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Kimberley Gundacker
REALTOR®
Cell: (717) 387-3080
Office: (301) 745-1620
  • 529 Lee Circle , Annapolis, MD 21403 Main Photo

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New to the Market
BEDS6 BATHS4 full 1 partial SQUARE FEET5,918 MLS#MDAA2150742
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONHILLSMERE SHORES SCHOOLANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Property Description

Annapolis Stunning Coastal Colonial Waterfront Retreat where every day feels like a vacation. Perfectly positioned on the tranquil waters of the Chesapeake Bay tributaries, this extraordinary waterfront residence at 529 Lee Circle offers an exceptional blend of sophisticated coastal design and effortless indoor-outdoor living. Privately nestled among mature trees, the home enjoys a peaceful setting with panoramic water views, a private pier, a boat house and a floating dock, creating the ultimate Annapolis waterfront retreat. The impressive rear elevation is designed to embrace the waterfront lifestyle, featuring expansive walls of glass that flood the interiors with natural light while framing picturesque water views from nearly every level. Multiple outdoor living spaces—including a spacious waterside deck, an upper-level balcony, and an expansive lawn leading to the 114 feet shoreline—provide the perfect backdrop for entertaining or relaxing while enjoying spectacular sunsets. The boat house with lift, private pier, and protected water dockage offer immediate access to boating, paddleboarding, kayaking, and all the Chesapeake Bay has to offer. Whether departing for a day on the water or enjoying quiet evenings along the shoreline, this property delivers an unmatched waterfront experience. Architecturally, the home combines classic coastal elegance with contemporary comfort. Soft gray siding, crisp white trim, multiple gables, and oversized windows create a timeless façade that complements its natural surroundings. The residence offers approximately 6,000 square feet of living space with two owners suite (one on the main level), generous entertaining areas, multiple fireplaces, and luxurious accommodations designed for both everyday living and grand-scale gatherings. The home was originally built in 1965. In 2016 it went through a complete, down-to-the-studs renovation and expansion to the creation of stunning luxurious waterfront home. Custom-Built by Architect Teresa Todd and Timberlake Homes into a 6-bedroom and 5.5-bathroom residence. Located within the sought-after Hillsmere Shores community, residents enjoy a coveted Annapolis lifestyle with access to a private beach, marina, community pool, playgrounds, and convenient proximity to Historic Downtown Annapolis, waterfront dining, yacht clubs, and the U.S. Naval Academy. This is more than a waterfront home—it is a private Chesapeake Bay sanctuary where luxury, recreation, and timeless coastal beauty come together in one exceptional offering.

529 Lee Circle | MLS# MDAA2150742

This single family home located at 529 Lee Circle , Annapolis, MD 21403 is currently listed for sale with an asking price of $2,650,000. This property was built in 1965 and has 6 bedrooms and 4 full and 1 partial baths with 5918 sq. ft. Lee Circle is located in the HILLSMERE SHORES subdivision within the ANNE ARUNDEL COUNTY PUBLIC SCHOOLS school district. Search HILLSMERE SHORES real estate on kimberleygundacker.homesale.com today.

Upcoming Open Houses

Open House Saturday July 11th, 1:00pm - 3:00pm
Open House Sunday July 12th, 1:00pm - 3:00pm

Property Features

Property Type: Residential - Single Family
Basement: Fully Finished, Improved, Heated, Interior Access, Outside Entrance, Daylight, Full, Sump Pump, Windows
Basement: Yes
Cooling: Central A/C
Fireplaces: 2
Fuel Type: Electric
Garage: 1
Heating: Heat Pump(s)
Home Style: Contemporary, Cape Cod
Lot Size: 0.22 Acres
Roof Type: Architectural Shingle, Metal
Stories: 3.0
Taxes: $13,077
Year Built: 1965

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Built-In Range, Commercial Range, Disposal, Extra Refrigerator/Freezer, Microwave, Range Hood, Six Burner Stove, Stainless Steel Appliances, Washer - Front Loading, Water Conditioner - Owned
Exterior: Boat Storage, BBQ Grill, Roof Deck, Stone Retaining Walls, Underground Lawn Sprinkler
Exterior: Frame
Fireplace: Gas/Propane, Stone, Brick, Mantel(s)
Flooring: Hardwood, Marble, Ceramic Tile, Luxury Vinyl Plank, Carpet, Heated
HOA Fee: $25.00/Annually
Interior: Wood Floors, Wine Storage, Water Treat System, Walk-in Closet(s), Upgraded Countertops, Sprinkler System, Sauna, Recessed Lighting, Primary Bedroom - Bay Front, Primary Bath(s), Pantry, Kitchen - Island, Kitchen - Gourmet, Kitchen - Eat-In, Floor Plan - Open, Family Room Off Kitchen, Exposed Beams, Entry Level Bedroom, Dining Area, Crown Moldings, Combination Kitchen/Living, Combination Kitchen/Dining, Combination Dining/Living, Ceiling Fan(s), Carpet, Butlers Pantry, Built-Ins, Bathroom - Walk-In Shower, Bathroom - Soaking Tub, Bathroom - Stall Shower, Bar, Attic
Lake Name: Duvall Creek
Location: Creek/Stream
Lot: Bulkheaded, Cul-de-sac, Front Yard, Rear Yard
Lot Dimensions: 0.22 Acre(S)
Parking Features: Asphalt Driveway, Gravel Driveway
Parking Notes: 10 Total Parking Spaces
Sewer: Public Sewer
Special View Info: Creek/Stream, Bay
SQFT Above Finished: 4298
SQFT Below Finished: 1620
SQFT Total Finished: 5918
Structure Type: Detached
Total Garage/Parking Spaces: 10
Utilities: Propane
Water: Well
Water Access: Boat - Powered, Canoe/Kayak
Waterfront: Private Dock Site, Boat/Launch Ramp - Private

Local Schools

School District: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Coldwell Banker Realty
Agency Phone: 4102638686

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Estimated Payment

$ 7,760.42 per month $5,897.75 Principal & Interest $1,089.75 Property Tax $772.92 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 07/11/2026. The listing information on this page last changed on 07/11/2026. 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 Sat 07/11/2026 12:03:20 AM EST) or Bright MLS (last updated Fri 07/10/2026 11:57:35 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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Licensed in Pennsylvania & Maryland
Kimberley Gundacker 

11949 Robinwood Drive #100, Hagerstown, MD 21742
301-745-1620

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