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Luxury deep water retreat on the Sassafras River: an exceptional custom waterfront crafted residence Offering expansive river views, a private deep-water pier, resort style amenities and distinctive natural timber architectural. The custom log construction adds warmth, character and architectural distinction throughout the home The current owners had their 70 ft boat docked there for 10 years with space for several boats to be docked as well. INDOOR POOL looking to the outdoors, situated on a DOUBLE LOT, with a glass enclosure and loads of space to entertain! There are 2 separate upper-level quarters, one for guests which includes a family room, sitting room and full bath. So much potential to utilize at least 2 of the rooms for bedrooms. The primary suite on the other side of the home includes 2 walk-in closets, a dressing room. full bath with soaking tub, an office space and a sitting area with waterfront views. 3 bedrooms with potential to have 5 bedrooms. Set on the tranquil shores of the Sassafras River, this striking custom-built home, blends timeless craftsmanship with resort-style amenities—perfect for effortless entertaining and relaxed waterfront living. The great room includes soaring beams, walls of glass, and panoramic river views Deep water frontage with private pier, 3,000 lb. boat lift and ideal for larger boats as well, crabbing, fishing, and sunset cruising. Year‑round indoor pool pavilion with lounge seating, beverage bar, and easy walk-out. Chef’s kitchen featuring premium appliances, expansive island, and seamless flow to dining and outdoor spaces. Multiple decks and patios for al fresco dining, plus level lawn to the water’s edge. There is even a small kitchenette in the garage for those hardcore entertainers! A full house generator is also present and 3 HVAC units to cool the home. This home would make an amazing Air B and B! There is an additional cabin with sleeping bunks and amenities for those overnight guests that never want to leave. Please click on the walkthrough tour and floor plans are also available.

4 Beds ⋅ 4 Baths

Luxury deep water retreat on the Sassafras River: an exceptional custom waterfront crafted residence Offering expansive river views, a private deep-water pier, resort style amenities and distinctive natural timber architectural. The custom log construction adds warmth, character and architectural distinction throughout the home The current owners had their 70 ft boat docked there for 10 years with space for several boats to be docked as well. INDOOR POOL looking to the outdoors, situated on a DOUBLE LOT, with a glass enclosure and loads of space to entertain! There are 2 separate upper-level quarters, one for guests which includes a family room, sitting room and full bath. So much potential to utilize at least 2 of the rooms for bedrooms. The primary suite on the other side of the home includes 2 walk-in closets, a dressing room. full bath with soaking tub, an office space and a sitting area with waterfront views. 3 bedrooms with potential to have 5 bedrooms. Set on the tranquil shores of the Sassafras River, this striking custom-built home, blends timeless craftsmanship with resort-style amenities—perfect for effortless entertaining and relaxed waterfront living. The great room includes soaring beams, walls of glass, and panoramic river views Deep water frontage with private pier, 3,000 lb. boat lift and ideal for larger boats as well, crabbing, fishing, and sunset cruising. Year‑round indoor pool pavilion with lounge seating, beverage bar, and easy walk-out. Chef’s kitchen featuring premium appliances, expansive island, and seamless flow to dining and outdoor spaces. Multiple decks and patios for al fresco dining, plus level lawn to the water’s edge. There is even a small kitchenette in the garage for those hardcore entertainers! A full house generator is also present and 3 HVAC units to cool the home. This home would make an amazing Air B and B! There is an additional cabin with sleeping bunks and amenities for those overnight guests that never want to leave. Please click on the walkthrough tour and floor plans are also available.

31436 Sassafras River Ave, Galena

Listing courtesy of EXP Realty, LLC. Contact:

$1,595,000

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.

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:

