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Welcome to 104 Brighton Avenue --a charming and spacious five-bedroom Colonial that blends timeless character with thoughtful modern updates. This bright and inviting home offers 2.5 baths, including a private en suite off the primary bedroom, creating a comfortable retreat within the home. Classic details shine throughout, complemented by recent improvements that make everyday living both efficient and enjoyable. Updated heat pumps provide year-round comfort, while solar panels add an eco-conscious and cost-saving element. The home's layout offers flexibility for a variety of lifestyles, whether you need extra bedrooms, home office space, or guest accommodations. At the heart of the home, the kitchen features updated appliances and offers a welcoming space for cooking and gathering. Natural light fills the interior, enhancing the home's warm and airy feel. The living spaces strike the perfect balance between traditional Colonial charm and modern livability. Step outside to discover a sweet, manageable backyard--ideal for relaxing, gardening, or entertaining on warm Maine days. The outdoor space feels like a private oasis while still being conveniently located. Positioned just minutes from downtown Portland, this home offers easy access to the city's renowned dining, shopping, and waterfront. Even more, it is within walking distance to the University of Southern Maine and nearby Portland Hearts of Pine soccer games, making it a fantastic location for those who enjoy being part of a vibrant community. 104 Brighton Avenue is a rare opportunity to own a classic Portland home with modern upgrades, generous space, and unbeatable convenience.

5 Beds ⋅ 3 Baths

Welcome to 104 Brighton Avenue --a charming and spacious five-bedroom Colonial that blends timeless character with thoughtful modern updates. This bright and inviting home offers 2.5 baths, including a private en suite off the primary bedroom, creating a comfortable retreat within the home. Classic details shine throughout, complemented by recent improvements that make everyday living both efficient and enjoyable. Updated heat pumps provide year-round comfort, while solar panels add an eco-conscious and cost-saving element. The home's layout offers flexibility for a variety of lifestyles, whether you need extra bedrooms, home office space, or guest accommodations. At the heart of the home, the kitchen features updated appliances and offers a welcoming space for cooking and gathering. Natural light fills the interior, enhancing the home's warm and airy feel. The living spaces strike the perfect balance between traditional Colonial charm and modern livability. Step outside to discover a sweet, manageable backyard--ideal for relaxing, gardening, or entertaining on warm Maine days. The outdoor space feels like a private oasis while still being conveniently located. Positioned just minutes from downtown Portland, this home offers easy access to the city's renowned dining, shopping, and waterfront. Even more, it is within walking distance to the University of Southern Maine and nearby Portland Hearts of Pine soccer games, making it a fantastic location for those who enjoy being part of a vibrant community. 104 Brighton Avenue is a rare opportunity to own a classic Portland home with modern upgrades, generous space, and unbeatable convenience.

104 Brighton Ave, Portland

Listing courtesy of Legacy Properties Sotheby's International Realty.

$430,000

Welcome to this 3-bedroom, 1-bath single-family in Portland's desirable North Deering neighborhood. Offered for the first time in over 50 years, this home offers 1,120 sq ft , hardwood floors, both a front and back 3 season porch and a layout that is both comfortable and functional for everyday living. Outside, is a large yard--ideal for relaxing, play, or gardening--plus the convenience of a 2-car garage for parking and storage. Tucked on a dead-end road, this home offers a low-traffic setting while staying close to what you need. You will enjoy this walkable neighborhood with shopping nearby and easy access to local trails. While the property is in need of a few repairs and updates, the previous owners lived there comfortably and happily for years. This is a great opportunity for buyers looking to personalize and update at their own pace. Don't miss this great opportunity to own this sweet home in a sought-after Portland location.

3 Beds ⋅ 1 Baths

Welcome to this 3-bedroom, 1-bath single-family in Portland's desirable North Deering neighborhood. Offered for the first time in over 50 years, this home offers 1,120 sq ft , hardwood floors, both a front and back 3 season porch and a layout that is both comfortable and functional for everyday living. Outside, is a large yard--ideal for relaxing, play, or gardening--plus the convenience of a 2-car garage for parking and storage. Tucked on a dead-end road, this home offers a low-traffic setting while staying close to what you need. You will enjoy this walkable neighborhood with shopping nearby and easy access to local trails. While the property is in need of a few repairs and updates, the previous owners lived there comfortably and happily for years. This is a great opportunity for buyers looking to personalize and update at their own pace. Don't miss this great opportunity to own this sweet home in a sought-after Portland location.

