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$415,000
3 Beds ⋅ 3 Baths
Beautifully updated and maintained Colonial home in Dogwood Village. This spacious home offers nearly 2000 square feet of living plus a basement area. There is an attached 2 car garage and both a screened porch and open deck at the rear of the home. A fireplace in the living room adds warmth to cool fall and winter days. The rear of the home is accented by both spacious screened porch and an open deck. Perfect location with easy access to highways and tax free shopping in Middletown.

189 Birchwood, Galena

Listing courtesy of L. C. Parker Real Estate. Contact:

$740,000
3 Beds ⋅ 3 Baths
Welcome to your Eastern Shore oasis, an impressive nearly 3,700-square-foot home offering river access on almost 2 acres, a boat slip, stunning water views, and beautifully established grounds surrounded by mature trees. Inside, you’ll find a dramatic two-story foyer, hardwood floors, a designer kitchen with granite countertops and an oversized walk-in pantry, multiple living spaces, a wood-burning fireplace, and an enclosed sunroom overlooking the water. Step outside to the expansive Trex deck with a recessed hot tub, then follow the path directly to the river. With three bedrooms, three full bathrooms, a walkout lower level, two bonus space, and a two-car garage, this home delivers the space, finishes, and lifestyle you’ve been waiting for. Schedule your private tour today and experience this waterfront retreat for yourself. Furniture is available for purchase as well!

14540 Stirrup Lane Ln, Galena

Listing courtesy of Keller Williams Flagship. Contact:

$1,595,000
4 Beds ⋅ 2 Baths
Enjoy sweeping water views, a bulkheaded shoreline, and a lawn extending to the water's edge—an exceptional and hard-to-find combination. Boating enthusiasts will appreciate the private dock, complete with a boat lift and Jet Ski lift and the location on the river. This charming four-bedroom home blends timeless character with everyday functionality. The thoughtfully designed floor plan features a first-floor primary suite, hardwood floors throughout, and spacious living areas ideal for both relaxing and entertaining. The detached garage includes a private apartment with an additional bedroom and an additional full bathroom, offering excellent space for guests or extended family. Including the garage apartment, this property has 5 bedrooms and 3 full baths, The expansive kitchen and living area open through sliding glass doors to a patio, screened porch, and beautifully landscaped lawn all overlooking the water, creating seamless indoor-outdoor living with broad water views. Mature trees provide shade, beauty, and privacy throughout the property. Conveniently located just minutes from Georgetown, you'll enjoy easy access to restaurants and a sought-after boating destination. Whether your passion is waterskiing, wakeboarding, paddleboarding, fishing, or peaceful kayaking, this location offers endless opportunities to enjoy life on the water. This is a property that truly should be experienced in person to appreciate its unique setting, exceptional amenities, and waterfront lifestyle.

14046 Tockwogh Ln, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

$325,000
3 Beds ⋅ 2 Baths
136 N Main St is Coming Soon in Galena! Your next home may be closer than you think. This inviting Colonial combines classic character with thoughtful updates across nearly 1,900 square feet of living space. Inside, you'll find three comfortable bedrooms, one full bath upstairs, a convenient main-level half bath, a bright kitchen with an easy flow into the main living areas, and a dedicated laundry/mudroom that adds everyday convenience. Outside, the fully fenced backyard offers exceptional space to enjoy, complete with mature shade trees, a fire pit, a storage shed, and plenty of room for outdoor gatherings, gardening, pets, or play. A large paved driveway provides abundant off-street parking. Conveniently located near Rt. 301, Chestertown, Middletown, local marinas, shopping, and dining, this home offers the charm of small-town living with easy access to everyday essentials. Stay tuned, you'll want to be among the first to see it when it hits the market.

136 N Main St, Galena

Listing courtesy of Keller Williams Legacy. Contact: 4436609229
$399,800
4 Beds ⋅ 3 Baths
WOW! What a transformation of this sturdy Four Square Colonial nestled in a peaceful small-town setting. Enjoy the convenience of being within walking distance to parks, schools, the post office, and local markets while still having the space and privacy of an oversized nearly half-acre lot. The exterior features a detached oversized two-car garage with pull-through access to the HUGE backyard — perfect for entertaining, gardening, or future outdoor projects. A brand-new roof has just been installed on both the home and garage, adding even more value and peace of mind. Inside, the home has undergone a complete top-to-bottom renovation while maintaining the charm and solid craftsmanship of a bygone era. The stunning new interior includes an open-concept main level, all-new kitchen and baths, updated flooring, fresh drywall, neutral designer paint throughout, and brand-new appliances. Comfort is covered year-round with newly installed central heating and air conditioning. The fabulous primary suite offers a true retreat with a custom glass-enclosed shower and beautifully updated finishes. Additional highlights include a full dry basement offering excellent storage. This home truly offers the best of both worlds — the beauty and convenience of new construction combined with the timeless quality and character of a classic colonial. Put this one at the top of your list to tour soon!

122 Main St, Galena

Listing courtesy of Village Real Estate Company LLC. Contact: