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125 S Winchester Road, Annapolis, MD 21409

$7,500,000
  • 125 S Winchester Road, Annapolis, MD 21409 Main Photo

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Price Reduced $1,250,000 on April 21st, 2026
BEDS5 BATHS5 full 2 partial SQUARE FEET11,269 MLS#MDAA2132598
STATUSACTIVE PROPERTY TYPEResidential - Single Family SCHOOLANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Property Description

This Severn River estate is a rare opportunity to own one of the area’s most spectacular properties. Showcasing a negative-edge pool with beach entry and hot tub, 2 private piers to accommodate a variety of vessel sizes including a 100 ft slip, sprawling yard and sweeping views of the river and Naval Academy Bridge. Imagine waking each morning to the sun sparkling off the Severn, its reflection dancing across the water and spilling into a home designed to embrace the view at every turn. This extraordinary residence is both a private retreat and an entertainer’s dream, with expansive balconies and roof decks on every level, making indoor/outdoor living a breeze. Inside, soaring ceilings and walls of glass frame the ever-changing views like a living masterpiece, while the grand chef’s kitchen, stone-floored sunroom, and elegant dining spaces invite gatherings large and small. The primary suite is an entire level of indulgence, complete with soaring ceilings, a fireplace, spa-like bath, wet bar, expansive dressing room, laundry, and its own private balcony for starlit evenings. Additional ensuite bedrooms and a guest suite with kitchenette ensure comfort for family and friends, while the lower level—with wine cellar, kitchenette, and direct access to the pool—extends the living space to the outdoors. With a sandy beach and two private piers, one tucked into Crouches Cove and the other stretching into the Severn river, this estate offers not just a home but a lifestyle of breathtaking vistas on the water, boating adventures at your doorstep, and the unmatched beauty of Annapolis waterfront living. Located in the Blue-Ribbon Broadneck School district and just 5 miles to downtown Annapolis, convenient to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., the location provides the very best this region has to offer in a 30-mile radius. If you are looking for a truly special property with EPIC water views, resort like amenities and a great private setting, this is the property you have been waiting for. Welcome Home!

125 S Winchester Road | MLS# MDAA2132598

This single family home located at 125 S Winchester Road, Annapolis, MD 21409 is currently listed for sale with an asking price of $7,500,000. This property was built in 2003 and has 5 bedrooms and 5 full and 2 partial baths with 11269 sq. ft. S Winchester Road is located within the ANNE ARUNDEL COUNTY PUBLIC SCHOOLS school district. Search Annapolis real estate on www.gilperrone.com today.

Property Features

Property Type: Residential - Single Family
Basement: Connecting Stairway, Daylight, Partial, Full, Fully Finished, Heated, Improved, Interior Access, Rear Entrance, Walkout Level, Windows
Basement: Yes
Cooling: Ceiling Fan(s), Central A/C, Programmable Thermostat
Fireplaces: 3
Fuel Type: Electric, Propane - Owned
Garage: 3
Heating: Forced Air, Programmable Thermostat, Zoned
Home Style: Coastal, Transitional
Lot Size: 2.77 Acres
Stories: 4.0
Taxes: $25,288
Year Built: 2003

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Extra Refrigerator/Freezer, Freezer, Icemaker, Microwave, Oven/Range - Gas, Oven - Double, Range Hood, Refrigerator, Six Burner Stove, Stainless Steel Appliances, Trash Compactor, Washer, Water Conditioner - Owned, Water Heater
Exterior: Combination
Exterior: Extensive Hardscape, Exterior Lighting, Hot Tub, Private Beach, Stone Retaining Walls
Fireplace: Fireplace - Glass Doors, Gas/Propane, Mantel(s), Marble, Stone
Flooring: Hardwood, Stone, Ceramic Tile
Interior: Additional Stairway, Bar, Bathroom - Jetted Tub, Bathroom - Walk-In Shower, Breakfast Area, Ceiling Fan(s), Combination Kitchen/Dining, Combination Kitchen/Living, Dining Area, Family Room Off Kitchen, Floor Plan - Open, Formal/Separate Dining Room, Kitchen - Gourmet, Kitchen - Island, Kitchenette, Pantry, Primary Bath(s), Recessed Lighting, Sprinkler System, Upgraded Countertops, Walk-in Closet(s), Water Treat System, Wet/Dry Bar, WhirlPool/HotTub, Window Treatments, Wine Storage
Lake Name: Severn River/Crouches Pond
Lot: Landscaping, Level, No Thru Street, Poolside, Premium, Private, Rip-Rapped
Lot Dimensions: 2.77 Acre(S)
Parking Notes: 9 Total Parking Spaces
Sewer: On Site Septic, Private Septic Tank
Special View Info: River, Panoramic, Garden/Lawn, Scenic Vista, Water
SQFT Above Finished: 9699
SQFT Below Finished: 1570
SQFT Total Finished: 11269
Structure Type: Detached
Swimming Pool: In Ground, Negative Edge/Infinity, Pool/Spa Combo
Total Garage/Parking Spaces: 9
Water: Well
Water Access: Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access, Sail, Swimming Allowed, Waterski/Wakeboard
Waterfront: Private Dock Site, Rip-Rap, Sandy Beach

Local Schools

High School: BROADNECK
Middle School: SEVERN RIVER
Elementary School: ARNOLD
School District: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: TTR Sotheby's International Realty
Agency Phone: 4102805600

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Estimated Payment

$ 20,986.58 per month $16,691.75 Principal & Interest $2,107.33 Property Tax $2,187.50 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/21/2026. The listing information on this page last changed on 04/21/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 04/21/2026 12:00:32 AM EST) or Bright MLS (last updated Mon 04/20/2026 11:50:00 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Gilbert Perrone 

353 S. Main Street, Bel Air, MD 21014
410-697-8100

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