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21 Boucher Pl, Annapolis image
21 Boucher Pl, Annapolis $749,999

Welcome to this beautifully maintained townhome in Eastport’s sought-after Boucher Place community, where timeless design meets effortless, low-maintenance living. Built ...

  • 3 Beds
  • 4 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

1105 Van Buren St, Annapolis image
1105 Van Buren St, Annapolis $599,000

Offer deadline Monday 27th at 5:00PM Seller reserves right to accept offer at anytime. Welcome to Colony Hills, one of Eastport's most coveted neighborhoods, where charm,...

  • 3 Beds
  • 2 Baths
Courtesy of Compass

Listing courtesy of Compass. Contact: (410) 429-7425

1107 Brashears Street, Annapolis image
1107 Brashears Street, Annapolis $800,000

Discover the perfect blend of Annapolis charm and contemporary luxury at 1107 Brashears Street in desirable Eastport. Meticulously transformed and fully remodeled, this t...

  • 5 Beds
  • 2 Baths
Courtesy of Engel & Volkers Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: .

4 Kelly Court, Annapolis image
4 Kelly Court, Annapolis $1,250,000

Enjoy living in the heart of Eastport, where charming streets, waterfront parks, and a vibrant dining scene create one of Annapolis' most coveted lifestyles. This invitin...

  • 3 Beds
  • 4 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

906 Creek Drive, Annapolis image
906 Creek Drive, Annapolis $6,200,000

An Eastport waterfront home located on Spa Creek set on a prominent .165-acre site once part of a historic city park, this property offers approximately 3000 above grade...

  • 4 Beds
  • 4 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

526 Sixth St, Annapolis image
526 Sixth St, Annapolis $1,795,000

A rare opportunity to own a beautifully reimagined residence in the heart of Eastport, where timeless architecture meets modern comfort. Rich in history and craftsmanship...

  • 3 Beds
  • 3 Baths
Courtesy of Engel & Volkers Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

1105 Boucher Ave, Annapolis image
1105 Boucher Ave, Annapolis $1,285,000

Nestled in the heart of Eastport, this thoughtfully designed 3-bedroom, 2.5-bath home offers the perfect combination of comfortable living, modern updates, and one of Ann...

  • 3 Beds
  • 3 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

219 Lockwood Ct, Annapolis image
219 Lockwood Ct, Annapolis $1,750,000

Nestled in the heart of Eastport, this stunning Craftsman-style home offers the perfect blend of timeless charm and modern luxury. Boasting 4 bedrooms and 4 full baths, t...

  • 4 Beds
  • 4 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 224-4999

140 Jefferson Street, Annapolis image
140 Jefferson Street, Annapolis $1,000,000

Open House Saturday 2-4PM & Sunday 12-2PM. Welcome to your own Eastport retreat, where the inviting outdoor living spaces set the stage for everything this exceptional ho...

  • 4 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

313 Washington Street, Annapolis image
313 Washington Street, Annapolis $2,965,000

Unparalleled excellence in design and attention to detail in the heart of Eastport. This elegant and inviting home is so tastefully designed that it fits right in with th...

  • 5 Beds
  • 6 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

1109 Boucher Avenue, Annapolis image
1109 Boucher Avenue, Annapolis $1,350,000

Living the Eastport lifestyle - This is what upscale, modern urban living is all about! It's an easy walk to downtown shops, restaurants and marinas from this centrally...

  • 4 Beds
  • 5 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

131 Eastern Avenue, Annapolis image
131 Eastern Avenue, Annapolis $900,000

Experience the pinnacle of Annapolis living in this expertly restored 1920s masterpiece. Situated in the sought-after Eastport peninsula, this residence offers a rare ble...

  • 2 Beds
  • 2 Baths
Courtesy of Keller Williams Flagship

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

1100 Bay Ridge Ave, Annapolis image
1100 Bay Ridge Ave, Annapolis $750,000

You’ve experienced Eastport. You’ve admired the effortless ease of its residents, and now you’re . Embrace that coveted, walkable, waterfront lifestyle. This enchanting, ...

