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$799,900
2 Beds ⋅ 2 Baths
Welcome to 127 Valley Avenue on beautiful Great Diamond Island, a private and peaceful retreat in the heart of Casco Bay. Set on a landscaped 0.28-acre wooded lot, this fully furnished, move-in ready home offers the perfect blend of modern updates and island charm, just a scenic 20-minute ferry ride from Portland. This thoughtfully remodeled 1,267-square-foot home features 2 bedrooms, 2 full bathrooms, a dedicated office, and a versatile bonus room. The updated kitchen showcases granite countertops, all new appliances, and a built-in bar complete with a mini fridge and keg refrigerator, creating an ideal space for entertaining. Enjoy the changing seasons from the enclosed wraparound porch, or cozy up by the propane fireplace on cooler evenings. Extensive improvements include five newly installed heat pumps, upgraded insulation, a new well, a new septic system, and thoughtful storage enhancements. Outside, enjoy beautifully maintained gardens, a self-watering vegetable garden, outdoor shower, hot tub, and additional storage building--perfect for embracing the relaxed island lifestyle. Great Diamond Island offers tranquil beaches, scenic walking paths, two island restaurants, and a relaxed coastal lifestyle just minutes from Portland's shopping, dining, airport, and rail service. Whether you're seeking a seasonal getaway or a nearly year-round island residence, this turnkey property offers an exceptional opportunity to enjoy the best of Maine island living.

127 Valley Ave, Portland

Listing courtesy of Harborview Properties, Inc..

$589,000
3 Beds ⋅ 3 Baths
Nestled on a spacious private lot, this distinctive contemporary home offers an exceptional blend of privacy, flexibility, and character. Beautifully landscaped grounds feature mature plantings, attractive stonework, multiple outbuildings, expansive outdoor living areas, and a hot tub that conveys in as-is condition--creating a peaceful setting for relaxing or entertaining. Operational solar panels help improve energy efficiency, while a generator hookup adds convenience and peace of mind. Inside, the open-concept first floor is warm and inviting, showcasing wood flooring throughout the living room, dining area, and spacious kitchen. A first-floor bedroom, full bath with shower, and laundry area provide the convenience of one-level living. The second floor offers a versatile layout with two flexible bonus spaces ideal for a home office, sitting room, hobby area, or guest accommodations. A spacious bathroom features a soaking tub, and one of the bedrooms opens directly onto a private deck, offering a quiet place to unwind. The third floor is home to a bright, airy bedroom surrounded by windows that fill the space with natural light, along with a convenient half bath. With its unique contemporary design, adaptable floor plan, energy-efficient features, and exceptional outdoor amenities, this one-of-a-kind property presents a rare opportunity to enjoy the privacy and natural beauty of Maine living.

238 Brackett Ave, Portland

Listing courtesy of Keller Williams Realty.

$945,000
4 Beds ⋅ 3 Baths
From its commanding position high on the lot, this impressive custom Colonial in Portland's desirable Stroudwater neighborhood offers an exceptional combination of space, convenience, and value. Set on nearly ½ acre with mature landscaping, lovely lawns, and an expansive backyard, the property provides privacy, sunshine, and room to enjoy the outdoors. Built in 2003, the home offers 3,391± SF of thoughtfully designed living space. The first floor features a well-appointed eat-in kitchen with island, abundant cabinetry, and space for casual dining. The kitchen flows seamlessly into the living areas, creating an ideal setting for everyday living and entertaining. A formal dining room, spacious front-to-back living room with fireplace, and convenient half bath complete the main level. The second floor offers 4 bedrooms, 2 full baths, and a dedicated laundry room. The oversized primary suite serves as a true retreat with a large walk-in closet and luxurious private bath. Generously sized secondary bedrooms provide flexibility for family, guests, or home office space. The walkout lower level is partially framed and ready for completion, offering outstanding potential for a family room, fitness area, home theater, guest suite, or additional workspace. A rare 3-car attached garage provides ample room for vehicles, storage, hobbies, and outdoor gear. Nature lovers will appreciate nearby access to the Stroudwater and Fore River trail systems, connecting miles of walking paths and protected natural areas. Located just minutes from downtown Portland, Portland International Jetport, I-295, I-95, shopping, dining, and employment centers, this is an ideal home for commuters, travelers, and anyone seeking substantial square footage in one of Southern Maine's most convenient locations.

58 Tide Mill Rd, Portland

Listing courtesy of Benchmark Real Estate.

