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Sold

417 SECOND STREET

417 SECOND STREET, ANNAPOLIS, MD 21403

$2,555,000
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!

5
beds

4
baths

4,722 Sq.Ft. LIVING AREA

0.27 Acres lot

Brad Kappel

Brad Kappel

  • title Executive Vice President, Global Real Estate Advisor at TTR Sotheby’s International Realty
  • PHONE 410.279.9476
  • EMAIL [email protected]

Features & Amenities

Interior

  • total bedrooms5
  • Total bathrooms4
  • full bathrooms3
  • half bathroom1
  • Laundry room Main Floor
  • Flooring Hardwood
  • Fireplace Gas/Propane
  • APPLIANCES Dishwasher, Disposal, Dryer - Front Loading, Exhaust Fan, Freezer, Icemaker, Humidifier, Oven - Double, Oven - Self Cleaning, Refrigerator, Washer - Front Loading, Built-In Microwave, Commercial Range, Range Hood, Stainless Steel Appliances, Six Burner Stove, Washer/Dryer Stacked, Water Heater - Tankless
  • other 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

Area & Lot

  • Status Sold
  • Date Sold October 24, 2025
  • Living Area4,722 Sq.Ft.
  • Total Area4,972 Sq.Ft.
  • Lot Area0.27 Acres
  • MLS® IDMDAA2126566
  • TypeResidential
  • YEAR BUILT1988
  • NeighborhoodDowntown Annapolis & Eastport, MD
  • Architecture StylesColonial
  • View DescriptionCity, Garden/Lawn
  • Elementary SchoolEASTPORT
  • Middle SchoolANNAPOLIS
  • High SchoolANNAPOLIS
  • School DistrictANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Exterior

  • STORIES4
  • Garage Space2.0
  • water SourcePublic
  • PoolYes - Personal
  • roofArchitectural Shingle
  • lot featuresLandscaping, Private, Front Yard, Level, Rear Yard
  • parkingOff Street, Driveway, Attached Garage
  • HEAT TYPEForced Air
  • AIR CONDITIONINGCentral A/C
  • sewerPublic Sewer
  • SubstructureBlock, Slab
  • Disability FeaturesNone
  • security FeaturesElectric Alarm, Security System, Smoke Detector, Carbon Monoxide Detectors
  • other exterior FeaturesExtensive Hardscape, Exterior Lighting, Hot Tub, Roof Deck

Financial

  • Sales Price$2,555,000
  • Real Estate Tax $23,704/yr
  • Zoning R2 - NC

Downtown Annapolis & Eastport, MD

Downtown Annapolis and Eastport embody a rich maritime heritage and architectural splendor, offering an elegant and approachable lifestyle.

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Brad Kappel and his team are dedicated to helping you find your dream home and assisting with any selling needs you may have. Make Your Move today!

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