Chestertown MD Real Estate & Homes for Sale

74 Properties Found

Sort Results:
1–25 of 74 properties displayed
Refine Property Search
Page 1 | 2 | 3 of 3    Prev | Next
Beds:
2
Baths:
3.00
Sq.Ft.:
1,857
Status:
NEW LISTING
MLS#:
MDKE2006320
Type:
Single Family-Detached
Subdivision:
Chestertown
Lot size:
2 Acres
Year built:
1977
Courtesy: Chesapeake Real Estate Associates, LLC 443-215-4663
View additional info

ADDITIONAL INFORMATION

Welcome to 24295 Langford Road in Chestertown, Maryland—a rare opportunity to own a peaceful slice of the countryside on 2 beautiful acres surrounded by farmland. Just minutes from downtown Chestertown, this property offers the perfect balance of privacy and convenience. If you’ve been searching for a home away from the hustle and bustle, this is the one. The classic brick rancher features over 1,800 square feet of living space with a full, unfinished basement offering endless potential for storage, a workshop, or future expansion. Inside, you’ll find 2 comfortable bedrooms, a small room that could serve as dressing room, den or office, 2.5 baths, along with thoughtful details such as elegant pocket doors that enhance both function and flow. A cedar closet adds a touch of luxury while providing ideal storage for clothing and linens. A standout feature of the home is the inviting three-season room addition, where you can relax and take in serene views of the backyard and the surrounding natural beauty. Wildlife is abundant—enjoy frequent sightings of deer, eagles, and more right from your own home. The property also includes a very large outbuilding, ideal for a variety of uses. Whether you’re looking to run a home-based business, pursue hobbies, or simply need space to store vehicles, boats, or equipment, this versatile structure offers incredible flexibility. It could even be finished into the ultimate workspace or creative studio. With its peaceful setting, generous acreage, and functional features, this property is a unique find in today’s market.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,785
Status:
NEW LISTING
MLS#:
MDKE2006520
Type:
Single Family-Detached
Subdivision:
Historic District
Lot size:
0.14 Acres
Year built:
1914
Courtesy: Cross Street Realtors LLC 410-778-3779
View additional info

ADDITIONAL INFORMATION

Prime location in Downtown Chestertown’s Historic District offering approximately 1,785 square feet of practical living space on three levels with 4 off-street parking spaces. The “RB” zoning also provides flexibility for live/work arrangements, and the property has rare building expansion potential to accommodate family and/or business growth.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,817
Status:
NEW LISTING
MLS#:
MDKE2006516
Type:
Single Family-Detached
Subdivision:
Crestview
Lot size:
0.73 Acres
Year built:
2017
Courtesy: Cross Street Realtors LLC 410-778-3779
View additional info

ADDITIONAL INFORMATION

Nestled in the desirable Crestview neighborhood, this beautifully maintained rancher built by respected local builder KRM Construction offers the perfect blend of quality craftsmanship, comfort, and modern convenience. Built in 2017, this 3 bedroom, 2 bathroom home features an inviting open layout with luxury plank hardwood flooring throughout the main living areas, granite countertops, abundant cabinet storage, and a cozy propane fireplace. The spacious primary suite includes a large walk-in closet and a luxurious en-suite bath complete with a soaking tub and separate shower. Enjoy relaxing mornings on the screened porch or unwind evenings around the fire pit on the paver patio just off the living room. Additional highlights include a 2-car attached garage, sprinkler system, hot water on demand, new propane furnace installed in 2026, and new dryer in 2025. Conveniently located close to all of Chestertown amenities, with a voluntary HOA of just $100/year. Showings begin 5/22 — this is one you won’t want to miss!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,666
Status:
NEW LISTING
MLS#:
MDQA2017354
Type:
Single Family
Subdivision:
Ducks Neck
Lot size:
0.53 Acres
Year built:
1976
Courtesy: Coldwell Banker Chesapeake Real Estate Company 410-778-0330
View additional info

ADDITIONAL INFORMATION

Well priced 3 bedroom, 2 bath double wide in Duck Neck, Queen Annes County situated on a half an acre and shed , man cave and car ports included. House has a metal roof. Close to the Chester River and minutes from Deep Landing and Chestertown.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,314
Status:
NEW LISTING
MLS#:
MDKE2006556
Type:
Single Family
Subdivision:
Tolchester
Lot size:
0.17 Acres
Year built:
1955
Courtesy: Coldwell Banker Chesapeake Real Estate Company 410-778-0330
View additional info

ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,896
Status:
NEW LISTING
MLS#:
MDKE2006586
Type:
Single Family-Detached
Subdivision:
The Village At Chestertown
Lot size:
0.09 Acres
Year built:
2023
Courtesy: Long & Foster Real Estate, Inc. 410-479-3993
View additional info

ADDITIONAL INFORMATION

Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an open 1st floor features a bright white kitchen and dining area open to a large living room for entertaining and a 1/2 bathroom. The 2nd floor features 3 bedrooms 2 full bathrooms. The primary feature private bath and large closet. The exterior has large backyard for friends and family concrete driveway and freshly manicured yard. Call today for private showing today.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,120
Status:
NEW LISTING
MLS#:
MDQA2016900
Type:
Single Family-Detached
Subdivision:
Ducks Neck
Lot size:
0.51 Acres
Year built:
2024
Courtesy: Chesapeake Real Estate Associates, LLC 443-215-4663
View additional info

ADDITIONAL INFORMATION

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!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,440
Status:
NEW LISTING
MLS#:
MDKE2006526
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
2.16 Acres
Year built:
1965
Courtesy: Keller Williams Realty 302-360-0300
View additional info

ADDITIONAL INFORMATION

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

Beds:
5
Baths:
4.00
Sq.Ft.:
2,534
Status:
NEW LISTING
MLS#:
MDKE2006510
Type:
Single Family-Detached
Subdivision:
The Village At Chestertown
Lot size:
0.11 Acres
Year built:
2023
Courtesy: CENTURY 21 New Millennium 410-266-9005
View additional info

ADDITIONAL INFORMATION

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!

Beds:
5
Baths:
4.00
Sq.Ft.:
2,688
Status:
NEW LISTING
MLS#:
MDKE2006478
Type:
Single Family-Detached
Subdivision:
Great Oak Estates
Lot size:
1.01 Acres
Year built:
1989
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
View additional info

ADDITIONAL INFORMATION

Nestled in the natural serene of Great Oak Estates, this beautiful 5 bedroom, 3.5 bathroom Nanticoke Home offers a flexible floor plan, updated kitchen, spacious backyard, and brand new Florida/Sun room, designed for both relaxation and entertaining. The heart of the home feautures a gourmet kitchen with granite counter tops, SS appliances, custom built ins, and connects to the family room with an amazing built in wood stove, warming the entire home. Sitting on a generous 2 acre lot (not reflected on tax record), and surrounded by lush farmland, this property offers you so much potential. Keep the extra lot as a natural buffer, or build a garage/workshop/granny annex, or just sell it on. You can't go wrong! Great Oak Estates offer direct access for its residents ($100 annually) to all the Marina amenities including: Outdoor pool, restaurant, 9 hole golf course, picnic and playground area by the water. And a beautiful sandy beach on the calm waters of Fairlee Creek.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,325
Status:
NEW LISTING
MLS#:
MDKE2006482
Type:
Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.41 Acres
Year built:
1960
Courtesy: Redfin Corporation 484-962-0034
View additional info

ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,512
Status:
NEW LISTING
MLS#:
MDKE2006486
Type:
Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.34 Acres
Year built:
2020
Courtesy: Coldwell Banker Chesapeake Real Estate Company 410-778-0330
View additional info

ADDITIONAL INFORMATION

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 Café dishwashers, Café 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!

Beds:
4
Baths:
3.00
Sq.Ft.:
1,972
Status:
Active
MLS#:
MDKE2006498
Type:
Single Family-Detached
Subdivision:
The Village At Chestertown
Lot size:
0.1 Acres
Year built:
2022
Courtesy: Cross Street Realtors LLC 410-778-3779
View additional info

ADDITIONAL INFORMATION

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!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,784
Status:
Active
MLS#:
MDQA2017090
Type:
Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.6 Acres
Year built:
2004
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
View additional info

ADDITIONAL INFORMATION

Beautiful, Well-Maintained 3BR/2.5BA Home with Upgrades – 215 Fairview Drive Owner pride shines inside and out in this exceptional home located in the charming town of Chestertown, nestled in Queen Anne's County. Built in 2004 and offering 1,784 sq ft of living space, this property blends comfort, functionality, and thoughtful updates—perfect for today’s lifestyle. This inviting home features 3 bedrooms and 2.5 baths, along with a 2-car garage and a newly paved blacktop driveway. Inside, enjoy a bright, functional layout with brand-new carpet throughout the entire upstairs, giving the home a fresh, move-in-ready feel. Additional updates include a new roof, offering peace of mind for years to come. The spacious living areas flow seamlessly, making it ideal for both everyday living and entertaining. Step outside to a large backyard with plenty of space to relax and enjoy. The property includes a children’s play area and a vegetable garden, perfect for outdoor fun and homegrown produce. Highlights: 3 Bedrooms 2.5 Bathrooms 1,784 Sq Ft Built in 2004 2-Car Garage New Roof New Carpet Upstairs Blacktop Driveway Large Backyard Children’s Play Area Vegetable Garden Conveniently located just minutes from downtown Chestertown, Washington College, local shops, dining, and the waterfront, this home offers the perfect balance of peaceful living and accessibility. Schedule your showing today—this move-in-ready home won’t last long! Professional pictures coming 5/7 .

Beds:
2
Baths:
2.00
Sq.Ft.:
1,082
Status:
Active
MLS#:
MDKE2006494
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.08 Acres
Year built:
1900
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
View additional info

ADDITIONAL INFORMATION

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

Beds:
3
Baths:
5.00
Sq.Ft.:
3,047
Status:
Active
MLS#:
MDKE2006496
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.14 Acres
Year built:
1780
Courtesy: Coldwell Banker Chesapeake Real Estate Company 410-778-0330
View additional info

ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,280
Status:
Active
MLS#:
MDKE2006446
Type:
Townhouse
Subdivision:
Chester Arms
Lot size:
0.13 Acres
Year built:
2025
Courtesy: Real Broker, LLC 855-450-0442
View additional info

ADDITIONAL INFORMATION

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!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,352
Status:
Active
MLS#:
MDKE2006342
Type:
Single Family
Subdivision:
None Available
Lot size:
2.41 Acres
Year built:
2007
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
View additional info

ADDITIONAL INFORMATION

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?

Beds:
3
Baths:
3.00
Sq.Ft.:
1,944
Status:
Active
MLS#:
MDKE2006416
Type:
Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.23 Acres
Year built:
2007
Courtesy: Coldwell Banker Chesapeake Real Estate Company 410-778-0330
View additional info

ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,877
Status:
Active
MLS#:
MDQA2016560
Type:
Single Family-Detached
Subdivision:
Sarah Skipper Lands
Lot size:
1.01 Acres
Year built:
2026
Courtesy: Clark & Co Realty, LLC 410-827-4663
View additional info

ADDITIONAL INFORMATION

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!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,304
Status:
Active
MLS#:
MDQA2016812
Type:
Single Family-Detached
Subdivision:
Char Nor Manor
Lot size:
0.34 Acres
Year built:
1971
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

This charming 3 bedroom, 2 bathroom home offers the perfect blend of comfort, convenience, and functionality that has major upgrades including Fresh Paint throughout, Renovated Primary Bath and New carpet. The bonus office room is an essential for remote work! The property also features a large 2-car garage/workshop, you’ll have plenty of room for vehicles, projects, or storage. Step inside to a spacious living room that flows seamlessly into the kitchen, complete with gorgeous granite countertops and newer stainless-steel appliances. The cozy primary bedroom is complete with a wood-burning fireplace ideal for relaxing evenings. Enjoy your morning coffee on the welcoming front porch just across the street from views of the Chester River, or host gatherings in the fenced-in backyard with space for play and gardening. You also have peace of mind with a newer HVAC system (2023) and solar panels for a more energy efficient home! Located towards the end of this peaceful street, you’re close to Chestertown’s historic charm, Washington College, a nearby boat ramp, and tax-free shopping just across the Delaware line and still located in Queen Anne's County!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,120
Status:
Active
MLS#:
MDQA2016836
Type:
Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.55 Acres
Year built:
1978
Courtesy: Redfin Corp 301-658-6186
View additional info

ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
4.00
Sq.Ft.:
4,145
Status:
Active
MLS#:
MDKE2006350
Type:
Single Family-Detached
Subdivision:
Prestwick
Lot size:
2.29 Acres
Year built:
2018
Courtesy: Taylor Properties 301-970-2447
View additional info

ADDITIONAL INFORMATION

Exceptional custom-built 2018 one-level home on 2.28 private acres in the highly sought-after Prestwick community, ideally nestled just off the Chester River Yacht & Country Club. This thoughtfully designed residence offers a seamless blend of comfort, elegance, and functionality, featuring an open-concept layout with soaring ceilings and abundant natural light throughout. The gourmet kitchen showcases timeless off-white cabinetry, granite countertops in warm earthy tones, and a coordinating backsplash, all opening effortlessly to the expansive great room anchored by a striking stone fireplace—perfect for both everyday living and entertaining. Enjoy multiple outdoor living options including a screened porch, rear porch, and patio—each offering peaceful wooded views and backing to open space for a truly private, tranquil setting that invites you to unwind and explore. The home features rich hardwood flooring, tile, fresh carpet, and fresh neutral paint throughout. The spacious primary suite, privately situated, offers a tray ceiling, two walk-in closets, and a luxurious en-suite bath, while three additional bedrooms and two full baths are thoughtfully positioned on the opposite side—ideal for guests, family, or a dedicated home office. Additional highlights include a welcoming front porch, partially finished basement with half bath and exterior access, and flexible space for recreation, hobbies, or future customization. The attached 2-car garage is complemented by a stairway off the laundry room leading to unfinished space above—perfect for expansion or storage. A standout feature is the detached custom 3-car garage equipped with a car-lift, work benches, cabinets, a mini-split system and unfinished upper level—an incredible opportunity for additional living space. Surrounded by nature, this property offers a rare combination of privacy, craftsmanship, and subtle details that are best experienced in person. Don’t miss this rare opportunity! Built by Alton E. Darling Construction.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,232
Status:
Active
MLS#:
MDKE2006390
Type:
Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.33 Acres
Year built:
2003
Courtesy: Doug Ashley Realtors, LLC 410-810-0010
View additional info

ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,499
Status:
Active
MLS#:
MDKE2006378
Type:
Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.35 Acres
Year built:
2020
Courtesy: Chesapeake Real Estate Associates, LLC 443-215-4663
View additional info

ADDITIONAL INFORMATION

Offers due Wednesday 4/22 by 6PM! Welcome to this beautifully upgraded 3-bedroom, 2-bath Cape Cod, just six years young and perfectly situated in the sought-after Chesapeake Landing community! Ideally located directly across from the Turtle Trail and Millbrook Pond, you’ll love the peaceful, water-oriented setting with nearby access to a community boat ramp, fishing pier, Worton Creek marina, and new restaurant opening soon. This is far from your typical builder-grade home—the current owners have thoughtfully enhanced every inch. The kitchen truly shines with custom upgrades including a built-in pantry, stunning butcher block countertops, island addition, and bar-top seating—plus a full suite of high-end appliances (yes, even a refrigerator with a large touchscreen!). The flexible floor plan offers the best of both worlds with a dedicated dining room and a first-floor bedroom, ideal for guests or one-level living. Outside, enjoy an extended patio, freshly graded yard, and a new storage shed, creating the perfect outdoor space for relaxing or entertaining. With motivated sellers who have already found their next home, this is an incredible opportunity to move right in and start enjoying all that Chesapeake Landing has to offer. Don’t miss your chance to make it yours!

Refine Property Search
Page 1 | 2 | 3 of 3    Prev | Next
1–25 of 74 properties displayed
Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

© BRIGHT, All Rights Reserved - The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Xome Inc. participates, and is provided by BRIGHT through a licensing agreement. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.



Chestertown 21620 Real Estate

Chestertown is located in Maryland. Chestertown, Maryland 21620has a population of 5,557. Chestertown 21620 is more family-centric than the surrounding county with 21.45% of the households containing married families with children. The county average for households married with children is 15.86%.

The median household income in Chestertown, Maryland 21620 is $44,665. The median household income for the surrounding county is $64,451 compared to the national median of $69,021. The median age of people living in Chestertown 21620 is 39.1 years.

Chestertown Weather

The average high temperature in July is 87 degrees, with an average low temperature in January of 25.4 degrees. The average rainfall is approximately 45.1 inches per year, with 13.9 inches of snow per year.

Chestertown Map

Chestertown Real Estate Market Conditions

  • Median sales price

    $272,500
    14.5%
    change since last quarter
  • # Active listings

    119
    30-day change

Chestertown Schools and Demographics

Education near Chestertown, MD

City County
High School Graduates 88.37 90.6
College Degree - 2 year 5.13 5.64
College Degree - 4 year 42.33 37.48
Graduate Degree 16.24 9.64
Expenditures per Student 19,095 19,095
Students per Teacher 10.4 10.4

Elementary Schools near Chestertown, MD

Grades Students P/T Ratio ZIP
Centreville Elementary School PK - 02 550 17.4 21617
Church Hill Elementary School PK - 04 314 15.2 21623
Galena Elementary School PK - 05 190 17.4 21635
H. H. Garnett Elementary PK - 05 233 11.5 21620
Kennard Elementary School 03 - 05 513 17.7 21617
Millington Elementary School PK - 05 186 13.2 21651
Rock Hall Elementary School PK - 05 187 14.3 21661
Worton Elementary School PK - 05 277 12.7 21678

Middle Schools near Chestertown, MD

Grades Students P/T Ratio ZIP
Centreville Middle School 06 - 08 537 14.9 21617
Kent County Middle School 06 - 08 439 12.9 21620

High Schools near Chestertown, MD

Grades Students P/T Ratio ZIP
Kent County High School 09 - 12 594 13.8 21678
Queen Anne's County High School 09 - 12 1,102 14.3 21617

Demographics near Chestertown, MD 21620

Zip Code City
Neighborhood Type Small Town
Population 5,557 19,335
Population Density 2,016 70
Median Age 39.1 47.1
People per Household 1.7 2.1
Median Household Income 44,665 64,451
Average Income per Capita 28,645 39,658

Real estate near Chestertown