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1604 WINCHESTER ROAD
Annapolis, MD 21409
Dec 2025
SOLD
$12,500,000
Sold Price
7
Beds
13
Baths
9
Garage
22.52
Acres
1924
Yr. Built
MLS# MDAA2102408
Cumulative Days on Market: 528 · Includes prior listings · Currently listed since 01/24/25 · Data provided by the MLS.

Property Description

THE FRIARY a Trophy property in a league of its own! Set on 23 private acres overlooking a gracious bend of the Severn River with 1, 500ft of prime waterfrontage, just minutes from downtown Annapolis and less than an hour from the nation's capital, lies one of the most distinctive estates offered for sale on the East Coast. A true architectural masterpiece, this exquisite 35, 000+ sqft residence, is the result of a mammoth and complex renovation that brought it back to its classic Georgian style yet with an acknowledgment of the owner's contemporary tastes and interests. Formerly a Capuchin monastery, this stately brick structure offers modern amenities for comfortable family living yet easily accommodates elegant grand scale entertainment and private events. The attention to detail and emphasis on proportions and craftsmanship are unparalleled. The exterior features spectacular 270 degree river views, nine car garage, roof garden, pool pavilion, 60 feet infinity edge pool, tennis court and direct access by funicular to a 6 slip private dock with 10' MLW and boat lift. Step into the main core of the home, where 18th-century elements, like original heart pine floors and foyer arch moldings, have been flawlessly preserved. A cleverly designed limestone rotunda containing a conservatory and atrium lead to either of the house’s wings: the impeccably appointed guest wing with spacious common room, or the chapel-turned-ballroom with sweeping limestone fireplace, herringbone teak floors, and arched double doors with a picturesque terrace beyond. The extraordinary estate contains a total of seven bedrooms, eight bathrooms and eighteen fireplaces, formal dining room and formal parlor, commercial size gourmet kitchen, over sized ballroom, conservatory, family room, library, music room, indoor spa, game room, wine cellar, catering kitchen, work shop, and a secret vault. Additional structures on the property include a three bedroom, two bath-guest / staff house, an Asian tea house and mechanical facilities. Only minutes from Washington D.C. and multiple international airports, this elegant and opulent property is worlds away from the hustle and bustle of everyday life yet offers an easy commute to several major metropolitan cities. Unmatched opulence and privacy awaits on the Severn River!

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Property Highlights

Sold Price
12500000
Property Type
Residential
Property Sub Type
Single Family Residence
Architectural Style
Georgian
Bedrooms
7
Total Bathrooms
13
Living Area
35,435
Price / Sqft
$564
Acres
22.52
Year Built
1924
Condition
Excellent
Cumulative Days On Market
246

Location

City/Township
ANNAPOLIS
Waterfront
Yes
View
River, Scenic Vista, Trees/Woods, Garden/Lawn
Subdivision
WINCHESTER ESTATES
County
ANNE ARUNDEL-MD
Zoning
R1

Lake/Waterfront Information

Water Body Name
Severn River
Waterfront Features
Private Dock Site, Rip-Rap

Property Details

Price
$19,995,000
Sold Price
12500000
Condition
Excellent
Property Type
Residential
Property Sub Type
Single Family Residence

Building

Levels
4

Community

Local Schools

Elementary School
ARNOLD
Middle School
SEVERN RIVER
High School
BROADNECK

Interior Features

Bedrooms and Bathrooms

Total Bathrooms
13
Full Bathrooms
8
1/2 Bathrooms
5
Bedrooms
7

Rooms and Basement

Has Basement
Yes
Basement Features
Fully Finished

Area and Spaces

Living Area
35,435
Above Grade Finished Area
30,552
Below Grade Finished Area
4,883

Appliances

Appliances
Built-In Microwave, Cooktop, Dishwasher, Oven - Double, Range Hood, Water Heater, Washer, Refrigerator, Dryer

Interior Features

Interior Features
2nd Kitchen, Bar, Built-Ins, Combination Kitchen/Living, Crown Moldings, Double/Dual Staircase, Exposed Beams, Kitchen - Gourmet, Wainscotting, Walk-in Closet(s), Wood Floors, Wine Storage, Window Treatments
Flooring
Solid Hardwood, Stone, Marble
Accessibility Features
Other
Security Features
Security Gate, Security System, Surveillance Sys, Monitored
Fireplace Features
Gas/Propane, Marble, Wood

Heating and Cooling

Heating Features
Heat Pump(s)
Has Fireplace
Yes
Fireplaces
13

Building Details

Construction

Architectural Style
Georgian
Builders Model
THE FRIARY
Builder
ILEX Construction
Year Built
1924
Foundations
Other
Structure Design Type
Detached

Materials

Construction Materials
Brick, Stone
Roof
Slate

Terms

Terms

Ownership
Fee Simple
Inclusions
see documents for inclusions/exclusions
Cumulative Days On Market
246

Taxes

Tax

Tax (Annual)
$111,173

Heating, Cooling & Utilities

Cooling Features
Central A/C, Zoned

Utilities

Sewer
Private Septic Tank, On Site Septic
Water Source
Public

Lot

Acres
22.52
Lot Size Area Sq Ft
980,971
Lot Features
Premium, Private, Partly Wooded, Rip-Rapped, Side Yard(s)

Exterior Features

Exterior Features
BBQ Grill, Boat Storage, Extensive Hardscape, Exterior Lighting, Outbuilding(s), Water Fountains
Patio And Porch Features
Balconies- Multiple, Patio, Porch, Terrace

Parking

Garage Capacity
9
Parking Features
Private

Pool Features

Pool Features
In Ground, Heated, Indoor
Listed by TTR Sotheby's International Realty
Listing Data last updated 09/11/2026 11:20 am
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Property History

34 days ago
Property information last updated
284 days ago
Date Sold
594 days ago
Status Active. This is the date the listing was placed on market.
Cumulative Days on Market: 528 days (includes prior listings) · Currently listed since January 24, 2025. Data provided by the MLS.

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