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1635 Winchester Rd, 
Annapolis, MD 21409

$1,247,900


5

Beds


4

Baths


3,660

Sq Ft


Single Family

Coming Soon

Listed by

Ana L Lopez

Equity Property Investments

Last updated:

November 5, 2025, 12:08 PM

MLS#

MDAA2130382

Source:

BRIGHTMLS

About This Home

1635 Winchester Rd

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 This is more than a home—it is a private retreat offering refined luxury, natural beauty, and an unmatched Annapolis lifestyle. (Additional pictures coming soon).

Home Facts

Single Family

4 Baths

5 Bedrooms

Built in 1959

Price Summary

1,247,900

$340 per Sq. Ft.

MLS #:

MDAA2130382

Last Updated:

November 5, 2025, 12:08 PM

Added:

3 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

4

Interior

Living Area:

3,660 Sq. Ft.


Structure

Structure

Architectural Style:

Traditional

Building Area:

3,660 Sq. Ft.

Year Built:

1959


Lot

Lot Size (Sq. Ft):

46,173


Finances & Disclosures

Finances

Price:

$1,247,900

Price per Sq. Ft:

$340 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. © 2025 Bright Mls All rights reserved.
See this home in person
1635 Winchester Rd
Attend an upcoming open house
Sat, Nov 8
10:30 AM04:00 PM

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