42140

  BIG PRICE REDUCTION ON HOUSE in the city limits of Gamaliel, Ky. This is a nice brick home that has a foyer, living room, dining room, kitchen, sitting room, 2 bedrooms, 11⁄2 baths, and a laundry room on the main level. On the 2nd level there are 3 bedrooms and 1 full bath. This home has a full unfinished basement that has a shower as well as an inside and outside entrance. This home has a

  Sharon Proffitt Proffitt Real Estate Agency

  200 E Main St, Gamaliel, KY 42140
• 

  

  /18

  $235,000

  Sold Oct 30, 2025

  155 Spring Valley, Tompkinsville, KY 42167

  • 3 Beds
  • 2 Baths
  • 2,148 Sq Ft
  • Built 1989

  Last Sold Summary

  • 15% Below List Price
  • $109/SF
  • 42 Days On Market

  Current Estimated Value $212,786

  Last Listing Agent Sara Leftwich Mills Real Estate & Auction Co., LLC - Glasgow

  155 Spring Valley, Tompkinsville, KY 42167
• 

  

  /11

  Not Listed For Sale

  319 Jack Hunt Rd, Tompkinsville, KY 42167

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  319 Jack Hunt Rd, Tompkinsville, KY 42167

  Last Sold Summary
• 

  

  /20

  $464,900

  $35K PRICE DROP

  • 6 Beds
  • 2 Baths
  • 3,200 Sq Ft

  2967 Bethlehem Church Rd, Mount Hermon, KY 42157

  Rare opportunity to own an organically certified Kentucky farm with a spacious country home. This 22.89-acre property features a 3,200 sq ft, 6-bedroom, 2-bath residence featuring an additional kitchen in basement. The farm is blessed with rolling pastureland offering creek frontage and woodlands. The property is well equipped with a barn and an equipment shop, making it ideal for agricultural

  Brad Young United Country, Heartland Realty & Auction, LLC

  2967 Bethlehem Church Rd, Mount Hermon, KY 42157
• 

  

  /6

  $75,000

  Sold Apr 14, 2026

  600 Lake St, Tompkinsville, KY 42167

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft
  • Built 1955

  Last Sold Summary

  • 17% Below List Price
  • $85/SF
  • 0 Days On Market

  Current Estimated Value $87,339

  Last Listing Agent Sharon Proffitt Proffitt Real Estate Agency

  600 Lake St, Tompkinsville, KY 42167
• 

  

  /3

  Not Listed For Sale

  1 Archer Rd, Lafayette, TN 37083

  1 Archer Rd, Lafayette, TN 37083

  Last Sold Summary

  • Last Sold Price $10,000
  • Jan 25, 2016

  Last Listing Agent Ben Bray BHGRE, Ben Bray & Associates
• 

  

  /6

  $95,000

  $10K PRICE DROP

  • Land
  • 5.53 Acres
  • $17,179 per Acre

  5.5 AC F Bartley Rd, Tompkinsville, KY 42167

  Joe Murphy Big South Realty & Auction, LLC - Gamaliel

  5.5 AC F Bartley Rd, Tompkinsville, KY 42167
• 

  /2

  $177,100

  Sold Nov 25, 2025

  50 Coach O Dr, Tompkinsville, KY 42167

  • 2 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • Built 1990

  Last Sold Summary

  • $104/SF
  • 10 Days On Market

  Current Estimated Value $161,477

  Last Listing Agent Joe Costello Mills Real Estate & Auction

  50 Coach O Dr, Tompkinsville, KY 42167
• 

  

  /22

  Est $193,230

  Not Listed For Sale

  849 Rivers Edge Loop, Tompkinsville, KY 42167

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2007

  849 Rivers Edge Loop, Tompkinsville, KY 42167

  Last Sold Summary

  • 41% Above List Price
  • $98/SF
  • 703 Days On Market

  • Last Sold Price $136,950
  • Apr 12, 2017

  Last Listing Agent Paul Thomas Mossy Oak Properties Hart Realty
• 

  

  /7

  $23,900

  • Land
  • 1.02 Acres
  • $23,431 per Acre

  0 Spring St, Tompkinsville, KY 42167

  You must take a look at this nice 1.02 acre lot located in the beautiful Clark Estates subdivision. This would be perfect to build your dream home on & you could not ask for better neighbors.

