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$645,000
1 Beds ⋅ 1 Baths
Portland's working waterfront becomes part of the view from this distinctive top-floor residence at Chandler's Wharf. Vaulted ceilings, multiple skylights, and a signature circular window give the interior an airy architectural presence. The expansive living area captures broad views over the harbor, Casco Bay, and the rooftops of downtown Portland, creating a remarkable backdrop that changes throughout the day. A well appointed kitchen is adjacent to the main living space, and the private bedroom suite includes the home's full bath and a walk-in closet. Located within Portland's gated waterfront community, the residence offers elevator access and a designated space in the secure garage. Step outside and Commercial Street, acclaimed restaurants, galleries, shops, ferries, and the Old Port are all close at hand. An inviting city getaway in a location that places the energy and character of Portland's waterfront just beyond your door.

716 Chandlers Wharf, Unit 716, Portland

Listing courtesy of RE/MAX By The Bay.

$2,099,000
4 Beds ⋅ 5 Baths
The final residence in this collection of just four historically inspired townhomes is now available. With the other three units already spoken for, this is your last opportunity to own a thoughtfully designed, low-maintenance home in Portland's coveted West End. South-facing and filled with natural light, this sophisticated new-construction residence pairs timeless architecture with modern efficiency in one of Portland's most historic and walkable neighborhoods. Offering the comfort and functionality of a single-family home without the upkeep, it delivers an exceptional lifestyle that's increasingly difficult to find. The spacious open-concept main level seamlessly connects the kitchen, dining, and living areas, extending to a generous 200-square-foot deck for effortless indoor-outdoor entertaining. The fully finished lower level provides valuable additional living space, ideal for a media room, fitness area, home office, or guest suite. Designed with flexibility in mind, the home offers two potential primary suites, allowing owners to tailor the layout to their lifestyle. Multiple private outdoor spaces--including an upper-level deck perfect for morning coffee and a rooftop deck with panoramic West End views and glimpses of Back Cove--provide inviting places to relax throughout the day. A private two-car garage offers direct access to the home and is paired with elevator-ready construction, providing flexibility for future accessibility and comfortable long-term living. High-performance features, including heat pumps throughout, an ERV fresh-air ventilation system, and EV charger-ready garage parking, provide year-round comfort and energy-efficient living. Move-in ready and beautifully finished, this is the last opportunity to own one of only four newly constructed townhomes in Portland's historic West End--a rare offering in one of the city's most sought-after neighborhoods.

55 Carleton St Unit A, Portland

Listing courtesy of Waypoint Brokers Collective. ali@waypointbrokers.com
$729,000
4 Beds ⋅ 2 Baths
Welcome to 27 Berkeley Street, a classic Portland home in desirable Deering Center with four bedrooms, thoughtful updates, an attached garage, and a private backyard with an in-ground pool. Inside, hardwood floors and original character are complemented by modern improvements. The main level features a comfortable living room centered around a traditional brick fireplace, a dining area, and an updated kitchen with soft green cabinetry, stainless steel appliances, farmhouse-style sink, open shelving, and contemporary finishes. Upstairs are four bedrooms with hardwood floors and abundant natural light, along with a refreshed full bathroom featuring a new shower, stone-topped vanity, and modern fixtures. A large walk-up attic adds exceptional storage and is one of the home's most distinctive features, with wood flooring, exposed framing, and a central brick chimney. The space may also offer possibilities for future improvements, subject to applicable permits and approvals. Outside, the fenced backyard creates a private retreat with an in-ground swimming pool, patio, and space for entertaining, gardening, or simply enjoying Maine summers. An attached garage and driveway provide additional everyday convenience. Recent improvements include new roof shingles, an updated kitchen, and an updated bathroom. Located in an established Deering Center neighborhood, 27 Berkeley Street is a hard-to-find combination of character, flexible space, outdoor living, and Portland convenience. Private showings available by appointment. Seller is licensed in Maine real estate.

27 Berkeley St, Portland

Listing courtesy of Keller Williams Realty.

