3,272

Jamestown, KY Homes

Section Image
    • /90

      Est $655,327

      Not Listed For Sale

      530 Water Works Rd, Jamestown, KY 42629

      • 5 Beds
      • 3 Baths
      • 4,700 Sq Ft
      • Built 2003
      530 Water Works Rd, Jamestown, KY 42629

      Last Sold Summary

      • 161 Days On Market

      Last Listing Agent Kimberly Byrom Lake Cumberland Properties, Ltd. Co.

  • /52

    $319,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,751 Sq Ft

    87 Cherokee Springs Ct, Jamestown, KY 42629

    Welcome to 87 Cherokee Springs Ct in the peaceful Cherokee Springs area of Jamestown, KY. This charming 1.5-story home offers the perfect blend of comfort, updates, and Lake Cumberland lifestyle. The home now features 3 bedrooms, including a beautifully finished upstairs bedroom that was previously used as a loft/flex space, plus updated bathrooms with new vanities and sinks. The main level

    Torsten Langguth Prosperity Real Estate

    87 Cherokee Springs Ct, Jamestown, KY 42629
  • /29

    $330,000

    Sold Jun 19, 2026

    468 Sonny Aaron Dr, Jamestown, KY 42629

    • 3 Beds
    • 3 Baths
    • 2,200 Sq Ft
    • Built 2023

    Last Sold Summary

    • $150/SF
    • 1 Day On Market

    Current Estimated Value $322,700

    Last Listing Agent Shelly Stoyell PCS Real Estate

    468 Sonny Aaron Dr, Jamestown, KY 42629
    • /63

      Est $724,795

      Not Listed For Sale

      45 Lily Creek Ct, Jamestown, KY 42629

      • 4 Beds
      • 3 Baths
      • 3,400 Sq Ft
      • Built 2020
      45 Lily Creek Ct, Jamestown, KY 42629

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Whitney Marcum Lake Cumberland Properties, Ltd. Co.

  • /60

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,720 Sq Ft

    5029 S Highway 379, Jamestown, KY 42629

    Welcome to your own slice of Kentucky paradise in Creelsboro, just minutes from the charm of Jamestown. Located conveniently along the Cumberland River this home is between two public launch ramps Helm's Landing and Winfreys Ferry. Nestled on 9+ acres of fully fenced, gently rolling farmland, this property is the perfect blend of comfort, function, and rural beauty. Designed with both everyday

    Heather Flanagan Keller Williams Legacy Group

    5029 S Highway 379, Jamestown, KY 42629
  • /18

    $150,000

    Sold Jun 24, 2026

    106 Bunny Trail, Jamestown, KY 42629

    • Land
    • 6.49 Acres
    • $23,112 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 8 Days On Market

    Current Estimated Value $164,413

    Last Listing Agent Caleb Weaver PCS Real Estate

    106 Bunny Trail, Jamestown, KY 42629
    • /53

      Not Listed For Sale

      818 Woolen Mill Rd, Jamestown, KY 42629

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2021
      818 Woolen Mill Rd, Jamestown, KY 42629

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Sherri West Keller Williams Bluegrass Realty - Lake Cumberland

  • /6

    $29,900

    • Land
    • 1.1 Acres
    • $27,182 per Acre

    26 Arrowhead Ln, Jamestown, KY 42629

    What a beautiful piece of ground within 1 mile of Pleasant Hill Boat Ramp. 3 lots totaling 1.1 +/- acre bordering a seasonal small creek off Arrowhead Lane. Can build a dream home or can put 2-3 tiny homes and put on airBnB. Lots 26, 27, & 28

    Tina Clay CENTURY 21 Advantage Realty

    26 Arrowhead Ln, Jamestown, KY 42629
  • /67

    $191,000

    Sold Sep 30, 2025

    258 Dutton Cir, Jamestown, KY 42629

    • 3 Beds
    • 1 Bath
    • 1,560 Sq Ft
    • Built 1982

    Last Sold Summary

    • 13% Below List Price
    • $122/SF
    • 18 Days On Market

    Current Estimated Value $234,560

    Last Listing Agent Matthew Cooper Lake Cumberland Properties, Ltd. Co.

    258 Dutton Cir, Jamestown, KY 42629
    • /37

      Est $195,316

      Not Listed For Sale

      50 Pickett Ln, Jamestown, KY 42629

      • 3 Beds
      • 2 Baths
      • 1,008 Sq Ft
      • Built 1988
      50 Pickett Ln, Jamestown, KY 42629

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Whitney Marcum Lake Cumberland Properties, Ltd. Co.

