417 Second Street, Annapolis, MD 21403

$2,555,000
5
BD
4
BA
4,022
SqFt

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Sold Price
$2,555,000
List Price
$2,695,000
Closing Date
Oct 24, 2025
MLS#
MDAA2126566
Year Built
1988
Status
CLOSED
Type
Single Family Residential
Bedrooms
5
Baths All
4
Baths Full
3
Baths Half
1
Living Area
4,022
Total SqFt
4722
County
Anne Arundel
Subdivision
Eastport

Property Description

Perfectly sited on over a quarter-acre gated lot on Second Street, this meticulously maintained Eastport estate offers 4,500+ square feet of luxurious living space and extensive oak flooring in one of Annapolis’ most coveted neighborhoods. Enjoy the tranquility of suburban-style privacy with the walkability of downtown living - just steps to water access, acclaimed restaurants, shopping, and marina life. Inside, generous proportions define the main level. A spacious living room and elegant formal dining room open to the expansive deck and pool area, while a chef’s kitchen boasts a quartzite island, high-end appliances, and a casual eat-in space. The main level also features an updated laundry room, chic powder room, and a dramatic family room with vaulted wood ceilings, gas fireplace, and sliding doors to the outdoor oasis. Upstairs, the serene primary suite features vaulted ceilings, a walk-in closet, and a spa-inspired bath with heated floors, a rainfall shower, double vanity, and heated towel rack. Three additional oversized bedrooms and a stylish hall bath complete the second floor. The third level offers breathtaking views of Historic Annapolis and the Naval Academy from the rooftop balcony - perfect for fireworks or Blue Angel flyovers - and includes a family room, kitchenette, full bath, and bedroom. The fully finished lower level is made for entertaining, with a rec room, custom bar (complete with kegerator and refrigerated drawers), a flexible bonus room ideal for a wine cellar or storage, and a workshop. Step outside to your private resort: a heated in-ground pool and spa with motorized cover, a pergola with adjustable louvers, lush landscaping, and a park-like front yard. Additional features include Hardie siding, composite decking, updated windows and gutters (all completed in 2019), a two-car garage, and a gated driveway. This is a rare Eastport offering where timeless elegance, thoughtful updates, and premier location come together. Welcome Home!

Additional Information

Elementary School
Eastport
Middle School
Annapolis
High School
Annapolis
Other Structures
Above Grade, Below Grade
Structure List
Above Grade, Below Grade
Garage Spaces
2
Pool
Yes
Style
Colonial
Interior Features
Dining Area, Breakfast Area, Kitchen - Eat-In, Kitchen - Gourmet, Primary Bath(s), Built-Ins, Crown Moldings, Upgraded Countertops, Wet/Dry Bar, Wood Floors, Floor Plan - Traditional, Ceiling Fan(s), Family Room Off Kitchen, Formal/Separate Dining Room, Kitchen - Island, Kitchenette, Skylight(s), Walk-in Closet(s), Window Treatments
Basement
Yes
Fireplaces
1
Cooling Fuel
Electric
Cooling
Central A/C
Heating Fuel
Natural Gas
Heating
Forced Air
Hot Water
Tankless, Instant Hot Water, Natural Gas
Sewer Septic
Public Sewer
Water
Public
Tax Year
2025
Possession
Settlement
Days on Market
10
Acres
0.27
Parking
Paved Driveway
Ownership
Fee Simple

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Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .