Fairfield, CT Homes

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  $2,649,000

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

  4 the Fenway, Westport, CT 06880

  Timeless elegance in Westport's prestigious Old Hill. First time on the market in 29 years! This expansive 5-6 bedroom, 4.5 bath farmhouse is gracefully set on 2.22 serene acres, featuring a heated gunite pool, picturesque pond, and a very rare blend of privacy and proximity to town. The sun-drenched primary suite is a true retreat with a fireplace, spa-like bath, and generous walk-in closet. A

  Mary Kate Klemish-Boehm Brown Harris Stevens

  4 the Fenway, Westport, CT 06880
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  Explore Old Hill

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  /12

  $2,350 per month

  • 1 - 2 Beds
  • 2 Baths
  • 750 Sq Ft
  • Condo for Rent

  170 Post Rd W, Westport, CT 06880

  Architect designed apartment with high ceilings, marvelous windows and wonderful light, 2 bedrooms with large room sized loft; Kitchen/Living Room and Dining Room combination;Hardwood floors; 1 bath, A/C with all appliances; close to downtown and all amenities in Westport has to offer. Minutes to I-95 or Merritt Parkway; residents have use of Longshore pools, golf and tennis for same fees as

  170 Post Rd W, Westport, CT 06880
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  $1,850,000 Sold Jul 14, 2025

  • 2,891 Sq Ft
  • $640/SF
  • 8 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1965

  52 Woodside Ave, Westport, CT 06880

  Enjoy a wonderful life on Woodside Avenue, one of Old Hill's most popular streets, walking distance to town & Earthplace Nature Centre. This charming ranch home offers sophisticated, easy living & so much more. The open floorplan radiates off the bright kitchen with stainless steel appliances, including a wine fridge & gorgeous granite countertops. The formal living room enjoys a wall of sliding

  Jessica Brookbanks Coldwell Banker Realty

  52 Woodside Ave, Westport, CT 06880
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  Est $2,590,932 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 4,330 Sq Ft

  2 Heron Lake Ln, Westport, CT 06880

  2 Heron Lake Ln, Westport, CT 06880
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  $2,895,000

  • 5 Beds
  • 4.5 Baths
  • 5,424 Sq Ft

  20 Crawford Rd, Westport, CT 06880

  Nestled in Westport's coveted Old Hill neighborhood, this stunning residence blends classic Colonial design w/modern amenities. You're greeted by the centerpiece of the home - an impressive foyer w/soaring ceilings. The spacious office w/lacquer-finished built-ins includes a fireplace and access to the veranda. For more intimate gatherings, go through the French doors to a sitting room,

  Lisa Tortora Coldwell Banker Realty

  20 Crawford Rd, Westport, CT 06880
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  $8,500 per month

  • 5 Beds
  • 4.5 Baths
  • 3,086 Sq Ft
  • House for Rent

  259 Wilton Rd, Westport, CT 06880

  Discover a spacious and flexible Westport ranch on nearly 2 private acres. Offered furnished or unfurnished for an easy move. The home features 5 bedrooms and 4 full baths. The main level includes 4 bedrooms, 3 baths, and an updated kitchen. The finished walkout lower level adds about 1,000 square feet and includes a separate apartment with a full kitchen, a bathroom, its own laundry, and a

  Inna Agujen Coldwell Banker Realty

  259 Wilton Rd, Westport, CT 06880
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  $2,225,000 Sold Jul 07, 2025

  • 3,585 Sq Ft
  • $621/SF
  • 23 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1993

  75 Old Hill Rd, Westport, CT 06880

  Stunning colonial with contemporary flair set on a private acre in much sought after Old Hill. Convenient to town, train and beach. This is not your cookie cutter colonial with wonderful, flexible, open floor plan and top of the line remodeled kitchen. Current piano room could be formal dining room or office/study. Impressive Primary Bedroom suite with beautiful bath. Large upstairs room with

  Regina Kendig William Raveis Real Estate

  75 Old Hill Rd, Westport, CT 06880
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  Est $4,501,474 Not Listed For Sale

