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$639,000
3 Beds ⋅ 2 Baths
You will be amazed at the original detail when you enter this sun filled condominium. The living room ceiling and plaster work went through a painstaking restoration that will impress even the most discerning eye. Having a flexible floorplan, this condominium offers 2 to 3 bedrooms as well as a office/den or current use as a music room. This condominium also offers a large private deck for your outdoor enjoyment. This condominium is 2 condominiums that have been combined. There is storage in the basement.

143 Pine St Unit 1&2, Portland

Listing courtesy of Keller Williams Realty.

$525,000
2 Beds ⋅ 2 Baths
Welcome to the iconic Portland House Condominiums. Sitting prominently atop of Munjoy Hill it serves as a landmark to Portland's famous Eastern Promenade. From the private balcony, this spacious 2 bedroom, 4th floor unit offers views of Back Cove and Casco Bay in the distance and a close up view of the vibrant activity in one of Portland's most desirable neighborhoods, loved by locals and visitors alike. This unit offers a spacious living/dining area, a primary bedroom with private bath, plus a second bedroom and full guest bath. The efficient galley kitchen works well as is or could be reconfigured to your personal taste. You will also enjoy a staffed front entry desk and added amenities such as heat, hot water, cable, internet, a common outdoor patio with grilling area, a common, beautifully furnished community room and a workout room, all bundled into the monthly HOA fee. Parking is a breeze with garage parking and direct elevator access to the building. Just outside is Eastern Prom Park offering walking trails, a public beach, a playground, tennis courts, food trucks and much more! Here, local residents and visitors assemble for picnics, sports and enjoying the spectacular views and ocean breezes. The very same view you will cherish day in and day out from your own balcony! Nearby restaurants invite you to experience the cuisine of some of North America's best award winning chefs and bakers just minutes from your front door. Don't miss this opportunity to live at one of Portlands most desirable locations!

45 Eastern Promenade Unit 4J, Portland

Listing courtesy of RE/MAX Shoreline.

$1,850,000
6 Beds ⋅ 5 Baths
One of Portland's most historic homes, the Samuel Spring House, was designed by noted architect Charles A. Alexander in 1855 and is currently featured in Portland Magazine's Summer 2026 Guide in the monthly ''Talking Walls'' article. Owned by the same family since 1965, it offers over 6,000 square feet of living space and is ready to be restored to its original splendor. Touring the mansion reveals untouched original details throughout, from staircases, plaster moldings and medallions, to wood floors, doorknobs, mantels, and gas chandeliers converted to electric. The grand staircase greets you upon entry, with formal parlors on either side of the main hall, the left leading to a back parlor. A large formal dining room features a walk-in china closet and remarkable corner sink, while the rear holds a butler's pantry and kitchen complete with the original call bells. The second floor offers five generous bedrooms, a large flex room, and two baths, while the third floor includes a bedroom, bath, attic space, and a spiral staircase leading to the widow's walk with views of the Fore River and glimpses of Casco Bay. Set on a corner lot with an impressive granite and iron spindle fence, this home is steeped in Portland history and waiting to be cherished once again. Portland Magazine article in attachments.

300 Danforth St, Portland

Listing courtesy of Keller Williams Realty.

$699,000
2 Beds ⋅ 2 Baths
If you've been searching for a condo in Portland, you already know opportunities like this are rare. Intentionally priced to generate immediate interest, this represents one of Portland's strongest values. Perfectly positioned at the gateway to the Old Port and the Arts District, 25 High Street boasts an exceptional Walk Score of 94, placing nationally recognized restaurants, cafés, galleries, the working waterfront, shopping, recreation and everyday conveniences just steps from your front door. Perched on the waterside upper level, Unit 410 is filled with natural light and enjoys glimpses of Inner Casco Bay and Portland's iconic working waterfront. Nearly 1,200± SF offers an open-concept design where the beautifully appointed kitchen flows seamlessly into spacious living and dining areas. Two generous bedrooms, two full baths, in-unit laundry and quality finishes throughout deliver the comfort, style and functionality discerning buyers expect. The professionally managed, pet-friendly association welcomes both dogs and cats with no size or breed restrictions and features a fitness center, elevator, secure entry and on-site storage. Even more impressive, the remarkably affordable $395/month condominium fee is roughly half that of many competing Portland condominium communities. Whether you're looking for a full-time residence, a sophisticated in-town retreat or a true lock-and-leave lifestyle, this move-in-ready home delivers exceptional quality, outstanding value and one of Portland's most desirable urban locations. Upper-floor, waterside residences with this combination of location, light, amenities, affordability and value simply don't come along often.