  • /3

    $13,000

    $1K PRICE DROP
    • Land
    • 21,344 Sq Ft
    • $26,531 per Acre

    Lot 80 Captain's Point Subdivision, Jamestown, KY 42629

    Lot 80 of the Captain's Point Subdivision. Consist of 0.49 acres of land.

    Will Childers WTC Realty LLC

    Lot 80 Captain's Point Subdivision, Jamestown, KY 42629
  • /6

    $10,500

    Sold Sep 20, 2025

    11 Pickett Ln, Jamestown, KY 42629

    • Land
    • 19,166 Sq Ft
    • $23,864 per Acre

    Last Sold Summary

    • 5% Above List Price
    • 17 Days On Market

    Last Listing Agent MaKenzie Griffis GRATEFUL ACRES REALTY

    11 Pickett Ln, Jamestown, KY 42629
    • /14

      Not Listed For Sale

      8231 S Hwy 1680, Jamestown, KY 42629

      • 1 Bed
      • 2 Baths
      • 675 Sq Ft
      8231 S Hwy 1680, Jamestown, KY 42629

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Darren Gossage Weichert Realtors Ford Brothers, Inc.

  • /6

    $30,000

    • Land
    • 33,105 Sq Ft
    • $39,474 per Acre

    lot 115 Mooring Dr, Jamestown, KY 42629

    Great opportunity to build a new home in an upscale lake community on Lake Cumberland, that is only a 5 minute drive to launch your boat. This lot is mostly level with a gentle slope. This beautiful community is restricted to protect your investment! City water, electric and fiberoptics are available. Lake season is soon approaching, so take a look now and start building your vacation or

    Sherri West Lake Cumberland Real Estate Professionals

    lot 115 Mooring Dr, Jamestown, KY 42629
  • /3

    $90,000

    Sold Feb 03, 2026

    300 Helm Ln, Jamestown, KY 42629

    • Land
    • 17 Acres
    • $5,294 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 177 Days On Market

    Last Listing Agent Benjamin Karnes Patriot Realty - Auction LLC

    300 Helm Ln, Jamestown, KY 42629
    • /96

      Est $512,272

      Not Listed For Sale

      69 Harbor Dr, Jamestown, KY 42629

      • 5 Beds
      • 2.5 Baths
      • 2,845 Sq Ft
      • Built 2007
      69 Harbor Dr, Jamestown, KY 42629

      Last Sold Summary

      Last Listing Agent Tammy Stotts Southern Nest Realty, LLC

  • /13

    $149,000

    • Land
    • 13.38 Acres
    • $11,136 per Acre

    259 Rd, Jamestown, KY 42629

    13+ Acres of Natural Beauty Near Lake Cumberland... A rare opportunity to own 13+ beautiful acres near the headwaters of Lily Creek on Lake Cumberland. This property offers the perfect blend of privacy, natural beauty and convenience, with a stunning building site surrounded by mature trees and open land. Whether you're envisioning a permanent residence, a private weekend retreat, or a place to

    Kimberly Byrom Lake Cumberland Properties, Ltd. Co.

    259 Rd, Jamestown, KY 42629
  • /73

    $649,000

    Sold May 01, 2026

    111 Leveridge Ct, Jamestown, KY 42629

    • 5 Beds
    • 4.5 Baths
    • 6,500 Sq Ft
    • Built 2010

    Last Sold Summary

    • $100/SF
    • 5 Days On Market

    Current Estimated Value $687,795

    Last Listing Agent Justin McClure Coldwell Banker Legacy Group

    111 Leveridge Ct, Jamestown, KY 42629
    • /4

      Not Listed For Sale

      Lots 44&86 Heritage Trace, Jamestown, KY 42629

      Lots 44&86 Heritage Trace, Jamestown, KY 42629

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Vicki Sanders Coldwell Banker Larry Rogers

  • /35

    $189,500

    $36K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 932 Sq Ft

    145 State Park Rd Unit Q6, Jamestown, KY 42629

    Looking to RETIRE or just want to get away? This incredible opportunity offers a TURN KEY/FULLY FURNISHED townhome inside the gated Apple Valley RESORT that sits within the Lake Cumberland State Park and only 5 miles to the nearest boat dock, 2 restaurants overlooking the water, Lure Lodge, Hiking Trails and more! This is an incredible Investment Opportunity for anyone interested in an AirBnB,

