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!
Sold for $2,555,000
$2,555,000
417 2nd St, Annapolis, MD 21403
5beds
4,722sqft
Single Family Residence
Built in 1988
0.27 Acres Lot
$2,590,100 Zestimate®
$541/sqft
$6,119 Estimated rent
Home value
$2,590,100
$2.41M - $2.77M
$6,119/mo
Zestimate® history
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Zillow last checked: 7 hours ago
Listing updated: October 24, 2025 at 03:59am
Listed by:
Brad Kappel 410-279-9476,
TTR Sotheby's International Realty,
Co-Listing Agent: Alex M Clark 443-924-7231,
TTR Sotheby's International Realty
Bought with:
Steve Knopf, 647088
Engel & Volkers Annapolis
Source: Bright MLS,MLS#: MDAA2126566
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Basement
- Area: 950
Heating
- Forced Air, Natural Gas
Cooling
- Central Air, Electric
Appliances
- Included: Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Humidifier, Double Oven, Self Cleaning Oven, Refrigerator, Washer, Microwave, Range, Range Hood, Stainless Steel Appliance(s), Six Burner Stove, Washer/Dryer Stacked, Tankless Water Heater, Instant Hot Water, Gas Water Heater
- Laundry: Main Level
Features
- Dining Area, Breakfast Area, Eat-in Kitchen, Kitchen - Gourmet, Primary Bath(s), Built-in Features, Crown Molding, Upgraded Countertops, Bar, Floor Plan - Traditional, Ceiling Fan(s), Family Room Off Kitchen, Formal/Separate Dining Room, Kitchen Island, Kitchenette, Walk-In Closet(s), Dry Wall
- Flooring: Hardwood, Wood
- Doors: Sliding Glass, Insulated
- Windows: Skylight(s), Screens, Double Hung, Double Pane Windows, Low Emissivity Windows, Sliding, Window Treatments
- Basement: Improved,Interior Entry,Partially Finished,Sump Pump,Water Proofing System,Windows,Workshop
- Number of fireplaces: 1
- Fireplace features: Gas/Propane
Interior area
- Total structure area: 4,972
- Total interior livable area: 4,722 sqft
- Finished area above ground: 4,022
- Finished area below ground: 700
Property
Parking
- Total spaces: 6
- Parking features: Garage Door Opener, Garage Faces Front, Driveway, Off Street, Attached
- Attached garage spaces: 2
- Uncovered spaces: 4
Accessibility
- Accessibility features: None
Features
- Levels: Four
- Stories: 4
- Patio & porch: Deck, Roof Deck
- Exterior features: Extensive Hardscape, Lighting, Balcony
- Has private pool: Yes
- Pool features: Heated, In Ground, Private
- Has spa: Yes
- Spa features: Heated, Hot Tub
- Fencing: Decorative,Full,Other,Privacy
- Has view: Yes
- View description: City, Garden
Lot
- Size: 0.27 Acres
- Features: Landscaped, Private, Front Yard, Level, Rear Yard
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 020600090051901
- Zoning: R2 - NC
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Cement Siding, HardiPlank Type
- Foundation: Block, Slab
- Roof: Architectural Shingle
Condition
- Excellent,Very Good
- New construction: No
- Year built: 1988
- Major remodel year: 2016
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & neighborhood
Security
- Security features: Electric Alarm, Security System, Smoke Detector(s), Carbon Monoxide Detector(s)
Location
- Region: Annapolis
- Subdivision: Eastport
- Municipality: Annapolis
Other
Other facts
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional,VA Loan
- Ownership: Fee Simple
- Road surface type: Black Top
Price history
| Date | Event | Price |
|---|---|---|
| 10/24/2025 | Sold | $2,555,000-5.2%$541/sqft |
Source:  Bright MLS #MDAA2126566 Report a problem | ||
| 10/6/2025 | Pending sale | $2,695,000$571/sqft |
Source: Bright MLS #MDAA2126566 Report a problem | ||
| 9/27/2025 | Contingent | $2,695,000$571/sqft |
Source: Bright MLS #MDAA2126566 Report a problem | ||
| 9/18/2025 | Listed for sale | $2,695,000+107.3%$571/sqft |
Source: Bright MLS #MDAA2126566 Report a problem | ||
| 3/27/2015 | Sold | $1,300,000-3.7%$275/sqft |
Source: Public Record Report a problem | ||
| 2/26/2015 | Pending sale | $1,350,000$286/sqft |
Source: Coldwell Banker Residential Brokerage - Annapolis Church #AA8548838 Report a problem | ||
| 2/6/2015 | Listed for sale | $1,350,000$286/sqft |
Source: Coldwell Banker Residential Brokerage - Annapolis Church #AA8548838 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $20,077 -3% | $1,654,167 +14.8% |
| 2024 | $20,708 +17.4% | $1,441,033 +17.4% |
| 2023 | $17,633 +3.7% | $1,227,900 +1.7% |
| 2022 | $17,009 +1.7% | $1,207,167 +1.7% |
| 2021 | $16,717 +1.7% | $1,186,433 +1.8% |
| 2020 | $16,436 -0.1% | $1,165,700 |
| 2019 | $16,448 +1.4% | $1,165,700 |
| 2018 | $16,215 +3.1% | $1,165,700 -3.3% |
| 2017 | $15,728 | $1,205,200 +5.2% |
| 2016 | -- | $1,145,167 +5.5% |
| 2015 | -- | $1,085,133 +5.9% |
| 2014 | -- | $1,025,100 |
| 2013 | -- | $1,025,100 |
| 2012 | -- | $1,025,100 -5.3% |
| 2011 | -- | $1,082,380 +0.7% |
| 2010 | -- | $1,075,272 +0.7% |
| 2009 | -- | $1,068,166 +0.7% |
| 2008 | -- | $1,061,060 +11.6% |
| 2007 | -- | $950,476 +13.2% |
| 2006 | -- | $839,893 +15.2% |
| 2005 | -- | $729,310 +13.2% |
| 2004 | -- | $644,486 +15.2% |
| 2003 | -- | $559,663 +17.9% |
| 2002 | -- | $474,840 +4.4% |
| 2001 | -- | $454,622 |
Find assessor info on the county website
Neighborhood: 21403
Nearby schools
GreatSchools rating
- 6/10Eastport Elementary SchoolGrades: PK-5Distance: 0.3 mi
- 4/10Annapolis Middle SchoolGrades: 6-8Distance: 2 mi
- 5/10Annapolis High SchoolGrades: 9-12Distance: 4.6 mi
Schools provided by the listing agent
- Elementary: Eastport
- Middle: Annapolis
- High: Annapolis
- 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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Estimated market value
$2,590,100
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$2,590,100