18

Jamestown, KY Homes for Sale under $400,000

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  • /66

    $389,900

    • 3 Beds
    • 3.5 Baths
    • 2,657 Sq Ft

    120 Cole Rd, Jamestown, KY 42629

    Welcome to your Lake Cumberland retreat in the desirable Caney Cove subdivision! This beautifully updated 3-bedroom, 3.5-bath home sits on three lots and offers a rare keyhole view of the lake—perfect for those seeking a peaceful getaway. Major improvements have already been taken care of, including a new roof (2022), with HVAC and water heater only 8 years old—offering peace of mind for years to

    Agent Photo

    Jessica Vincent

    CENTURY 21 Advantage Realty

    (270) 918-1457

    120 Cole Rd, Jamestown, KY 42629
  • /46

    $365,000

    • 3 Beds
    • 2.5 Baths
    • 1,350 Sq Ft

    495 Pumpkin Creek Cir, Jamestown, KY 42629

    Barbara McWhorter The Realty Firm - Byrdstown

    495 Pumpkin Creek Cir, Jamestown, KY 42629
  • /55

    $379,900

    570 Little Indian Dr, Jamestown, KY 42629

    Welcome to your perfect getaway or full-time residence! This 3 bedroom, 2 bathroom home offers comfort, convenience, and incredible outdoor living-all in a unique, private setting just minutes from the water. Built in 2016 and maintained in pristine, move-in ready condition, this 1,152 sq ft home comes fully furnished, making it truly turnkey. Inside, you'll find a warm and inviting interior

    Rachel Bernard The Realty Firm

    570 Little Indian Dr, Jamestown, KY 42629
  • /63

    $399,000

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft

    554 N Main St, Jamestown, KY 42629

    A staple in Jamestown since the 1930s, this offers exceptional curb appeal and a fantastic location. It features an inviting covered front and side porch, providing a welcoming entry. Inside, you'll find original hardwood floors, a clawfoot tub, and exquisite woodworking that highlight the home's historical charm. Over the years, tasteful updates have been made, preserving the unique character of

    Shelly Stoyell PCS Real Estate

    554 N Main St, Jamestown, KY 42629
  • /64

    $375,000

    • 4 Beds
    • 4 Baths
    • 2,100 Sq Ft

    370 Wesley Cir, Jamestown, KY 42629

    Experience effortless lake living in this fully furnished, turn-key 4-bedroom, 4-bath lake house ideally located just minutes from the marina and two public launching ramps. Presently this cabin is a vacation home/short term rental property. Designed for comfort and convenience, the home features two spacious primary suites, making it perfect for hosting family, friends, or guests. The living

    Kimberly Byrom Lake Cumberland Properties, Ltd. Co.

    370 Wesley Cir, Jamestown, KY 42629
  • /35

    $399,900 New Construction

    • 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
  • /47

    $399,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,256 Sq Ft

    255 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

    255 Pumpkin Creek Cir, Jamestown, KY 42629
  • /29

    $399,000

    • 5 Beds
    • 2 Baths
    • 2,570 Sq Ft

    404 Lorel Dunbar Rd, Jamestown, KY 42629

    LAKE FRONT!! Located in the Pleasant Hill community, this 5-bedroom, 2-bathroom residence offers a rare combination of lakefront living and functional space. The home sits on 0.41 acres of prime lakefront property and features extensive updates, including a oversized deck designed for entertaining and a hot tub for relaxation. With its close proximity to the Pleasant Hill Boat Ramp and its quiet,

    Vicki Sanders Coldwell Banker Larry Rogers

    404 Lorel Dunbar Rd, Jamestown, KY 42629
  • /76

    $349,999

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

    139 Payton Ln, Jamestown, KY 42629

    Claim your own piece of paradise down a quiet gravel lane in Russell County, Kentucky. Privacy and seclusion is yours in this quaint lake cottage, nestled in dense woods high above the convergence of Wolf Creek, Lily Creek and Caney Creek on Lake Cumberland. This home has been gently loved for decades by the current owners. The roof of the house was replaced in summer, 2025. The detached two-car

    Charlotte Ikerd Key Players Real Estate

    139 Payton Ln, Jamestown, KY 42629
  • /57

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,723 Sq Ft

    186 Lily Creek Resort Rd, Jamestown, KY 42629

    If you've been searching for a truly one-of-a-kind home in the Lake Cumberland area, this is it. Completed at the end of 2024, this custom-built property still feels brand new. Lightly lived in and meticulously maintained, offering that sought-after new construction look, feel, and even smell. Situated in the desirable Lily Creek Resort community in Jamestown, Kentucky, this property also

