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 chef’s kitchen, outfitted for the culinary enthusiast, anchors the main level and opens seamlessly to a grand, light-filled living area—an ideal setting for refined entertaining or intimate gatherings. Expansive windows invite the lush landscape indoors, enhancing the home’s 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 room—perfect for multigenerational living, distinguished guest accommodations, or an au pair residence. Outside, the estate’s grounds unfold like a private sanctuary. Mature trees, newly developing gardens, and verdant open spaces create an atmosphere of effortless peace—a 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 * Extensive cutting-edge electronic pet fence system * Exclusive neighborhood water-access privileges * Right next door to the beautiful Baltimore Annapolis Trail Park * Gourmet chef’s 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 home—it is a private retreat offering refined luxury, natural beauty, and an unmatched Annapolis lifestyle.
Under contract
Price cut: $108.5K (12/1)
$1,139,400
1635 Winchester Rd, Annapolis, MD 21409
5beds
3,660sqft
Est.:
Single Family Residence
Built in 1959
1.06 Acres Lot
$1,108,700 Zestimate®
$311/sqft
$-- HOA
What's special
Verdant open spacesMature treesMagnificently landscaped park-like acreTimeless eleganceExpansive windowsCustom-built residenceExclusive neighborhood water-access privileges
- 53 days |
- 1,442 |
- 51 |
Zillow last checked: 8 hours ago
Listing updated: December 25, 2025 at 12:28am
Listed by:
Ana Lopez 919-360-0430,
Equity Property Investments 9193600430
Source: Bright MLS,MLS#: MDAA2130382
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 4
- Main level bathrooms: 2
- Main level bedrooms: 2
Basement
- Area: 1219
Heating
- Forced Air, Humidity Control, Zoned, Central, Natural Gas
Cooling
- Central Air, Ductless, Natural Gas
Appliances
- Included: Disposal, Dryer, Exhaust Fan, Extra Refrigerator/Freezer, Humidifier, Microwave, Self Cleaning Oven, Oven/Range - Electric, Washer/Dryer Stacked, Gas Water Heater
- Laundry: Dryer In Unit, Has Laundry, Lower Level, Washer In Unit, Washer/Dryer Hookups Only
Features
- Attic, 2nd Kitchen, Kitchen - Efficiency, Family Room Off Kitchen, Breakfast Area, Dining Area, Built-in Features, Chair Railings, Crown Molding, Primary Bath(s), Floor Plan - Traditional, Dry Wall, Plaster Walls
- Flooring: Wood
- Doors: Six Panel, Sliding Glass, Storm Door(s)
- Windows: Bay/Bow, Screens, Storm Window(s), Wood Frames
- Basement: Finished,Walk-Out Access,Other,Space For Rooms,Side Entrance,Exterior Entry,Interior Entry,Improved,Heated,Garage Access,Full,Connecting Stairway
- Number of fireplaces: 2
- Fireplace features: Glass Doors, Mantel(s), Screen
Interior area
- Total structure area: 3,660
- Total interior livable area: 3,660 sqft
- Finished area above ground: 2,441
- Finished area below ground: 1,219
Property
Parking
- Total spaces: 2
- Parking features: Garage Faces Side, Off Street, Attached
- Attached garage spaces: 2
Accessibility
- Accessibility features: Doors - Lever Handle(s), Doors - Swing In
Features
- Levels: Three
- Stories: 3
- Patio & porch: Patio, Screened
- Exterior features: Sidewalks, Rain Gutters, Storage, Street Lights
- Pool features: None
- Has view: Yes
- View description: Garden, Trees/Woods, Park/Greenbelt
- Waterfront features: Private Access, Cove
- Body of water: Cool Spring Cove
Lot
- Size: 1.06 Acres
- Features: Backs to Trees, Landscaped, Adjoins - Public Land, Backs - Parkland, Private, Rear Yard, Wooded
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 020300008574025
- Zoning: R1
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Brick, Combination, Fiber Cement, Masonry, Shake Siding, Wood Siding, Other, Stick Built
- Foundation: Block
- Roof: Asphalt
Condition
- Very Good
- New construction: No
- Year built: 1959
- Major remodel year: 2020
Utilities & green energy
- Sewer: On Site Septic
- Water: Public
- Utilities for property: Cable Available, Electricity Available, Natural Gas Available, Phone Available, Water Available
Community & HOA
Community
- Security: Fire Alarm, Main Entrance Lock, Security System
- Subdivision: Winchester Estates
HOA
- Has HOA: No
Location
- Region: Annapolis
Financial & listing details
- Price per square foot: $311/sqft
- Tax assessed value: $631,100
- Annual tax amount: $6,942
- Date on market: 11/8/2025
- Listing agreement: Exclusive Agency
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Road surface type: Black Top
Estimated market value
$1,108,700
$1.05M - $1.16M
$3,644/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 12/25/2025 | Contingent | $1,139,400$311/sqft |
Source:  Bright MLS #MDAA2130382 Report a problem | ||
| 12/1/2025 | Price change | $1,139,400-8.7%$311/sqft |
Source: Bright MLS #MDAA2130382 Report a problem | ||
| 11/8/2025 | Listed for sale | $1,247,900+73.6%$341/sqft |
Source: Bright MLS #MDAA2130382 Report a problem | ||
| 2/8/2008 | Sold | $719,000$196/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $631,100 +5.3% |
| 2024 | $6,562 +0.3% | $599,300 |
| 2023 | $6,544 +4.5% | $599,300 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$5,605/mo
Principal & interest
$4418
Property taxes
$788
Home insurance
$399
Climate risks
Neighborhood: 21409
Nearby schools
GreatSchools rating
- 10/10Arnold Elementary SchoolGrades: K-5Distance: 1.3 mi
- 9/10Severn River Middle SchoolGrades: 6-8Distance: 3 mi
- 8/10Broadneck High SchoolGrades: 9-12Distance: 2.8 mi
Schools provided by the listing agent
- Elementary: Arnold
- Middle: Severn River
- High: Broadneck
- District: Anne Arundel County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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