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$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.

$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.

$495,000
3 Beds 4 Baths
Opportunity awaits in Portland's vibrant East Bayside neighborhood! Potential redevelopment. This charming 3-bedroom home is full of character and ready for its next chapter. Featuring a spacious eat-in kitchen, an open and inviting first-floor layout, and a combination of hardwood and tile floors, the home offers a solid foundation with plenty of opportunity to add your own personal style and updates. Enjoy the changing seasons from the enclosed front porch on the first floor, or relax on the open second-floor porch overlooking the neighborhood. Outside, you'll discover a backyard that's as productive as it is beautiful. Established perennial gardens, raised planting beds, and an abundance of edible landscaping--including black raspberries, elderberries, grapevines, and a mature apple tree--create a private urban oasis for gardening enthusiasts and nature lovers alike. Additional highlights include a newer natural gas heating system for efficient comfort and a highly desirable location just minutes from Portland's renowned restaurants, breweries, coffee shops, waterfront, and downtown attractions. Whether you're looking for a primary residence, an investment opportunity, or a home with room to build equity, this East Bayside gem offers incredible potential in one of Portland's most exciting and sought-after neighborhoods.

23 Mayo St, Portland

Listing courtesy of Portside Real Estate Group.

$1,990,000
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.

$499,999
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.

$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..

$949,900
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.

$529,000
4 Beds 2 Baths
Just Listed! Welcome to 13 Hicks Street, a warm and inviting Portland home with charming character throughout. This home offers the space, flexibility, and outdoor living space that appeals to today's buyers. With 4 bedrooms, 1.5 baths, and over 1,500 sq.ft. of living space, this move-in-ready home provides room to grow, gather, work from home, and host family and friends. Inside, sunlight pours through the windows, highlighting beautiful hardwood floors throughout. An updated kitchen with center island, breakfast bar with seating is open to a generous dining area. The spacious living room has a pellet stove for cooler nights! A small mudroom and half bath round out the first floor. Upstairs are four bedrooms and a full bath. The dry basement is great for storage. The outside shines with a large fenced backyard, mature landscaping and great patio area creating the perfect setting for summer barbecues, morning coffee, gardening, and play. The current owners have made meaningful improvements including a new roof, new front and side porches with new exterior doors, new driveway and extensive tree work. Conveniently located in an established neighborhood near local trails, shopping, restaurants, and downtown Portland, 13 Hicks Street offers the ideal blend of comfort, convenience, and classic New England charm.

13 Hicks St, Portland

Listing courtesy of Portside Real Estate Group.

$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..

$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.

$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.

$995,000
4 Beds 3 Baths
From its commanding position high on the lot, this impressive custom Colonial in Portland's desirable Stroudwater neighborhood offers an exceptional combination of space, convenience, and value. Set on nearly ½ acre with mature landscaping, lovely lawns, and an expansive backyard, the property provides privacy, sunshine, and room to enjoy the outdoors. Built in 2003, the home offers 3,391± SF of thoughtfully designed living space. The first floor features a well-appointed eat-in kitchen with island, abundant cabinetry, and space for casual dining. The kitchen flows seamlessly into the living areas, creating an ideal setting for everyday living and entertaining. A formal dining room, spacious front-to-back living room with fireplace, and convenient half bath complete the main level. The second floor offers 4 bedrooms, 2 full baths, and a dedicated laundry room. The oversized primary suite serves as a true retreat with a large walk-in closet and luxurious private bath. Generously sized secondary bedrooms provide flexibility for family, guests, or home office space. The walkout lower level is partially framed and ready for completion, offering outstanding potential for a family room, fitness area, home theater, guest suite, or additional workspace. A rare 3-car attached garage provides ample room for vehicles, storage, hobbies, and outdoor gear. Nature lovers will appreciate nearby access to the Stroudwater and Fore River trail systems, connecting miles of walking paths and protected natural areas. Located just minutes from downtown Portland, Portland International Jetport, I-295, I-95, shopping, dining, and employment centers, this is an ideal home for commuters, travelers, and anyone seeking substantial square footage in one of Southern Maine's most convenient locations.