    Matthew Fouch Keller Williams Commonwealth - Somerset

    186 Lily Creek Resort Rd, Jamestown, KY 42629
  • /70

    $329,000

    • 5 Beds
    • 2 Baths
    • 2,340 Sq Ft

    65 Wooldridge Rd, Jamestown, KY 42629

    Discover this absolute stunning 5-bedroom, 2-bath home, offering endless possibilities as a short-term rental or primary residence. Located just 5 miles from the breathtaking Lake Cumberland and conveniently close to town, this spacious 2,500 sq ft property blends original charm with modern upgrades. The owners mastered the task of transforming a vintage structure (formerly a church) into a

    Jill Johnson Eagle Realty & Development LLC

    65 Wooldridge Rd, Jamestown, KY 42629
  • /35

    $315,000

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

    66 Deer Run Ln, Jamestown, KY 42629

    Well-maintained single-story ranch home, located 2.6 miles from Safe Harbour Jametown marina on beautiful Lake Cumberland. 3 bedrooms, 2 full baths, full laundry hookups. Open concept, great room, dining room and kitchen makes this home feel much bigger than the square footage with indicate. All bedrooms have large closets, the primary bedroom has an on-suite bath complete with a custom tiled

    Aaron Schork Champion Properties

    66 Deer Run Ln, Jamestown, KY 42629
  • /40

    $345,000

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

    120 Ivy Dr, Jamestown, KY 42629

    ONE LEVEL LIVING...Enjoy the easy flow of this brick ranch...ideal for so many. This thoughtfully designed home features vaulted ceilings in both the living room and the spacious primary bedroom suite. A bright and versatile flex room-recently used as an inspiring home office-offers abundant windows and direct access to a lovely rear patio, perfect for relaxing in the private backyard. Located on

    Kimberly Byrom Lake Cumberland Properties, Ltd. Co.

    120 Ivy Dr, Jamestown, KY 42629
  • /35

    $319,000

    • 3 Beds
    • 2.5 Baths
    • 2,208 Sq Ft

    2390 W Highway 92, Jamestown, KY 42629

    One doesn't just buy a home like this, it becomes a part of you, and you become a part of the history that surrounds this great place. Known locally and the "Phelps Acres" home, this gorgeous 151 year old home was built on land that was conveyed to the Phelps family via a land grant for the elder Phelps' service in the American Revolution. In 1875 this amazing home purportedly replaced earlier

    Ken Hill Patriot Realty - Auction LLC

    2390 W Highway 92, Jamestown, KY 42629
  • /51

    $359,000

    • 4 Beds
    • 3.5 Baths
    • 3,300 Sq Ft

    109 Dylan Dr Unit 101, Jamestown, KY 42629

    Welcome to 109 Dylan Dr. Unit 101 in Lily Creek Resort—this spacious 2-story townhome with a finished basement offers 4 bedrooms, 3.5 bathrooms, and the perfect blend of comfort, updates, and lake-area living! Conveniently located just 2.5 miles from Jamestown Resort & Marina, you'll have quick access to Lake Cumberland for all your boating and summer fun. Recent updates include a beautifully

    Paige Botts Eagle Realty & Development LLC

    109 Dylan Dr Unit 101, Jamestown, KY 42629
  • /54

    $314,000

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1055 Kentucky 92, Jamestown, KY 42629

    Turnkey Lake Home on 1.3 Unrestricted Acres - Minutes to Jamestown Marina Fully updated and move-in ready, this lake-area home offers the perfect blend of convenience, privacy, and rental potential. Located on the way to Jamestown Marina, the 1.3 unrestricted acres provide plenty of space for entertaining, parking boats or RVs, and future expansion. The property features a detached two-car

    Whitney Marcum Lake Cumberland Properties, Ltd. Co.

    1055 Kentucky 92, Jamestown, KY 42629
  • /42

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,530 Sq Ft

    56 Lily Creek Ct, Jamestown, KY 42629

    Located in the highly sought-after Lily Creek Resort, this 3 bedroom, 2 bath home offers the ideal blend of lake convenience, community amenities, and comfortable living. Situated just off Hwy 92 and approximately 4 miles from Jamestown Resort & Marina, this property places you right in the heart of Lake Cumberland recreation while still offering a peaceful, established neighborhood setting. Lily

    Whitney Marcum Lake Cumberland Properties, Ltd. Co.

    56 Lily Creek Ct, Jamestown, KY 42629
  • /60

    $339,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft

    335 Sonny Aaron Dr Unit 335, Jamestown, KY 42629

    Come Home To Sonny's Landing!!! New Construction Home situated on a nice large lot just minutes from Lake Cumberland. This home has it all!!! Call Today For More Info!!!

    Josh McKinley Mckinley Real Estate Group

    335 Sonny Aaron Dr Unit 335, Jamestown, KY 42629

Home Trends in Jamestown, KY

Housing Trends

Median Sale Price
$269,000
Median Single Family Sale Price
$270,000
Median Townhouse Sale Price
$501,950
Average Price Per Sq Ft
$178
Number of Homes for Sale
30
Last 12 months Home Sales
35
Months of Supply
10.30
Median List Price
$295,000
Median Change From 1st List Price
11%
Median Home Sale Price YoY Change
25%
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