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Andrew Undem
REALTOR®
(410) 322-3670
Office: (410) 814-2400
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136 Hilltop Drive, Chestertown, MD 21620

$366,000
  • 136 Hilltop Drive, Chestertown, MD 21620 Main Photo

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Contingent
BEDS3 BATHS2 full SQUARE FEET1,432 MLS#MDQA2016782
STATUSACTIVE UNDER CONTRACT PROPERTY TYPEResidential - Single Family SUBDIVISIONTHE FLYWAY SCHOOLQUEEN ANNES COUNTY PUBLIC SCHOOLS

Property Description

Immaculate 3-bedroom, 2-bath home set on a breathtaking, oversized lot with exquisite mature landscaping and a truly picturesque setting. Surrounded by lush greenery and stunning trees, including a graceful willow, this property offers a serene, park-like atmosphere, with views from nearly every window resembling beautiful landscape artwork. Inside, the home features a bright, open floor plan designed for modern living. A spacious family room flows seamlessly into the generous kitchen, while a separate dining room remains open to the main living areas—perfect for everyday living and entertaining. The kitchen is highlighted by beautiful French doors leading to the back patio, offering easy access for cooking, grilling, and hosting—perfect for summer barbecues and outdoor entertaining. Palladium windows throughout enhance the home with natural light and showcase the spectacular views. The thoughtfully designed layout offers a private primary suite on one side of the home with its own attached bath. Just off the kitchen and near the primary bedroom is a separate laundry room for added convenience. Two additional bedrooms are situated on the opposite side and share a well-appointed full hall bath. Additional features include fresh paint throughout, a side-entry one-car garage, and an extra-large driveway providing ample off-street parking. Tucked away on a quiet cul-de-sac with no through traffic, this home offers a rare combination of privacy, beauty, and tranquility.

136 Hilltop Drive | MLS# MDQA2016782

This single family home located at 136 Hilltop Drive, Chestertown, MD 21620 is currently listed for sale with an asking price of $366,000. This property was built in 1995 and has 3 bedrooms and 2 full baths with 1432 sq. ft. Hilltop Drive is located in the THE FLYWAY subdivision within the QUEEN ANNES COUNTY PUBLIC SCHOOLS school district. Search THE FLYWAY real estate on andrewundem.homesale.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Ceiling Fan(s)
Fuel Type: Electric
Garage: 1
Heating: Heat Pump(s)
Home Style: Ranch/Rambler
Lot Size: 1.01 Acres
Roof Type: Architectural Shingle
Stories: 1.0
Taxes: $2,532
Year Built: 1995

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Dryer, Washer, Dishwasher, Exhaust Fan, Refrigerator, Stove, Water Conditioner - Owned, Water Heater
Exterior: Extensive Hardscape, Exterior Lighting, Gutter System
Exterior: Vinyl Siding
Flooring: Ceramic Tile, Laminated, Partially Carpeted
Interior: Ceiling Fan(s), Bathroom - Tub Shower, Carpet, Combination Dining/Living, Combination Kitchen/Dining, Combination Kitchen/Living, Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Open, Kitchen - Table Space
Lot: Cul-de-sac, Front Yard, Landscaping, No Thru Street, Rear Yard, SideYard(s)
Lot Dimensions: 1.01 Acre(S)
Parking Features: Asphalt Driveway
Parking Notes: 5 Total Parking Spaces
Rooms: Living Room, Dining Room, Primary Bedroom, Bedroom 2,Bedroom 3,Kitchen
Sewer: Septic Exists, Septic Pump
Special View Info: Garden/Lawn
SQFT Above Finished: 1432
SQFT Total Finished: 1432
Structure Type: Detached
Total Garage/Parking Spaces: 5
Water: Well
Windows: Double Hung, Double Pane, Palladian, Screens

Room Sizes

Dining Room: 12 x 12 Level - Main
Living Room: 21 x 17 Level - Main
Kitchen: 16 x 12 Level - Main
Primary Bedroom: 19 x 11 Level - Main
Bedroom 2: 11 x 10 Level - Main
Bedroom 3: 11 x 11 Level - Main

Local Schools

School District: QUEEN ANNES COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Northrop Realty
Agency Phone: 4102956579

Shown By

Agent Name: Andrew Undem
Agent Phone: (410) 322-3670
Agency Title: Berkshire Hathaway HomeServices Homesale Realty

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Estimated Payment

$ 1,132.31 per month $814.56 Principal & Interest $211.00 Property Tax $106.75 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/23/2026. The listing information on this page last changed on 04/23/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 04/23/2026 2:25:08 AM EST) or Bright MLS (last updated Thu 04/23/2026 12:38:38 AM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Agent License Information: 
Licensed in Maryland
Andrew Undem 

3500 Boston Street, Baltimore, MD 21224
410-814-2400

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