Southport, CT Homes

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  $1,149,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,954 Sq Ft

  281 Wood House Rd, Fairfield, CT 06824

  Located at 281 Wood House Rd in Fairfield, CT, this beautifully updated home seamlessly blends modern comfort with timeless charm. Offering four spacious bedrooms, including a primary en-suite with a walk-in closet, it provides plenty of flexibility for family, guests, or a home office. The bright and inviting living spaces include a sunlit living room and a cozy family room conveniently situated

  Jennifer Friedman Compass Connecticut, LLC

  281 Wood House Rd, Fairfield, CT 06824
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  $6,250 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 3,500 Sq Ft
  • Townhouse for Rent

  62 Soundview Ave, Fairfield, CT 06825

  Be the first to occupy this brand new townhome! This is an entertainers paradise with a sunny main level open concept layout featuring a stunning kitchen with walk in pantry, Quartz countertops, wine chiller and sliders to the beautfully landscaped paver patio and yard. Office/ bonus room and 1/2 bath complete the main level. Head up to the luxurious primary bedroom after a long day- 2 closets,

  Donna Gladstein ERA Insite Realty Services

  62 Soundview Ave, Fairfield, CT 06825
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  $2,100,000 Sold May 14, 2025

  387 Main St, Westport, CT 06880

  • 4 Beds
  • 4 Baths
  • 3,016 Sq Ft
  • Built 1840

  Last Sold Summary

  • 7% Below List Price
  • $696/SF
  • 28 Days On Market

  Current Estimated Value $2,081,039

  Last Listing Agent Ryan Sullivan Berkshire Hathaway NE Prop.

  387 Main St, Westport, CT 06880
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  Est $1,832,792 Not Listed For Sale

  7 Drumlin Rd, Westport, CT 06880

  • 3 Beds
  • 4 Baths
  • 3,018 Sq Ft
  • Built 1952

  7 Drumlin Rd, Westport, CT 06880

  Last Sold Summary

  • 4% Below List Price
  • $630/SF
  • 114 Days On Market

  Last Sold Price $1,900,000

  Last Listing Agent Jennifer Leahy Compass Connecticut, LLC
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  $1,185,000

  • 4 Beds
  • 3 Baths
  • 2,622 Sq Ft

  23 Bridge St, Westport, CT 06880

  Set in the heart of Westport, 23 Bridge Street offers a rare opportunity to own a character-rich home at a price point that is increasingly hard to find in town. Ideally located just minutes from the Metro-North Railroad train station, this property delivers exceptional everyday convenience for commuters and weekend explorers alike. The home borders over 1.5 acres of town-owned open space, a

  Matthew Nuzie RE/MAX Right Choice

  23 Bridge St, Westport, CT 06880
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  $6,000 total monthly price

  • 4 Beds
  • 1 Bath
  • 1,267 Sq Ft
  • House for Rent

  27 Reef Ct, Fairfield, CT 06824

  Welcome to this newly refreshed coastal home, ideally situated in the desirable Fairfield Beach area. Bright, spacious, and filled with natural light, this 4-bedroom, 1-bath gem offers the perfect blend of comfort and convenience. Just a short walk to Penfield Beach and the Post Road, the location is unbeatable-enjoy beachside living while staying close to great restaurants, shops, and local

  Carla Foote William Raveis Real Estate

  27 Reef Ct, Fairfield, CT 06824
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  $1,800,000 Sold Aug 21, 2025

  127 College Park Dr, Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 2,704 Sq Ft
  • Built 1980

  Last Sold Summary

  • 24% Above List Price
  • $666/SF
  • 8 Days On Market

  Current Estimated Value $1,758,600

  Last Listing Agent Chrissie Rodriguez Higgins Group Real Estate

  127 College Park Dr, Fairfield, CT 06824
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  Est $2,333,776 Not Listed For Sale

  3 Sterling Dr, Westport, CT 06880

  • 4 Beds
  • 3.5 Baths
  • 3,129 Sq Ft
  • Built 1912

  3 Sterling Dr, Westport, CT 06880

  Last Sold Summary

  • 26% Above List Price
  • $591/SF
  • 24 Days On Market

  Last Sold Price $1,850,000

  Last Listing Agent Meredith Cohen Serhant Connecticut, LLC
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  $189,000

