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$2,195,000
4 Beds ⋅ 3 Baths
Incredible WATERFRONT property offering expansive unobstructed views up and down the broad Chesapeake Bay. This exceptional property includes a manageable single-level home, a large climate-controlled shop/recreational detached building, a large waterfowl pond, a gently sloping lawn down to the substantially riprapped shoreline, several acres of farmland ideally suited for livestock, horses, gardening, micro-farming, or exceptional waterfowl hunting, and some of the most sensational sunsets in the world! Gliding Gander is truly a landmark property situated in a private setting between Historic Chestertown and Festive Rock Hall. The recently refreshed home features 3000-/+ Sq. Ft. of fully finished living space with endless broad ever ever-changing views of the Chesapeake Bay. Rooms include a spacious waterside sunroom, living with wood-burning fireplace, dining area, spacious kitchen with granite counters, den/library with built-in shelves, and a large converted garage that is used as an in-law suite. A full clean dry basement houses the home's mechanicals. Marinas are located nearby! Experience the "True Eastern Shore" all from one manageable property!

7280 Swan Creek Rd, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$2,195,000
4 Beds ⋅ 4 Baths
Incredible WATERFRONT property offering expansive unobstructed views up and down the broad Chesapeake Bay. This exceptional property includes a manageable single level home, a large climate controlled shop/recreational detached building, a large waterfowl pond, gently sloping lawn down to the substantially riprapped shoreline, several acres of farmland ideally suited for livestock, horses, gardening, micro farming, or exceptional waterfowl hunting, and some of the most sensational sunsets in the world! Gliding Gander is truly a landmark property situated in a private setting between Historic Chestertown and Festive Rock Hall. The recently refreshed home features 3000-/+ Sq. Ft. of fully finished living space with endless broad ever changing views of the Chesapeake Bay. Rooms include a spacious waterside sunroom, living room with wood burning fireplace, dining area, spacious kitchen with granite counters, den/library with built in shelves, and a large converted garage that is used as an in-law suite . A full clean dry basement houses the home's mechanicals. Marinas are located nearby! Experience the "True Eastern Shore" all from one manageable property!

7280 Swan Creek Rd, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$799,000
3 Beds ⋅ 3 Baths
This peaceful farmette has a bit of everything with a retired tree farm, 10acres of leased tillable land, 12 pristinely maintained garages, and a spacious 3 bedroom home with first floor owner's suite. Attention to detail and meticulous upkeep can be evidenced throughout this property. The extra garage space in the outbuildings are perfect for your home business or car collection. The generous owner's suite and additional two full sized bedrooms are all on the main level. The enclosed sunroom allows for an unmatched connection with nature year round with its gas stove and oversized glass windows. The open floor plan allows for easy flow between the Great Room and Gourmet Kitchen, both with countryside views. Upstairs has the perfect space for an office or hobby room. The full sized, partially finished basement has heating, and was previously used as an additional pantry and space for passion projects. Professional photos and more details to come soon.

32483 Galena Sassafras Rd, Galena

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

$2,200,000
3 Beds ⋅ 5 Baths
Custom built house on the East Fork of Langford Creek set on 8+ acres with a private dock. This is the first time the house has been for sale; original owners. It was built by Patrick Jones and designed by architects Dunning & Dunning from Swathmore, PA. Beautiful sunsets. It captures the lay out of the property and celebrates the water from every window. There is deep water (4.5 MLW, buyer to verify). 7-ton boat lift. Sunken living room with vaulted ceiling. White Oak floors through much of the house. Designed for outdoor living. There is a deck, screened in porch, covered front porch. 2 car garage off the kitchen. Storage area above the garage with separate outside access. Huge basement, partially finished. Plenty of room for guests, a workshop, and a garage door for all the toys. Shown by appointment only. No drive by's please. High speed internet.