$1,450,000
6 Beds ⋅ 5 Baths
141 William Street is a stately John Calvin Stevens Greek Revival combining refined period detail with thoughtful modern updates. Spanning over 6,000 sq ft, this 6-bedroom, 4.5-bath residence offers a generous, traditional layout ideal for entertaining or for those who prefer distinct, separate living spaces. A gracious foyer opens to an expansive formal living room anchored by a central fireplace and a stunning dining room with paneled wainscoting and a wood-burning fireplace. A large, well-appointed pantry leads to a magnificent kitchen completely renovated in 2023, featuring custom cabinetry, stone counters, a tasteful tile backsplash with custom mosaic, and a professional-grade Viking appliance package. The kitchen flows to a sunken back family room and private yard, and connects to a back hallway and rear staircase. The second floor houses four generous bedrooms, including the primary suite, linked by a wide, open hallway. The third floor offers two additional bedrooms, an office, a full bath, and a large cedar closet. The finished basement is an entertainer's dream with a full bar, pool-table space, lounge area, plus a dedicated room ideal for a home gym with an infrared sauna. Lovingly maintained, recent improvements include a new roof, new heating system, added heat pumps, significant electrical upgrades and more, an exceptional blend of historic charm and modern comfort. Located just down the street from the new, gorgeous Crewe Center at University of Southern Maine. Also conveniently located about half a mile from Deering Oaks Park where you can find the local farmers market, as well as Fitzpatrick Stadium for the Portland Hearts Of Pine soccer games, Hadlock Field for the Seadogs games and Portland Expo for the Red Claws basketball games!

141 William St, Portland

Listing courtesy of Portside Real Estate Group.

$1,275,000
3 Beds ⋅ 2 Baths
Located on a corner lot on coveted Munjoy Hill, 42 Montreal Street is an impeccably renovated, single family house with three bedrooms and two bathrooms. This high quality renovation features copper flashing and downspouts, cedar clapboard siding, a red cedar shingle roof, and a meticulously rebuilt historic cupola. Water views and sweeping vistas of Casco Bay create a stunning backdrop, while the cupola provides a perfect perch for watching summer fireworks over the harbor. Inside, hardwood floors and thoughtfully preserved architectural details blend timeless character with everyday comfort. Outside, a glorious private garden filled with roses and perennial plantings offers exceptional privacy and beauty, creating an extraordinary urban oasis. Multiple outdoor living areas invite entertaining, relaxing, and enjoying Maine's seasons. This absolutely charming mansard-roof cottage enjoys a quiet, private pocket of Portland's East End, just steps from parks, trails, restaurants, shops, and the waterfront. Walk to tennis courts, a boat launch, and a sandy beach, embracing the very best of the East End lifestyle. Beautifully cared for inside and out, this special property offers a rare opportunity to enjoy Portland's vibrant coastal lifestyle from one of Munjoy Hill's most desirable locations.

42 Montreal St, Portland

Listing courtesy of Town & Shore Real Estate. 207-773-0262
$2,100,000
7 Beds ⋅ 6 Baths
In real estate, it is often said that location is everything. The challenge, of course, is that the best locations were claimed long ago. For most buyers, that means finding a property with potential and transforming it into something special. Here, that work has already been done. Perched in one of Portland's most coveted locations overlooking the Western Promenade, this extraordinary residence combines an irreplaceable setting with over fifteen years of thoughtful renovation and restoration. The result is a seamless blend of historic character and modern comfort, creating a home that honors its past while meeting the needs of contemporary living. Imagine ending your day on the porch, overlooking the park and enjoying spectacular sunsets. Open the windows and doors and allow the ocean breezes to flow throughout the home. There is a feeling here that is difficult to describe and impossible to replicate--a sense of history, craftsmanship, and place that makes this property truly exceptional. Designed to be both grand and comfortable, the versatile floor plan offers spaces that can evolve to fit your lifestyle. The home features five bedrooms with A/C, four and a half baths, a stately library or office, formal living and dining rooms, a chef's kitchen, and a butler's pantry. Every room is enriched by extraordinary architectural details, including black walnut and quarter-sawn oak woodwork, crystal chandeliers, wainscoting, bay windows, hand-painted murals, leaded glass cabinetry, and stunning stained-glass windows. These remarkable materials and finishes were crafted by artisans whose work has stood the test of time. A private entrance and guest quarters on the third floor provide additional flexibility for extended family, guests, or creative living arrangements. Outside, lush gardens, gracious entrances, inviting porches, and seven off-street parking spaces further enhance the property's appeal--an uncommon luxury in this historic neighborhood.

261 Western Promenade, Portland

Listing courtesy of Roxanne York Real Estate.