    Amanda Long KELLER WILLIAMS HEARTLAND

    145 State Park Rd Unit Q6, Jamestown, KY 42629
  • /41

    $215,000

    Sold Apr 30, 2026

    2091 Clifty Creek Rd, Jamestown, KY 42629

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1980

    Last Sold Summary

    • 14% Below List Price
    • $175/SF
    • 25 Days On Market

    Current Estimated Value $276,500

    Last Listing Agent Tammy Hill Keller Williams Legacy Group

    2091 Clifty Creek Rd, Jamestown, KY 42629
    • /47

      Not Listed For Sale

      145 State Park Rd Unit E3, Jamestown, KY 42629

      • 2 Beds
      • 2 Baths
      • 900 Sq Ft
      • Built 1974
      145 State Park Rd Unit E3, Jamestown, KY 42629

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Torsten Langguth Keller Williams Commonwealth - Somerset

  • /22

    $13,000

    • Land
    • 41,382 Sq Ft
    • $13,684 per Acre

    88 Peninsula Blvd, Jamestown, KY 42629

    Build your dream home in The Peninsula on Lake Cumberland! This level to gently rolling, cleared lot is tucked away at the end of a dead-end road, offering added privacy and a peaceful setting. Located in a beautiful restricted, gated community with underground utilities, The Peninsula also offers a community hiking trail and boat storage for residents. Conveniently situated just minutes from

    Retina Duncan RE/MAX LakeTime Realty

    88 Peninsula Blvd, Jamestown, KY 42629
  • /50

    $167,500

    Sold May 20, 2026

    145 State Park Rd Unit A-3, Jamestown, KY 42629

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    Last Sold Summary

    • 9% Below List Price
    • $186/SF
    • 83 Days On Market

    Last Listing Agent Whitney Marcum Lake Cumberland Properties, Ltd. Co.

    145 State Park Rd Unit A-3, Jamestown, KY 42629
    • /8

      Est $160,000

      Not Listed For Sale

      000 Highway 1680, Jamestown, KY 42629

      000 Highway 1680, Jamestown, KY 42629

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent John David Golden Rule - Wilson Real Estate & Auction #2 LLC

  • /5

    $40,000

    • Land
    • 23,086 Sq Ft
    • $75,472 per Acre

    11 Cherry Loop, Jamestown, KY 42629

    Build your Lake Cumberland getaway in the established Cherry Hills community! Located just minutes from Pleasant Hill Boat Dock and launching ramp, this wooded lot offers a peaceful setting with the U.S. Army Corps of Engineers bordering the rear of the property, creating a natural buffer and added privacy. During the fall and winter months, enjoy seasonal views of Lake Cumberland while listening

    Whitney Marcum Lake Cumberland Properties, Ltd. Co.

    11 Cherry Loop, Jamestown, KY 42629
  • /44

    $168,000

    Sold Jan 30, 2026

    305 Glover Rd, Jamestown, KY 42629

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    Last Sold Summary

    • 14% Below List Price
    • $129/SF
    • 127 Days On Market

    Current Estimated Value $213,488

    Last Listing Agent Kim Arehart Weichert Realtors Ford Brothers, Inc.

    305 Glover Rd, Jamestown, KY 42629
    • /10

      Not Listed For Sale

      0 Twin Creek Estates Unit 24003445, Jamestown, KY 42629

      0 Twin Creek Estates Unit 24003445, Jamestown, KY 42629

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Lisa Coffey Weichert Realtors Ford Brothers, Inc.

  • /6

    $135,000

    • Land
    • 4.45 Acres
    • $30,337 per Acre

    35 Leveridge Ct, Jamestown, KY 42629

    Only 9 lots left in this beautiful 68-acre development. Paved streets. 1-13 acres available. All lots are heavily wooded. Restrictions allow for barndominiums, detached garages or buildings to accommodate boats and RV's. Located within a few miles of Jamestown Marina, State Dock Marina and Halcomb's Landing boat launch. Please watch for resident wildlife when driving through. Come check it out,

