Southport, CT Homes

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  $595,000 Under Contract

  • 5 Beds
  • 3 Baths
  • 3,293 Sq Ft

  22 Monroe St Unit 24, Bridgeport, CT 06605

  Exceptional Black Rock Multi-Family - Timeless Character & Rare Value Nestled in the heart of the highly coveted Black Rock neighborhood, this impressive 3-unit multi-family residence with a 2-car garage blends classic architectural elegance with modern functionality. Each unit is highlighted by hardwood floors, stately columns(2nd floor), high ceilings, and generously proportioned living and

  Stacy Pfannkuch Century 21 AllPoints Realty

  22 Monroe St Unit 24, Bridgeport, CT 06605
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  $3,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  937 Post Rd Unit 2A, Fairfield, CT 06824

  Available for May 1 occupancy! Images are of Unit 3A, which is fully finished, not this unit! Finishes will be the same. Welcome to luxury condo living in the heart of Fairfield's downtown scene, walking distance to many amenities and in close proximity to the highway! This elevator building has been completely renovated with four gorgeous condos and main common areas (to be fully completed April

  Andrea Viscuso Compass Connecticut, LLC

  937 Post Rd Unit 2A, Fairfield, CT 06824
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  $185,000 Sold Dec 26, 2025

  26 Rowsley St Unit 3, Bridgeport, CT 06605

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Built 1918

  Last Sold Summary

  • $218/SF
  • 113 Days On Market

  Last Listing Agent Jennifer Wilson Berkshire Hathaway NE Prop.

  26 Rowsley St Unit 3, Bridgeport, CT 06605
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  Est $2,935,013 Not Listed For Sale

  8 Sandhopper Trail, Westport, CT 06880

  • 4 Beds
  • 2.5 Baths
  • 5,055 Sq Ft
  • Built 2006

  8 Sandhopper Trail, Westport, CT 06880

  Last Sold Summary

  • 25% Above List Price
  • $465/SF
  • 23 Days On Market

  Last Sold Price $2,350,000

  Last Listing Agent Judy Michaelis Coldwell Banker Realty
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  /10

  $740,000 Pending

  • 18 Beds
  • 6 Baths
  • 7,416 Sq Ft

  899 Hancock Ave, Bridgeport, CT 06605

  RARE 6 FAMILY. 3 BEDROOMS EACH UNIT. POSSIBLE GOOD INCOME PRODUCING PROPERTY. PERFECT FOR REHAB OR FLIP. LARGE REAR YARD. REHAB LOAN OR CASH PREFERRED. SUBJECT TO PROBATE COURT APPROVAL. SUBJECT TO RESERVED PROSPECT.

  Charles Scott Tri-State Realty

  899 Hancock Ave, Bridgeport, CT 06605
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  $3,125 total monthly price

  • 2 Beds
  • 1 Bath
  • 931 Sq Ft
  • Condo for Rent

  91 Saugatuck Ave Unit 4, Westport, CT 06880

  2 Bedroom - Great Kitchen, bathroom and Location. Spacious rear outdoor deck. Immediate to downtown Saugatuck area. 3 min walk to the Westport Train Station. Convenient to shopping, restaurants and amenities - all in walking distance. Newly Renovated. Rustic Wood flooring. New Stainless Steel appliances. HE Washer/Dryer/dishwasher. Bright, comfortable, spacious, clean and new. 1st floor, easy

  91 Saugatuck Ave Unit 4, Westport, CT 06880
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  $2,645,000 Sold Feb 17, 2026

  11 Old Hill Rd, Westport, CT 06880

  • 4 Beds
  • 4.5 Baths
  • 3,935 Sq Ft
  • Built 1928

  Last Sold Summary

  • 5% Above List Price
  • $672/SF
  • 16 Days On Market

  Current Estimated Value $2,522,388

  Last Listing Agent Susan Lieberman The Riverside Realty Group

  11 Old Hill Rd, Westport, CT 06880
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  Est $3,137,243 Not Listed For Sale

  9 Wheeler Gate, Westport, CT 06880

  • 5 Beds
  • 5 Baths
  • 3,770 Sq Ft
  • Built 1994

  9 Wheeler Gate, Westport, CT 06880

  Last Sold Summary

  • 4% Above List Price
  • $798/SF
  • 6 Days On Market

  Last Sold Price $3,010,000

  Last Listing Agent Judy Michaelis Coldwell Banker Realty
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  $5,926,000 Under Contract

  • 7 Beds
  • 9 Baths
  • 7,806 Sq Ft

  25 Ellery Ln, Westport, CT 06880

  Work is underway at 25 Ellery! Have you been quietly creating a wishlist of EVERYTHING you want in your next home? This new mini-estate on a preferred Greens Farms cul-de-sac is YOUR EVERYTHING! There will be no reason to leave home - 25 Ellery offers it all including a pool with spa and auto cover. The flow of this house is divine. Rooms are spacious, comfortable, and well-thought out for

  Jaclyn Picarillo Higgins Group Bedford Square

  25 Ellery Ln, Westport, CT 06880
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  $2,950 total monthly price

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

  245 Unquowa Rd Unit 59, Fairfield, CT 06824

  Welcome to Mosswood! Move into this beautifully updated first floor condo offering a perfect blend of comfort, style and convenience. Featuring 2 spacious bedrooms and 1 full bath, new kitchen, gleaming hardwood floors, fresh paint throughout. Enjoy bright open layout w. large Livingroom and dining room. Unit includes generous storage with walk-in closet, second bedroom with oversized closet, a

  Doug Munson Munson Real Estate

  245 Unquowa Rd Unit 59, Fairfield, CT 06824
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  $1,450,000 Sold Sep 12, 2025

  60 Walbin Ct, Fairfield, CT 06824

  • 4 Beds
  • 3.5 Baths
  • 3,497 Sq Ft
  • Built 1997

  Last Sold Summary

  • $415/SF
  • 33 Days On Market

  Current Estimated Value $1,497,298

  Last Listing Agent Chrissie Rodriguez Higgins Group Real Estate

  60 Walbin Ct, Fairfield, CT 06824
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  Est $3,401,712 Not Listed For Sale

  28 Flower Farm Cir, Westport, CT 06880

  • 5 Beds
  • 5.5 Baths
  • 5,058 Sq Ft
  • Built 1995

  28 Flower Farm Cir, Westport, CT 06880

  Last Sold Summary

  • 5% Above List Price
  • $643/SF
  • 12 Days On Market

  Last Sold Price $3,250,000

  Last Listing Agent Alex Chingas Coldwell Banker Realty
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  /17

  $1,075,000

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  483 Main St, Westport, CT 06880

  Located just minutes from trendy downtown Westport, this inviting split-level home combines comfort and convenience. Set on over a quarter acre of level, fenced-in property, it offers plenty of space for outdoor enjoyment. Step inside to a bright and welcoming living room featuring an oversized picture window, hardwood floors, and a wood-burning fireplace. The formal dining room opens to a

  Jodi Gutierrez Alliance R.E. Consultants

  483 Main St, Westport, CT 06880
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  /10

  $3,900 total monthly price

  • 4 Beds
  • 1.5 Baths
  • 1,300 Sq Ft
  • Condo for Rent

  294 Berkeley Rd Unit 294 Berkeley Road, Fairfield, CT 06825

  This property is an amazing 4 bedroom 1.5 bathroom apartment with all new appliances and vinyl flooring. It is 900 square foot with plenty of room. Ideal for families. Furthermore, there is ALDI, Planet Fitness, Subway, Dunkin Donuts, and Stop & Shop all within walking distance. This rental is available starting September 1, 2025.

  294 Berkeley Rd Unit 294 Berkeley Road, Fairfield, CT 06825
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  $899,000 Sold Nov 10, 2025

  153 Longview Ave, Fairfield, CT 06824

  • 4 Beds
  • 3 Baths
  • 2,912 Sq Ft
  • Built 1920

  Last Sold Summary

  • $309/SF
  • 48 Days On Market

  Current Estimated Value $854,632

  Last Listing Agent Christine Ricci Keller Williams NY Realty

  153 Longview Ave, Fairfield, CT 06824
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  Est $2,575,581 Not Listed For Sale

