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Jamestown

Jamestown, Kentucky is located within Russell County and serves as the county seat. Considered the gateway to outdoor adventure with its access to Lake Cumberland and the Cumberland River and perhaps best known for being the houseboat capital of the world. Weather you enjoy boating, fishing, houseboat rentals or cabin rentals…there’s something for everyone to enjoy on or around the water. Take a break from the sun and enjoy the quaint and charming downtown, locally known as the “Jamestown Square”. At the heart of the square stands the doughboy, a monument dedicated to the fallen men and women of Russell County who have served our country. The square is host to several annual street festivals and has recently undergone a revitalization of many of the historic buildings, resulting in several new, local dining options.

Min. Price
Max. Price
Beds
Baths
1360 State Highway 92 Jamestown, KY 42629
$2,299,000
5 Beds 6 Baths 10,076 SqFt Listing No. 25011161 Property Type: House camera (84) Courtesy of: Lake Cumberland Properties, Ltd. Co.
Details
33 Trey Drive Jamestown, KY 42629
$789,000
5 Beds 4 | 2 Baths 3,600 SqFt Listing No. 26022262 Property Type: House camera (78) Courtesy of: Lake Cumberland Properties, Ltd. Co.
Details
905 Lily Creek Resort Road Jamestown, KY 42629
$675,000
5 Beds 4 | 1 Baths 3,796 SqFt Listing No. 25507787 Property Type: House camera (72) Courtesy of: Lake Cumberland Properties, Ltd. Co.
Details
556 Murphy Lane Jamestown, KY 42629
$599,999
4 Beds 4 Baths 2,908 SqFt Listing No. 26011279 Property Type: House camera (52) Courtesy of: Lake Cumberland Properties, Ltd. Co.
Details
106 Pleasant Hill Road Jamestown, KY 42629
$525,000
2 Beds 3 Baths 1,815 SqFt Listing No. 26028756 Property Type: House camera (98) Courtesy of: Lake Cumberland Properties, Ltd. Co.
Details
100 Ballenger Spur Road Jamestown, KY 42629
$495,000
- - - Listing No. 26025095 Property Type: Commercial camera (41) Courtesy of: Lake Cumberland Properties, Ltd. Co.
Details
134 Finn Way Jamestown, KY 42629
$397,000
4 Beds 2 Baths 1,374 SqFt Listing No. 26023761 Property Type: House camera (42) Courtesy of: Lake Cumberland Properties, Ltd. Co.
Details
255 Tall Timber Drive Jamestown, KY 42629
$350,000
3 Beds 2 Baths 1,450 SqFt Listing No. 26015441 Property Type: House camera (81) Courtesy of: Lake Cumberland Properties, Ltd. Co.
Details
56 Lily Creek Court Jamestown, KY 42629
$335,000
3 Beds 2 Baths 1,530 SqFt Listing No. 26007658 Property Type: House camera (42) Courtesy of: Lake Cumberland Properties, Ltd. Co.
Details
120 Ivy Drive Jamestown, KY 42629
$327,500
3 Beds 2 Baths 1,800 SqFt Listing No. 26004534 Property Type: House camera (40) Courtesy of: Lake Cumberland Properties, Ltd. Co.
Details
1055 KY-92 Jamestown, KY 42629
$299,000
3 Beds 2 Baths 1,248 SqFt Listing No. 26003642 Property Type: House camera (54) Courtesy of: Lake Cumberland Properties, Ltd. Co.
Details
227 Little Louisville Road Jamestown, KY 42629
$285,000
6 Beds 4 Baths 2,781 SqFt Listing No. 26013621 Property Type: House camera (41) Courtesy of: Lake Cumberland Properties, Ltd. Co.
Details
 1360 State Highway 92, Jamestown, KY 42629
camera (84)
price

$2,299,000

beds

5 5 Beds

baths

6 6 Baths

lot size

10,076 SqFt 10,076 SqFt

listing no.

25011161 Listing No. 25011161

property type

House Property Type: House

gallery photos

camera (84)

Courtesy of: Lake Cumberland Properties, Ltd. Co.

 33 Trey Drive, Jamestown, KY 42629
camera (78)
price

$789,000

beds

5 5 Beds

baths

4 | 2 4 | 2 Baths

lot size

3,600 SqFt 3,600 SqFt

listing no.

