Southport, CT Homes for Sale with Acreage

• 

  

  

  /40

  $2,650,000

  • 4 Beds
  • 5 Baths
  • 5,394 Sq Ft

  3007 Redding Rd, Fairfield, CT 06824

  A gorgeous Farmhouse Colonial tucked away on 2+ picturesque acres & minutes to Fairfield & Westport town await. Natural beauty, brilliant architecture, craftmanship & updates combine to make this home a standout. Featuring 12 rooms flooded w/ light over 3 levels of living. Enjoy views of a serene fallow field, a gentle stream, wildlife & stunning seasonal changes from vibrant autumn colors to

  

  Jackie Davis

  William Raveis Real Estate

  (475) 255-0748

  3007 Redding Rd, Fairfield, CT 06824
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  /39

  $2,275,000

  • 4 Beds
  • 4.5 Baths
  • 4,641 Sq Ft

  161 Sherwood Dr, Southport, CT 06890

  Enjoy the summer at 161 Sherwood Drive, a beautifully expanded and extensively updated residence located in the desirable Southport neighborhood. Offering approximately 3,679 square feet of thoughtfully designed living space, this home blends comfort, functionality, and inviting indoor-outdoor living in a private setting. The home features 4 spacious bedrooms, 4 full baths, and 1 half bath,

  

  Pam Toner

  Berkshire Hathaway NE Prop.

  (475) 348-8287

  161 Sherwood Dr, Southport, CT 06890
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  /40

  $3,250,000

  • 6 Beds
  • 6 Baths
  • 6,844 Sq Ft

  10 Side Hill Rd, Westport, CT 06880

  Now more than ever, home is a haven - a place to live, work, relax, and entertain. Privately sited on 1 beautifully landscaped acre in highly sought-after Old Hill, this sophisticated 6,000+ SF home with a brand-new pool offers 6 bedrooms, exceptional living spaces, and breathtaking western sunsets overlooking Earthplace's 62-acre nature sanctuary. A rare blend of privacy, style, and convenience,

  

  Susan Lieberman

  The Riverside Realty Group

  (475) 303-4846

  10 Side Hill Rd, Westport, CT 06880
• 

  

  /2

  $1,995,000

  Coming Soon

  • 5 Beds
  • 3.5 Baths
  • 6,310 Sq Ft

  71 High Point Rd, Westport, CT 06880

  Tucked at the end of one of Westport's most coveted cul-de-sacs, this 5-bedroom contemporary offers 6,310 sq ft of finished living space on just over a private acre, with a backyard path leading directly to Bedford Middle and Staples High School. From the foyer, a dramatic vaulted living room with skylights, built-ins and a floor-to-ceiling stone fireplace sets the tone. The glass-wrapped sunroom

  

  Hyleri Katzenberg

  Compass Connecticut, LLC

  (475) 303-7064

  71 High Point Rd, Westport, CT 06880
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  /34

  $1,689,000

  • 3 Beds
  • 2.5 Baths
  • 2,138 Sq Ft

  10 Grist Mill Ln, Westport, CT 06880

  Welcome to 10 Grist Mill Lane, a move-in ready home set on a beautiful, level acre at the end of a quiet Long Lots cul-de-sac. Thoughtfully updated throughout, this 3-4 bedroom, 2.5 bath residence offers an open and versatile floor plan designed for today's lifestyle. The dramatic living room features a vaulted ceiling and fireplace, creating a warm and inviting gathering space filled with

  

  Brett Lieberman

  The Riverside Realty Group

  (203) 350-7614

  10 Grist Mill Ln, Westport, CT 06880
• 

  

  /40

  $3,650,000

  • 6 Beds
  • 6.5 Baths
  • 6,751 Sq Ft

  9 N Ridge Rd, Westport, CT 06880

  In today's world, there is nothing more important than having a place to gather. This private retreat with a stunning residence and amazing recreational facilities can become your own private sanctuary with a tennis court, heated Gunite pool and separate pool house set among lush, meticulously curated grounds on almost 2.4 acres. This 6,700-square-foot shingle-style residence offers refined

  