  26 Flower Farm Cir, Westport, CT 06880

  • 5 Beds
  • 5 Baths
  • 4,230 Sq Ft
  • Built 1996

  26 Flower Farm Cir, Westport, CT 06880

  Last Sold Summary

  • 7% Above List Price
  • $567/SF
  • 15 Days On Market

  Last Sold Price $2,400,000

  Last Listing Agent Karen Scott Compass Connecticut, LLC
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  $1,749,999

  • 16 Beds
  • 8 Baths
  • 5,824 Sq Ft

  25 Whittier St, Bridge Port, CT 06605

  Exceptional investment opportunity in Bridgeport's desirable Black Rock neighborhood. This 8-unit multifamily property features eight 2-bedroom, 1-bathroom units, each with spacious layouts ideal for tenants seeking comfort and convenience. The building is well-maintained, with separate utilities and strong rental history, making it a turnkey addition to any portfolio. Located just minutes from

  Zach Pinto Alpha Capital Realty, LLC

  25 Whittier St, Bridge Port, CT 06605
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  $3,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  937 Post Rd Unit 2B, Fairfield, CT 06824

  Available for May 1 occupancy! Images are of Unit 3A, which is fully finished, not this unit! Finished will be the same. Welcome to luxury condo living in the heart of Fairfield's downtown scene, walking distance to many amenities and in close proximity to the highway! This elevator building has been completely renovated with four gorgeous condos and main common areas (to be fully completed April

  Andrea Viscuso Compass Connecticut, LLC

  937 Post Rd Unit 2B, Fairfield, CT 06824
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  $1,210,000 Sold Oct 15, 2025

  14 Dill Rd, Fairfield, CT 06824

  • 3 Beds
  • 2.5 Baths
  • 2,659 Sq Ft
  • Built 1947

  Last Sold Summary

  • 3% Above List Price
  • $455/SF
  • 23 Days On Market

  Current Estimated Value $1,202,570

  Last Listing Agent Carrie Sakey Coldwell Banker Realty

  14 Dill Rd, Fairfield, CT 06824
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  Est $3,204,450 Not Listed For Sale

  269 Sturges Hwy, Westport, CT 06880

  • 5 Beds
  • 7 Baths
  • 5,009 Sq Ft
  • Built 1997

  269 Sturges Hwy, Westport, CT 06880

  Last Sold Summary

  • 7% Above List Price
  • $599/SF
  • 67 Days On Market

  Last Sold Price $3,000,000

  Last Listing Agent Susan Vanech Compass Connecticut, LLC
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  $525,000 Pending

  • 5 Beds
  • 3 Baths
  • 2,437 Sq Ft

  109 Wordin Ave Unit 111, Bridgeport, CT 06605

  Well-maintained two-family property with an additional upper-level unit located at 109-111 Wordin Ave, Bridgeport, CT 06605. The first-floor unit features 2 bedrooms, 1 full bath, an updated kitchen, and in-unit laundry. The second-floor unit offers 2 bedrooms, 1 full bath, and an updated kitchen with granite countertops. The third-floor unit includes 1 bedroom, a kitchenette, and a full

  Diane Rankine Berkshire Hathaway NE Prop.

  109 Wordin Ave Unit 111, Bridgeport, CT 06605
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  /15

  $4,800 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,342 Sq Ft
  • House for Rent

  63 Valley Rd, Westport, CT 06880

  Welcome home to this adorable 2-3 bedroom, 2 full bath cape on Valley Rd., a super convenient, quiet neighborhood located between Greens Farms and Saugatuck Village. The sunny first floor features a spacious living room with fireplace, family/dining room with windows overlooking the backyard and access to the patio. The bright, spacious kitchen, full bath, bedroom/office, and laundry complete the

  Georgia Rojas Coldwell Banker Realty

  63 Valley Rd, Westport, CT 06880
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  $1,600,000 Sold Mar 02, 2026

  105 Charter Oak Rd, Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 3,900 Sq Ft
  • Built 1975

  Last Sold Summary

  • 7% Above List Price
  • $410/SF
  • 138 Days On Market

  Current Estimated Value $1,500,287

  Last Listing Agent Julie Vanderblue Higgins Group Real Estate

  105 Charter Oak Rd, Fairfield, CT 06824
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  Not Listed For Sale

  8 Cunningham Place, Westport, CT 06880

  • 2 Beds
  • 3 Baths
  • 1,614 Sq Ft
  • Built 1924

  8 Cunningham Place, Westport, CT 06880

  Last Sold Summary

  • $589/SF
  • 11 Days On Market

  Last Sold Price $950,000

  Last Listing Agent Linda Dunsmore Coldwell Banker Realty
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  $6,999,999 Pending

