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$1,799,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,720 Sq. Ft.
  • 2 Car Garage
  • Updated 4 days ago

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

Sunday 1/18 1:00 PM - 3:00 PM

215 Chester Avenue,Annapolis, MD 21403

215 Chester AvenueAnnapolisMD21403

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EXCITING PRICE IMPROVEMENT! SELLER HAS REDUCED THE PRICE-DON'T MISS THIS GREAT OPPORTUNITY. Immerse yourself in the quintessential Eastport lifestyle with this inviting Craftsman-style residence, ideally located just moments from the water access at Davis Park and the vibrant offerings of Eastport and downtown Annapolis. This beautifully maintained home spans three thoughtfully designed levels and features four bedrooms, three and a half baths, an elevator, and comfortable sitting areas on every floor. Highlights include a gourmet kitchen, warm living spaces with a fireplace, rich wood flooring, a generous dining area, and a reverse floor plan that captures light, views, and a relaxed coastal feel-making every day feel like a getaway. The entry level is perfect for hosting family and friends, offering three bedrooms, including a private ensuite with direct access to the deck and hot tub, plus two additional bedrooms served by a hall bath. The second level is devoted to the primary retreat, featuring an open sitting area overlooking the level below, a spacious bedroom, a private deck with peaceful backyard views, and a luxurious spa-inspired bath. The top level serves as the heart of the home, complete with an expansive partially covered balcony where you can enjoy seasonal glimpses of Back Creek from an exceptionally private setting. Outdoor spaces are equally impressive, with a welcoming front porch and a large, fenced rear yard featuring a deck, hot tub, and pergola-ideal for entertaining, grilling, or simply soaking in the Eastport vibe. A detached garage with driveway provides rare and valuable off-street parking for multiple vehicles. Above the garage, a finished space with a separate entrance offers endless flexibility for guests, a home office, studio, or rental opportunity. This property also presents excellent potential as a VRBO or Airbnb, offering year-round income possibilities in one of Annapolis's most sought-after neighborhoods. Buyer should check current licensing regulations for Annapolis. Enjoy leisurely strolls through Eastport's artistic, maritime streets to acclaimed restaurants, pubs, and charming street-end parks, one is right next door. Downtown Annapolis and the Naval Academy are just steps away via the Spa Creek drawbridge or a quick ride on the water taxi. From here, you're also close to premier cruising and fishing waters, with easy access to destinations like Baltimore's Inner Harbor, St. Michaels, Oxford, and Solomon's Island. Conveniently located approximately five miles from Routes 50 and 97, with direct access to Baltimore, BWI, Fort Meade/NSA, and Washington, DC, this home offers the perfect blend of coastal charm, walkable convenience, and sophisticated living. Welcome to Eastport living at its best.

Full Property Details for 215 Chester Ave

General

  • Price: $1,799,000
  • Taxes: $16,857 (2024)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDAA2128708
  • Updated: 1/11/2026
  • Added to Site: 89 day(s) ago

Interior

  • Interior Features: Breakfast Area, Built-Ins, Ceiling Fan(s), Combination Dining/Living, Combination Kitchen/Dining, Combination Kitchen/Living, Dining Area, Elevator, Entry Level Bedroom, Exposed Beams, Family Room Off Kitchen, Floor Plan - Open, Kitchen - Eat-In, Kitchen - Gourmet, Primary Bath(s), Recessed Lighting, Sprinkler System, Upgraded Countertops, Window Treatments, Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Fireplace(s): Fireplace - Glass Doors, Gas/Propane, Stone, Electric
  • Appliances: Built-In Range, Commercial Range, Dishwasher, Disposal, Dryer, Microwave, Oven/Range - Gas, Range Hood, Refrigerator, Six Burner Stove, Stainless Steel Appliances, Washer, Water Heater - Tankless
  • Flooring: Hardwood, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Upper 2 - 1/2 Baths: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 1
  • Upper - 1/2 Baths: 1
  • Main Floor Baths: 2
  • Main - Full Baths: 2

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 1
  • Bedrooms Main & Up: 3

Other Rooms

  • Laundry: Main Floor

Additional Information

  • Spa: Yes
  • Security/Safety: Carbon Monoxide Detector(s), Security System, Smoke Detector, Sprinkler System - Indoor

Exterior

  • Exterior Features: Extensive Hardscape, Exterior Lighting, Hot Tub, Street Lights
  • Porch/Patio/Deck: Balconies- Multiple, Porch(es), Deck(s)