37 Daggett St, Portland

Listing courtesy of Allied Real Estate.

$555,000

A rare opportunity in one of Portland's most convenient pockets: THIS PROPERTY INCLUDES AN ADDITIONAL LOT AT 13 UPLAND AVENUE WITH REAL DEVELOPMENT POTENTIAL. Per written confirmation from Portland's zoning office, THE LOT MAY SUPPORT UP TO FOUR DWELLING UNITS, subject to permitting and site review. Whether you're an investor, a multigenerational family, or a buyer looking to build lasting equity and flexibility into your purchase, this is a chance to shape the space to fit your vision. And the location delivers. Tucked onto a quiet dead-end street, you can walk to Back Bay and Payson Park, hop downtown in about five minutes, and enjoy easy on-and-off access to I-295 whenever you need it. The home itself is a well-loved ranch with real warmth. The heart of it is a spacious, light-filled 16'x22' family room with wood floors and a cozy natural gas fireplace, the kind of space made for gathering, relaxing, and everyday living. Three comfortable bedrooms sit on the main floor, while the basement offers flexible bonus rooms perfect for a home office, a newly renovated bathroom with jetted tub, guest space, hobby room, or whatever your life calls for. One of those lower-level rooms even has egress, giving you options as your needs change. Whether you're simplifying, settling in, or looking for a home that keeps life easy and connected, this one delivers location, comfort, and possibility all in one.

3 Beds ⋅ 2 Baths

A rare opportunity in one of Portland's most convenient pockets: THIS PROPERTY INCLUDES AN ADDITIONAL LOT AT 13 UPLAND AVENUE WITH REAL DEVELOPMENT POTENTIAL. Per written confirmation from Portland's zoning office, THE LOT MAY SUPPORT UP TO FOUR DWELLING UNITS, subject to permitting and site review. Whether you're an investor, a multigenerational family, or a buyer looking to build lasting equity and flexibility into your purchase, this is a chance to shape the space to fit your vision. And the location delivers. Tucked onto a quiet dead-end street, you can walk to Back Bay and Payson Park, hop downtown in about five minutes, and enjoy easy on-and-off access to I-295 whenever you need it. The home itself is a well-loved ranch with real warmth. The heart of it is a spacious, light-filled 16'x22' family room with wood floors and a cozy natural gas fireplace, the kind of space made for gathering, relaxing, and everyday living. Three comfortable bedrooms sit on the main floor, while the basement offers flexible bonus rooms perfect for a home office, a newly renovated bathroom with jetted tub, guest space, hobby room, or whatever your life calls for. One of those lower-level rooms even has egress, giving you options as your needs change. Whether you're simplifying, settling in, or looking for a home that keeps life easy and connected, this one delivers location, comfort, and possibility all in one.

11 Upland Ave, Portland

Listing courtesy of Sebago to the Sea Realty LLC.

$2,100,000

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.

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

$640,000

Nestled in Portland's Stroudwater neighborhood on a quiet cul-de-sac, this inviting 3 to 4-bedroom, 2.5-bath offers spacious living in a desirable location. Ideally located just moments from the Portland Trails system, you'll enjoy easy access to miles of scenic walking, running, and biking trails while remaining just minutes from downtown Portland. Inside, a bright and sun-filled living room welcomes you with abundant natural light and a cozy wood-burning fireplace, creating the perfect space to relax or gather with family and friends. The thoughtfully designed layout includes a first-floor primary suite with an en suite bath, offering the ease of single-level living. Additional highlights include a glassed-in sunroom with sliding doors to the backyard, full basement with expansive storage, a two-car garage, generator and plenty of room for family, guests, or a home office. Set in one of Portland's most established neighborhoods, this home offers a wonderful balance of peaceful surroundings, outdoor recreation, and convenient access to shopping, dining, and everything the city has to offer.