$1,500,000

Impressive Masterpiece on Swantown Creek with 2 Boat Lifts! Exquisitely Crafted, the high quality upgrades have created an oasis for serenity, relaxation and entertaining alike! Perfectly perched above the creek, this home offers an outdoor wonderland! It showcases a long dock with 2 lifts perfect for boating or kayaking or canoeing, an inground pool, 2 decks and magical water views! A bird loverś paradise, Swantown Creek and the connecting Sassafras River sit on the upper Chesapeake Bay watershed, making it a thoroughfare for resident species and migratory birds traveling the Atlantic Flyway! You will see Bald Eagles all year long! Inside this completely renovated Masterpiece, the fine details will fascinate even the most discerning buyers, from the gorgeous hardwood flooring to the gourmet kitchen to the double sided fireplace! The very spacious open floor plan is ideal for entertaining with multiple living and dining areas that simultaneously offer those lovely views! The luxurious kitchen has been beautifully appointed with premium countertops, a suite of super high end Forno Stainless Steel appliances including a 48" Dual Fuel Double Oven, 48" wall mounted hood, 60" 2-piece, convertible, built-in fridge, super quiet dishwasher and 24" microwave drawer, stunning cabinetry & hardware, a radiant island and a splendid butler bar! A split bedroom floor plan allows for some seclusion for the primary suite! The primary suite is intoxicating! It has its own deck, an awesome walk through closet with a ready made closet system, a palatial luxurious tiled shower, dazzling double sinks and separate water closet! The other two bedrooms are nicely situated at the other end of the home with a Jack & Jill bath! There is also a flexible bonus room off the living room perfect for a home office/study. The laundry area is sweetly tucked away behind the kitchen and flanking the stacked washer/dryer is lovely cabinetry and a useful sink! No detail has been overlooked namely the interior plantation shutters, ceiling fans, led lighting and fixtures and so much more! The large driveway and cul-de-sac location translates to lots of parking and you will also appreciate the side yard storage shed. Come be awed by this Shorewood Estates Showpiece!

3 Beds ⋅ 3 Baths

Impressive Masterpiece on Swantown Creek with 2 Boat Lifts! Exquisitely Crafted, the high quality upgrades have created an oasis for serenity, relaxation and entertaining alike! Perfectly perched above the creek, this home offers an outdoor wonderland! It showcases a long dock with 2 lifts perfect for boating or kayaking or canoeing, an inground pool, 2 decks and magical water views! A bird loverś paradise, Swantown Creek and the connecting Sassafras River sit on the upper Chesapeake Bay watershed, making it a thoroughfare for resident species and migratory birds traveling the Atlantic Flyway! You will see Bald Eagles all year long! Inside this completely renovated Masterpiece, the fine details will fascinate even the most discerning buyers, from the gorgeous hardwood flooring to the gourmet kitchen to the double sided fireplace! The very spacious open floor plan is ideal for entertaining with multiple living and dining areas that simultaneously offer those lovely views! The luxurious kitchen has been beautifully appointed with premium countertops, a suite of super high end Forno Stainless Steel appliances including a 48" Dual Fuel Double Oven, 48" wall mounted hood, 60" 2-piece, convertible, built-in fridge, super quiet dishwasher and 24" microwave drawer, stunning cabinetry & hardware, a radiant island and a splendid butler bar! A split bedroom floor plan allows for some seclusion for the primary suite! The primary suite is intoxicating! It has its own deck, an awesome walk through closet with a ready made closet system, a palatial luxurious tiled shower, dazzling double sinks and separate water closet! The other two bedrooms are nicely situated at the other end of the home with a Jack & Jill bath! There is also a flexible bonus room off the living room perfect for a home office/study. The laundry area is sweetly tucked away behind the kitchen and flanking the stacked washer/dryer is lovely cabinetry and a useful sink! No detail has been overlooked namely the interior plantation shutters, ceiling fans, led lighting and fixtures and so much more! The large driveway and cul-de-sac location translates to lots of parking and you will also appreciate the side yard storage shed. Come be awed by this Shorewood Estates Showpiece!

13876 Swantown Creek Rd, Galena

Listing courtesy of Patterson-Schwartz - Greenville. Contact:

$1,250,000

Lot 1 is +/- 86 acres of prime development land in Kent County's Rt. 301 Growth Corridor. With +2,500 ft along Rt. 301 and 1,295 ft along Carroll Clark Rd, this property offers easy access to Middletown, DE and Rt. 1. The property is zoned Employment Center and qualifies for Kent County and Maryland State incentives. Approximately 46 acres are currently in ag use. There is a cell tower on the property with no annual income. The property is partially wooded with +/- 19 acres in Forest Conservation.

Lot 1 Carroll Clark, Galena

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$725,000

Set on a moderate bluff along the upper Sassafras River, this inviting waterfront property offers pristine, natural down river views and exceptional access to the water. Enjoy your private dock, boat lift, and plenty of space for kayaks, paddleboards, and other water toys. The home features three bedrooms plus a walkout basement ready for your vision—ideal for creating additional living space, a recreation area, or guest accommodations. With easy access to points north and located less than 10 minutes from Middletown, Delaware, this property is perfectly suited as a weekend getaway or a comfortable downsized waterfront retreat.

