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$949,000
3 Beds ⋅ 2 Baths
Brilliant West End Federal style home proudly perched above the Fore River, offering glimpses of the bustling port below. Bathed in sunlight and historic charm, this property showcases 19 years of stewardship by the same family. Every surface of this home has been mindfully restored, each improvement artfully executed to honor its history and character. Offering sun drenched living spaces anchored by gleaming wide board pine floors, preserved plaster walls and lovely 6 over 6 windows. With three bedrooms, one and a half baths, laundry room, bonus 3rd floor den, backyard garden and off-street parking with EV charging. The vaulted kitchen features radiant concrete floors and orients to the semi-enclosed garden complete with fruit trees and vegetable beds. The wood burning stove centers the cozy living room, a must for any Maine house. Both full and half baths have been updated with tasteful selections including a marble tile glassed in shower, William Morris wallpaper and unlacquered brass fixtures. A modern FHW heating system and spray foam insulated basement provide consistent and efficient comfort. Just moments from local West End favorites including Smalls, Ocotillo, Zu Bakery, Ugly Duckling and walkable to Reiche and Waynflete Schools. The next custodians of 25 Summer Street will be lucky to call this one home. *Showings begin Tuesday 9/15.

25 Summer St, Portland

Listing courtesy of Keller Williams Realty.

$595,000
2 Beds ⋅ 2 Baths
Come and see the magnificent views from this 8th floor double balcony unit. Priced under value for up-grades. You can see all of Portland's harbor where you can sit and enjoy all of the comings and goings from small boats to yachts to cruise ships. Walking trails, marinas, parks, tennis, pickleball courts, food trucks and the best restaurants are right outside your door and the views oh my! All this while your tucked away in your secure building giving peace of mind that the HOA covers water, sewer, heat, hot water, cable you just have your CMP bill to worry about, and you can just call maintenance for any problems you might have. Never to shovel or scrape a windshield again with 2 reserved underground parking spaces. You also have a community room, library and a gym 2 storage units and let's not forget the rooftop deck to watch the fireworks from. The best view in all of Portland!

45 Eastern Promenade Unit 8F & 8G, Portland

Listing courtesy of EXP Realty.

$1,500,000
3 Beds ⋅ 3 Baths
Experience island living at its best on Great Diamond Island. Privately sited overlooking Diamond Cove and the marina, this 3 bedroom, 2.5 bathroom home offers 1,692 square feet of inviting coastal living and an impressive 184 feet of water frontage. The open kitchen and dining area flow into a comfortable living room with a wood-burning fireplace, while the spacious wraparound deck takes full advantage of the cove views. A primary suite and two additional bedrooms provide comfortable accommodations for family and guests. Enjoy Diamond Cove's exceptional amenities, including a private pool, tennis courts, gym, miles of walking trails, and common waterfront areas. Originally an 1898 army fort built to protect Portland during the Spanish-American War, Diamond Cove today offers a unique blend of history, natural beauty, and island lifestyle, all just a quick ferry or water taxi ride from Portland's Old Port. Cruise Casco Bay by day, tie up at the marina, and come home to your own private retreat on the Maine coast.

40 Sunrise Ln, Portland

Listing courtesy of Legacy Properties Sotheby's International Realty.

