215 Chester Ave, Annapolis, MD 21403 | Pending

Back to Search    

Off-Market Call for Pricing

Call for Pricing
  • (0)
  • 4 Bedrooms
  • 4 Bathrooms
  • 3,421 Sq Ft
  • 5,960 Sq Ft

Description

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.

View Map
View Map

Amenities

Garage
Pool
Garden
Security System
Internet
Telephone
Heating
Fireplace
Balcony & Patio
TV / Cable
Laundry
Hardwood Floors
Spa
Air Conditioning
Solar Power
Floor Plan
Great Views
Natural Light
Quiet
Water View
Elevator
Guest Unit(s)
Furnished
220 Volt

Income

Rental Units


The income description goes here to explain

Expenses

Property Details

List Price $1,799,000
Property Type Single Family Homes
Usable Sqft 3,421
Number of Stories 0 stories
Parking Spots 2 spots
Year Built 2003
Last Sold Unknown
Sold Price Unknown
APN # 020600002515800
MLS # MDAA2128708
Property ID 295075365
Lot Sqft 5,960
Zoning RESIDENTIAL
Days on Market 107
Original List Price Unknown
Applicances 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%
Date Updated January 31, 2026
Date Created October 18, 2025

Listing Provided By

Janet L Craig an agent of . Lic #635272


© 2026 Copyright BRIGHT, All Rights Reserved

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which participates, and is provided by BRIGHT through a licensing agreement.

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller.

This home sale information is not to be construed as an appraisal and may not be used as such for any purpose.

BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.

Information Deemed Reliable But Not Guaranteed



Data last updated: February 02, 2026.
$
%
Compare rates
%
Your payment

per month
Estimated payment
Loan amount
Down payment
Interest rate
Loan term
Taxes & insurance included?
Property tax
Homeowner's insurance
HOA dues

Payment Breakdown

Your payment

per month

Amortization

Principal vs. interest



Our powerful mortgage calculator tools helps you estimate your potential mortgage payment on the purchase of a property. Use our tool to find the ideal combination of interest rates, downpayment and real estate purchase price to see the payment that best suits you. Please consult a licensed loan officer to be pre-approved for financing options.

Real Estate Broker
Santa Monica, CA
WE ARE REALTY PARTNER
5
7 Reviews
  • 78Sales
  • 13Listings
  • 36Posts
Love This Property

people love this property

Love This Property