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125 S WINCHESTER ROAD, ANNAPOLIS, MD, 21409

$8,750,000

5 beds
5 full baths
2 half baths
11,269 sq. ft

125 S WINCHESTER ROAD, ANNAPOLIS, MD, 21409
$8,750,000 Coming Soon

Beds 5
Baths 6
Sq. ft 11,269

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Coming Soon

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!

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Property Features

Year Built:
2003

Listing ID:
MDAA2132598

Bathrooms:
5 full , 2 half

List Date:
February 17, 2026

Property Type:
Single Family Residential

Architecture Style:
Coastal, Transitional

Subdivision:
NONE AVAILABLE

County:
ANNE ARUNDEL

Appliances:

Total Taxes:
$25,288

Courtesy of TTR Sotheby's International Realty

This content was last updated on April 16, 2026 21:12

Name	Type	Level	Grades	Address
Broadneck High School	Public	High	9-12	1265 Green Holly Dr, Annapolis, MD 21409
District: Anne Arundel County Public Schools Grade Span: 9 - 12 Admission: Public Address: 1265 Green Holly Dr, Annapolis, MD 21409 Phone: 410-757-1300 Website: http://www.broadneck.org/ Teachers: 115 Students: 2143 Ratio: 19:1 Students/Teacher Gender: 50% Male / 50% Female Lunch: 14% Free / 3% Reduced Student/Teacher ratio Enrollment
Severn River Middle School	Public	Middle	6-8	241 Peninsula Farm Rd, Arnold, MD 21012
District: Anne Arundel County Public Schools Grade Span: 6 - 8 Admission: Public Address: 241 Peninsula Farm Rd, Arnold, MD 21012 Phone: 410-544-0922 Website: http://www.aacps.org/ Teachers: 47 Students: 675 Ratio: 14:1 Students/Teacher Gender: 50% Male / 50% Female Lunch: 16% Free / 4% Reduced Student/Teacher ratio Enrollment
Arnold Elementary School	Public	Primary	KG-5	95 Joyce Ln E, Arnold, MD 21012
District: Anne Arundel County Public Schools Grade Span: KG - 5 Admission: Public Address: 95 Joyce Ln E, Arnold, MD 21012 Phone: 410-757-4400 Website: http://www.aacps.org Teachers: 30 Students: 454 Ratio: 15:1 Students/Teacher Gender: 55% Male / 45% Female Lunch: 10% Free / 3% Reduced Student/Teacher ratio Enrollment