$549,900
1 Beds ⋅ 2 Baths
SELLER INCENTIVE FOR LAST TWO NEW UNITS 3 months condo fees paid by Seller at closing. What does a sustainable Portland lifestyle look like? It looks like Daymark. Life at Daymark is about balance. With a central location on Peninsula, you won't worry about commute times. Park in the secured attached garage, then forget about the car until you want to explore up the coast. With a 98 Walk Score, no car needed for daily errands. Conveniently, store your bike in the secure ground floor Bike Room. At Daymark you will always feel comfortable and breathe easy with top rated heating/cooling & indoor air filtration system in this Pearl Certified New Construction. The inviting common spaces and Daymark Slack channel create community connection with your neighbors, so you won't feel new in town for long. Located in a vibrant urban setting full of city culture and conveniences like award winning restaurants, the Old Port, the waterfront, breweries, Whole Foods, Traders Joes, co-working and art spaces, community gardens, parks, food trucks, rooftop bars, theaters, shops, and tons of events. When you want nature, that is close by too, from beaches, to mountains, marshes, rivers, woods, lakes, etc. At the end of the day, when you're ready for peace and quiet, head up to your gorgeous 6th floor apartment, tastefully designed with quartz counters, European appliances, white oak floors, oversize windows. From sunrise to sunset & into the night, the views of the city skyline and Back Cove will captivate you. This is sustainable Portland Peninsula living. Come find your balance at Daymark.

75 Chestnut St Unit 609, Portland

Listing courtesy of Waypoint Brokers Collective. tyson@waypointbrokers.com
$699,900
2 Beds ⋅ 2 Baths
SELLER INCENTIVE FOR LAST TWO NEW UNITS!! Three months condo fees paid at closing. Welcome to your Portland Skyline view. Life at Daymark is about balance, where you truly can have it all. With a central location on Peninsula, you won't worry about commute times. Park in the secured attached garage, then forget about the car until you want to explore up the coast. With a 98 Walk Score, no car needed for daily errands. Conveniently, store your bike in the secure ground floor Bike Room. At Daymark you will always feel comfortable & breathe easy with top rated heating/cooling & indoor air filtration system in this Pearl Certified New Construction. The inviting common spaces & Daymark Slack channel create community connection with your neighbors, so you won't feel new in town for long. Located in a vibrant urban setting full of city culture & conveniences like award winning restaurants, the Old Port, the waterfront, breweries, Whole Foods, Traders Joes, co-working & art spaces, community gardens, parks, food trucks, rooftop bars, theaters, shops, & tons of events. Nature is close by too, from beaches, to mountains, marshes, rivers, woods, lakes, etc. For peace & quiet, head up to this sixth floor oasis overlooking Back Cove with breathtaking sunset views from the private corner balcony. Your personal style will shine in the sleek living space with bright natural light, tall ceilings, clean lines, open kitchen, highly rated Viva cabinets, quartz countertops, European appliances. Daymark gives you sustainable & beautiful Portland living. The perfect balance.

75 Chestnut St Unit 607, Portland

Listing courtesy of Waypoint Brokers Collective. tyson@waypointbrokers.com
$875,000
3 Baths
Exceptional 2-unit multi-family in the heart of Portland's Parkside neighborhood! This rare peninsula property is perfect for an owner-occupant or investor, offering highly coveted private outdoor spaces for both units. The 1st-floor unit features 2 bedrooms and steps directly out to an exclusive, private garden oasis—an ideal urban retreat. The upper unit is a sprawling 3-bedroom, 2-level townhouse spanning the 2nd and 3rd floors. Its crowning jewel is a spectacular private rooftop deck boasting views overlooking Back Bay. Enjoy a highly walkable location just moments from Deering Oaks Park, local bakeries, renowned dining, Maine Medical Center and the scenic Back Cove trails. A standout investment where every unit boasts its own private sanctuary!

106 Sherman St, Portland

Listing courtesy of Keller Williams Realty.