25 High St Unit 410, Portland

Listing courtesy of Benchmark Real Estate.

$425,000
2 Beds ⋅ 2 Baths
Classic 1930s Gambrel brimming with charm, character, and opportunity in a convenient Portland location! This property is being offered for the first time since 1988. This inviting two-story home offers approximately1,384 square feet of living space with 2 bedrooms and 2 full bathrooms on a manageable 0.13-acre lot. Hardwood, tile, and vinyl flooring complement the functional layout, creating comfortable spaces for everyday living while preserving the timeless appeal of this classic home. The very private, fully fenced backyard is a true retreat, offering the perfect space for pets, gardening, outdoor entertaining, or simply relaxing in your own secluded oasis. Conveniently located just minutes from Portland's shopping, restaurants, parks, trails, schools, and major commuter routes, you'll enjoy easy access to everything the city has to offer. While some updating will allow you to add your own style and finishes, this home offers solid bones, lasting character, and tremendous potential to build equity. Whether you're a first-time homebuyer, looking to downsize, or searching for your next investment opportunity, 705 Riverside Street is ready for your vision. Bring your ideas and make this charming Gambrel your own!

705 Riverside St, Portland

Listing courtesy of Excellence Realty.

$595,000
1 Beds ⋅ 1 Baths
If you choose to live in Portland, the Eastern Promenade is the place to be! Here is your chance to gaze out of your big bank of windows and see all of the harbor traffic that you can take in. Step into this top floor condominium unit and feel energized by the vaulted ceilings and tons of natural light all day long. This open concept offers an open floor plan perfect for you to set up just exactly how you want to live. The kitchen allows you to eat in and converse with guests while preparing your next meal. Just off the kitchen is your own large private deck with ocean views, perfect for entertaining. The bedroom is extra-large with sky lights, and the beautiful full bath includes a smartly tiled shower. There is in unit laundry as well as one dedicated parking space that comes with this unit along with basement storage. Just across the street, enjoy 66 acres of gentle sloping grass to enjoy the panoramic Casco Bay Views. The East End Beach is nearby and so is Portland's Old Port where you can experience the best cuisine, coffee shops, galleries and so much more!

38 Eastern Promenade Unit C, Portland

Listing courtesy of Gardner Real Estate Group.

$599,000
3 Beds ⋅ 2 Baths
New Price! Opportunity knocks in Portland's desirable Back Cove neighborhood! This classic 3-bed, 1.5-bath colonial offers 1,378 sq ft of immediate livability on an expansive 1/3-acre double lot. Filled with natural light, this home offers hardwood flooring, original built-ins, a fireplace and a sunroom perfect for home office or enjoying coffee while looking out at the large private back yard. Outside, opportunities abound for garden beds, a firepit, a place for a dog or kids to play, or future expansion. Just moments from Baxter Boulevard, Payson Park, and Portland's vibrant downtown. This home has been pre-inspected for the buyer's convenience. A great value!

87 Read St, Portland

Listing courtesy of Town & Shore Real Estate.

