Southport, CT Homes

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  /40

  $2,800,000

  • 4 Beds
  • 2.5 Baths
  • 4,243 Sq Ft

  118 Roseville Rd, Westport, CT 06880

  This Westport residence is a meticulously executed Passive House retrofit of a modernist concrete home originally built in 1938. Few properties achieve this level of energy efficiency while also prioritizing non-toxic, health-conscious building materials. As you pass through the home's front entry gate and hear the gentle rhythm of tires over gravel, a striking and handsome facade comes into

  Tyler Della Valle Dow Della Valle

  118 Roseville Rd, Westport, CT 06880
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  /14

  $4,500 total monthly price

  • 3 Beds
  • 1 Bath
  • 816 Sq Ft
  • House for Rent

  108 College Place, Fairfield, CT 06824

  Enjoy all the activities of Fairfield Beach with this cosy cottage by the shore! This 3 bedroom bungalow gives you a perfect base camp to come and cool down after a day of exploring the beautiful sea-side town of Fairfield. A comfortable stroll from Penfield Beach, Veterans Park, and Lighthouse Point, you can fill each day with fun outdoor activities and a little taste of Beach Life. After a day

  Alex Kniffin Century 21 AllPoints Realty

  108 College Place, Fairfield, CT 06824
• 

  $460,000 Sold Jul 11, 2025

  321 Post Rd, Fairfield, CT 06824

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1944

  Last Sold Summary

  • 7% Below List Price
  • $411/SF
  • 87 Days On Market

  Current Estimated Value $502,825

  Last Listing Agent Maribeth Lightowler Coldwell Banker Realty

  321 Post Rd, Fairfield, CT 06824
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  Est $1,433,786 Not Listed For Sale

  37 Park Ln, Westport, CT 06880

  • 4 Beds
  • 3 Baths
  • 2,419 Sq Ft
  • Built 1960

  37 Park Ln, Westport, CT 06880

  Last Sold Summary

  • 4% Above List Price
  • $570/SF
  • 53 Days On Market

  Last Sold Price $1,380,000

  Last Listing Agent Gina Hackett Compass Connecticut, LLC
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  /23

  $792,000

  • 5 Beds
  • 3 Baths
  • 2,692 Sq Ft

  148 Alfred St, Bridgeport, CT 06605

  Attention investors and owner-occupants! Completely renovated three-family home located in the heart of desirable Black Rock, just a short walk to shopping, restaurants, and the train. This well-maintained property features two-bedroom units with full baths on the first and second floors, each offering spacious living areas and great natural light. The third floor offers a charming one-bedroom

  Tom Fitzpatrick Coldwell Banker Realty

  148 Alfred St, Bridgeport, CT 06605
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  /26

  $7,000 total monthly price

  • 5 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  116 College Place, Fairfield, CT 06824

  Bring the whole family! This 5 bedroom home has everything you need for the perfect summer getaway. A comfortable stroll from Penfield Beach, Veterans Park, and Lighthouse Point, you can fill each day with fun outdoor activities and a little taste of Beach Life. After a day on the water, come back ashore and check out Fairfield's vibrant downtown, which boasts and array of dining shopping, and

  Alex Kniffin Century 21 AllPoints Realty

  116 College Place, Fairfield, CT 06824
• 

  $765,000 Sold Oct 31, 2025

  115 Balmforth St, Bridgeport, CT 06605

  • 4 Beds
  • 2.5 Baths
  • 2,626 Sq Ft
  • Built 1956

  Last Sold Summary

  • 6% Above List Price
  • $291/SF
  • 5 Days On Market

  Current Estimated Value $765,200

  Last Listing Agent Joseph Passero William Raveis Real Estate

  115 Balmforth St, Bridgeport, CT 06605
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  Est $3,539,047 Not Listed For Sale

  64 Wright St, Westport, CT 06880

  • 5 Beds
  • 4.5 Baths
  • 3,805 Sq Ft
  • Built 1840

  64 Wright St, Westport, CT 06880

  Last Sold Summary

  • 7% Below List Price
  • $999/SF
  • 14 Days On Market

  Last Sold Price $3,800,000

  Last Listing Agent Joelle Malec William Raveis Real Estate
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  /38