$699,000
3 Beds ⋅ 4 Baths
Exceptional Ocean Ridge townhome perfectly positioned for sweeping easterly views over Casco Bay and its islands. Beautifully upgraded and fashionably reimagined, the Kitchen Cove Design renovation brings on the ''wow'' factor with soft-toned cabinetry and granite, generous center island, comfy banquette dining and premium appliances sparking culinary creativity at every level. The open-concept living space anchored by a cozy gas fireplace in the living room features expansive windows and hardwood floors throughout! Step onto the private sundeck to enjoy gentle ocean breezes, morning coffee or al fresco dining. Organized pantry storage, coat closet and a powder room complete the main floor. The second level boasts two bedrooms with expansive windows drawing your eyes to the water and islands, walk-in closets, hardwood floors and a common full bath - plus a separate laundry area. The private third-floor primary suite features vaulted ceilings, hardwood floors and dramatic views--sunrises to start your day and reflective sunsets to end it. The redesigned spa-inspired bath includes radiant heated flooring, spacious glass/tile step-in shower and generous vanity storage. The fully finished daylight lower level expands your living space with a family room, full bath and direct access to a private patio and well-maintained lawn--ideal for guests, home office, movie night or personal home gym. Enjoy the covered wrap-around porch and the convenience of an attached garage that enters into a tiled mudroom. Major system upgrades include a Heat Pump with 5 Mitsubishi ductless mini-splits for year-round comfort and a Bosch boiler for heat and hot water. This lock-and-leave lifestyle offers low maintenance, high comfort and unbeatable proximity to Portland's vibrant downtown--renowned restaurants, marinas, music and theater venues, professional sports and miles of Portland Trails. A perfect blend of coastal beauty, modern upgrades and effortless living.

50 Ridge Rd Unit 4, Portland

Listing courtesy of Coldwell Banker Realty. 207-773-1990
$785,000
2 Beds ⋅ 2 Baths
Perched atop Munjoy Hill, offering glimpses of Casco Bay, this updated condo is brimming with bonuses: Roof rights! A garage! Two gorgeous full baths! An airy deck that catches the sea breeze all summer long! This exceptional condo also enjoys in-unit laundry, heat pump heating and cooling, an enormous storage room, plus basement storage. The updated kitchen features an harmonious palette of maple cabinets and golden granite, along with stainless steel appliances. The efficient layout incorporates a breakfast bar. An adjoining dining room makes for easy entertaining, and grants access to a big, tree-top deck. (Grilling is permitted on the deck!) On the south side of the home, a large living room enjoys bright sun all year long. The original dining room adds flex space for a den, playroom, or office. (This home was built as a three-bedroom flat; sellers converted the bedroom nearest the kitchen to a dining room.) A pair of bedrooms offer glimpses of Casco Bay. Two full bathrooms, with custom tile finishes, deliver a level of luxury almost never found in condos with this level of antique character. Off the rear stairway, you'll find another rarity. A very large storage room that could be... Pantry? Palatial walk-in closet? Office or workout space? And then, those deeded roof rights: What will you create up there, with panoramic views of Casco Bay and the city skyline? The grounds include off-street parking, plus the garage, and a modest lawn. Two blocks northeast is the magnificent Eastern Promenade, with its stunning vistas, food trucks, concerts, ball courts, and Portland's extensive trail system. A few minutes' walk west delivers you to the booming Washington Avenue, where restaurants, coffee shops, boutiques, and specialty markets are creating a brand new village center. A 20 minute walk brings you to the Old Port; a 15 minute drive takes you to the airport. The condo association is non-smoking, responsibly operated, and pets are welcome! Pre-inspection available.

61 Montreal St Unit 3, Portland

Listing courtesy of Cottage & Co Real Estate.

$470,000
3 Beds ⋅ 1 Baths
Perfectly positioned across from beautiful Back Cove, this rare 3-bedroom Ricker Park condo delivers the kind of gracious Portland living you've been looking for. Hardwood floors and crown molding speak to the beautifully preserved vintage character that makes this building so special, and a sunny exposure keeps things bright throughout. The living areas features Back Cove views and the kitchen has been recently updated with new cabinets, flooring, countertops and appliances. All three bedrooms features generous closets and plenty of sun from morning to evening. One outdoor parking spot is included with the option to rent a space in the heated parking garage - only $60/month! There is a strong, friendly HOA and your condo dues include heat and hot water, professional on-site management and more. Downsizing? Enjoy a very large assigned storage room in the basement. Walk out your door to miles of trail along the cove, and you're just minutes from Payson Park's tennis courts, pickleball, and more - with all of downtown Portland a 10-minute walk or a 2-minute drive away.

