About 417 Second St
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!
Features of 417 Second St
| MLS® # | MDAA2126566 |
|---|---|
| Price | $2,695,000 |
| Bedrooms | 5 |
| Bathrooms | 3.50 |
| Full Baths | 3 |
| Half Baths | 1 |
| Square Footage | 4,722 |
| Acres | 0.27 |
| Year Built | 1988 |
| Type | Residential |
| Sub-Type | Detached |
| Style | Colonial |
| Status | Pending |
Community Information
| Address | 417 Second St |
|---|---|
| Subdivision | EASTPORT |
| City | ANNAPOLIS |
| County | ANNE ARUNDEL-MD |
| State | MD |
| Zip Code | 21403 |
| Senior Community | N |
Amenities
| Amenities | Master Bath(s), Built-Ins, Crown Molding, Upgraded Countertops, Wet Bar/Bar, Wood Floors, CeilngFan(s), Formal/Separate Dining Room, Skylight(s), Walk-in Closet(s), Shades/Blinds |
|---|---|
| Parking Type | Off Street, Driveway, Attached Garage |
| Parking | Paved Driveway |
| # of Garages | 2 |
| Garages | Garage Door Opener, Garage - Front Entry |
| View | City, Garden/Lawn |
| Is Waterfront | No |
| Pool Type | Yes - Personal |
| Pool | Pool (In-Ground), Heated |
Interior
| Interior Features | Floor Plan-Traditional |
|---|---|
| Appliances | Dishwasher, Disposal, Dryer-front loading, Exhaust Fan, Freezer, Icemaker, Humidifier, Oven-Double, Oven-Self Cleaning, Refrigerator, Washer-front loading, Built-In Microwave, Range hood, Stainless Steel Appliances, Washer/Dryer Stacked, Water Heater - Tankless, Six burner stove, Commercial Range |
| Heating | Forced Air |
| Cooling | Central A/C |
| Fireplace | Yes |
| # of Fireplaces | 1 |
| Fireplaces | Gas/Propane |
| # of Stories | 4 |
| Stories | 4 |
| Has Basement | Yes |
| Basement | Improved, Interior Access, Partially Finished, Sump Pump, Water Proofing System, Windows, Workshop |
| Central Air | Y |
Exterior
| Exterior | HardiPlank |
|---|---|
| Exterior Features | Exterior Lighting, Roof Deck, Deck(s), Balcony, Fenced-Fully, Privacy Fence, Hot Tub, Extensive Hardscape, Decorative Fence, Fence, Pool (In-Ground) |
| Style | Colonial |
| Lot Description | Landscaping, Private, Front Yard, Level, Rear Yard |
| Windows | Skylights, Screens, Double Hung, Double Pane, Low-E, Sliding |
| Roof | Architectural Shingle |
| New Construction | N |
| Foundation | Block, Slab |
School Information
| District | ANNE ARUNDEL COUNTY PUBLIC SCHOOLS |
|---|---|
| Elementary | EASTPORT |
| Middle | ANNAPOLIS |
| High | ANNAPOLIS |
Additional Information
| Date Listed | September 17th, 2025 |
|---|---|
| Days on Market | 10 |
| Zoning | R2 - NC |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | TTR Sotheby's International Realty |
|---|---|
| Contact Info | (410) 280-5600 |