New51
$525,000
3 bd · 3 ba · 1,833 sqft
8901 S Bayview Dr, Chestertown, MD
Grace M Crockett · Doug Ashley Realtors, LLC
School ratings (A+ to F) from HJN community data.
Kent County Middle School
6-8 · Regular · Kent County Public Schools
354 students · 10.4:1 student–teacher
Chestertown Christian Academy
PK-12 · Regular
193 students · 11.0:1 student–teacher
Henry Highland Garnet Elementary School
PK-5 · Regular · Kent County Public Schools
322 students · 11.9:1 student–teacher
Radcliffe Creek School
KG-8 · Regular
73 students · 4.6:1 student–teacher
Kent School
PK-8 · Regular
127 students · 7.3:1 student–teacher
Friendship Montessori School
PK-KG · Montessori
6 students · 2.1:1 student–teacher
Bright MLSThis content last refreshed on 2026-10-17 02:52:44 UTC. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
New51
$525,000
3 bd · 3 ba · 1,833 sqft
8901 S Bayview Dr, Chestertown, MD
Grace M Crockett · Doug Ashley Realtors, LLC
142$568,900
4 bd · 3 ba · 2,464 sqft
329 Union Church Rd, Chestertown, MD
Heather Dolan · Chesapeake Real Estate Associates, LLC
Price Reduced92$829,000
3 bd · 4 ba · 2,472 sqft
106 Queen St S, Chestertown, MD
Maryn J. LeClair · Chesapeake Real Estate Associates, LLC
46$685,000
3 bd · 3 ba · 3,000 sqft
117 Water St N #1a, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
31$898,000
3 bd · 4 ba · 2,172 sqft
226 S Water St, Chestertown, MD
John J Burke · Gunther-McClary Real Estate
26$786,900
3 bd · 3 ba · 1,964 sqft
#35 Landing Ln, Chestertown, MD
Julia Hilfiker · Gunther-McClary Real Estate





Rings at ½ mile and 1 mile. Basemap © OpenMapTiles © OpenStreetMap contributors.
Open the Chestertown camera map1 speed camera mapped within 1 mile of this home. None within ½ mile. Nearest: 0.7 mi northwest.
| Device type | Within ½ mi | Within 1 mi |
|---|---|---|
| Speed cameras | 0 | 1 |
Community-reported via OpenStreetMap; may be incomplete. Data as of . © OpenStreetMap contributors (ODbL)
Speed cameras photograph vehicles over the speed limit for automated tickets.
Within 2 miles of this home: 11 restaurants and cafés, 1 grocery store, 17 parks and green spaces, and 7 transit stops.
Place data from OpenStreetMap.
Phat Daddy’s BBQ Shack
Spring Avenue
Dunkin' Donuts
High Street
Domino's
Washington Avenue
Procolino's Pizza (Proc’s)
Washington Avenue
Arby's
Washington Avenue
KFC
Washington Avenue
Dunkin
Washington Avenue
The Freeze
Washington Avenue
Acme
Washington Avenue
Rolling Road Park
Chestertown Dog Park
Schauber Road
Rubber JungleGym
Church Playground
Chestertown Historic District
Fountain Park
High Street
Chestertown Historical Monuments
Kings Town Park
Chestertown Hospital
Dollar General
Kent County Social Services Department
Southern States
Kingstown Apartments
Tractor Supply Co
Redner's Markets
Est. $4,958/mo$345/sqft · 101 days on Realty
3
Beds
3
Baths
2,176
Sqft
1994
Built
Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A freshly sealed asphalt drive curves to a welcoming front entry, where a classic brick facade sets a warm, distinctive tone. A two-car attached garage provides direct entry and everyday convenience. * Inside, the open kitchen—complete with breakfast area—flows seamlessly into a spacious family room, perfect for everyday living. A separate dining room makes entertaining easy. The family room is an elegant space for gatherings, while a dedicated sunroom and screened-in porch invite you to enjoy the serene, park-like backyard in every season. The large deck offers an additional outdoor retreat with tranquil wooded views. * The generous primary suite features an en-suite bath, while two additional bedrooms makes for flexible bedroom accommodations for family, guests, or a quiet work-from-home office space. A convenient half bath and main-floor laundry round out the practical layout. A full basement offers abundant storage and endless potential for an artist’s studio, workshop, recreation room, or finished expansion. * With its pristine landscaping, mature plantings, and verdant views, this exceptional home is a rare find. And the location is second to none—just minutes from historic downtown Chestertown. Stroll tree-lined streets to discover specialty shops, art galleries, restaurants, and the Saturday Farmers Market at Fountain Park. Washington College, the nation’s tenth-oldest college, anchors the community with year-round cultural events, lectures, and performances. Outdoor enthusiasts will love the nearby Rail Trail, Sultana Lawrence Wetlands Preserve, marinas, and public boat launches providing easy access to the Chester River and Chesapeake Bay. First Friday celebrations, waterfront festivals, and a vibrant arts scene make Chestertown one of the Eastern Shore’s most beloved places to call home.
Listing agent
Liddy Campbell
Courtesy of TTR Sotheby's International Realty
(410) 708-5433
Bright MLS · Listing MDKE2006896
$150,000
Estimated monthly payment
$4,958/mo
Loan amount $600,000. Estimate only — your actual rate and payment depend on credit, location, and lender.
2026 roll