1635 WINCHESTER RD Annapolis, MD 21409 Price Dropped by $108K

UPDATED: 12/02/2025 03:46 AM ON MARKET: 27 days on market

$1,139,400

5 Beds4 Baths3,660 SqFt

Key Details

Property Type Single Family Home

Sub Type Detached

Listing Status Active

Purchase Type For Sale

Square Footage 3,660 sqft

Price per Sqft $311

Subdivision Winchester Estates

MLS Listing ID MDAA2130382

Style Traditional

Bedrooms 5

Full Baths 4

HOA Y/N N

Abv Grd Liv Area 2,441

Year Built 1959

Available Date 2025-11-08

Annual Tax Amount $6,942

Tax Year 2025

Lot Size 1.060 Acres

Acres 1.06

Property Sub-Type Detached

Source BRIGHT

Property Description

“A rare price improvement now makes this park-like, 1+ acre estate an even more exceptional opportunity. Discover the privacy, beauty, and craftsmanship of this custom home before it quietly slips off the market.”

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.