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$1,495,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,077 Sq. Ft.
  • Updated 7 hours ago

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Open House: 1:00 PM - 3:00 PM

Sunday 5/10 1:00 PM - 3:00 PM

417 Chesapeake Avenue,Annapolis, MD 21403

417 Chesapeake AvenueAnnapolisMD21403

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This exceptional 3-bedroom, 2.5-bath sun-drenched contemporary home sits on a spacious Eastport corner lot. Enjoy the vibrant Eastport lifestyle from your newly updated, well-maintained oasis featuring warm hardwood floors and generous living, dining, and kitchen areas. The open layout complements the coastal Eastport vibe, while the inviting wraparound porch is great for morning coffee or an evening cocktail. The living room's focal point is a gas fireplace that reflects off the beautiful wood floors and opens to the gourmet kitchen and newly designed dining area. The second level is dedicated entirely to the spacious primary spa-inspired suite with an oversized walk-in closet, custom built-ins, and an updated sublime bath with walk-in shower and heated floors. A hidden laundry room adds convenience. The private east-facing deck overlooks the rear yard, offering stunning sunrises to start your day. The third level features two bedrooms and an elegant shared bath, with one bedroom enjoying winter water views. The fourth-floor loft can serve as a bedroom, office, or exercise space. The expansive back patio and side yard are ideal for BBQs and soaking in the Eastport atmosphere. Two highly coveted off-street parking spaces are a rare find. Stroll Eastport streets, dine at five-star restaurants, enjoy cozy pubs, or watch boating activity from street-end parks. You're moments from yacht clubs and marinas. Downtown Annapolis and the Naval Academy are close by via the charming Spa Creek drawbridge or the iconic water taxi. The Eastport peninsula is flanked by two creeks with quick access to the Severn River and Chesapeake Bay. Annapolis offers charm and sophistication with colleges, music venues, galleries, street fairs, acclaimed boat shows, and proximity to two major cities. Much of the home was updated to a high standard in 2024-25. Located just 5 miles from Route 50 and 97, you'll have direct access to BWI and Washington, DC. Welcome home to your Eastport dream!

Full Property Details for 417 Chesapeake Ave

General

  • Price: $1,495,000
  • Taxes: $15,702 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDAA2144320
  • Updated: 5/9/2026
  • Added to Site: Today

Interior

  • Rooms/Areas: Primary Bedroom, Kitchen, Exercise Room, Bathroom 2
  • Interior Features: Bar, Bathroom - Walk-In Shower, Bathroom - Tub Shower, Built-Ins, Carpet, Combination Kitchen/Dining, Crown Moldings, Dining Area, Floor Plan - Open, Family Room Off Kitchen, Kitchen - Gourmet, Kitchen - Island, Upgraded Countertops, Walk-in Closet(s), Wet/Dry Bar, Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Gas/Propane, Mantel(s)
  • Appliances: Cooktop - Down Draft, Dishwasher, Refrigerator, Stainless Steel Appliances, Washer - Front Loading, Dryer - Front Loading, Built-In Microwave, Disposal, Exhaust Fan, Oven - Wall, Water Heater
  • Flooring: Hardwood, Carpet, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Upper 2 - Full Baths: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 1
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 3
  • Bedrooms-Up2: 2

Other Rooms

  • Laundry: Dryer In Unit, Washer In Unit, Upper Floor

Exterior

  • Exterior Features: BBQ Grill, Exterior Lighting, Sidewalks, Extensive Hardscape
  • Porch/Patio/Deck: Porch(es), Deck(s), Balcony

Parking

  • Total Spaces: 2
  • Parking Features: Concrete Driveway, Electric Vehicle Charging Station(s)
  • Parking Type: Driveway

Location

  • Municipality: Annapolis
  • County: ANNE ARUNDEL
  • Subdivision: EASTPORT
  • Cross Streets: Fifth Street
  • Driving Directions: Take a left off of Compromise Street/Sixth Street onto Chesapeake Avenue.
  • Direction Faces: West
  • Location Details: Corner Lot/Unit
  • City Limits: Yes

School Information

  • School District: Anne Arundel County Public Schools
  • Elementary School: Eastport
  • Middle School: Annapolis
  • High School: Annapolis

Community

  • Pets Allowed: Yes
  • Pets: No Pet Restrictions

Heating & Cooling

  • Cooling Type: Other
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric, Natural Gas
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Natural Gas Available, Sewer Available, Water Available, Cable TV Available

Structural Information

  • Architectural Style: Coastal
  • Structure Type: Detached
  • Construction: Wood Siding
  • Foundation: Slab
  • Roof: Asphalt
  • Walls/Ceilings: 9'+ Ceilings
  • Windows: Double Pane, Energy Efficient, ENERGY STAR Qualified, Replacement, Screens
  • Stories/Levels: 4
  • Stories Description: Main, Upper 1, Upper 2
  • Square Feet: 2,077
  • Sq. Ft. Source: Assessor
  • Living Area: 2,077 Sq. Ft.
  • Finished Above Grnd: 2,077 Sq. Ft.
  • Year Built: 1979
  • Year Built Source: Assessor
  • Property Condition: Excellent

Additional Structures

  • Other Structures: Shed

Lot Features

  • Property View: Street, Trees/Woods
  • Lot Size (Acres): 0.14
  • Lot Size (Sq. Ft.): 6,008
  • Lot Size Source: Assessor
  • Zoning: R
  • Lot Description: Corner, Front Yard, Landscaping, Level

Financial Considerations

  • Price Per Sq. Ft.: $719.79
  • Assessment Year: 2026
  • City/TownTax: $8,086
  • City/TownTax Freq: Annually
  • County Tax: $7,616
  • County Tax Freq: Annually
  • Tax w/Assessment: $1,257,300
  • Tax Amount: $15,702
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 2077

Disclosures and Reports

  • Ownership: Fee Simple
  • Inclusions: Electric Vehicle Charger, Framed TV with speaker in LR, TV on outside front porch, TV in Kitchen, Gas Grill on Deck
  • Lot Number: A1
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 417 Chesapeake Ave —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 417 Chesapeake Ave

School District:Anne Arundel County Public Schools
NameGradesDistance
Eastport Elementary School
420 Fifth Street, Annapolis, MD 21403
PK-50.1 mi
Annapolis Middle School
1399 Forest Drive, Annapolis, MD 21403
6-81.8 mi
Annapolis High School
2700 Riva Road, Annapolis, MD 21401
9-124.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 417 Chesapeake Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/09/2026
Listed
$1,495,000
39.39%
MLS
2/24/2023
Sold
$1,072,500
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 417 Chesapeake Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$12,634
14%
$1,095,767
17%
2023
$11,096
—
$934,233
21%
2023
$11,096
4%
$772,700
2%
2022
$10,631
6%
$754,500
2%
2018
$9,989
2%
$736,300
3%
2021
$9,779
1%
$718,100
—
2020
$9,714
2%
$718,100
—
2019
$9,517
8%
$718,100
—
2018
$8,841
5%
$719,700
7%
2017
$8,452
5%
$674,067
7%
2016
$8,064
4%
$628,433
8%
2015
$7,722
-7%
$582,800
-6%
2014
$8,262
—
$620,700
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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417 Chesapeake Avenue, Annapolis, MD 21403 (MLS# MDAA2144320) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 417 Chesapeake Avenue is currently listed for $1,495,000 and was received on May 09, 2026. This property is listed by Barbara Birkbeck White from our Annapolis Church Circle Office.Want to learn more about 417 Chesapeake Avenue? Do you have questions about finding other Single Family real estate for sale in Annapolis? You can browse all Annapolis real estate or contact a Coldwell Banker agent to request more information.

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