  • 6 Beds
  • 6.5 Baths
  • 8,400 Sq Ft

  3 Tanglewood Ln, Westport, CT 06880

  Introducing an exceptional new construction home by Redcoat Homes. Spanning over 8,000 square feet, this stunning property is situated on a flat, one-plus acre lot in the desirable Old Hill neighborhood of Westport. The location is private yet conveniently close to I-95 and the Merritt Parkway, just minutes from the beach and town. It also borders Earth Place, one of the top family-friendly

  James Lanzaro Compass Connecticut, LLC

  3 Tanglewood Ln, Westport, CT 06880
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  $2,450 total monthly price

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

  100 Silliman St Unit 1, Fairfield, CT 06824

  Move right into this bright and inviting 2 bedroom, 1 bath ranch style condo with HEAT and HOT WATER included in the rent. The spacious living room is filled with natural light and flows seamlessly into a dining area, perfect for everyday living or entertaining. The kitchen also offers abundant natural light and ample counter space, making meal prep both easy and enjoyable. Both bedrooms are

  Chrissie Rodriguez Higgins Group Real Estate

  100 Silliman St Unit 1, Fairfield, CT 06824
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  $3,250,000 Sold Jun 06, 2025

  27 Old Hill Farms Rd, Westport, CT 06880

  • 5 Beds
  • 3.5 Baths
  • 4,298 Sq Ft
  • Built 1931

  Last Sold Summary

  • 8% Above List Price
  • $756/SF
  • 8 Days On Market

  Current Estimated Value $3,150,984

  Last Listing Agent Debra Grant Show to Sell Homes, LLC

  27 Old Hill Farms Rd, Westport, CT 06880
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  Est $2,449,850 Not Listed For Sale

  3 Maple Ln, Westport, CT 06880

  • 5 Beds
  • 5.5 Baths
  • 5,268 Sq Ft
  • Built 1986

  3 Maple Ln, Westport, CT 06880

  Last Sold Summary

  • 24% Above List Price
  • $375/SF
  • 16 Days On Market

  Last Sold Price $1,975,000

  Last Listing Agent Michael Lissack The Virtual Realty Group
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  /35

  $3,295,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,200 Sq Ft

  26 Treadwell Ave, Westport, CT 06880

  26 Treadwell Avenue is where historic charm meets a modern edgy vibe. Reimagined from the ground up in 2025 by Michael Greenberg, this 1894 Victorian Farmhouse has been transformed into a statement of refined design and craftsmanship. Notable features include exposed beams, white oak floors that ground the space, and curated architectural finishes that make every room feel intentional. Set on a

  Kim Harizman Compass Connecticut, LLC

  26 Treadwell Ave, Westport, CT 06880
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  /11

  $2,400 total monthly price

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

  77 Crestwood Rd, Fairfield, CT 06824

  Location Location Location! Cozy 2 bedroom, 1st floor apartment, nice clean kitchen, washer & dryer in basement, large park-like yard. Across the street from Pickleball, Tennis Court and Playing Fields of Gould Manor Park. A true find. NO PETS! Excellent Credit and References Required.

  Toby Ketcham Lane William Raveis Real Estate

  77 Crestwood Rd, Fairfield, CT 06824
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  $790,000 Sold Sep 03, 2025

  84 Edison Ave, Fairfield, CT 06825

  • 4 Beds
  • 2.5 Baths
  • 1,904 Sq Ft
  • Built 1998

  Last Sold Summary

  • $415/SF
  • 27 Days On Market

  Current Estimated Value $788,501

  Last Listing Agent Denise Curcio William Raveis Real Estate

  84 Edison Ave, Fairfield, CT 06825
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  Est $767,464 Not Listed For Sale

  230 Saugatuck Ave Unit 20, Westport, CT 06880

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

  230 Saugatuck Ave Unit 20, Westport, CT 06880

  Last Sold Summary

  • 5% Above List Price
  • $608/SF
  • 125 Days On Market

  Last Sold Price $730,000

  Last Listing Agent Mary Kate Klemish-Boehm Brown Harris Stevens
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  /40