  • 6 Beds
  • 9 Baths
  • 7,552 Sq Ft

  10 Cranbury Rd, Westport, CT 06880

  10 Cranbury Rd, Westport, CT 06880
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  $2,799,999 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,683 Sq Ft

  9 Woodside Ln, Westport, CT 06880

  Welcome to this charming Colonial home in the desirable Old Hill neighborhood of Westport, CT. This 3,683 sq ft residence on a generous 0.95-acre lot blends classic character with modern convenience. The open layout connects living areas to the outdoors, creating an inviting space for relaxation and entertaining. The home boasts attractive exterior accents while maximizing space and inviting

  Judy Michaelis Coldwell Banker Realty

  9 Woodside Ln, Westport, CT 06880
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  /12

  $3,500 per month

  • 1 - 2 Beds
  • 2 Baths
  • 750 Sq Ft
  • Condo for Rent

  170 Post Rd W, Westport, CT 06880

  Architect designed apartment with high ceilings, marvelous windows and wonderful light, 2 bedrooms with large room sized loft; Kitchen/Living Room and Dining Room combination;Hardwood floors; 1 bath, A/C with all appliances; close to downtown and all amenities in Westport has to offer. Minutes to I-95 or Merritt Parkway; residents have use of Longshore pools, golf and tennis for same fees as

  170 Post Rd W, Westport, CT 06880
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  $450,500 Sold Jun 27, 2025

  • 1,200 Sq Ft
  • $375/SF
  • 5 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1973

  30 Hills Ln Unit 30, Westport, CT 06880

  Welcome home to Birchwood! This beautifully maintained community offers a tranquil escape from city life. Tucked away, yet minutes to all Norwalk/Westport attractions. Here you will find meticulous landscaping, community club house and an in-ground pool, setting the stage for a super summer retreat. This wonderful 2 bedrooms, 1.5 bath condo offers a rare two car garage with two storage bay areas,

  Aurelia Gilbert Coldwell Banker Realty

  30 Hills Ln Unit 30, Westport, CT 06880
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  Est $1,296,897 Not Listed For Sale

  • 2 Beds
  • 4 Baths
  • 2,992 Sq Ft

  5 Terra Nova Cir, Westport, CT 06880

  5 Terra Nova Cir, Westport, CT 06880
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  $2,499,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,495 Sq Ft

  19 Old Hill Rd, Westport, CT 06880

  Step into a home where every detail tells a story of timeless elegance and masterful transformation. This 4-bedroom, 3-bath Colonial-reimagined through a multi-year, designer-led renovation-seamlessly marries historic charm with modern sophistication. Original Southern Pine floors and exposed beams ground the home in authenticity, while a stunning new kitchen by Shore & Country elevates everyday

  Cindy Raney Coldwell Banker Realty

  19 Old Hill Rd, Westport, CT 06880
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  $12,000 per month

  • 4 Beds
  • 5 Baths
  • 3,658 Sq Ft
  • House for Rent

  53 Sylvan Rd N, Westport, CT 06880

  Nestled on 1.36 picturesque acres in Old Hill, this renovated antique home is brimming with character and modern comforts. Just moments from town, Post Road, and schools, the enchanting professional landscaped grounds feature specimen and fruit trees, a built-in BBQ and fireplace, and a wisteria-draped pergola over a stone patio. A charming barn offers additional storage or creative use. Inside,

  Erica Acheychek Coldwell Banker Realty

  53 Sylvan Rd N, Westport, CT 06880
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  $6,250,000 Sold Jun 20, 2025

  • 7,595 Sq Ft
  • $823/SF
  • 2 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2012

  19 Old Hill Farms Rd, Westport, CT 06880

  Better than new! This impeccably designed home, built by Coastal Home Builders, is nestled on a coveted street in the desirable Old Hill section of Westport. Recent upgrades have further enhanced this already exceptional property. From the moment you enter the grand foyer, you'll be greeted by luxurious interiors and a seamless floor plan ideal for both everyday living and entertaining. French

