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$289,000
2 Beds 1 Baths
Welcome to 56 Webster Avenue, a charming 907-square-foot Cape tucked away on a quiet dead-end street right off Brighton Avenue. Situated on a private 0.2-acre lot with mature trees and no cut-through traffic, this home blends peaceful residential living with an unbeatable commuter location. The main floor offers a sunlit living room, a full bath, and an eat-in kitchen with classic hardwood floors and sliding glass doors that open to the back deck. Upstairs, two cozy bedrooms feature quintessential Cape rooflines and built-in storage. With off-street parking and effortless access straight into Portland and downtown Westbrook, this property presents an incredible opportunity for first-time buyers, downsizers, or investors ready to bring cosmetic updates and build instant equity.

56 Webster Ave, Westbrook

Listing courtesy of Realty ONE Group Next Level.

$899,000
4 Beds 3 Baths
Your Dream Home Awaits You In Westbrook!! Welcome To 176 Mason Street!! You don't want to miss out on this Beautiful 1910 Victorian!! This very well kept and cared for home offers all of the beauty, and charm of the time period, giving the craftsmanship, and amenities that you just don't see in modern homes any more, while the huge 3,922 +/- square foot layout offers plenty of room for updates, and more modern amenities. The best of both worlds!! The first floor offers, huge rooms, lots of windows for plenty of natural light, a sunroom, 2 fireplaces, a half bath, big kitchen, laundry, hardwood and tile throughout, crown moldings, and wainscoting round out this floor!! This leads us up (2 different stairwells) to the 2nd floor, and more of the same qualities! Hard wood and tile throughout, 4 bedrooms including a Primary Bedroom Suite, 2 full baths, and another large bonus room!! This takes us to the 3rd floor and more of the same, bonus square footage, family rooms, great room, and even unfinished attic space for storage and/or future updating! The enormous full basement has a Modine heater and a finished room, also has plumbing stubbed for a possible future bath. The detached 2 car garage and spacious driveway offer plenty of parking, and plenty of storage in the unfinished second floor. The lot offers a big private yard perfect for cookouts, entertaining, and relaxing! The perfect home to grow with!! The location is amazing, close to everything, the town. shopping, and the Maine Turnpike!! The corner lot gives plenty of road frontage to make this property very versatile in its possible usages. Some commercial, business and multifamily options are definitely available making this home perfect for everyone from the growing family residence to the savviest investors alike!! This Home Is A Must See!!!

176 Mason St, Westbrook

Listing courtesy of Getty Real Estate Services, LLC.

$399,999
2 Beds 2 Baths
Built in 2024, this 2-bedroom, 1.5-bath townhouse-style condo has a spacious contemporary layout and resides on an acre and half of open grounds. The first floor features an open-concept design with a kitchen featuring granite countertops and stainless steel appliances, a living and dining room area along with a half bath and walk-out access to the rear deck. Upstairs are two bedrooms with ample closet space, a full bathroom, hall closet, and second-floor laundry. The home is equipped with a high-efficiency, wall-hung boiler system for heating and hot water. The property also includes a full basement with walk-up access, providing convenient interior and exterior entry and plenty of storage space. Outside, you'll find a covered front porch overlooking the horse pastures across the street, a private rear deck with wooded views, and two designated parking spaces. Kasseys Way is located approximately 2 miles from downtown Westbrook and Rock Row, with easy access to nearby nature trails, including Mill Brook and the Sebago to the Sea Trail. Just minutes from Portland, the location also puts you close to everything around Greater Portland, including restaurants, shopping, entertainment, parks, and more. A great opportunity to own a 2024-built home in a convenient Westbrook location.

15 Kasseys Way Unit 2, Westbrook

Listing courtesy of Maineland Real Estate. 207-650-3101

$499,000
2 Beds 2 Baths
Welcome to the heart of Westbrook, where this charming two-bedroom, two-bathroom home sits on a spacious double lot with direct water frontage on Beaver Pond. Unwind by the water's edge or entertain on the expansive, private back deck. Step inside to find gleaming hardwood floors and an inviting open-concept kitchen and living area, bathed in abundant natural light throughout the day. A dedicated main-floor office makes working from home effortless. The first-floor primary bedroom is complimented by a generously sized full bath with an expanded vanity, while the private second-floor bedroom occupies the entire upper level. The fully equipped basement offers exceptional bonus space or accessory dwelling unit (ADU) potential, complete with its own dedicated entryway, secondary kitchen area, and full bathroom.