3 Beds ⋅ 2 Baths

Set on a moderate bluff along the upper Sassafras River, this inviting waterfront property offers pristine, natural down river views and exceptional access to the water. Enjoy your private dock, boat lift, and plenty of space for kayaks, paddleboards, and other water toys. The home features three bedrooms plus a walkout basement ready for your vision—ideal for creating additional living space, a recreation area, or guest accommodations. With easy access to points north and located less than 10 minutes from Middletown, Delaware, this property is perfectly suited as a weekend getaway or a comfortable downsized waterfront retreat.

32745 Hunt Ln, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

$625,000

It is a rare opportunity for a private waterfront lot off the Sassafras River to come available. This 14 acre parcel of land is located above the bridge in a well established small community of Gentle Winds. Scenic and tranquil area for birding watching, kayaking or taking a short boat ride to restaurants located down the river. With this 14 acre lot, there are open areas and woods to play with. Build the house of your dreams and be able to work and play where you live. Short drive to tax free shopping in Middletown DE. It appears that this property is allowed to have an in-law suite as a separate living area, note the letter from Gentle Winds HOA, Also the Kent county has their assessment. The Hoa, will need to review plans and etc. as before.

14200 Metasequoia Ct, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

$535,000

Home Sweet Home. How Sweet it is! Rustic Log cabin 4 Bedrooms, 2Baths. Front and rear porches, In ground Pool, 3 Car detached garage, 24X 34 detached metal building. Great for all the toys, Shop, or Storage. Mature Landscaping, All Situated on 9.28 Acres located close to the Sassafras River. Wow! Call for your private showing.

4 Beds ⋅ 2 Baths

Home Sweet Home. How Sweet it is! Rustic Log cabin 4 Bedrooms, 2Baths. Front and rear porches, In ground Pool, 3 Car detached garage, 24X 34 detached metal building. Great for all the toys, Shop, or Storage. Mature Landscaping, All Situated on 9.28 Acres located close to the Sassafras River. Wow! Call for your private showing.

13984 Mill Creek Ln, Galena

Listing courtesy of Key Realty, Incorporated. Contact:

$379,000

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!

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:

$369,900

Welcome to this beautifully updated country farmhouse, where classic charm meets modern comfort in a serene rural setting. Thoughtfully renovated throughout, this inviting home offers a spacious first-floor primary suite, two additional bedrooms, and generous walk-in attic space—perfect for storage. The main level has been freshly painted and features new flooring, creating a bright, move-in-ready atmosphere. Efficient mini-splits provide comfortable climate control throughout the home, with capacity for one more unit if desired. Step outside through the newer French doors into a fully fenced backyard, ideal for pets, gardening, or simply enjoying the peaceful surroundings. Recent updates include 6 mini-splits, a new hot water heater (installed 11/25), a front roof that is 5–7 years old, and a rear roof just 5 years old with durable 50-year shingles. The third level boasts newly conditioned bonus spaces, offering flexible living or recreational options. Location is a true highlight. Situated minutes from the Sassafras River, a nearby marina, and popular restaurants including the Kitty Knight Inn and Restaurant, Fish Whistle, and Twinny’s. This property places waterfront dining and recreation right at your doorstep. You’re only one mile south of the Fredericktown boat ramp, making boating and water access effortless. Route 301 is an easy 10-minute drive for convenient travel north or south, and the home sits along the Chesapeake Scenic Byway—your gateway to charming waterfront towns such as Chesapeake City, Chestertown, and more. This remodeled farmhouse blends updated living with timeless country appeal and an unbeatable Eastern Shore location. Don’t miss the opportunity to make it yours.

3 Beds ⋅ 3 Baths

Welcome to this beautifully updated country farmhouse, where classic charm meets modern comfort in a serene rural setting. Thoughtfully renovated throughout, this inviting home offers a spacious first-floor primary suite, two additional bedrooms, and generous walk-in attic space—perfect for storage. The main level has been freshly painted and features new flooring, creating a bright, move-in-ready atmosphere. Efficient mini-splits provide comfortable climate control throughout the home, with capacity for one more unit if desired. Step outside through the newer French doors into a fully fenced backyard, ideal for pets, gardening, or simply enjoying the peaceful surroundings. Recent updates include 6 mini-splits, a new hot water heater (installed 11/25), a front roof that is 5–7 years old, and a rear roof just 5 years old with durable 50-year shingles. The third level boasts newly conditioned bonus spaces, offering flexible living or recreational options. Location is a true highlight. Situated minutes from the Sassafras River, a nearby marina, and popular restaurants including the Kitty Knight Inn and Restaurant, Fish Whistle, and Twinny’s. This property places waterfront dining and recreation right at your doorstep. You’re only one mile south of the Fredericktown boat ramp, making boating and water access effortless. Route 301 is an easy 10-minute drive for convenient travel north or south, and the home sits along the Chesapeake Scenic Byway—your gateway to charming waterfront towns such as Chesapeake City, Chestertown, and more. This remodeled farmhouse blends updated living with timeless country appeal and an unbeatable Eastern Shore location. Don’t miss the opportunity to make it yours.