3 Beds ⋅ 3 Baths

Nestled in Portland's Stroudwater neighborhood on a quiet cul-de-sac, this inviting 3 to 4-bedroom, 2.5-bath offers spacious living in a desirable location. Ideally located just moments from the Portland Trails system, you'll enjoy easy access to miles of scenic walking, running, and biking trails while remaining just minutes from downtown Portland. Inside, a bright and sun-filled living room welcomes you with abundant natural light and a cozy wood-burning fireplace, creating the perfect space to relax or gather with family and friends. The thoughtfully designed layout includes a first-floor primary suite with an en suite bath, offering the ease of single-level living. Additional highlights include a glassed-in sunroom with sliding doors to the backyard, full basement with expansive storage, a two-car garage, generator and plenty of room for family, guests, or a home office. Set in one of Portland's most established neighborhoods, this home offers a wonderful balance of peaceful surroundings, outdoor recreation, and convenient access to shopping, dining, and everything the city has to offer.

51 Old Mast Rd, Portland

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

$849,000

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.

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.

$385,000

A rare opportunity to own a detached single-family home in Portland at an approachable price point! This classic 1930s Gambrel offers approximately 1,384 square feet of living space with 2 bedrooms, 2 full bathrooms, and a comfortable, functional layout filled with character. Inside, hardwood, tile, and vinyl flooring complement inviting living spaces, while the bright sunroom provides a wonderful spot for morning coffee, reading, plants, or simply relaxing. The home's classic architecture and flexible spaces offer plenty of opportunity to personalize over time while preserving the charm that makes it special. Step outside and discover one of the property's standout features—a surprisingly private, fully fenced backyard. There's room for pets, gardening, entertaining, or creating your own outdoor retreat. Off-street parking adds everyday convenience. For buyers comparing Portland condos, 705 Riverside offers a compelling alternative: your own detached home, private fenced yard, 2 full bathrooms, off-street parking, and no monthly association fee. Convenient access to shopping, restaurants, trails, parks, major commuter routes, and all that Portland has to offer adds to the home's everyday practicality. Offered at $400,000, 705 Riverside Street is ready for its next owner. Come see what single-family homeownership in Portland can look like.

2 Beds ⋅ 2 Baths

A rare opportunity to own a detached single-family home in Portland at an approachable price point! This classic 1930s Gambrel offers approximately 1,384 square feet of living space with 2 bedrooms, 2 full bathrooms, and a comfortable, functional layout filled with character. Inside, hardwood, tile, and vinyl flooring complement inviting living spaces, while the bright sunroom provides a wonderful spot for morning coffee, reading, plants, or simply relaxing. The home's classic architecture and flexible spaces offer plenty of opportunity to personalize over time while preserving the charm that makes it special. Step outside and discover one of the property's standout features—a surprisingly private, fully fenced backyard. There's room for pets, gardening, entertaining, or creating your own outdoor retreat. Off-street parking adds everyday convenience. For buyers comparing Portland condos, 705 Riverside offers a compelling alternative: your own detached home, private fenced yard, 2 full bathrooms, off-street parking, and no monthly association fee. Convenient access to shopping, restaurants, trails, parks, major commuter routes, and all that Portland has to offer adds to the home's everyday practicality. Offered at $400,000, 705 Riverside Street is ready for its next owner. Come see what single-family homeownership in Portland can look like.

705 Riverside St, Portland

Listing courtesy of Excellence Realty.

$1,774,000

A rare opportunity to own a truly distinctive contemporary residence in Portland's coveted West End, now newly priced. Custom-built with an emphasis on architecture, natural light, sustainability, and year-round comfort, 5 Salem Street is a one-of-a-kind home unlike anything else on the Peninsula. Be sure to watch the new property film to experience the architecture, light, and exceptional indoor-outdoor living this home offers. Designed across three levels, the home features 3 bedrooms, 2 full baths and 1 half bath, soaring ceilings, dramatic translucent elements, and a striking two-story light shaft that fills the interior with natural light. Therma-Steel insulated panels, Marvin windows, Boral siding, and Azek trim contribute to its energy efficiency and distinctive design. The spectacular 2026 kitchen features rift-cut oak cabinetry, integrated storage, a statement island, paneled refrigerator, black granite countertops and backsplash, and premium Thermador appliances, including a new natural gas range. An appliance garage, coffee station, custom dining credenza, motorized blinds, and new washer and dryer add thoughtful function. The top floor is crowned by a sun-drenched winter garden beneath skylights and a translucent roof system, capturing abundant natural light and glimpses of Casco Bay. Six covered porches extend the living space outdoors, while an enclosed backyard provides rare private outdoor space. The ground level includes a studio with kitchen, full bath, private entrance, and outdoor space- offering flexibility for guests, a home office, creative studio, or rental use. A climate-controlled garage is a rare Peninsula amenity. Just moments from Portland's restaurants, the Old Port, and waterfront, 5 Salem Street offers an extraordinary opportunity to own a modern architectural masterpiece in one of Portland's most desirable neighborhoods.

