Westbrook, CT Homes

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  $449,000

  $26K PRICE DROP Pending

  • 3 Beds
  • 1.5 Baths
  • 1,790 Sq Ft

  523 Essex Rd, Westbrook, CT 06498

  Charming, light-filled 3-bedroom split-level home ideally located with convenient access to Westbrook's beautiful beaches, restaurants, shopping, I-95, and Route 9-perfect for year-round living or a weekend retreat. This well-maintained home features hardwood floors throughout the living room, dining room, and all three bedrooms. The bright living room is anchored by a large picture window

  

  Sarah McMillan

  Our Home Realty Advisors

  523 Essex Rd, Westbrook, CT 06498
• Explore Westbrook

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  /33

  $2,400 Per Month

  • 3 Beds
  • 2 Baths
  • 1,179 Sq Ft
  • House for Rent

  12 Elm Ave, Westbrook, CT 06498

  Beautiful Beach House Just Steps from Island View Private Beach Experience the best of coastal living in this beautifully maintained beach house, available as an academic rental from September 1, 2026, through May 31, 2027. Whether you're relocating, working remotely, or simply looking to enjoy the beach community lifestyle, this home offers comfort, convenience, and charm. This clean and

  Terry McDonald McDonald Real Estate, LLC

  12 Elm Ave, Westbrook, CT 06498
• 

  $170,000

  Sold Nov 05, 2025

  56 Linden Ave N, Westbrook, CT 06498

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft
  • Built 2012

  Last Sold Summary

  • 2% Below List Price
  • $202/SF
  • 6 Days On Market

  Last Listing Agent Judith DuMouchel J.M. REALTY

  56 Linden Ave N, Westbrook, CT 06498
• 

  Est $617,404

  Not Listed For Sale

  37 Menunketesuck Rd, Westbrook, CT 06498

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1930

  37 Menunketesuck Rd, Westbrook, CT 06498

  Last Sold Summary

  • 33 Days On Market
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  /40

  $1,195,000

  • 4 Beds
  • 3 Baths
  • 2,728 Sq Ft

  448 A - B Grove Beach Rd N, Westbrook, CT 06498

  Back on the market after a long snowy winter: This exceptional property includes two residences on 3.2 acres of the beautiful tidal flowing Menunketusuck River. The impeccably maintained primary antique main house offers 3+ bedrooms and 2 full baths. There are 3 fireplaces, one in the living room, the den, and the dining room. The four-season enclosed porch is the length of the home with walls of

  

  Al Chiarito

  Chiarito Real Estate LLC

  448 A - B Grove Beach Rd N, Westbrook, CT 06498
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  /2

  Call for Price

  • 1 Bed

  34 Worthington Dr, Westbrook, CT 06498

  Worthington Manor

  

  34 Worthington Dr, Westbrook, CT 06498
• 

  $630,000

  Sold Apr 01, 2026

  10 Winterberry Cir, Westbrook, CT 06498

  • 3 Beds
  • 2 Baths
  • 2,590 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $243/SF
  • 59 Days On Market

  Current Estimated Value $619,018

  Last Listing Agent Amaurys Valdera Brokerbe Inc.

  10 Winterberry Cir, Westbrook, CT 06498
• 

  Est $716,387

  Not Listed For Sale

  1414 Essex Rd, Westbrook, CT 06498

  • 3 Beds
  • 2.5 Baths
  • 2,665 Sq Ft
  • Built 2002

  1414 Essex Rd, Westbrook, CT 06498

  Last Sold Summary

  • 40 Days On Market
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  $1,195,000

  $105K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,728 Sq Ft

  448 Grove Beach Rd N, Westbrook, CT 06498

  There is a lot to enjoy here. A drive by of this property does not show the whole picture. This is an exceptional 3+ acre waterfront property on the Menunketesuck River. This package deal includes the well maintained Cerca 1745 Antique main home that is beautifully kept and appreciated, it shows beautifully. A fully equipped guest house is also included and has many options. A huge detached

  

  Al Chiarito

  Chiarito Real Estate LLC

  448 Grove Beach Rd N, Westbrook, CT 06498
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  $30,000 Per Month

  • 2 Beds
  • 3.5 Baths
  • 3,420 Sq Ft
  • House for Rent

  505 Seaside Ave, Westbrook, CT 06498

  Indulge in an extraordinary shoreline escape in this exceptional luxury coastal retreat-far beyond the ordinary beach house rental. This rare and exclusive summer residence with 2 Bedrooms, 3 Full and 1 Half baths, 2 Flex spaces, and an office presents a unique opportunity to experience elevated seaside living in one of the shoreline's most coveted settings. Set on a spacious half-acre lot, this

  Allison Ciarcia William Raveis Real Estate

  505 Seaside Ave, Westbrook, CT 06498
• 

  $440,000

  Sold Apr 15, 2026

  207 Pettipaug Rd, Westbrook, CT 06498

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $423/SF
  • 22 Days On Market

  Current Estimated Value $437,531

  Last Listing Agent Thomas Mele Social & Co Realty

  207 Pettipaug Rd, Westbrook, CT 06498
• 

  Est $2,184,176

  Not Listed For Sale

  151 Old Mail Trail, Westbrook, CT 06498

  • 4 Beds
  • 3.5 Baths
  • 2,513 Sq Ft
  • Built 2013

  151 Old Mail Trail, Westbrook, CT 06498

  Last Sold Summary

  • 83 Days On Market
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  $419,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,281 Sq Ft

  405 Pond Meadow Rd, Westbrook, CT 06498

  Charming Cape is set on a lovely, level lot in a desirable location just minutes from picturesque Westbrook Center and the beautiful shoreline. Inside, you'll find a spacious living and dining room combination featuring a cozy fireplace with wood-burning stove-perfect for relaxing or entertaining. The main level offers the convenience of a first-floor primary bedroom, along with an additional

  

  Cathy Lynch

  Coldwell Banker Realty

  405 Pond Meadow Rd, Westbrook, CT 06498
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  /28

  $3,900 Per Month

  • 3 Beds
  • 2 Baths
  • 1,606 Sq Ft
  • House for Rent

  Unlisted Address

  Amazing BEACHFRONT home available for an Academic Rental. This fully furnished and fully remodeled property is available beginning October 1, 2026 and available through May 31, 2027. Enjoy breathtaking views of the Long Island Sound from nearly every room in the house. Spectacular sunrises await you each morning! The home features three bedrooms and two full baths. It has a beautifully appointed

  Evan Berman William Raveis Real Estate

  Unlisted Address
• 

  $3,275,000

  Sold Feb 09, 2026

  166 Fiske Ln, Westbrook, CT 06498

  • 4 Beds
  • 5 Baths
  • 4,747 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $690/SF
  • 262 Days On Market

  Current Estimated Value $3,185,466

  Last Listing Agent Margaret Muir William Pitt Sotheby's Int'l

  166 Fiske Ln, Westbrook, CT 06498
• 

  Est $545,533

  Not Listed For Sale

  164 Hammock Rd N Unit 23, Westbrook, CT 06498

  • 2 Beds
  • 2.5 Baths
  • 1,764 Sq Ft
  • Built 2001

  164 Hammock Rd N Unit 23, Westbrook, CT 06498

  Last Sold Summary

  • 15 Days On Market
• 

  

  /20

  $119,900

  $30K PRICE DROP Under Contract

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  23 Linden Ave N, Westbrook, CT 06498

  If you've been waiting for something that just feels right, this is it. Welcome to 23 N Linden Ave in one of Westbrook's sought-after 55+ shoreline communities. What makes this home stand out is the enclosed sun porch, a bonus space you don't often see and one you'll actually use every day for coffee, relaxing, or coming back from the beach! Inside offers a bright, open living area with an easy,

  Eliesha Johnson William Raveis Real Estate

  23 Linden Ave N, Westbrook, CT 06498
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  $2,300 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • House for Rent

  14 Leeway Dr, Westbrook, CT 06498

  Immaculate 4 room ranch with living/dining combo, full kitchen, hardwood floors, 2 large bedrooms, plus small room for den with extra day bed, bath and a half plus shower outside in fenced in yard, short walk to beach, View of Long Island sound from deck facing the water!!

  Salome Kirkutis SKS Realty

  14 Leeway Dr, Westbrook, CT 06498
• 

  $500,000

  Sold Feb 13, 2026

  1 Spencer Plains Rd, Westbrook, CT 06498

  • 3 Beds
  • 2 Baths
  • 1,306 Sq Ft
  • Built 2006

  Last Sold Summary

  • $383/SF
  • 29 Days On Market

  Current Estimated Value $510,946

  Last Listing Agent Ferdinand Giacinto RE/MAX on the Bay

  1 Spencer Plains Rd, Westbrook, CT 06498
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  Est $722,418

  Not Listed For Sale

  8 Osprey Cir, Westbrook, CT 06498

  • 3 Beds
  • 2 Baths
  • 1,446 Sq Ft
  • Built 2001

  8 Osprey Cir, Westbrook, CT 06498

  Last Sold Summary

  • 38 Days On Market
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  /35

  $399,900

  • 4 Beds
  • 1.5 Baths
  • 1,664 Sq Ft

  41 Roberts Rd, Westbrook, CT 06498

  Welcome to 41 Roberts Road, a wonderful opportunity to create your ideal shoreline retreat. Situated on 1.84 private acres at the end of a quiet cul-de-sac, this 4-bedroom, 1.5-bath home offers over 1,600 square feet of living space and endless potential for customization. Whether you're looking for a year-round residence, vacation getaway, or investment opportunity, this property provides the

  Cheryl Cook Re/Max Valley Shore

  41 Roberts Rd, Westbrook, CT 06498
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  /5

  $1,395 Per Month

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft
  • Apartment for Rent

  189 Seaside Ave, Westbrook, CT 06498

  This unit is waterfront 1st floor main house. Kitchen, living room combination, 1 bath and bedroom. Heat and electric included. No laundry on the premises. One assigned parking space with no guest parking. No pets. No smoking. Awesome views of the ocean. First month rent and one month security. Credit, (credit minimum 700). background, eviction and application required. Rental Insurance required.

  Sharon Fox Carl Guild & Associates

  189 Seaside Ave, Westbrook, CT 06498
• 

  $4,900,000

  Sold Oct 16, 2025

  151 Kingfisher Ln, Westbrook, CT 06498

  • 6 Beds
  • 3.5 Baths
  • 6,182 Sq Ft
  • Built 1890

  Last Sold Summary

  • 15% Above List Price
  • $793/SF
  • 17 Days On Market

  Current Estimated Value $4,912,739

  Last Listing Agent Jackie Lyman Lyman Real Estate

  151 Kingfisher Ln, Westbrook, CT 06498
• 

  Est $834,601

  Not Listed For Sale

  101 Johnson Pond Ln, Westbrook, CT 06498

  • 4 Beds
  • 3 Baths
  • 3,759 Sq Ft
  • Built 1999

  101 Johnson Pond Ln, Westbrook, CT 06498

  Last Sold Summary

  • 4 Days On Market
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  /33

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  79 Wesley Ave, Westbrook, CT 06498

  Tucked away on a lush, private wooded lot, this authentic retreat offers the ultimate shoreline lifestyle just in time for summer. Perfectly blending natural privacy with coastal convenience, you're a short stroll from the sands of West Beach. The sun-drenched interior radiates warmth, highlighting a spacious, updated eat-in kitchen complete with premium appliances and granite countertops. Recent

  Annemarie Bellenoit Berkshire Hathaway NE Prop.

  79 Wesley Ave, Westbrook, CT 06498
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  /24

  $3,500 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,441 Sq Ft
  • House for Rent

  89 Grove Beach Rd S, Westbrook, CT 06498

  Two week JULY RENTAL, AVAILABLE 6/28/2026 - 7/11/2026 or 7/12/2026- 7/25/2026 Only steps to Grove Beach in this charming Cape style 3 bedroom, 1 & half bath home with one bedroom, the full bath and study on the main floor for easy living. The eat-in kitchen is open to the living room and looks out to the beautifully landscaped large back yard. The generously sized primary bedroom and third

  Mark McElrath William Pitt Sotheby's Int'l

  89 Grove Beach Rd S, Westbrook, CT 06498
• 

  $945,000

  Sold Dec 09, 2025

  321 Old Clinton Rd, Westbrook, CT 06498

  • 4 Beds
  • 3.5 Baths
  • 3,961 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Below List Price
  • $239/SF
  • 7 Days On Market

  Current Estimated Value $973,981

  Last Listing Agent Julia King William Raveis Real Estate

  321 Old Clinton Rd, Westbrook, CT 06498
• 

  Est $616,691

  Not Listed For Sale

  789 Toby Hill Rd, Westbrook, CT 06498

  • 3 Beds
  • 2.5 Baths
  • 2,834 Sq Ft
  • Built 1994

  789 Toby Hill Rd, Westbrook, CT 06498

  Last Sold Summary

  • 54 Days On Market
• 

  

  /23

  $549,999

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,312 Sq Ft

  39 Churchill Ln, Westbrook, CT 06498

  Westbrook Colonial | End-of-Cul-de-Sac Privacy | Minutes to the Shore Tucked at the end of a private cul-de-sac in one of the Connecticut Shoreline's most desirable coastal communities, this four-bedroom, 2,312 sq. ft. Colonial offers the kind of quiet, unhurried living that draws buyers to Westbrook - and keeps them here. Inside, generous windows draw natural light deep into the home,

  Pardi & Zucco Team William Pitt Sotheby's Int'l

  39 Churchill Ln, Westbrook, CT 06498
• 

  

  /22

  $3,800 Per Month

  • 3 Beds
  • 4 Baths
  • 2,353 Sq Ft
  • House for Rent

  58 Chapman Ave, Westbrook, CT 06498

  Relax and unwind in this beautifully renovated beach home nestled within the desirable Chapman Beach Association. Steps from the beach, this home has been tastefully updated and is equipped with the latest amenities. Boasting beaming hardwood floors throughout this academic rental available starting SEPTEMBER 1, 2026, features 3 bedrooms, 3 baths and has been completely remodeled. Enjoy views of

  Cheryl Cook Re/Max Valley Shore

  58 Chapman Ave, Westbrook, CT 06498
• 

  $179,000

  Sold Dec 04, 2025

  51 Linden Ave N, Westbrook, CT 06498

  • 2 Beds
  • 1 Bath
  • 754 Sq Ft
  • Built 2015

  Last Sold Summary

  • 6% Below List Price
  • $237/SF
  • 66 Days On Market

  Last Listing Agent Judith DuMouchel J.M. REALTY

  51 Linden Ave N, Westbrook, CT 06498
• 

  Est $949,236

  Not Listed For Sale

  1 Whittemore Place, Westbrook, CT 06498

  • 5 Beds
  • 3 Baths
  • 3,642 Sq Ft
  • Built 2001

  1 Whittemore Place, Westbrook, CT 06498

  Last Sold Summary

  • 2 Days On Market
• 

  

  /3

  $199,000

  $96K PRICE DROP

  • Land
  • 6.5 Acres
  • $30,615 per Acre

  0 Brainard Rd, Westbrook, CT 06498

  Nestled in the desirable Pond Meadow area, this private 6.5 Acre property offers a rare opportunity to create your ideal retreat in this idyllic coastal community. Featuring multiple leveled building sites, the land is well suited for flexibility and privacy. In initial feasibility study has been completed and additional site work would be necessary to begin construction. The property showcases a

  Rick Allen William Raveis Real Estate

  0 Brainard Rd, Westbrook, CT 06498
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  /10

  $3,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft
  • House for Rent

  19 Underway Dr, Westbrook, CT 06498

  Stunning waterfront home available from 9/15/26 - 5/15/27. Fully furnished and beautifully decorated. Central air. Front patio overlooking the water. Two bedrooms on first floor and waterfront master bedroom overlooking water on second floor. Full bath on both floors. No pets. No smokers. Owner/Agent.

  Mary Beth Murphy Shimkus, Murphy & Lemkuil

  19 Underway Dr, Westbrook, CT 06498
• 

  $119,900

  Sold Nov 20, 2025

  17 Woodsedge Ln, Westbrook, CT 06498

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1978

  Last Sold Summary

  • $114/SF
  • 23 Days On Market

  Last Listing Agent Chloe White KW Legacy Partners

  17 Woodsedge Ln, Westbrook, CT 06498
• 

  Est $796,206

  Not Listed For Sale

  27 Broadway S, Westbrook, CT 06498

  • 2 Beds
  • 2 Baths
  • 2,064 Sq Ft
  • Built 1900

  27 Broadway S, Westbrook, CT 06498

  Last Sold Summary

  • 16 Days On Market
• 

  

  /23

  $649,900

  Pending

  • 4 Beds
  • 3 Baths
  • 2,761 Sq Ft

  11a/11b Pond Circle Rd, Westbrook, CT 06498

  Stunning Fully Remodeled Legal Two-Family Home Discover this completely remodeled legal two-family residence, thoughtfully designed for modern living, investment, or multi-generational use. Every inch of this home has been upgraded with care and quality craftsmanship. Featuring brand-new HVAC and heating systems, new plumbing, and a 200-amp electrical panel, this property offers worry-free

  Steven Joseph Coldwell Banker Realty

  11a/11b Pond Circle Rd, Westbrook, CT 06498
• 

  $825,000

  Sold Oct 20, 2025

  6 Indian Trail, Westbrook, CT 06498

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft
  • Built 1944

  Last Sold Summary

  • 3% Below List Price
  • $760/SF
  • 46 Days On Market

  Current Estimated Value $859,801

  Last Listing Agent Susan Malan William Pitt Sotheby's Int'l

  6 Indian Trail, Westbrook, CT 06498
• 

  Est $669,649

  Not Listed For Sale

  1 Docs Hill Rd, Westbrook, CT 06498

  • 2 Beds
  • 3 Baths
  • 1,951 Sq Ft
  • Built 1989

  1 Docs Hill Rd, Westbrook, CT 06498

  Last Sold Summary

  • 126 Days On Market
• 

  

  /36

  $739,900

  • 3 Beds
  • 2 Baths
  • 2,651 Sq Ft

  67 Break Neck Hill Rd, Westbrook, CT 06498

  Welcome to the Treehouse. Literally and figuratively. A suspension bridge leads to a custom treehouse hidden among the trees, and that's only the beginning! Set on 4.5 private wooded acres just minutes from Connecticut's shoreline, this completely custom full-round log home offers the feeling of a mountain retreat with the convenience of the coast. Surrounded by mature trees, rock outcroppings,

  Carl Guild Carl Guild & Associates

  67 Break Neck Hill Rd, Westbrook, CT 06498

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