  • 3 Beds
  • 2 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

1035 Boucher Avenue, Annapolis image
1035 Boucher Avenue, Annapolis $1,399,000

Welcome to Eastport, one of Annapolis most sought-after waterfront communities! This newer construction home offers the perfect blend of modern convenience, functional li...

  • 4 Beds
  • 4 Baths
Courtesy of Compass

Listing courtesy of Compass. Contact:

Selling Office: .

513 Fifth St, Annapolis image
513 Fifth St, Annapolis $845,000

An exceptional opportunity to embrace the coveted Eastport lifestyle while planning and permitting your future dream home. Situated on a generously sized lot in one of An...

  • 2 Beds
  • 1 Baths
Courtesy of Engel & Volkers Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

417 Chesapeake Avenue, Annapolis image
417 Chesapeake Avenue, Annapolis $1,380,000

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, ...

  • 3 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

1014 Wells Avenue, Annapolis image
1014 Wells Avenue, Annapolis $360,000

Welcome Home to Eastport. Walk to the Eastport Shopping center for breakfast or to downtown Annapolis for lunch or dinner. This cute 4-bedroom (egress in basement)1.5 b...

  • 4 Beds
  • 2 Baths
Courtesy of EXIT Spivey Professional Realty Co.

Listing courtesy of EXIT Spivey Professional Realty Co.. Contact:

Selling Office: .

200 Chesapeake Avenue, Annapolis image
200 Chesapeake Avenue, Annapolis $875,000

*** A must-see opportunity in the desirable Eastport Peninsula! This unique property features two attached dwellings in one, offering exceptional flexibility and income p...

  • 3 Beds
  • 3 Baths
Courtesy of Compass

Listing courtesy of Compass. Contact:

Selling Office: .

122 Chesapeake Avenue, Annapolis image
122 Chesapeake Avenue, Annapolis $2,275,000

Introducing 122 Chesapeake Avenue, a beautifully constructed Eastport residence offering refined coastal living with elevated design throughout. Built in 2014, this luxur...

  • 4 Beds
  • 5 Baths
Courtesy of Engel & Volkers Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: .

289 State Street Unit #4, Annapolis image
289 State Street Unit #4, Annapolis $3,000,000

A new standard of waterfront living unfolds at the South Annapolis Yacht Centre, a boutique enclave of just eleven luxury residences rising along the edge of Spa Creek wh...

  • 2 Beds
  • 3 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

912 Windsor Avenue, Annapolis image
912 Windsor Avenue, Annapolis $2,000,000

Welcome to 912 Windsor Ave — The only ground up new construction home that is move in ready within city limits located right in the heart of coveted Eastport, Annapolis! ...

  • 5 Beds
  • 5 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

1210 President St, Annapolis image
1210 President St, Annapolis $600,000 ▼

Welcome home to this thoughtfully redesigned home in Eastport just blocks from Spa Creek and minutes to downtown Annapolis. This beautifully updated 3-bedroom, 3-bath res...

  • 3 Beds
  • 3 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

217 Lockwood Ct, Annapolis image
217 Lockwood Ct, Annapolis $4,995,000

There are places where you visit the water, and there are places where the water becomes part of your everyday life. Perfectly positioned along the shores of Spa Creek i...

  • 5 Beds
  • 4 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

400 Chesapeake Avenue Unit #2-101, Annapolis image
400 Chesapeake Avenue Unit #2-101, Annapolis $1,915,000

Embrace the ease of true coastal living in this beautifully appointed home, ideally situated just a short stroll from the waterfront and the bustling center of Downtown A...

  • 3 Beds
  • 4 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

418 Chesapeake Ave, Annapolis image
418 Chesapeake Ave, Annapolis $825,000 ▼

Quintessential Eastport charm in this sought-after Lower Eastport location. A welcoming front porch invites you to enjoy the vibrant local lifestyle. Inside, the light-fi...