58 Tide Mill Rd, Portland

Listing courtesy of Benchmark Real Estate.

$1,575,000
6 Beds 5 Baths
141 William Street is a stately John Calvin Stevens Greek Revival combining refined period detail with thoughtful modern updates. Spanning over 6,000 sq ft, this 6-bedroom, 4.5-bath residence offers a generous, traditional layout ideal for entertaining or for those who prefer distinct, separate living spaces. A gracious foyer opens to an expansive formal living room anchored by a central fireplace and a stunning dining room with paneled wainscoting and a wood-burning fireplace. A large, well-appointed pantry leads to a magnificent kitchen completely renovated in 2023, featuring custom cabinetry, stone counters, a tasteful tile backsplash with custom mosaic, and a professional-grade Viking appliance package. The kitchen flows to a sunken back family room and private yard, and connects to a back hallway and rear staircase. The second floor houses four generous bedrooms, including the primary suite, linked by a wide, open hallway. The third floor offers two additional bedrooms, an office, a full bath, and a large cedar closet. The finished basement is an entertainer's dream with a full bar, pool-table space, lounge area, plus a dedicated room ideal for a home gym with an infrared sauna. Lovingly maintained, recent improvements include a new roof, new heating system, added heat pumps, significant electrical upgrades and more, an exceptional blend of historic charm and modern comfort. Located just down the street from the new, gorgeous Crewe Center at University of Southern Maine. Also conveniently located about half a mile from Deering Oaks Park where you can find the local farmers market, as well as Fitzpatrick Stadium for the Portland Hearts Of Pine soccer games, Hadlock Field for the Seadogs games and Portland Expo for the Red Claws basketball games!

141 William St, Portland

Listing courtesy of Portside Real Estate Group.

$799,900
4 Beds 3 Baths
Tucked into one of Portland's most desirable and quiet neighborhoods call Pineloch Woods, this North Deering Colonial is ready for its next chapter. For added convenience, the home can be offered fully furnished, via a separate bill of sale. The heart of the home is an open concept layout, anchored by an updated kitchen with granite countertops. The kitchen flows seamlessly into the dining and family rooms. Relax in the living room and enjoy the warmth of a cozy fireplace. The sole owners took pride in this property, with major updates including replaced roof, no maintenance gutter guards, Anderson tilt in windows and a new high efficiency furnace with a transferable warranty. Location is everything with excellent schools within walking distance, plus shopping, restaurants, and entertainment. Interstates are close by. This is the kind of home where memories are made and the your next chapter is ready to begin.

130 Pineloch Dr, Portland

Listing courtesy of Sell Your Home Services. 888-219-3009

$775,000
3 Beds 2 Baths
Opportunity meets flexibility at 26 Adelaide Street. This thoughtfully renovated property offers three finished levels of living space, a generous backyard, and a RARE BONUS: an additional buildable lot included in the sale. This home blends classic character with modern updates including beautiful wood floors, heat pumps for efficient heating and cooling, and flexible living spaces throughout. With three bedrooms and three levels of finished living area, there is room to spread out whether you're looking for a primary residence, investment property, or a live/work opportunity. Outside, the expansive yard provides space to garden, entertain, or simply enjoy a private outdoor setting rarely found in this area of Portland. Two detached garages offer exceptional storage, workshop space, or future possibilities. The true standout is the property's B2 commercial zoning and included second deeded lot. The lot may offer future development potential including an additional single family home, ADU, multifamily development, or other permitted uses within the B2 district. Buyers are encouraged to perform their own due diligence with the City of Portland regarding zoning, density, and permitted uses. Conveniently located within walking distance of the University of New England's Portland campus, local restaurants, parks, and neighborhood amenities, this is a unique opportunity to purchase not just a home, but future potential in one of Portland's most convenient locations.

26 Adelaide St, Portland

Listing courtesy of Waypoint Brokers Collective.