$609,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully updated 3-bedroom, 2-bath, virtually maintenance free home nestled between Portland's Deering and Nason's Corner neighborhoods. Thoughtfully maintained with extensive updates inside and out, this charming property offers the perfect blend of classic character and modern peace of mind, all in a peaceful setting. From the moment you arrive, you'll appreciate the well-landscaped yard, newer driveway (2023), and updated walkway that create outstanding curb appeal. The backyard is private, fully fenced in and the composite deck will keep it maintenance free. Step inside to discover beautifully refinished hardwood floors, an updated first-floor bathroom, and a bright, inviting layout. The enclosed porch features new flooring and new windows, providing the perfect spot to relax. The extensive list of recent improvements means you can move in with confidence. Major updates include a new roof, new gutters with leaf covers, new first-floor windows with newer windows upstairs, all new kitchen appliances, and a high-efficiency Buderus furnace installed in 2024, along with a new hot water heater and oil tank. The professionally sealed, dry basement offers added peace of mind. No moisture concerns here. See disclosures for full list! Every detail has been thoughtfully addressed, making this home truly move-in ready. Conveniently located near local shops, restaurants, parks, schools, and downtown Portland, this exceptional home combines comfort, quality, and convenience, in a quiet, peaceful neighborhood. With so many updates already completed, all that's left to do is move in and enjoy!

56 Four Winds Rd, Portland

Listing courtesy of River's Edge Realty LLC.

$2,943,000
3 Beds ⋅ 3 Baths
LIVE ELEVATED AT 246 EASTERN PROMENADE Only 6 Residences Remain. Completion Spring 2027. Perched above Casco Bay on the grassy sweep of the Eastern Promenade, this collection of just 13 architecturally striking condominiums marks the first residential development on this iconic stretch of Portland's East End in over 50 years. Each residence is thoughtfully designed for those who appreciate timeless elegance, elevated craftsmanship, and a genuine connection to place. This 2,514 sq ft main-level residence offers effortless, single-floor living with direct entrance into the building and a private patio that opens onto the Promenade's network of paths - perfect for leashed dog walks, morning coffee, or unwinding after work. Inside, an open-concept living area centers on a fireplace and wet bar, ideal for quiet nights in or entertaining guests. Two ensuite bedrooms provide privacy and flexibility, while a versatile den/third bedroom adapts easily to a home office, guest room, or media space. Floor-to-ceiling windows and 9-10 ft ceilings fill the home with natural light and views toward Casco Bay. Custom-built kitchen and bath cabinetry by Pond Cove Millworks, and with construction still underway, there's still time to personalize select finishes. Nichiha architectural fiber cement siding, energy-efficient Pella windows, and top-tier HVAC systems ensure comfort year -round, complemented by garage parking, a private climate-controlled storage room, dedicated bike storage, a mail room, and elevator access throughout the building. Steps from the East End beach, the Eastern Trail, the Portland Observatory, Allen Park Gazebo and just a short stroll to the restaurants, cafés, galleries, and the energy of the Old Port. 246 Eastern Promenade offers a rare blend of coastal serenity and vibrant city living. Hard hat tours are now available. Reach out today for floor plans, detailed specs, and to schedule your visit.

246 Eastern Promenade Unit 101, Portland

Listing courtesy of The Flaherty Group.

$699,999
4 Beds ⋅ 4 Baths
OPEN HOUSE - Saturday, September 19th - 10am - 12pm Sunday, September 20th - 10am - 12pm Welcome to 64 Tarbell Ave! 64 Tarbell Ave in Portland, Maine, includes four bedrooms, three and a half bathrooms, over 2,500 square feet of living space, and three garage spaces. Situated on an expansive 0.77-acre lot, this home features major recent updates including a new roof, fresh paint throughout, refinished hardwood paired with new flooring, updated sink and vanity fixtures, a brand-new water heater, brand-new 2026 heat pumps, and an upgraded 200 AMP electrical service. The light-filled interior is highlighted by soaring vaulted ceilings, exposed wood beams, skylights, a gourmet kitchen with granite countertops and stainless steel appliances, and a level yard with patio space. Tucked away in a peaceful neighborhood setting, this property pairs serene suburban living with unbeatable access to everything in town. The impressive 0.77-acre grounds provide rare outdoor space and privacy right in the city, while placing you just minutes from the vibrant amenities along Forest Avenue, local schools, shopping centers, and downtown Portland.

64 Tarbell Ave, Portland

Listing courtesy of Realty ONE Group Next Level.

$699,000
2 Baths
Incredible investment property alert! Loved by one family for nearly fifty years & sitting smack-dab in the center of Portland's spoils, this Rosemont duplex is a rare opportunity to plant roots in a coveted locale. This super solid New Englander has newer heating systems, windows & walkways, and features vintage details to the tune of original built-ins & hardwood floors beneath the carpets. Be it an owner-occupied or landlord scenario, a modern-day cosmetic refresh will make this treasure shine. Each unit boasts two bedrooms, a full bathroom, a dining room, kitchen, and a living room. Upsize potential abounds in the third-floor partially finished attic space for an additional living area. Plenty of room for your belongings and a cozy multi-use room in the basement (home office, anyone?) keep clutter at bay. Separate utilities make life a breeze. Soaking up the sun outside? Front & back porches and balcony decks are ready for morning coffee and evening cocktails. Plenty of parking, perennial plants, a privacy fence, green space, and room for lounging are all available in this special spot, as well as a garage for your car, toys, and tools. Tree-lined, welcoming, and walkable, this stretch of Woodford Street has generations of neighbors who have happily stayed put through the years. It's easy to see why: locally sourced groceries, fresh-baked treats, dinner, drinks, peaceful trails, and Deering High School are all steps away. You can even see the iconic Woodfords Corner clock tower from your front steps. A cherished gem that's ready for its next chapter - don't miss this one!

436 Woodford St, Portland

Listing courtesy of King + Miller Real Estate. info@kingmillerrealestate.com
$199,000
1 Beds ⋅ 1 Baths
Welcome to this charming second-floor one bedroom, one bathroom condo offering comfortable, easy living in a convenient in-town location. the open concept layout creates a bright and functional space that is easy to enjoy. The unit also includes a designated parking space and is close to local shops, restaurants and every day amenities, being a short distance from everything Portland has to offer. Presently rented, this cozy one bedroom is a great investment opportunity, or vacation pad in the city.

58 Portland St Unit 3, Portland

Listing courtesy of Harborview Properties, Inc..

$425,000
1 Beds ⋅ 1 Baths
Sixth-floor living above downtown Portland, with water views of Back Cove on one side and the City Hall clock tower on the other. Unit 606 at Chestnut Street Lofts offers 935 square feet of open, light-filled space on one of the peninsula's most walkable blocks. Built in 2007, the loft carries the clean industrial character the building is known for: concrete floors, tall ceilings, and oversized windows that pull daylight deep into the room throughout the day. The open plan reads as one generous living space and adapts easily, whether that means a defined sleeping area, a dedicated home office, or both. A full bath with laundry serves the unit. Elevation is what sets this one apart. From six floors up the sightlines clear the rooftops, so the Back Cove water views and the City Hall tower belong to the unit itself, not only to the shared deck. Building amenities include a panoramic shared roof deck overlooking Back Cove, the Portland skyline and Casco Bay, assigned off-street parking, dedicated locked storage, dedicated parking space and keyless secure entry. High-speed internet and premium cable are included in the association fee. Step outside and the city is immediate. The Old Port, Congress Street, the Portland Museum of Art, Monument Square and a nationally recognized restaurant scene are all within a few blocks. Gas-fired hot water heat and public water. Offered as a low-maintenance primary residence or a turnkey pied-à-terre in the heart of Portland.

21 Chestnut St Unit 606, Portland

Listing courtesy of EXP Realty.

$449,900
3 Beds ⋅ 2 Baths
A completely renovated Portland single-family home at a price increasingly difficult to find. 566 Washington Avenue combines move-in-ready condition with a surprisingly functional three-bedroom layout, including a first-floor bedroom, first-floor laundry and 1½ baths. The bright, open interior features new flooring and finishes, a beautifully updated kitchen with new cabinetry, countertops and appliances, and fully renovated bathrooms with clean, timeless styling. Updated windows, systems, mechanicals and zoned heat pumps provide year-round comfort, efficiency and peace of mind. Additional advantages include public water and sewer, a full basement, off-street parking and the freedom of single-family ownership without a condominium fee. Located in Portland's desirable East Deering neighborhood, the home is convenient to Back Cove, downtown Portland, neighborhood shops and restaurants, and I-295. The expensive work has already been completed--simply move in and enjoy a thoughtfully renovated Portland home with modern comfort, manageable living space and an exceptionally convenient location.

566 Washington Ave, Portland

Listing courtesy of Spectrum Real Estate.

