Chestertown MD Real Estate & Homes for Sale

Move right in to this water access/water view rancher in Great Oak on Fairlee Creek as it opens to the bay. HOA gives you use of the pool, beach, golf course. Farm views from the screened in porch and patio. Split bedroom floor plan. Rooms are light and bright. New roof. Private road with annual maintenance fee of $330 per year. Aproximately 9 miles from Chestertown. Many more pictures coming soon!

This is what you've been looking for! Gorgeous, updated home in the desirable Fannell's Meadow community on a large 2.8 acre lot at the end of a cul-de-sac, backing to trees. With a new roof, windows, HVAC and flooring, this house is move-in ready! It offers a large kitchen with island, wood cabinets, upgraded counters and luxury vinyl plank flooring, breakfast area, a formal dining room and study, as well as a huge family room with vaulted, beamed ceilings and a beautiful fireplace. The Master suite features a walk-in closet and beautiful Master bath with herringbone tiled shower and a dual vanity. A huge, unfinished basement and two car garage round out the complete package. Your dream home awaits! Interior pictures coming later this week.

Deluxe Haven Framed By Woodland - Airy and open plan colonial-style home with rural-area serenity. This large, pristine-clean two-story targets today's multi-taskers beautifully. 4 bedrooms. The formal dining room and large inviting living room welcome guests to your home for social gatherings. You will delight in the convenience and good looks of the gourmet kitchen with butcher-block countertop, stainless steel appliances, center island. The spacious Primary Bedroom offers a large sitting area which could easily be used as a nursery or conveniently could be a home-office or study. Or maybe, with some effort, turn it into a 5th bedroom, potentially add a bathroom, walk-in closet? The garage guarantees a ready-to-roll automobile as well as comfortable storage and/or workspace. It has heat and air, but heat pump but requires repair to be operable. The garage also contains an attic space for additional storage. Only about an hour to Annapolis, and an easy commute to Baltimore or Delaware. Historic Chestertown and Washington College are just a few minutes away. Close proximity to the water on Mill and Worton Creek and recreational outdoor fun like boating, fishing, and hunting. There is a community association, which is voluntary and costs $40 per year and includes 2 wharves and access to boat slips, shower facilities, and a launching ramp. Membership provides water access. Start this year off right with this lovely Home. Under 275K! Wow, with the current interest rates, what an incredible deal.

Charming 1900's original farm house located on Cacaway farm cooperative. This home has broad expansive views of beautiful Langford Creek. The home offers 3 bedrooms and 3 full baths and spectacular deck and two enclosed heated porches overlooking Langford Bay. This home offers many amenities not found in older homes, including a Master Bath. Great deep water slip with lift located on the community dock with very easy access. Sailing, Crabbing, Fishing, Water fowl hunting or just watching sunsets all at you back door. This property offers all of the desired attributes of Eastern Shore living including the option to purchase 20% ownership of the surrounding 177 acre Cacaway farm and Cacaway Island, owned exclusively by the cooperative members.

Quiet and peaceful living. Your chance to get a new home for a great price! Being built is a 4 bedroom 2 bath, open floorplan rancher. Everything you need! Why settle for any house when you can create your memories here, brand new. This home is conveniently located to all the major routes, only minutes away from Downtown Chestertown and Centreville. A short easy commute to Middletown, Dover, Annapolis, DC, and the beautiful beaches. Located in QA County School District. Lot is being cleared and getting ready for construction. Attached is the list of specifications for construction, with time to be able to customize the colors of your new home and have your very pick of countertops, cabinets, flooring, and more!!

Don't miss your chance to own in Great Oak Landing. Make this summer a new beginning by the Bay. Play a round on the 9-hole executive golf course or enjoy the summer heat at the pool. Ask friends to join you for a drink at The Landing Restaurant or Jellyfish Joel's Beach Bar before heading to the sandy beach for a sunset bonfire. This is the the Eastern Shore Bay life at its best, just 20 minutes from historic Chestertown and 1.5 hours from Philadelphia. Access to amenities is optional HOA. Spacious colonial with wrap around porch and all the southern charm you need. Large living room with brick fireplace and eat in kitchen with Corian Counters. Off the kitchen there's a sunroom and a separate screened porch for afternoons in. First floor also features a formal dining room, laundry room and full bath. Upstairs you'll find 2 bedrooms, a large hall bath and the master suite with private bathroom and walk in closet. The property also has a 2 car garage with extra 3rd bay perfect for storage or a hobby room.