    Shelly Stoyell PCS Real Estate

    35 Leveridge Ct, Jamestown, KY 42629
  • /37

    $89,000

    Sold Jun 04, 2026

    3331 Highway 1058, Jamestown, KY 42629

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    Last Sold Summary

    • 26% Below List Price
    • $93/SF
    • 2 Days On Market

    Current Estimated Value $90,767

    Last Listing Agent GaVon Antle Golden Rule - Wilson Real Estate & Auction #2 LLC

    3331 Highway 1058, Jamestown, KY 42629
    • /7

      Not Listed For Sale

      101 Linkview Rd, Jamestown, KY 42629

      101 Linkview Rd, Jamestown, KY 42629

      Last Sold Summary

      • 176 Days On Market

      Last Listing Agent Sherri West Lake Cumberland Real Estate Professionals

  • /91

    $449,000

    $36K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,120 Sq Ft

    935 Clifty Creek Rd, Jamestown, KY 42629

    Lake Cumberland Log Home | 3,120 Sq Ft | Minutes to Two Boat Ramps. Whether you're searching for a full-time residence, weekend getaway, or family retreat, this one-of-a-kind log home offers the perfect combination of craftsmanship, space, and location. Situated just minutes from both Clifty Creek Boat Ramp and Holcomb's Landing at Wolf Creek Dam, you'll enjoy quick and convenient access to some

    Whitney Marcum Lake Cumberland Properties, Ltd. Co.

    935 Clifty Creek Rd, Jamestown, KY 42629
  • /29

    $75,000

    Sold Mar 06, 2026

    420 E Cumberland Ave, Jamestown, KY 42629

    • 2 Beds
    • 1 Bath
    • 696 Sq Ft

    Last Sold Summary

    • 16% Below List Price
    • $108/SF
    • 19 Days On Market

    Current Estimated Value $85,442

    Last Listing Agent Whitney Marcum Lake Cumberland Properties, Ltd. Co.

    420 E Cumberland Ave, Jamestown, KY 42629
    • /31

      Est $201,909

      Not Listed For Sale

      136 Bluegill Ln, Jamestown, KY 42629

      • 2 Beds
      • 1 Bath
      • 600 Sq Ft
      136 Bluegill Ln, Jamestown, KY 42629

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Whitney Marcum Lake Cumberland Properties, Ltd. Co.

  • /35

    $380,000

    New Construction $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,256 Sq Ft

    223 Pumpkin Creek Cir, Jamestown, KY 42629

    Situated on Pumpkin Creek Circle, this cabin offers an unbeatable location near Lake Cumberland State Resort Park and just minutes from Rowena Landing. Enjoy quick access to the water, nearby trails, and all the recreational opportunities that make Lake Cumberland one of the top lake destinations in the country. Ideal for both personal use or investment...short term rentals are welcome. Whatever

    Tina Clay CENTURY 21 Advantage Realty

    223 Pumpkin Creek Cir, Jamestown, KY 42629
  • /24

    $183,000

    Sold Jul 10, 2026

    8247 S Highway 379, Jamestown, KY 42629

    • 3 Beds
    • 1 Bath
    • 1,254 Sq Ft

    Last Sold Summary

    • 4% Below List Price
    • $146/SF
    • 33 Days On Market

    Current Estimated Value $189,252

    Last Listing Agent Nichole Bingham CENTURY 21 Advantage Realty

    8247 S Highway 379, Jamestown, KY 42629
    • /6

      Not Listed For Sale

      10 Mooring Dr, Jamestown, KY 42629

      10 Mooring Dr, Jamestown, KY 42629

      Last Sold Summary

      • 57 Days On Market

      Last Listing Agent Darren Gossage Weichert Realtors Ford Brothers, Inc.

  • /5

    $39,500

    • Land

    000 Town View Estates Unit LOTS 1 & 2, Jamestown, KY 42629

    Larry Sanner In The Loop Realty

    000 Town View Estates Unit LOTS 1 & 2, Jamestown, KY 42629
    • /24

      Est $129,434

      Not Listed For Sale

      65 Esto Rd, Jamestown, KY 42629

      • 2 Beds
      • 1 Bath
      • 1,040 Sq Ft
      65 Esto Rd, Jamestown, KY 42629

      Last Sold Summary

      • 90 Days On Market

      Last Listing Agent Charlotte Ikerd Key Players Real Estate

  • /62

    $524,900

    $24K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,800 Sq Ft

    148 Sandy Trail, Jamestown, KY 42629

    Welcome to this beautifully remodeled lakeview home, offering comfort, style, and year-round scenic charm. Nestled in a small, lake-oriented subdivision just off Boat Dock Road on the way to Jamestown Marina, this property is perfect for both full-time living or a relaxing getaway. This spacious home features 5 bedrooms and 2 bathrooms, highlighted by a stunning den with vaulted ceilings and

    Albert Hockensmith Lake And Land Realty Inc

    148 Sandy Trail, Jamestown, KY 42629

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