48

Homes in 42629 under $500,000

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  • /59

    $459,000

    $41K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 4,110 Sq Ft

    398 Carriage Ln, Jamestown, KY 42629

    Minutes to Lake Cumberland Marina | Gated Community | Located at 398 Carriage Lane in Jamestown, KY, this well-maintained home offers over 4,000 finished square feet of living space (more or less) and is situated on approximately .59 acres in the private, gated Oaks community. The home features 3 bedrooms with an additional room in the finished basement currently being used as a bedroom with a

    Ashley Stearnes CENTURY 21 Advantage Realty

    398 Carriage Ln, 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
  • /66

    $255,000

    $20K PRICE DROP
    • Land
    • 165 Acres
    • $1,545 per Acre

    0 S Highway 127 Unit LotWP001 22170345, Albany, KY 42602

    Escape to this stunning all-timber tract, ideally located near the serene Lake Cumberland, the iconic Wolf Creek Dam, and the Wolf Creek National Fish Hatchery. This property offers an exceptional blend of natural beauty and potential for your forever home or cabin, with mixed hardwood and softwood timber complemented by a tranquil creek running through it. Perfect for outdoor enthusiasts, the

    Joe Martin Whitetail Properties Real Estate

    0 S Highway 127 Unit LotWP001 22170345, Albany, KY 42602
  • /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
  • /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
  • /24

    $447,000

    $202K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,148 Sq Ft

    2794 Highway 1058, Jamestown, KY 42629

    A most perfect life can be lived right here. This property features a solid, older brick home with hardwood floors and a full, walkout basement, which is a wonderful place to come in to a warm, wood stove fire after tending the animals. The home boasts 3 bedrooms, plenty of closets, and a nicely remodeled bathroom. There's a perfect sitting porch, and a carport for the toys. A nice blacktop drive

    Ken Hill Patriot Realty - Auction LLC

    2794 Highway 1058, Jamestown, KY 42629
  • /24

    $269,000

    • Land
    • 50 Acres
    • $5,380 per Acre

    2820 Kentucky 1058, Jamestown, KY 42629

    An absolutely gorgeous property with beautiful farm views from its' highest points, nice open fields, wooded areas, and frontage on two blacktop roads: Ky Hwy 1058 and Helm Lane. There's something here for everyone, whether you dream of farming, or building that dream home with perfect views, and still having lots od room to explore. Water, power, and fiber optic Internet are available on both

    Ken Hill Patriot Realty - Auction LLC

    2820 Kentucky 1058, Jamestown, KY 42629
  • /70

    $329,000

    $30K PRICE DROP
    • 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
  • /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
  • /31

    $215,000

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft

    228 Cooper Rd, Jamestown, KY 42629

    Lake life meets peaceful country living in this charming Jamestown retreat just MINUTES from beautiful Lake Cumberland! If you’ve been dreaming of a place where you can relax, spread out, and enjoy the outdoors, this 3 bedroom, 2 full bathroom home checks all the right boxes! Situated on a permanent foundation and tucked away in a quiet rural setting, this home offers the perfect blend of

    Morgan Austin EXIT REALTY BLUEGRASS

    228 Cooper Rd, Jamestown, KY 42629
  • /40

    $335,000

    $10K 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
  • /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
  • /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
  • /56

    $210,000

    $35K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    145 State Park Rd Unit B5, Jamestown, KY 42629

    This beautifully updated 2 bed 2 bath condo offers easy living just minutes from the shores of Lake Cumberland. Features a fresh, modern interior including flooring, fixtures and finishes throughout. An open concept living and dining areas are perfect for entertaining or just relaxing after a day at the lake. Located in a peaceful, desirable neighborhood that can be used as a full time residence

    Scotty Carter Lake Cumberland Real Estate Professionals

    145 State Park Rd Unit B5, 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
  • /31

    $299,900

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

    456 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

    456 Pumpkin Creek Cir, Jamestown, KY 42629
  • /31

    $240,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,350 Sq Ft

    2440 S Highway 379, Jamestown, KY 42629

    Seize the opportunity to own a well-established Airbnb river retreat! Spanning 1.41 acres, this property is situated just 1 mile from Helm's Landing launch ramp and the Creelsboro store. Revel in the dual benefits of a revenue-generating home and a personal vacation haven—it's a logical choice! The retreat features 3 bedrooms, 2 full baths, and a spacious living room complete with a fireplace.

    Shelly Stoyell PCS Real Estate

    2440 S Highway 379, 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
  • /37

    $299,900

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

    488 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

    488 Pumpkin Creek Cir, Jamestown, KY 42629
  • /9

    $299,900

    • Land
    • 25.08 Acres
    • $11,958 per Acre

    3 Nelson Mill Rd, Jamestown, KY 42629

    Over 25 acres of open land that is ideal for development, farming, or other use. There are no zoning requirements. Offered 'As Is'.

