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143 Dylan Dr Unit #105, Jamestown
$325,000
5 Beds ⋅ 3 Baths ⋅ 26009224 MLS
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 retreat than a typical condominium. The expansive partially covered deck is the perfect place to start your day with a cup of coffee, unwind after a day on the lake, or gather with family and friends while enjoying the sights and sounds of nature. Surrounded by trees and thoughtfully positioned within the community, the outdoor living space feels surprisingly private and inviting. With approximately 2,750 square feet of finished living space, including a finished lower level, there's plenty of room for weekend guests, extended family, or full-time living. Multiple living areas provide flexibility for entertaining, relaxing, or creating dedicated spaces for hobbies and recreation. A 1-car attached garage and separate lower-level golf cart garage offer added convenience and storage for all your lake-life essentials. Residents also enjoy access to community amenities including a pool and tennis/basketball courts. Located just minutes from Lily Creek Boat Ramp and Jamestown Marina, you'll enjoy quick access to some of the best boating and recreation Lake Cumberland has to offer, while still appreciating the tranquility of being just outside town. Whether you're searching for a weekend escape, vacation home, or primary residence, this property offers the space, setting, and lifestyle that make Lake Cumberland such a special place to call home.

143 Dylan Dr Unit #105, Jamestown

255 Tall Timber Dr, Jamestown
$350,000
3 Beds ⋅ 2 Baths ⋅ 26015441 MLS
Lake living meets modern comfort in this beautiful 2021 Cape Cod home! Nestled on approximately 0.5 acres in a peaceful, lake-oriented neighborhood, this 3-bedroom, 2-bath home offers the perfect blend of privacy, convenience, and outdoor adventure—just 2 miles from Safe Harbor Marina on beautiful Lake Cumberland. From the moment you arrive, you'll appreciate the home's charming curb appeal, featuring durable vinyl siding with T1-11 accents that create a timeless yet modern look. Inside, the thoughtfully designed 1,590-square-foot floor plan offers one bedroom on the main level and two spacious bedrooms upstairs, providing flexibility for family, guests, or a home office. The kitchen is equipped with high-end appliances, all less than five years old, making everyday living and entertaining effortless. Enjoy partial lake views while relaxing on the screened-in porch—the perfect place for your morning coffee, evening sunsets, or gathering with friends. Step outside to your own backyard retreat, complete with a beautifully designed firepit area that's ideal for making memories after a day on the lake. A 24x30 detached garage provides plenty of room for vehicles, boats, golf carts, or other lake toys, while the 10x16 storage shed offers additional space for tools and equipment. Whether you're looking for a full-time residence, weekend getaway, or investment property, this home checks all the boxes. For those wanting a truly turnkey experience, furnishings are negotiable. Don't miss this opportunity to own a newer home in one of the area's most desirable lake communities. Schedule your private showing today and start enjoying the Lake Cumberland lifestyle!

255 Tall Timber Dr, Jamestown

56 Lily Creek Ct, Jamestown
$335,000
3 Beds ⋅ 2 Baths ⋅ 26007658 MLS
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 Creek Resort is known for its well-maintained surroundings and desirable amenities, including a community swimming pool, tennis court, and basketball court—making it a great fit for both full-time living and weekend getaways. Opportunities to own in this neighborhood are limited, adding to the long-term value and appeal. A rare bonus with this property is the additional lot included, offering flexibility for future building, added privacy, or potential resale. Inside, the home features an open concept layout with abundant natural light, creating an inviting space for gathering and entertaining. The main level offers a primary bedroom with walk-in closet, full bath, and a functional laundry area with extra storage. Upstairs includes two guest bedrooms, an additional full bath, and access to a private upper-level deck. Outdoor living is a highlight with a wraparound main-level deck and an additional upper deck—perfect for enjoying the surroundings. A new storage shed (2025) provides convenient space for lawn equipment or lake gear. With its prime location near the marina, desirable neighborhood amenities, and added lot value, this property presents an excellent opportunity for a lake home, investment, or full-time residence. Restrictions and HOA apply.

56 Lily Creek Ct, Jamestown