Westbrook Real Estate

Welcome to Westbrook, Connecticut, a hidden gem nestled in the heart of Middlesex County. This picturesque coastal town offers a perfect blend of serene landscapes, vibrant community life, and rich history, making it an ideal place for those seeking both tranquility and adventure.

Westbrook boasts a stunning shoreline along the Long Island Sound, where residents and visitors alike can enjoy sun-soaked beaches, scenic parks, and charming marinas. The town is renowned for its outdoor activities, from kayaking and fishing to hiking the lush trails of nearby natural reserves. For beach lovers, Westbrook’s sandy shores provide a perfect backdrop for family picnics, sunbathing, and enjoying breathtaking sunsets.

Culturally rich and community-focused, Westbrook hosts a variety of local events throughout the year, including farmers' markets, art festivals, and seasonal celebrations that bring neighbors together. The town is also home to an array of unique shops, delightful eateries, and quaint cafes, offering a taste of local flavor and charm.

Education is a priority in Westbrook, with well-regarded schools that provide a supportive environment for children to thrive. Families will appreciate the sense of security and community that Westbrook offers, making it a wonderful place to raise children.

With its perfect combination of natural beauty, community spirit, and convenient access to major highways, Westbrook is not just a place to live, but a place to call home. Whether you’re looking for a peaceful retreat or an active lifestyle, Westbrook welcomes you with open arms. Come explore all that this charming town has to offer!

Newest Listings in Westbrook

$274,900

2 Beds ⋅ 1 Baths ⋅ 24214510 MLS

Welcome to New England Village Sun - A 55+ Community! This beautifully remodeled ranch-style home welcomes you with a bright, open floor plan filled with natural light. Enjoy all the modern updates, including new flooring throughout, a stunning new kitchen featuring granite countertops, All new appliances, ample storage, and an island perfect for meal preparation, casual dining, or enjoying your morning coffee. The open living room creates a comfortable space for relaxing or entertaining, while the propane heater provides added warmth on chilly evenings. Just off the kitchen area, there are Sliders to a wonderful new sunporch with walls of windows that invite in the sunshine and fresh coastal breezes while overlooking the pretty, private backyard. This inviting space is sure to become your favorite spot to unwind! The home offers two bedrooms and a nicely updated bathroom featuring tile and glass shower doors. Additional conveniences include a stackable washer and dryer, New Siding a large storage shed, and, last but certainly not least, an attached carport-a true bonus and a standout feature of this home! Enjoy the best of coastal living in Westbrook, with the town beach on Seaside Avenue just minutes away.The nearby Water's Edge Resort offers dining throughout the week, weekend music, and a seasonal outdoor patio with exceptional views. Explore the many restaurants along the shoreline in Westbrook and neighboring Old Saybrook,or enjoy the excellent shopping opportunities at

15 Old Forge Rd, Westbrook

$1,195,000

4 Beds ⋅ 2 Baths ⋅ 24217364 MLS

Experience the charm of coastal living in this beautifully renovated, year-round home with deeded beach access! Built in 2009 and thoughtfully updated, this delightful 4-bedroom, 2-full-bath home offers an exceptional seaside retreat with breathtaking views of the expansive sandy beach directly across the street, complete with beach rights.Inside, bright and inviting living spaces complement a gorgeous new kitchen featuring quartz countertops, a beautifully renovated first-floor full bath, and convenient first-floor laundry. Additional recent improvements include a new heating system, central air conditioning, fresh interior paint, and a new outdoor shower, providing all the comforts of modern living in a relaxed coastal setting. Spend your mornings strolling along the sandy shoreline, afternoons enjoying the water, and evenings unwinding on the spacious deck overlooking the peaceful marsh. Sheltered by Duck Island and the breakwater, the surrounding waters offer endless opportunities for paddleboarding, kayaking, boating, jet skiing, and sailing. Nearby marinas, boat mooring opportunities, bike rides for ice cream, and spectacular coastal sunsets capture the simple pleasures of a quintessential New England beach community.The property also features a garage with generous storage space and additional laundry facilities, perfect for accommodating beach gear, bicycles, and boating essentials. This special property offers the perfect combination of modern amenities and charm!