26022262 Listing No. 26022262

property type

House Property Type: House

gallery photos

camera (78)

Courtesy of: Lake Cumberland Properties, Ltd. Co.

 905 Lily Creek Resort Road, Jamestown, KY 42629
camera (72)
price

$675,000

beds

5 5 Beds

baths

4 | 1 4 | 1 Baths

lot size

3,796 SqFt 3,796 SqFt

listing no.

25507787 Listing No. 25507787

property type

House Property Type: House

gallery photos

camera (72)

Courtesy of: Lake Cumberland Properties, Ltd. Co.

 556 Murphy Lane, Jamestown, KY 42629
camera (52)
price

$599,999

beds

4 4 Beds

baths

4 4 Baths

lot size

2,908 SqFt 2,908 SqFt

listing no.

26011279 Listing No. 26011279

property type

House Property Type: House

gallery photos

camera (52)

Courtesy of: Lake Cumberland Properties, Ltd. Co.

 106 Pleasant Hill Road, Jamestown, KY 42629
camera (98)
price

$525,000

beds

2 2 Beds

baths

3 3 Baths

lot size

1,815 SqFt 1,815 SqFt

listing no.

26028756 Listing No. 26028756

property type

House Property Type: House

gallery photos

camera (98)

Courtesy of: Lake Cumberland Properties, Ltd. Co.

 100 Ballenger Spur Road, Jamestown, KY 42629
camera (41)
price

$495,000

beds

- -

baths

- -

lot size

- -

listing no.

26025095 Listing No. 26025095

property type

Commercial Property Type: Commercial

gallery photos

camera (41)

Courtesy of: Lake Cumberland Properties, Ltd. Co.

 134 Finn Way, Jamestown, KY 42629
camera (42)
price

$397,000

beds

4 4 Beds

baths

2 2 Baths

lot size

1,374 SqFt 1,374 SqFt

listing no.

26023761 Listing No. 26023761

property type

House Property Type: House

gallery photos

camera (42)

Courtesy of: Lake Cumberland Properties, Ltd. Co.

 255 Tall Timber Drive, Jamestown, KY 42629
camera (81)
price

$350,000

beds

3 3 Beds

baths

2 2 Baths

lot size

1,450 SqFt 1,450 SqFt

listing no.

26015441 Listing No. 26015441

property type

House Property Type: House

gallery photos

camera (81)

Courtesy of: Lake Cumberland Properties, Ltd. Co.

 56 Lily Creek Court, Jamestown, KY 42629
camera (42)
price

$335,000

beds

3 3 Beds

baths

2 2 Baths

lot size

1,530 SqFt 1,530 SqFt

listing no.

26007658 Listing No. 26007658

property type

House Property Type: House

gallery photos

camera (42)

Courtesy of: Lake Cumberland Properties, Ltd. Co.

 120 Ivy Drive, Jamestown, KY 42629
camera (40)
price

$327,500

beds

3 3 Beds

baths

2 2 Baths

lot size

1,800 SqFt 1,800 SqFt

listing no.

26004534 Listing No. 26004534

property type

House Property Type: House

gallery photos

camera (40)

Courtesy of: Lake Cumberland Properties, Ltd. Co.

 1055 KY-92, Jamestown, KY 42629
camera (54)
price

$299,000

beds

3 3 Beds

baths

2 2 Baths

lot size

1,248 SqFt 1,248 SqFt

listing no.

26003642 Listing No. 26003642

property type

House Property Type: House

gallery photos

camera (54)

Courtesy of: Lake Cumberland Properties, Ltd. Co.

 227 Little Louisville Road, Jamestown, KY 42629
camera (41)
price

$285,000

beds

6 6 Beds

baths

4 4 Baths

lot size

2,781 SqFt 2,781 SqFt

listing no.

26013621 Listing No. 26013621

property type

House Property Type: House

gallery photos

camera (41)

Courtesy of: Lake Cumberland Properties, Ltd. Co.

© 2026 ImagineMLS. All rights reserved.
The data relating to real estate for sale on this website comes in part from the Internet Data Exchange Program of the ImagineMLS. Real estate listings held by IDX Brokerage firms other than Lake Cumberland Properties, Ltd. Co. are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX Brokers. The Broker providing this data believes it to be correct, but advises interested parties to confirm them before relying on them in a purchase decision.
ImagineMLS data last updated at November 9, 2026, 3:57 AM ET
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