23829 E Fork Dr, Chestertown

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

$1,700,000
5 Beds ⋅ 2 Baths
The owner is in the process of dividing the two properties and will soon be listing the primary residence separately. This parcel is zoned AZD and has a special exception to operate a cottage industry. The Cording property is quite unique. The total parcel size is 3.84 acres. The primary residence built in 1985 is a cape cod style with a water-proofed basement having a finished room and a two-car attached garage having an epoxy floor and insulated overhead doors. The grounds are magnificent with extensive and well-maintained landscaping and lighting. The rear 14 X 30 deck accesses the in-ground pool area that is surrounded by a spacious, paved pool area offering a hot tub. There is a large paved area with benches that opens to a separate firepit sitting area as well as a beverage serving area. New exterior upgrades include 40-year roof shingles, gutter guards, soffit, facia, and Trex decking. The home was built with 2 X 6 walls offering great energy savings and was built with poplar wood locally milled. The house exterior is cedar siding with Andersen windows. The home is approximately 2200 +/-SF with two bedrooms on the first floor as well as three bedrooms on the second floor. The kitchen offers a granite countertop and cherry cabinetry. The interior staircase that opens to the living room with a wood-burning fireplace was newly installed approximately four years ago. There are two well-built buildings on the grounds: one is used for storage and the other is insulated and finished with drywall having a cathedral ceiling and wired for heat/air if one should wish to have heat/air installed. The second part of this listing offers a two-story dwelling built in 2007 with a full basement, garage, a 40 X 60 fourteen-foot-high ceiling accessory building with an overhead door and bath, and also a 15 X 30 boat house with a twelve-foot-high ceiling. The total square footage on each floor, as well as the basement of the two-story dwelling, is 2400 SF…a total of 7200 SF. The first-floor open work area with 10’ ceilings and loading dock presently serves as Cording Concepts business. The second floor offers a very large kitchen with granite countertops and a tiled floor, four additional rooms that are presently used for offices as well as there being a reception area…these rooms of course could be used as bedrooms. The basement and garage are poured concrete insulated walls that keep the basement and garage the same temperature year-round. The garage has a car wash drain. The exterior features of this two-story dwelling are a welcoming front porch, cement hardboard siding, built with 2 X 6 walls, two heat pumps, and retaining walls at the rear basement/garage access.

25024 Cording Rd, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$739,900
6 Beds ⋅ 4 Baths
Welcome to the former historic HILLTOP HOTEL! A charming estate which underwent significant renovations in 2021 while preserving many of the original characteristics the home has to offer. This property is unlike any other - offering historic charm, tranquil atmosphere, ample privacy, outdoor living & entertaining as well as turnkey amenities. The property sits perched high above the hillside of the Eastern Shore providing for stunning sunsets as you relax on the wraparound porch feeling the gentle breeze from the Chesapeake Bay. As you enter and proceed up the gravel driveway you are greeted by a large circular drive, beautifully manicured lawn, 4.74 acres of mature landscaping and the grandeur of the 3 story historic home. The first and second floors have been updated to include bright new paint throughout, remodeled kitchen offering an abundance of natural light, all new appliances, french doors were installed off the kitchen and study leading out to a new beautiful brick terrace overlooking scenic countryside views, updated powered room on the first floor, primary second floor bath has been completely remodeled to include updated amenities. The second floor offers 3 bedrooms, 2 full baths along with a spacious laundry room. As you make your way up to the third floor you immediately noticed the extensive renovations. Every aspect of the third floor was meticulously remodeled and redesigned including new insulation, new plumbing, new electric, new drywall, new commercial grade HVAC system and all 14 windows throughout the third floor were replaced. The third floor offers 3 bedrooms, 1 full bath and large beautiful living area. All hardwood floors throughout the home were refinished to their original beauty. New commercial grade water treatment system was installed. The wraparound porch was completely painted and all porch columns were wrapped. The exterior back of the home was sealed and painted. New roof installed. Both chimneys were repointed. Dual zone HVAC. This is a COMMERCIALLY ZONED property - Zoned Crossroads Commercial. Perfect for B&B or commercial use. Centrally located between historic Chestertown, MD and Rock Hall, MD. Owners are open to selling property furnished with the exception of several items.

7979 Sandy Bottom Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$775,000
3 Beds ⋅ 2 Baths
Welcome to 12168 Still Pond Creek Road. This 18.01 acre property has a 1710 sf Cape Cod style 3 bedroom, 2 bathroom home sitting right off its very large and roomy front yard where you will find beautiful yellow pine flooring, a fire place and a wood stove. The basement is partially finished with a pantry and a workshop. Home also has a two car attached garage with an unfinished room above for more storage or maybe an additional room. This lot is 1/2 open land, 1/2 wooded. Conveniently located 1/2 mile to Still Pond Creek, yet you are out of the critical area!!! The wooded acreage to this property is perfect for deer and turkey hunting. So much potential on this property it is a must see today!

12168 Still Pond Creek Rd, Worton

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

$572,000
3 Beds ⋅ 3 Baths
A wonderful 3 bedroom 2.5 bath brick rancher in the country but close to Chestertown and Middletown for tax free shopping. It sits on about 2.4 acres of a rolling lot that goes down to the community pond and picnic area. It has an instant hot water system, a relatively new septic system, roof and other amenities. It is close to the schools and currently has school bus service on the street. The street ends at a cul de sac. This is the place for you . There is the potential for a qualified buyer to assume a very low interest VA loan.

