Refine Search
Map
Sort by
$468,000
3 Beds ⋅ 2 Baths
Charming Brick Rancher Near the Chester River This custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, and a convenient circular driveway. The drive runs under a gable-roofed breezeway that connects to an oversized 26x40 two-car garage, which will soon have brand-new garage doors. Coming into the Home... Living Room: Walk along the cobblestone slate path and pass through the new, classic front door into a spacious living room featuring hardwood floors that run throughout the entire house. Dining & Kitchen: A curved archway leads from the living room directly into the dining room. The dining room has an entryway to the kitchen, which could easily be opened up for an even more open feel. Porch: The dining room leads right out to a comfortable porch—the perfect spot to relax and enjoy this nice, quiet neighborhood. Mudroom & Back Entry: An oversized back entry from the breezeway leads into a large mudroom and utility space. Featuring multiple closets and laundry hookups, this functional area offers plenty of space to be creative and fit your family's needs. Bedrooms: The main floor includes three bedrooms with hardwood floors and two full bathrooms Basement: The full basement features an open space with brand-new windows that allow plenty of natural light inside. It is equipped with a new sump pump, offering a perfect blank canvas for storage, a gym, or a rec room. Utilities, Key Updates & Location The house sits on a generous lot with mature landscaping and is connected to well water and public septic. Recent mechanical and structural updates include: Brand-new roof, oil furnace paired with a new HVAC system for efficient heating and cooling. Fresh paint inside and out. You can enjoy beautiful views of the Chester River coming and going from your new home, as well as scenic river views while taking your neighborhood walks. Enjoy the convenience of being just minutes from downtown shopping and dining. Bring your design ideas to update the interior and make it your own!

25750 Collins Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$2,150,000
4 Beds ⋅ 4 Baths
AMAZING PRICE REDUCTION! Open house on this very special home on July 11th. Sassafras Riverfront Retreat | Log cabin custom built home with Deep Water Pier, (seller 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 log cabin residence 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: 8888607369
$1,450,000
4 Beds ⋅ 5 Baths
Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip.  3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak.  The deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 5 full bathrooms, plus a large loft that could be used as an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home.  A new roof was installed in June, 2026. In both sitting rooms, you’ll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated.  Upstairs you’ll find two waterfront bedrooms, one with an updated attached bath. There's a second full bathroom and ample closet space in the hallway.  Downstairs, there are two additional full bathrooms and a large bedroom. Above the kitchen sits the light-filled loft, a great office, studio, or extra bedroom.  The exterior has a generous front porch, outdoor shower, circular drive, 2-car garage, fenced dog run, and additional garage space connected to the basement.  This light-filled waterfront property is located 15 minutes away from the waterfront community of Rock Hall and historic Chestertown.

22470 Fairgale Farm Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$3,150,000
7 Beds ⋅ 7 Baths
All showings require pre screening and financial capability prior to scheduling any showing. Rarely does a property of this sort come available in Kent County Maryland! This incredible 139+/- acre Chesapeake Bay property is available in it's entirety, however the seller may consider selling the primary residence with a reduced amount of acreage under the right conditions, providing the purchaser bares the cost to do so and is willing to wait the extended period of time to accomplish. The entire property features 72+/- tillable acres, 3900+/- footage of Chesapeake Bay beach frontage, extensive County road frontage, a 3.5 acre waterfowl pond, 2 other smaller ponds, a ten stall horse barn, and caretakers home. A large 33+/- acre flooded area, teeming with waterfowl and deer surrounded by woods runs through the heart of the property. The main residence, designed by architect Paul Rudolf, is perched upon the rip rapped shores of the Chesapeake Bay with endless broad water views. Although the main residence is in need of complete restoration, the site is extraordinary and the salvage reward is potentially significant in dollar value. There is a possibility for construction of a new home on the existing building pad. The hunting and recreational value for this property is enormous! Just imagine family picnics on the sandy beach or spending countless hours searching for sea glass and Indian artifacts while soaking up the sun and listening to the gentle waves roll up on the beach. This property is extremely private, however, convenient to Historic Chestertown, summer fun in Rock Hall, and a short drive to regional airports in Philadelphia, Baltimore and Washington DC. The property is being sold AS-IS, Where-IS and requires 24 hour notice to show with listing agent on site for any and all showings.

6520 Swan Creek Rd, Rock Hall

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$3,150,000
7 Beds ⋅ 7 Baths
All showings require pre screening and financial capability prior to scheduling any showing. Rarely does a property of this sort come available in Kent County Maryland! This incredible 139+/- acre Chesapeake Bay property is available in it's entirety, however the seller may consider selling the primary residence with a reduced amount of acreage under the right conditions, providing the purchaser bares the cost to do so and is willing to wait the extended period of time to accomplish. The entire property features 72+/- tillable acres, 3900+/- footage of Chesapeake Bay beach frontage, extensive County road frontage, a 3.5 acre waterfowl pond, 2 other smaller ponds, a ten stall horse barn, and caretakers home. A large 33+/- acre flooded area, teeming with waterfowl and deer surrounded by woods runs through the heart of the property. The main residence, designed by architect Paul Rudolf, is perched upon the rip rapped shores of the Chesapeake Bay with endless broad water views. Although the main residence is in need of complete restoration, the site is extraordinary and the salvage reward is potentially significant in dollar value. There is a possibility for construction of a new home on the existing building pad. The hunting and recreational value for this property is enormous! Just imagine family picnics on the sandy beach or spending countless hours searching for sea glass and Indian artifacts while soaking up the sun and listening to the gentle waves roll up on the beach. This property is extremely private, however, convenient to Historic Chestertown, summer fun in Rock Hall, and a short drive to regional airports in Philadelphia, Baltimore and Washington DC. The property is being sold AS-IS, Where-IS and requires 24 hour notice to show with listing agent on site for any and all showings.

6520 Swan Creek Rd, Rock Hall

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956