  Jennifer Leahy Compass Connecticut, LLC

  19 Old Hill Farms Rd, Westport, CT 06880
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  Est $1,672,917 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,992 Sq Ft

  17 Terra Nova Cir, Westport, CT 06880

  17 Terra Nova Cir, Westport, CT 06880
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  /3

  $3,030,000 Open Sat 12PM - 3PM

  • 5 Beds
  • 5.5 Baths
  • 5,916 Sq Ft

  20 Old Hill Rd, Westport, CT 06880

  Welcome to this beautifully maintained 1945 stone-front Cape in the heart of Old Hill. Loved by the same family for 22 years, it radiates warmth and character. With 5 bedrooms, 5.5 baths, and two flexible spaces for home offices, it offers comfort and versatility, including a first-floor suite ideal for guests or in-laws. The light-filled kitchen flows into an inviting dining area and cozy sunken

  Michelle Genovesi William Raveis Real Estate

  20 Old Hill Rd, Westport, CT 06880
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  $6,250 per month

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  5 Edge Hill Trail, Westport, CT 06880

  BRAND NEW ROOF. BRAND NEW BOILER. NEW CENTRAL AC (coming soon). Even though the house is not new, it sure will seem like it is! But that isn't the best part about this house...this lovely home is in a catbird seat location! Walking distance to the best Westport has to offer...Main Street shops & restaurants, the library, the Levitt Pavilion, the farmers' market or the Playhouse. A quick bike ride

  Susan Herrmann William Raveis Real Estate

  5 Edge Hill Trail, Westport, CT 06880
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  $2,290,000 Sold Jun 17, 2025

  • 4,000 Sq Ft
  • $572/SF
  • 13 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2020

  10 Heathwood Ln, Westport, CT 06880

  Nestled on a private street in the sought-after Old Hill neighborhood, this contemporary/colonial style home provides the perfect blend of picturesque tranquility and convenience. The home is in pristine condition and is tastefully decorated featuring modern finishes, designer lighting and an overall inviting ambiance. Sunshine flows through the energy-efficient glass windows as you feel the

  Lauren Turner Corcoran Centric Realty

  10 Heathwood Ln, Westport, CT 06880
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  Est $3,069,657 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 4,560 Sq Ft

  14 Marion Rd, Westport, CT 06880

  14 Marion Rd, Westport, CT 06880
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  $3,750,000 Under Contract

  • 5 Beds
  • 7 Baths
  • 6,406 Sq Ft

  12 Old Hill Farms Rd, Westport, CT 06880

  Beautifully renovated vintage home offers timeless character on a professionally landscaped acre in coveted Old Hill. With 5 bedrooms, 5 full and 2 half baths with generous space and classic charm. The formal living room and elegant library both with fireplaces and hardwood floors create a warm and welcoming space for relaxing and entertaining. A spacious kitchen featuring a large center island,

  Emily Gordon Coldwell Banker Realty

  12 Old Hill Farms Rd, Westport, CT 06880
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  /18

  $3,500 per month

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

  170 B2 Post Rd W Unit B2, Westport, CT 06883

  2nd floor unit in free standing building. Open floor plan, soaring ceilings + a loft. Conveniently located ...walk to town and Westport's fantastic shops & restaurants.

  Sandra Calise Cenatiempo Settlers & Traders

  170 B2 Post Rd W Unit B2, Westport, CT 06883
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  $1,068,900 Sold Jun 16, 2025

  • 2,030 Sq Ft
  • $527/SF
  • 18 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1969

  97 Partrick Rd, Westport, CT 06880

  HIGHEST & BEST by SUNDAY APRIL 13th at 5:00 pm. Find your private Shangri-La, with in-ground pool, set back from the road on 1.35 acres in prestigious Old Hill. The custom Split was built by the original owners and is on the market for the first time. Entering from the front porch you are greeted by the welcoming entry hall with slate floor. Hand-pegged wide Antique hardwood floors are found in

  Mindy Wolkstein William Raveis Real Estate

  97 Partrick Rd, Westport, CT 06880
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  Est $3,053,196 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,424 Sq Ft

