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263 Seaside Ave, 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

18 Cedar Ln, Westbrook
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 24203578 MLS
Welcome to 18 Cedar Lane in Westbrook-a contemporary 3-bedroom, 3-full-bath home offering the perfect blend of modern living and beach-community lifestyle. Step inside to an open-concept living space highlighted by soaring cathedral ceilings, and the stone wood burning fireplace in the living room. Open to a beautifully remodeled kitchen completed in 2023 with an adjacent dining area. Designed for cooking, gathering, and entertaining, the kitchen features stainless steel appliances, granite countertops, and an oversized center island. An enclosed sunroom provides flexible year-round living space and opens through sliders to the deck-perfect for extending everyday living outdoors. The main-level primary suite offers the convenience of an ensuite full bath, while two additional bedrooms are located upstairs. The asphalt roof was replaced in 2025. Enjoy all the benefits of this coastal community with an annual association fee that includes beach access and maintenance, use of tennis, pickle ball and basketball courts, community pavilion access, grounds maintenance for community areas, and weekly trash pickup. Contemporary style, thoughtful updates, and a beach-community setting come together at 18 Cedar Lane. Welcome to the shoreline lifestyle!

18 Cedar Ln, Westbrook

300 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

26 Chittenden Hill Rd, Westbrook
$825,000
4 Beds ⋅ 2 Baths ⋅ 24203412 MLS
A rare opportunity to own a distinctive country estate with two full residences on 5.68 private acres. A charming circa-1710 center-chimney colonial. Offering four bedrooms, 2 full baths, approximately 2900 square feet, and three fireplaces. Rich with traditional character, the home features an updated kitchen, newer steam boiler, new cedar roof, updated full baths, and mini-split system with 10 head units. An expansive patio overlooks beautiful gardens and meadows, creating an exceptional setting for entertaining. The separate two-bedroom residence offers comfortable living space plus adjoining meeting rooms and a library with a deck overlooking the meadows-ideal for extended family, guests, a studio, home office or other flexible uses. The grounds include a barn, gardeners shed, henhouse, 2 rabbit hutches and garage. Adjoining open space and conservation land, this remarkable property offers an uncommon combination of privacy, versatility, history and the character of a true country estate.

26 Chittenden Hill Rd, Westbrook

81 Little Stannard Beach Rd, Westbrook
$750,000
3 Beds ⋅ 3 Baths ⋅ 24202484 MLS
Welcome to 81 Little Stannard Beach Road, a truly hidden gem nestled within the desirable Little Stannard Beach Association in Westbrook. Offering the best of shoreline living, this exceptional contemporary home is just a short walk from your own private white-sand beach and showcases breathtaking, peaceful views of the surrounding marsh. Situated on an extremely rare double lot, this property offers the privacy, yard space, and parking that are so difficult to find along the shoreline. Meticulously maintained, the upper level welcomes you with an open and airy floor plan featuring beautiful hardwood floors in the kitchen area and abundant natural light. The updated kitchen is fully equipped with stainless steel appliances and opens seamlessly into the spacious living room, where panoramic windows frame the stunning marsh views. A cozy wood-burning fireplace creates the perfect setting for relaxing, while sliding doors lead to the spacious upper deck, offering a peaceful and private space to take in the breathtaking surroundings. Tall ceilings and skylights further enhance the bright, open feel, and an additional nook provides the perfect space for a home office or desk. A convenient half bath completes this level. The fully finished lower level offers three bedrooms and two full bathrooms. Two cozy bedrooms provide comfortable accommodations, while one full bathroom features tile flooring and a stand-up shower.

