Back to Search
125 Winchester Rd, Annapolis, MD 21409
125 Winchester Rd, Annapolis, MD 21409 3D Tour
125 Winchester Rd, Annapolis, MD 21409 Explore 3D Tour
125 Winchester Rd, Annapolis, MD 21409
125 Winchester Rd, Annapolis, MD 21409
125 Winchester Rd, Annapolis, MD 21409
125 Winchester Rd, Annapolis, MD 21409

125 Winchester Rd Annapolis, MD 21409

$8,750,000

COMING SOON
Beds
5
Baths
7
Sqft
11,269
Acres
2.77
Year
2003
Days on Site
45
Property Type
Residential
Sub Type
Per Square Foot
$776
Date Listed
Feb 17, 2026

Description of 125 Winchester Rd, Annapolis, MD 21409

Listing details for 125 Winchester Rd, Annapolis, MD 21409 : 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!
Listing Updated : 03-27-2026 at 8:32 PM EDT
Listing Provided By : Bradley R Kappel, 4102799476, [email protected], TTR Sotheby's International Realty
Source :

Bright MLS, MLS#: MDAA2132598

Manage Property Details Page

Home Worth Check

Interested in 125 Winchester Rd, Annapolis MD, 21409?

By proceeding, you consent to receive calls, texts and voicemails at the number you provided (may be recorded and may be autodialed and use prerecorded and artificial voices), and email, from Dell Residential Group about your inquiry and other home-related matters. Msg/data rates may apply. This consent applies even if you are on a do not call list and is not a condition of any purchase.

Location of 125 Winchester Rd, Annapolis, MD 21409

Google Map
Mortgage Calculator
Listing Price
Down Payment
Interest Rate

Schools Near 125 Winchester Rd, Annapolis, MD 21409

Homes Similar to 125 Winchester Rd, Annapolis, MD 21409

HomeAnnapolisNone Available
What’s Your Home or Condo Worth Today?
Find out what your home or condo is worth in today’s market with a FREE Comparative Market Analysis from a top local Realtor.
Dell Residential Group on FacebookDell Residential Group on LinkedInDell Residential Group on Google
Company
Dell Jeanty
C: (202) 441-2348
E: Email Us
SAMSON PROPERTIES
4720A Langston BLVD
Arlington, VA 22207
About
Contact
Real Estate Blog

MLS® Disclaimer     

MLS Logo© BRIGHT, All Rights Reserved. Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which it participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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

Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed 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 request of the seller.
non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
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.