    Gary Justice The Solutions Group KY, LLC

    3 Nelson Mill Rd, Jamestown, KY 42629
  • /35

    $299,900

    New Construction
    • 3 Beds
    • 1.5 Baths
    • 1,275 Sq Ft

    131 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

    131 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,

    Larry Rogers Coldwell Banker Larry Rogers Realty, Inc

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

    $495,000

    • 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
  • /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
  • /99

    $449,000

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

    935 Clifty Creek Rd, Jamestown, KY 42629

    Custom Log Home Near Lake Cumberland - Clifty Creek Rd, Jamestown, KY This custom log home on Clifty Creek Road in Jamestown, Kentucky, is a true showstopper! Conveniently located just down the road from two public boat ramps—Clifty Creek Ramp and Halcomb's Landing at Wolf Creek Dam—this home offers the perfect combination of natural beauty and accessibility to Lake Cumberland. From the moment

    Whitney Marcum Lake Cumberland Properties, Ltd. Co.

    935 Clifty Creek Rd, 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
  • /65

    $250,000

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

    532 Campbells Ferry Ln, Jamestown, KY 42629

    Price Reduction 30k - Very Motivated Seller - This property is Amazing and Price to Sell... Recent appraisal of $280k. Reach out today!!! Welcome to your perfect getaway in the highly desirable Campbell's Ferry Community area of Jamestown/Albany, KY on the Cumberland River Conveniently Located 5 miles from the Kendall Campground and Wolf Creek National Fish Hatchery, Halcomb's Landing Boat Ramp

    Barbara McWhorter The Realty Firm - Byrdstown

    532 Campbells Ferry Ln, Jamestown, KY 42629
  • /28

    $449,000

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

    140 Sonny Aaron Dr, Russell Springs, KY 42642

    Josh McKinley Mckinley Real Estate Group

    140 Sonny Aaron Dr, Russell Springs, KY 42642
  • /7

    $399,000

    • Land
    • 38 Acres
    • $10,500 per Acre

    Tract A U S 127, Jamestown, KY 42629

    Beautiful 38-acre unrestricted property offering exceptional development potential with dual access points from both Old Highway 127 and the new 127 Bypass. This versatile tract features a mix of rolling terrain and elevated ground, with the upper portion sitting high above the roadway—providing added privacy, scenic views, and a natural noise buffer. The land includes an abundance of mature,

    Shelly Stoyell PCS Real Estate

    Tract A U S 127, 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
  • /36

    $245,000

    $24K PRICE DROP
    • 2 Beds
    • 1 Bath

    612 Little Indian Dr, Jamestown, KY 42629

    Looking for the perfect little getaway near Wolf Creek Dam? This cozy home is located in a friendly community just 1/2 mile from the Cumberland River ramp and a little over a mile from Kendall Campground and the Lake Cumberland boat ramp at Halcomb's Landing! Property Details: 1,200 sq ft home, 2 bedrooms (1 with closet, 1 without) / 1 bath, Open-concept living room & kitchen, and Laundry room.

    Rachel Bernard The Realty Firm

    612 Little Indian Dr, Jamestown, KY 42629
  • /30

    $299,900

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

    234 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

    234 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
  • /37

    $295,000

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft

    394 W Cumberland Ave, Jamestown, KY 42629

    This is an exceptional investment opportunity waiting for you! This charming home features two bedrooms and one bathroom, offering roughly 800 square feet of inviting living space. The house has undergone a comprehensive remodel, showcasing a new roof, new flooring, an instant hot water heater, modern cabinets, and fresh siding. There is a new charging point for cars at the house. It makes for an

    Darren Gossage Weichert Realtors Ford Brothers, Inc.

    394 W Cumberland Ave, Jamestown, KY 42629
  • /33

    $299,900

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

    360 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

    360 Pumpkin Creek Cir, Jamestown, 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
  • /12

    $279,900

    $25K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,492 Sq Ft

    120 W Cumberland Ave, Jamestown, KY 42629

    Duplex one Block from three New Restaurants.. Minutes from Jamestown Marina largest House Boat Lake in the USA. Lots of trailer and RV parking space. MPJamestown Ky City Limits has no Zoning!!

    Larry Sanner In The Loop Realty

    120 W Cumberland Ave, Jamestown, KY 42629
  • /35

    $299,900

    New Construction
    • 3 Beds
    • 1.5 Baths
    • 1,275 Sq Ft

    197 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

    197 Pumpkin Creek Cir, Jamestown, KY 42629

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