81 Little Stannard Beach Rd, Westbrook

84 Plymouth 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

340 Toby Hill Rd, Westbrook
$650,000
3 Beds ⋅ 3 Baths ⋅ 24200383 MLS
Seller willing to help buyer REDUCE their interest rate!!! Welcome home to this classic colonial beautifully situated in a serene Westbrook setting! Conveniently located just north of Route 95, this property offers the ultimate blend of peaceful privacy and prime accessibility, putting you just an 8-minute drive from the beautiful Connecticut shoreline and local beaches, as well as being close to shopping centers and schools. Set back from the road and surrounded by mature trees for wonderful natural privacy, the exterior also boasts a brand-new roof, two convenient outdoor sheds for extra storage, and a fantastic fenced-in dog area. Step inside to discover a spacious living room featuring hardwood floors, and a gas fireplace to keep you cozy during cooler New England evenings. The living space flows into an open-concept kitchen and casual sitting area, highlighted by stainless steel appliances, wood cabinetry, and a convenient breakfast bar. A dedicated formal dining room just off the kitchen offers a warm atmosphere for hosting dinner parties. Downstairs, you'll find a partially finished basement serving as a flexible space, perfect for a home gym, media center, or recreation room. Completing this wonderful property is a large, attached two-car garage providing ample parking. This home perfectly balances everyday convenience with coastal New England charm.

340 Toby Hill Rd, Westbrook

35 Chapman Mill Pond Rd, Westbrook
$650,000
3 Beds ⋅ 3 Baths ⋅ 24199335 MLS
Welcome to 35 Chapman Mill Pond Road.....A KAYAKERS PARADISE! This lovingly maintained, well built, light filled home, nestled on a private, yet not secluded setting along the beautiful Menunketesuck River is a property not to be missed. You can Kayak to the Long Island Sound, watch the birds, fish, go crabbing or just simply enjoy the beauty all around you from your own private, park like backyard. Enjoy your beautiful water views right from the house. This property includes a concrete dock, a full house generator, new metal roof with snow/ice guards, new gutters, new 12x16 multi purpose structure with a/c, heat , workbench, and so much more. A new fence, extensive tree removal, 3 brand new mini splits throughout the house and pristine hardwood flooring. Recently inspected including house, septic, well water, pressure and radon. Close by to Westbrook's beautiful beaches and restaurants. On a train line between NYC and Boston, Come take a look to see its idyllic riverfront setting and generous acreage.

35 Chapman Mill Pond Rd, Westbrook

1221 Essex Rd, Westbrook
$649,900
5 Beds ⋅ 4 Baths ⋅ 24206675 MLS
Welcome to your own private retreat offering the perfect blend of secluded tranquility yet minutes from Westbrook center, local town beach, restaurants, and major highway access. Featuring 5 spacious bedrooms and 3.5 baths, the 2,583 sq. ft. Cape provides plenty of room for family, guests, or home office needs. This home is set on a peaceful 3.5 acres with a detached, oversized two-car garage offering plenty of vehicle parking, storage, & workshop potential. Upgrades include a new roof on both the house & garage as well as a new 1500-gallon septic tank. There is new carpeting and new window treatments throughout the house, including new motorized, honeycomb shades in the living room. The interior has been recently painted. The spacious kitchen has a large, granite-topped island, a new gas range, a greenhouse window, and cozy fireplace. It kitchen opens to an expansive 35' x 15' deck...ideal for alfresco dining. There are two bedrooms, 1.5 baths, and a laundry room on the first floor allowing for first floor living if needed. An impressive 19'x 17' primary bedroom is accessed from a private staircase. This light and bright room with its beamed cathedral ceiling, skylights, and private bath would also make a wonderful artist studio, bonus area, or game room. Two additional bedrooms and a bath are located off the home's second staircase. There is a propane generator and full basement with hatch. Across from The Preserve with hiking trails. Midway location between NYC & Boston.

1221 Essex Rd, Westbrook

38 S Main St, Westbrook
$605,000
3 Beds ⋅ 2 Baths ⋅ 24206967 MLS
Step into timeless New England charm with this enchanting antique home, circa 1760, ideally set in the heart of the beloved shoreline community of Westbrook. Rich in character and history, this beautifully maintained residence blends classic period details with modern comforts for effortless coastal living. Featuring six inviting fireplaces, the home's warmth, ambiance and thoughtfully preserved architectural details celebrate this home's true heritage. An in-ground, heated pool creates a private backyard retreat while the "walk-to-everything" location makes this home a perfect escape from a hustle and bustle daily life. Just moments from the beach, charming town center, dining and community events, this home also features a two-story barn creating extra valuable storage or flexible space for hobbies, game room, beach gear or workshop space. Located in a desirable beach community, this special property also boasts a proven and successful rental history with excellent income potential or a seamless blend of personal use and investment opportunity. A rare chance to own a piece of history in a prime shoreline setting where coastal lifestyle, character and convenience come together beautifully.

38 S Main St, Westbrook

191 Dennison Rd, 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

428 Hammock Rd N, Westbrook
$519,000
4 Beds ⋅ 4 Baths ⋅ 24201730 MLS
NEW PRICE! Meticulously maintained and truly move-in ready, this spacious four-bedroom, three-and-a-half-bath Colonial offers exceptional space and versatility just minutes from the Connecticut shoreline. Freshly painted throughout, the welcoming main level features a formal living room and dining room, spacious family room, and a charming 3-season sunroom overlooking the fenced backyard-perfect for relaxing or entertaining. The partially finished walkout lower level provides valuable additional living space with endless possibilities for a home office, recreation room, guest space, or possible in-law setup. Additional features include main-level laundry, an indoor hot tub, two-car attached garage, level corner lot, beautifully maintained lawn, and vegetable garden. Conveniently located near West Beach, Coral Sands Beach, shoreline restaurants and shopping, the Westbrook train station, and I-95. With four bedrooms, 3.5 baths, generous living space, and a home that has been exceptionally cared for, this property offers tremendous value in coastal Westbrook. Now offered at $519,000-come see all this home has to offer!

428 Hammock Rd N, Westbrook

1010 Boston Post Rd, Westbrook
$499,000
3 Beds ⋅ 2 Baths ⋅ 24206182 MLS
Timeless New England charm meets comfortable modern living in this 1905 Shoreline home. Offering approximately 1,380 square feet, this distinctive 3-bedroom, 2-bath residence features warm hardwood floors, beautiful millwork, beadboard accents, & a cozy propane stove. The updated kitchen offers custom cabinetry, granite countertops, stainless-steel appliances with a sunny eat-in area filled with natural light from numerous windows. The flexible floor plan includes a first-floor bedroom & full bath, with two additional bedrooms & full bath upstairs. Outside, enjoy a serene private seating & relaxing area fenced in, mature landscaping, detached 1 car garage ^ shed. A charming opportunity to own a piece of Shoreline history with thoughtful updates & enduring character. Less than 5 minutes to the West Beach area of Westbrook, shopping, dining & the Elks Club.

1010 Boston Post Rd, Westbrook

52 Anthony Ln, 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

41 Trolley Rd, 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

50 Linden Ave N, 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

5 Cook Ter, 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

15 Broadway N, Westbrook
$99,000
2 Beds ⋅ 1 Baths ⋅ 24201167 MLS
Welcome to 15 Broadway North in Westbrook, where coastal charm meets comfortable everyday living. Ideally located just minutes from Westbrook's beautiful shoreline, beaches, marinas, restaurants, shopping, and town amenities, this home offers the perfect opportunity to enjoy everything the Connecticut shoreline has to offer. Step inside to a bright and inviting interior with a functional layout designed for both everyday living and entertaining. The property offers comfortable living spaces, plenty of natural light, and the opportunity to make it your own. Whether you're looking for a year-round residence, weekend coastal retreat, or investment opportunity, this home delivers location and lifestyle. Enjoy easy access to Westbrook Town Beach, downtown Westbrook, the train station, I-95, and neighboring shoreline towns, making commuting and weekend exploring a breeze. Don't miss your opportunity to own a piece of the Connecticut shoreline at 15 Broadway North. Schedule your private showing today!

15 Broadway N, Westbrook

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