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 5
  • Parking Features: Concrete Driveway
  • Parking Type: Detached Garage, Driveway
  • Garage Description: Additional Storage Area, Garage - Front Entry, Garage Door Opener

Location

  • Municipality: Annapolis
  • County: ANNE ARUNDEL
  • Subdivision: EASTPORT
  • Driving Directions: Compromise St from downtown Annapolis into Eastport. Turn left onto Chester Ave. Home is on your right, next to Turner Park.
  • City Limits: Yes

School Information

  • School District: Anne Arundel County Public Schools

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Ceiling Fan(s), Central A/C, Programmable Thermostat, Zoned
  • Cooling Fuel: Electric
  • Heating Type: Forced Air, Programmable Thermostat, Zoned
  • Heating Fuel: Natural Gas
  • Water Heater: Tankless, Natural Gas

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Dist. to Water: 1 Blocks

Structural Information

  • Architectural Style: Coastal, Craftsman
  • Structure Type: Detached
  • Model: Eastport Craftsman
  • Construction: Frame
  • Basement: Yes
  • Basement Desc.: Other
  • Foundation: Other
  • Walls/Ceilings: Beamed Ceilings, Vaulted Ceilings, Wood Ceilings
  • Elevator(s ): 1
  • Stories Description: Main, Upper 1, Upper 2
  • Square Feet: 3,720
  • Sq. Ft. Source: Assessor
  • Living Area: 3,421 Sq. Ft.
  • Finished Above Grnd: 3,122 Sq. Ft.
  • Finished Below Grnd: 299 Sq. Ft.
  • Year Built: 2003
  • Year Built Source: Assessor

Lot Features

  • Property View: Creek/Stream
  • Lot Size (Acres): 0.14
  • Lot Size (Sq. Ft.): 5,960
  • Lot Size Source: Assessor
  • Zoning: RESIDENTIAL
  • Lot Description: Front Yard, Landscaping, Level, Premium

Water Features

  • Water View: Yes
  • Navigable Water: Yes
  • Water Access: Yes
  • Water Access Desc: Canoe/Kayak, Fishing Allowed, Public Access, Swimming Allowed
  • Water Front Type: Creek/Stream
  • Water Front Name: Back Creek

Financial Considerations

  • Price Per Sq. Ft.: $576.23
  • Assessment Year: 2025
  • City/TownTax: $8,657
  • City/TownTax Freq: Annually
  • County Tax: $8,200
  • County Tax Freq: Annually
  • Tax w/Assessment: $1,346,533
  • Tax Amount: $16,857
  • Tax Year: 2024
  • Tax Total Finished Sq. Ft.: 3421

Disclosures and Reports

  • Ownership: Fee Simple
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 215 Chester Ave —

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NMLS#: 1598647

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NMLS#: 1598647

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Schools serving 215 Chester Ave

School District:Anne Arundel County Public Schools
NameGradesDistance
Eastport Elementary School
420 Fifth Street, Annapolis, MD 21403
PK-50.2 mi
Annapolis Middle School
1399 Forest Drive, Annapolis, MD 21403
6-82 mi
Annapolis High School
2700 Riva Road, Annapolis, MD 21401
9-124.7 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 215 Chester Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/13/2025
Price Reduced
$1,799,000
-5.07%
MLS
11/14/2025
Price Reduced
$1,895,000
-2.82%
MLS
10/19/2025
Listed
$1,950,000
11.43%
MLS
7/11/2024
Sold
$1,750,000
—
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 215 Chester Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$19,296
41%
$1,346,533
15%
2023
$13,675
—
$1,173,067
17%
2023
$13,675
3%
$999,600
6%
2022
$13,300
24%
$943,967
6%
2018
$10,700
-9%
$888,333
7%
2021
$11,741
6%
$832,700
4%
2020
$11,082
5%
$800,967
4%
2019
$10,579
10%
$769,233
4%
2018
$9,596
2%
$737,500
2%
2017
$9,426
2%
$721,667
2%
2016
$9,256
1%
$705,833
-8%
2015
$9,142
-17%
$763,900
-8%
2014
$11,010
—
$827,200
—
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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215 Chester Avenue, Annapolis, MD 21403 (MLS# MDAA2128708) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 215 Chester Avenue is currently listed for $1,799,000 and was received on October 19, 2025. This property is listed by Janet Craig from our Annapolis Church Circle Office.Want to learn more about 215 Chester 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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