290 Baxter Blvd Unit E2, Portland

Listing courtesy of Vitalius Real Estate Group, LLC.

$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.

$2,943,000
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.

$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.

$425,000
1 Beds ⋅ 1 Baths
Wake up to sweeping, unobstructed views of Casco Bay from this exceptional 11th-floor condo at Portland's iconic Portland House. Set alongside Fort Allen Park and the Eastern Promenade, this prime location puts the best of Portland right outside your door--from waterfront walks and nearby beaches to Portland Trails and the Old Port. Enjoy the ease of condominium living with an HOA that includes onsite property management, attended security, heat and hot water, basic cable, high-speed internet, heated parking, and trash/recycling. In warmer months, the beautifully landscaped shared patio and gardens provide a spectacular place to relax and take in the bay views. A rare opportunity to experience Portland waterfront living with convenience, amenities, and an extraordinary backdrop.

45 Eastern Promenade Unit 11A, Portland

Listing courtesy of Keller Williams Realty.

$1,575,000
7 Baths
Welcome to 80 Wilson Street, a seven unit on the corner of Wilson and Atlantic Street, atop Portland's Munjoy Hill- just steps to the Eastern Promenade and the East End's restaurants and coffee shops. Enter the front door of 80 Wilson to access six of the seven apartments and the basement which has shared laundry and dedicated storage for each unit. The first floor hall has entry to two one bedroom units, the second floor has an additional three one bedroom units, and the third floor boasts a spacious two bedroom, with views, that make you pause, of the harbor and Portland Headlight. It also has an adjacent unfinished attic space over the ell- which could potentially be converted to additional living space or possibly an inverted deck to fully capture the amazing harbor views. The remaining unit(3) is tucked away around the corner off of Atlantic Street, with its own private parking, fenced in yard space and private entrance. This unit lives and feels like its own place. 80 Wilson makes a solid investment on Munjoy Hill, (location, location, location) with a cash on cash return in the high 9 percentage rate. The current owner has kept up with rent increases thus rents at market rate reducing the effect of Portland's Rent Control. Owner reports this is his easiest building to keep 100% occupied and has not experienced any vacancy during his five plus years, speaks volumes to the desirability of the location.

80 Wilson St, Portland

Listing courtesy of John Graham Real Estate.

$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..

$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
$1,625,000
3 Beds ⋅ 3 Baths
Perched on the fourth floor of The Verdante at 99 Federal Street, Unit 403, this exceptional condominium showcases sweeping 180-degree sunset views across Portland's skyline from a sophisticated, contemporary residence. Perfectly positioned where the vibrant Old Port meets the charming East End, the location offers the best of downtown living with the feel of an established neighborhood. Inside, soaring ceilings, refined finishes, and an open-concept design create a bright, inviting atmosphere ideal for everyday living and entertaining. This thoughtfully designed three-bedroom, two-and-a-half-bath home combines luxury with convenience, featuring elevator access and energy-efficient building systems throughout. The spacious primary suite overlooks Casco Bay, providing a peaceful retreat, while a private balcony off the dining area offers the perfect spot to enjoy ocean breezes and spectacular evening sunsets. Every detail has been carefully considered, from the in-unit laundry, dry bar, and walk-in pantry to the electric blinds and abundant storage, including three walk-in closets and a dedicated storage unit. A rare bonus in the heart of Portland, the home also includes two deeded parking spaces. Residents of The Verdante enjoy an impressive collection of amenities designed to enhance daily living, including a rooftop terrace with panoramic ocean views, dining and lounge areas, a fully equipped fitness center, a private guest suite with bedroom and bath, generator backup, and a beautifully designed lobby highlighted by a living plant wall. Offering a seamless blend of modern luxury, comfort, and convenience, this remarkable residence places Portland's acclaimed restaurants, boutiques, waterfront, and cultural attractions just moments from your door.