70 Old Mail Trl, Westbrook

$1,375,000

4 Beds ⋅ 2 Baths ⋅ 24165902 MLS

Own a piece of the Connecticut Shoreline lifestyle with this exceptional dual-cottage property in the sought-after Chapman Beach community! Just a short stroll to the sand with deeded private beach rights, this rare offering features two completely renovated, year-round single-family homes on one lot. This distinctive coastal property offers the perfect combination of seaside living, flexibility, and established rental income potential. The charming 824 sq. ft. guest cottage is a proven 5-star Airbnb with an established rental history and Summer 2027 reservations already secured, which must be honored by the buyer. Rental income details are available upon request. Also offering a history of academic rentals, this turnkey cottage features two bedrooms, one full bath, an updated kitchen with granite countertops, and an inviting open floor plan. A private yard and outdoor shower enhance the coastal experience, while a separate septic system, and utility meters provide added independence. New roof (2025). The fully renovated 1,100 sq. ft. main home is equally appealing, featuring two bedrooms, one full bath, an open floor plan, a new kitchen with quartz countertops and stainless steel appliances, a spacious living room with propane fireplace, and a dining area. A beautiful new 20' x 16' custom patio creates the perfect setting for outdoor entertainment. 2025 vapor barrier and blown in attic insulation ensure year round comfort.

73 Chapman Beach Rd, Westbrook

$689,900

4 Beds ⋅ 2 Baths ⋅ 24197512 MLS

Welcome to 84 Plymouth Road in Westbrook! This beautifully maintained and thoughtfully updated 4-bedroom, 1.5-bath home offers an impressive list of improvements both inside and out. Pride of ownership is evident throughout, beginning with gleaming refinished hardwood floors and a beautifully remodeled kitchen featuring granite countertops, a stylish backsplash, updated cabinetry, and French doors leading to a delightful screened porch, perfect for relaxing or entertaining. The spacious living areas offer comfortable everyday living, while all four bedrooms feature ceiling fans, and the primary bedroom is enhanced with crown molding. The full bathroom has been updated with a soaking tub and shower, while the half bath features an updated vanity top and fixtures. Step outside and discover your own private backyard retreat! Enjoy summer days around the in-ground saltwater pool, complete with an updated filtration system, pool cover, and surrounding patio and walkways. The vaulted screened porch, complete with a ceiling fan, overlooks the beautifully landscaped grounds featuring stone-walled flower beds, mature plantings, privacy trees, and attractive fencing. A retractable Sunsetter awning provides additional shaded outdoor living space. The improvements continue with new garage doors and openers, an expanded paved driveway with convenient turnaround, updated gutters, additional insulation, replacement basement windows, and a new sump pump with battery backup.

84 Plymouth Rd, Westbrook

$422,377

3 Beds ⋅ 2 Baths ⋅ 24216744 MLS

Welcome to 52 Anthony Lane, a fully renovated 3-bedroom, 1.5-bath ranch on a private, wooded acre in Westbrook. Brand new upgrades across the home: a brand-new roof, new siding and windows, and new electrical with 100-amp service. Ductless mini-splits handle both heating and cooling, and electric baseboards add extra heat when you need it. Inside, the open living room and kitchen have vaulted ceilings, a skylight, recessed lighting and hardwood floors throughout. The kitchen has two-tone shaker cabinets, quartz counters, a marble backsplash, a farmhouse sink with a gold faucet, and stainless appliances, including a French-door refrigerator. The full bath is updated with modern tile and black fixtures. Outside, a gravel driveway, and plenty of room to enjoy the yard. It's move-in ready, close to the shoreline and I-95.

52 Anthony Ln, Westbrook

$2,275,000

4 Beds ⋅ 5 Baths ⋅ 24213827 MLS

WHERE THE BEAUTY OF THE SHORELINE MEETS THE LUXURY OF COASTAL LIVING. Experience the sights, sounds, and serenity of waterfront living at 263 Seaside Avenue, where timeless New England charm meets exceptional craftsmanship and modern comfort. Completely reconstructed in 2018, including structural improvements and a third-floor addition, this beautifully appointed four-bedroom, three-full bath, two half bath coastal retreat offers semi-private beach access, thoughtfully designed living spaces, and remarkable attention to detail. The inviting open-concept first floor features custom shiplap walls and ceilings, wood-grain porcelain tile flooring, and abundant natural light. A beautifully designed kitchen showcases an oversized granite island, tile backsplash, natural gas cooktop, and walk-in pantry. A dedicated laundry room, generous closet space, and enclosed porches on both the first and second floors enhance everyday living. The luxurious primary suite features a spacious walk-in shower with body sprays, while the third floor offers two additional bedrooms and a full bathroom. Thoughtfully designed dormers add approximately 400 square feet of living space beyond the town's current assessment records.

263 Seaside Ave, Westbrook

$275,000

2 Beds ⋅ 1 Baths ⋅ 24214471 MLS

Tucked along Trolley Road in downtown Westbrook, CT, this year-round cottage offers shoreline living with walk-to-town convenience and access to the town beach. Just steps from Christie's, Julie's Cup of Joe, The Turtle Cafe, shops, restaurants, and the Westbrook train station, you can enjoy coffee, dining, and outings close to home. South of Route 1 and within walking distance of Westbrook's sandy beaches, the location puts the best of this coastal town within easy reach. The home needs love and is ready for a new owner's vision, updates, and care. Set on a generous, level lot, this property offers an opportunity to refresh the existing single-family cottage or explore new construction, subject to applicable approvals. A small section of wetlands at the very back creates a natural buffer, with the majority of the land open and usable. A great-size lot in downtown Westbrook is a standout asset, offering space to envision gardens, outdoor entertaining, and a private shoreline retreat. Whether you are looking for a year-round home, coastal getaway, or your next renovation project, this property combines beach access, downtown convenience, and room to imagine what's next. Bring your ideas, see potential, and discover how much this walkable Westbrook location has to offer. A chance to create something special in a setting you'll love.

41 Trolley Rd, Westbrook

$160,000

1 Beds ⋅ 1 Baths ⋅ 24212453 MLS

Welcome to Grove Beach Community, a vibrant 55+ neighborhood set along the beautiful Connecticut shoreline. This home is one of the newest in the community and has been lovingly maintained, offering comfortable, easy living in a peaceful coastal setting. Inside, enjoy an open floor plan featuring a spacious eat-in kitchen with breakfast bar and a bright, airy living room with access to the side yard. The large bedroom easily accommodates a king-sized bed, and the hallway laundry sits conveniently across from a generous bathroom with a large walk-in shower. The owners primarily used the home during summer months, keeping it in excellent condition. Relax on the front porch and take in the ocean air or enjoy the low-maintenance yard complete with a matching storage shed. Just a short distance away is the private Grove Beach, to which the community has beach rights, and the Westbrook Public Beach is only minutes down the road. This ideal location places you close to countless shoreline amenities-restaurants, shopping, medical facilities, and year-round activities up and down the coast. Westbrook also offers a wonderful senior center and a local YMCA. With easy access to major highways, getting around is simple and convenient. A perfect blend of coastal charm, convenience, and community living.

50 Linden Ave N, Westbrook

$569,000

3 Beds ⋅ 2 Baths ⋅ 24212425 MLS

Welcome to a wonderful opportunity to own a home in the highly desirable shoreline community of Westbrook, where a private, peaceful setting meets the many benefits of coastal-town living. Set on Dennison Road, this property offers a sense of privacy and natural surroundings while remaining close to Westbrook's beaches, shops, restaurants and community amenities, including rights to the town beach just minutes away. This home has been thoughtfully updated and prepared for its next owner. Recent improvements include a brand-new roof, new electric hot water heater, updated electrical panel and additional electrical improvements brought up to code or repaired, a newly installed water treatment system, and a new mini-split system on the main level providing both heating and air conditioning. The interior has been freshly painted, including walls and ceilings, creating a clean and inviting backdrop throughout. The kitchen features a new stove and dishwasher, while the garage door openers have recently received new safety sensors. The chimney has been professionally cleaned, and the front steps have been restored, cemented and sealed. One of the home's most special features is the beautiful year-round wooden solarium, filled with natural light from its many windows and skylights and enhanced by excellent lighting. Heated for year-round enjoyment, this inviting space provides a wonderful connection to the outdoors and opens directly onto a beautiful rear deck that extends the leng

191 Dennison Rd, Westbrook

$899,900

3 Beds ⋅ 3 Baths ⋅ 24212195 MLS

Meticulously maintained and exceptionally well-built, this 2012 Colonial is set on professionally landscaped grounds with mature plantings, a manicured lawn and front-yard irrigation. Inside, 9' ceilings and hardwood floors extend throughout the main level. The eat-in kitchen features granite countertops, stainless steel appliances and sliders to the enclosed porch. The inviting living room offers a propane fireplace flanked by built-in bookcases. French doors topped with a transom lead to the formal dining room, while a separate office/den also with French doors provides additional flexibility. A half bath with polished pink granite flooring sourced from Stony Creek Quarry completes the main level. Upstairs are three bedrooms and a bonus room, including a spacious primary suite with walk-in closet and oversized walk-in shower. Hunter Douglas shades are installed throughout. Outside, enjoy a well-appointed patio with direct propane hookup for grilling, and an above-ground pool with deck. A 30x30 detached barn/garage with 12x12 overhead door, expanded attached 1-car garage and finished space above offer exceptional flexibility for work, guests or recreation.

300 Dennison Rd, Westbrook

$115,000

2 Beds ⋅ 1 Baths ⋅ 24211601 MLS

Why rent when you can own this beautifully renovated, turn-key home? Built in 2000 and recently refreshed from top to bottom, this light and bright manufactured home offers modern comforts and effortless style. Interior Highlights: Stunning New Kitchen: Featuring sleek new appliances, soft-close drawers, and durable new luxury vinyl flooring. Recent Upgrades: Enjoy a freshly painted interior throughout, a totally renovated bathroom, and cozy bedroom carpeting only two years old. Modern Convenience: Includes a one-year-old washer and dryer and a one year old heating system. Privacy & Light: Front windows feature a specialized treatment that allows natural sunlight to pour in while maintaining complete privacy from the street. There's even a Carefree shed for outside storage. Located close to town and the amenities of the charming town of Westbrook.With an acceptable offer, the seller will contribute 6 months of the monthly fees!

5 Cook Ter, Westbrook

$495,000

4 Beds ⋅ 2 Baths ⋅ 24201461 MLS

Charming Two Multi-Family Home in Westbrook, The first Floor Unit is completely renovated, the upstairs unit is in a good condition, Step into history with this charming multi-family home, built in 1860, located in the heart of Westbrook. This 2,000 sq. ft. property offers a unique blend of historic charm and modern convenience, perfect for investors or those seeking a spacious family home. Spacious rooms with plenty of natural light original hardwood floors and historic details Functional layout with ample storage space Well-maintained yard with mature landscaping Convenient location close to schools, shopping, and dining Easy access to major highways and public transportation Neighborhood: Located in a desirable area of Westbrook, this property is within walking distance to Daisy Ingraham School and Westbrook High School. Enjoy the tranquility of a suburban setting while being just minutes away from the vibrant town center. Don't miss this opportunity to own a piece of Westbrook's history.

1280 Boston Post Rd, Westbrook

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Westbrook Real Estate

Newest Listings in Westbrook

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