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1635 Winchester Road, Annapolis, MD 21409

$1,139,400
  • 1635 Winchester Road, Annapolis, MD 21409 Main Photo

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Pending
BEDS5 BATHS4 full SQUARE FEET3,660 MLS#MDAA2130382
STATUSPENDING PROPERTY TYPEResidential - Single Family SUBDIVISIONWINCHESTER ESTATES SCHOOLANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Property Description

A Rare Exceptional Retreat in Winchester Estates — Annapolis, MD Welcome to an extraordinary custom-built residence where timeless elegance meets unparalleled serenity. Set on a magnificently landscaped, park-like acre, this 5-bedroom, 4-bath estate offers a level of privacy and tranquility seldom found so close to the heart of downtown Annapolis. Nestled within the prestigious Winchester Estates, this property grants private water-access creating a lifestyle that blends luxury living with the best Annapolis has to offer. Inside, unique design and exceptional craftsmanship define every space. The chef’s kitchen, outfitted for the culinary enthusiast, anchors the main level and opens seamlessly to a grand, light-filled living area—an ideal setting for refined entertaining or intimate gatherings. Expansive windows invite the lush landscape indoors, enhancing the home’s natural harmony and sense of calm. The elegant lower level offers a rare level of versatility, featuring a full private suite with its own bedroom, bathroom, kitchen, dining room, and living room—perfect for multigenerational living, distinguished guest accommodations, or an au pair residence. Outside, the estate’s grounds unfold like a private sanctuary. Mature trees, newly developing gardens, and verdant open spaces create an atmosphere of effortless peace—a truly restorative environment just minutes from world-class dining, boutique shopping, and the historic charm of Annapolis. Highlights Include: * Custom-built architecture on a serene 1+ acre park-like lot * Extensive cutting-edge electronic pet fence system * Exclusive neighborhood water-access privileges * Right next door to the beautiful Baltimore Annapolis Trail Park * Gourmet chef’s kitchen with Blue Star 8 Burner Stove and expansive entertaining areas * Full private lower-level suite with separate living quarters * A Total of Five spacious bedrooms and four well-appointed bathrooms * Two upper level bedrooms have self-contained climate control * Exceptional privacy in one of Annapolis’ most coveted communities * Full Premium Warranty Offered This is more than a home—it is a private retreat offering refined luxury, natural beauty, and an unmatched Annapolis lifestyle.

1635 Winchester Road | MLS# MDAA2130382

This single family home located at 1635 Winchester Road, Annapolis, MD 21409 is currently listed for sale with an asking price of $1,139,400. This property was built in 1959 and has 5 bedrooms and 4 full baths with 3660 sq. ft. Winchester Road is located in the WINCHESTER ESTATES subdivision within the ANNE ARUNDEL COUNTY PUBLIC SCHOOLS school district. Search WINCHESTER ESTATES real estate on www.realestatelancastercounty.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Fully Finished, Walkout Level, Other, Space For Rooms, Side Entrance, Outside Entrance, Interior Access, Improved, Heated, Garage Access, Full, Daylight, Full, Connecting Stairway
Cooling: Central A/C, Ductless/Mini-Split
Fireplaces: 2
Fuel Type: Central, Natural Gas
Garage: 2
Heating: Forced Air, Humidifier, Zoned
Home Style: Traditional
Lot Size: 1.06 Acres
Roof Type: Asphalt
Stories: 3.0
Taxes: $6,942
Year Built: 1959

Feature Descriptions

Accessibility: Doors - Lever Handle(s), Doors - Swing In
Additional Structures: Above Grade, Below Grade
Appliances: Washer/Dryer Hookups Only, Disposal, Dryer, Exhaust Fan, Extra Refrigerator/Freezer, Humidifier, Microwave, Oven - Self Cleaning, Oven/Range - Electric, Washer/Dryer Stacked
Exterior: Brick, Combination, Fiber Cement, Masonry, Shake Sidin
Exterior: Sidewalks, Gutter System, Secure Storage, Street Lights
Fireplace: Fireplace - Glass Doors, Mantel(s), Screen
Interior: Attic,2nd Kitchen, Kitchen - Efficiency, Family Room Off Kitchen, Breakfast Area, Dining Area, Built-Ins, Chair Railings, Crown Moldings, Primary Bath(s), Wood Floors, Floor Plan - Traditional
Lake Name: COOL SPRING COVE
Lot: Backs to Trees, Landscaping, Adjoins - Public Land, Backs - Parkland, Private, Rear Yard, Trees/Wooded
Lot Dimensions: 1.06 Acre(S)
Parking Notes: 2 Total Parking Spaces
Pet Restrictions: No Pet Restrictions
Sewer: On Site Septic
Special View Info: Garden/Lawn, Trees/Woods, Park/Greenbelt
SQFT Above Finished: 2441
SQFT Below Finished: 1219
SQFT Total Finished: 3660
Structure Type: Detached
Total Garage/Parking Spaces: 2
Utilities: Cable TV Available, Electric Available, Natural Gas Available, Phone Available, Water Available
Water: Public
Water Access: Private Access
Windows: Bay/Bow, Screens, Storm, Wood Frame
Wooded: Yes

Local Schools

High School: BROADNECK
Middle School: SEVERN RIVER
Elementary School: ARNOLD
School District: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Equity Property Investments
Agency Phone: 9193600430

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Estimated Payment

$ 3,446.64 per month $2,535.81 Principal & Interest $578.50 Property Tax $332.33 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 03/07/2026. The listing information on this page last changed on 03/07/2026. 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 Sat 03/07/2026 12:02:59 AM EST) or Bright MLS (last updated Fri 03/06/2026 11:57:57 PM 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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