49 E Valentine St, Westbrook

Listing courtesy of The Maine Real Estate Experience.

$594,900
3 Beds 2 Baths
Construction is underway with an anticipated early fall completion. This thoughtfully designed ranch style home by MGM Builders offers 1,825 square feet of finished living space with quality finishes and energy efficient construction throughout. The design features an open concept with vaulted ceilings. The spacious kitchen features quartz countertops, shaker-style cabinetry, stainless steel appliances, and a walk-in pantry. The living room is highlighted by a built-in electric fireplace, creating a warm and inviting gathering space. The primary suite is conveniently located on the main level and includes a walk-in closet and bath with a custom tile shower and double vanity. The finished daylight walk-out lower level provides two additional spacious bedrooms, a full bathroom. Energy-Efficient Features Include: Comprehensive air-sealing package Energy Recovery Ventilation (ERV) system GE Smart Hybrid Heat Pump water heater High-performance construction for year-round comfort and efficiency Conveniently located with quick access to I-95 and I-295, offering an easy commute while enjoying the benefits of a new, low-maintenance home. Expected completion: Early Fall 2026

20 Haddie Ln Unit 5, Westbrook

Listing courtesy of Locations Real Estate Group LLC.

$549,000
3 Beds 3 Baths
Incredible, new construction home ready for immediate occupancy. This custom built 3-bedroom, 2.5 bath craftsman style colonial includes a 1-car attached garage. Large first floor open layout. Primary bedroom suite with master bath with double vanity and huge walk-in closet. An additional 2-bedrooms, full bath and 2nd floor laundry complete the upstairs. Leathered Granite countertops in kitchen and bathrooms. High-efficiency Samsung heat pumps provide heat and air conditioning throughout. Finished 1-car garage also features an additional interior basement access. Large, unfinished basement provides for storage or future finished space expansion potential. Beautiful corner lot, off-street parking with large driveway, and awesome private deck and side yard.

18 Green St, Westbrook

Listing courtesy of J T Leahy Real Estate.

$989,000
5 Baths
Welcome to this bright and meticulously maintained Colonial 2-Unit, nestled amongst beautifully landscaped grounds and 6.48 acres of woodland. This wonderful property offers a private, rural setting but yet conveniently located to Downtown Portland, Windham and Westbrook all just a few minutes away. The Turnpike Spurs in Falmouth or Westbrook are each only about 10 minutes away. Both units offer plenty of natural sunlight, hardwood floors, granite counters, quality fixtures and appliances. The kitchen and living room layouts are open to create a casual and friendly space for living and entertaining. The primary bedrooms are spacious with space for office or workstations, a real nice feature. There are plenty of closets and storage space in both units. Step outside to garden, hike in the woods or simply relax on your private shaded deck after a long day. I absolutely love this property and I'm sure you will too!!

35 Donalene Way, Westbrook

Listing courtesy of Century 21 North East.

$449,000
2 Beds 2 Baths
**OPEN HOUSE** SATURDAY SEPT 19 FROM 10:00-12:00 Comfort, flexibility, and value come together in this inviting 2 bedroom, 2 bathroom home with 1,560 square feet of thoughtfully designed living space and a connected one car garage. From the moment you step inside, the beautiful cathedral ceilings create an open, spacious, and welcoming first impression. The main level offers a comfortable living environment with an easy flow that makes the home feel larger than its footprint. Head downstairs and discover a recently finished lower level that adds exceptional versatility to the home. Complete with a private bedroom and full bathroom, this space provides the perfect retreat for guests, extended living arrangements, a home office, or anyone looking for additional privacy and separation. With a bedroom and full bathroom on each level, the floor plan adapts beautifully to a variety of lifestyles. Outside, enjoy your own private space to unwind or entertain. The deck and fire pit area offer a cozy setting for enjoying quiet summer evenings, relaxing after a long day, or gathering with friends around the fire. Set in a quiet and welcoming neighborhood, 40 Summit Circle offers the best of both worlds. Peaceful residential living with convenient access to shopping, dining, recreation, major roadways, and everything Westbrook and the greater Portland area have to offer. A versatile layout, finished lower level, outdoor entertaining space, garage, and convenient location make this an excellent opportunity to enjoy all that Westbrook has to offer without the premium price tag. Come see why 40 Summit Circle could be the perfect place to call home

40 Summit Cir, Westbrook

Listing courtesy of Landing Real Estate.