99 Federal St Unit 403, Portland

Listing courtesy of Portside Real Estate Group.

$364,900
2 Beds ⋅ 1 Baths
Elegant. Charming. Old World...like a movie set for a Hollywood blockbuster from the 1930's. But updated with all our modern comforts. Beautiful cabinetry in the kitchen, with granite counters and Bosch appliances. Walk-in tiled shower in the bathroom. Views of city sunsets, Back Cove and even Mount Washington. Birdcage elevator, storage and laundry in the basement, lovely private garden spaces for gatherings or peaceful contemplation in the heart of the arts district. And, pets are allowed with Deering Oaks at the bottom of the hill for romps with your furry friend. Walk to your favorite Portland places...the State Theater, Museum of Art, great restaurants and coffee shops. You should see this one!

180 High St Unit 64, Portland

Listing courtesy of Coldwell Banker Realty. 207-773-1990
$1,500,000
3 Beds ⋅ 3 Baths
Perched on a knoll overlooking the Atlantic Ocean, this extraordinary Cliff Island retreat has been the backdrop for generations of cherished memories and is ready to welcome its next chapter. Set on a picturesque half-acre parcel, the property offers breathtaking panoramic water views, a private sandy cove perfect for swimming and wading, classic Maine rocky ledges, open lawns for games and gatherings, and a wooded perimeter that provides exceptional privacy. The 1,585-square-foot main home features two bedrooms, two bathrooms, a spacious living room, and a welcoming dining area, all designed to capture the beauty of the surrounding coastline. A charming one-bedroom, one-bath guest cottage provides comfortable accommodations for family and friends or the perfect space for extended stays. Step outside onto the expansive oceanside deck and enjoy everything from warm summer afternoons to the peaceful beauty of fog rolling across Casco Bay. Whether you're entertaining guests, enjoying your morning coffee, or simply taking in the ever-changing seascape, the setting is nothing short of spectacular. One of the property's most remarkable features is its rare deep-water access. Historically, the home was served by a private wharf that extended directly from the existing deck. As shown on the survey, the wharf may be rebuilt, offering an exceptional opportunity for direct boat access--an amenity found on very few island properties. Rich in history, this special home also served as the private retreat of legendary actress Bette Davis during the filming of The Whales of August in 1986, adding a unique piece of Maine cinematic history to an already remarkable property. Whether you're searching for a seasonal escape, a family compound, or a peaceful waterfront sanctuary, this is a rare opportunity to own one of Cliff Island's most distinctive oceanfront properties. Additional photos arriving next week.

195 Beach Rd, Portland

Listing courtesy of Better Homes & Gardens Real Estate/The Masiello Group. 207-590-6026
$2,100,000
2 Beds ⋅ 1 Baths
A truly rare offering on Great Diamond Island, 218 West Shore Drive is a year-round waterfront property where Maine island living, extraordinary history, and unforgettable sunset views converge. Part of historic Fort McKinley, a coastal defense installation constructed between 1890 and 1910 to protect Portland Harbor, the property occupies a commanding waterfront position with sweeping views toward the Portland skyline. Set on almost 3 acres with 266 feet of water frontage, and including an approved buildable house lot, it offers a meaningful connection to both the island's storied past and the surrounding seascape. The charming cottage is attached to an original mining casemate and features an inviting living area opening to a waterside patio, two bedrooms, and one bath, with the primary bedroom located within the original casemate. Additional historic structures include a renovated second bunker, currently used as a den/office and a workshop with potential for a third bedroom, as well as a rangefinder station and gun battery. Tucked along a private cove with beautiful westerly sunset views, this one-of-a-kind property offers privacy, character, and a remarkable connection to the sea. As part of the Diamond Cove Association, residents enjoy amenities including a pool, tennis and pickleball courts, a bowling alley, and a basketball court. Accessible by ferry or private boat, Great Diamond Island also offers a marina, an inn, and restaurants, creating an exceptional opportunity for year-round island living just minutes from Portland.

