Old Port Real Estate

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Browse real estate for sale in Portland's Old Port. Contact Benchmark Real Estate | Maine with questions or to schedule a private showing. Sign up to save your favorite Old Port listings and custom searches, and we'll email you when similar properties become available.

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Old Port Homes For Sale in Portland Maine

Old Port, in many ways, feels like quintessential Portland, Maine: cobblestone streets, a bustling waterfront, and charming bistros pepper this iconic, central hub. Old Port attracts those looking for a lively, picturesque place to live, in the heart of the city. To the south you’ll find a working waterfront, and piers filled with lobstering boats, restaurants, and shops. Old Port has become a center for the creative, tourist, and hospitality economy. Old Port is host to a rich blend of arts, entrepreneurship, and local businesses, making it both a dynamic and serene place to live all season long.

The Old Port district is known for its 19th-century brick buildings, and traditional brownstones with antique iron detailing. However, if you prefer a more modern view of the ocean, Old Port has a variety of newer builds. If you’re looking for views over acreage, and prefer to be steps away from unique boutiques, acclaimed restaurants, and lively bars, this is the neighborhood for you. The area’s proximity to nearby neighborhoods like Bayside, East Bayside, Munjoy Hill, and the West End further enhances its appeal, offering easy access to diverse experiences and a sense of community.

Top 10

  1. Walking Around Old Port District – Commercial Street will give you a sense of the working waterfront to the south, and many shops and restaurants on the city-side. Meander around Wharf and Exchange Streets to experience the cobblestone, boutiques, and vibrant nightlife (leave the heels at home for this area!).
  2. Harbor Fish Market – Located across from The Porthole, this iconic market (that has been a fish market since the 1800’s) is located directly on the Custom House Wharf, is as close to buying off the boat as you can get. 
  3. A Self-Guided Underground Railroad Walking Tour – Take this walking tour of 13 sites in downtown Portland, highlighting the stories of Black Mainers and the Underground Railroad in the 19th century. Start at Lincoln Park or the Maine State Pier.
  4. Maine Souvenir Shop – Located on the corner of Exchange Street and Fore Street this ‘souvenir shop’ is more of a must see gallery where you can grab goods unique to Maine and made by local artists. 
  5. Casco Bay Ferry – The best views of Old Port are from the water. Take a scenic ferry ride to the Casco Bay Islands, like Peaks Island or Great Diamond Island. These islands offer walking trails, quaint villages, and beautiful views of the bay. Some other vessels we recommend looking into are: Lucky Catch, Discovery Tours, or the Portland Schooner Co for a unique tour aboard a wooden Windjammer.
  6. Enjoy the Art Galleries – Portland Art Gallery and Greenhut Galleries exhibit some of Maine’s finest contemporary artists. 
  7. Shop world-famous artisans and boutiques – From well-known New England-brands like Seabags and Simon Pearce walk along Exchange, Middle, and Fore Streets to take in all the talent of our local artists and crafters.
  8. Reset and refuel at one of the many bars and restaurants – Old Port is known for its array of dining options. Seafood classics like Scales, Street & Co, Fore Street, and Luke’s Lobster aren’t to be missed.
  9. Bike & Pedestrian Friendly –  With one of the best walking scores in the state, walk anywhere within twenty minutes, or hop on a bike from Summer Feet Cycle if you’re ready to explore hidden coastal paths beyond the city center.
  10. Keep Researching! – There’s never a shortage of things to do in Old Port. Check out Portlandoldport.com to see what’s happening in town, from live music to road races and everything in between.

Pocket Neighborhood: India Street Neighborhood

The India Street Neighborhood is a historic area known for its eclectic mix of residential apartments, hotels, and local businesses. This small “pocket” neighborhood is nestled between Congress, Mountfort, Thames, and Franklin streets, thus neighbor to the East End and Old Port. The location of the India Street neighborhood naturally makes it a hub of activity and culture. The area boasts a rich history, with landmarks such as the Abyssinian Meeting House, one of the oldest African American churches in the country. The India Street Neighborhood Association plays a crucial role in preserving the charm and community spirit of the neighborhood, while also fostering local business development and maintaining the historic essence of the area.

Top 10

  1. Black Elephant Hostel – A cozy, affordable hostel with a laid-back vibe, perfect for travelers looking for a comfortable stay.
  2. Tomaso's Canteen – A beloved neighborhood bar and eatery serving hearty comfort food and local brews.
  3. Duck Fat – Famous for its hand-cut fries cooked in duck fat, this popular eatery offers indulgent dishes and gourmet flavors.
  4. Abyssinian Meeting House – One of the oldest African American churches in the U.S., rich with cultural and historical significance.
  5. Maine Narrow Gauge Railroad Co. & Museum – Ride the historic two-foot gauge trains along the bay.
  6. Cloudport CoWorking Space – A modern, shared workspace ideal for freelancers, entrepreneurs, and remote workers. Now with two locations in the area.
  7. Dok Mali – A modern twist on East Asian cuisine, using the freshest ingredients, in a great location with big windows, perfect for people watching.
  8. The Honey Paw – An inventive noodle bar with a focus on Asian-inspired dishes.
  9. The Eastern Cemetery – Opened in 1668, this is the city's oldest historic site. It has more than 4,000 marked graves with an estimated further 3,000 burials in unmarked plots. The resting place of Portland's earliest settlers, Eastern Cemetery remained active until the 1860's.
  10. Micucci’s Grocery Co. – Miccuci Wholesale has been serving the restaurant industry for over 50 years. However, this traditional market on India Street offers a selection of their renowned meats, cheeses, artisanal pastas, and other Italian products for local retail customers.
  11. World Headquarters – This emerging area is home to several corporate headquarters from WEX, Covetrus, Sun-life, Tilson and more.

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