  $2,575,000

  • 6 Beds
  • 4.5 Baths
  • 5,083 Sq Ft

  4 the Fenway, Westport, CT 06880

  Timeless elegance in Westport's renowned Old Hill. Set on 2.22 bucolic acres w/a heated Gunite pool & picturesque pond, this expansive 5-6 bedroom,4.5 bath farmhouse blends classic charm w/thoughtful recent enhancements that delivers a renewed sense of style & energy to the home. A renovated kitchen remains the heart of the home, featuring a generous center island & a stunning, glass-walled

  Mary Kate Klemish-Boehm Brown Harris Stevens

  4 the Fenway, Westport, CT 06880
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  /11

  $1,800 total monthly price

  • 2 Beds
  • 1 Bath
  • 3,350 Sq Ft
  • House for Rent

  2449 North Ave Unit 3, Bridgeport, CT 06604

  Spacious and light-filled 2-bedroom rental located in a well-maintained multi-family home. This large unit features high ceilings that create an open, airy feel throughout. Enjoy comfortable living in a convenient location close to shopping, dining, and everyday amenities. A great opportunity for those seeking space, charm, and easy access to everything you need.

  Bobbie Poeltl Abagnale William Pitt Sotheby's Int'l

  2449 North Ave Unit 3, Bridgeport, CT 06604
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  $546,000 Sold Oct 27, 2025

  299 Marlborough Terrace, Fairfield, CT 06825

  • 2 Beds
  • 1.5 Baths
  • 1,268 Sq Ft
  • Built 1947

  Last Sold Summary

  • $431/SF
  • 60 Days On Market

  Current Estimated Value $540,668

  Last Listing Agent Deborah Merlino William Raveis Real Estate

  299 Marlborough Terrace, Fairfield, CT 06825
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  Est $753,122 Not Listed For Sale

  230 Saugatuck Ave Unit 8, Westport, CT 06880

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

  230 Saugatuck Ave Unit 8, Westport, CT 06880

  Last Sold Summary

  • $629/SF
  • 32 Days On Market

  Last Sold Price $755,000

  Last Listing Agent Scott Wright RE/MAX
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  $5,000,000 Pending

  • 6 Beds
  • 9 Baths
  • 8,545 Sq Ft

  125 Old Rd, Westport, CT 06880

  Experience the elevated ease of modern luxury in this brand new SIGNATURE Home by SIR Development, Westport's most respected ground-up RE developer with 30+ years & 300+ completed homes. Set on a scenic park-like acre w/ gunite pool & circular drive, conveniently located within walking distance of Long Lots School & shops, just 1.7 mi to train. Experience the grandeur of the soaring two story

  Doug Bross Coldwell Banker Realty

  125 Old Rd, Westport, CT 06880
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  /12

  $2,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 3,350 Sq Ft
  • House for Rent

  2449 North Ave Unit 1, Bridgeport, CT 06604

  Spacious and light-filled 2-bedroom rental located in a well-maintained multi-family home. This large unit features high ceilings that create an open, airy feel throughout. Enjoy comfortable living in a convenient location close to shopping, dining, and everyday amenities. A great opportunity for those seeking space, charm, and easy access to everything you need.

  Bobbie Poeltl Abagnale William Pitt Sotheby's Int'l

  2449 North Ave Unit 1, Bridgeport, CT 06604
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  $11,000,000 Sold Mar 02, 2026

  39 Compo Pkwy, Westport, CT 06880

  • 6 Beds
  • 9 Baths
  • 11,150 Sq Ft
  • Built 2017

  Last Sold Summary

  • 15% Below List Price
  • $987/SF
  • 33 Days On Market

  Current Estimated Value $7,435,524

  Last Listing Agent Michelle Genovesi William Raveis Real Estate

  39 Compo Pkwy, Westport, CT 06880
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  Est $785,819 Not Listed For Sale

  230 Saugatuck Ave Unit 7, Westport, CT 06880

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

  230 Saugatuck Ave Unit 7, Westport, CT 06880

  Last Sold Summary

  • 4% Above List Price
  • $632/SF
  • 39 Days On Market

  Last Sold Price $759,000

  Last Listing Agent Cindy Saul Coldwell Banker Realty

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