$449,900
3 Beds 1 Baths
Welcome to 153 Auburn Street! This charming, sun-filled 3-bedroom Cape is nestled in Portland's highly desirable North Deering neighborhood, offering an inviting warmth perfect for everyday comfort. Situated on an expansive lot, the property is surrounded by lush gardens, mature trees, and local wildlife--creating a private oasis that is still just minutes from local schools, shopping, trails, restaurants, and downtown Portland. The flexible floor plan effortlessly adapts to your lifestyle, featuring hardwood, tile, and carpeted flooring throughout. On the main level, enjoy a bright, sunlit living room, a spacious dining room, and a kitchen with ample cabinet storage. This level also hosts a comfortable bedroom, a full bath, and a versatile bonus room perfect for a home office, playroom, or even a 4th bedroom, allowing for easy single-level living. Just off the back, a beautiful sunroom with large windows overlooks a spacious deck and the sprawling backyard. Upstairs, two additional bedrooms offer cozy, private retreats for family or guests. Built in 1947, this home also includes a 2-car garage and a full basement with incredible potential for storage, hobbies, or future finished square footage. A must-see property packed with opportunity!

153 Auburn St, Portland

Listing courtesy of The Collective Real Estate Co.

$640,000
3 Beds 3 Baths
Beautifully updated North Deering cape with energy-efficiency! Welcome to 31 Samuel Road, a meticulously maintained and thoughtfully updated Cape located in Portland's highly sought-after North Deering neighborhood. Renovated in 2022, this charming 3-bedroom, 3 bath home blends classic character with modern comfort and efficiency. Inside, you'll find over 2,200 square feet of inviting living space featuring hardwood floors, granite countertops, a cozy gas fireplace, and a finished lower-level family room perfect for entertaining, working from home, or relaxing with family and friends. The home's bright and functional layout offers flexibility for today's lifestyle while maintaining a warm, welcoming feel throughout. Recent upgrades include two high-efficiency heat pumps providing both heating and air conditioning, ensuring year-round comfort. Solar panels help significantly reduce energy costs, with the current owners enjoying virtually no electric bills from July through September. A valuable benefit that combines sustainability with long-term savings. Enjoy the large, screened in back porch overlooking a beautifully landscaped private, fenced backyard. Comes complete with a patio and hot tub, ideal for outdoor gatherings or quiet evenings at home. Also featured, an oversized attached two-car garage and spacious breezeway. The property is situated on a generous lot close to shopping, restaurants, schools, parks, and trails. It is a move-in-ready home that is an exceptional opportunity to enjoy comfort, efficiency, and convenience in one of the city's most desirable neighborhoods.

31 Samuel Rd, Portland

Listing courtesy of Century 21 North East.

$1,400,000
3 Beds 2 Baths
Located on a corner lot on coveted Munjoy Hill, 42 Montreal Street is an impeccably renovated, single family house with three bedrooms and two bathrooms. This high quality renovation features copper flashing and downspouts, cedar clapboard siding, a red cedar shingle roof, and a meticulously rebuilt historic cupola. Water views and sweeping vistas of Casco Bay create a stunning backdrop, while the cupola provides a perfect perch for watching summer fireworks over the harbor. Inside, hardwood floors and thoughtfully preserved architectural details blend timeless character with everyday comfort. Outside, a glorious private garden filled with roses and perennial plantings offers exceptional privacy and beauty, creating an extraordinary urban oasis. Multiple outdoor living areas invite entertaining, relaxing, and enjoying Maine's seasons. This absolutely charming mansard-roof cottage enjoys a quiet, private pocket of Portland's East End, just steps from parks, trails, restaurants, shops, and the waterfront. Walk to tennis courts, a boat launch, and a sandy beach, embracing the very best of the East End lifestyle. Beautifully cared for inside and out, this special property offers a rare opportunity to enjoy Portland's vibrant coastal lifestyle from one of Munjoy Hill's most desirable locations.

