1635 Winchester Road Annapolis, MD $ 1,139,400
1635 Winchester Road
$ 1,139,400
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1635 Winchester Road

Annapolis, MD, 21409
$ 1,139,400
Bedrooms5 Baths4.0 Sq 3,660

Monthly Estimate*

$ 7,108

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Single Family Home for sale in Annapolis, MD

for $1,139,400 with 5 bedrooms and 4 full baths. This 3,660 square foot home was built in 1959 on a lot size of 1.06.

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 chefs kitchen, outfitted for the culinary enthusiast, anchors the main level and opens seamlessly to a grand, light-filled living areaan ideal setting for refined entertaining or intimate gatherings. Expansive windows invite the lush landscape indoors, enhancing the homes 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 roomperfect for multigenerational living, distinguished guest accommodations, or an au pair residence. Outside, the estates grounds unfold like a private sanctuary. Mature trees, newly developing gardens, and verdant open spaces create an atmosphere of effortless peacea 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 chefs 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 homeit is a private retreat offering refined luxury, natural beauty, and an unmatched Annapolis lifestyle.

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Single Family Active

Price

$ 1,139,400

Bedrooms

5

Full Bath

4

Property Type

Single Family

Taxes

$ 6,942

Style

Traditional

Lot Size

1.06

Year Built

1959

Town/City

Annapolis

County/Region

Anne Arundel

MLS | Web ID

MDAA2130382

Features
General
Living Area 3660
Sewer On Site Septic
Heating Forced Air Humidifier Zoned
Cooling Central A/C Ductless/Mini-Split
Utilities Cable TV Available Electric Available Natural Gas Available Phone Available Water Available
Possession Settlement Immediate Negotiable
Roof Asphalt
Appliances Washer/Dryer Hookups Only Disposal Dryer Exhaust Fan Extra Refrigerator/Freezer Humidifier Microwave Oven - Self Cleaning Oven/Range - Electric Washer/Dryer Stacked
Zoning R1
Garage Spaces 2.00
Patio/Porch Features Patio(s) Screened
Architectural Style Traditional
Security Features Fire Detection System Main Entrance Lock Security System
Construction Materials Brick Combination Fiber Cement Masonry Shake Siding Wood Siding Other Stick Built
School District ANNE ARUNDEL COUNTY PUBLIC SCHOOLS
Year Built 1959
View Garden/Lawn Trees/Woods Park/Greenbelt
Levels 3
Tax Year 2025
Ownership Fee Simple
Cool Fuel Natural Gas
Accessibility Doors - Lever Handle(s) Doors - Swing In
County ANNE ARUNDEL
New Construction N
Property Type Residential
HOA N
Subdivision Name WINCHESTER ESTATES
Garage Y/N Y
Water Access Y/N Y
Other Structures Above Grade Below Grade
Full Baths 4
Status ACTIVE
Directions Highway 50 Eastbound cross Severn River Bridge Take Exit #27 onto 450 South heading towards Naval Academy Turn Right on Boulter’s Way Turn Right on Winchester Road House is on the right with brick ma
City ANNAPOLIS
Body of Water COOL SPRING COVE
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 46174.00
Tax Annual Amount 6942.0
Home Warranty Y/N Y
Property Condition Very Good
Structure Type Detached
Condo/Coop Association fee Y/N N
Number of Community Docks 0
Bathrooms Full Main Level 2
Bathrooms Count Main Level 2.00
Price Per Sq Ft Total AG 466.78
Acceptable Financing Cash Conventional
Historic Y/N N
Lease Considered Y/N N
Vacation Rental Y/N N
Standard Status Active
Year Built Source Assessor
Association Recreation Fee N
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Interior
Interior Amenities 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
Heating Fuel Central Natural Gas
Basement Fully Finished Walkout Level Other Space For Rooms Side Entrance Outside Entrance Interior Access Improved Heated Garage Access Full Daylight Full Connecting Stairway
Total Fireplaces 2
Fireplace Features Fireplace - Glass Doors Mantel(s) Screen
Hot Water Natural Gas
Basement (Y/N) Y
Heating Y/N Y
Window Features Bay/Bow Screens Storm Wood Frame
Fireplace Y/N Y
Above Grade Finished Area 2441
Half Baths 0
Central Air Y/N Y
Total Bedrooms 5
Below Grade Finished Area 1219
Main Level Bedrooms 2
Below Grade Finished Area Unit Type Square Feet
Laundry Type Dryer In Unit Has Laundry Lower Floor Washer In Unit
Below Grade Finished Area Source Estimated
Above Grade Finished Area Source Estimated
Above Grade Finished Area Unit Type Square Feet
Total Baths 4
Number of Elevators 0
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Exterior
Exterior Amenities Sidewalks Gutter System Secure Storage Street Lights
Pool No Pool
Lot Features Backs to Trees Landscaping Adjoins - Public Land Backs - Parkland Private Rear Yard Trees/Wooded
Water Source Public
Garage Features Garage - Side Entry
Type of Parking Off Street Attached Garage
Foundation Details Block
Water View Y/N N
Lot Size Acres 1.06
Road Surface Type Black Top
Water Body Type Cove
Lot Size Source Assessor
Waterfront Y/N N
Door Features Six Panel Sliding Glass Storm
Water Access Features Private Access
Road Responsibility City/County
Horse Y/N N
Number of Docks 0
Navigable Water Y/N Y
Water Oriented Y/N Y
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Internal Only
Street Number 1 1635
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* Excluded Features
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Equity Property Investments

Broker

ana@epinvestments.com

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Affordability Calculator

$7,687
Per Month
92%
8%
0%
Monthly Principal & Interest
$7,108
Monthly Property Taxes
$579
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3543169 Elementary School
3535420 Middle School
Broadneck High School High School
Pricing History
DatePricePrice ChangeDescription
12/1/2025$1,139,400 -8.69% Price Down
11/2/2025$1,247,900 Listed Price

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1635 Winchester Road, Annapolis, MD, 21409 is a Single Family Home for sale at $1,139,400 with 3,660 sqft and a lot size of 1.06. 1635 Winchester Road has 5 bedrooms, 4.0 baths, and was built in 1959. The property's zip code is 21409 which is in Annapolis, MD