Chestertown, MD Homes For Sale | Homes.com
Save This Search
Add Filters

190 Chestertown, MD Homes For Sale

Sort by: Closest Match
New
house for sale
3 bds | 3 ba | -- sqft

307 Flyway Lane, Chestertown, MD 21620

This Is It! Situated on 1 acre in the Flyway on a cul-de-sac is a split bedroom open plan design custom-built Ranch home. Just shy of 2,500 sq.ft., this 3 bedroom, 2.5 bathroom home also features a 4-season room, great room, separate living room with french doors, and finished bonus room above the insulated 2-car garage. The 1,500 gal septic will accommodate more bedrooms if desired. From the crawl space to the roof to the sizeable workshop/shed, this home has been meticulously cared for and loved over the years. Excellent Sellers to follow!
Save
View Home
$329,000
View Est. Payment
house for sale
3 bds | 3 ba | 2,320 sqft

Chatham Executive Villa, Chestertown, MD 21620

This to-be-built home is the "Chatham Executive Villa" plan by Covell Communities, and is located in the community of The Chester River Landing. This single family plan home is priced from $479,900 and has 3 bedrooms, 2 baths, 1 half baths, is 2,320 square feet, and has a 1-car garage. The Builder describes this home as: "The Winged Island Kitchen, Family Room and Dining Room, of the Chatham Executive home style, are arranged in an open layout that is more than substantial space for entertaining guests or family.. The Second Floor Owners Suite is located in the rear of the home for maximum privacy and is generous in size. For further Customization, add a Sleeping Porch or Bonus Room". Listing provided by newhomesource.com.
Save
View Home
$479,900+
View Est. Payment
house for sale
3 bds | 3 ba | 2,350 sqft

114 Landing Lane, Chestertown, MD 21620

This new construction, quick move-in home is the "Chatham Legacy Villa" plan by Covell Communities, and is located in the community of The Chester River Landing at 114 Landing Lane, Chestertown, MD-21620. HOT HOME: Covell Communities Chatham Legacy Villa. This single family inventory home is priced at $509,900 and has 3 bedrooms, 2 baths, 1 half baths, is 2,350 square feet, and has a 1-car garage. The Builder describes this home as: "This is the waterfront living experience you have been dreaming about!.Community Marina, Pool, Walking Trails, Parks and so much more all with a stunning view of the the Chester River.Huge second floor outdoor terrace is the ultimate spot for entertaining family and friends while the first floor living is perfectly designed for everyday needs. Covell Communities' design team has exceed all expectations with this all new adaptation of the fabulously successful series of homes.Come see what the buzz is all about!Final phase of this awarding winning community now selling.Don't miss you chance to own a piece of your dreams.Opportunity only knocks once". Listing provided by newhomesource.com.
Save
View Home
$509,900
View Est. Payment
house for sale
3 bds | 3 ba | 2,350 sqft

Alexandria Classic, Chestertown, MD 21620

This to-be-built home is the "Alexandria Classic" plan by Covell Communities, and is located in the community of The Chester River Landing. This plan home is priced from $599,900 and has 3 bedrooms, 2 baths, 1 half baths, is 2,350 square feet, and has a 2-car garage. The Chester River Landing features Townhouse homes by Covell Communities with amenities such as beach, marina, park, pond, pool, trails, views, and waterfrontlots. Listing provided by newhomesource.com.
Save
View Home
$599,900+
View Est. Payment
New
house for sale
3 bds | 2 ba | 1,144 sqft

102 Dutchess Rd, Chestertown, MD 21620

Beautiful 3 BR, 2BA Rancher situated on a corner lot with mature shade trees. Short walk to Rosin Creek and public boat launch. Corian counters, separate laundry room off the kitchen. Nice 10x15 screened-in porch.
Save
View Home
$190,000
View Est. Payment
house for sale
3 bds | 3 ba | 2,350 sqft

214 Landing Lane, Chestertown, MD 21620

This new construction, quick move-in home is the "Alexandria Classic" plan by Covell Communities, and is located in the community of The Chester River Landing at 214 Landing Lane, Chestertown, MD-21620. This inventory home is priced at $614,900 and has 3 bedrooms, 2 baths, 1 half baths, and has a 2-car garage. The Chester River Landing features Townhouse homes by Covell Communities with amenities such as beach, marina, park, pond, pool, trails, views, and waterfrontlots. Listing provided by newhomesource.com.
Save
View Home
$614,900
View Est. Payment
house for sale
4 bds | 3 ba | -- sqft

209 N Mill St, Chestertown, MD 21620

This property is now under auction terms. The property is subject to a 5% buyer~s premium pursuant to the Auction Terms & Conditions (minimums may apply). All auction assets will be sold subject to seller approval.This lovely historic home has a lot of potential & appeal, which includes beautiful hard wood floors, silestone counter tops and cherry cabinets in the kitchen. The master suite has a huge walk-in closet with built-ins plus the master bath has a claw foot tub and separate shower. Close to downtown for dining and shopping. Call today to make an appointment to see this great property.
Save
View Home
$169,900
View Est. Payment
house for sale
4 bds | 2 ba | 1,500 sqft

1010 Twin Ct, Chestertown, MD 21620

Brand new Construction in quiet neighborhood! 4 BR, 2 BA Cape on beautiful lot. Mature trees for privacy on all sides. Stainless steel appliances, soft closing cabinets and nice rear deck for BBQ's overlooking large back yard. Great starter home to expand the family. Extra storage in knee wall attic space! 2x6 Construction. Immediate Occupancy. Builder will help with closing costs.
Save
View Home
$249,900
View Est. Payment
farm for sale
2 bds | 1 ba | 1,582 sqft

8415 Rock Hall Rd, Chestertown, MD 21620

This home is located at 8415 Rock Hall Rd Chestertown, MD 21620 US and has been listed on Homes.com since 6 December 2018 and is currently priced at $895,000, approximately $566 per square foot. This property was built in 1920. 8415 Rock Hall Rd is within the school district(s) Kent County Public Schools with nearby schools including Kent County High School. Similar properties nearby are 9840 White Swan Ct and 6910 Pentridge Ln.
Save
View Home
$895,000
View Est. Payment
house for sale
3 bds | 3 ba | 2,375 sqft

Beacon Hill Classic Villa, Chestertown, MD 21620

This to-be-built home is the "Beacon Hill Classic Villa" plan by Covell Communities, and is located in the community of The Chester River Landing. This plan home is priced from $479,900 and has 3 bedrooms, 2 baths, 1 half baths, is 2,375 square feet, and has a 2-car garage. The Chester River Landing features single family homes by Covell Communities with amenities such as beach, marina, park, pond, pool, trails, views, and waterfrontlots. Listing provided by newhomesource.com.
Save
View Home
$479,900+
View Est. Payment
condominium for sale
4 bds | 4 ba | -- sqft

114 Little Harbor Way #4, Chestertown, MD 21620

Experience true luxury in this magnificent Chestertown waterfront residence. Gleeming hardwood floors, high ceilings and well-appointed architectural detail accent the main level open floor plan outfitted with a great room that includes a grand foyer, formal seating area, and living room, gourmet kitchen, and dining space. The wrap-around porch affords more room for entertaining while the surround sound system adds to the acoustic ambiance. In addition to unobstructed expansive views of the Chester River, the large and ample windows provide an abundance of natural light that tastefully compliments the sophisticated paint scheme enjoyed throughout the home. Take the elevator or the stairs and retreat to the master bedroom suite where you can enjoy a bubble bath in the Jacuzzi tub while watching your favorite program or a nightcap in front of the fireplace or out on the private balcony. * Guests can retreat to the en-suite just down the hall. The third level, which can also be accessed by the elevator, features two bedrooms and a jack & jill bathroom. These rooms currently serve as an art studio and office. * Located in Chester River Landing, one of Kent County's most coveted waterfront communities, homeowners enjoy elite privileges with the peace of mind of having low maintenance, which certainly compliments an enthusiastic and active lifestyle. * 114 Little Harbor Way is one of the few with a deeded boat slip offering 4' mlw, detached garage and private off-street brick parking spaces for 2 vehicles. * NOTICE TO BUYERS: Total Finished Square Feet - 3,406, Property Taxes - $8,051.40 + Town Tax - $2,982.00.
Save
View Home
$850,000
View Est. Payment
house for sale
5 bds | 3 ba | -- sqft

816 S Meadowview Dr, Chestertown, MD 21620

Exhale and enjoy a one level living lifestyle near Downtown Chestertown. With 5 bedrooms total, this home offers all pocket doors and an in-law suite with a handicap accessible master bathroom. The other side of the home sits a master bedroom w/ on-suite and 3 other bedrooms. Freshly painted, move in ready with an updated kitchen with newer stainless steel appliances, granite countertop and a large pantry. The oversized garage allows for small boat storage, ATV's or other fun toys. Bring the outdoors in with two sliders, extending the family room onto the screened porch and back yard.
Save
View Home
$324,000
View Est. Payment
Homes How To

An interactive guide for advice, tips, and tools to buy a home.