  Susan Lieberman

  The Riverside Realty Group

  (475) 270-1688

  9 N Ridge Rd, Westport, CT 06880
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  /15

  $7,926,000

  New Construction

  • 6 Beds
  • 7 Baths
  • 7,200 Sq Ft

  0 Clapboard Hill Rd Unit (New Build), Westport, CT 06880

  Set within Westport's most prestigious private estate enclave, surrounded by grand coastal estates and quintessential antique treasures, this exceptional Greens Farms 2+ acre* new construction offering is poised to become one of Fairfield County's most coveted addresses. Perfectly positioned, moments from beaches, downtown boutiques, vibrant dining scene, and just an express train to Manhattan,

  

  Brett Lieberman

  The Riverside Realty Group

  (475) 203-1918

  0 Clapboard Hill Rd Unit (New Build), Westport, CT 06880
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  /9

  $3,750,000

  New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,000 Sq Ft

  22 Brett Rd, Fairfield, CT 06824

  Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among

  Andrew Whiteley Brown Harris Stevens

  22 Brett Rd, Fairfield, CT 06824
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  /28

  $2,100,000

  • 5 Beds
  • 3.5 Baths
  • 3,782 Sq Ft

  34 Pequot Trail, Westport, CT 06880

  Discover this serene setting in a sought after Old Hill neighborhood. Two thoughtful and beautifully executed additions have made this sprawling 12 room home flow with the versatility to fit today's varied lifestyles. Comfortable open living spaces have been designed with the flexibility to offer multi-generational spaces, a home office or simply to allow for room to grow in the way that pleases

  Lynn Fraund William Pitt Sotheby's Int'l

  34 Pequot Trail, Westport, CT 06880
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  /5

  $769,000

  • Land
  • 2.07 Acres
  • $371,498 per Acre

  180 Catamount Rd, Fairfield, CT 06824

  Approvals in place for this 2+ acre shovel ready lot in prestigious Greenfield Hill. 193 feet of frontage plus city water available in the street. This is an excellent opportunity to build your dream home on a beautiful cleared and leveled lot. All necessary inland wetland, conservation and septic/health department permits have been established. Located minutes to the Patterson Club and less then

  Mona Cascella William Raveis Real Estate

  180 Catamount Rd, Fairfield, CT 06824
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  /38

  $1,699,000

  • 4 Beds
  • 3 Baths
  • 2,559 Sq Ft

  4 Joann Cir, Westport, CT 06880

  HIGHEST AND BEST DEADLINE: SUNDAY, 6/7 BY 5PM -- Beautifully renovated and perfectly positioned in one of Westport's most coveted and centrally located neighborhoods, this 4-bedroom home offers the turnkey lifestyle today's buyers are seeking, with modern updates, flexible living spaces, and easy access to everything that makes Westport so special. Just minutes from top-ranked schools, downtown

  Jennifer Twombly Compass Connecticut, LLC

  4 Joann Cir, Westport, CT 06880
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  /40

  $5,549,000

  • 4 Beds
  • 5 Baths
  • 7,105 Sq Ft

  80 Compo Rd N, Westport, CT 06880

  Timeless design meets modern sustainability in this stunning shingle-style home, set on 1.5 private in-town acres. Sunlight fills every room through oversized Kolbe windows, showcasing park-like grounds and mature plantings. The kitchen impresses with custom cabinetry, a handcrafted zinc island, and top-tier Wolf and Sub-Zero appliances. Step outside to a spectacular bluestone patio with an

  Adrienne Durkin Compass Connecticut, LLC

  80 Compo Rd N, Westport, CT 06880
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  /28

  $1,600,000

  • 5 Beds
  • 2.5 Baths
  • 2,166 Sq Ft

  4 Baywood Ln, Westport, CT 06880

  Tucked away down a private drive on two serene wooded acres, this exceptional mid-century modern deck house offers the perfect blend of architectural character, privacy, and natural beauty. Bathed in tremendous natural light, the home showcases the signature design elements that make deck houses so timeless and sought after, with expansive windows, soaring ceilings, and seamless indoor-outdoor