218 W Shore Dr, Portland

Listing courtesy of Town & Shore Real Estate. 207-773-0262
$1,190,000
2 Beds ⋅ 3 Baths
Experience one of Portland's most coveted waterfront settings at Chandler's Wharf, where the energy of the Old Port meets the beauty of Casco Bay. Meticulously renovated throughout, this exceptional townhouse offers 2 bedrooms, 2 full bathrooms, and a half bath. The custom kitchen features Calacatta marble countertops, bespoke oak cabinetry and paneling, and a curated collection of premium appliances including a Wolf gas range, Sub-Zero refrigerator, and Miele dishwasher. The living room, centered around an Ortal gas fireplace, opens to a private deck overlooking the harbor, where boats and Portland's iconic working waterfront create an ever-changing view. Upstairs, the primary suite offers a beautifully appointed bath with heated floors, including a heated shower floor. A versatile loft provides space for a home office, media room, fitness area, or guest accommodations. Exceptional custom millwork and thoughtful craftsmanship are evident throughout, while two covered garage parking spaces provide a level of convenience rarely found in the Old Port. Opportunities to enjoy true waterfront living just steps from Portland's acclaimed restaurants, boutiques, galleries, and marinas are exceptionally rare.

512 Chandlers Wharf, Unit 512, Portland

Listing courtesy of RE/MAX By The Bay.

$575,000
2 Beds ⋅ 2 Baths
Exceptional value on Munjoy Hill with this bright, well maintained two bedroom, two bath condo offering sweeping views of Casco Bay and effortless Portland living. Conveniently located on the first floor offering an open floor plan with hardwood and tile flooring, generous in unit storage, and a private primary suite. Located in the secure, elevator and ramp accessible Portland House, residents benefit from heated garage parking, concierge services, onsite gym, community room with lending library, and a beautifully kept outdoor patio with seating overlooking the bay. Most utilities included in HOA fee, including heat, hot water, water/sewer, cable and internet, making ownership simple and predictable. Just steps from the Eastern Promenade, you'll have immediate access to over 70 acres of green space, the Eastern Prom Trail, Fort Allen Park, tennis and pickleball courts, East End Beach, food trucks, and Portland's iconic waterfront. The building's lobby and community spaces have been recently renovated creating a welcoming feel. Residents also enjoy access to the rooftop 'Red Carpet' area for spectacular views of fireworks, cruise ships, and the harbor. A rare opportunity to enjoy convenience, amenities, and one of Portland's most coveted locations.

45 Eastern Promenade Unit 1C, Portland

Listing courtesy of Portside Real Estate Group.

$2,250,000
5 Baths
Mixed-use investment opportunity in Portland's desirable East End, an area that continues to see strong growth and investment. This four-unit property features three residential apartments and one commercial space, offering a combination of strong rental income, flexibility, and long-term value. The residential units include a completely renovated 2-bedroom, 1-bathroom apartment with a bonus room, a 2-bedroom, 1-bathroom apartment, and a renovated 3-bedroom, 2-bathroom apartment. Extensive capital improvements include a new roof (2023), new siding, new windows, three new heat pumps, updated plumbing and electrical systems, renovated kitchens and bathrooms, and substantial improvements to the commercial space. The commercial unit offers a versatile blank canvas with several approved uses, including food & beverage, office, retail, and more, with a renovated shell ready for customization. This flexible commercial component offers an opportunity to tailor the space to a variety of uses while complementing the property's existing residential income. Steps from the Roux Institute, Eastern Promenade, East End Beach, the Old Port, Portland's waterfront, and countless restaurants, breweries, coffee shops, and local retail shops. This is a rare opportunity to acquire a well-improved mixed-use asset in a growing Portland neighborhood with strong fundamentals and continued upside. Showings by appointment only. Please allow a minimum of 48 hours' notice. Please see the attached list of capital improvements for a summary of recent renovations and upgrades.