42 Montreal St, Portland

Listing courtesy of Town & Shore Real Estate. 207-773-0262

$549,900
5 Beds 3 Baths
If you need room, this is the house. It has 5 bedrooms and 3 bathrooms , including two beds and a bath that make up a private wing on the first floor that would be perfect an in-law suite, at home offices , guest bedrooms, gym, etc. You will fall in love with the recently meticulously renovated kitchen and some of the artistic touches including the multicolored metal roof. Set in a perfect location with driveways and frontage on both Summit and Lambert Street. The garage offers extra storage or a place to keep the car on a cold and snowy nights. The location, near the turnpike, the Old Port, Riverside Golf Course, shopping, and more is ideal. Don't forget the generator, that will keep the lights on when on stormy nights.

517 Summit St, Portland

Listing courtesy of Maine Values Real Estate.

$2,200,000
7 Beds 6 Baths
In real estate, it is often said that location is everything. The challenge, of course, is that the best locations were claimed long ago. For most buyers, that means finding a property with potential and transforming it into something special. Here, that work has already been done. Perched in one of Portland's most coveted locations overlooking the Western Promenade, this extraordinary residence combines an irreplaceable setting with over fifteen years of thoughtful renovation and restoration. The result is a seamless blend of historic character and modern comfort, creating a home that honors its past while meeting the needs of contemporary living. Imagine ending your day on the porch, overlooking the park and enjoying spectacular sunsets. Open the windows and doors and allow the ocean breezes to flow throughout the home. There is a feeling here that is difficult to describe and impossible to replicate--a sense of history, craftsmanship, and place that makes this property truly exceptional. Designed to be both grand and comfortable, the versatile floor plan offers spaces that can evolve to fit your lifestyle. The home features five bedrooms with A/C, four and a half baths, a stately library or office, formal living and dining rooms, a chef's kitchen, and a butler's pantry. Every room is enriched by extraordinary architectural details, including black walnut and quarter-sawn oak woodwork, crystal chandeliers, wainscoting, bay windows, hand-painted murals, leaded glass cabinetry, and stunning stained-glass windows. These remarkable materials and finishes were crafted by artisans whose work has stood the test of time. A private entrance and guest quarters on the third floor provide additional flexibility for extended family, guests, or creative living arrangements. Outside, lush gardens, gracious entrances, inviting porches, and seven off-street parking spaces further enhance the property's appeal--an uncommon luxury in this historic neighborhood.

261 Western Promenade, Portland

Listing courtesy of Roxanne York Real Estate.

$675,000
5 Beds 2 Baths
Wow!!! Nothing wrong with this property, off street parking+++ original features, beautiful woodwork that you just don't find in homes these days! Do you like the charm the Colonial Victorian? Come see this property where timeless charm surrounds you. This home has been well maintained and preserved. Exceptional 5-bedroom home showcasing craftsmanship, original woodwork, and timeless architectural character. Beginning in the entry you'll be captivated by the grand staircase, rich millwork and beautiful stained glass. Move right in or take a moment to bring back the woodwork to its original luster and design the kitchen to match your taste! Natural gas fired furnace, newly replaced water heater, updates to the porch, roof and much more. Entertain friends and family in the spacious living and dining rooms, or in the comfortable sitting room. The expansive unfinished third-floor attic presents incredible potential for expansion. Perhaps a future living space, a studio, office or workshop. Additional features include a full length covered front porch, a large driveway.

271 Woodford St, Portland

Listing courtesy of Keller Williams Realty. 207-415-8995

$729,000
3 Beds 2 Baths
Welcome to 248 Pleasant Avenue on Peaks Island, where classic island charm meets comfortable year-round living. Set on a beautifully landscaped lot, this 3-bedroom, 2-bath home offers a spacious covered front porch, fenced yard, fire pit patio, hot tub, and storage shed creating the perfect setting for relaxing or entertaining. Inside, you'll find warm and inviting living spaces filled with natural light, hardwood floors, and a pellet stove that adds both comfort and character. Seasonal glimpses of Casco Bay can be enjoyed from the property, while nearby beaches, scenic walking trails, local restaurants, and ferry access are all within easy reach. Experience the vibrant Peaks Island lifestyle with easy access to the historic TEIA (Trefethen-Evergreen Improvement Association), a cherished community hub offering sailing, tennis, pickleball, youth camps, arts and cultural programs, fitness classes, live music, lectures, and seasonal events that bring neighbors and visitors together. Whether you're seeking a full-time residence, seasonal getaway, or investment opportunity, this home offers the perfect blend of coastal beauty, community, and convenience--just a short ferry ride from Portland.