$442,000
2 Beds 1 Baths
Enjoy easy one-level living on a grassy, level lot, with additional space to spread out in the basement family room. The updated kitchen features a window overlooking the backyard, while a bay window fills the living room with natural light. Outside, the fenced yard and tree buffer offer privacy and plenty of room for pets, playing ball, quiet evenings by the fire pit, or morning coffee on the deck. Newer roof shingles and a generator hookup add peace of mind. The oversized garage provides abundant storage above, around the workbenches, and beneath the rear overhang—ideal for recreational gear and equipment. Conveniently located near Portland trails, a Metro stop, gym, movie theater, Maine Turnpike and downtown Westbrook. Showings begin immediately and the Open House is Sat., 9/12, 1-3 PM.

27 Finch St, Westbrook

Listing courtesy of Keller Williams Realty.

$485,000
3 Beds 2 Baths
Welcome home to this beautifully maintained 3BR/2BA home tucked into one of Westbrook's well-established neighborhoods, where classic character meets smart, worry-free ownership. Some of the biggest-ticket items are already checked off the list—the roof, boiler, and kitchen appliances have all been replaced within the past six years, and a remarkably clean pre-inspection report offers even more confidence. Inside, sun-filled spaces, solid construction, and a comfortable layout create an inviting canvas ready for your own style and cosmetic touches. Outside, the generous, level backyard offers plenty of room for gardening, entertaining, play, or simply relaxing. The partially finished basement adds valuable bonus space for a home office, gym, workshop, playroom, or whatever life calls for. And the location? Hard to beat—walk to downtown Westbrook, the riverfront, restaurants, shops, parks, and neighborhood schools, while still enjoying the peace and comfort of an established residential setting. At $485,000, this is an opportunity to own a well-cared-for home with the major investments already made and plenty of room to make it truly yours! This home has been pre-inspected for the buyer's convenience. Seller Concessions Available.

109 Monroe Ave, Westbrook

Listing courtesy of Keller Williams Realty.

$650,000
3 Beds 3 Baths
Welcome to Collins Place! This spacious three-bedroom, two-and-a-half-bath condominium features an open-concept living room, dining area, and kitchen, ideal for both everyday living and entertaining. The beautifully appointed kitchen offers quartz countertops, abundant cabinetry, and upgraded appliances. The thoughtfully designed floor plan includes the option of first- or second-floor laundry, wide hallways, generously sized rooms, and engineered hardwood flooring. Additional highlights include a huge bonus room over the garage featuring an electric fireplace, an oversized one-car garage, a large front porch, and a private backyard. Conveniently located near I-295 and I-95, with easy access to downtown Portland, shopping, schools, and other local amenities.

3 Collins Pl Unit 3, Westbrook

Listing courtesy of F.O. Bailey Real Estate.

$575,000
3 Beds 2 Baths
Set on 1.21 private acres, this inviting three-bedroom home offers the space, flexibility, and convenient location buyers are looking for. Tucked away in a peaceful setting yet just minutes from Westbrook and Portland, with easy access to the turnpike, it provides a welcome retreat without sacrificing proximity to shopping, dining, recreation, and everyday amenities. Inside, the home feels bright, fresh, and move-in ready with luxury vinyl flooring, newer appliances, and recently painted interiors. The spacious living room flows into a light-filled dining area where large windows bring in views of the surrounding greenery. Step directly from the dining room onto the deck—an ideal spot for morning coffee, outdoor dining, or simply relaxing and enjoying the privacy of the property. The kitchen offers plenty of workspace and cabinetry along with a casual eat-in area, creating a comfortable gathering place for everyday meals. Three bedrooms on the second floor provide room for family, guests, or a home office, while the additional bonus room adds valuable flexibility for a media room, exercise space, playroom, hobby room, or additional bedroom. Outside, the 1.21-acre lot offers a sense of space and privacy that can be hard to find this close to Greater Portland. Surrounded by mature trees and greenery, there is plenty of opportunity to enjoy the outdoors while still being conveniently connected to everything the area has to offer. With its fresh interior, flexible living spaces, private setting, and easy access to Westbrook, Portland, and major commuting routes, this home brings together comfort, convenience, and room to make it your own.

668 E Bridge St, Westbrook

Listing courtesy of Keller Williams Realty.

$440,000
4 Beds 2 Baths
Welcome to 2 Carlson Street, a thoughtfully updated ranch offering comfortable single-level living in Westbrook. Just minutes from Portland and downtown Westbrook, this inviting home was renovated in 2012 and has continued to see improvements over the years. Inside, you'll find a modern kitchen with granite countertops, convenient first-floor laundry, and an easy, functional layout. Major recent updates include two new heat pumps and a new roof installed in 2024. Outside, enjoy a spacious fenced-in yard offering privacy and plenty of room to relax, entertain, garden, or play, along with a newly built storage shed. Move-in ready with major updates already completed, 2 Carlson Street combines single-level convenience, generous outdoor space, a large in-town lot, and room for future possibilities—all in a location convenient to everything Westbrook has to offer.

2 Carlson St, Westbrook

Listing courtesy of Real Broker.

$899,000
3 Baths
108 Longfellow Street, Westbrook — a fully renovated three-unit multifamily, offered on its own. Each of the three units is a spacious, sun-filled 2 bedroom, 1 bath with its own heat and separately metered electricity, keeping operating costs clean. Renovations were done thoughtfully throughout, so this is a turnkey building, not a project. Unit 3 comes with an unfinished third floor — room to grow into additional living space or potentially a fourth unit, subject to Town of Westbrook approval. Located in a walkable Westbrook neighborhood minutes to downtown, Portland, and major commuter routes, with schools, amenities, and transportation close by. Want more? The adjoining land is available separately — a single-family building lot and a 1.1-acre parcel surveyed for up to nine units — or purchase everything together under MLS #1678416. Buy the building for income today, or take the whole site and control the next phase.

108 Longfellow St, Westbrook

Listing courtesy of Dream Home Realty LLC.

$672,000
3 Beds 3 Baths
Beautifully maintained and filled with timeless character, this Federal-style home offers more than 2,000 square feet of living space in an established neighborhood just minutes from Portland and the Jetport. From the moment you step inside, the home's architectural details stand out, including beautiful hardwood floors, classic 15-pane glass doors, and thoughtfully preserved features throughout. The spacious floor plan offers plenty of room to spread out, highlighted by a massive family room and a comfortable primary suite. The finished basement provides even more versatile living space and features a fireplace, creating the perfect spot for a media room, home office, game room, or cozy retreat. Outside, enjoy a private, fenced-in backyard with a deck and screened porch--ideal for summer evenings, entertaining, pets, or simply relaxing at home. A spacious attached two-car garage adds convenience and plenty of room for vehicles and storage. Meticulously cared for inside and out, this home offers a wonderful combination of classic New England character, generous living space, privacy, and an incredibly convenient location close to Portland, the airport, shopping, dining, and major commuter routes.

15 Walton St, Westbrook

Listing courtesy of Landing Real Estate.

$640,000
3 Baths
Welcome to 57 Wilson Drive, a well-maintained multi-family property offering the opportunity for dual rental income in a convenient Westbrook location. The main level features an open and functional floor plan with a kitchen, living room, and dining area, along with a primary suite, two additional bedrooms, full bathroom, and first-floor laundry. A back deck overlooks the spacious backyard and provides additional outdoor space. The daylight basement offers a separate and spacious living area featuring a large kitchen, full bathroom, expansive living and dining areas, and three bedrooms. With two distinct living spaces, this property offers an excellent opportunity for rental income and investment potential. Set on approximately 1.37 acres at the end of a dead-end street, the property provides ample outdoor space while remaining conveniently located near Westbrook's shopping, dining, amenities, and major roadways. With two well-appointed living spaces, generous bedrooms, outdoor space, and a desirable location, 57 Wilson Drive presents an excellent opportunity to add a versatile multi-family property to your investment portfolio.

57 Wilson Dr, Westbrook

Listing courtesy of Signature Homes Real Estate Group, LLC.

$640,000
6 Beds 3 Baths
Welcome to 57 Wilson Drive, a well-maintained property offering flexible living space and the potential for rental income. The main level features an open and inviting floor plan with a kitchen, living room, and dining area that flow seamlessly together. The primary suite is complemented by two additional bedrooms, a full bathroom, and the convenience of first-floor laundry. A back deck overlooks the spacious backyard, providing an enjoyable outdoor setting. The daylight basement offers an additional living space with a large kitchen, full bathroom, expansive living and dining areas, and three bedrooms. This versatile lower level provides numerous possibilities for additional living space, guest accommodations, home office use, or rental potential. Situated on approximately 1.37 acres at the end of a dead-end street, the property offers a private setting while remaining conveniently located in Westbrook with easy access to local amenities, shopping, dining, and major roadways. Whether you're looking for flexible space to accommodate your needs or an opportunity to generate additional rental income, 57 Wilson Drive is a property worth exploring.

57 Wilson Dr, Westbrook

Listing courtesy of Signature Homes Real Estate Group, LLC.

$399,000
2 Beds 2 Baths
Open House: Saturday, August 29, 9-11 AM Come see this desirable, light-drenched, close to town 2-3 bedroom ranch, offering modern, low-maintenance single-floor living with a fenced-in backyard and a giant two-car garage! The updated kitchen features stainless steel appliances and granite countertops, and the home is filled with natural light. A newly tiled and painted sunroom leads out to your private, fenced backyard, where mature perennial gardens bloom through the spring and summer months. The basement adds a full bathroom, laundry room, built-in bar, family room, and storage space ready for your vision. (The neighbors, whose house is the same layout, converted their basement to an apartment last year -- could that be a plan for you?) The oversized garage includes an extra bay for tools or the lawn mower, or perhaps a craft shed! Only 10 minutes to Portland, 5 minutes to the Turnpike, and 15 minutest to the JetPort, This home has neighborhood feel with big city features! New to Westbrook? Here's what's nearby: Rock Row -- a 100-acre hub anchored by Market Basket and REI, with Starbucks, Crumbl Cookies, and more retail & dining on the way. The Westbrook Riverwalk -- a scenic mile along the Presumpscot River, connecting Riverbank Park and Westbrook Common. Local Brewery & Restaurants -- Mast Landing Brewing Company plus dozens of locally-owned restaurants. Westbrook World Markets -- Istanbul Restaurant & Bakery and Medeo European Food & Deli bring genuine international flavor downtown. Move-in ready, room to expand, and close to it all -- come see 255 Park Road, Westbrook, for yourself!

255 Park Rd, Westbrook

Listing courtesy of Dream Home Realty LLC.

$679,000
3 Beds 3 Baths
Just completed and ready for its first owners! This beautiful brand-new home offers buyers the opportunity to enjoy all the benefits of new construction without the typical wait. Thoughtfully designed with an open, functional layout and quality finishes throughout, this spacious two-story home is tucked into a private setting in Phase 5 of sought-after Brooks Edge Farm. A welcoming covered front porch leads into a bright and inviting interior. The hardwood-floored mudroom provides convenient access to the attached two-car garage and offers plenty of space for everyday living. The heart of the home is the open-concept kitchen, dining, and living area, creating an ideal space for entertaining and gathering, with direct access to a large rear deck overlooking the peaceful, wooded surroundings. The first-floor primary suite provides a comfortable private retreat with a generous walk-in closet, granite-topped vanity, and spacious tiled shower. Upstairs, you'll find two additional bedrooms, a full bath, dedicated laundry room, linen closet, and versatile den--perfect for a home office, reading room, or additional living space. A full-size unfinished basement offers abundant storage and utility space with plenty of potential for future expansion. With its brand-new construction, private wooded setting, thoughtful floor plan, and immediate availability, this is a wonderful opportunity to make Brooks Edge Farm home.

171 Brook St Unit 41, Westbrook

Listing courtesy of Signature Homes Real Estate Group, LLC.

$599,000
3 Beds 2 Baths
Nestled on just under two private acres, this special 3- to 4-bedroom, 2-bath home offers the privacy of a country setting with the convenience of nearby amenities. Inside, the flexible layout offers comfortable living spaces and plenty of versatility, including the potential for a first-floor bedroom and a convenient mudroom. Beautiful exposed Douglas Fir framing adds warmth, character, and architectural interest throughout the home. Surrounded by mature trees, the property has a peaceful, treehouse-like feel, creating a sense of being immersed in nature while still being close to everything Westbrook has to offer. Adding to the property's appeal is a two-car garage, along with a spacious outbuilding featuring dedicated woodworking space and additional garage bays, providing exceptional flexibility for hobbies, projects, storage, or recreational vehicles. An expansive yard offers plenty of room to roam, while the in-ground pool provides a wonderful setting for relaxing and entertaining family and friends throughout the summer. Whether you're looking for space to pursue hobbies, store equipment, enjoy outdoor activities, or simply unwind in a private setting, this property offers plenty of possibilities.

59 Hardy Rd, Westbrook

Listing courtesy of Town & Shore Real Estate.

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