  • 1 Bed
  • 1 Bath
  • 927 Sq Ft

  80 Cartright St Unit 2F, Bridgeport, CT 06604

  Welcome to 80 Cartright Street, ideally located right on the Fairfield/Bridgeport line! This spacious 1-bedroom, 1-bath condo offers nearly 1,000 sq ft of updated living space with beautiful views from a private balcony. The remodeled kitchen features butcher block countertops, new stainless steel appliances, a white subway tile backsplash, and space for a dining table. The oversized primary

  Hillary Waite William Raveis Real Estate

  80 Cartright St Unit 2F, Bridgeport, CT 06604
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  $6,250 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 3,500 Sq Ft
  • Townhouse for Rent

  74 Soundview Ave, Fairfield, CT 06825

  Be the first to occupy this brand new townhome! This is an entertainers paradise with a sunny open concept layout featuring a stunning kitchen with walk in pantry, Quartz countertops, wine chiller and sliders to the beautfully landscaped paver patio and yard. Office/ bonus room and 1/2 bath complete the main level. Head up to the luxurious primary bedroom after a long day- 2 closets, paneled

  Donna Gladstein ERA Insite Realty Services

  74 Soundview Ave, Fairfield, CT 06825
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  $740,000 Sold Nov 19, 2025

  230 Saugatuck Ave Unit 6, Westport, CT 06880

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Above List Price
  • $617/SF
  • 75 Days On Market

  Last Listing Agent Scott Wright RE/MAX Right Choice

  230 Saugatuck Ave Unit 6, Westport, CT 06880
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  Est $954,711 Not Listed For Sale

  82 Saugatuck Ave, Westport, CT 06880

  • 4 Beds
  • 3 Baths
  • 2,041 Sq Ft
  • Built 1920

  82 Saugatuck Ave, Westport, CT 06880

  Last Sold Summary

  • 19% Above List Price
  • $393/SF
  • 15 Days On Market

  Last Sold Price $802,000

  Last Listing Agent Jay Cannone William Raveis Real Estate
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  $820,000

  • 3 Beds
  • 2 Baths
  • 1,395 Sq Ft

  1353 Mill Plain Rd, Fairfield, CT 06824

  Welcome to this beautifully updated home in a prime Fairfield location - just minutes to top-rated schools, vibrant dining, shopping, cafes, Metro North train, and Fairfield's stunning beaches. The sun-filled main level features a newly renovated kitchen with crisp white cabinetry, quartz countertops, stainless steel appliances, and clean modern finishes. Hardwood floors run throughout, creating

  Christine Oleynick Keller Williams Realty

  1353 Mill Plain Rd, Fairfield, CT 06824
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  $3,750 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,060 Sq Ft
  • House for Rent

  87b Red Coat Rd, Westport, CT 06880

  Wonderful private legal two bedroom carriage house on the Saugatuck River private estate. Freshly painted with wall to wall carpet in bedrooms and loft area. Wood floors in the living room with vaulted ceiling. washer / dryer in unit. Bonus loft for storage. This charming home is available for short or long term rental great for 1/2 people. Owner might consider use of the pool depending on lease.

  Rebecca Ellsley Higgins Group Bedford Square

  87b Red Coat Rd, Westport, CT 06880
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  $2,270,000 Sold May 29, 2025

  2031 Redding Rd, Fairfield, CT 06824

  • 7 Beds
  • 6 Baths
  • 5,291 Sq Ft
  • Built 1810

  Last Sold Summary

  • 1% Below List Price
  • $429/SF
  • 102 Days On Market

  Last Listing Agent Katie O'Grady Compass Connecticut, LLC

  2031 Redding Rd, Fairfield, CT 06824
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  Est $3,456,930 Not Listed For Sale

  2 Whippoorwill Ln, Westport, CT 06880

  • 8 Beds
  • 6.5 Baths
  • 6,057 Sq Ft
  • Built 2007

  2 Whippoorwill Ln, Westport, CT 06880

  Last Sold Summary

  • 22% Above List Price
  • $466/SF
  • 77 Days On Market

  Last Sold Price $2,825,000

  Last Listing Agent Linda Skolnick Coldwell Banker Realty
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  $15,000,000