  Meredith Cohen Serhant Connecticut, LLC

  4 Baywood Ln, Westport, CT 06880
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  /40

  $2,199,000

  • 5 Beds
  • 4.5 Baths
  • 3,380 Sq Ft

  24 Burr School Rd, Westport, CT 06880

  ***Back in market no fault of house Tucked away towards the end of a quiet cul-de-sac in a prime central Westport location, this beautifully updated home offers the perfect blend of privacy, convenience, and lifestyle. Set on 1.05 acres and just moments from town, close to schools, shopping, and commuting options, this five-bedroom residence is designed for both everyday living and effortless

  Julia Broder Coldwell Banker Realty

  24 Burr School Rd, Westport, CT 06880
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  /40

  $12,000,000

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

  4800 Congress St, Fairfield, CT 06824

  This offering is for 4800 Congress St, a one of a kind estate consists of main residence on 10.92 acres, pool, barn pool house/gym, heated paddle court, and an office pavilion. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street,offering seclusion with proximity to NYC. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century

  Leslie Razook William Pitt Sotheby's Int'l

  4800 Congress St, Fairfield, CT 06824
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  /19

  $10,500,000

  • 4 Beds
  • 5.5 Baths
  • 10,522 Sq Ft

  47 Charcoal Hill Rd, Westport, CT 06880

  Designed by renowned architect and builder Frazier Forman Peters, this stone estate is set on nearly 3.5 private, meticulously landscaped acres in Westport. Crafted over more than two decades, the residence reflects exceptional artistry, scale, and craftsmanship. A gated entry and winding stone drive arrive at a stately porte-cochere and attached two-car garage, establishing a grand sense of

  Jonathan Ducharme Serhant Connecticut, LLC

  47 Charcoal Hill Rd, Westport, CT 06880
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  /36

  $6,499,000

  • 5 Beds
  • 7 Baths
  • 6,189 Sq Ft

  775 Sasco Hill Rd, Fairfield, CT 06824

  775 Sasco Hill Road is an extraordinary estate where timeless elegance meets modern luxury. Impeccably renovated and beautifully curated by the current owners, this sophisticated residence offers three full levels of refined living set across five private, park-like acres. A dramatic cathedral foyer and soaring 9-foot ceilings create an immediate sense of scale and light, while the thoughtfully

  Suzy Ryan William Raveis Real Estate

  775 Sasco Hill Rd, Fairfield, CT 06824
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  /40

  $4,300,000

  • 6 Beds
  • 7 Baths
  • 7,170 Sq Ft

  129 Quarter Horse Ln, Fairfield, CT 06824

  Tucked away on a quiet cul-de-sac in the heart of Greenfield Hill,this exceptional 7,100-sqft estate is set on two meticulously landscaped acres,offering a rare blend of timeless elegance & modern luxury.A sweeping two-tiered bluestone terrace frames the stunning 20'x40' heated gunite pool,creating a private outdoor sanctuary designed for both relaxation & grand-scale entertaining.Completely

  Julie Vanderblue Higgins Group Real Estate

  129 Quarter Horse Ln, Fairfield, CT 06824
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  /40

  $2,749,000

  $250K PRICE DROP

  • 5 Beds
  • 7 Baths
  • 7,317 Sq Ft

  3080 Sturges Hwy, Westport, CT 06880

  Welcome to 3080 Sturges - fully renovated home set on 2.44 private acres in Fairfield's Greenfield Hill enclave on the Westport border. Offering a Westport mailing address together with Fairfield's acclaimed schools and amenities, this 7,317-square-foot modern residence blends architectural scale with contemporary comfort and luxury. A dramatic two-story foyer introduces interiors defined by

  Ryan Sullivan Berkshire Hathaway NE Prop.

  3080 Sturges Hwy, Westport, CT 06880
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  /26

  $8,995,000

  • 8 Beds
  • 10 Baths
  • 15,172 Sq Ft

  2 Judy Point Ln, Westport, CT 06880

  Set on over 3 private acres with sweeping water views, 2 Judy Point Lane is a remarkable Westport waterfront estate offering approximately 14,000 square feet of living space and a rare compound-style layout. The property consists of two substantial residences connected by a breezeway, creating exceptional flexibility for multi-generational living, extended guests, or a private guest house.

  Daniel Kramp Christie's International Real Estate

  2 Judy Point Ln, Westport, CT 06880
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  /22

  $4,995,000

  New Construction

  • 5 Beds
  • 7 Baths
  • 5,550 Sq Ft

  1 Coastal Ct, Westport, CT 06880

  Introducing 1 Coastal Court, a rare opportunity to own in Westport's only gated community, an exclusive four-lot enclave envisioned and built by Joe Feinleib, founder of Coastal Luxury Homes and one of Fairfield County's most respected builders.This private neighborhood blends timeless architecture with modern luxury. Each custom residence, ranging from 5,000 to 7,500 square feet, plus generous

  Julie Vanderblue Higgins Group Real Estate

  1 Coastal Ct, Westport, CT 06880
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  /38

  $2,895,000

  • 4 Beds
  • 6 Baths
  • 6,252 Sq Ft

  171 Paddock Hill Ln, Fairfield, CT 06824

  Timeless craftsmanship, extraordinary scale & a level of construction quality increasingly difficult to find define this exceptional estate located in Fairfield's only gated community. Set on over 2 professionally landscaped acres on the Fairfield/Westport border, this home showcases generous room proportions, architectural detail & custom millwork seldom seen. A dramatic double-height foyer

  Kate Cacciatore William Raveis Real Estate

  171 Paddock Hill Ln, Fairfield, CT 06824
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  /38

  $4,050,000

  • 6 Beds
  • 9 Baths
  • 9,525 Sq Ft

  278 North Ave, Westport, CT 06880

  Set in one of Westport's most prestigious estate enclaves, this exceptional shingle-style residence defines luxury living with a rare emphasis on multi-generational comfort, timeless architecture, and impeccable craftsmanship. Designed and built by a renowned architect and builder for a Fortune 500 CEO, the home reflects uncompromising quality, enduring design, and gracious curb appeal that

  Cyd Hamer William Pitt Sotheby's Int'l

  278 North Ave, Westport, CT 06880
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  /16

  $795,000

  • Land
  • 1.02 Acres
  • $779,412 per Acre

  844 Mill Hill Terrace, Fairfield, CT 06890

  This 1.02 acre parcel offers the rare combination of privacy and premier location. Tucked away in a quiet Southport neighborhood, yet just minutes to the harbor, beaches, train, restaurants, and charming village shops - it's the best of both worlds. The possibilities are endless - City water, City sewer and Natural Gas are available in the street. Whether you envision a timeless New England

  Barbara Sweeney Coldwell Banker Realty

  844 Mill Hill Terrace, Fairfield, CT 06890
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  /38

  $2,199,000

  $51K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,651 Sq Ft

  4 Cardinal Ln, Westport, CT 06880

  Welcome to 4 Cardinal Lane ~ a beautifully expanded and thoughtfully updated home set on two private, level acres in one of Westport's most desirable cul-de-sac neighborhoods. Originally built in 1964 and enhanced with a significant 2015 addition, this 4-bedroom, 3.5 bath residence offers over 4,100 square feet of versatile living space designed for both everyday comfort and effortless

  Amanda Thaw The Riverside Realty Group

  4 Cardinal Ln, Westport, CT 06880
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  /7

  $2,495,000

  New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,900 Sq Ft

  108 Old Farm Rd, Fairfield, CT 06825

  108 Old Farm Road is a stunning new construction currently underway in one of Weston's most desirable settings. This five-bedroom, 5.5-bath home offers 4,568 square feet above grade plus a 1,400 square foot finished heated lower level with home theater, totaling nearly 6,000 square feet of exceptional living space. The main level features soaring two-story ceilings, a formal dining room, home