  $539,500

  • 3 Beds
  • 1.5 Baths
  • 1,301 Sq Ft

  64 Moody Ave, Fairfield, CT 06825

  Old world charm and endless possibilities await you in this home. Tall ceilings and circular floorplan on the main level flows from one room to the next, giving a very lofty feel. Kitchen and bath are newer and show very well. Upstairs offers three bedrooms and a full bath that has also been redone. Basement has a newer furnace and on demand hot water heater (2014) and one room that is partially

  John Silos Munson Real Estate

  64 Moody Ave, Fairfield, CT 06825
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  /15

  $2,300 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,156 Sq Ft
  • House for Rent

  356 Midland St Unit 2, Bridgeport, CT 06605

  Rental in the heart of vibrant Black Rock! Spacious unit. This well-maintained home offers a perfect blend of historic charm with modern conveniences. The unit is on second floor features two spacious bedrooms, living and dining room with hardwood flooring, eat-in kitchen, full hall bath and pantry. The second floor has an enclosed porch. Large level back yard. Newer furnaces. The washer/dryer

  Priyanka Jain Coldwell Banker Realty

  356 Midland St Unit 2, Bridgeport, CT 06605
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  $515,000 Sold Dec 22, 2025

  378 Castle Ave, Fairfield, CT 06825

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft
  • Built 1930

  Last Sold Summary

  • 8% Above List Price
  • $413/SF
  • 18 Days On Market

  Current Estimated Value $493,624

  Last Listing Agent Jennifer DeLaurentis Compass Connecticut, LLC

  378 Castle Ave, Fairfield, CT 06825
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  Est $1,434,748 Not Listed For Sale

  9 Highland Rd, Westport, CT 06880

  • 4 Beds
  • 3.5 Baths
  • 3,283 Sq Ft
  • Built 1951

  9 Highland Rd, Westport, CT 06880

  Last Sold Summary

  • 30% Above List Price
  • $335/SF
  • 21 Days On Market

  Last Sold Price $1,100,000

  Last Listing Agent Georgia Wasserman Coldwell Banker Realty
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  /31

  $900,000

  • 8 Beds
  • 4 Baths
  • 3,360 Sq Ft

  301 Poplar St Unit 303, Bridgeport, CT 06605

  Welcome to 301 Poplar Street, a well-maintained 4-unit multifamily property located in the sought-after Black Rock section of Bridgeport. This income-producing property includes a total of 8 bedrooms and 4 bathrooms, with each unit featuring 2 bedrooms and 1 bathroom. The building provides spacious layouts, separate utilities, and strong rental potential in a high-demand location. Ideal for

  Justin Sudol Alpha Capital Realty, LLC

  301 Poplar St Unit 303, Bridgeport, CT 06605
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  /25

  $1,750 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,070 Sq Ft
  • Apartment for Rent

  35 Butler Ave Unit 5, Bridgeport, CT 06605

  Set inside a classic brick building, this light filled rental at 35 Butler Avenue, Unit 5 offers timeless character with a clean, move in ready feel. Hardwood floors run through the main living spaces, creating a warm and inviting backdrop for everyday living, while oversized windows bring in beautiful natural light throughout the day. The layout feels comfortable and functional, with a spacious

  Daniel Leyden KW Legacy Partners

  35 Butler Ave Unit 5, Bridgeport, CT 06605
• 

  $295,000 Sold Sep 08, 2025

  3250 Fairfield Ave Unit 210, Bridgeport, CT 06605

  • 2 Beds
  • 2 Baths
  • 1,145 Sq Ft
  • Built 2006

  Last Sold Summary

  • 6% Below List Price
  • $258/SF
  • 52 Days On Market

  Current Estimated Value $301,173

  Last Listing Agent Ariana Benesova eXp Realty

  3250 Fairfield Ave Unit 210, Bridgeport, CT 06605
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  Est $2,278,665 Not Listed For Sale

  12 Overlook Rd, Westport, CT 06880

  • 4 Beds
  • 2.5 Baths
  • 4,281 Sq Ft
  • Built 1929

  12 Overlook Rd, Westport, CT 06880

  Last Sold Summary

  • 3% Above List Price
  • $517/SF
  • 29 Days On Market

  Last Sold Price $2,215,000

  Last Listing Agent Susan Vanech Compass Connecticut, LLC
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  /32

  $1,550,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,797 Sq Ft

  341 Crestwood Rd, Fairfield, CT 06824

  A welcoming street. A connected neighborhood. A home designed to bring people together. Welcome to 341 Crestwood Road, where classic Fairfield charm meets quiet, modern comfort. Set along walkable streets with friendly faces, this is a place where community still matters and home feels truly settled, with easy walks to playgrounds, tennis, pickleball, and basketball courts, Whole Foods, and the

  Cindy Raney Coldwell Banker Realty

  341 Crestwood Rd, Fairfield, CT 06824
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  /24

  $60,000 total monthly price

  • 6 Beds
  • 5.5 Baths
  • 3,989 Sq Ft
  • House for Rent

  23 Sterling Dr, Westport, CT 06880

  Sterling Dr. Available from June 19 to August 24th. Spectacular views of the water from all rooms in this new, well appointed 5 bedroom home. Enjoy the heated INFINITY POOL with automatic cover (making it 100% safe) and a few minutes walk to Compo Cove or Compo Beaches by foot. The light-filled gourmet Kitchen has 2 sinks, 2 dishwashers, quartz countertops, and Sub-Zero/Wolf appliances. Enjoy the

  Derek Greene Derek Greene

  23 Sterling Dr, Westport, CT 06880
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  $822,500 Sold Nov 14, 2025

  363 Lake Ave, Bridgeport, CT 06605

  • 3 Beds
  • 1.5 Baths
  • 2,200 Sq Ft
  • Built 1931

  Last Sold Summary

  • 6% Above List Price
  • $374/SF
  • 29 Days On Market

  Current Estimated Value $793,034

  Last Listing Agent Geo Crume Keller Williams Realty

  363 Lake Ave, Bridgeport, CT 06605
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  Est $993,686 Not Listed For Sale

  45 Drumlin Rd, Westport, CT 06880

  • 3 Beds
  • 2 Baths
  • 1,348 Sq Ft
  • Built 1951

  45 Drumlin Rd, Westport, CT 06880

  Last Sold Summary

  • 20% Above List Price
  • $612/SF
  • 9 Days On Market

  Last Sold Price $825,000

  Last Listing Agent Sally Bohling Coldwell Banker Realty
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  /10

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,326 Sq Ft

  412 Dewey St, Bridgeport, CT 06605

  Welcome to this well-maintained single-family home in Bridgeport, CT featuring 4 spacious bedrooms and 2 full bathrooms. Enjoy an open and comfortable layout with central air, a finished basement perfect for additional living space or entertainment, and a nice backyard ideal for gatherings or relaxation. Conveniently located near schools, shopping, and major highways-this move-in-ready home

  Rosania Melo Rosania Melo Broker

  412 Dewey St, Bridgeport, CT 06605
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  /19

  $3,000 total monthly price

  • 1 Bed
  • 1 Bath
  • 796 Sq Ft
  • House for Rent

  44 Roseville Rd, Westport, CT 06880

  Charming 1-bedroom cottage with den available for yearly rental, unfurnished. Privately set back from the main house on a nicely landscaped property with a small pond and outdoor patio. The cottage offers a practical, efficient layout with a spacious entryway, dining area, and galley kitchen. The living room features a working wood-burning fireplace, and the den provides flexible space suitable

  Stephen Pratt Keller Williams Realty

  44 Roseville Rd, Westport, CT 06880
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  $616,500 Sold Sep 29, 2025

  694 Jennings Rd, Fairfield, CT 06824

  • 3 Beds
  • 1 Bath
  • 1,560 Sq Ft
  • Built 1947

  Last Sold Summary

  • 1% Below List Price
  • $395/SF
  • 45 Days On Market

  Current Estimated Value $627,663

  Last Listing Agent Hilary Del Aguila Ortiz YellowBrick Real Estate LLC

  694 Jennings Rd, Fairfield, CT 06824
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  Est $1,095,349 Not Listed For Sale

  137 Lansdowne, Westport, CT 06880

  • 2 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • Built 1984

  137 Lansdowne, Westport, CT 06880

  Last Sold Summary

  • 7% Above List Price
  • $488/SF
  • 21 Days On Market

  Last Sold Price $1,025,000

  Last Listing Agent Heidi Cinder William Raveis Real Estate
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  /16

  $749,900

  • 7 Beds
  • 4.5 Baths
  • 4,669 Sq Ft

  155 Brooklawn Ave, Bridgeport, CT 06604

  Stunning French chalet-style located in the historic Brooklawn neighborhood, with 10 rooms, 7 bedrooms, 4.5 baths, partial basement, 2 car garage, large lot, plus separate remodeled apartment consisting of office, eat in kitchen, living room, bedroom and full bathroom. This property is ideal for a home office business with mixed use zoning and plenty of parking. A rare opportunity to buy a grand

  Luisa Dias RE/MAX Right Choice

  155 Brooklawn Ave, Bridgeport, CT 06604
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  /36

  $33,000 total monthly price

  • 3 Beds
  • 3.5 Baths
  • 3,815 Sq Ft
  • House for Rent

  47 Woodside Ave, Westport, CT 06880

  Summer in Westport! Clean living at its best. A home prepared with non-chemical, organic products. The owners live here year round with ZERO FRAGRANCE. Owners are extremely sensitive to fragrance so only CLEAN LIVING TENANTS take interest. Organic, non fragrance, non chemical, hypo-allergenic product home. Products will remain in the home for summer tenant to utilize during their stay. This is

  Elizabeth Altobelli William Raveis Real Estate

  47 Woodside Ave, Westport, CT 06880
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  $2,250,000 Sold Aug 11, 2025

  7 Mansfield Place, Westport, CT 06880

  • 4 Beds
  • 4 Baths
  • 3,270 Sq Ft
  • Built 1900

  Last Sold Summary

  • 6% Below List Price
  • $688/SF
  • 34 Days On Market

  Current Estimated Value $2,251,299

  Last Listing Agent Judy Michaelis Coldwell Banker Realty

  7 Mansfield Place, Westport, CT 06880
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  Est $1,546,743 Not Listed For Sale

  215 Lansdowne, Westport, CT 06880

  • 2 Beds
  • 2.5 Baths
  • 2,450 Sq Ft
  • Built 1985

  215 Lansdowne, Westport, CT 06880

  Last Sold Summary

  • 3% Above List Price
  • $612/SF
  • 46 Days On Market

  Last Sold Price $1,500,000

  Last Listing Agent Julie Vanderblue Higgins Group Real Estate
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  /40

  $429,900 Pending

  • 2 Beds
  • 1 Bath
  • 791 Sq Ft

  165 Bennett St, Bridgeport, CT 06605

  Nestled in the heart of Black Rock.......Welcome to Evergreen Cottage! The perfect blend of Simplicity, comfort & Tranquility! Beautifully maintained and rich in details such as high ceilings, craftsman-style moldings , crisp decor & an abundance of natural light in every room. Updated kitchen and bath, gas furnace & sewer line. Roof fully replaced 2021. Original cedar clapboards and trim

  Mary Amenda William Pitt Sotheby's Int'l

  165 Bennett St, Bridgeport, CT 06605
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  /7

  $1,800 total monthly price

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  649 Bridgeoort Ave, Bridgeport, CT 06607

  2 BEDROOMS APARTMENT,BIG KITCHEN AND LIVING ROOM,ONE BATHROOM,NEW APPLIANCES, PARKING FOR ONE CAR. 2 MONTHS SECURITY DEPOSIT ..CREDIT, REFERENCES, PROOF OF INCOME., LEASE.

  Francisco Sandoval Keller Williams Realty Prtnrs.

  649 Bridgeoort Ave, Bridgeport, CT 06607
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  $1,800,000 Sold Dec 10, 2025

  10 Twin Falls Ln, Westport, CT 06880

  • 4 Beds
  • 3 Baths
  • 4,231 Sq Ft
  • Built 1934

  Last Sold Summary

  • 20% Below List Price
  • $425/SF
  • 159 Days On Market

  Current Estimated Value $1,800,117

  Last Listing Agent Kit Tingley Higgins Group Bedford Square

  10 Twin Falls Ln, Westport, CT 06880
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  Est $1,168,007 Not Listed For Sale

  205 Lansdowne, Westport, CT 06880

  • 2 Beds
  • 2.5 Baths
  • 2,050 Sq Ft
  • Built 1985

  205 Lansdowne, Westport, CT 06880

  Last Sold Summary

  • 22% Above List Price
  • $468/SF
  • 41 Days On Market

  Last Sold Price $960,000

  Last Listing Agent Joan Wright Compass Connecticut, LLC
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  /20

  $2,800,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 4,000 Sq Ft

  53 Cross Hwy, Westport, CT 06880

  Proposed New Construction, build this beautiful home or let's design your dream home!! 1 acre lot with a brook sets up perfectly for a walk-out basement. Great location close to everything. Quality custom home builder with 25 years experience and over 150 homes built. Existing home to be torn down, taxes shown reflect existing home.

  Phil Pedros Philips Real Estate

  53 Cross Hwy, Westport, CT 06880
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  /25

  $1,995 total monthly price

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • House for Rent

  2806 Fairfield Ave Unit 301, Bridgeport, CT 06605

  The Newly Renovated Wanis Building! Spectacular third floor, one bedroom, one bathroom end unit! The unit has an open living, dining, kitchen area, the appliances are stainless steel and there is also a stackable washer and dryer. This nice and bright end unit with exposed brick is ideally located in the Black Rock restaurant and entertainment district and is convenient to the Black Rock Train

  John Kleps Berkshire Hathaway NE Prop.

  2806 Fairfield Ave Unit 301, Bridgeport, CT 06605
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  $1,150,000 Sold Nov 07, 2025

  11 Oldfield Dr, Fairfield, CT 06824

  • 4 Beds
  • 2 Baths
  • 2,124 Sq Ft
  • Built 1950

  Last Sold Summary

  • 16% Above List Price
  • $541/SF
  • 6 Days On Market

  Current Estimated Value $1,120,399

  Last Listing Agent Wendy Ryan Brown Harris Stevens

  11 Oldfield Dr, Fairfield, CT 06824
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  Est $705,914 Not Listed For Sale

  24 Oakview Cir, Westport, CT 06880

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1985

  24 Oakview Cir, Westport, CT 06880

  Last Sold Summary

  • 43% Above List Price
  • $469/SF
  • 20 Days On Market

  Last Sold Price $495,000

  Last Listing Agent Carolina Norwick Compass Connecticut, LLC
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  /7

  $755,000

  • 5 Beds
  • 3 Baths
  • 2,483 Sq Ft

  855 Brewster St Unit 857, Bridgeport, CT 06605

  An incredible investment opportunity in a highly desirable Black Rock Neighborhood. This well maintained 3 Family property is perfect for investors or owner occupied. Ideally located within walking distance to the Fairfield Metro Train Station, shops and restaurants along Fairfield Ave. It's a short drive to I-95 and Downtown Fairfield and Black Rock Turnpike. This 3 Family home has 5 Bedrooms, 3

  Doug Munson Munson Real Estate

  855 Brewster St Unit 857, Bridgeport, CT 06605
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  /14

  $3,695 total monthly price

  • 1 Bed
  • 1 Bath
  • 845 Sq Ft
  • House for Rent

  78 Unquowa Place, Fairfield, CT 06824

  Ultra Chic 1 Bedroom. The BEST Metro North commuter location in Fairfield County! Contemporary Luxury Meets Urban Chic in Downtown Fairfield Step into Unit #304 at the Fairfield Station Lofts, the premier Metro-North commuter location in Fairfield County, where sleek city sophistication seamlessly fuses with timeless Connecticut charm. Designed by the award-winning Granoff Architects, this

  George Gardone Keller Williams Prestige Prop.

  78 Unquowa Place, Fairfield, CT 06824
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  $1,250,000 Sold Jun 06, 2025

  68 Grove Point, Westport, CT 06880

  • 4 Beds
  • 3 Baths
  • 2,375 Sq Ft
  • Built 1962

  Last Sold Summary

  • 4% Below List Price
  • $526/SF
  • 38 Days On Market

  Current Estimated Value $1,236,821

  Last Listing Agent Erica Acheychek Compass Connecticut, LLC

  68 Grove Point, Westport, CT 06880
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  Est $566,244 Not Listed For Sale

  28 Crescent Park Rd, Westport, CT 06880

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1986

  28 Crescent Park Rd, Westport, CT 06880

  Last Sold Summary

  • 60% Above List Price
  • $308/SF
  • 94 Days On Market

  Last Sold Price $355,000

  Last Listing Agent Terence Dominick Exceptional Real Estate LLC

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