  5 Windrush Ln, Westport, CT 06880

  5 Windrush Ln, Westport, CT 06880
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  $2,949,000 Under Contract

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

  22 Marion Rd, Westport, CT 06880

  Set on picturesque property in a prime Old Hill-area location, this exceptional home offers space, amenities and convenience rarely seen. Approached from a circular driveway, this impressive home welcomes you from a front porch into an exquisite foyer with stunning carpentry and detailed wood flooring, which showcase the artistry of high-end home builder SIR Development. The generous layout

  Alex Chingas Coldwell Banker Realty

  22 Marion Rd, Westport, CT 06880
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  /20

  $2,350 per month

  • 1 Bed
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  170 Post Rd W Unit C2, Westport, CT 06880

  Bright, spacious apartment with cathedral ceiling, open kitchen, bedroom, bath. Laundry in unit. Great central location. Walk to town.

  Sandra Calise Cenatiempo Settlers & Traders

  170 Post Rd W Unit C2, Westport, CT 06880
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  $3,250,000 Sold Jun 06, 2025

  • 4,298 Sq Ft
  • $756/SF
  • 8 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1931

  27 Old Hill Farms Rd, Westport, CT 06880

  Classic "Old Hill Farms" Estate. One of a kind custom home completely renovated and restored to perfection. Showcase sun filled home with a marriage of old and new. Exceptional details, all custom millwork and cabinetry set on over one acre in premier Old Hill location. Gracious formal living room with custom built in window seat.Original wood burning fireplace complete this large gathering room

  Debra Grant Show to Sell Homes, LLC

  27 Old Hill Farms Rd, Westport, CT 06880
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  Est $2,490,617 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 5,637 Sq Ft

  3 Windrush Ln, Westport, CT 06880

  3 Windrush Ln, Westport, CT 06880
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  $499,999

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft

  13 Hills Ln, Westport, CT 06880

  Spacious open floor plan with hardwood floors. Light and bright overlooking beautifully landscaped grounds. Large open living/dinning area, eat-in kitchen. Two oversized bedrooms with lots of closet space. Two fully renovated baths. New appliances, first floor location. A private deck for summer entertaining, fireplace for cold winter nights. Secluded quiet location. Two additional on site

  Georgia Kornutik Coldwell Banker Realty

  13 Hills Ln, Westport, CT 06880
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  /31

  $11,500 per month

  • 5 Beds
  • 4.5 Baths
  • 3,436 Sq Ft
  • House for Rent

  96 Kings Hwy N, Westport, CT 06880

  Enjoy a walk to downtown Westport from desirable Old Hill in this award-winning historic home. This beautifully updated home offers an abundance of space, a stylish aesthetic, and the convenience of being close to everything Westport! Designed for entertaining, this outstanding home offers a wonderful collection of spaces for both daily living and hosting guests. At the heart of the home is the

  Cyd Hamer William Pitt Sotheby's Int'l

  96 Kings Hwy N, Westport, CT 06880
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  $955,000 Sold Apr 18, 2025

  • 2,065 Sq Ft
  • $462/SF
  • 54 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1886

  115 Wilton Rd, Westport, CT 06880

  RARE OPPORTUNITY to own in Westport with income to support your family. This multi-family home is just across the street from scenic Saugatuck River and convenient to Westport center. Remodeled features include updated kitchens, bathrooms, windows, mechanicals & more. UNIT #1 is on 1st floor: Living Rm, Eat-in Kitchen, 2 Bedrooms, Full Bathroom with laundry, Screened Porch. UNIT #2: 2nd floor:

  Lynn Fraund William Pitt Sotheby's Int'l

  115 Wilton Rd, Westport, CT 06880
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  Est $4,956,336 Not Listed For Sale