Get Started
house for sale
3 bds | 2 ba | 960 sqft

22402 Cross Rd, Chestertown, MD 21620

This house is basically brand new! It has been completely renovated from top to bottom. All new stainless steel appliances, hot water heater, central air/heat, large 16x16 back deck, metal roof, siding, flooring, plumbing, you name it! On almost an acre of land with public water/sewer and a 16x12 shed that has electric. The house is located on a private and quiet street away from all the hustle and bustle of town but still a short drive away.
Save
View Home
$174,500
View Est. Payment
house for sale
4 bds | 4 ba | -- sqft

8020 Airy Hill Rd, Chestertown, MD 21620

Eastern Shore Georgian style home is situated on a serene, rural 10-acres, yet is conveniently located just 2 miles from the colonial town of Chestertown. Designed by the architect, Andrea Lombardini, and built in 2005, the thoughtfully designed interior lends an airy elegance harmoniously linking the sunlit living areas, including the first floor master suite. Taking full advantage of the pastoral views, the home showcases the finest details including random width wood floors, built-ins, high ceilings and a terrace overlooking the naturally beautiful setting. Chestertown offers a river walk, brick lined streets with 18th century homes, galleries, live theater and cafes. It enjoys a vibrant arts community, outdoor educational programs and is home to Washington College. Located about 90-minutes from Washington and Philadelphia.
Save
View Home
$810,000
View Est. Payment
house for sale
4 bds | 3 ba | -- sqft

7250 Pentridge Ln, Chestertown, MD 21620

Rarely do you find a true contemporary residence in this traditional area in Kent County on Maryland's Eastern Shore. This architecturally designed house is surrounded by 168 private acres of open fields, virgin woods & ponds. The 3000+ square footage includes soaring beamed ceilings, open kitchen/living area, wood floors, soap stone counters, gourmet kitchen. An exotic European style "woodstove" (far from your ordinary woodstove - see photos) dominates the outstanding design. Multiple French door & casement windows flow to a 700 sq. ft. deck & 1700 slate A& brick patio. A handsome pergola completes the design of the groundsAn exciting contemporary post & beam guest house shares the acreage and is located a private distance away. The open interior design, exposed beamed ceilings & decking compliments the main house design. Pastoral views and farms abound.
Save
View Home
$1,850,000
View Est. Payment
$19,600
house for sale
2 bds | 1 ba | 1,125 sqft

6262 Quaker Neck Landing Rd, Chestertown, MD 21620

Bring your water toys and enjoy this cute cottage located approximately 1.5 miles from Quaker Neck Landing! Family/dining area combination has wood floors, a wood burning stove and beamed wood ceiling. First floor bedroom has walk-in closet and hookup for stack-able washer/dryer. Upstairs has a 2nd bedroom and currently used as "the Bunk Room" . The grounds have been well landscaped and there is even an outdoor shower! Use as a retreat, primary home, hunting cabin/cottage, etc. Not too far from Historic downtown Chestertown!!
Save
View Home
$159,900
View Est. Payment
$12,150
house for sale
4 bds | 3 ba | -- sqft

933 Round Top Rd, Chestertown, MD 21620

Wow, wow; is this ever a beautiful "home" with so much to enjoy - designed just for you! Every room has something special to offer: living room with recessed lighting displays a 7' bow window 2' sill and a lovely fireplace, opens to dining room with French doors leading to 24 x 12 brick patio; kitchen proudly displays a large island that can seat six, new Bosch dishwasher, two wall ovens, new SS fridge, gorgeous maple cabinets & more; extra-wide 48" staircase leads to upstairs bedrooms and washer/dryer making laundry day a breeze; beautiful large master BR with 2 walk-in closets, double sinks in large bath; each bedroom has own thermostat; Family room with fireplace opens to family-style screened-in porch complete with ceiling fan; ~2 y/o dual heat pumps, one for each level; full basement with fireplace; 2-car side-entrance attached garage; front porch with swing; lovely fencing in front and most of back yard also fenced. Storage/garden shed; lovely landscaping to display lots of colorful plantings. Round Top Park is one block away and offers tennis courts, playground, ball field, etc. This amazing home has so much to offer you -- you must see it for yourself to fully appreciate all it has for YOU!
Save
View Home
$307,750
View Est. Payment
house for sale
3 bds | 3 ba | 2,500 sqft