13831 Augustine Herman Hwy, Galena

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$363,000

Welcome to Galena a little big town. Located just down the road from the Sassafras River this area has excellent access to the Chesapeake Bay, shopping, restaurants and more. With just about an hours drive you can be in Baltimore, Philadelphia or Annapolis. What an opportunity to build instant equity. Spacious home in great community, backing to farmland. This home is located in the community, but not within town limits. Enjoy public utilities without the town tax! Home has been maintained over the years, featuring new HVAC less than a year ago as well as roof replacment 10 years ago. Nicely laid out with living room, dining room, eat in kitchen, laundry room, powder room and great family room on the main level. The second level has a primary suite with loft, two additional bedrooms and hall bath. There is also a nicely proportioned two car attached garage. Home will benefit from updating to make it your own.

3 Beds ⋅ 3 Baths

Welcome to Galena a little big town. Located just down the road from the Sassafras River this area has excellent access to the Chesapeake Bay, shopping, restaurants and more. With just about an hours drive you can be in Baltimore, Philadelphia or Annapolis. What an opportunity to build instant equity. Spacious home in great community, backing to farmland. This home is located in the community, but not within town limits. Enjoy public utilities without the town tax! Home has been maintained over the years, featuring new HVAC less than a year ago as well as roof replacment 10 years ago. Nicely laid out with living room, dining room, eat in kitchen, laundry room, powder room and great family room on the main level. The second level has a primary suite with loft, two additional bedrooms and hall bath. There is also a nicely proportioned two car attached garage. Home will benefit from updating to make it your own.

206 Maplewood Ln, Galena

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

$325,000

SELLER WELCOMES ALLREASONABLE OFFERS! Discover easy one-level living at this three-bedroom, two-bath ranch home located in Galena’s Sassafras subdivision. Set on a cleared 0.47-acre lot, the property offers spacious front, side, and rear yards with room for outdoor entertaining, recreation, gardening, or future improvements. Inside, the open layout creates a natural flow between the light-filled living area, country-style kitchen, and adjoining breakfast space. The kitchen is equipped with ample cabinetry, an electric range, built-in microwave, and dishwasher, while luxury vinyl plank flooring adds durability and a cohesive look throughout the main living areas. The primary bedroom includes a private bath with a soaking tub and separate stall shower. Two additional bedrooms provide flexibility for sleeping space, an office, hobbies, or storage. A detached shed provides additional space for lawn equipment and outdoor items. Built in 2007 and surrounded by peaceful garden and lawn views, this home offers comfortable living with convenient access to Galena and the surrounding Eastern Shore area. Schedule your private showing and submit your offer for the seller’s consideration.

3 Beds ⋅ 2 Baths

SELLER WELCOMES ALLREASONABLE OFFERS! Discover easy one-level living at this three-bedroom, two-bath ranch home located in Galena’s Sassafras subdivision. Set on a cleared 0.47-acre lot, the property offers spacious front, side, and rear yards with room for outdoor entertaining, recreation, gardening, or future improvements. Inside, the open layout creates a natural flow between the light-filled living area, country-style kitchen, and adjoining breakfast space. The kitchen is equipped with ample cabinetry, an electric range, built-in microwave, and dishwasher, while luxury vinyl plank flooring adds durability and a cohesive look throughout the main living areas. The primary bedroom includes a private bath with a soaking tub and separate stall shower. Two additional bedrooms provide flexibility for sleeping space, an office, hobbies, or storage. A detached shed provides additional space for lawn equipment and outdoor items. Built in 2007 and surrounded by peaceful garden and lawn views, this home offers comfortable living with convenient access to Galena and the surrounding Eastern Shore area. Schedule your private showing and submit your offer for the seller’s consideration.

33741 Galena Sassafras Rd, Galena

Listing courtesy of EXP Realty, LLC. Contact: