497 properties for sale in Deering Highlands

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 surrou

True turn-key investment: 6-unit multi-family property offers strong rental potential in updated units and well maintained building and system. The unit mix is 2 x one-bedroom units and 4 x two-bedroom units. Each apartment has a private entrance and separately metered utility for tenant privacy, livability and fewer landlord expenses. A large rear parking lot provides ample off-street parking for residents, and shared laundry in the basement adds everyday convenience. Whether you're growing an existing portfolio or purchasing your first multifamily property, this well-maintained building is the way to add easy-to-own and easy-to-manage units

Developers Take Notice! This oversized lot is approved for development of 7 condo units. Stunning views overlooking the ocean and located in the highly-desirable Munjoy Hill neighborhood on a quiet street. This lot is just waiting for the right developer to bring their vision and be part of the booming development of Portland Maine!

For those seeking something truly distinctive, this Portland penthouse is an exceptional find. This fully renovated third floor condo at 135 Congress Street offers single level living with 360 degree views of Portland and a two level outdoor deck. Completely turnkey and truly one of a kind in the East End. The remodeled kitchen features new cabinetry, a quartzite island and black leathered granite countertops surrounding the range. Recently replaced GE Profile appliances include a gas range with an air fryer, refrigerator and dishwasher, complemented by a new GE hood system. The primary suite includes a walk in closet and a private bathroom with new tile and vanity. Two additional bedrooms and a second full bathroom updated with new tile, tub and vanity provide comfortable space for guests. Hardwood and tile flooring, fresh paint throughout, central air, in unit laundry and one deeded off street parking space complete the offering. Outside, a new Meranti wood screen wall enhances the l

A completely renovated Portland single-family home at a price increasingly difficult to find. 566 Washington Avenue combines move-in-ready condition with a surprisingly functional three-bedroom layout, including a first-floor bedroom, first-floor laundry and 1A½ baths. The bright, open interior features new flooring and finishes, a beautifully updated kitchen with new cabinetry, countertops and appliances, and fully renovated bathrooms with clean, timeless styling. Updated windows, systems, mechanicals and zoned heat pumps provide year-round comfort, efficiency and peace of mind. Additional advantages include public water and sewer, a full basement, off-street parking and the freedom of single-family ownership without a condominium fee. Located in Portland's desirable East Deering neighborhood, the home is convenient to Back Cove, downtown Portland, neighborhood shops and restaurants, and I-295. The expensive work has already been completed-simply move in and enjoy a thoughtfully renov

Opportunity, flexibility, and location come together at 850 Washington Avenue, a beautifully renovated two-unit property in one of Portland's most exciting growth corridors. Situated on over half an acre, this turnkey investment features two spacious 2-bedroom units, a detached 2-car garage, abundant off-street parking, and an expansive backyard, an increasingly rare find within the city. Both units have been thoughtfully updated with timeless finishes including white cabinetry, granite countertops, updated appliances, stylish bathrooms, and in-unit laundry. Separate gas and electric meters, along with newer boilers, make ownership and management simple and efficient. Whether you're an investor seeking a strong addition to your portfolio, an owner-occupant looking to offset your mortgage with rental income, or a parent searching for housing near Portland's rapidly growing educational and innovation district, this property offers exceptional versatility. Located just minutes from Downto

Enjoy the best of Portland's East End living in this charming 2-bedroom, 1-bath single-family detached condominium, ideally situated near the Eastern Promenade. Built in 2015, this thoughtfully designed home offers the privacy of a standalone residence with the convenience of low condominium fees. The main level features an inviting open-concept kitchen, living, and dining area, perfect for everyday living and entertaining. Upstairs, you'll find two comfortable bedrooms and a full bathroom, along with space for a potential additional bathroom. Step outside to enjoy your private deck, or take advantage of the garage with ample storage for bikes, outdoor gear, and more. Just moments from the Eastern Promenade's waterfront trails, parks, beaches, and Portland's vibrant restaurants and shops, this property offers an exceptional opportunity to enjoy low-maintenance living in one of the city's most desirable neighborhoods. Whether you're looking for a year-round residence or a Portland getaw

Tucked into a beautiful, elevated well-landscaped site, with natural ledge outcroppings, perennials and mature landscaping, this distinctive shingle-style contemporary offers a blend of imagination, character, and individuality. The open, light-filled floor plan features expansive windows and glass patio doors that lead to two wonderful decks, creating an inviting connection to the surrounding landscape. The kitchen and two-and-a-half baths have been updated with newer appliances, ceramic tile and new bath fixtures. Redlon Park is an enclave of compatible shingle-style contemporary homes, each individually designed, while complementing one another and developing a neighborhood with character and charm. The flexible floor plan offers the opportunity to adapt the space to your needs. An unfinished attic may provide potential for additional living area. The seven-home Redlon Park neighborhood association shares responsibility for several common expenses, including road maintenance, up-kee

ONSITE PARKING! GREAT RENTAL HISTORY! A first floor unit with water views and walkable convenience in Portland's vibrant East End. Enjoy breathtaking vistas of Casco Bay from this charming 3 bedroom residence with recent renovations in 2019. It is ideally situated just moments from downtown. Nestled in one of the city's most beloved neighborhoods, this home offers easy access to local cafes, boutiques, the Eastern Promenade, and the waterfront. Whether you're starting your day with sunrise over the bay or strolling to dinner in the Old Port, this location is quintessential Portland living

Welcome to 68 Taft Ave, a stylish 3-bedroom, 2-bath ranch tucked into a convenient Portland location just moments from Westbrook. The main level offers an easy, spacious layout with three bedrooms, an updated kitchen, generous living room, and formal dining room. The partially finished basement adds flexible bonus space, currently used as a music and media room with a bonus informal bedroom. Step outside to a beautifully refreshed backyard designed for relaxing and entertaining. New landscaping and hardscaping surround the in-ground pool, including a Pennsylvania bluestone patio and steppers and a natural stone pool deck. A two-car tandem garage adds valuable storage and parking. With easy access to I-95 and just minutes from an abundance of shops, restaurants, and everyday conveniences, 68 Taft Ave offers the space and amenities to enjoy both home and everything Greater Portland has to offer

Rarely does an opportunity like this come along in Portland! Set on an exceptional 1.17-acres, this expansive Cape offers over 3,000 square feet of living space, privacy, investment opportunity, flexibility, and direct proximity to the outdoor recreation at Payson Park and Baxter Boulevard. The finished space above the garage includes a bonus kitchenette, dining area, living room, bedroom, office, and full batha€”ideal for extended family, guests, or income generation. While the home would benefit from some updating, the combination of land, square footage, location, investment opportunity, and versatility makes this an exceptional opportunity. Whether you envision a private family compound, a home with separate rental or guest quarters, or a thoughtfully renovated residence tailored to your lifestyle, this property provides the canvas

Enjoy refined condominium living at Hobson's Landing in the heart of Portland's historic waterfront district. Featuring water views from every room and filled with natural light, the two-bedroom, two-bath home features an open and inviting layout designed for both everyday living and entertaining. The living area is anchored by a gas fireplace and opens to a private deck, while the thoughtfully designed kitchen offers high-quality finishes, generous workspace, and seamless connection to the main living spaces. The primary suite provides a quiet retreat with a walk-in closet and ensuite bath featuring double vanities and radiant heated floors. In-unit laundry, deeded garage parking, and separate storage add to the ease and functionality of the residence. Hobson's Landing residents enjoy an impressive collection of amenities, including concierge service, a fitness center, expansive outdoor terraces, and a beautifully designed club room with a full kitchen, fireplace, and deck. Additional

Step into home ownership at Stroudwater Commons, Portland's newest condo community offering attractive living at attainable prices. With sunny spaces, timeless finishes, and modern efficiency, this 1BR/1BA home is designed for comfort and convenience. Each condo features open layouts, quartz kitchens, stylish baths, in-unit laundry, efficient heat pumps for year-round comfort, and elevator access to all levels. Parking is available for purchase starting at $5,000. Residents also enjoy access to community amenities including a fitness center, co-working lounge, bike storage, EV charging provisions, and direct Portland Trails access. The convenient Congress Street location keeps you close to everything-downtown Portland, I-295, I-95, Stroudwater Park, Fore River, USM, Rock Row, and the Jetport. Income-Qualified Workforce Homes provide a unique opportunity to transition from renting to owning. To qualify, the household must not earn more than 100% of Area Median Income ($97,370). Now avai

Prime Portland location with a neighborhood feel! Tucked away on a dead-end street, this classic 3-bedroom, 1.5-bath bungalow offers the convenience of city living in a setting that feels comfortably removed from the bustle. Enjoy an approximately 3-minute walk to the bus station, a drive of less than 5 minutes to Portland International Jetport, and easy access to downtown's restaurants, shops, and entertainment. Whether commuting, traveling, or enjoying everything Portland has to offer, this location makes getting around easy. Inside, hardwood floors, original details, and generous rooms create a welcoming foundation for your updates and personal touches. The first floor features a bedroom, office, spacious living area, and a bright enclosed front porch. The fenced yard provides room for gardening, pets, entertaining, or creating your own outdoor retreat. With its classic character, flexible layout, and prime location close to shopping, amenities, and major commuter routes, this bunga

Set on a generous 0.75-acre lot, this three-unit property combines inviting interiors, a wooded backdrop, and convenient Portland living. The property features one two-bedroom unit and two one-bedroom units, offering an appealing opportunity for investors or buyers exploring owner-occupied multifamily living. Interior highlights include white kitchen cabinetry, attractive flooring, and neutral finishes. The building has undgone updates in each unit and has been meticuliously maintained throughout. Ample on-site parking, public water and sewer, and separately metered electricity add practical appeal. With convenient access to shopping, public transportation, and major commuter routes, this is a compelling opportunity to own a versatile income-producing property with room to enjoy the outdoors

This home is within Maine Housing purchase price limits. Seller welcomes Maine Housing, FHA, VA, and USDA offers. Conveniently located with easy access to downtown Portland, public transportation, shopping, I-295, and the Portland International Jetport. Inside, the home features a multi-head Daikin heat pump system for efficient heating and cooling, along with a new Bradford White 50-gallon heat pump water heater for added energy efficiency, plus added attic and basement insulation. The flexible layout includes a first-floor bedroom and full bath, and a second floor half bath that serves two bedrooms.Laundry hookups are conveniently located on both the first floor and in the basement for whichever suits you best. The fenced backyard offers a private outdoor space for relaxing, gardening, entertaining, or enjoying time with pets. Some photos are AI enhanced to show possible layout of furniture in the bedrooms and family room. Book your in person showing today

Panoramic Casco Bay views and a private rooftop deck crown this rare offering atop Munjoy Hill. Built in 2019, 5 Merrill Street is a two-unit residence with two townhouse-style homes. Each is finished to condo quality, with contemporary design and designer details throughout, a combination seldom found in Portland. Each home has 1,725 square feet with 3 bedrooms and 2.5 baths. The kitchens have custom cabinetry, white quartz countertops, Miele appliances and generous storage. Walnut floors, striking tile, 10-foot ceilings and craftsman detailing run through every level. You can see the water from two floors, but the third-floor primary suite is the showpiece: a top-of-the-hill retreat with sweeping views over the bay from both the bedroom and the rooftop deck. Live in one home and rent the other, or keep both. Either way, it's a modern way to own a piece of Munjoy Hill

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

OPEN HOUSE: Sunday, 11/8, 12:00p-1:30p. Enjoy comfortable, easy living in this conveniently located 3-bedroom, 1-bath home! An updated kitchen opens into the dining room making entertaining a snap. The brand-new front porch adds welcoming curb appeal and provides the perfect spot to relax and enjoy your morning coffee. Out back, you'll find a spacious yard with plenty of room for gardening, outdoor activities, entertaining, or simply enjoying some fresh air. Conveniently located close to shopping, restaurants, everyday amenities, and easy access to I-95 at Exit 48, making commuting and getting around a breeze. Whether you're looking for your first home, downsizing, or simply seeking a convenient location, this property is worth a look!

Enjoy Old Port living in this spacious, updated one-bedroom condo in the heart of Portland, just steps from shops, restaurants, and local favorites, with the waterfront a short walk away. A versatile bonus room offers added options for a home office, guest space, or extra storage. Recent updates include a new forced hot water boiler and hot water heater. Elevator access, shared laundry, a dedicated storage unit, and affordable HOA dues add to the appeal, making this an excellent opportunity to enjoy the convenience and energy of downtown living. Seller is willing to pay for the first two years of parking

Highly sought after Deering Center address, perfectly located for those looking for a quiet home near Baxter Woods, walking distance to Deering Center, Woodfords Corner, Back Cove Trail, and within a few minutes of Downtown Portland. This Portland 2-family is a classic but with a little more of everything than most: generously sized bedrooms, updated kitchen and baths, front and back porches for each unit, a masonry construction garage, large usable basement with walk-out access. The real surprise comes when you enter the third floor - the vaulted ceiling in a grand bonus room plus two more bedrooms and a half bath. 35 Clinton is a special property in the world of Portland 2-units and should not be missed!

OPEN HOUSE THIS SUNDAY 7/19-Experience the best of Portland's Old Port from this stylish 2-bedroom condo with a flexible loft space, perfect for guests, work, or additional sleeping. Set within a beautifully converted historic building, the unit blends charm and modern comfort with soaring ceilings, oversized windows and an open, airy feel. A newly added heat pump ensures year-round efficiency and comfort. Step outside to cobblestone streets lined with award -winning restaurants, boutique shops, and the working waterfront just moments away. Weather you're seeking a vibrant in-town residence or a proven income property, this unit delivers, boasting a strong, established short-term rental history in a desirable association. Live, invest, or escape, right in the heart of Portland's most iconic neighborhood

Exceptional investment opportunity in Portland's highly desirable Deering Center/Rosemont neighborhood. This well-maintained multi-family property features three established units plus fully finished space with strong potential for a fourth unit (buyer to verify approvals and permitted use with city). Owner occupied since 2007, and the units are currently except from the rent increase limits imposed by the City of Portland for 3-4 unit buildings. the property offers a rare combination of off-street parking, a garage and a spacious backyard, providing added convenience and outdoor enjoyment for tenants and owners alike. Ideally situated within walking distance to the University of New England (UNE), the University of Southern Maine (USM), Rosemont Market, neighborhood shops, restaurants and everyday amenities. Outdoor enthusiasts will appreciate easy access to Evergreen Woods and its extensive network of approximately four miles on scenic walking and hiking trails. Whether you are an ow

A rare opportunity in Portland! Offered for sale for the first time, 94 Pleasant Avenue is a well-maintained four-unit property that blends historic character, spacious living, and strong income potential. The standout first-floor unit offers an impressive three bedrooms and two bathrooms, making it an ideal option for an owner-occupant looking to offset their housing expenses with rental income. Filled with natural light and character, the unit features beautiful hardwood floors, generous living space, separate dining area, a spacious kitchen, and charming architectural details throughout. The property also includes two one-bedroom units and one two-bedroom unit, providing a versatile unit mix that appeals to a broad rental market. Tenants pay their own heat and hot water, helping keep operating expenses manageable for the owner. From the inviting front porch and distinctive period architecture to the rear porches and spacious units, this property offers the character buyers love in P

Exceptional value on Munjoy Hill with this bright, well maintained two bedroom, two bath condo offering sweeping views of Casco Bay and effortless Portland living. Conveniently located on the first floor offering an open floor plan with hardwood and tile flooring, generous in unit storage, and a private primary suite. Located in the secure, elevator and ramp accessible Portland House, residents benefit from heated garage parking, concierge services, onsite gym, community room with lending library, and a beautifully kept outdoor patio with seating overlooking the bay. Most utilities included in HOA fee, including heat, hot water, water/sewer, cable and internet, making ownership simple and predictable. Just steps from the Eastern Promenade, you'll have immediate access to over 70 acres of green space, the Eastern Prom Trail, Fort Allen Park, tennis and pickleball courts, East End Beach, food trucks, and Portland's iconic waterfront. The building's lobby and community spaces have been re

Meticulously maintained and owned by the same family since it was built nearly a century ago, this Gambrel style house is ready to create new memories for the next family. There a few homes available under $600,000 in Portland. This is one of them providing great value and it won't last long on the market

Location is everything, and 1 Clairmont Court delivers. Tucked just off the beaten path near Woodford's Corner, this 2-bedroom townhouse puts you minutes from local bakeries, craft breweries, and the scenic Back Cove trail network. Inside, enjoy the separation of a true multi-level townhousea€”no upstairs or downstairs neighborsa€”complete with a half-bath on the main level for guests, bright living spaces, and a full basement ready for storage or hobbies. Easy access to downtown and I-295 rounds out this incredible Portland package. Seller Concessions Available. For a video walk-thru go to YouTube and enter the property address. If you have been thinking about selling your home, please call me for your FREE market analysis or visit for an INSTANT value

MULTI-FAMILY a€¢Three unit multi-family with strong rental history a€¢Value add opportunity with vacant non-conforming fourth unit a€¢Three car garage on a triple lot a€¢Excellent location with limited river views

Located on the prominent corner of Munjoy and Wilson Streets, just a few blocks from the Eastern Promenade and directly abutting neighborhood green space, this impressive five-unit (originally built as four 1,500 SF apartments) property offers a rare combination of scale, location, and future potential. Approximately 6,100 square feet of living space, the building is currently configured with three spacious three-bedroom, one-bath apartments, each featuring generous living rooms, separate dining rooms, and full kitchens, while the remaining floor has been divided into a one-bedroom unit and a two-bedroom unit. The building's exceptional size and coveted Munjoy Hill location create a wide range of opportunities for the next owner. A) The Owner Occupant who wants more space than a traditional, small, Portland apartment. Restore the four unit layout which allows a buyer to move into one and rent the others - free of Portland's rent control - and helps cover your rent. B) An Investor/Devel

Experience waterfront living at its finest in Hobson's Landing, Portland's premier luxury condominium community. This beautifully appointed one-bedroom residence offers sophisticated design, high-end finishes, and effortless single-level living in the heart of the city's vibrant waterfront district. The thoughtfully designed floor plan features an open-concept living space filled with natural light, a chef-inspired kitchen with premium appliances, custom cabinetry, and quartz countertops, and a spacious primary suite with ample storage and a spa-like bath. Floor-to-ceiling windows showcase captivating city and waterfront views while creating a seamless connection between indoor comfort and the beauty of Portland Harbor. Residents of Hobson's Landing enjoy an unparalleled amenity package, including concierge service, fitness center, club room, reservable guest suite, dog wash station, and beautifully landscaped outdoor spaces. Just outside your door, explore Portland's award-winning res