  Sharon Proffitt Proffitt Real Estate Agency

  0 Spring St, Tompkinsville, KY 42167
• 

  

  /18

  $349,000

  Sold Jul 28, 2025

  305 Beech Grove Boles Rd, Tompkinsville, KY 42167

  • 2 Beds
  • 1.5 Baths
  • 1,300 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Below List Price
  • $268/SF
  • 65 Days On Market

  Current Estimated Value $228,000

  Last Listing Agent Michael Dubree Patriot Realty - Auction LLC

  305 Beech Grove Boles Rd, Tompkinsville, KY 42167
• 

  

  /24

  Est $417,705

  Not Listed For Sale

  1270 Poore Hollow Ln, Hestand, KY 42151

  • 3 Beds
  • 1 Bath
  • 1,792 Sq Ft
  • Built 2007

  1270 Poore Hollow Ln, Hestand, KY 42151

  Last Sold Summary

  • 132% Above List Price
  • $100/SF
  • 333 Days On Market

  • Last Sold Price $179,950
  • Sep 26, 2017

  Last Listing Agent Jerri Beth Williams Mossy Oak Properties Hart Realty
• 

  

  /15

  $19,500

  • Land
  • 18,295 Sq Ft
  • $46,429 per Acre

  Lot #1 715 Emberton St, Tompkinsville, KY 42167

  Prime building lot Lot #1, spanning 0.4259+/- acres and thoughtfully located within the city limits, offering the perfect canvas for your custom home. Utilities are readily available, simplifying construction and timeline.

  Ryan Brown United Country - Lakes and Land Realty

  Lot #1 715 Emberton St, Tompkinsville, KY 42167
• 

  

  /25

  $179,000

  Sold Jul 21, 2025

  261 Martha Ln, Tompkinsville, KY 42167

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Below List Price
  • $112/SF
  • 20 Days On Market

  Last Listing Agent Sharon Proffitt Proffitt Real Estate Agency

  261 Martha Ln, Tompkinsville, KY 42167
• 

  

  /28

  Not Listed For Sale

  143 ACS Kettle Creek Monroe Rd, Tompkinsville, KY 42167

  143 ACS Kettle Creek Monroe Rd, Tompkinsville, KY 42167

  Last Sold Summary

  • 0 Days On Market

  • Last Sold Price $239,000
  • Apr 27, 2021

  Last Listing Agent Barbara McWhorter The Realty Firm - Byrdstown
• 

  

  /14

  $189,900

  $5K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  85 Willow Branch Rd, Tompkinsville, KY 42167

  Remarkable 4-bedroom, 2-bath manufactured home on a peaceful 1⁄2-acre lot! This beautifully maintained 1,568 sq. ft. home feels better than new, featuring a screened-in back porch perfect for relaxing, a 2-car carport, and a wired storage shed for all your tools and toys. Recent upgrades include a new roof (2025), new gutters (2024), durable LVT flooring, and consistent, thoughtful maintenance

  Brad Young United Country, Heartland Realty & Auction, LLC

  85 Willow Branch Rd, Tompkinsville, KY 42167
• 

  

  /38

  $79,000

  Sold Nov 21, 2025

  362 Main St, Fountain Run, KY 42133

  • 5 Beds
  • 1 Bath
  • 2,400 Sq Ft

  Last Sold Summary

  • 11% Below List Price
  • $33/SF
  • 4 Days On Market

  Current Estimated Value $78,740

  Last Listing Agent Sherri Butler McIver Realty Group

  362 Main St, Fountain Run, KY 42133
• 

  

  /7

  Not Listed For Sale

  4037 Flippin Lamb Rd, Glasgow, KY 42141

  • 3 Beds
  • 1 Bath
  • 1,316 Sq Ft

  4037 Flippin Lamb Rd, Glasgow, KY 42141

  Last Sold Summary

  • $35/SF
  • 275 Days On Market

  • Last Sold Price $46,000
  • Mar 16, 2018

  Last Listing Agent Non Member Licensee OUTSIDE MLS SALES OFFICE
• 

  /2

  $113,960

  • Land
  • 8.14 Acres
  • $14,000 per Acre

  0 Cave Springs Rd, Tompkinsville, KY 42167

  Great location in the city limits of Tompkinsville. 8.15 acres by recent survey overlooking Hagans Lake. Great building site. All city utilities available.

  Steve Wilson Wilson Real Estate & Auction

  0 Cave Springs Rd, Tompkinsville, KY 42167

Showing Results 161 - 200, Page 5 of 18