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21 Chesapeake Ldg, Annapolis, MD 21403
21 Chesapeake Ldg, Annapolis, MD 21403
Sold for $1,549,000
21 Chesapeake Ldg, Annapolis, MD 21403
Sold for $1,549,000
21 Chesapeake Ldg, Annapolis, MD 21403
21 Chesapeake Ldg, Annapolis, MD 21403
21 Chesapeake Ldg, Annapolis, MD 21403
21 Chesapeake Ldg, Annapolis, MD 21403

21 Chesapeake Ldg Annapolis, MD 21403

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$1,549,000

CLOSED
Beds
4
Baths
4
Sqft
2,232
Year
1979
Close Date
Nov 25, 2025
Property Type
Residential
Sub Type
Per Square Foot
$694
Date Listed
Jun 26, 2025

Description of 21 Chesapeake Ldg, Annapolis, MD 21403

Listing details for 21 Chesapeake Ldg, Annapolis, MD 21403 : Spectacular Water View Home nestled at the tip of Eastport Peninsula between Spa Creek, Back Creek and the Severn River in the premiere gated community of Chesapeake Landing, with onsite Yacht Club and pool memberships available. 21 Chesapeake Landing embodies the epitome of Eastport’s waterfront lifestyle. The Maritime Republic of Eastport is a vibrant waterfront community deeply rooted in both sailboat racing and pleasure boating traditions. Residents treasure the walkable lifestyle, with more than 50 restaurants, pubs, boutique shops, and historic City Dock and Downtown Annapolis just steps away. This immaculately-maintained home has been thoughtfully designed with meticulous, high-level upgrades, resulting in a seamless blend of elegance, comfort, and timeless design. A private in-law, guest suite or entertainment room on the ground level adds to the homes versatility. On the main level, expansive sliding glass doors open onto one of three decks; an ideal setting for savoring water views, or simply relaxing with evening libations. It’s also a front-row seat for the 4th of July, New Year’s Eve fireworks displays and the annual Blue Angels Airshow. The daily parade of sail and power boats, regattas, navy vessels and pirate ships is a spectacular bonus that makes this home truly unique. At the heart of the home is a spectacular chef’s kitchen: An oversized center island invites casual gatherings, while custom cabinetry, complete with artful display nooks, add depth and functionality. Sleek stainless-steel appliances pair beautifully with the honed-granite countertops, to provide ample prep space for the most discerning gourmet. A private deck just off the kitchen is perfectly positioned for effortless outdoor grilling. The open-concept layout is both flexible and inviting. Island seating flows naturally into the adjacent dining area, which overlooks the living room and captures water views beyond. Rich, gleaming hardwood floors span the main, bedroom, and loft levels, adding warmth and sophistication throughout. The living room is a true retreat, enhanced by 9-foot ceilings and a gas fireplace that adds instant ambiance with the flip of a switch. Upstairs, wake up to enjoys water views of Annapolis Harbor and the Severn River. The graciously sized owner’s suite welcomes you with dramatic vaulted ceilings and abundant natural light. The recently renovated spa-inspired ensuite bath is a sanctuary in itself, featuring a glass-enclosed shower and soaking tub that doubles as a steam room complete with folding chairs for relaxation and the therapeutic benefits of a sauna. Dual vanities, high-end fixtures, and generous storage, all finished in calming, modern tones complete the experience. Two additional bedrooms offer versatility and comfort; ideal for guests, family, or as a dedicated art studio, home gym, or private home office. The ground-level living space adds even more flexibility. Featuring its’ own paver patio and private entrance, a full bath and a custom kitchenette—including a refrigerator, sink, microwave, built-in storage and neutral tile flooring. This area can be completely closed off from the rest of the home, making it a perfect in-law suite, private guest quarters or family entertainment area. Additional amenities include a one-car garage, an extra driveway parking space, a large paver patio, and the freedom to lock, leave, and travel with peace of mind. Outside your front door, the Eastport lifestyle unfolds. Take a leisurely stroll to local waterfront restaurants, pubs, and boutique shops. Catch a water taxi to historic downtown Annapolis, or launch your kayak or paddleboard from nearby Horn Point Beach Park. Eastport offers the charm of a coastal village with the energy of a thriving maritime hub, just across Spa Creek from the U.S. Naval Academy and all the culture, history, and amenities of downtown Annapolis! Don't Miss The Opportunity to Make This Your Home!
Listing Updated : 10-10-2026 at 6:55 PM EDT
Listing Provided By : Stephanie M Snyder, 4109729727, [email protected], Long & Foster Real Estate, Inc.

Properties displayed may be listed or sold by various participants in the MLS

Source :

Bright MLS, MLS#: MDAA2117644

What's this home worth?

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Your home value estimate
$1.13M – $1.88M
Exact number$2,845,000

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What's this home worth?

National portals guess with an algorithm. We price it from actual closed sales on your street.

Your home value estimate
$1.13M – $1.88M
Exact number$2,845,000

Want an exact number? Use an Agent, not an algorithm.

Is this your home?

Claim it to unlock a private owner dashboard, track your equity, and get a free monthly value report.

Property History

DateEventPrice
11/25/2025
Sold
$1,549,000
$694/sqft
Source:Bright MLS #MDAA2117644
6/26/2025
Listed for sale
—
Source:Bright MLS #MDAA2117644

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What's this home worth?

National portals guess with an algorithm. We price it from actual closed sales on your street.

Your home value estimate
$1.13M – $1.88M
Exact number$2,845,000

Want an exact number? Use an Agent, not an algorithm.

Is this your home?

Claim it to unlock a private owner dashboard, track your equity, and get a free monthly value report.

Comments

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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, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information 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 the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc.
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