69 Newbury St, Portland

Listing courtesy of Harborview Properties, Inc..

$899,000
3 Beds ⋅ 2 Baths
Some homes provide a place to stay. Others become the place everyone wants to gather. Perched on the cherished north end of Peaks Island, just moments from the shoreline of Casco Bay, 45 Centennial Street is one of those rare places where the pace slows, memories are made and every season brings something worth looking forward to. Mornings begin with coffee on the second-floor balcony as the sun rises over the bay. Days are spent exploring the water or wandering quiet island roads. Evenings end beneath brilliant stars, the harbor replacing the noise of everyday life. Originally built in 1900 and thoughtfully updated, this year-round New Englander blends historic charm with contemporary comfort. Rich wood floors, a granite kitchen, open living and dining spaces, inviting bedrooms including a classic bunkroom, an updated bath and efficient heat pumps create a home that is as comfortable in January as it is during the height of summer. Outside, a workshop shed opens up possibilities for artists, makers, remote work, storage or weekend projects. Mooring opportunities are available by application through the Portland Harbormaster, while nearby kayaking, boating and fishing make the water an extension of your backyard. Minutes bring you to the ferry, local cafés, lobster rolls, tennis courts, live music and the welcoming village that has made Peaks Island one of Maine's most treasured communities. Offered fully furnished, 45 Centennial Street isn't simply move-in ready, it's ready to be lived in from the moment you arrive. Whether you're searching for a year-round home, a seasonal retreat or a gathering place for the people who matter most, see what island living feels like from the inside.

45 Centennial St, Portland

Listing courtesy of Portside Real Estate Group.

$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.

$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.

$879,000
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.

$975,000
Rarely does an opportunity like this come along. This private building site is located on Peaks Island, one of Casco Bay's most beloved islands. 109 Reed Avenue offers one of the last remaining direct waterfront lots on the island. The 0.92 acres of land consists of 458 ft of ocean frontage with a rocky beach on a protected cove that feels worlds away from the mainland, yet is just a short ferry ride from the heart of Portland. Tucked at the end of a quiet gravel road, the property offers an elevated ridge with commanding views, mature woodlands, and an open lawn with access to Josiah's Cove. Watch lobster boats, ferries, and sailboats drift by from this serene setting. The lot has been surveyed and perk tested, conservation land abuts the property ensuring lasting privacy. Whether you're dreaming of a full-time coastal residence or a summer retreat, this lot is one of the last chances to build something extraordinary on Peaks Island.

109 Reed Ave, Portland

Listing courtesy of Town & Shore Real Estate.

$1,395,000
3 Baths
Enjoy seasonal views of Back Cove and the Portland skyline from this rare three-unit property in one of the city's most desirable locations. Step out your door to the Back Cove Trail for morning walks, or enjoy coffee on your deck while taking in the water views. With strong rental income potential, this property offers the ideal opportunity to offset your mortgage while living in a premier setting. The owner-occupant third floor unit is filled with natural light and features 1 bedroom and 1 bathroom with an open kitchen, dining, and living area. Two private decks extend the living space outdoors, including one with views overlooking Back Cove. The second floor spans the entire level and offers exceptional light throughout. It includes a spacious living room, a separate dining room with original built-ins, a large kitchen, two well-sized bedrooms, and an updated bathroom. A private deck completes this inviting unit. The first floor also occupies the full level and features a sun-filled layout with a spacious living room and gas fireplace, a dining room with built-ins, and an updated kitchen with granite countertops and new cabinetry. This unit also enjoys a private deck for outdoor living. The basement provides dedicated storage for each unit along with coin-operated laundry. Additional amenities include parking for up to six vehicles between parking lot and a rare two-car garage. Numerous updates have been completed in recent years, making this a well-maintained and versatile investment opportunity. A truly special offering on Back Cove that combines location, views, and income potential.

31 Bates St, Portland

Listing courtesy of Vitalius 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.

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