CUTE & WELL MAINTAINED! This sweet bungalow/ cape cod has all the living space you need on one level with two bedrooms and a full bath! The second level is a bonus with a open concept room with full bath & a cedar walk in closet! This home has maintained its old world charm with the original built in cornices, wood floors and brick fire place. This home was built perfectly for todays situation with a separate exterior entrance into a sunny office/classroom. Instant hot water on demand right at the kitchen sink so you can enjoy a cup of tea in the huge kitchen with plenty of storage! There is a large sunny laundry/mud room off the deck/driveway into the kitchen for an easy transfer for groceries from the car! Enjoy the large deep private backyard with two decks a separate garage and a new gravel driveway lined with wood beams, located on a wide one way street a few houses away from Washington College!

A blank canvas with strong bones... The home was taken down to the studs, beams stabilized, windows restored, Spanish Cedar front door, restored staircase restored... ENTER AT YOUR OWN RISK, INDEMNIFICATION AGREEMENT MUST BE SIGNED PRIOR TO ENTRY.

Take a look at this beautiful townhome located in Tolchester Village! One of 23 available duplexes and townhouses that have been completely remodeled!! Featuring a terrific galley kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. The three bedroom units are priced at $129,900 and the two bedroom units are priced at $119,900. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40.00 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Updated home.. fenced back yard with a storage shed, zoned heat pumps. There is a patio and a third floor deck overlooking the semi private back yard. Brand new carpet throughout. Tiled floors in kitchen and Florida room, and fresh paint, inside and out. This home is adorable, just a couple of blocks from the wonderful historic Chestertown Shopping Area, and Washington College. One of the rooms upstairs has "cut outs" overlooking the stairway and owner will close those off to make another bedroom if desired. Shows well, no fridge or stove at present.

Take a look at this beautiful townhome located in Tolchester Village! One of 23 available duplexes and townhouses that have been completely remodeled!! Featuring a terrific galley kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. The three bedroom units are priced at $129,900 and the two bedroom units are priced at $119,900. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40.00 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Presenting "Honest Point Farm" - Embrace the finest of Eastern Shore Living, Serenity and Nature at Honest Point Farm. Three Waterfront homes in Chestertown's Estate area all situated on 26 acres. This rare property consists of a beautifully maintained and updated main estate residence with breathtaking views and two charming guest homes- Winter Cottage and Summer Cottage. The main residence boasts 5 bedrooms (4 en-suite) a recently added expansive gourmet kitchen, renovated bathrooms, refinished hardwood floors, generator, 3 new heat pumps and a recently refinished waterside gunite pool. The guest homes each boast 2 bedrooms and one bath, perfect for company or as rentals. Ideally located, each dwelling has its own privacy and gorgeous views. Grounds also include an orchard, garden, wooded area, dock, in ground pool, barn, pond, various outbuildings with approximately 20 acres of woods. Given the acreage and all the fabulous amenities, this property is an exceptional offering! **Property Video in Virtual Tours**

TURN-KEY HOME AND SHE WON'T LAST LONG! The main level features a tastefully updated/upgraded kitchen with breakfast nook, hardwood flooring, built-ins, separately zoned spacious master suite with reading/sitting room, walk-in closet with custom built-ins and laundry + large master bathroom... the upper level boasts 4 bedrooms and 2 full bathrooms. The basement offers generous storage capacity and game area, all of which is protected by a french drain system...

A real restoration opportunity on Water St. This Victorian is a project for someone who has a love of old houses.It needs attention. This house has a Mansard roof is covered in pressed tin. Hardwood floors throughout and high ceilings. Crown moldings, chair- railings built-ins and fireplaces. There is a total of 5 bedrooms and 3.5 baths. Wide covered porch in the front. Screened porch in the rear. 2 car garage and driveway for off street parking. Heat is not functioning, needs a new roof(part is covered with a tarp). Partial central air. Some views of the river over the 18th century houses from the second and third floors. This house has great potential and is a rare find for Water St. It is waiting to be restored to its former glory. Property is being sold in as-is condition; some restoration plans available.