  • 7 Beds
  • 10 Baths
  • 9,129 Sq Ft

  4800 Congress St, Fairfield, CT 06824

  The Ultimate East Coast Sanctuary-Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street and engineered for the world's most discerning icons who demand seclusion with proximity to NYC. This 38.91-acre compound is a one of a kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music,

  Leslie Razook William Pitt Sotheby's Int'l

  4800 Congress St, Fairfield, CT 06824
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  $3,250 total monthly price

  • 2 Beds
  • 1 Bath
  • 740 Sq Ft
  • House for Rent

  315 Main St, Westport, CT 06880

  LOCATION, LOCATION, LOCATION...Fully renovated 2-bedroom, 1-bath rental located just half a mile from downtown Westport, offering scenic views overlooking the Saugatuck River. This unit includes private parking, an in-unit washer and dryer, and a private storage unit. The interior is entirely brand new, featuring new windows, updated flooring and carpeting, an eat-in kitchen with stainless steel

  Kim Vartuli Keller Williams Realty

  315 Main St, Westport, CT 06880
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  $665,000 Sold Jan 07, 2026

  105 Fox St Unit 107, Bridgeport, CT 06605

  • 6 Beds
  • 3 Baths
  • 3,258 Sq Ft
  • Built 1907

  Last Sold Summary

  • 1% Above List Price
  • $204/SF
  • 63 Days On Market

  Current Estimated Value $596,067

  Last Listing Agent John Kleps Berkshire Hathaway NE Prop.

  105 Fox St Unit 107, Bridgeport, CT 06605
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  Est $2,935,258 Not Listed For Sale

  142 Compo Rd N, Westport, CT 06880

  • 5 Beds
  • 5 Baths
  • 5,273 Sq Ft
  • Built 2016

  142 Compo Rd N, Westport, CT 06880

  Last Sold Summary

  • 10% Above List Price
  • $506/SF
  • 7 Days On Market

  Last Sold Price $2,670,000

  Last Listing Agent Leslie Clarke Compass Connecticut, LLC
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  $5,300,000 Under Contract

  • 5 Beds
  • 6 Baths
  • 6,020 Sq Ft

  24 Compo Pkwy, Westport, CT 06880

  Rare opportunity to live on one of Westport's most desirable Compo Beach cul-de-sacs. Beautifully restored and reimagined for today's lifestyle, this character filled 1925 Colonial features beamed ceilings, exposed stone, four fireplaces and more. Grand entertaining spaces include an expansive Dining Rm/Living Rm with 10' ceilings and two FPLS, a bright modern Kitchen and Family Rm w/FPL, a

  Elayne Landau Compo Point Properties

  24 Compo Pkwy, Westport, CT 06880
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  $2,400 total monthly price

  • 2 Beds
  • 1 Bath
  • 2,078 Sq Ft
  • House for Rent

  29 Hubbell St, Bridgeport, CT 06605

  Welcome to this first floor two bedroom apartment in a quiet multi-family on a dead end street, just minutes from Fairfield Ave shopping, dining, and public transportation. Bright and conveniently located, it's perfect for easy city living.

  Jeannette Zapata Home Sweet Home Realty & Devel

  29 Hubbell St, Bridgeport, CT 06605
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  $1,769,000 Sold Dec 19, 2025

  61 Edgewater Commons Ln, Westport, CT 06880

  • 4 Beds
  • 3.5 Baths
  • 3,397 Sq Ft
  • Built 1988

  Last Sold Summary

  • 31% Below List Price
  • $521/SF
  • 84 Days On Market

  Current Estimated Value $1,754,917

  Last Listing Agent Maria Tziolis William Pitt Sotheby's Int'l

  61 Edgewater Commons Ln, Westport, CT 06880
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  Est $2,199,206 Not Listed For Sale

  18 Silver Brook Rd, Westport, CT 06880

  • 4 Beds
  • 5 Baths
  • 5,253 Sq Ft
  • Built 1952

  18 Silver Brook Rd, Westport, CT 06880

  Last Sold Summary

  • 16% Above List Price
  • $362/SF
  • 18 Days On Market

  Last Sold Price $1,900,000

  Last Listing Agent Catherine Blount Coldwell Banker Realty
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  $4,400,000 Open Sat 1PM - 3PM

