33

Jamestown, KY Homes for Sale under $600,000

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  • /31

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,937 Sq Ft

    70 Twin Creek Loop, Jamestown, KY 42629

    Welcome to 70 Twin Creek Loop in Jamestown, KY. It's where rustic charm meets modern comfort in this beautifully maintained 3-bedroom, 2-bath log cabin offering 1,937 square feet of inviting living space. Perfectly positioned just minutes from Lake Cumberland, this home is an ideal getaway, full-time residence, or retirement retreat for those seeking peace, privacy, and natural beauty. Step

    Agent Photo

    Christa Joynt

    Keller Williams Commonwealth

    70 Twin Creek Loop, Jamestown, KY 42629
  • /28

    $550,000

    • 8 Beds
    • 8 Baths

    786 Ray Man Rd, Jamestown, KY 42629

    Incredible Investment Opportunity in Wolf Creek Dam area! Are you looking for a property with endless possibilities? This modern motel offers a rare chance to own a prime piece of real estate in one of the most sought-after lake areas. Sitting on over 3 acres and featuring 8 fully furnished rooms, this property is truly one of a kind. Property Highlights: • 8 rooms - each with double queen beds •

    Rachel Bernard The Realty Firm

    786 Ray Man Rd, Jamestown, KY 42629
  • /55

    $379,900

    $15K PRICE DROP

    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
  • /56

    $325,000

    $10K PRICE DROP
    • 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
  • /63

    $375,000

    $24K PRICE DROP
    • 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
  • /40

    $327,500

    $18K PRICE DROP
    • 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
  • /24

    $479,900

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    8790 S Highway 127, Jamestown, KY 42629

    Experience the perfect blend of luxury, recreation, and privacy in this stunning 3,000 sq. ft. custom barndominium nestled on 1.8 serene, wooded acres and backing up to the beauty of Lake Cumberland. Designed for both elegant living and lake life, this exceptional property also could be a permanent residence or an Airbnb, featuring 1,500 sq. ft. of beautifully finished living space paired with an

    Christy Estep CENTURY 21 Advantage Realty

    8790 S Highway 127, 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
  • /63

    $559,800

    $135K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 3,500 Sq Ft

    1655 Kentucky 92, Jamestown, KY 42629

    Just minutes away from Lake Cumberland and the Jamestown Resort & Marina, this 3500 sq. ft. building is brimming with potential. Boasting two bathrooms and an ample parking area. Building would be a great residence with a little work or could be used as retail. The property's prime location and curb appeal make it a standout opportunity. On top of that, there's a 5-unit efficiency style

    Darren Gossage Weichert Realtors Ford Brothers, Inc.

    1655 Kentucky 92, Jamestown, KY 42629
  • /2

    $489,900

    • 6 Beds
    • 5 Baths
    • 4,788 Sq Ft

    100 Sunset Dr, Jamestown, KY 42629

    Discover an outstanding investment opportunity in Jamestown, Kentucky! Situated on 7.41 beautiful acres, this fully rented multi-unit property has a strong rental history and offers immediate income potential. The property features three separate rental units. Two units offer 2 bedrooms and 1.5 bathrooms, while the third unit includes 2 bedrooms and 1 bathroom. Each unit is individually metered

    Ryne Tolar Lake And Land Realty Inc

    100 Sunset Dr, Jamestown, KY 42629
  • /81

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft

    255 Tall Timber Dr, Jamestown, KY 42629

    Experience the best of both worlds: a peaceful 3 bedroom, 2 bath home that blends small-town convenience with the tranquility of nature. This Cape Cod style home features durable vinyl siding with T1-11accents giving it a modern look with classic appeal. Sitting on approximately .5 of an acre and just minutes from Lake Cumberland, there's plenty of room to spread out, garden, or simply enjoy the

    Debbie Loy Wilson Lake Cumberland Properties, Ltd. Co.