$575,000
4 Beds ⋅ 2 Baths
Step into the perfect blend of timeless charm and modern convenience in this beautifully maintained 1919 Gambrel-style home on Presumpscot Street in Portland. Featuring 4 bedrooms and 2 bathrooms, this home features a thoughtfully designed layout with a first-floor bedroom, full bath, and laundry--ideal for single-level living or accommodating guests. The inviting farmer's porch welcomes you home and flows into a cozy living room filled with character and warmth. A designated dining room provides the perfect setting for gatherings, while the kitchen seamlessly combines classic charm with modern functionality. Throughout the home, you'll find a wonderful balance of original details and tasteful updates. Upstairs, three spacious bedrooms and a full bathroom provide comfortable living space for bedrooms, guests, or a home office setup. Enjoy abundant storage with separate full basements under both the original home and the addition. Outside, enjoy a beautifully landscaped, level 0.12-acre lot with open yard space perfect for gardening, entertaining, or simply relaxing. Conveniently located under 10 minutes from Portland's vibrant Old Port and downtown districts, this home offers easy access to local restaurants, shops, and waterfront attractions. Outdoor enthusiasts will appreciate the proximity to the Presumpscot River Preserve, Back Cove Trail, and miles of walking, running, and biking trails, along with nearby parks, golf courses, and recreational opportunities. A rare opportunity to own a piece of Portland history while enjoying the conveniences of modern living in one of Maine's most desirable cities.

64 Presumpscot St, Portland

Listing courtesy of Keller Williams Coastal and Lakes & Mountains Realty.

$1,100,000
2 Beds ⋅ 3 Baths
A breath of fresh air, a step above, one of a kind, welcome to 4 Oramel. Set on nearly an acre and a half and surrounded by protected land abutting parks and trails it is hard to believe you are just moments away from downtown Portland. Thoughtfully developed to match the natural landscape, the home seamlessly blends modern farmhouse with mid-century modern design throughout. Frenking Building Company is a design-forward building company specializing in high end finish carpentry with an approach rooted in simplicity. This 3 bedroom, 2.5 bathroom home surrounded by a gorgeous natural backdrop offers clean lines, natural materials and pallets, and a floor-plan that flows effortlessly inside and out. Stepping inside you will immediately be taken with the attention to detail in every aspect of the design and finish. Custom built cabinetry, simple yet sophisticated tile choices, natural woods throughout, incredible windows and doors, venetian plaster detail, and the incredible wrap around porch. If you have been searching for a truly special property with privacy that doesn't sacrifice convenience, where spaces are soaked in natural light, and where you can be close to nature, you will find it here.

4 Oramel Ave, Portland

Listing courtesy of Portside Real Estate Group.

$729,000
3 Beds ⋅ 3 Baths
Welcome to 495 Allen Avenue - a rare opportunity to own a versatile move-in-ready property in Portland's convenient North Deering neighborhood. This 2,200 sqft property includes the 2BD/2BA main house and a 1BD/1BA Accessory Dwelling Unit (ADU). The ADU offers multigenerational living, guest quarters, and potential for rental income. Outside, enjoy a spacious backyard ideal for entertaining, gardening, and relaxing during Maine summers, plus ample off-street parking. Conveniently located just minutes from Shaw's, Northgate Plaza, restaurants, coffee shops, and local favorite Lib's Dairy Treats, with downtown Portland and Falmouth only about 15 minutes away. Whether you're looking for extra space, income potential, or a smart investment in a prime Portland location, 495 Allen Avenue delivers opportunity and convenience.

495 Allen Ave, Portland

Listing courtesy of Elevate Maine Realty.

$945,000
5 Beds ⋅ 4 Baths
Nestled in the heart of Portland's highly sought-after West End, this exceptional property is sure to charm investors and those seeking multi-generational living in a city setting. Currently operating as a highly successful Airbnb, the next owner could continue to make income from one or both of the living spaces, or owner occupy and utilize the first floor unit as an in-law suite. The spacious primary home features 4 bedrooms plus an office and 3 full bathrooms across three floors. Thoughtfully updated, the main home features a custom kitchen and inviting living spaces where soaring cathedral ceilings, exposed wood beams, and skylights create an airy yet cozy atmosphere, filling the kitchen and living room with beautiful natural light and architectural charm. Other standout features include a custom antique bar, wainscoting along the main staircase with a beautifully preserved original banister, and a private deck with low maintenance composite decking. The first floor bedroom is currently used as a home studio office with its own full bathroom. The secondary one bedroom, one bath unit is an easy one level living set up, all on the first floor. The full basement is available for storage. Built in 1874 and offering 2,634 square feet of living space, this West End gem is made even more special by amenities rarely found in the city: a private courtyard perfect for relaxing or entertaining, space for a city garden, and coveted off-street parking. Just moments from Portland's renowned restaurants, shops, hospitals, and waterfront, this is a rare opportunity to own a piece of Portland history.

75 Carleton St, Portland

Listing courtesy of Maine Real Estate Co.

$999,900
2 Beds ⋅ 1 Baths
Here's your opportunity of a lifetime! This spectacular property is a truly rare offering with approximately 220 feet of ocean frontage overlooking Diamond Pass. Set well back from the road and perched along the shoreline, it captures sweeping, serene water views, sandy beach frontage (a rarity on the island), and a sense of peace and privacy that is increasingly hard to find. Whether it's mornings watching boats pass through the channel or quiet evenings at the water's edge, this is a setting that invites you to slow down and stay awhile. The existing home is ready for your vision--whether restoration, expansion, or reimagining. Whatever you choose, here's your opportunity to create something special in an extraordinary setting. Located near the island clubhouse and just steps from the water, there's potential for a mooring and possibly a dock (please verify). You're encouraged to perform your own due diligence regarding dock feasibility and accessory dwelling unit opportunities. It's rare to find this level of frontage, sandy beach access, and panoramic views in one property! Rarer still to have the opportunity to make it your own.

494 Island Ave, Portland

Listing courtesy of Locations Real Estate Group LLC.

$499,000
3 Beds ⋅ 2 Baths
Well maintained, owned and loved by the same family since it was built nearly a century ago, this shingle-style Dutch Colonial is ready to create new memories for the next stewards. Removed wallpaper on the first floor and sanded, primed and patinted the ceilings, walls and trim. Renovated the first floor bathroom. This Libbytown neighborhood opportunity provides great value relative to its peers, It's a keeper with an enclosed backyard on a dead-end street. Hint: hardwood floors are in great condition under the first floor carpet.

15 Rudman Rd, Portland

Listing courtesy of EXP Realty.

$899,000
3 Beds ⋅ 2 Baths
Hard-to-find property featuring industrial zoning with broad potential applications. This property would also serve as an excellent development site for either commercial or residential. This well maintained single-family home includes a detached commercial garage with a large finished upper-level space complete with multiple bedrooms and bathrooms, a kitchen and open living room. This space is currently not permitted as a legal unit. Conveniently located just minutes from I-295, offering easy access for commuters, contractors or business owners alike. Relocate or establish your business here or bring your vision to this site!

1041 Ocean Ave, Portland

Listing courtesy of Greater Portland Realty.

$1,080,000
3 Beds ⋅ 2 Baths
DIAMOND PASS Nestled in among vintage year-round Peaks Island cottages this is a unique and prized area of the island. You have deeded shore rights and can amble down the passage to the beach to enjoy all the wonders of the shore. Fully equipped kitchen with pantry, dining room, comfortable living room with wood stove, large family room, laundry room, 2 baths, 3 bedrooms, deck, patio and outbuildings. You have commanding water views of Casco Bay, Diamond Passage & Portland Harbor. And, watch the Portland skyline light up at dusk with the twinkling lights of evening approaching. A perfect location to have picnics on the beach, a refreshing dip to cool off on a hot summer day, a paddle on the bay. Head down to the sailing/tennis club to socialize with friends. Partake of the dazzling pink & purple sunsets from the patio, deck or comfort of your island home. One of the best places to watch the Fourth of July fireworks. There's no end to the pleasure this property will provide!!!!

364 Island Ave, Portland

Listing courtesy of Portside Real Estate Group.

$650,000
3 Beds ⋅ 2 Baths
HUGE PRICE IMPROVEMENT--DON'T MISS THIS PEAKS ISLAND OPPORTUNITY! Welcome to 17 Elizabeth Road, a thoughtfully updated and lovingly maintained 3-bedroom, 2-bath coastal retreat just a scenic 17-minute ferry ride from downtown Portland. Only a six-minute walk or quick golf-cart ride from the ferry landing, this home offers peaceful island living with easy access to Portland's acclaimed restaurants, shops, galleries, and waterfront. Filled with character, the home features hardwood floors, abundant natural light, sea-glass-inspired interiors, a beautiful stained-glass window, and a one-of-a-kind staircase crafted with repurposed piano legs. Recent improvements include new appliances, fresh landscaping, and interior and exterior paint, making the property move-in ready. Enjoy morning coffee on the welcoming front porch, then unwind after the beach on the private back porch overlooking a charming backyard oasis. The oversized shed offers endless possibilities as an art studio, bunkhouse, workshop, gardening space, or storage for kayaks, bikes, and beach gear. Centennial Beach is just a short walk away, with boating, fishing, kayaking, sailing, pickleball, tennis, cycling, golf-cart cruising, and coastal walks all close at hand. Peaks Island also offers a grocery store, restaurants, shops, a post office, and an elementary school. Whether you're seeking a year-round home, summer getaway, or investment property, 17 Elizabeth Road delivers exceptional character, versatility, and value. Make your move before summer ends and enjoy the magic of Maine island living for generations to come!

17 Elizabeth St, Portland

Listing courtesy of Carey & Giampa, LLC.

Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal,noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.

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