7955 Airy Hill Road, Chestertown, MD 21620

A country treasure located just outside of Chestertown on 6 open acres with views of 4 acre waterfowl pond. Spacious home with lots of desirable features. Room for animals, hobby crops, a pool, or whatever you want. Recent roof replacement and brand new well. Metal shop building with tractor shed attached. The possibilities are endless!
Save
View Home
$585,000
View Est. Payment
house for sale
2 bds | 1 ba | 1,582 sqft

8415 Rock Hall Rd Rd, Chestertown, MD 21620

166 +/- total acre farm with 66 tillable acres, 75 wooded acres and the remaining in home site, barns, and active gravel pit. The farm offers excellent deer, turkey and waterfowl hunting and has several potential pond sites. Located near Remington Farms and approximately 10 minutes between Rock Hall and Chestertown, this farm is priced to sell at $5,391 an acre! Property lines in aerial photo are approximate.
Save
View Home
$895,000
View Est. Payment
house for sale
3 bds | 2 ba | -- sqft

5564 Quaker Neck Landing Rd, Chestertown, MD 21620

This one is a must see!! This charming restored farmhouse located steps away from Quaker Neck Landing has something for everyone whether your your looking for a family getaway or a full time residence. The home offers an upgraded cooks kitchen, bathrooms, new screened in porch, stone patio with fire pit, original hardwood floors, off street parking with carport, and barn for storage with workshop area. Call to schedule your showing today.
Save
View Home
$359,900
View Est. Payment
house for sale
3 bds | 2 ba | 1,867 sqft

229 Princess Anne Dr, Chestertown, MD 21620

Move-in ready home in Queen Anne's County, but just a few minutes from Downtown Chestertown! Offering new carpets, paint and landscaping. Desirable split bedroom, single level living floor plan. Large Master suite offers walk in closet and great Master bath with tiled floors, double vanity, separate shower and corner soaking tub! Two additional bedrooms share a full bath with tiled floors. Large kitchen/breakfast area with stone tile floors and wood cabinets opens to screened porch. Open family room with propane fireplace for chilly Fall nights. Separate formal dining room or office space. Oversize 2-car garage and a fully fenced rear yard round out the total package.
Save
View Home
$285,000
View Est. Payment
house for sale
6 bds | 6 ba | -- sqft

24091 Providence Plantation Ln, Chestertown, MD 21620

A quintessential 76-acre Eastern Shore waterfront estate built in 1781 & restored in the 90's. Providence Plantation defines Country Elegance with a fabulous 1st floor master bedroom suite, a new 3 BR Tenant House, dock with lift and an in-ground pool. A 3rd home may be built to create a family compound. Enjoy the peace and serenity of the Eastern Shore outdoor life. Owner is Licensed Real Estate Agent.
Save
View Home
$2,999,500
View Est. Payment
$13,767
house for sale
3 bds | 3 ba | 1,722 sqft

304 Princess Anne Dr, Chestertown, MD 21620

Property is being sold "AS IS" with buyer inspections for informational purposes only. Well proportioned colonial at the end of street location in established neighborhood, just across the river from Chestertown. Private backyard is bordered by evergreens and natural ravine. Septic has been updated. With some remodeling this could be a lovely home providing years of enjoyment for its next owners.
Save
View Home
$169,900
View Est. Payment
house for sale
4 bds | 3 ba | -- sqft

108 S Mill St, Chestertown, MD 21620

Iconic Mill Street home, this "Folk Victorian" has been lovingly maintained & thoughtfully upgraded while maintaining the historic features: refinished Heart Pine flooring throughout, crown moulding, chair rails, built-in shelving, & an extra-long claw foot soaking tub . Upgrades include high-velocity HVAC, blown-in insulation (walls, attic, & cellar), granite counters & new cabinetry in the kitchen, tiled bathrooms, dressing room off the Master bedroom with a walk-in closet, & encapsulated cellar. The backyard oasis is private, quiet, & low-maintenance; seasonal trees & plants bloom three seasons of the year. The garden shed & shop is tucked away, but offers great storage & work space. Situated in the heart of Downtown Chestertown, take a peek at this home soon!
Save
View Home
$365,000
View Est. Payment
house for sale
3 bds | 2 ba | -- sqft

10090 Forrest Ln, Chestertown, MD 21620

Eastern Shore waterfront post and beam home is sited on 6.5 acres in a serene, wooded setting with water views. Located in Great Oak Estates with golf course and pool privileges for $60 annual fee and boat dock for additional fee. New Hardiplank siding, architectural shingle roof and Trex deck. Open design with 1st floor master bedroom. 15-minutes from Historic Chestertown and Washington College.
Save
View Home
$547,000
View Est. Payment

Location data not available
loading