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21146 Montana Ave, 
Chestertown, MD 21620

$289,900


2

Beds


2

Baths


1,500

Sq Ft


Single Family

Pending

Listed by

Jody Baker

Cross Street Realtors LLC., 4434803453, stacy@csrealtors.com

Last updated:

August 16, 2026, 08:09 AM

MLS#

MDKE2006858

Source:

BRIGHTMLS

About This Home

21146 Montana Ave

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.

Home Facts

Single Family

2 Baths

2 Bedrooms

Built in 1990

Subdivision & Development:

TOLCHESTER ESTATES

Price Summary

289,900

$193 per Sq. Ft.

MLS #:

MDKE2006858

Last Updated:

August 16, 2026, 08:09 AM

Added:

19 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

2

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

1

Interior

Living Area:

1,500 Sq. Ft.


Structure

Structure

Architectural Style:

A-Frame, Cabin/Lodge

Building Area:

1,500 Sq. Ft.

Year Built:

1990


Lot

Lot Size (Sq. Ft):

17,859


Finances & Disclosures

Finances

Price:

$289,900

Price per Sq. Ft:

$193 per Sq. Ft.

Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bright Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.