  • 6 Beds
  • 8 Baths
  • 8,957 Sq Ft

  6 Stonybrook Rd, Westport, CT 06880

  6 Stonybrook Rd, Westport, CT 06880
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  /29

  $1,600,000

  • 5 Beds
  • 2.5 Baths
  • 3,811 Sq Ft

  82 Partrick Rd, Westport, CT 06880

  Diamond in the Rough! This stately colonial is brimming with potential and ready to be restored to its former grandeur. Nestled on a private lot, the home offers a peaceful setting with ample space for everyone. Boasting over 3,800 sq ft, this spacious residence features 5 bedrooms and 2.5 bathrooms, along with gleaming hardwood floors and a variety of rooms designed for comfortable living. The

  Glenn Stavens Aspen Realty Group

  82 Partrick Rd, Westport, CT 06880
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  $3,450,000 Sold Apr 15, 2025

  • 6,789 Sq Ft
  • $508/SF
  • 4 Days On Market

  • 5 Beds
  • 6.5 Baths
  • Built 2002

  2 Twin Falls Ln, Westport, CT 06880

  A circular drive welcomes you as you approach this grand Center Hall Colonial, on 2 scenic acres with a fantastic Har-Tru tennis court, pool site & beautiful perennial gardens, sited on a quiet private lane in central Westport. Timeless elegance & quality construction is evident, from the moment you step into the impressive Entry Hall of this masterfully crafted home. Be delighted by the 10'

  Laurie Crouse Coldwell Banker Realty

  2 Twin Falls Ln, Westport, CT 06880
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  Est $2,243,366 Not Listed For Sale

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

  12 Overlook Rd, Westport, CT 06880

  12 Overlook Rd, Westport, CT 06880
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  /29

  $2,249,000

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

  10 Twin Falls Ln, Westport, CT 06880

  Beyond Beautiful - Welcome to 10 Twin Falls Lane, a striking property and home filled with natural light from floor-to-ceiling windows. Step into the sun-drenched foyer with terracotta tile. Throughout the years the home has been updated and modernized with soaring ceilings, serene views, and inspiring design. The expansive family room features a dramatic picture window and flows seamlessly into

  Kit Tingley Higgins Group Bedford Square

  10 Twin Falls Ln, Westport, CT 06880
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  $1,200,000 Sold Apr 14, 2025

  • 1,609 Sq Ft
  • $746/SF
  • 47 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  56 Partrick Rd, Westport, CT 06880

  Charming Ranch in Westport's coveted Old Hill neighborhood! Discover the potential in this classic 1966 ranch-style home, offering 3 bedrooms, 2 baths, and 1.67 acres of serene and dry private land. With great bones, this well-loved home presents a fantastic renovation opportunity to restore its mid-century appeal or customize it to fit your vision. The expansive lot also provides the perfect

  Mary Kate Klemish-Boehm Brown Harris Stevens

  56 Partrick Rd, Westport, CT 06880
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  Est $3,044,962 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 6,094 Sq Ft

  3 Indian Point Ln, Westport, CT 06880

  3 Indian Point Ln, Westport, CT 06880
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  /40

  $5,850,000

  • 6 Beds
  • 5.5 Baths
  • 6,588 Sq Ft

  17 River Ln, Westport, CT 06880

  This remarkable stone mansion, built in 1929, stands as one of the most historically and culturally significant residences in Westport and Fairfield County, celebrated as an exceptional trophy property. Meticulously restored and in impeccable, move-in ready condition, this home is poised for immediate enjoyment. Crafted in the esteemed tradition of Europe's grand Manor Houses, it boasts

  Alex Chingas Coldwell Banker Realty

  17 River Ln, Westport, CT 06880
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  $1,098,000 Sold Mar 31, 2025

  • 1,908 Sq Ft
  • $575/SF
  • 38 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  219 Wilton Rd, Westport, CT 06880

  Nestled in the heart of Westport this unique contemporary sits high on a 1-acre lot. Bright & airy w/high ceilings, multiple windows, French doors, and skylights this home is bathed in natural light. An inviting covered entrance w/large glass paneled doors welcomes you. From the entrance hall take the stairs to the heart-of-the-home, an open great-room w/hardwood flr, grand fireplace, vaulted

  Sandra Kinseley William Raveis Real Estate

  219 Wilton Rd, Westport, CT 06880

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