248 Pleasant Ave, Portland

Listing courtesy of Berkshire Hathaway HomeServices Verani Realty.

$1,495,000
3 Beds 2 Baths
Buffered by natural beauty and protected land, this remarkable seaside property delights the senses at every turn. The sparkle of the tide, rustle of foliage, salty sea breezes, birdsong, and spectacular sunrises & sunsets create an atmosphere of uncommon tranquility. Set on a generous, sun-drenched lawn just steps from the shore, this 3 BR, 2 BA home blends coastal elegance with timeless cottage architecture. Meticulously maintained, the year-round residence reflects pride of ownership. Water views and natural light grace nearly every room, while quality craftsmanship and tasteful design create spaces that are both beautiful and functional. At the heart of the home, the bright and inviting kitchen encourages effortless gathering. Open to the living and dining areas, it features custom-crafted pantry and buffet cabinetry beneath a vaulted ceiling. A woodstove adds warmth and ambiance on cooler days, while oversized glass sliders frame the picturesque landscape and seamlessly connect the interior to the outdoors. Designed for entertaining and everyday enjoyment alike, the expansive, partially covered deck overlooks the water and extends the living space. Stone patios create inviting destinations for outdoor dining and evening fires by the sea. Whether hosting family & friends or enjoying a quiet moment alone, the setting is simply unforgettable. The primary BR offers a walk-in closet and private balcony w/ outdoor shower overlooking the shoreline. Additional amenities include a 1st flr BR with nearby full BA, a cozy study/artist's nook, 2nd-flr laundry, mud rm. The exterior features high-quality, low-maintenance materials, delightful landscaping, raised garden beds, a charming children's play area complete with sandpit & secret path, and a newly constructed deluxe shed. Enhanced by countless details that elevate it from ordinary to exceptional, this private coastal retreat offers the best of island living. Enjoy easy access to village shops and ferry landing.

17 3rd St, Portland

Listing courtesy of Portside Real Estate Group.

$591,599
4 Beds 2 Baths
Step into the perfect blend of timeless charm and modern convenience in this beautifully maintained 1919 Gambrel-style home on Presumpscot Street in Portland. Featuring 4 bedrooms and 2 bathrooms, this home features a thoughtfully designed layout with a first-floor bedroom, full bath, and laundry--ideal for single-level living or accommodating guests. The inviting farmer's porch welcomes you home and flows into a cozy living room filled with character and warmth. A designated dining room provides the perfect setting for gatherings, while the kitchen seamlessly combines classic charm with modern functionality. Throughout the home, you'll find a wonderful balance of original details and tasteful updates. Upstairs, three spacious bedrooms and a full bathroom provide comfortable living space for bedrooms, guests, or a home office setup. Enjoy abundant storage with separate full basements under both the original home and the addition. Outside, enjoy a beautifully landscaped, level 0.12-acre lot with open yard space perfect for gardening, entertaining, or simply relaxing. Conveniently located under 10 minutes from Portland's vibrant Old Port and downtown districts, this home offers easy access to local restaurants, shops, and waterfront attractions. Outdoor enthusiasts will appreciate the proximity to the Presumpscot River Preserve, Back Cove Trail, and miles of walking, running, and biking trails, along with nearby parks, golf courses, and recreational opportunities. A rare opportunity to own a piece of Portland history while enjoying the conveniences of modern living in one of Maine's most desirable cities. Open House Saturday July 25th from 11:30am-1pm.

64 Presumpscot St, Portland

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

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

4 Oramel Ave, Portland

Listing courtesy of Portside Real Estate Group.

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

495 Allen Ave, Portland

Listing courtesy of Elevate Maine Realty.

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