Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom, home office, or additional living space. The welcoming living room and eat-in kitchen both feature sliding glass doors that open to the side deck, creating a wonderful space for entertaining or simply relaxing while enjoying the peaceful surroundings. The kitchen offers vinyl plank flooring, oak cabinetry, an electric range, built-in microwave, dishwasher, and plenty of space for casual dining. The primary bedroom includes two closets and a private half bath, while the second bedroom features convenient washer and dryer hookups. Upstairs, the spacious loft boasts beautiful wood flooring and access to a second-story deck overlooking the wooded backyard. Stay comfortable year-round with central air conditioning, electric baseboard heat, and the cozy warmth of a wood stove that serves as an excellent supplemental heat source during the cooler months. Additional updates include a newer central A/C system (approximately 6 years old), a new water heater, and a new water softener. Need extra space for hobbies, storage, or projects? The detached 20' x 24' outbuilding with electricity, wood flooring, and a garage door offers endless possibilities as a workshop, studio, or storage for your outdoor gear. Enjoy everything Tolchester Estates has to offer, including exclusive resident access to a private community beach and boat ramp. Just a short walk or golf cart ride away, you'll also find Tolchester Marina and The Shanty Beach Bar, where you can enjoy waterfront dining, live music, boating, and breathtaking Chesapeake Bay sunsets. Whether you're searching for a full-time residence, weekend getaway, or vacation home, this property offers an incredible opportunity to enjoy the Chesapeake Bay lifestyle while adding your own personal touches. Being sold as-is.
For sale
$289,900
21146 Montana Ave, Chestertown, MD 21620
2beds
1,500sqft
:
Get pre-qualified$1,921/mo
Single Family Residence
Built in 1990
0.41 Acres Lot
$283,900 Zestimate®
$193/sqft
$-- HOA
What's special
Spacious loftCentral air conditioningSide deckMature treesElectric baseboard heatElectric rangeOak cabinetry
- 11 days |
- 1,542 |
- 159 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Jody Baker 410-708-3536,
Cross Street Realtors LLC 4434803453
Source: Bright MLS,MLS#: MDKE2006858
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
- Main level bathrooms: 2
- Main level bedrooms: 2
Basement
- Area: 0
Heating
- Baseboard, Wood Stove, Electric, Wood
Cooling
- Central Air, Electric
Appliances
- Included: Microwave, Dishwasher, Oven/Range - Electric, Water Conditioner - Owned, Water Heater, Water Treat System, Electric Water Heater
- Laundry: Hookup, Main Level, Washer/Dryer Hookups Only
Features
- Bathroom - Tub Shower, Combination Kitchen/Dining, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Traditional, Kitchen - Country, Dry Wall
- Flooring: Carpet, Laminate, Vinyl, Wood
- Has basement: No
- Number of fireplaces: 1
- Fireplace features: Brick, Wood Burning, Wood Burning Stove
Interior area
- Total structure area: 1,500
- Total interior livable area: 1,500 sqft
- Finished area above ground: 1,500
- Finished area below ground: 0
Property
Parking
- Total spaces: 5
- Parking features: Storage, Gravel, Detached, Driveway, Off Street
- Garage spaces: 1
- Uncovered spaces: 4
- Details: Garage Sqft: 480
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Patio & porch: Deck
- Pool features: None
- Waterfront features: Bay
- Body of water: Chesapeake Bay
Lot
- Size: 0.41 Acres
- Features: Front Yard, Wooded, Rear Yard
Details
- Additional structures: Above Grade, Below Grade, Outbuilding
- Parcel number: 1506009735
- Zoning: CAR
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: A-Frame,Cabin/Lodge
- Property subtype: Single Family Residence
Materials
- Frame, Wood Siding
- Foundation: Crawl Space
Condition
- New construction: No
- Year built: 1990
Utilities & green energy
- Sewer: Public Sewer
- Water: Well
Community & HOA
Community
- Subdivision: Tolchester Estates
HOA
- Has HOA: No
Location
- Region: Chestertown
Financial & listing details
- Price per square foot: $193/sqft
- Tax assessed value: $167,500
- Annual tax amount: $1,813
- Date on market: 7/28/2026
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional,FHA,USDA Loan,VA Loan
- Exclusions: Vintage Rakes
- Ownership: Fee Simple
Estimated market value
$283,900
$270,000 - $298,000
$1,648/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/28/2026 | Listed for sale | $289,900+367.6%$193/sqft |
Source:  Bright MLS #MDKE2006858 Report a problem | ||
| 6/13/1994 | Sold | $62,000$41/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $3,627 +110% | $159,900 +5% |
| 2024 | $1,727 +0.8% | $152,300 +0.8% |
| 2023 | $1,713 +1.7% | $151,100 -0.8% |
| 2022 | $1,685 -0.1% | $152,300 +2.4% |
| 2021 | $1,686 +0.8% | $148,700 +0.8% |
| 2020 | $1,672 +0.8% | $147,467 -0.8% |
| 2019 | $1,658 +0.9% | $148,700 +2.6% |
| 2018 | $1,644 | $145,000 |
| 2017 | $1,644 -8.4% | $145,000 |
| 2016 | $1,795 | $145,000 -1.2% |
| 2015 | $1,795 | $146,800 |
| 2014 | $1,795 | $146,800 |
| 2013 | -- | $146,800 -7.3% |
| 2012 | -- | $158,300 |
| 2011 | -- | $158,300 |
| 2010 | -- | $158,300 -7.6% |
| 2009 | -- | $171,340 +18.3% |
| 2008 | -- | $144,832 +22.4% |
| 2007 | -- | $118,326 +28.9% |
| 2006 | -- | $91,820 +4.7% |
| 2005 | -- | $87,666 +5% |
| 2004 | -- | $83,513 +5.2% |
| 2003 | -- | $79,360 +0.9% |
| 2002 | -- | $78,640 +0.9% |
| 2001 | -- | $77,920 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 21620
Nearby schools
GreatSchools rating
- 5/10Rock Hall Elementary SchoolGrades: PK-5Distance: 5.8 mi
- 2/10Kent County Middle SchoolGrades: 6-8Distance: 9.5 mi
- 5/10Kent County High SchoolGrades: 9-12Distance: 9.1 mi
Schools provided by the listing agent
- District: Kent County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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A local agent can set up tours, give advice and negotiate with sellers.
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