    255 Tall Timber Dr, Jamestown, KY 42629
  • /44

    $399,900

    • 3 Beds
    • 4 Baths
    • 2,463 Sq Ft

    67 Balcony Bend Rd, Jamestown, KY 42629

    Welcome to this charming Lake Cumberland retreat nestled on 1.12 private, wooded acres in a quiet lake community with no HOA. This property offers all the benefits of a 5 bedroom footprint at a highly competitive price point... 3 traditional bedrooms and 2 additional lower-level flex rooms furnished as bedrooms. Surrounded by mature trees and scenic beauty, this inviting home offers the perfect

    Kimberly Byrom Lake Cumberland Properties, Ltd. Co.

    67 Balcony Bend Rd, Jamestown, KY 42629
  • /91

    $410,000

    $79K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,042 Sq Ft

    1089 Warner Ridge Rd, Jamestown, KY 42629

    This beautiful 10 acre property offers everything you need for country living, featuring a barn with a full loft and stairs, concrete floors, water & electric, a feed and tack room, a turnout lot. The farmhouse, barn, and garages all have city water, and a circle driveway leads to the charming 3 bedroom, one bath home, which has been updated with refinished hardwood floors, new plumbing HVAC,

    Shelly Stoyell PCS Real Estate

    1089 Warner Ridge Rd, Jamestown, KY 42629
  • /33

    $365,000

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

    495 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

    495 Pumpkin Creek Cir, Jamestown, KY 42629
  • /44

    $399,900

    • 3 Beds
    • 2.5 Baths
    • 3,226 Sq Ft

    1125 S Highway 2284, Jamestown, KY 42629

    Discover the perfect blend of country living and multi-generational convenience in the beautiful Lake Cumberland area! Situated on 17.62 acres m/l, this spacious 3-bedroom, 2.5-bath home offers an ideal setup for two families with separate entrances to both the main level and the fully finished basement. The lower level features its own kitchen, separate washer and dryer hookups, and private

    Simon Wilson Golden Rule - Wilson Real Estate and Auction #1, LLC

    1125 S Highway 2284, 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,

    Larry Rogers Coldwell Banker Larry Rogers Realty, Inc

    404 Lorel Dunbar Rd, Jamestown, KY 42629
  • /98

    $475,000

    $20K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 6,048 Sq Ft

    223 Lakeview Dr, Jamestown, KY 42629

    Welcome to refined living in the highly sought-after Lily Creek Resort in Jamestown. This exceptional brick and vinyl residence offers an impressive blend of space, comfort, and thoughtful design—perfect for those who appreciate both elegance and functionality. With over 6,000 square feet of finished living space, this meticulously maintained home is designed for both everyday living and

    Elaine Rowlett Southern Nest Realty, LLC

    223 Lakeview Dr, Jamestown, KY 42629
  • /70

    $599,000

    Open Sat 8AM - 10AM $51K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,954 Sq Ft

    255 Lantern Way, Jamestown, KY 42629

    Welcome to Lake Cumberlands newest SHOW STOPPER! Better than new and thoughtfully designed, this 2023 modern craftsman blends luxury finishes, smart design, and timeless character right here in the heart of Jamestown, KY in the highly sought after gated community- The Oaks! Offering 4 bedrooms and 3 full baths. The main level features 10' ceilings, 8' doors, and European oak engineered hardwood

    Heather Flanagan Keller Williams Legacy Group

    255 Lantern Way, Jamestown, KY 42629
  • /52

    $319,900

    • 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
  • /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
  • /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
  • /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
  • /62

    $549,000

    • 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
  • /33

    $380,000

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

    443 Pumpkin Creek Rd, Jamestown, KY 42629

    Lot#15 1.175 Acres +/- 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

    Tina Clay CENTURY 21 Advantage Realty

    443 Pumpkin Creek Rd, Jamestown, KY 42629
  • /27

    $599,000

    • Land
    • 3.31 Acres
    • $180,967 per Acre

    000 Litton Dr, Jamestown, KY 42629

    Here's your chance to own an absolutely AMAZING 3.31-acre property with stunning lake views! Tucked away in the beautiful Lilly Creek Cove of Lake Cumberland, this spot is perfect for building the dream home you've always envisioned, complete with panoramic views of the water. Enjoy the perfect mix of seclusion while being just a stone's throw from Jamestown and the bustling Jamestown Marina.

    Darren Gossage Weichert Realtors Ford Brothers, Inc.

    000 Litton Dr, Jamestown, KY 42629
  • /47

    $380,000

    New Construction $20K PRICE DROP
    • 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
  • /23

    $499,900

    $50K PRICE DROP
    • Land
    • 2.4 Acres
    • $208,292 per Acre

    1243 N Main St, Creelsboro, KY 42629

    Introducing a brand-new open-span commercial building offering 10,200 square feet of versatile space, customize the layout to suit your business. Ideally positioned on 2.4 acres of land just before the 127 By-Pass in Jamestown. Ample acreage for parking, expansion, or outdoor storage. With dimensions of 85' x 120', this structure is designed for maximum flexibility—perfect for warehousing,

    Shelly Stoyell PCS Real Estate

    1243 N Main St, Creelsboro, KY 42629
  • /44

    $325,000

    • 5 Beds
    • 3 Baths
    • 2,750 Sq Ft

    143 Dylan Dr Unit 105, Jamestown, KY 42629

    The best surprise about this condo? It doesn't feel like one. Tucked among rolling hills, mature trees, and abundant green space, this spacious 5-bedroom, 3-bath townhome offers a rare sense of privacy and seclusion that's hard to find at Lake Cumberland. From the moment you arrive, you'll notice the peaceful setting and natural surroundings that make this property feel more like a private

    Bob Sophiea eXp Realty, LLC

    143 Dylan Dr Unit 105, 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
  • /72

    $379,000

    • 3 Beds
    • 2.5 Baths

    570 Little Indian Dr, Jamestown, KY 42629

    Welcome to your perfect getaway or full-time residence! This fully furnished 3BR/2BA home built in 2016 offers 1,152 sq ft of move-in ready living near Cumberland River and Lake Cumberland access. Included are queen bed, full bed, twin rollaway, office furniture, living room furniture, TV, dishes, washer/dryer, new carpet in 2 bedrooms, and remodeled master bath with walk-in shower and bench.

    Barbara McWhorter The Realty Firm - Byrdstown

    570 Little Indian Dr, Jamestown, KY 42629
  • /60

    $339,900

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

    334 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

    334 Sonny Aaron Dr Unit 335, Jamestown, KY 42629
  • /66

    $445,000

    Open Sat 12PM - 2PM $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 4,110 Sq Ft

    398 Carriage Ln, Jamestown, KY 42629

    Located in the gated community of The Oaks, 398 Carriage Lane offers over 4,000 finished square feet of living space on approximately 0.63 acres and is just minutes from Lake Cumberland and Jamestown Marina. This home features 3 bedrooms, 3 full bathrooms, and an additional room in the finished basement that is currently being used as a bedroom and includes a closet. The main level offers an

    Colton Flynn Keller Williams Commonwealth - Somerset

    398 Carriage Ln, Jamestown, KY 42629
  • /28

    $449,000

    New Construction
    • 4 Beds
    • 3 Baths
    • 1,816 Sq Ft

    141 Sonny Aaron Dr, Russell Springs, KY 42642

    Josh McKinley Mckinley Real Estate Group

    141 Sonny Aaron Dr, Russell Springs, KY 42642

Home Price Trends

Median Sale Price
$245,000
Median Single Family Sale Price
$281,000
Median Townhouse Sale Price
$335,000
Median 2 Bedroom Sale Price
$155,500
Average Price Per Sq Ft
$178
Number of Homes for Sale
36
Last 12 months Home Sales
39
Months of Supply
11.10
Median List Price
$295,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
12%
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