  Alex De Camargo eXp Realty

  108 Old Farm Rd, Fairfield, CT 06825
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  /11

  $5,990,000

  New Construction

  • 6 Beds
  • 6.5 Baths
  • 6,900 Sq Ft

  10 Mary Jane Ln, Westport, CT 06880

  New construction by renowned Red Coat Homes, ideally set on a quiet cul-de-sac in a premier Westport neighborhood. Designed by architect Judith Larson, this exceptional home offers over 7,000 sq ft of refined living space on more than one acre, complete with a resort-style pool. Timeless architecture and sophisticated finishes create spaces ideal for entertaining, work, and everyday living, with

  Danna Rogers Higgins Group Bedford Square

  10 Mary Jane Ln, Westport, CT 06880
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  /27

  $1,399,000

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  5 Lehn Farm Rd, Westport, CT 06880

  Tucked away in a storybook setting on over an acre of land, this beautifully rebuilt 3-bedroom home offers effortless one-level living surrounded by nature. A charming brook and picturesque wooden footbridges create a peaceful, private retreat unlike any other. Designed with an open floor plan and soaring vaulted ceilings, the sun-filled interior feels both spacious and inviting. The primary

  Lynne Nolan Compass Connecticut, LLC

  5 Lehn Farm Rd, Westport, CT 06880
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  /40

  $25,000,000

  • 6 Beds
  • 11 Baths
  • 19,569 Sq Ft

  1131 Sasco Hill Rd, Fairfield, CT 06824

  Sasco Point- A Rare Waterfront Estate. Perched on over 11 acres with 450 feet directly on Long Island Sound, Sasco Point is an extraordinary coastal retreat. Nestled at the end of prestigious Sasco Hill Road, this architecturally stunning estate blends Swedish, Dutch, and Moorish influences, creating a residence that is as elegant as it is timeless. A discreet gated entrance leads to a winding

  Andrew Whiteley Brown Harris Stevens

  1131 Sasco Hill Rd, Fairfield, CT 06824
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  /40

  $3,450,000

  $225K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 6,015 Sq Ft

  4 Charcoal Ln, Westport, CT 06880

  A rare offering indeed! Welcome to 4 Charcoal Lane, an unrivaled multi-generational estate, thoughtfully reimagined with an array of stunning features and superior craftsmanship. Sited on 2 private acres, this extraordinary property offers priceless panoramic views of a 7-acre nature preserve, affording permanent tranquility and a sense of wonder. The meticulous renovations center around a

  Carol Langeland William Pitt Sotheby's Int'l

  4 Charcoal Ln, Westport, CT 06880
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  /39

  $7,350,000

  • 6 Beds
  • 6.5 Baths
  • 6,585 Sq Ft

  69 Beachside Ave, Westport, CT 06880

  Set behind gates on over four exquisitely landscaped acres in Westport's coveted Beachside enclave, 69 Beachside Avenue is a private coastal estate offering a rare blend of scale, privacy, and resort-style living just moments from the shoreline. A long, gracious approach leads to a timeless residence defined by exceptional craftsmanship and sun-filled interiors. Expansive living spaces feature

  John Raus Berkshire Hathaway NE Prop.

  69 Beachside Ave, Westport, CT 06880
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  /4

  $1,100,000

  • Land
  • 2.65 Acres
  • $415,094 per Acre

  22 Brett Rd, Fairfield, CT 06824

  An exceptional opportunity to build your dream home on one of the most desirable and scenic settings in Fairfield. This beautiful, flat 2.65-acre parcel-approved by the Wetlands Com. for a 5-bedroom, 5-bathroom residence with a pool and pool house-offers both privacy and prestige. The property is situated in the estate section of Greenfield Hill. With its driveway access on Brett Road, a

  Andrew Whiteley Brown Harris Stevens

  22 Brett Rd, Fairfield, CT 06824
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  /40

  $4,450,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 8,356 Sq Ft

  159 Turnpike, Westport, CT 06880

  Are you dreaming of an estate property? Something a bit more than the generic flat acre on a cul de sac? How do two acres on the Aspetuck River sound to you? With views from your bedroom? The sounds of a waterfall next door lulling you to sleep? Having sunnies tickle your toes in the summertime? Maybe a bit of fly fishing for trout? Or perhaps some paddleboarding? Yes, of course, there's a 20x40