$575,000
3 Beds ⋅ 2 Baths
Location, Location, Location! This newly renovated three-bedroom, one-and-a-half-bath home in the highly sought-after West End of Portland offers an unparalleled walkable lifestyle. Step outside your door and immerse yourself in everything that makes Portland so special: - Walk to World-Class Dining: Enjoy renowned restaurants and charming cafes just steps away. - Explore Arts & Culture: Galleries, museums, and performance venues are within easy reach. - Discover Unique Shops: Boutique stores and local finds are just a stroll away. - Enjoy Scenic Parks: Relax and unwind in nearby green spaces like the Western Promenade. - Admire Historic Architecture: The West End's beautiful 19th-century charm surrounds you. Access the Waterfront: A pleasant walk leads to the Old Port and Portland's working waterfront. Inside, you'll find a beautifully updated home featuring: Newly Renovated: Enjoy the benefits of modern updates throughout. Updated Systems: Ensuring comfort and efficiency for years to come. New Bathrooms: Featuring stylish and contemporary finishes. New Kitchen: Designed for both beauty and functionality. Living in Portland means enjoying: a strong sense of community, abundant outdoor activities, a thriving craft beverage scene, year-round events, and easy access to all essential amenities. Don't miss this incredible opportunity to embrace the vibrant and walkable lifestyle of Portland's West End!

29a Pine St, Portland

Listing courtesy of Keller Williams Realty.

$347,000
2 Beds ⋅ 2 Baths
Welcome to easy condo living in the sought-after North Deering neighborhood! This inviting 2-bedroom, 1.5-bath condo offers a comfortable and functional layout with additional flex space--perfect for a home office, den, or workout area. Enjoy a backyard setting that provides a nice sense of privacy, along with convenient parking and a basement offering plenty of additional storage. A wonderful opportunity for low-maintenance living in a desirable Portland location, close to local amenities while still maintaining a neighborhood feel.

99 Northwood Dr Unit 99, Portland

Listing courtesy of Waypoint Brokers Collective. amanda@waypointbrokers.com
$2,465,000
8 Baths
Prime mixed-use building in Portland's Arts District, across the street from Portland Museum of Art's expansion project; ideal for redevelopment. This 7969 SF structure features 4141 SF of retail space, currently the iconic Mathew's Pub, also known as Portland's oldest pub. This space has a full kitchen and 1490 SF roof deck. If desired, sale includes business establishment. Above the retail area you will also find 8 fully leased residential apartments and an unfinished 766 SF attic area. Imagine the possibilities...Also listed commercial MLS #1677098

133 Free St, Portland

Listing courtesy of Town & Shore Real Estate.

$380,000
1 Beds ⋅ 1 Baths
Historic character meets modern city living in the heart of Portland's iconic Old Port. This one-bedroom, one-bath industrial-style loft offers soaring 15-foot ceilings, exposed brick, original wood beams, and oversized windows that flood the home with natural light while overlooking Post Office Park and the vibrant streetscape below. The thoughtfully designed multi-level layout creates distinct spaces for living, dining, working, and sleeping, making the home feel spacious, functional, and full of personality. Whether you're entertaining friends, working remotely, or unwinding after exploring the city, this loft offers a warm and inviting atmosphere unlike anything else. Located in one of the Old Port's landmark historic buildings--home to the Portland Art Gallery--residents enjoy secure entry with smartphone-enabled intercom access, elevator service, private storage, bicycle storage, and a shared laundry room. Just outside your door, you'll find Portland's award-winning restaurants, boutique shopping, galleries, the working waterfront, Casco Bay ferries, the Portland Museum of Art, farmers markets, and countless local favorites, all within minutes. With efficient heating, low condo fees, and an unbeatable walkable location, this is a rare opportunity to own an authentic Old Port loft in one of Maine's most sought-after neighborhoods. Whether you're looking for a full-time residence, a stylish city retreat, or a Portland home base, 99 Silver Street delivers the quintessential downtown lifestyle.

99 Silver St Unit 3-7, Portland

Listing courtesy of Signature Homes Real Estate Group, LLC.

$1,500,000
3 Baths
103 Read Street presents a substantial 1.41 acre offering in Portland, combining an existing three unit property with three additional vacant lots and compelling long term potential. The existing multi-family includes three residential units, while the additional acreage creates an opportunity to explore a range of future uses or development possibilities. A conceptual development plan explores the potential of an 8-16 unit Cottage Court community, subject to municipal review and approvals. The location offers convenient access to Back Cove, Baxter Boulevard, Payson Park, USM, downtown Portland, public transportation, and major commuter routes. With significant acreage in an established Portland neighborhood, 103 Read Street offers an intriguing opportunity for an investor, developer, or buyer looking to take a longer term approach to the property. Property is being sold as-is.

103 Read St, Portland

Listing courtesy of RE/MAX By The Bay.

$569,000
1 Beds ⋅ 1 Baths
Come experience city living at its finest in this beautifully updated 1 bedroom 1 bath condo located conveniently between Portland's East End and the Old Port. This move-in ready condo is just steps from the waterfront and Portland's award winning restaurants, museums, galleries and shops. This condo enjoys a private patio where you can sit, relax and hear the seagulls and feel the ocean breeze with direct access to a shared community courtyard. The light filled living space boasts 9' ceilings, gleaming hardwood floors, and a cozy gas fireplace. The well-appointed kitchen features white cabinetry, gorgeous tile and marble countertops with counter seating and an adjacent dining area. The spacious bedroom features two generous closets, updated walk-in shower, and in-unit laundry. Central air provides comfort year round. Additional amenities include a large private storage unit and 1 parking spot in the Ocean Gateway Garage. The Bay House is a well-run, pet-loving Association with updated common areas

22 Hancock St Unit 211, Portland

Listing courtesy of RE/MAX Shoreline.

$442,000
3 Beds ⋅ 1 Baths
Discover the charm of Portland living in this spacious and inviting condominium, thoughtfully located for easy access to all the city has to offer. Inside, generously sized bedrooms and large proportioned rooms provide plenty of space for comfortable everyday living, working from home, and entertaining. Abundant storage throughout the home, along with additional basement storage, makes it easy to stay organized while preserving the condo's generous living areas. Step outside to your own private deck, an ideal spot for morning coffee or simply enjoying some fresh air. With its combination of spacious interiors, large bedrooms, exceptional storage, and private outdoor space, this condo offers a comfortable and livable setting that is increasingly hard to find in Portland. Enjoy being close to the city's renowned restaurants, shops, breweries, parks, and waterfront while returning home to a space that feels pleasantly removed from the bustle. Whether you're looking for your first home, a convenient city residence, or an investment property, this condo offers an opportunity to enjoy the best of Portland with room to live, work, and relax. Seller is giving 6000 dollars in concessions to assist with rate buy down, closing fees or HOA.

1363 Congress St Unit 3, Portland

Listing courtesy of Portside Real Estate Group.

$949,000
2 Baths
Fantastic investment opportunity in Portland's desirable Back Cove neighborhood, just off Ocean Avenue. This well-maintained two-unit property features two bedrooms and one full bath in each unit, providing comfortable and functional living spaces. Separate utilities add convenience for both owners and tenants, while off-street parking is a valuable bonus in this sought-after location. Adding even more potential, the property includes a buildable lot, creating an exciting opportunity for future development, expansion, or additional investment. Ideally situated near Cheverus High School and the Roux Institute at Northeastern University, with convenient access to Back Cove, local trails, neighborhood amenities, downtown Portland, and all that the city has to enjoy. A unique opportunity combining income potential, future possibilities, and an exceptional Portland location.

13 Wellington Rd, Portland

Listing courtesy of Waypoint Brokers Collective. amanda@waypointbrokers.com
$985,000
4 Beds ⋅ 3 Baths
Modern Portland living at its best in this thoughtfully designed 4-bedroom home providing space, comfort, and effortless style. Soaring 9-foot ceilings and rich wood floors create an open, airy feel throughout the main living areas, while large windows invite natural light into every corner of the home. The inviting living room centers around a warm gas fireplace, perfect for cozy evenings or relaxed gatherings. The well-appointed kitchen and dining spaces flow seamlessly for everyday living and entertaining alike, offering both function and comfort in a modern layout. Retreat to the spacious bedrooms, including a serene primary suite designed for relaxation. The bathrooms feature radiant heated floors, adding a touch of everyday luxury and comfort during Portland's cooler months. Each space has been carefully crafted to balance style and livability. Enjoy the ease of a low-maintenance lifestyle, giving you more time to experience everything Portland has to enjoy. Located just minutes from the city's vibrant dining scene, acclaimed coffee shops, eclectic arts and music venues, scenic waterfront, and lush parks, this home places you at the center of it all while still providing a peaceful residential retreat. Whether you're hosting friends, working from home, or exploring the city, this home delivers the perfect blend of modern convenience and Portland charm. A rare opportunity to enjoy space, style, and an unbeatable location in one exceptional property.

61 Owls Nest Rd, Portland

Listing courtesy of Salt Real Estate Co.

$819,000
3 Beds ⋅ 2 Baths
Come live on Peaks Island! Peak-A-View is a year-round cottage on a quiet road in and in move-in condition. It's one of those classic cottages with bead board, fireplace and rocking porches but is fully updated with new windows, heat pump, outdoor shower, generator, gorgeous updated kitchen, 2 full baths and an outdoor shower. Walk to the beach in a minute and look out at the sparkle and the sunsets.

75 City Point Rd, Portland

Listing courtesy of Harborview Properties, Inc..

$549,000
4 Beds ⋅ 2 Baths
A historic 4-bedroom Portland Peninsula home that has been thoughtfully brought into the present with an extensive renovation. The result is a home that feels fresh, functional, and ready for its next chapter. Inside, refinished floors run throughout, complemented by freshly painted walls, trim, and ceilings, along with new lighting. The spacious living and dining rooms offer plenty of room to gather, while the kitchen features brand-new cabinetry, quartz countertops, a tiled backsplash, and new appliances. Two full baths, including a newly added first-floor bathroom, bring flexibility rarely found in a home of this vintage. A brand-new stackable washer and dryer adds convenience, while the expansive back mudroom is the perfect everyday catch-all. Upstairs, all four bedrooms offer their own private retreat. The improvements extend well beyond the finishes, with brand-new plumbing, electrical, a heat pump system, and energy-efficient vinyl windows. Outside, new vinyl siding, roof, exterior doors, metal fascia and trim, and composite porches with PVC railings give the home a crisp new presence while preserving its neighborhood character. Then there is the backyard escape with a BONUS SPACE. A newly finished accessory outbuilding with electricity offers potential for a home office, creative studio, workshop, or yoga room. An oversized driveway makes city living easier, while the generous yard offers room to garden, gather, play, or simply enjoy a little breathing room. Life here is distinctly Portland. The location puts you close to restaurants, coffee shops, parks, trails, and everyday conveniences, with the energy of the Peninsula right in your backyard. It's the charm of an older Portland home with the confidence of knowing the important work has already been done.

1021 Congress St, Portland

Listing courtesy of F.O. Bailey Real Estate.

$1,100,000
5 Beds ⋅ 4 Baths
Nestled within the wooded Pheasant Hill community, 68 Graystone Lane presents a rare combination of space, privacy, and convenience in the heart of Portland. This 4-bedroom, 3.5-bath home features a welcoming front farmer's porch, spacious family room with cathedral ceiling, screened-in back porch, and comfortable living spaces designed for both everyday living and entertaining. The spacious primary suite provides a private retreat with an ensuite bath and walk-in closet. The daylight, walk-out basement adds exceptional flexibility, with a partially finished lower level featuring a 5th bedroom and 3/4 bath--ideal for guests, a home office, or additional living space. As a member of the Pheasant Hill Homeowners Association, enjoy a peaceful wooded setting surrounded by green space, while remaining just minutes from Portland's shopping, dining, recreation, and everyday amenities. Experience the best of both worlds--a private neighborhood setting with all that Portland has to offer close at hand.

68 Graystone Ln, Portland

Listing courtesy of Town & Shore Real Estate.

$1,349,000
7 Beds ⋅ 5 Baths
Exceptional opportunity to own a gorgeous home with bonus unit in the heart of Portland's sought-after Oakdale neighborhood. Offering over 5,000 square feet across three finished levels, this expansive property seamlessly blends historic character with modern amenities and significant systems updates, creating a rare investment or owner-occupant opportunity. With two spacious residences offering excellent rental income potential, this property provides exceptional flexibility for investors, multigenerational living, or those looking to offset their mortgage while enjoying one of Portland's most desirable neighborhoods. The first-floor residence features three bedrooms, one and a half baths, a generous living room, formal dining room, spacious bedrooms, and a bright bonus sunroom. Occupying the second and third floors, the upper residence lives like a single-family home with a spacious living area, formal dining room, updated kitchen, four generously sized bedrooms, the potential to finish a fifth bedroom, and three inviting sun porches that provide flexible space for relaxing or working from home. Throughout the home, beautifully restored original trim, built-ins, hardwood floors, and timeless architectural details showcase its historic charm, while thoughtful updates to the property's major systems provide peace of mind. Whether you're seeking strong rental income, multi-generational living, or the chance to owner-occupy one of Portland's most impressive two-unit homes, this property offers exceptional space, flexibility, and long-term value in one of the city's most charming neighborhoods.

381 Deering Ave, Portland

Listing courtesy of Waypoint Brokers Collective. ali@waypointbrokers.com
$637,500
1 Beds ⋅ 1 Baths
Nestled at the intersection of Portland's historic working waterfront and its vibrant Old Port district, Hobson's Landing is a premier condominium community that is not merely a place to live; it is a meticulously curated environment designed to foster a life of harmony, comfort, and in-city living. Hobson's Landing has been thoughtfully orchestrated, integrating private residences with inviting public spaces (including a guest suite, remote office work area, clubhouse, workout facility and dog wash station), a concierge service and lush courtyards to create a warm and walkable community within downtown Portland. The unit itself has been impeccably maintained, offering like-new modern fixtures within this 1 BR 1 BA unit. Enjoy the gas fireplace in the cooler months, while taking advantage of direct, walkout access to the roof top patio with views to Casco Bay. Conveying with a parking spot in the on-site garage as well as a storage unit, everything has been carefully considered with this elegant property. Whether you are seeking a permanent residence, a low-maintenance in-town retreat, or a sophisticated base from which to explore the Maine coast, this exceptional community offers the very best of Portland living.

383 Commercial St Unit 305, Portland

Listing courtesy of Cates Real Estate. kerry@catesre.com
$320,000
1 Beds ⋅ 1 Baths
OPEN HOUSE SAT 8/29 11-12:30 PM. Experience the charm and character of Portland's historic Marlborough Building at 180 High Street, Unit 22. This inviting 1-bedroom, 1-bath condo offers 607 square feet of thoughtfully designed living space, highlighted by soaring ceilings, beautiful woodwork, hardwood and tile floors, and oversized windows that fill the home with natural light. From the moment you enter the Marlborough, its timeless architecture makes an impression. A grand arched entrance welcomes you into an octagonal foyer featuring a coffered ceiling, terrazzo floors, and the building's distinctive birdcage elevator. Inside the unit, an updated bathroom adds modern comfort, while heat and hot water are conveniently included in the condo fee. Residents also enjoy access to a full laundry room, basement storage, and a peaceful backyard garden space--a welcome retreat in the heart of the city. Ideally located in Portland's vibrant Arts District, you'll be just steps from the Portland Museum of Art and surrounded by some of the city's best restaurants, cafés, shops, and cultural destinations, with Deering Oaks Park and the Old Port within easy reach. Offering historic charm, everyday convenience, and an exceptional downtown location, this is a wonderful opportunity to enjoy all that Portland living has to offer.

180 High St Unit 22, Portland

Listing courtesy of Keller Williams Realty. 207-553-2400
$950,000
3 Baths
Offered for the first time in decades, this well-located 3-unit multi-family property in Portland's desirable Oakdale neighborhood. Each unit is equipped with its own private laundry, separated electricity, and natural gas, as well as a off-street parking. Just moments from Woodford's Corner, residents can enjoy an array of local restaurants, shops, cafes, and neighborhood amenities. Outdoor enthusiasts will appreciate the nearby trails and recreational opportunities along Back Cove. For commuters, I-295 is only 0.75 miles away, while the vibrant restaurants, shops, waterfront, and entertainment of Portland's Old Port are approximately 1.5 miles from the property. The flexible three-unit layout presents an excellent opportunity for an investor, owner-occupant, or anyone looking to build equity in one of Portland's sought-after neighborhoods.

19-21 Linden St, Portland

Listing courtesy of Portside Real Estate Group.

$1,349,000
5 Baths
Exceptional opportunity to own a true two-unit in the heart of Portland's sought-after Oakdale neighborhood. Offering over 5,000 square feet across three finished levels, this expansive property seamlessly blends historic character with modern amenities and significant systems updates, creating a rare investment or owner-occupant opportunity. With two spacious residences offering excellent rental income potential, this property provides exceptional flexibility for investors, multigenerational living, or those looking to offset their mortgage while enjoying one of Portland's most desirable neighborhoods. The first-floor residence features three bedrooms, one and a half baths, a generous living room, formal dining room, spacious bedrooms, and a bright bonus sunroom. Occupying the second and third floors, the upper residence lives like a single-family home with a spacious living area, formal dining room, updated kitchen, four generously sized bedrooms, the potential to finish a fifth bedroom, and three inviting sun porches that provide flexible space for relaxing or working from home. Throughout the home, beautifully restored original trim, built-ins, hardwood floors, and timeless architectural details showcase its historic charm, while thoughtful updates to the property's major systems provide peace of mind. Whether you're seeking strong rental income, multi-generational living, or the chance to owner-occupy one of Portland's most impressive two-unit homes, this property offers exceptional space, flexibility, and long-term value in one of the city's most charming neighborhoods.

381 Deering Ave, Portland

Listing courtesy of Waypoint Brokers Collective. ali@waypointbrokers.com
$298,500
2 Beds ⋅ 2 Baths
Realize your home ownership dreams! This spacious interior townhouse in this newly built building offers 2 bedrooms, 1.5 bathrooms and a parking spot in a comfortable 818 sq ft. home. With its own raised garden bed, shed, and deck this home is ready to occupy today! Each parking spot will be EV-ready for the buyer to install their own charger- with the conduit running from parking lot to each individual electrical panel. Same with solar - the conduit running from roof to each unit. These newly built homes will stay cozily warm -and cool - via the efficient heat pumps. Located near the Washington Avenue businesses as well as the Portland Peninsula, this home will be close to everything! Baxter Boulevard and Payson park are within easy reach and you'll have easy access to I295. This Income Qualified Workforce Home could be your door to the world of owning your own home! The Front Street Condominium Association is phase 3 of the Portland Housing Authority's award winning development of this special neighborhood. These brand new high quality condominium homes are being built to create new home-ownership opportunities in the city. 8 units total, of which 2 are market rate and 6 being income restricted. Buyers will fill out a form to validate eligibility based on household size. Must be at or under 120percent of of Median Area Income.

41 W Presumpscot St Unit B, Portland

Listing courtesy of Gardner Real Estate Group.

$495,000
2 Beds ⋅ 2 Baths
OPEN HOUSE SUNDAY SEPTEMBER 20 10:00-11:30 MOTIVATED SELLERS This BRIGHT and SUNNY UPDATED KITCHEN AND BATHS WEST END 2 bedroom, 2 bath, 2 off street dedicated parking spaces 2ND FLOOR CONDO IS MOVE IN READY! Ready for new owners. Eat-in kitchen With GRANITE counters, stainless appliances, wide pine floors, updated baths .LARGE PRIMARY with a large closet. The setting offers the perfect blend of energy and charm -it is both walkable (described as a WALKERS PARADISE)and wonderfully livable. Just steps to Tandem, the Roma(next door) art museum, , theatre, concerts, professional sports and for medical professionals , the hospital. A WELLNESS SPA on first floor. Schedule your showing soon.

773 Congress St Unit 3, Portland

Listing courtesy of EXP Realty.

$699,000
5 Beds ⋅ 3 Baths
New Price and owners say sell! Offered for sale by the Estate, it has been owned by the same family for decades.The property presents excellent potential, including the possibility of adding ADU units where the 2-car garage stands or maybe subdividing the 12,000 sf large lot - all with City approval needed of course. Currently, it is the perfect multi-generational home with room for a nanny or in-law. Offering classic charm and sitting on a generous lot in Portland's convenient Nason's Corner neighborhood, it is Ideally located close to everything. It is within walking distance to Portland Trails, local schools, The Sinful Kitchen, Applebee's, a neighborhood corner store, the Lowe's shopping center, and is within biking distance to New England College, Capisic Pond Park, and Rosemont Market. The small first floor unit with its own entrance was once used as a third unit and with City approval might be able to be used again as an ADU or as in in-law or guest suite. It would add two bedrooms and a full bath giving the first floor 4 bedrooms. Another possible use for the addition, also with City permission, is an in-home occupation such as a hair salon or office. The first-floor apartment features two bedrooms, an eat-in kitchen, a living room, and a full bath as well as basement access. It is heated by oil, with the tenant responsible for oil and electricity. The second-floor apartment, which includes the third floor, offers two or three bedrooms, a living room, dining room, and kitchen, along with basement access. This unit is heated by a propane monitor, with the tenant paying for propane and electricity. Hard to believe this is still on the market! The estate has reduced the price and is entertaining all reasonable offers. It is now available for immediate occupancy. Portland rent control does not apply if the property is purchased by an owner/occupant. Opportunity knocks!

14 Devon St, Portland

Listing courtesy of HarborCity Realty.

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