$425,000
1 Beds ⋅ 2 Baths
A spacious first-floor condo in Portland's coveted West End that beautifully blends period charm with modern convenience. Soaring ceilings and bay windows fill the home with natural light, creating an inviting space for both everyday living and entertaining. The expansive kitchen is a dream for home chefs, featuring abundant counter space, newer stainless steel appliances, a gas range, and plenty of room to gather with family and friends. Two separate living areas provide exceptional flexibility for relaxing, working from home, or hosting guests. The thoughtfully designed floor plan includes two full bathrooms, including a private ensuite in the primary bedroom. Two separate entrances and a dedicated mudroom offer added privacy, convenience, and valuable storage space. An in-unit washer and dryer eliminate trips to the basement or laundromat, making daily living effortless. Step outside to enjoy a private side deck and a peaceful backyard oasis--perfect for morning coffee, gardening, or unwinding after a day in the city. Additional highlights include one dedicated off-street parking space, conveniently located first in line directly beside the building, along with a private storage unit in the basement. The well-maintained building has seen numerous recent improvements, including a TC Hafford-installed basement vapor barrier and sump pump, two new dehumidifiers (2024), a new chimney vent liner for the hot water heaters, new chimney vent cap, exterior LED lighting, exterior water spigot, refinished hardwood floors, new carpet, freshly painted common areas, and new mailboxes. Ideally located in the heart of Portland's vibrant West End, you'll be just steps from acclaimed restaurants, neighborhood cafés, parks, entertainment venues, and the city's rich arts and cultural scene. Whether you're looking for a walkable urban home, a convenient city retreat, or a strong long-term investment, 27 Pine Street offers timeless character, modern amenities in an unbeatable locatio

27 Pine St Unit 7, Portland

Listing courtesy of Real Broker.

$595,000
2 Beds ⋅ 3 Baths
Set on a beautiful tree-lined street in Alden's Walk, this charming townhouse-style end-unit condo abuts Portland Trails, offering daily access to one of the city's most loved green corridors. Exceptional natural light fills the home throughout, highlighting a comfortable and flexible floor plan designed for both everyday living and future needs. The welcoming living room features expansive windows, a cozy gas fireplace, and a wall of charming built-ins, while the dining room offers vaulted ceilings and access to a private patio overlooking the peaceful surroundings. A main-level bonus room, paired with the first-floor full bath, provides wonderful versatility as a den, office, guest space, or potential first-floor bedroom--allowing for one-floor living now or in the future. The kitchen includes high-end appliances, farmhouse sink, striking Mahogany and Eucalyptus countertops plus a quaint breakfast nook. Upstairs, two en-suite bedrooms and convenient laundry complete the second level. Outside, the beautifully maintained private yard feels like a garden retreat, framed by tall trees, lush landscaping, and mature plantings. Enjoy a quiet, nature-connected setting just minutes from downtown Portland.

6 Wildwood Cir Unit 6, Portland

Listing courtesy of Tim Dunham Realty. 207-729-7297
$1,849,000
4 Beds ⋅ 4 Baths
Architecturally striking and newly custom-built, this extraordinary West End residence exemplifies contemporary luxury living on Portland's Peninsula. Designed to maximize sustainability, natural light and year-round comfort, the home features Therma-Steel insulated panels, Marvin windows, Boral cementitious and wood siding, Azek trim, soaring ceilings, translucent polycarbonate elements and a dramatic two-story light shaft that fills the home with natural light. At the heart of the home is a spectacular custom kitchen completed in 2026. Rift-cut oak cabinetry, integrated storage, a statement island, a paneled refrigerator, black granite countertops and backsplash, and premium Thermador appliances- including a newly added natural gas range- create a space that is as functional as it is stunning. Additional enhancements include an appliance garage and dedicated coffee station, a custom floating dining credenza, motorized blinds, and a newly installed washer and dryer. Spanning three thoughtfully designed levels, the residence offers three bedrooms, two and a half baths, and exceptional flexibility. Crowning the home is a sun-drenched winter garden- a top-floor retreat beneath skylights and a translucent roof system capturing natural light and glimpses of Casco Bay. Additionally, the ground level features a studio apartment with custom kitchen, laundry, full bath, private entrance and outdoor space- ideal for rental income, guests, or a home office/creative studio. Rare outdoor living spaces extend the interiors, offering six covered porches and an enclosed backyard. A climate-controlled garage is a rare Peninsula amenity. Perched in Portland's coveted West End, within walking distance of restaurants, the Old Port and the waterfront, this one-of-a-kind residence offers an extraordinary opportunity to own a modern architectural masterpiece in one of Maine's most desirable locations.