24386 Waterview Dr, Worton

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

$665,000
5 Beds ⋅ 3 Baths
5.5 Acre Estate in ROCK HALL! A rare opportunity to own a piece of history. Coupled with modern conveniences, this partially renovated home built 1920 is a perfect blend of then and now. Over 4,000 sq ft of history, elegance, and charm. Just mention the address and the local community knows which home it is. The love and care that went into keeping this home so pristine and true to its history is evident. Bonus rooms, built-ins, hardwood floors, balconies, patio, enclosed front porch, it is all here. Views, privacy, nature…yes, that too. But what stands out about this house is the architecture! From walking up the Imperial Staircase to the second floor to the Meridional Inlay on the first floor, this home is a treasure. Upon entering the home from the driveway, the left side of the first floor offers a gourmet kitchen with breakfast bar and dining area, a formal dining room and large living room with an oversized sit in bay window and wood burning fireplace with gas insert. The right side of the first floor has a full-service laundry room, half bath, den or office and bonus room with a functioning pellet stove. New 50-year Architectural roofing on the home and all out-buildings. The front screened in front porch and the bay window was done with country red metal roofing. The look is stunning. Moving upstairs, to the left a double bedroom or bedroom with attached bonus room. To the right a full bathroom, with two additional rooms before you enter the primary bedroom with walk out balcony with fantastic naturistic views of the back acreage of the property and patio below, dressing area, full bathroom and of course his and hers walk in closets. Culvert pipe was installed when new stone was placed in the driveway to improve drainage. The driveway circles around a Gazebo that has a new Country Red Cupola. A detached two car garage and workshop as well as separate shed for yard tools and kennel all with new matching 50-year Architectural roofing. A little creek runs through and alongside the property. New Renaih Tankless Gas Water Heater installed 5/23/23 Located in the infamous seaside town of Rock Hall MD. Just minutes away from downtown, the harbor and marinas and restaurants.

6006 Rock Hall Rd, Rock Hall

Listing courtesy of Coldwell Banker Premier - Rehoboth. Contact: (302) 227-5000
$3,750,000
6 Beds ⋅ 9 Baths
Breathtaking 18 ± acre Sassafras River Estate conveniently positioned between Philadelphia and Baltimore on the Eastern Shore of Maryland. Less than one hour from Philadelphia International Airport. 17 bedrooms 16.5 baths, circa late 1800's restored Italianate Manor House with unbelievable down river views and summer sunsets. Partially finished basement with an extensive wine cellar designed for the wine connoisseur, with a capacity for approximately 2500 bottles. Pick your favorite relaxing spot on the dock, the Manor House, the Cottage, Pool House, Guest House, Barn Tavern, or anywhere over the expansive private grounds. Perfect location for plenty of water sports, water skiing, wakeboarding, sailing, paddle boarding and fishing. Just minutes by boat to deep water Georgetown Harbor, with its numerous shops and restaurants. Must experience this property and area to fully appreciate. Perfect for the most discerning of Eastern Shore waterfront Buyers. Property has 24 hour security/fire/police cameras. Listing agent must accompany all showings, with 48 hours notice. Prior to confirmation of showing, selling agent will provide listing agent with copy of pre-qualification satisfactory to seller, and selling agent must accompany buyer at all showings. Property is being sold in “AS IS” condition. Any inspections are for informational purposes only.

32180 Wilson Point Rd, Galena

Listing courtesy of Patterson-Schwartz Real Estate. Contact: (410) 885-1606
$1,299,000
6 Beds ⋅ 7 Baths
Gibraltar is a stunning 6 bedroom masterpiece built circa 1995 at a cost of two million dollars. The very open floorplan has ceiling heights from 9 feet to 22 feet. Primary bedroom suites on both upper and main floors, both with jacuzzi tub, separate shower, double sinks, and heated bathroom floors. Elevator and level stone walk to front door allow ease of access, floating marble staircase in 43 foot wide heated marble entry way. The three floor to ceiling stone fireplaces have gas inserts and stone mantles. Large bedrooms with walk in closets in every room. Hardwood floors in Dining Room, Living room, and Office. Custom designed kitchen with Sub-Zero refrig, Dacor cooktop with grill, GE Monogram oven and microwave, Miele Dishwasher, U-line Beverage refrig, trash compactor, Wet Bar in Entertainment room with sink and service window to outside terrace. The pantry/laundry room with floor to ceiling cabinets, utility sink. Security system, water treatment system. Grounds are beautifully landscaped with a variety of flowers, bushes, trees and lovely stone walkways. The outdoor terrace has a built in hot tub and grill. The circular driveway presents an elegant way to enter the home. The driveway will hold at least 15 cars. The home has 3 Geothermal HVAC systems with 7 thermostats. Three car side entry garage. Gibraltar is being sold in "AS IS" condition. Any inspections are for informational purposes only.

14079 Crataegus Ct, Galena

Listing courtesy of Patterson-Schwartz Real Estate. Contact: (410) 885-1606
$448,000
3 Beds ⋅ 3 Baths
Rare combination of historic home and water views, with many of the benefits of waterfront without the high cost. Two decks with relaxing water views and very large yard for plenty of out door activities. Rent a slip at the marina below and enjoy all the benefits of the marina including pool, boat store, ice cream shop and local restaurants. Plenty of rooms to fit your desires or imagination.

14002 Augustine Herman Hwy, Georgetown

Listing courtesy of Gunther-McClary Real Estate. Contact: