Chestertown MD Real Estate & Homes for Sale

Well maintained Beautiful Brick Rancher nestled on 2.16 Acres in Chestertown and a short distance to Historic Downtown. 3 Spacious Bedrooms all with Hardwood Flooring and 2 Full Baths. The Primary Bath has been completely renovated with a Walk-In Tiled Shower. Living Room offering a cozy Brick Fireplace with Hardwood Flooring. Family/Kitchen Combo with Slider leading to the tranquil back yard. Enjoy the 20x40 in-ground Pool (new cover) which is great for Family Fun and Entertaining. Oversized attached 2 car Garage with ample driveway parking for guests and storage. Amazing Home updates include New Roof 2009, Windows 2018, Heat Pump 2022, Septic 2019, Well 2022. Great opportunity to own a charming home! 1 Year Home Warranty Included

Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2022, offering the perfect blend of modern comfort and peace of mind. Freshly painted with brand new carpet, this home features a bright, open floor plan ideal for both everyday living and entertaining. Enjoy the benefits of newer construction - major systems like the roof, HVAC, and water heater are all just a few years old, giving you confidence and low maintenance for years to come. Located in a desirable community with an affordable HOA that includes lawn mowing, you'll appreciate easy, low-maintenance living. Conveniently situated just minutes from shopping centers, restaurants, and everyday amenities. This move-in ready home is truly a must-see!

Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. This is an ultra efficient "green" house.

Great opportunity to own a small cottage in Chestertown. Right next to, and with direct access to the walking trails, this end of road 2 bedroom home comes with an extra lot, currently used for parking, but could also possibly be built on. Buyer to verify with county

Welcome to this charming 4-bedroom rancher nestled in the heart of historic Chestertown, offering the perfect blend of peaceful rural living and convenient access to town amenities. Enjoy easy one-level living with a functional layout and gorgeous hardwood floors that add warmth and character throughout the home. The beautiful white kitchen features stainless steel appliances, including a gas range and microwave range hood, creating a bright and inviting space for everyday living and entertaining. The home offers four main-level bedrooms, including a comfortable owner's suite with a private ensuite bathroom. Surrounded by the beauty of Maryland's Eastern Shore, this property is ideal for those who appreciate outdoor living, with countless nearby opportunities for hunting, fishing, crabbing, boating, and exploring nature. Enjoy the charm, history, shops, dining, and waterfront attractions that make Chestertown such a sought-after destination while still embracing the peace and privacy of a rural setting. Mortgage savings may be available for buyers of this listing.

Custom-Perfected Home with Luxury Finishes - Without the Luxury Price This beautifully reimagined 3-bedroom, 2-bath home (1,512 sq. ft.) sits on a generous .34-acre lot and offers high-end upgrades you'd expect to find in a designer showcase. The owners completely overhauled the home from top to bottom - correcting builder issues and enhancing every detail with thoughtful, custom touches. Step inside to discover modern farmhouse elegance, highlighted by a stunning chef's kitchen where no detail was spared. From porcelain wood-look tile floors to solid wood KraftMaid soft-close cabinetry, quartz countertops, and a massive island, this kitchen is both functional and fabulous. You'll love the hidden microwave, gold fixtures, pot filler, double Caf dishwashers, Caf refrigerator with Keurig dispenser, and brick tile backsplash - plus clever add-ons like concealed charging stations, pop-up countertop shelves, and pull-out drawers for effortless organization. The open living area features a custom shiplap accent wall, a cozy pellet stove, and custom steel handrails leading upstairs. There's a bedroom and full bath on the first floor - perfect for guests or multigenerational living. Upstairs offers two additional bedrooms and a beautifully updated bath. Outside, your private paradise awaits. The backyard is partially enclosed with a 6-ft privacy fence, surrounded by raised garden beds (with tomatoes already growing!), a water-fed garden line, French drains for excellent drainage, and a concrete patio complete with hot tub, privacy pergola with curtains, outdoor TV, and lighting for evening entertaining. The impressive Amish-built 24x30 garage is more than just parking - it's a dream workshop, featuring a 4-inch poured concrete pad with reinforced supports, mini-split HVAC, pellet stove, LED lighting, garage door opener, RV hook-up, and EV charging outlet. Additional upgrades include fresh interior paint, brick tile floors in the downstairs bath, custom window treatments on the back sliding door, and a recently completed septic and home inspection for peace of mind. Located in a community with optional HOA membership that grants access to water amenities. Enjoy easy proximity to Great Oak Marina - featuring a restaurant, beach bar, and live entertainment - plus charming Chestertown and Rock Hall, both just 12 minutes away. This is more than a home - it's a showcase of craftsmanship, comfort, and creativity, all wrapped in affordability. You truly have to see it to believe it! Want to see these updated fun features in action, there is a video to show just that! PROFESSIONAL PICTURES TO COME!

Take advantage of the Eastern Shore's amenities and quality of life in this low maintenance one floor home just a hop and a skip from the Chesapeake Bay and public beach. The Sergeant's Quarters at Tolchester Village is located less than 15 minutes from both Chestertown and Rock Hall providing nearby cultural, entertainment, and employment opportunities. The home itself has been taken care of with love and is ready for its next steward. Vaulted ceilings and spacious room sizes provide a great feel. The Shanty Bar at Tolchester Marina, just a beach cruiser or golf cart ride away, is one of the Chesapeake Bay's premier beachfront establishments serving coastal fare, fresh made boat drinks, and hosting live music on the Bay. Invest wisely in this tranquil retreat with bountiful nearby attractions.

Welcome to this stunning 2023-built home with well-designed architectural elevations! The curb appeal captures your attention and the moment you arrive, the welcoming front porch invites you to slow down, relax, and imagine enjoying a glass of iced tea from your favorite wicker chair. Step through the handsome front door into a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,535 square feet of thoughtfully designed living space. The main level features an open-concept layout with a spacious family room, dining area, and bright, well-appointed kitchen - perfect for both everyday living and entertaining. A convenient first-floor laundry room and powder room add to the home's functionality. The kitchen is designed with today's lifestyle in mind, featuring stainless steel appliances, a generous peninsula for gathering, and a large corner pantry providing abundant storage. Upstairs, the owner's suite offers a peaceful retreat with a walk-in closet and private en-suite bath complete with double vanity and walk-in shower. Three additional bedrooms share a full hall bath with double vanity, providing comfort and convenience for family or guests. The third level expands the home's versatility with a fifth bedroom, full bath, and flexible bonus space ideal for a home office, playroom, media room, fitness area, or additional storage. Ample closets throughout ensure exceptional storage options. Extras you'll love: a modern Smart Home Package offering convenience, efficiency, and peace of mind. The backyard backs to trees for added privacy, with plenty of room to add a shed, garage, or play equipment to suit your lifestyle. The thoughtfully landscaped community common area features a scenic pond with fountain, creating a welcoming neighborhood setting. Located just minutes from downtown Chestertown - known for its charming shops, restaurants, parks, waterfront atmosphere, and Washington College - you'll enjoy easy access to date nights, community events, and small-town charm at its best. This thoughtfully planned community is complete, offering a wonderful opportunity to become part of an established neighborhood. Don't miss your chance to make this exceptional home your own!

Welcome to 9816 Fairlee Road. Be Sure to Click the Virtual Tour!! This property has been meticulously cared for by the current owners and it shows. The property sits on 6.29 acres! If you want plenty of land without giving up on high end fixtures, this is the home for you. Pride of ownership shines through in this gem of a home. The paved driveway leads to a parking pad and a beautiful piece of property. This rancher gives you plenty of space both inside and out. Recently, there was an addition of a mudroom and a second owners suite. Both owners suites have their own bathroom and walk-in shower and one even has a jetted Jacuzzi tub to help you unwind after a long day. There is upgraded flooring through-out, whether it be hardwood or tile, every room feels polished and upscale. The living room includes a woodstove that was installed in 2025 along with a new chimney pipe. There is a creek directly behind your property, which means, water is just a short stroll away. Enjoy tons of natural light in the spacious kitchen where quartz countertops are partnered with a Stainless Steel Refrigerator, built-in microwave and stove. Soft-close cabinets and drawers add to the upscale feel. This home has three spacious bedrooms and three full baths. The un-finished lower level provides you with even more space for storage or it can be your very own blank canvas to finish and increase your living space. The laundry area is in the basement and the washer and dryer will stay with the home. The sliding glass door in the kitchen allows access to your deck and backyard. Enjoy the peace and quiet. Don't be surprised if you see ducks, turkey or deer, they have been known to enjoy the 6+ acres too! The water treatment system has been thoroughly maintained and will convey with the home. High Speed Talkie internet is available. New windows installed throughout most of the home in 2020. This is an Amazing Home! It is turn-key and ready to Welcome its New Owners.