5 Salem St, Portland

Listing courtesy of Peninsula Real Estate LLC.

$420,000
3 Beds ⋅ 1 Baths
Well-maintained Cape in one of Portland's convenient neighborhoods. This charming 3-bedroom, 1-bath home combines classic character with extensive updates completed between 2022 and 2025. Major improvements include a 200-amp electrical service, Daikin heat pumps for efficient heating and cooling, a new steam boiler, Bradford White heat pump water heater, new PEX water service with house shutoff, an updated bathroom, and a new dishwasher. Hardwood floors, a flexible first-floor bedroom or home office, and a private backyard complete the package. Conveniently located just minutes from downtown Portland, Back Cove, I-95, shopping, restaurants, and local amenities. A rare opportunity to own a thoughtfully updated home where the major systems have already been addressed.

14 Castine Ave, Portland

Listing courtesy of F.O. Bailey Real Estate.

$489,999
3 Beds ⋅ 1 Baths
Welcome to 106 Beverly Street, a well-maintained ranch-style home set in a quiet, sidewalk-lined Portland neighborhood with convenient access to local amenities, schools, shopping, trails, and commuter routes. This inviting 3-bedroom, 1-bath home offers comfortable single-level living with a functional layout, bright living spaces, a galley-style kitchen, and a dining/breakfast area with sliders leading to a spacious rear deck overlooking the deep backyard. The lower level adds valuable flexible space with a finished room, gas fireplace, ample storage, and walk-out access to the backyard--ideal for a home office, den, gym, playroom, or bonus living area. With its practical floor plan, outdoor space, and desirable Portland location, this home is a great opportunity for buyers seeking comfort, convenience, and room to make it their own.

106 Beverly St, Portland

Listing courtesy of Tidal Realty Group.

$475,000
3 Beds ⋅ 2 Baths
Wonderful opportunity to own this spacious 3 bedroom, 2 bath condo nestled in a private spot surrounded by trees. You'll love the private entrance offering plenty of storage and the beautiful hardwood floors throughout the main living area. Kitchen offers stainless steel appliances, granite counter tops and pantry. Primary bedroom has nice walk-in closet and the full walk-up attic offers a ton of storage. New heating system too. Rear deck offers great outdoor space. Easy to show!

401 Brighton Ave Unit 7, Portland

Listing courtesy of Gardner Real Estate Group.

$499,000
2 Beds ⋅ 1 Baths
Boothby Square Condominium with timeless character and thoughtful updates, perfectly suited for a lifestyle that embraces the energy of the Old Port. This open-concept home features two spacious bedrooms with generous closet space with a walk-in closet in the primary bedroom, an updated bathroom, and comfortable, efficient living with an elevated feel. Laundry is within the building. Complete with a dedicated parking space and located just two blocks from the waterfront, this is an exceptional opportunity to enjoy the very best of downtown Portland living.

341 Fore St Unit 6, Portland

Listing courtesy of Waypoint Brokers Collective. monica@waypointbrokers.com
$645,000
1 Beds ⋅ 2 Baths
Portland, Maine living in the heart of the Old Port, Portland's historic waterfront neighborhood is luxury living at it's best! Portland will keep you active with popular restaurants, boutiques, stores, parks, museums, and everyday amenities just a stones throw away. This super clean and modern single level residence at Hobson's Landing showcases luxury customization and finishes throughout. The open-concept living space features a large living room with a gas fireplace and adjoining private deck. Spend time at the welcoming kitchen with top notch finishes and purposeful design. The bright and cozy 1 bedroom, 1.5 bath condominium includes an ensuite primary bedroom with a walk-in closet and bath with double vanities and radiant heated floors. The Laundry closet, connects the walk in wardrobe closet and the primary bedroom perfectly. deeded garage parking. Added amenities include multiple large outdoor courtyards, a club room with a full kitchen, concierge service, fitness center, dog wash facility and media room!

383 Commercial St Unit 413, Portland

Listing courtesy of Elevate Maine Realty.

$725,000
2 Beds ⋅ 1 Baths
A One-of-a-Kind Two-Level Penthouse in Portland's Historic West End Relocating Seller | Offering a $5,000 Closing Credit toward buyer financing for written offers accepted within the next 10 days. An expansive, light-filled penthouse offering impressive scale on historic, tree-lined Deering Street in Portland's coveted West End. Occupying two floors of a beautifully restored 1867 Victorian, this residence pairs bold historic architecture with high-performance modern upgrades. Highlights include soaring vaulted ceilings, rich hardwoods, exposed brick details, and a sun-drenched, open upper-level flex loft--ideal for a primary suite, executive office, or creative studio. The Penthouse features 1,426 official finished sq ft with ~2,000 sq ft of total heated floor space, delivering a generous, open footprint bathed in natural light. High-efficiency updates include an on-demand natural gas boiler, maximum R-60 attic insulation, sound-dampening floor underlayment, brand-new safety systems, bonus eave storage, patio and a dedicated basement area. A distinct, sunlit residence just steps from the Western Promenade, local dining, the Arts District, Maine Med, and the waterfront. Resident street parking permitted, with nearby off-street garage options. Historic character. Modern efficiency. Exceptional West End value. Private showings available daily by appointment.

29 Deering St Unit 3, Portland

Listing courtesy of Beacon Realty.

$579,000
3 Beds ⋅ 1 Baths
Classic Maine charm meets rare island privacy in this delightful Peaks Island cottage, tucked away on a peaceful 5.0-acre parcel in the sought-after Tolman Heights neighborhood. With 3.5 acres protected by conservancy, this exceptional property offers an uncommon sense of space, serenity, and natural beauty--a truly rare opportunity on Peaks Island. Spend warm summer evenings on the oversized screened porch, gather around the working fieldstone fireplace in the cozy living room, and enjoy the comfort of three inviting bedrooms. The expansive open front yard provides abundant parking and plenty of room for lawn games, gardening, or entertaining family and friends. Whether you're looking for a seasonal retreat or a year-round island escape, this special property offers the perfect blend of timeless cottage charm, exceptional privacy, and the beauty of Maine's island lifestyle.

100 Highland Ave, Portland

Listing courtesy of Keller Williams Realty.

$959,900
4 Beds ⋅ 3 Baths
Beautifully maintained and ideally located in North Deering, this elegant residence offers exceptional flexibility with a fully appointed in-law suite. The private in-law space includes a kitchen, full bath, bedroom, and a bright year-round sunroom complete with a fireplace--creating a warm and inviting extension of the home that works beautifully for guests, extended living, or multi-generational needs. The main home is thoughtfully designed for everyday comfort, featuring a functional layout and seamless flow throughout. An attached two-car garage provides direct entry into the home for added convenience. Recent updates include a new roof, offering peace of mind for years to come. The property is beautifully maintained and well-landscaped, enhancing its curb appeal and overall sense of care. Tucked away on a quiet cul-de-sac in a well-established residential setting, the home offers convenient access to shopping, dining, and local amenities, as well as major commuter routes. A rare combination of space, flexibility, and a truly desirable location. Pre-inspection available upon request.

43 Alice Ct, Portland

Listing courtesy of Harborview Properties, Inc..

$899,000
2 Beds ⋅ 2 Baths
Between Portland's vibrant Old Port and the open waters of the Atlantic lies one of Maine's most beloved island communities. Nestled into the west-facing landscape of Peaks Island, this charming year-round home captures sweeping views of Diamond Passage and Casco Bay, offering a front-row seat to unforgettable sunsets and the rhythms of island life. Filled with natural light, the home's inviting interior features warm wood floors, fresh finishes, and abundant windows framing coastal vistas throughout. The open-concept main level seamlessly connects the spacious kitchen with breakfast bar, dining area, and beam-accented living room, creating an ideal setting for both everyday living and entertaining. Sliding doors open to a generously sized Ipe wood deck, where optional canopy coverage provides comfort for outdoor dining, morning coffee, or evening gatherings overlooking the water. A full bath, coat closet, and welcoming covered front porch complete the first floor. Upstairs, a sun-drenched loft offers exceptional flexibility as a home office, artist's studio, reading nook, guest space, or play area. The primary bedroom occupies the home's distinctive turret, blending unique architectural character with captivating water views. A second bedroom, full bath with skylight and walk-in shower, and convenient laundry area complete the upper level. Outside, the .12-acre lot invites gardening, outdoor entertaining, fireside evenings, and peaceful relaxation. Whether hosting friends, tending flowers, or simply enjoying the sea air, the property offers a wonderful extension of the home's easygoing coastal lifestyle. Just moments from beaches, village shops, quiet island lanes, and the ferry landing, 30 Pleasant Avenue offers the rare opportunity to enjoy year-round island living with comfort, character, and Casco Bay views.

30 Pleasant Ave, Portland

Listing courtesy of Portside Real Estate Group.

$499,000
1 Beds ⋅ 1 Baths
Welcome to 418 Auburn Street, a stylishly updated North Deering home offering a flexible one-bedroom layout that can be converted back into a two-bedroom. This inviting property features a renovated kitchen, a reconfigured living space with added natural light, and a finished detached studio that expands the way you can live and work at home. Inside, the entryway has new flooring and built-in storage. The upgraded kitchen includes butcher block countertops, stainless steel appliances, soft-close cabinetry, updated lighting, and hardwood flooring that continues into the living room. The living room was opened up by removing a former bedroom wall, and two additional windows were added to brighten the space. The bathroom features new tile flooring, a modern vanity, updated lighting, and accent walls. Additional improvements include a built-in illuminated bookshelf, expanded primary bedroom closet space, and fresh paint throughout. The heated studio, created from a converted one-car garage, offers a heat pump, custom French doors, and added windows, making it ideal for a home office, creative studio, or fitness room. The home has also been improved for comfort and efficiency with blown-in attic insulation, new basement windows, LED lighting with dimmers, and a standby generator for peace of mind during storms. Outside, the home shines with fresh dark blue paint, a complementary gray garage and shed, and an opened-up front porch that creates a more welcoming entry. Two sheds and a two-car garage with storage above provide room for tools, gear, and seasonal items. Located minutes from many of Portland's parks, trails, outdoor spaces, Falmouth amenities, and Downtown Portland, this home offers comfort and convenience in a prime location. Beaches, the Jetport, and I-95 and I-295 are all within easy reach. With its flexible layout, modern updates, and inviting studio space, 418 Auburn Street is a standout opportunity in one of Portland's most convenient areas.

418 Auburn St, Portland

Listing courtesy of Signature Homes Real Estate Group, LLC.

$2,950,000
2 Beds ⋅ 3 Baths
Welcome to The Penthouse on Congress--an incredible opportunity in the heart of downtown Portland's Art District, with 360-degree views of the ocean to the mountains, architectural pedigree, and elevated design converge. Set on the top three levels of The Winslow Lofts, this residence lives like a work of art--layered in natural materials, bathed in light, and framed by the ever-changing beauty of the water beyond. Soaring ceilings and dramatic floor-to-ceiling windows create an immediate sense of scale, drawing the outdoors in and showcasing panoramic views of Casco Bay from the main living space. A striking fireplace anchors the room, adding warmth and intimacy to an otherwise expansive, light-filled setting--perfect for both quiet evenings and unforgettable entertaining. The primary suite is a true retreat, offering tranquil water views over Back Cove, a private balcony, a generous walk-in closet, and a spa-like bath with radiant heat floors, designed for indulgence. A second fireplace adds an additional layer of comfort and romance, making this suite feel like a boutique hotel sanctuary high above the city. Arrive via a secure elevator, underscoring the exclusivity and ease of penthouse living. Two dedicated parking spaces--including one within a heated garage--complete the offering, a coveted amenity in downtown Portland. This is not just a residence--it's a statement. A true penthouse lifestyle defined by privacy, design, and breathtaking vantage points. From intimate evenings by the fire to unforgettable gatherings on the rooftop deck with city and water views, this home offers a front-row seat to Portland's most iconic scenery. A living art piece suspended above the city, where luxury, light, and location converge.

547 Congress St Unit 6, Portland

Listing courtesy of Legacy Properties Sotheby's International Realty.

$499,999
3 Beds ⋅ 2 Baths
Rare opportunity! Condo in one of Portland's most highly sought-after, low-turnover communities! This exceptional 3-bedroom, 2-bathroom home offers the ease of condo living with the space and features of a single-family house. The expansive, sun-filled layout boasts a coveted first-floor bedroom, providing perfect flexibility for a main-level primary suite, guest quarters, or a private home office. Unlike standard area condos, this unit includes a private garage to shield your vehicle from Maine winters, plus a full basement for extra storage. Enjoy maintenance-free living just minutes from Portland's world-class dining, vibrant arts district, and scenic waterfront. Openings in this development are incredibly rare so schedule your showing today before this unique opportunity is gone!

115 Delaware Ct Unit 115, Portland

Listing courtesy of Coastal Pine Real Estate, LLC.

$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..

$409,900
2 Beds ⋅ 1 Baths
Nestled in Portland's highly sought-after West End, this charming 2-bedroom condo offers the perfect blend of historic character, modern convenience, and exceptional outdoor living. Set within a beautifully maintained Greek Revival Colonial, the home features original wood floors, a spacious kitchen and a thoughtful layout designed for comfortable everyday living. What truly sets this property apart is its secluded backyard oasis. Step outside to a beautifully landscaped patio surrounded by lush gardens and mature greenery, creating a peaceful retreat rarely found in the city. Whether you're enjoying your morning coffee or unwinding after a day in town, this inviting outdoor space feels like your own hidden sanctuary in the heart of Portland. Inside, you'll find two comfortable bedrooms, a large walk-in closet with washer & dryer, a bonus room on the first floor, and abundant natural light throughout. Located just moments from the Old Port, Portland's renowned restaurants, coffee shops, waterfront, and shopping, this condo offers the best of walkable city living while providing a peaceful retreat from the bustle. Enjoy views of the Fore River and Casco Bay Bridge with easy on-street parking. Whether you're seeking a charming primary residence, second home, or investment property, this is a rare opportunity to own a truly special piece of Portland real estate.

259 York St Unit 1, Portland

Listing courtesy of Portside Real Estate Group.

$680,000
4 Beds ⋅ 2 Baths
In the same family since 1959, this 1929 'four square year-round residence provides roomy comfort throughout. There are 4 true bedrooms and 2 full baths. The convenient Island location is a short walk to the Ferry. The home retains many original features such as a gracious mahogany center staircase, period molding, and functioning original cast iron radiators. It has been improved with vinyl siding, newer windows, and roof. The property's future envisions many possibilities for new owners including: Continued use as a primary residence, suited to a large or growing family; Conversion to various forms of rental investment; Enjoyment as a family summer getaway, from near or afar. Whatever use the future holds for this home, it comes with all the benefits the Peaks community offers to those who spend time on 'The Island', as either resident or visitor: Welcoming Natural Beauty, Serenity, History, and Friendship. House is being sold in 'as is' condition. Photo of local painting by the long time previous owner is meant only to emphasize the positive influence of the Island setting inspiring the creative spirit. Painting is not included with a sale.

24 Central Ave, Portland

Listing courtesy of Bona Terra Realty.

$305,000
2 Beds ⋅ 1 Baths
Perched above-it-all in Bayside, this freshly painted penthouse condo has city views, including the iconic Time and Temp Building. Occupying the entire third floor, this quiet, light-filled two-bedroom home feels like a private treetop retreat--yet it's just moments from everything on the Portland peninsula. Enjoy the convenience of a reserved on-site parking space located directly in front of the entrance. A welcoming entry to the unit begins with lovely hardwood stair treads, leading to a thoughtfully designed landing complete with a custom, extra-large wooden storage chest. Inside, warm wood flooring enhances the natural light throughout the living spaces. The kitchen was fully renovated in 2019 and features tall cabinetry, quartz countertops, cast iron apron-front sink, stainless steel appliances, modern lighting, and clever shelving solutions. Both bedrooms are spacious and bright, each offering generous closet space. Efficient and easy to heat, the unit is equipped with a Rinnai natural gas direct-vent system, supplemented by electric baseboard heating. Additional updates include a high-efficiency water heater installed in 2020. A convenient coin-operated laundry is located in the association's adjacent building on Parris Street. The association completed a major basement structural overhaul in 2022, reinforcing the long-term integrity of the building. This home represents exceptional value on the peninsula--whether you're seeking a pied-à-terre, looking to build equity, or embracing an accessible urban lifestyle. Experience the vibrant energy of historic Bayside, a neighborhood undergoing exciting residential and commercial revitalization.

58 Portland St Unit 5, Portland

Listing courtesy of Coldwell Banker Realty. 207-773-1990
$499,000
3 Beds ⋅ 2 Baths
At the Ledges in Portland's highly sought after Rosemont neighborhood, you'll find a rare combination of natural beauty, thoughtful design, and everyday convenience. Constructed around gorgeous natural ledge, inspired by historic New England architecture, yet built with the efficiencies and comforts of modern construction, The Ledges is a neighborhood that feels natural, effortless and timeless from the moment you arrive. Inside, this townhome lives with the ease and scale of a single-family home. With no one living above you, it is quiet and cosy. Sunlight filters through generous living spaces designed to adapt to the way you live, including a first floor bedroom and full bath. The oversized primary suite provides a comfortable retreat at day's end. And if you somehow find you need more square footage, there's walk up attic for plenty of storage or ready for adding finished space. Think morning coffee on the private patio, walks with neighbors on the abutting conserved trails, easy sidewalk strolls to Deering Center. And all of this is just minutes from Portland's restaurants, waterfront, arts scene, and everyday amenities.

16 Stoneledge Dr Unit 16, Portland

Listing courtesy of Waypoint Brokers Collective.

$775,000
1 Beds ⋅ 2 Baths
Located in Portland's historic Old Port, this sun-filled corner unit at Chandler's Wharf offers sweeping harbor and city views with eastern, southern, and western exposures. The one-bedroom, 1.5-bath residence has been thoughtfully updated with a remodeled kitchen and baths, new windows, a heating and cooling mini-split system, and new appliances. Enjoy the private deck overlooking the waterfront - an ideal spot to relax and take in the scenery. Property includes garage parking for owner and guest, and is located in a gated community. Experience a walkable urban lifestyle in the heart of Portland, just steps from the city's vibrant restaurants, shops, and waterfront attractions.

715 Chandlers Wharf, Unit 715, Portland

Listing courtesy of Town & Shore Real Estate. 207-773-0262
$699,000
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.

$822,589
2 Beds ⋅ 2 Baths
Life Re-Imagined! Building 3, Stevens Square at Baxter Woods! This growing new neighborhood is on its way to be one of the most exciting places to live in Portland Maine! Stevens Square represents Portland's first 55+ condominium community adjacent to hundreds of acres of woods and walking trails. Complete with convenient dog washes, crackling fire pits, and available community center with saltwater pool and gym, this 2nd floor south facing unit has it all. Nicely balanced living spaces focused with designer chosen appointments, including ensuite bedrooms, private deck and lots of wonderful light. This unit faces the beautiful and protected Baxter Woods. Enjoy the large gathering room and sky deck at your fingertips. Covered parking and storage also included. A well-rounded life begins at the Square!

75 Mcauley Way Unit 205, Portland

Listing courtesy of Gardner Real Estate Group.

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