4 Beds ⋅ 4 Baths

A rare opportunity to own a truly distinctive contemporary residence in Portland's coveted West End, now newly priced. Custom-built with an emphasis on architecture, natural light, sustainability, and year-round comfort, 5 Salem Street is a one-of-a-kind home unlike anything else on the Peninsula. Be sure to watch the new property film to experience the architecture, light, and exceptional indoor-outdoor living this home offers. Designed across three levels, the home features 3 bedrooms, 2 full baths and 1 half bath, soaring ceilings, dramatic translucent elements, and a striking two-story light shaft that fills the interior with natural light. Therma-Steel insulated panels, Marvin windows, Boral siding, and Azek trim contribute to its energy efficiency and distinctive design. The spectacular 2026 kitchen features rift-cut oak cabinetry, integrated storage, a statement island, paneled refrigerator, black granite countertops and backsplash, and premium Thermador appliances, including a new natural gas range. An appliance garage, coffee station, custom dining credenza, motorized blinds, and new washer and dryer add thoughtful function. The top floor is crowned by a sun-drenched winter garden beneath skylights and a translucent roof system, capturing abundant natural light and glimpses of Casco Bay. Six covered porches extend the living space outdoors, while an enclosed backyard provides rare private outdoor space. The ground level includes a studio with kitchen, full bath, private entrance, and outdoor space- offering flexibility for guests, a home office, creative studio, or rental use. A climate-controlled garage is a rare Peninsula amenity. Just moments from Portland's restaurants, the Old Port, and waterfront, 5 Salem Street offers an extraordinary opportunity to own a modern architectural masterpiece in one of Portland's most desirable neighborhoods.

5 Salem St, Portland

Listing courtesy of Peninsula Real Estate LLC.

$879,900

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.

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..

$945,000

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.

4 Beds ⋅ 3 Baths

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

58 Tide Mill Rd, Portland

Listing courtesy of Benchmark Real Estate.

$1,450,000

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!

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.

$540,000

SELLER OFFERING TO BUY DOWN YOUR INTEREST RATE! Ask how you could take advantage of a special seller-offered financing incentive to enjoy a lower initial interest rate and reduced monthly payments! 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.

4 Beds ⋅ 2 Baths

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

64 Presumpscot St, Portland

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

$1,100,000

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.

2 Beds ⋅ 3 Baths

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

4 Oramel Ave, Portland

Listing courtesy of Portside Real Estate Group.

$896,400

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

5 Beds ⋅ 4 Baths

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

75 Carleton St, Portland

Listing courtesy of Maine Real Estate Co.

$879,999

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

2 Beds ⋅ 1 Baths

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

494 Island Ave, Portland

Listing courtesy of Locations Real Estate Group LLC.

$459,000

This is the best value in its price class for this well maintained shingle-style Dutch Colonial owned and loved by the same family since it was built nearly a century ago, It is ready to create new memories for the next stewards. Owner spent over $25,000 this spring and summer improving the property as indicated in the improvements list. It's a keeper with an enclosed backyard on a dead-end street in Libbytown. Hint: hardwood floors are in great condition under the first floor carpet.

3 Beds ⋅ 2 Baths

This is the best value in its price class for this well maintained shingle-style Dutch Colonial owned and loved by the same family since it was built nearly a century ago, It is ready to create new memories for the next stewards. Owner spent over $25,000 this spring and summer improving the property as indicated in the improvements list. It's a keeper with an enclosed backyard on a dead-end street in Libbytown. Hint: hardwood floors are in great condition under the first floor carpet.

15 Rudman Rd, Portland

Listing courtesy of EXP Realty.

$1,080,000

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

3 Beds ⋅ 2 Baths

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

364 Island Ave, Portland

Listing courtesy of Portside Real Estate Group.

$650,000

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

3 Beds ⋅ 2 Baths

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

17 Elizabeth St, Portland

Listing courtesy of Carey & Giampa, LLC.

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