PRICE IMPROVEMENT: exceptional value? Priced BELOW 2025 Appraisal!! Instant equity! NOTE: Zillow's property taxes are incorrect: correct annual property taxes are $4,338. Welcome to 103 Trafford Drive; an exceptionally maintained 3 bedroom home just minutes from downtown Chestertown. Nestled in family-friendly Coventry Farms Community, this Colonial-style residence has been recently updated in all the right places for modern convenience and classic charm. Brand new kitchen cabinets, countertops, and appliances, 5-inch oak hardwood floors, back patio, washer/dryer are just a few up the recent updates. Some of the timeless interior features include a wood burning fireplace, tray ceilings, baseboard and crown moldings, chair railings, . Inside you are greeted by a traditional layout with a formal dining room and formal living room or office space. The front of the home flows seamlessly to the back where the heart of the home is: the newly renovated kitchen and living room space punctuated with a wood-burning fireplace. Recent kitchen improvements include: custom maple wood cabinets, quartz countertops, Frigidaire and LG stainless steel appliances, and a reverse osmosis water treatment system. The spacious and private back yard has a thick tree line to the back and has been elevated by a new concrete patio and wood steps and newly planted pine trees for additional privacy. Going upstairs one will find brand new 5-inch red oak hardwood floor throughout: and no thresholds! The spacious primary bedroom features an ensuite bath with jetted soaking tub and an oversized walk-in closet. The full basement could easily be turned into a fourth bedroom with electric, lighting, ductwork, and roughed-in plumbing all ready to go. Oversized two-car garage offers additional storage or parking. Don't miss this opportunity. This stunning home has been meticulously maintained and upgraded in all the right spots; offering exceptional elegance and modern comfort. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals and an award-winning weekly Farmer's Market. Less than 90 minutes to Philadelphia and Washington D.C. Come see what Chestertown life is all about. Some furnishings may convey.

Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm.

Welcome to 208 Central Drive, located in the desirable Chester Harbor community just minutes from historic Chestertown. This charming 3-bedroom, 1-bath home offers a wonderful blend of comfort, convenience, and value. It sits on 3 lots totaling approximately 0.55 acres, surrounded by mature trees and landscaping. Step inside to a bright, move-in-ready interior featuring brand-new wood flooring (2025) in the living room, hallway, and first bedroom. The home was thoughtfully updated with new lighting and ceiling fans throughout (2024-2025). The bathroom has been fully updated with a new tub/shower combination (2024), a stylish vanity, updated lighting and mirror (2024), a newer toilet (2023), and new flooring (2024). The kitchen includes a reverse osmosis water filtration system (2023), a new water filter (February 2026), and a stove/oven that is approximately five years old. Major systems have also been addressed, including a new water heater (2025), septic system inspection and pumping (2025), and three new electric heating units (2023). Outside, the expansive yard is a standout feature. Recently landscaped in 2024 and enhanced with fresh grass seed and treatment in 2025, the property offers plenty of space to enjoy. Outside includes a crab apple tree, a fig tree, a white pear tree, 2 white dogwood trees, and forsythia. Brand new rear screen door (2026) and a newly installed rear fence (2025) enhance both privacy and functionality, creating an ideal setting for relaxing or entertaining. Set on a generous lot with thoughtful updates throughout, this property offers exceptional value in a prime location just minutes from historic Chestertown, shops, dining, and waterfront. Enjoy water access to Rosin Creek in the community, which adds to the home's appeal for outdoor enthusiasts.

