$1,247,900

1635 Winchester Rd, Annapolis, MD, 21409

5

Beds

4

Baths

3,660

Square feet

1.06

Acres

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 * 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.

Listing Details

OfficeEquity Property Investments
Contact Info9193600430

Facts & Features

MLS® # MDAA2130382
Price $1,247,900
Bedrooms 5
Bathrooms 4.00
Full Baths 4
Square Footage 3,660
Acres 1.06
Year Built 1959
Type Residential
Sub-Type Detached
Style Traditional
Status Active

Community Information

Address 1635 Winchester Rd
Subdivision WINCHESTER ESTATES
City Annapolis
County ANNE ARUNDEL-MD
State MD
Zip Code 21409
Senior Community No

Amenities

Amenities Attic, Built-Ins, Chair Railing, Crown Molding, Master Bath(s), Wood Floors, Washer/Dryer Hookup
Utilities Cable TV Available, Electric Available, Natural Gas Available, Phone Available, Water Available
# of Garages 2
Garages Garage - Side Entry
View Garden/Lawn, Trees/Woods, Park/Greenbelt
Is Waterfront No

Interior

Interior Features Floor Plan-Traditional
Appliances Disposal, Dryer, Exhaust Fan, Extra Refrg/Frz, Humidifier, Microwave, Oven-Self Cleaning, Oven/Range-Electric, Washer/Dryer Stacked
Heating Forced Air, Humidifier, Zoned
Cooling Central A/C, Ductless/Mini-Split
Has 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
Fireplace Yes
# of Fireplaces 2
Fireplaces Fireplace - Glass Doors, Mantel(s), Screen
# of Stories 3
Stories 3

Exterior

Exterior Brick and Siding, Combination, Fiber Cement Siding, Shake, Wood
Exterior Features Sidewalks, Gutter System, Secure Storage, Street Lights, Patio, Porch-screened
Lot Description Backs to Trees, Landscaping, Adjoins - Public Land, Bcks-Prklnd, Private, Rear Yard, Trees/Wooded
Windows Bay/Bow, Screens, Storm, Wood Frame
Roof Asphalt
Foundation Block
Other Structures Garage(s), Shed

School Information

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

Additional Information

Date Listed November 8th, 2025
Days on Market 11
Zoning R1
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Map

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