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37 Callaway Dr Unit 37, Westbrook
$385,000
2 Beds ⋅ 1 Baths
Why rent when you can own? Welcome to Callaway Commons - this unique standalone condo offers the best of both worlds, combining privacy with convenience. Tucked at the end of the road, the home enjoys a peaceful setting with a private backyard oasis, while remaining just minutes from the amenities of Westbrook, Portland and Windham. Inside, you'll find 1,552 square feet of living space across two levels, featuring a distinctive and flexible floor plan. The bright, open kitchen has been tastefully updated with new cabinetry, granite countertops and stainless steel appliances. It flows seamlessly into an eat in dining area with pantry and an inviting living room, perfect for everyday living and entertaining. Step outside to enjoy the elevated deck overlooking the spacious backyard. Additional highlights include an oversized two car garage and low maintenance living, with lawn care and snow removal included in the condo fee. A rare opportunity for comfort, convenience, and value - don't miss it.

37 Callaway Dr Unit 37, Westbrook

Listing courtesy of Portside Real Estate Group.

Selling Office: Allied Real Estate.

236 Longfellow St, Westbrook
$382,000
2 Beds ⋅ 1 Baths
236 Longfellow Street, Westbrook -- A Cozy One-Floor Home That Loves You Back Some houses just take care of you -- this is one of them. Single-level living at its finest, this 2-bedroom, 1-bath Westbrook home is anchored by a spacious walk-in closet and topped with a brand-new roof, so the big stuff is already handled. Efficient heat pumps keep energy costs low year-round, while the dedicated laundry room adds everyday convenience. A one-car garage and shed round out the practical, easy layout -- the kind of home that just works. And the location can't be beat. You're walkable to Main Street Westbrook, where summer evenings mean concerts on the Common and down at Vallée Square, a pint at Mast Landing Brewery, and a stroll along the Presumpscot River Riverwalk. Come June, the whole town turns out for Westbrook Together Days and the Memorial Day Parade. Add quick access to downtown Portland, I-95, the Portland Jetport, and Maine Medical Center, and you're perfectly positioned for both everyday life and easy escapes.

236 Longfellow St, Westbrook

Listing courtesy of Real Broker.

Selling Office: Keller Williams Realty.

48 Longfellow St, Westbrook
$380,000
2 Beds ⋅ 1 Baths
Walk to town, enjoy a private backyard, and own a home where the big updates are already done--this cozy Westbrook property is the perfect fit for first-time buyers, downsizers, or investors alike. Welcome to this warm and efficient 2-bedroom, 1-bath home offering approximately 950 square feet of comfortable living space on a .21-acre lot with a respectfully private backyard. Inside, you'll find mostly wood floors throughout and a layout that feels both functional and inviting. Recent improvements add real value, including a newer roof and a professionally finished basement, complete with a transferable dry basement warranty--providing long-term peace of mind. Enjoy outdoor living on the back deck, perfect for grilling, along with a storage shed that could easily be transformed into a playhouse, studio, or home office. Located within walking distance to downtown Westbrook, this home offers true convenience--whether you're commuting, using public transportation, or simply enjoying the ability to leave the car behind. A smart, efficient home with flexibility for a variety of lifestyles.

48 Longfellow St, Westbrook

Listing courtesy of Taylor & Kovacs Real Estate.

Selling Office: Keller Williams Realty.

68 Seavey St, Westbrook
$375,000
3 Beds ⋅ 2 Baths
After 27 years of being loved and lived in by the same family, 68 Seavey St is ready for its next chapter. This classic New Englander, built in 1890 and thoughtfully updated over the years, offers a rare opportunity for turn-key living at an accessible price! Fresh paint and all-new floors set the tone throughout, while the first floor flows naturally from a remodeled kitchen into a dining room, a spacious living room, and a cozy den or first floor office. Upstairs, a generous primary bedroom is complemented by 2 additional well-sized bedrooms. A walk-up attic offers serious storage potential for everything life accumulates. The updates here aren't cosmetic window dressing. They're the kind that matter: remodeled kitchen (2014), new boiler (2018), concrete basement floor (2012), three-quarter bath addition (2019), two-car garage (2019), a new roof (2020), and new floors and paint within the past month. The work has been done, and done right. Out back you are welcomed by a large yard, oversized two car garage, and shed. Conveniently located near downtown Westbrook's amenities, schools, and parks, Seavey Street puts you close to everything while still feeling like a neighborhood worth coming home to. Schedule a showing today before it's too late!

68 Seavey St, Westbrook

Listing courtesy of Real Broker.

Selling Office: Keller Williams Realty.

19 Beechwood Ave, Westbrook
$365,000
4 Beds ⋅ 1 Baths
Welcome to 19 Beechwood Ave, a classic 1937 Colonial, Equity Builder, tucked into a quiet Westbrook neighborhood. This home offers timeless charm, a livable layout, and the opportunity for the next owner to update it and make it their own. Inside, you'll find 3-4 bedrooms and 1 full bath. The first floor includes kitchen, dining room, living room, and family room that offers a flexible space. The second floor offers three bedrooms and a full bath, while the third bedroom provides walk-through access to a third-floor bonus area that can serve as a fourth bedroom, office, playroom, or extra flex space. Outside, enjoy the double-lot backyard with a spacious fenced-in area perfect for summer barbecues, pets, gardening, or relaxing at the end of the day. The home's older character, solid footprint, and livable condition make it an appealing option for buyers looking for value and the chance to add updates and build equity. Ideally located in a desirable Westbrook setting, this home offers a strong price point and a wonderful opportunity to build equity in a neighborhood that continues to attract buyers. Westbrook's amenities add to the appeal, with nearby parks, shops, restaurants, Rock Row, and convenient access to Greater Portland, making everyday living easy and enjoyable.

19 Beechwood Ave, Westbrook

Listing courtesy of Maine Real Estate Experts. YvonneSellsMaine@gmail.com

Selling Office: Portland's Choice Realty, LLC.

45 Lyman St, Westbrook
$360,000
3 Beds ⋅ 1 Baths
This 3-bedroom, single-level home offers a great opportunity for buyers looking for a home with solid bones and many of the major improvements already completed. Hardwood floors run throughout the living room and bedrooms, while the updated bathroom and fresh interior paint provide a great starting point. The living room features a heat pump, and the laundry is conveniently located in the utility room. The good-sized primary bedroom offers great closet space and includes pull-down attic access, while ample closet space can be found throughout the home. Over the years, the home has benefited from several important updates, including a newer roof and added insulation, allowing the next owner to focus on making the space their own. Outside, you'll find a good-sized backyard with two storage sheds, offering plenty of room for lawn equipment, tools, or hobbies. Located on a quiet road close to shopping, restaurants, schools, and other everyday amenities, this home combines a convenient location with excellent potential. With many of the big-ticket items already taken care of, all that's left is to bring your vision and make it your own.

45 Lyman St, Westbrook

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

Selling Office: Portside Real Estate Group.

20 Juniper Ln Unit 16, Westbrook
$350,000
4 Beds ⋅ 2 Baths
This 4-bedroom, 2-bath condo has a flexible layout designed for everyday living, working, and entertaining. A bonus room and walk-in closet provide added versatility to suit a variety of needs. The open-concept main living area feels functional and welcoming, with an updated kitchen that flows into the dining and living spaces. A first-floor bedroom with an attached bathroom supports single-level living, while additional bedrooms create lots of options. A newer on-demand furnace adds comfort and energy efficiency. With a consistent rental history, it may also appeal to buyers exploring investment potential. Conveniently situated close to downtown Westbrook, Rock Row, shopping, outdoor recreation, and local amenities. This condo offers low-maintenance living with room to spread out--whether as a primary residence or an investment opportunity.

20 Juniper Ln Unit 16, Westbrook

Listing courtesy of Maine Real Estate Experts. Kim@kuusellmaine.com

Selling Office: Keller Williams Realty.

30 Lincoln St Unit 105, Westbrook
$345,000
2 Beds ⋅ 2 Baths
Discover character and charm in this beautifully converted historic mill building along the Presumpscot River. Exposed brick walls, hardwood floors, vaulted ceilings and oversized windows fill this bright and inviting condo with natural light. Enjoy the ease of single-level living with two bedrooms, two bathrooms, and a convenient in-unit laundry area. The functional galley kitchen opens to a comfortable living space, creating an ideal setting for both everyday living and entertaining. Located on the first floor, benefit from easy access and a shared patio area, perfect for relaxing outdoors or gathering with neighbors. Pets are welcome and each condo has its own dedicated storage unit. Embrace every season with direct river access for kayaking and paddle-boarding, the Riverwalk, the nearby Meadow Nature Preserve to explore and the skating rink located right next door. The Riverfront Loft condos are conveniently situated near local shops, restaurants, and commuter routes. Enjoy a unique combination of charm, comfort and an exceptional riverfront lifestyle. This condo is ready to welcome you home.

30 Lincoln St Unit 105, Westbrook

Listing courtesy of EXP Realty.

Selling Office: Keller Williams Realty.

30 Lincoln St Unit 215, Westbrook
$345,000
2 Beds ⋅ 1 Baths
Experience the perfect fusion of historic charm and modern convenience in this distinctive loft-style condominium, ideally situated in a beautifully restored former textile mill along the Presumpscot River. Located in the heart of downtown Westbrook, this exceptional residence offers walkable access to popular restaurants, shops, and the scenic River Walk and Rivermeadow Nature Preserve--delivering an unbeatable combination of vibrant city living and tranquil waterfront surroundings. Inside, dramatic vaulted ceilings, oversized factory-style windows, and recently refinished original hardwood floors showcase the building's rich industrial character. Sunlight fills the open-concept living space, creating a bright and inviting atmosphere that feels both spacious and comfortable. The versatile floor plan includes a private main-level bedroom, plus a lofted second bedroom overlooking the living area--ideal for guests, a home office, or creative space. The pet-friendly association enhances the lifestyle with a shared riverside patio, perfect for relaxing or entertaining. Additional amenities include secure entry, on-site parking, and a dedicated basement storage unit conveniently located near the water--ideal for kayaks, paddleboards, and outdoor gear. This thoughtfully restored property combines the convenience of downtown living with the serenity of a tucked-away riverfront setting--truly a rare opportunity

30 Lincoln St Unit 215, Westbrook

Listing courtesy of Redfin Corporation.

Selling Office: Dream Home Realty LLC.

25 Three Pines Dr Unit 202, Westbrook
$325,600
2 Beds ⋅ 1 Baths
Open house 8/30 has been canceled. Pristine 2 bedroom condo in Three Pines Condominium Association. Built in 2025, with sunny & bright spaces and timeless finishes located just one mile from Downtown Westbrook. Enjoy level entry to this first floor unit and step inside to the open floor plan with a highly functional mudroom/laundry room. The bright & open living space is large enough for dining and gathering, lovely bathroom boasts a quartz vanity and linen closet. The two good sized bedrooms provide space for guests, or a great office for work from home space. Solidly built and energy efficient. Enjoy conveniences like in-unit laundry, ample storage spaces, secure entry and 2 reserved tandem parking spots. All within 10 minutes of Portland, USM, Rock Row, the Jetport, and more.

25 Three Pines Dr Unit 202, Westbrook

Listing courtesy of Keller Williams Realty.

Selling Office: Verrill Real Estate, Inc.

30 Lincoln St Unit 117, Westbrook
$316,500
1 Beds ⋅ 1 Baths
Discover an iconic piece of Westbrook's history with this stunning condo, once the Haskell Silk Mill, now reimagined as urban living spaces since 2007. Enjoy high ceilings, oversized windows, and unparalleled natural light. The completely renovated bathroom and recent updates enhance the charm of your new home. At the end of the hallway you have your own dedicated storage, as well as a lightly used shared outdoor patio. Nestled along the Presumpscot River, you'll have access to a four-season rink, kayak rentals, scenic trails, and breathtaking river views. Experience the vibrant downtown area, just a short walk away, featuring coffee shops, restaurants, and exciting events like salsa dancing and live music in the warmer months. With abundant parking and a strong sense of community, this is your chance to own a unique slice of history in a beautifully revitalized space.

30 Lincoln St Unit 117, Westbrook

Listing courtesy of Legacy Properties Sotheby's International Realty.

Selling Office: RE/MAX Realty One.

25 Lawrence St Unit 52, Westbrook
$314,000
2 Beds ⋅ 1 Baths
Stylish and low-maintenance living at Abbey Common Condominiums in Westbrook! This well-maintained 2-bedroom condo offers a bright, open-concept layout with comfortable living space anchored by a cozy fireplace. Recent updates include a brand-new Rinnai heating system, a fully renovated bathroom, and fresh flooring and paint throughout, giving the home a clean, modern feel. Upstairs you'll find two spacious bedrooms and a convenient second-floor laundry. Additional highlights include two reserved parking spaces, guest parking, and a well-managed association. Ideally located just minutes to downtown Westbrook, Rock Row, and a short drive to Portland--this move-in ready condo offers comfort, convenience, and value.

25 Lawrence St Unit 52, Westbrook

Listing courtesy of NextHome Experience.

Selling Office: Coldwell Banker Realty.

36 Arlington Ave, Westbrook
$305,000
3 Beds ⋅ 1 Baths
Opportunity awaits in this Westbrook property ready for its next chapter. With vision and updates, this home offers the chance to build equity while creating a space that truly reflects your style. The home features one-floor living with three bedrooms and one bathroom, providing a practical layout for everyday living. Front and back mudrooms offer convenient entry spaces and extra storage for coats, shoes, and outdoor gear. The flat lot provides usable outdoor space with room for gardening, recreation, or future improvements. Located in a convenient Westbrook neighborhood, you'll enjoy close proximity to local shops, restaurants, parks, and everyday amenities, making it easy to stay connected to everything the area has to offer. This property presents a great opportunity for buyers looking to invest a little more TLC and unlock the home's full potential. Bring your ideas and see the possibilities this property has to offer.

36 Arlington Ave, Westbrook

Listing courtesy of Fontaine Family-The Real Estate Leader.

Selling Office: Portside Real Estate Group.

260 Central St, Westbrook
$303,000
3 Beds ⋅ 2 Baths
Opportunity is knocking in Westbrook! Tucked near the end of a quiet street with access to the scenic Portland Trails nearby, this 3-bedroom, 1.5-bath home offers a rare chance to create something truly special. This property is in need of major renovations, making it ideal for investors, contractors, or buyers looking to build equity through improvements. The existing layout includes three bedrooms and one and a half baths, with additional potential in the basement--offering the opportunity to expand living space and increase overall value. Outside, you'll find a flat backyard that provides a great foundation for outdoor enjoyment, gardening, or future enhancements. The location combines a peaceful setting with convenient access to local amenities, trails, and nearby Portland. Bring your vision and transform this property into a rewarding investment or personalized home. This property is eligible under the First Look Initiative. All Owner Occupant offers will be responded to after 7 days on the market and Investor offers will be responded to after 30 days. However, all offers can be submitted during the First Look period.

260 Central St, Westbrook

Listing courtesy of Fontaine Family-The Real Estate Leader. 207-784-3800

Selling Office: Portside Real Estate Group.

56 Webster Ave, Westbrook
$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.

Selling Office: Realty ONE Group Next Level.

25 Lawrence St Unit 47, Westbrook
$283,000
2 Beds ⋅ 1 Baths
Welcome to easy condo living in this bright and cozy 2-bedroom townhouse-style condo! Fresh paint, updated carpeting, and a clean, well-maintained interior make this home truly move-in ready. Both bedrooms offer large closets and built-in storage for added functionality and convenience. Enjoy a private feel with a ground-level patio featuring a privacy fence and wooded views. Efficiently heated with a monitor heater featuring a 12-hour battery backup for added peace of mind during power outages, along with the option of baseboard heat and a fireplace for extra comfort. Located in a well-established condo association close to everything -- grocery stores, restaurants, the turnpike, Rock Row, schools, and more. Plus, enjoy convenient walking trail access to Hannaford and nearby amenities. Come see all this lovely condo has to offer!

25 Lawrence St Unit 47, Westbrook

Listing courtesy of Keller Williams Realty.

Selling Office: EXP Realty.

22 Berkeley St, Westbrook
$280,000
2 Baths
ATTENTION INVESTORS & RENOVATORS Two-Unit Multifamily property in need of complete renovation. This is a City of Westbrook-owned tax foreclosure. Property is being sold AS IS, WHERE IS, with all contents conveying. Seller will make no repairs and will not remove any personal property. IMPORTANT NOTICE: Property will require a cash purchase or private funding only All systems are shut off Buyer is strongly encouraged to perform all due diligence Buyers must independently research Title 36 of the State of Maine regarding municipal tax foreclosures prior to submitting an offer Showings: Saturday, January 31 | 10:00 AM - 12:00 PM Sunday, February 1 | 10:00 AM - 12:00 PM Group showings by appointment only DO NOT JUST SHOW UP! DO NOT show up without an appointment DO NOT walk or go on the property. Offer Deadline: All offers due by February 9th at 5:00 PM Seller decision expected by February 13th Seller reserves the right to accept an offer at any time

22 Berkeley St, Westbrook

Listing courtesy of American Real Estate.

Selling Office: American Real Estate.

204 Wickham Way Unit Lot 204, Westbrook
$67,000
2 Beds ⋅ 2 Baths
This is your perfect opportunity to own a tastefully updated mobile home for easy efficient living. This 2 bedroom 1.5 bathroom is move in ready. This home features recent updates throughout, including a full exterior paint job, new furnace, 2 heat pumps, a fully renovated kitchen, and renovations to both bathrooms. The fixtures, flooring and paint is updated as well. The interior is bright and inviting, with modern finishes that create a cozy yet refreshed feel. Outside you will enjoy a spacious yard with flower beds for gardening or relax on the new covered deck. The Mobile Home Park offers a dog friendly area along with a park and basketball court. Conveniently located near shopping, the highway, hospitals, dining, beaches and many other amenities this is an excellent opportunity for affordable low-maintenance living in a great community.

204 Wickham Way Unit Lot 204, Westbrook

Listing courtesy of Plowman Realty Group.

Selling Office: Maine Real Estate Experts.

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