Practically brand new and just 2 years young, this beautifully maintained home is perfectly situated in a desirable water-oriented community - offering the best of Eastern Shore living! Located in the Queen Anne's County school district and just minutes from downtown Chestertown, you'll love the convenience paired with the peaceful setting. Enjoy easy access to the Chester River - you can drive your boat to the community ramp at the end of the street, or even take a nice short walk down to the water, to spend your days crabbing, fishing, kayaking, or simply soaking in the waterfront lifestyle. Inside, this 3-bedroom, 2 full bath home features durable and stylish LVP flooring throughout and a thoughtfully designed split floor plan. The spacious primary suite is privately situated on one side of the home and offers a walk-in shower, dual vanity, and a beautifully appointed bath. On the opposite side, you'll find two additional bedrooms and a full bath with a tub/shower combo - ideal for guests or flexible living. The kitchen and living room are centrally located, creating an inviting and functional space for everyday living and entertaining. A standout bonus - an unfinished upstairs area of 544 additional SF, already in place and ready for your vision! Use it for storage now or finish it off for additional bedrooms, a home office, or recreation space. Step outside and enjoy both a charming front porch - perfect for morning coffee - and a massive back deck ideal for entertaining, grilling, or simply relaxing while taking in the peaceful surroundings. The generously sized yard with mature trees offers both privacy and room to enjoy the outdoors. Even more exciting - the county has indicated plans to pave the road in the near future. Added perk: fiber optic Talkie Internet is already available at the property, making working from home or streaming a breeze. Move-in ready, full of potential, and located in a charming waterfront community - this one checks all the boxes!

MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The Shanty Beach Bar, dining & shopping. just a very quick trip to entertainment, or boating. Great location, private lot just 10 minutes from downtown Chestertown or Rock Hall where you can enjoy shops, marinas, dining and regular events. Level lot with plenty of potential.

Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the home. On the second level you'll find two bedrooms and two bathrooms. The third bedroom encompasses the entire third floor and has a great view of the Chester River. You'll enjoy the large back balcony with views of historic Chestertown. The third level could be used as the primary bedroom; there is a large full bathroom and closet. The townhomes have a private driveway, so you'll never worry about finding a parking space. Take advantage of the easy access to Wilmer Park and Chestertown Marina, located just across the street. This townhouse is located in the heart of all Chestertown has to offer! Just a short distance to shops, restaurants, renowned bakeries, and the year-round farmers market by Fountain Park. You will have a front-row seat to the Downrigging Festival! Not to mention the many festivals held in downtown Chestertown throughout the year.

If you're looking for that secluded spot, with land, room to grow and stretch, and don't mind a project, look no further! Dream location on a private road, backing to farmland, and yet just a few miles outside of downtown Chestertown! The house is midway through a full renovation. Walls are in place, electric run, plumbing roughed-in, new siding and a brand New HVAC! All the hard stuff is done! The floor plan is open and airy with a large foyer that looks out through new french doors, to the expansive backyard. The master is good size with its own en suite bathroom. Two further bedrooms off the living room with a good size family bathroom. A seperate Laundry and mudroom make life easy for busy lives. All of this set in lush 2 acres of farmland, just a few minutes outside of Chestertown. What more could you ask for?

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates - making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations. Ask about Special Financing Offers and how to get $7,500 or more in closing help from the builder's preferred lender and on select models, while they last!

Previous Buyer failed to perform - Your opportunity has come around again - Don't miss out this time. FULL RENOVATION PROJECT - Prime Chestertown Location Priced for Immediate Equity Creation. This 3-bedroom, 1-bath single-family home at $115,000 represents a clear value-add opportunity in one of Chestertown's most walkable corridors. With estimated renovation investment of $60K-$80K+, comparable renovated properties in this location are selling for $275K-$300K, creating potential equity of $80K-$125K for buyers with vision and capability. Close proximity to Washington College creates built-in rental demand from students, faculty, and staff. Plus easy access to Downtown Chestertown shops, restaurants, and waterfront parks are minutes away on foot. Starbucks and grocery stores are easily accessible. This is a prime location renovation opportunity where comparable updated homes command premium pricing. The renovation reality. This property requires full renovation and is priced accordingly. Systems, finishes, and layout will need comprehensive updating. Estimated investment ranges from $60,000 to $80,000+ depending on finish level and scope decisions. This is a project for experienced investors, renovation contractors, or buyers with construction capability who understand forced appreciation through strategic improvements. The opportunity math works. Purchase at $115,000. Invest $60K-$80K in renovations. All-in cost: $175K-$195K. Recent comparable sales for fully renovated 3-bedroom homes in walkable Chestertown locations are selling in the $275K-$300K range. Your potential equity position: $80,000 to $125,000 upon completion. Multiple exit strategies. Flip after renovation for immediate profit. Hold as rental property serving Washington College market with strong rental history in the area. Owner-occupy and build instant equity while creating your ideal home. The location flexibility supports whatever investment strategy fits your goals. Property sold AS-IS. Serious buyers should conduct thorough inspections and due diligence. This is a renovation project, not a cosmetic update - price reflects condition and opportunity. Act quickly on clear value plays. Properties offering this equity spread in prime walkable locations move fast when priced correctly.

Tucked away just south of the scenic Chester River and moments from the timeless charm of Chestertown, this inviting home offers a warm and welcoming retreat in the heart of Queen Anne's County. Surrounded by the natural beauty of Maryland's Eastern Shore, the setting feels peaceful and relaxed - where quiet mornings and golden sunsets become part of everyday life. Inside, the home is designed for comfort and easy living, featuring a desirable first-floor primary suite that provides both privacy and convenience. The spacious family room, anchored by a cozy gas fireplace, creates the perfect gathering space, while the rear screened-in porch invites you to unwind and enjoy the tranquil surroundings. Upstairs, you'll find two additional bedrooms along with a versatile bonus room - ideal as a home office, playroom, or craft space - plus walk-in attic storage for added functionality. Outdoor living shines with a brand new deck complete with a hot tub, perfect for relaxing or entertaining under the stars. An oversized two-car garage and ample parking accommodate your lifestyle with ease, including space for an RV, a boat, or both. Recent updates offer peace of mind, including a new roof (2024), HVAC system and hot water heater within the last five years, and the added benefit of a one-year Choice Home Warranty. Blending comfort, flexibility, and Eastern Shore charm, this home is a wonderful opportunity to enjoy a lifestyle that feels both relaxed and connected. Schedule your private tour and make this home yours.

New price, same stunning home!!! Stop scrolling - this beauty is ready for new owners to move in and make lasting memories! Welcome to this exceptional custom-built home offering nearly 3,000 sq. ft. of beautifully designed living space where luxury, comfort, and style come together effortlessly. Featuring 4 bedrooms and 2.5 baths, this home is perfectly situated on a level 1 acre lot directly across from the scenic Chester River. From the moment you step inside, you'll love the expansive open-concept layout, soaring ceilings, and upscale finishes throughout. The gourmet kitchen is a true showstopper, complete with a large island, sleek quartz countertops, and a hidden pantry/workstation designed for both beauty and function. The inviting stone fireplace creates the perfect focal point for gathering and entertaining. Additional highlights include spacious walk-in closets, a convenient Jack-and-Jill bath, an oversized laundry room with abundant storage, a screened-in porch with vaulted ceilings, and an oversized 2-car garage. The luxurious primary suite offers a private retreat with a spa-inspired tiled shower, while the charming front porch invites you to relax and enjoy peaceful river breezes. Upstairs, the massive fourth bedroom provides endless flexibility, ideal for a recreation room, theatre room, or home office. Located just minutes from the historic waterfront town of Chestertown, founded in 1706, you'll enjoy charming boutiques, local restaurants, seasonal festivals, the popular Farmers Market, and endless opportunities to experience the beauty of the Chester River. Home to Washington College, the area perfectly captures the charm and lifestyle of Maryland's Beautiful Eastern Shore. Select photos have been virtually enhanced to showcase the home's full potential. Don't let it slip away. Contact us today for your private tour!

A Place Full of Possibility in Byford Development Tucked in the heart of the Byford community, just minutes from everything Chestertown has to offer, this welcoming rancher is ready for its next chapter. Step inside and feel the charm of traditional hardwood floors, the glow of a wood-burning fireplace in the spacious family room, and the comfort of a home that's been well-loved. The layout flows with ease - a bright formal living room for gathering, three cozy bedrooms, and a cheerful kitchen with space for morning coffee at a small table. Downstairs, a partial unfinished basement offers room for storage, hobbies, or future projects waiting to take shape. Outside, a detached two-car garage sits beside a wide yard with plenty of room to play, garden, or simply relax on the patio. The home does call for some updating, but that's part of its charm - a chance to create something that's uniquely yours. Come see the potential and picture how you'll make this lovely Byford property your own - a home where new memories are waiting to be made.

Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors, and Andersen double-hung tilting sash windows.The welcoming front porch overlooks manicured flower beds that enhance curb appeal, while the private backyard provides the perfect setting for weekend gatherings and cookouts or just outdoor relaxation. Inside, the home has been thoughtfully renovated from top to bottom. Recent updates include a Mitsubishi Mini-Split heating and cooling system,Rinnai propane instant hot water heater, and 200-amp electrical service with all-new wiring, fixtures, and recessed lighting throughout. The kitchen is a true showstopper that is completely transformed with new cabinetry, quartz countertops, a center island, stainless steel appliances, and a vented range hood. Refinished rustic hardwood floors run throughout the main level, seamlessly blending old world craftsmanship with modern design. A separate Laundry room features a new washer and dryer with Electric Hookups. Upstairs, you'll find comfortable bedrooms with Shaw carpeting and pet-proof padding and a beautifully updated bathrooms featuring tiled walls and floors, new vanity, and modern fixtures. The dry basement offers a wide step entrance from Laundry Room with excellent storage space, a new 200-amp electric panel, vapor barrier, and plenty of room for a workshop or home gym or Man Cave. Enjoy the best of in-town living with everything you need just a short stroll away. Schedule your tour today and fall in love with this move-in ready gem

New photos just added - capturing the truly one-of-a-kind gardens now in full bloom! This is a property you need to experience in person to fully appreciate the timeless character and breathtaking setting of this remarkable legacy home. The Bedingfield Hands House, circa 1750, traces its roots back to pre-revolutionary times and has a story to tell. One of the few downtown homes to offer a large front courtyard, the property features beautifully landscaped gardens and a mature magnolia tree creating a private and welcoming outdoor retreat. Offering approximately 2,472 square feet, the home includes three generously sized bedrooms and three-and-a-half updated bathrooms with elegant details throughout, including crown moulding, original wide-plank hardwood floors, and timeless architectural charm. Major renovations completed in the 1950s - include a kitchen, laundry room, and baths - while preserving the home's historic integrity. Central heating and air conditioning provide comfortable modern living within this classic setting. The property is also one of the few downtown homes to include a garage. Currently operating as one of the most successful Airbnbs in the area with a strong rental history ($32K in bookings last year!), this property offers the best of both worlds - an ideal vacation home and a turn-key income-producing investment. Furniture is negotiable. Ideally located in the heart of Chestertown's historic district, the home is just steps from art galleries, gift shops, the local farmers market, and beloved annual events like the Chestertown Tea Party Festival, Downrigging Weekend, and the Dickens of a Christmas. The Chester River located just down the street offers endless opportunities for boating and waterfront recreation, while the town itself maintains a relaxed pace of life where history, culture, and community come together. A rare and remarkable offering, the Bedingfield Hands House now stands ready for its next owner to continue its story - preserving its past, enjoying its present, and carrying its legacy forward for generations to come.

Wait until you see this! Impecably maintained brick house on nearly 20 acres, overlooking a pond with tons of privacy. 2 large outbuildings. High-end upgrades and fixtures. The house has 4 bedrooms and 3.5 baths. A primary owner's suite on the main floor and an additional owner's suite on the second floor. Beautiful hardwood floors throughout. The main floor features a bar room and an office. Kitchen with marble countertops and a huge professional refrigerator. Fully finished basement. 2 car attached garage. The first outbuilding is a office space with 2 private offices, a conference room, a gym, kitchenette and half bath. The second outbuilding features 5 garage bays and a finished area that serves as a family room with kitchenette. This property is nothing short of spectacular.

Charming and inviting! Welcome to 139 Prospect St., a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in kitchen - perfect for everyday living and easy entertaining. A private hallway leads to a generously sized primary bedroom and two additional spacious bedrooms. Outside, enjoy off-street parking and a large, deep backyard ideal for relaxing, gardening, or gathering. Conveniently located just moments from downtown Chestertown's shops, restaurants, and local attractions, this property is a wonderful opportunity as a full-time residence, weekend retreat, or investment property. An exceptional value just minutes from the charm and amenities of historic downtown Chestertown! Mortgage savings may be available for buyers of this listing.