  Maryann Levanti Higgins Group Bedford Square

  159 Turnpike, Westport, CT 06880
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  /6

  $22,825,000

  • 8 Beds
  • 10 Baths
  • 12,946 Sq Ft

  11 Beachside Common, Westport, CT 06880

  Direct Waterfront | Greens Farms An extraordinary new waterfront estate by award-winning Coastal Luxury Homes is coming to one of the most coveted stretches of the Connecticut shoreline. Set in the heart of Greens Farms, this spectacular 12,948 square foot modern residence will span four levels and capture sweeping, unobstructed views across Sherwood Island, Burying Hill Beach, and Long Island

  Andrew Whiteley Brown Harris Stevens

  11 Beachside Common, Westport, CT 06880
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  /40

  $4,100,000

  $400K PRICE DROP

  • 5 Beds
  • 8 Baths
  • 9,819 Sq Ft

  1 Flower Farm Ln, Westport, CT 06880

  Absolutely exquisite colonial is located on one of the most sought after neighborhoods. This home will greet you w/a mahogany front porch that leads inside to a grand foyer. This timeless residence boasts a custom kitchen w/high-end appliances, a Butler's pantry, large island & the convenience of a desk station. The elegant formal living room features a cozy fireplace, while the family room

  Heather Fitzgerald Coldwell Banker Realty

  1 Flower Farm Ln, Westport, CT 06880
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  /26

  $1,250,000

  • 4 Beds
  • 2.5 Baths
  • 1,542 Sq Ft

  18 Hales Rd, Westport, CT 06880

  Compo Beach...

  Scott Kelland CLS Group

  18 Hales Rd, Westport, CT 06880
• 

  

  /4

  $6,495,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 9,062 Sq Ft

  5 Baldwin Place, Westport, CT 06880

  New Construction by Westport Family Homes - Elevator, July Completion. Privately set at the end of a quiet cul-de-sac in the coveted Long Lots neighborhood, this 2.3-acre, flat, tree-lined property offers a rare combination of privacy and endless possibilities for creating a luxury compound. Introducing a truly exceptional estate by award-winning Builder, Westport Family Homes. The residence

  Lori Popkin Coldwell Banker Realty

  5 Baldwin Place, Westport, CT 06880
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  /32

  $1,800,000

  • 6 Beds
  • 6.5 Baths
  • 3,897 Sq Ft

  622,644 Melville Ave, Fairfield, CT 06825

  The combination of 622 and 644 Melville Av, two adjacent properties which would provide an ideal setting for a very unique and rare opportunity for a very special family compound on a private acre of land. This package would include garages with 5 bays , inground pool and remodeled in-law apartment. Please refer to listings 24167602 and 24167599 for complete details. * 622 Melville Ave. was

  John Shea William Raveis Real Estate

  622,644 Melville Ave, Fairfield, CT 06825
• 

  

  /40

  $1,800,000

  • 5 Beds
  • 3.5 Baths
  • 3,345 Sq Ft

  422 Riverside Ave, Westport, CT 06880

  A rare opportunity in the heart of Westport's coveted Saugatuck section. Set on 1.10 dry acres w/ beautiful views overlooking the Saugatuck River, this property known historically as Twin Hickory's offers a unique blend of history, charm, & future potential. Rich in character & dating back more than a century, the property traces its roots to the Franklin M. Raymond estate. Orig constructed as a

  Jay Cannone William Raveis Real Estate

  422 Riverside Ave, Westport, CT 06880
• 

  

  /18

  $4,000,000

  New Construction

  • 7 Beds
  • 9 Baths
  • 7,105 Sq Ft

  20 Fresenius Rd, Westport, CT 06880

  We've saved the best for last! Of the 4 homes built at the end of this quiet and centrally located Westport cul-de-sac, this is the most expansive, and it's loaded with top-tier amenities. Entertain or hang out in style in gracious rooms curated by Susan Tracy Designs featuring a warm color palate, and not often found finishes like Venetian plaster and built-in hallway millwork. The open

  Patricia Shea Coldwell Banker Realty

  20 Fresenius Rd, Westport, CT 06880

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