  • 8 Beds
  • 9 Baths
  • 8,412 Sq Ft

  32 Webb Rd, Westport, CT 06880

  This luxury 2026 Colonial at 32 Webb Road offers 8,412 sq ft of open-concept living on a 0.64-acre lot, tucked away on a quiet cul-de-sac in the heart of Westport. All eight bedrooms are ensuite, and nine bathrooms include a spacious primary suite with a walk-in closet and a private balcony. The gourmet kitchen features top-tier appliances and custom cabinetry, flowing seamlessly into sun-filled

  Judy Michaelis Coldwell Banker Realty

  32 Webb Rd, Westport, CT 06880
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  $2,700 total monthly price

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  610 Tunxis Hill Rd Unit 2, Fairfield, CT 06825

  Newly updated apartment complete with utilities included (Gas, Heat, Hot Water, Electricity). Owner has taken special care of both units while remodeling. New Appliances. New Windows, New Roof. New Paint. New counters. New Bathroom Fixtures.... List goes on. Make this your own. Sun drenched with huge windows and tons of natural light. 2 large bedrooms and 1 full bath. Open concept from kitchen

  Michael Debiase Keller Williams Realty

  610 Tunxis Hill Rd Unit 2, Fairfield, CT 06825
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  $1,560,000 Sold Jul 21, 2025

  157 North Ave, Westport, CT 06880

  • 4 Beds
  • 2.5 Baths
  • 2,641 Sq Ft
  • Built 1961

  Last Sold Summary

  • 5% Below List Price
  • $591/SF
  • 12 Days On Market

  Current Estimated Value $1,555,736

  Last Listing Agent Judy Michaelis Coldwell Banker Realty

  157 North Ave, Westport, CT 06880
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  Est $2,711,258 Not Listed For Sale

  64 Long Lots Rd, Westport, CT 06880

  • 5 Beds
  • 6 Baths
  • 3,970 Sq Ft
  • Built 1956

  64 Long Lots Rd, Westport, CT 06880

  Last Sold Summary

  • 4% Above List Price
  • $655/SF
  • 22 Days On Market

  Last Sold Price $2,600,000

  Last Listing Agent Bobbie Poeltl Abagnale William Pitt
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  /19

  $5,499,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 7,000 Sq Ft

  36 Maple Ave S, Westport, CT 06880

  This is an exceptional opportunity to collaborate from the early design phase to create your "Dream House" with Redcoat Homes, nestled in the picturesque Greens Farms neighborhood. This five/six-bedroom residence is set on a level .70-acre lot, embodying a perfect synergy of architectural excellence and an enviable location. Crafted for modern living by the esteemed architect Judith Larson, this

  Kelly Loucas Compass Connecticut, LLC

  36 Maple Ave S, Westport, CT 06880
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  $2,675 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,288 Sq Ft
  • Apartment for Rent

  53 Nordstrand Ave, Fairfield, CT 06825

  Welcome to this bright and spacious first-floor two-bedroom apartment located at 53 Nordstrand Ave, Fairfield, CT. This well-maintained unit offers a comfortable and functional layout featuring a living room and separate dining room, hardwood floors, and abundant natural light throughout. Situated in the Tunxis Hill / North Fairfield neighborhood, this apartment is located in a well-established

  amaryllis rodriguez RE/MAX Right Choice

  53 Nordstrand Ave, Fairfield, CT 06825
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  $705,000 Sold Aug 29, 2025

  73 Alden St, Fairfield, CT 06824

  • 2 Beds
  • 1 Bath
  • 1,104 Sq Ft
  • Built 1954

  Last Sold Summary

  • $639/SF
  • 30 Days On Market

  Current Estimated Value $736,370

  Last Listing Agent Tom Fitzpatrick Coldwell Banker Realty

  73 Alden St, Fairfield, CT 06824
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  Est $1,672,462 Not Listed For Sale

  14 North Ave, Westport, CT 06880

  • 4 Beds
  • 2.5 Baths
  • 3,280 Sq Ft
  • Built 1975

  14 North Ave, Westport, CT 06880

  Last Sold Summary

  • 17% Above List Price
  • $434/SF
  • 46 Days On Market

  Last Sold Price $1,425,000

  Last Listing Agent Georgia Wasserman Coldwell Banker Realty
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  $132,500

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  78 Rowsley St Unit 4, Bridgeport, CT 06605

  Tucked into the heart of Bridgeport's lively Black Rock section, this charming one bedroom co-op offers a cozy layout with a kitchen, living room and an enclosed private porch.This home has great bones and is ready for your own personal touches to make it truly shine. Set within a fun, welcoming location near shops, restaurants and the Shoreline by St. Mary's by the Sea, this is a wonderful

  Sandy Petrino William Pitt Sotheby's Int'l

  78 Rowsley St Unit 4, Bridgeport, CT 06605
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  $2,150 total monthly price

  • 2 Beds
  • 1 Bath
  • 4,432 Sq Ft
  • Apartment for Rent

  175 Wilson St Unit 179, Bridgeport, CT 06605

  Discover this charming and inviting 2-bedroom, 1-bath home located in the heart of Black Rock - one of the most desirable and sought-after neighborhoods in Fairfield County. Filled with character and natural light, this home features gleaming hardwood floors, a spacious and functional kitchen perfect for cooking and gathering, and a cozy living area that feels warm and welcoming the moment you

  Matt Ramos ASJ Realty Partners

  175 Wilson St Unit 179, Bridgeport, CT 06605
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  $6,649,000 Sold Nov 21, 2025

  7 Roshab Ln, Westport, CT 06880

  • 6 Beds
  • 7.5 Baths
  • 8,215 Sq Ft
  • Built 2025

  Last Sold Summary

  • $809/SF
  • 44 Days On Market

  Current Estimated Value $6,643,540

  Last Listing Agent Totney Benson Coldwell Banker Realty

  7 Roshab Ln, Westport, CT 06880
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  Est $3,303,954 Not Listed For Sale

  12 Hockanum Rd, Westport, CT 06880

  • 5 Beds
  • 5.5 Baths
  • 8,238 Sq Ft
  • Built 1962

  12 Hockanum Rd, Westport, CT 06880

  Last Sold Summary

  • 10% Above List Price
  • $364/SF
  • 31 Days On Market

  Last Sold Price $3,000,000

  Last Listing Agent Susan Vanech Compass Connecticut, LLC
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  $1,419,000

  • 4 Beds
  • 2.5 Baths
  • 3,597 Sq Ft

  153 Pease Ave, Southport, CT 06890

  Newly Renovated Colonial in Prime Southport Location. Beautifully updated colonial offering modern comfort and timeless style. Featuring a stunning new custom kitchen with a large center island, professional Thermador appliances, and separate butlers pantry, this home is perfect for both everyday living and entertaining. The open floor plan is filled with natural light and has 9ft ceilings

  Basil Amso RE/MAX Right Choice

  153 Pease Ave, Southport, CT 06890
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  $3,000 total monthly price

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

  131 Beach Rd Unit 202, Fairfield, CT 06824

  BRAND NEW: NOW LEASING @ 131BEACH! This pristine, newly constructed 1BR + Den/Office apartment offers an open floorplan with chef's kitchen featuring quartz counters, stainless appliances, and center island overlooking living/dining areas, as well as a spacious ensuite Primary Bedroom and Full Bath. Amenities include elevator, secure keyless entry, laundry in-unit, reserved parking, EV charging

  Kaitlyn Walsh William Raveis Real Estate

  131 Beach Rd Unit 202, Fairfield, CT 06824
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  $250,000 Sold Oct 08, 2025

  65 Ellsworth St Unit 315, Bridgeport, CT 06605

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Built 1987

  Last Sold Summary

  • 16% Above List Price
  • $357/SF
  • 11 Days On Market

  Current Estimated Value $243,510

  Last Listing Agent Chris Balestriere William Raveis Real Estate

  65 Ellsworth St Unit 315, Bridgeport, CT 06605
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  Est $1,412,417 Not Listed For Sale

  16 Wakenor Rd, Westport, CT 06880

  • 3 Beds
  • 3 Baths
  • 2,083 Sq Ft
  • Built 1943

  16 Wakenor Rd, Westport, CT 06880

  Last Sold Summary

  • 9% Above List Price
  • $624/SF
  • 21 Days On Market

  Last Sold Price $1,300,000

  Last Listing Agent Meredith Cohen Serhant Connecticut, LLC

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