  • 2 Beds
  • 2 Baths
Courtesy of Engel & Volkers Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

712 Chesapeake Avenue, Annapolis image
712 Chesapeake Avenue, Annapolis $1,600,000

Perfectly positioned in the heart of Eastport, this outstanding turnkey residence captures the essence of the Annapolis lifestyle, where charming neighborhood streets, wa...

  • 4 Beds
  • 3 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

1116 Bay Ridge Avenue, Annapolis image
1116 Bay Ridge Avenue, Annapolis $835,000

**Driveway parking in rear off of Jackson St.** This beautifully reimagined residence at 1116 Bay Ridge Avenue offers a sophisticated blend of classic Annapolis charm an...

  • 4 Beds
  • 3 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: .

148 Jefferson Street, Annapolis image
148 Jefferson Street, Annapolis $875,000

Brand New Construction Completed and ready for move in! Price reduction and the home is ready for its very first owner. Perfectly positioned in Eastport, Annapolis, jus...

  • 5 Beds
  • 3 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

312 Adams St, Annapolis image
312 Adams St, Annapolis $635,000 ▼

Great Opportunity! Prime Location!! Bring your ideas and imagination and transform this Eastport home into a gem! The current floorplan is 2 bedrooms and 1 bath with la...

  • 2 Beds
  • 1 Baths
Courtesy of Keller Williams Select Realtors of Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact: 4109724000

422 First St, Annapolis image
422 First St, Annapolis $790,000 ▼

Welcome to Eastport—just steps from downtown Annapolis. This charming duplex with rare two-car off-street parking offers the perfect blend of convenience, and coastal liv...

  • 2 Beds
  • 2 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

7056 Bembe Beach Road, Annapolis image
7056 Bembe Beach Road, Annapolis $655,000

Escape to coastal serenity at 7056 Bembe Beach Road, a beautifully maintained rancher offering the perfect blend of quiet, private living and premier access to the Annapo...

  • 3 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

219 Lockwood Court, Annapolis image
219 Lockwood Court, Annapolis $2,595,000

Experience the very best of the Eastport lifestyle, where sweeping views of Spa Creek, Historic Annapolis, and the Annapolis Harbor create an ever-changing backdrop to da...

  • 4 Beds
  • 5 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

818 Boucher Avenue, Annapolis image
818 Boucher Avenue, Annapolis $870,000

Welcome to 818 Boucher Avenue in coveted Eastport—an exceptional opportunity to create your dream home in one of Annapolis’ most sought-after waterfront communities. Perf...

  • 2 Beds
  • 1 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

619 Second St, Annapolis image
619 Second St, Annapolis $1,549,000 ▼

This exceptional 4 bedroom, 2 full baths, 2 half bath Coastal Contemporary residence captures the essence of Eastport living, where walkability, water access, and a vibra...

  • 4 Beds
  • 4 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

513 Horn Point Drive, Annapolis image
513 Horn Point Drive, Annapolis $3,310,000

Exceptional Waterfront and Beachfront living on Horn Point in coveted Eastport. Launch your kayak or SUP after morning coffee, and watch the sailboat races from your deck...

  • 4 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

820 Bay Ridge Ave, Annapolis image
820 Bay Ridge Ave, Annapolis — Sailor's Quay $1,875,000

An exceptional blend of timeless craftsmanship, thoughtful customization, and coastal elegance, 820 Bay Ridge Avenue offers over 4,000 square feet of beautifully finished...

  • 4 Beds
  • 5 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

1019 President St, Annapolis image
1019 President St, Annapolis $390,000 ▼

* Price Drop! Don't miss out on this beautiful fully updated Eastport home for less than $400k! * Welcome to 1019 President St in the heart of Eastport—where charm, spac...

  • 3 Beds
  • 2 Baths
Courtesy of CENTURY 21 New Millennium

Listing courtesy of CENTURY 21 New Millennium. Contact: 3015198100

152 Jefferson St, Annapolis image
152 Jefferson St, Annapolis $775,000 ▼

BEAUTIFULLY RENOVATED EASTPORT GEM with MODERN COASTAL FINISHES! Perfect for a Primary Residence, 2nd Home or Rental Investment! ABOUT THE HOME: 3 levels of luxury livi...

  • 4 Beds
  • 4 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

287 State Street Unit #2, Annapolis image
287 State Street Unit #2, Annapolis $5,950,000

South Annapolis Yacht Center is located on Spa Creek overlooking the beautiful skyline of Historic Annapolis. This award winning residence features an elegant interior de...

  • 3 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

400 Jefferson St, Annapolis image
400 Jefferson St, Annapolis $1,950,000 ▼

PRICE REDUCED - MOTIVATED SELLER- Nestled in the heart of historic Eastport Annapolis, this coastal craftsman has been extensively remodeled, offering a perfect blend of ...

  • 4 Beds
  • 4 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

1106 Brashears Street, Annapolis image
1106 Brashears Street, Annapolis $435,000

Enjoy the ease of single-level living with a functional layout, while also benefiting from exceptional expansion potential—build up, build out, or create the outdoor spac...

  • 3 Beds
  • 2 Baths
Courtesy of Next Step Realty, LLC.

Listing courtesy of Next Step Realty, LLC.. Contact:

Selling Office: .

1007 Park Avenue, Annapolis image
1007 Park Avenue, Annapolis $1,057,600

Experience the Eastport Lifestyle in a Beautifully Rebuilt Home Don’t miss this exceptional opportunity — a previous contract fell through due to circumstances beyond th...

  • 3 Beds
  • 4 Baths
Courtesy of Keller Williams Select Realtors of Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

Selling Office: .

320 Chester Avenue, Annapolis image
320 Chester Avenue, Annapolis $725,000

Rare opportunity to own a charming 2-unit building in the heart of Eastport, offering water views from both units. Each residence features its own private entrance and de...

  • 2 Beds
  • 2 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: .

422 Third Street, Annapolis image
422 Third Street, Annapolis $2,800,000

Simultaneously Listed and SOLD

  • 4 Beds
  • 4 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: .

215 Chester Avenue, Annapolis image
215 Chester Avenue, Annapolis $1,730,000

EXCITING PRICE IMPROVEMENT! SELLER HAS REDUCED THE PRICE-DON'T MISS THIS GREAT OPPORTUNITY. Immerse yourself in the quintessential Eastport lifestyle with this invitin...

  • 4 Beds
  • 4 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

1004 Moss Haven Court, Annapolis image
1004 Moss Haven Court, Annapolis $2,375,000

There is nothing else in Eastport like this beautiful, one floor living, attached garage, home with 4 bedrooms, 3 baths, large finished lower level and separate guest hou...

  • 4 Beds
  • 3 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

1019 President Street, Annapolis image
1019 President Street, Annapolis $235,000

Welcome to 1019 President Street, one of the most affordable opportunities in Annapolis and a great option for both owner-occupants and investors. This well-located prope...

  • 2 Beds
  • 1 Baths
Courtesy of Berkshire Hathaway HomeServices Homesale Realty

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

Selling Office: .

3 Chester Avenue, Annapolis image
3 Chester Avenue, Annapolis $1,660,000

Step into the heart of Eastport, where charm and convenience meet in this beautifully renovated Cape Cod. Just a short stroll from the water’s edge and downtown Annapolis...

  • 3 Beds
  • 3 Baths
Courtesy of Keller Williams Select Realtors of Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

Selling Office: .

105 Griscom Square Way, Annapolis image
105 Griscom Square Way, Annapolis $995,000

Welcome to Eastport Estates at Griscom Square, a brand-new construction community of just 11 luxury single-family homes, located within one mile of downtown Eastport! Eac...

  • 4 Beds
  • 4 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

27 Jeremys Way, Annapolis image
27 Jeremys Way, Annapolis $820,000

Nestled in Eastport’s coveted historic district, 27 Jeremys Way is a rarely available offering on the market and one of the original homes from Murphy’s Row—a surviving r...

  • 2 Beds
  • 2 Baths
Courtesy of Redfin Corp

Listing courtesy of Redfin Corp. Contact:

Selling Office: .

Eastport Real Estate & Homes

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Eastport, Annapolis MD. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

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