Address: Enrollment

Address: Enrollment

Name	Type	Level	Grades	Address
Book of Life Academy	Private	Elementary	PK-5	913 Cedar Park Rd, Annapolis, MD 21401
Grade Span: PK - 5 Admission: Private Address: 913 Cedar Park Rd, Annapolis, MD 21401 Phone: 410-263-2600 Website: http://www.bookoflifeacademy.com/ Teachers: 10 Students: 58 Ratio: 6:1 Students/Teacher Gender: 47% Male / 53% Female Student/Teacher ratio Enrollment
Chesapeake Montessori School	Private	Elementary	PK-8	30 Old Mill Bottom Rd N, Annapolis, MD 21409
Grade Span: PK - 8 Admission: Private Address: 30 Old Mill Bottom Rd N, Annapolis, MD 21409 Phone: 410-757-4740 Teachers: 8 Students: 78 Ratio: 10:1 Students/Teacher Gender: 37% Male / 63% Female Student/Teacher ratio Enrollment
Key School	Private	Combined Elementary/Secondary	PK-12	534 Hillsmere Dr, Annapolis, MD 21403
Grade Span: PK - 12 Admission: Private Address: 534 Hillsmere Dr, Annapolis, MD 21403 Phone: 443-321-7833 Website: http://www.keyschool.org Teachers: 64 Students: 598 Ratio: 9:1 Students/Teacher Gender: 53% Male / 47% Female Student/Teacher ratio Enrollment
Montessori International Childrens House	Private	Elementary	PK-6	1641 Winchester Rd, Annapolis, MD 21409
Grade Span: PK - 6 Admission: Private Address: 1641 Winchester Rd, Annapolis, MD 21409 Phone: 410-757-7789 Website: http://www.montessoriinternational.org/ Teachers: 10 Students: 75 Ratio: 8:1 Students/Teacher Gender: 47% Male / 53% Female Student/Teacher ratio Enrollment
Naval Academy Primary School	Private	Elementary	PK-5	74 Greenbury Point Rd, Annapolis, MD 21402
Grade Span: PK - 5 Admission: Private Address: 74 Greenbury Point Rd, Annapolis, MD 21402 Phone: 410-757-3090 Website: http://www.napschool.com/ Teachers: 24 Students: 195 Ratio: 8:1 Students/Teacher Gender: 51% Male / 49% Female Student/Teacher ratio Enrollment
Pathways School--Anne Arundel	Private	Secondary	7-12	1819 Bay Ridge Ave Ste 340, Annapolis, MD 21403
Grade Span: 7 - 12 Admission: Private Address: 1819 Bay Ridge Ave Ste 340, Annapolis, MD 21403 Phone: 301-649-0778 Teachers: 4 Students: 30 Ratio: 7:1 Students/Teacher Gender: 53% Male / 47% Female Student/Teacher ratio Enrollment
St Annes School of Annapolis	Private	Elementary	PK-8	3112 Arundel on the Bay Rd, Annapolis, MD 21403
Grade Span: PK - 8 Admission: Private Address: 3112 Arundel on the Bay Rd, Annapolis, MD 21403 Phone: 410-263-8650 Website: http://st.annesschool.org/ Teachers: 20 Students: 234 Ratio: 12:1 Students/Teacher Gender: 66% Male / 34% Female Student/Teacher ratio Enrollment
St Margaret's Day School	Private	Elementary	PK-KG	1605 Pleasant Plains Rd, Annapolis, MD 21409
Grade Span: PK - KG Admission: Private Address: 1605 Pleasant Plains Rd, Annapolis, MD 21409 Phone: 410-757-2333 Website: http://www.st-margarets.org/ Teachers: 2 Students: 33 Ratio: 17:1 Students/Teacher Gender: 48% Male / 52% Female Student/Teacher ratio Enrollment
St Martins Lutheran Church School	Private	Elementary	PK-8	1120 Spa Rd, Annapolis, MD 21403
Grade Span: PK - 8 Admission: Private Address: 1120 Spa Rd, Annapolis, MD 21403 Phone: 410-269-1955 Teachers: 16 Students: 118 Ratio: 7:1 Students/Teacher Gender: 55% Male / 45% Female Student/Teacher ratio Enrollment
St Marys High School	Private	Secondary	9-12	113 Duke of Gloucester St, Annapolis, MD 21401
Grade Span: 9 - 12 Admission: Private Address: 113 Duke of Gloucester St, Annapolis, MD 21401 Phone: 410-263-3294 Website: http://www.stmarysannapolis.org/ Teachers: 34 Students: 496 Ratio: 15:1 Students/Teacher Gender: 54% Male / 46% Female Student/Teacher ratio Enrollment
The Harbour School at Annapolis	Private	Combined Elementary/Secondary	1-12	1277 Green Holly Dr, Annapolis, MD 21409
Grade Span: 1 - 12 Admission: Private Address: 1277 Green Holly Dr, Annapolis, MD 21409 Phone: 410-974-4248 Website: http://harbourschool.org Teachers: 26 Students: 184 Ratio: 7:1 Students/Teacher Gender: 57% Male / 43% Female Student/Teacher ratio Enrollment
Weems Creek Nursery School & Kindergarten	Private	Combined Elementary/Secondary	PK-PK	238 Kirkley Rd, Annapolis, MD 21401
Grade Span: PK - PK Admission: Private Address: 238 Kirkley Rd, Annapolis, MD 21401 Phone: 410-266-5522 Teachers: 1 Students: 16 Ratio: 16:1 Students/Teacher Gender: 44% Male / 56% Female Student/Teacher ratio Enrollment

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125 S WINCHESTER ROAD, ANNAPOLIS, MD, 21409

$8,750,000