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1635 Winchester Rd, Annapolis, MD 21409
1635 Winchester Rd, Annapolis, MD 21409
1635 Winchester Rd, Annapolis, MD 21409
1635 Winchester Rd, Annapolis, MD 21409
1635 Winchester Rd, Annapolis, MD 21409
1635 Winchester Rd, Annapolis, MD 21409
1635 Winchester Rd, Annapolis, MD 21409

1635 Winchester Rd Annapolis, MD 21409

$1,139,400

ACTIVE UNDER CONTRACT
Beds
5
Baths
4
Sqft
3,660
Acres
1.06
Year
1959
Days on Site
6
Property Type
Residential
Sub Type
Per Square Foot
$311
Date Listed
Feb 13, 2026

Description of 1635 Winchester Rd, Annapolis, MD 21409

Listing details for 1635 Winchester Rd, Annapolis, MD 21409 : 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.
Listing Updated : 02-17-2026 at 08:52 AM EST

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Home Details
1635 Winchester Rd, Annapolis, MD 21409
Status
Active Under Contract
MLS #ID
MDAA2130382
Price
$1,139,400
Bedrooms
5
Bathrooms
4
Square Footage
3,660
Acres
1.06
Year
1959
Days on Site
6
Property Type
Residential
Property Sub Type
Price per Sq Ft
$311
Date Listed
Feb 13, 2026
Community Information for 1635 Winchester Rd, Annapolis, MD 21409
Address
1635 Winchester Rd
State
Maryland
Zip Code 21409
Schools
Utilities
Sewer
On Site Septic
Water Source
Public
Interior
Interior Features
Attic, 2nd Kitchen, Kitchen - Efficiency, Family Room Off Kitchen, Breakfast Area, Dining Area, Built-Ins, Chair Railings, Crown Moldings, Primary Bath(s), Wood Floors and Floor Plan - Traditional
Appliances
Washer/Dryer Hookups Only, Disposal, Dryer, Exhaust Fan, Extra Refrigerator/Freezer, Humidifier, Microwave, Oven - Self Cleaning, Oven/Range - Electric and Washer/Dryer Stacked
Heating
Forced Air, Humidifier and Zoned
Cooling
Central A/C and Ductless/Mini-Split
Fireplace
Yes
# of Fireplaces
2
Exterior
Exterior
Sidewalks, Gutter System, Secure Storage and Street Lights
Roof
Asphalt
Garage Spaces
2
Foundation
Block
HOA
Has HOA
None
Additional Information
Styles
Traditional
Price per Sq Ft
$311
Listing Provided By

Ana L Lopez, 9193600430, [email protected], Equity Property Investments

Source

Bright MLS, MLS#: MDAA2130382

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This beautiful 5 beds 4 baths home is located at 1635 Winchester Rd, Annapolis, MD 21409 and is listed for sale at $1,139,400.00. This home was built in 1959, contains 3660 square feet of living space, and sits on a 1.06 acre lot. This residential home is priced at $311.31 per square foot.

If you'd like to request a tour or more information on 1635 Winchester Rd, Annapolis, MD 21409, please call us at (202) 441-2348 so that we can assist you in your real estate search. To find homes like 1635 Winchester Rd, Annapolis, MD 21409, you can search homes for sale in Annapolis , or visit the neighborhood of Winchester Estates , or by 21409 . We are here to help when you're ready to contact us!

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Home Details
1635 Winchester Rd, Annapolis, MD 21409
Status
Active Under Contract
MLS #ID
MDAA2130382
Price
$1,139,400
Bedrooms
5
Bathrooms
4
Square Footage
3,660
Acres
1.06
Year
1959
Days on Site
6
Property Type
Residential
Property Sub Type
Price per Sq Ft
$311
Date Listed
Feb 13, 2026
Community Information for 1635 Winchester Rd, Annapolis, MD 21409
Address
1635 Winchester Rd
State
Maryland
Zip Code 21409
Schools
Utilities
Sewer
On Site Septic
Water Source
Public
Interior
Interior Features
Attic, 2nd Kitchen, Kitchen - Efficiency, Family Room Off Kitchen, Breakfast Area, Dining Area, Built-Ins, Chair Railings, Crown Moldings, Primary Bath(s) and Wood Floors
Appliances
Washer/Dryer Hookups Only, Disposal, Dryer, Exhaust Fan, Extra Refrigerator/Freezer, Humidifier, Microwave, Oven - Self Cleaning and Oven/Range - Electric
Heating
Forced Air and Humidifier
Cooling
Central A/C and Ductless/Mini-Split
Fireplace
Yes
# of Fireplaces
2
Exterior
Exterior
Sidewalks, Gutter System and Secure Storage
Roof
Asphalt
Garage Spaces
2
Foundation
Block
HOA
Has HOA
None
Additional Information
Styles
Traditional
Price per Sq Ft
$311
Listing Provided By

Ana L Lopez, 9193600430, [email protected], Equity Property Investments

Source

Bright MLS, MLS#: MDAA2130382

Comments

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Data last updated: February 5, 2026 6:11 AM UTC

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Some properties that appear for sale on this website may no longer be available because they are under contract, have Been Sold, or are no longer being offered for sale.  Some real estate firms do not participate in IDX, and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the seller's request.