Solid investment property. Property is currently leased for a year through 5/15/2021. Rental market is strong because of close proximity to College and downtown. Fenced in rear yard allows privacy and shed has ample storage for yard accessories. If your are looking to add to your investment portfolio, take a look as this has positive cash flow. 24 hours showing notice required because house is tenant occupied. Lister must accompany. There is no sign on property.

Welcome to the historic John . Stam house, the only "A-rated" Victorian in Chestertown according to the Secretary of the Interior. This property has so much to offer. A Gothic Revival Victorian with painted fire places, a double parlor with pocket doors, and entrance hall. Features such as hand painted plastered ceilings, Jenny doors, and original medallions, make this a one of a kind home. Dado chair rail and paneling, Bradbury and Bradbury Art Wallpapers, Soapstone fireplaces, China closet, and the list goes on. The details are such that the property really needs to be seen to be appreciated. Kitchen is completely upgraded with Delohghi stove and sub zero refrigerator. Waterfall in the back yard with gracious gardens make for a charming outdoor oasis. "Carriage slate "architectural shingle roof. Currently run as a bed and breakfast. Additional buildable lot at the rear of the property included in the sale which makes the total property approximately 1.3 acres. . Driveway with 6-8 parking spaces makes hosting guests easy.

Beautiful, well maintained 3 bedroom end unit townhome. Just minutes from downtown Chestertown. Features freshly refinished hardwood floors, new carpet, new roof, vaulted master bedroom, soaking tub and separate shower in the master bath, 9 foot ceilings on the first floor, walk out second story deck, and an over-sized garage with a workshop. The home is very close to shopping and restaurants. A perfect place for weekends or year-round lifestyle living.

This downtown Chestertown house with good bones is priced right for a state of the art rehab .. Single residence ideal but a two unit property is possible.

Views of the Chester River from this Byford Court property. One floor living. 2 wood burning fireplaces, hardwood floors. Much attention to detail. French doors, spectacular kitchen, skylights in all the best places, wonderful landscaping includes a mature fig tree. Just a short walk to the heart of Chestertown. Private back and rear yards. Long rear all weather porch.

"Walnut Point Farm" ~ Exquisite 300+ Acre Waterfront Farm with over a mile of Shoreline is the perfect Eastern Shore Retreat! The Estate offers a 7,500+/- Main House with indoor and outdoor pools, Pier with Grand Boathouse and lift with 7ft+/- MLW, Large 3 bedroom Historic Guest House, Waterfront Caretakers Home, Large Barn for all farming equipment, Covered Bridge with many other outbuildings and blinds plus a few waterfowl ponds. This Estate is perfect for those looking for and escape from the hustle and bustle of the metropolitan lifestyle that would like to take in all that nature offers with a plethora of high end amenities. Please See Truplace Interactive Tour For more Photos and Floorplan at https://mls.TruPlace.com/property/406/84311/

"Walnut Point Farm" ~ Exquisite 300+ Acre Waterfront Farm with over a mile of Shoreline is the perfect Eastern Shore Retreat! The Estate offers a 7,500+/- Main House with indoor and outdoor pools, Pier with Grand Boathouse and lift with 7ft+/- MLW, Large 3 bedroom Historic Guest House, Waterfront Caretakers Home, Large Barn for all farming equipment, Covered Bridge with many other outbuildings and blinds plus a few waterfowl ponds. This Estate is perfect for those looking for and escape from the hustle and bustle of the metropolitan lifestyle that would like to take in all that nature offers with a plethora of high end amenities. Please See Truplace Interactive Tour For more Photos and Floorplan at https://mls.TruPlace.com/property/406/84311/

This Beautiful Brick home is located in Coventry Farms. Its backs up to woods, partially cleared, where you will enjoy lots of wildlife, including wild turkeys feeding. Very private setting with a patio that has a walk-out entrance from the awesome basement. The rear also bodes a balcony from the kitchen. This house is only 17 years old, but recently had all new windows installed plus $10,000.00 of interior upgrades. The home has a generator and solar panels for energy efficiency. Main floor has a formal dining room and formal living room, as well as a very workable kitchen. The Master bedroom is on one side of the house, while the other 2 bedrooms are on the opposite side. The basement has a game room with a propane fireplace, wet bar, 1/2 bath, bonus room, living room, and workshop. There is a chair lift from the main floor to the basement if needed, or it can be removed. Mature landscaping with a circular asphalt driveway that connects to the 2 car garage with an entrance to the main floor.

