Westbrook, CT Homes

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  $1,195,000

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

  448 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

  (860) 854-2784

  448 Grove Beach Rd N, Westbrook, CT 06498
• Explore Westbrook

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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
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  $615,000 Sold Jun 17, 2025

  586 Essex Rd, Westbrook, CT 06498

  • 3 Beds
  • 2 Baths
  • 1,569 Sq Ft
  • Built 1972

  Last Sold Summary

  • 5% Below List Price
  • $392/SF
  • 15 Days On Market

  Current Estimated Value $642,017

  Last Listing Agent Pardi & Zucco Team William Pitt Sotheby's Int'l

  586 Essex Rd, Westbrook, CT 06498
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  Est $1,482,398 Not Listed For Sale

  165 Captains Dr, Westbrook, CT 06498

  • 2 Beds
  • 3 Baths
  • 2,104 Sq Ft
  • Built 1996

  165 Captains Dr, Westbrook, CT 06498

  Last Sold Summary

  • 4% Below List Price
  • $732/SF
  • 1 Day On Market

  • Last Sold Price $1,540,000
  • May 09, 2025

  Last Listing Agent Robin Morrell - Guilford William Pitt
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  $419,000

  • 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

  (860) 351-4080

  405 Pond Meadow Rd, Westbrook, CT 06498
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  Call for Price

  • 1 Bed

  34 Worthington Dr, Westbrook, CT 06498

  Worthington Manor

  (959) 265-0586

  

  34 Worthington Dr, Westbrook, CT 06498
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  $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
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  Est $918,862 Not Listed For Sale

  64 Chapman Ave, Westbrook, CT 06498

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft
  • Built 2000

  64 Chapman Ave, Westbrook, CT 06498

  Last Sold Summary

  • 6% Above List Price
  • $542/SF
  • 41 Days On Market

  • Last Sold Price $865,000
  • Apr 24, 2025

  Last Listing Agent Michael Truong eXp Realty
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  $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

  (860) 831-4967

  448 A - B Grove Beach Rd 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, 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!! THIS IS AN ACADEMIC RENTAL FROM SEPT. TO JUNE 2026 !!!

  Salome Kirkutis SKS Realty

  14 Leeway Dr, Westbrook, CT 06498
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  $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 $620,213

  Last Listing Agent Amaurys Valdera Brokerbe Inc.

  10 Winterberry Cir, Westbrook, CT 06498
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  Est $2,188,405 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

  • 4% Above List Price
  • $836/SF
  • 83 Days On Market

  • Last Sold Price $2,100,000
  • Dec 04, 2024

  Last Listing Agent Jackie Lyman Lyman Real Estate
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  /20

  $134,900

  • 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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  $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
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  $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 $450,461

  Last Listing Agent Thomas Mele Dorrance Realty

  207 Pettipaug Rd, Westbrook, CT 06498
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  Est $533,527 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

  • 2% Above List Price
  • $298/SF
  • 15 Days On Market

  • Last Sold Price $525,000
  • Jul 08, 2024

  Last Listing Agent Phoebe Schreiner William Pitt
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  /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
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  /22

  $4,000 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 Ocotober 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
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  $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 $3,283,207

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

  166 Fiske Ln, Westbrook, CT 06498
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  Est $702,232 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

  • 23% Above List Price
  • $394/SF
  • 38 Days On Market

  • Last Sold Price $570,000
  • Apr 10, 2024

  Last Listing Agent Carol Ieronimo William Raveis Real Estate
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  /39

  $648,000

  • 4 Beds
  • 2.5 Baths
  • 2,361 Sq Ft

  126 Magna Ln, Westbrook, CT 06498

  Experience the ultimate in Victorian Cottage Chic with this 1890 gem, perfectly set on a level, lush 0.70-acre lot. This 2,300+ sq. ft. home spans three stories, preserving the authentic soul and historic character of a classic coastal retreat. The home welcomes you with a charming foyer and oversized windows that flood the space with natural light. Interior highlights include original hardwood

  Maria Phillips William Raveis Real Estate

  126 Magna Ln, Westbrook, CT 06498
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  /17

  $1,700 Per Month

  • 1 Bed
  • 2 Baths
  • 2,390 Sq Ft
  • House for Rent

  8 Lewis Ave, Westbrook, CT 06498

  Welcome to your year-round coastal retreat! This spacious one-bedroom rental boasts an oversized living area, two full bathrooms, and a layout designed for comfort and ease. Located in a private beach community with effortless access to Island View Beach, this home also features off-street parking, a peaceful backyard perfect for unwinding, generous closet space, and ample room for storage.

  Craig Milton Re/Max Valley Shore

  8 Lewis Ave, Westbrook, CT 06498
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  $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 $503,606

  Last Listing Agent Ferdinand Giacinto RE/MAX on the Bay

  1 Spencer Plains Rd, Westbrook, CT 06498
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  Est $1,938,743 Not Listed For Sale

  60 Captains Dr, Westbrook, CT 06498

  • 3 Beds
  • 3 Baths
  • 2,534 Sq Ft
  • Built 1965

  60 Captains Dr, Westbrook, CT 06498

  Last Sold Summary

  • 2% Below List Price
  • $779/SF
  • 2 Days On Market

  • Last Sold Price $1,975,000
  • May 17, 2023

  Last Listing Agent Edward Hillyer William Raveis Real Estate
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  $699,900

  • 4 Beds
  • 2.5 Baths
  • 2,831 Sq Ft

  85 McVeagh Rd, Westbrook, CT 06498

  Exceptional Country Living Close to Town - Westbrook, CT Discover the perfect blend of country charm and modern comfort in this beautifully maintained farmhouse colonial, ideally located in the scenic shoreline town of Westbrook. Built in 2002 by a respected local builder, this spacious home offers over 2,800 sq. ft. of living space, plus additional finished (unheated) basement area-plenty of

  Lynn Lehrman Re/Max Valley Shore

  85 McVeagh Rd, Westbrook, CT 06498
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  $2,500 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • House for Rent

  708 E Pond Meadow Rd, Westbrook, CT 06498

  3 beds, 1 bath; Calm and cozy country retreat; small town feel; local train station; close to Long Island Sound beaches; outlet shopping; great restaurants; and a famous resort and spa nearby. HEAT AND HOT WATER INCLUDED. Includes garage, back deck with outdoor grill and spacious back yard. Tenant pays electricity and cable/wifi. Easy highway commute to New London and New Haven. RentSpree

  Dee Alfiero William Raveis Real Estate

  708 E Pond Meadow Rd, Westbrook, CT 06498
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  $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 $4,544,286

  Last Listing Agent Jackie Lyman Lyman Real Estate

  151 Kingfisher Ln, Westbrook, CT 06498
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  Est $826,704 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

  • 14% Above List Price
  • $193/SF
  • 4 Days On Market

  • Last Sold Price $725,000
  • Aug 09, 2023

  Last Listing Agent Craig Milton RE/MAX
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  $1,045,000

  • 3 Beds
  • 2 Baths
  • 1,459 Sq Ft

  224 Salt Island Rd, Westbrook, CT 06498

  Tucked away in a charming shoreline setting, this retreat on Salt Island Road is directly across the street from Long Island Sound with breathtaking unobstructed water views. Enjoy coastal living in this inviting home featuring bright and comfortable living spaces designed for relaxing summer days and peaceful evenings by the shore. Wake up to refreshing sea breezes and take in stunning views of

  Jackie Lyman Lyman Real Estate

  224 Salt Island 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
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  $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 $975,737

  Last Listing Agent Julia King William Raveis Real Estate

  321 Old Clinton Rd, Westbrook, CT 06498
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  Est $592,693 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

  • 15% Above List Price
  • $182/SF
  • 54 Days On Market

  • Last Sold Price $515,000
  • Mar 21, 2024

  Last Listing Agent Katherine Luby Coldwell Banker Realty
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  /28

  $1,275,000

  • 3 Beds
  • 3 Baths
  • 2,475 Sq Ft

  6 Leeway Dr, Westbrook, CT 06498

  Pristine year round Contemporary home with views of the Marina at Pilots Point. Relax on the 12'x35' deck with an electric retractable awning or just enjoy the evening setting sun. The back patio has an enclosed shower and an area to grill. This home has been renovated and features many upgrades. The family room on the first floor could have an office. The Great room on the 2nd level has windows

  Salome Kirkutis SKS Realty

  6 Leeway Dr, Westbrook, CT 06498
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  $1,685,000 Sold May 29, 2025

  204 Old Kelsey Point Rd, Westbrook, CT 06498

  • 3 Beds
  • 3 Baths
  • 1,742 Sq Ft
  • Built 1920

  Last Sold Summary

  • 6% Below List Price
  • $967/SF
  • 9 Days On Market

  Current Estimated Value $1,782,816

  Last Listing Agent Libby Waldron Coldwell Banker Realty

  204 Old Kelsey Point Rd, Westbrook, CT 06498
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  Est $946,364 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

  • 11% Above List Price
  • $235/SF
  • 2 Days On Market

  • Last Sold Price $855,000
  • Jun 23, 2023

  Last Listing Agent Robin Linares William Pitt
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  /31

  $875,000

  • 3 Beds
  • 3 Baths
  • 1,560 Sq Ft

  100 2nd Ave, Westbrook, CT 06498

  Welcome to 100 Second Avenue, located in sought-after Stannard Beach. A coastal gem offering the perfect blend of lifestyle and location. Enjoy water views that bring a sense of calm and coastal charm to everyday living. This property is ideally situated to take advantage of a vibrant, community. Amenities at Stannard Beach include a new playground, pickleball, tennis, basketball courts, and it's

  Jackie Lyman Lyman Real Estate

  100 2nd Ave, Westbrook, CT 06498
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  $585,000 Sold Jun 23, 2025

  37 Menunketesuck Rd, Westbrook, CT 06498

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

  Last Sold Summary

  • 7% Below List Price
  • $609/SF
  • 33 Days On Market

  Current Estimated Value $612,678

  Last Listing Agent Sue Woods William Pitt Sotheby's Int'l

  37 Menunketesuck Rd, Westbrook, CT 06498
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  Est $789,727 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

  • 17% Above List Price
  • $327/SF
  • 16 Days On Market

  • Last Sold Price $675,000
  • Jul 03, 2023

  Last Listing Agent Katie Westrin William Raveis Real Estate
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  $1,295,000

  • 4 Beds
  • 5 Baths
  • 4,465 Sq Ft

  53 Oakridge Dr, Westbrook, CT 06498

  Can you imagine 8 acres of privacy surrounding your own pristine 3 acre lake, stocked with bass, just steps from your 4 bedroom home and minutes from Long Island Sound and walking distance from the high school? It's one thing to live on a lake. It's quite another to own and enjoy one. Welcome to the Lake House at 53 Oakridge Drive in the Shoreline Town of Westbrook, Connecticut. Imagine, waking

  John Campbell Compass Connecticut, LLC

  53 Oakridge Dr, Westbrook, CT 06498
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  $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

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