Great investment opportunity. Currently rented to college students for $2280 per month. Spacious brick rancher in College Heights. Remodeled kitchen and gleaming hardwood floors. Finished lower level adds an additional bedroom and bath as well as a large family room. Ample room in the back yard. Subject to existing lease which ends 7/1/2021. High speed internet available on site.

Nice investment property, tenant occupied. Tenant would like to stay.

PENTRIDGE WOODS FARMThis lovely property in the County of Kent is located in an unspoiled corner of the Maryland's Eastern Shore. It boasts productive fields, a dense forest and two architecturally significant residences in the contemporary style. It has been priced to encourage the addition of your design for a barn and/or stable. Equestrian enthusiasts have gravitated to Kent County because of its central Eastern US location, swift distance to three major airports, open fields and conserved land assuring this rural setting in perpetuity. One would never dream that it is surrounded by twelve million people in four major metropolitan areas. PENTRIDGE WOODS FARM located in the agricultural heartland of Kent County, is forever protected from subdivision and commercial development with conservation easements. An established avian refuge and the woods protect the Chesapeake Bay watershed while providing habitat to native species. The next owner can be part of ecologically sound farming innovations. PENTRIDGE WOODS FARM is just minutes from Historic Chestertown and is where one will find many and varied sports events and cultural activities. The 10th oldest college in America, Washington College, located in Chestertown. Sailing, canoes and kayaks on beautiful, "preserved" Chester River is a common sight. Many farms are preserved, endorse organic farming all, of which, creates a countywide agricultural setting. Chestertown boasts a strong, creative Arts community, live theatre and an award-winning Farmers Market which completes a most desirable lifestyle. More importantly, it could be your personal refuge or a family compound where the sun rises over the open fields, tor where one can watch a fox patrol the tree line. A timeless lifestyle!HOME FEATURESBoth the MAIN HOUSE (3000 sq. ft) and TENANT HOUSE at Pentridge Woods Farm are rather rare for Kent County in that they are contemporary in design with high, timbered ceilings and many large windows to view the pastoral fields. A stunning feature of the main social rooms is a large and handsome European style, slate "woodstove" that rises as a division between the kitchen and opening living rooms. Multiple French doors and casement windows flow to a 700 sq. ft deck that surrounds a brick walkway and raised gardens all punctuated by a stylish pergola. The quality of the design is enhanced with the beamed ceilings, wood floors, modern high-end baths, soapstone counters, stainless appliances, recessed lighting and central air conditioning. The charming Tenant house has many of the same features. It is located a distance from the Main House and is strategically placed at the edge of the fields with ponds nearby. A two car, over-sized garage is located adjacent to Main House. House. LOTThe property is comprised of 169 acres of open fields and woods. There are two ponds. A neighboring farmer tills the land with rotating crops. This creates income and fields that are tended. However, the opportunities for pastures and feed crops is there. The land is protected by wildfowl conservation easements and an easement which prohibits further division. A true preserved land holding. Deer hunting is allowed. A deer hunting lease is made available. HORSESFoxhunters use nearby farms to hunt in Kent County -- the northern hub of the Wicomico Foxhunt Club; and the Washington College Equestrians hold their open annual hunt at nearby Chino Farm. The neighborhood abounds in carriage driving farms as well as nationally competitive hunter jumper facilities and acclaimed sport horse breeding operations like Hilltop Farm. Waterfront public horseback riding trails are open to equestrians, western and English. Horse shows dot the annual calendar of nearby Tuckahoe Equestrian Center, as well as frequent organized trail rides.