Westport, CT Homes for Sale with Acreage

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  /36

  $3,550,000

  • 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

  9 N Ridge Rd, Westport, CT 06880
• 

  

  

  /17

  $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

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

  

  

  /40

  $2,795,000

  $55K PRICE DROP

  • 6 Beds
  • 7 Baths
  • 9,454 Sq Ft

  25 Hermit Ln, Westport, CT 06880

  Experience timeless elegance in this extraordinary Colonial estate nestled in Westport's coveted Red Coat neighborhood. Offering more than 7,000sf of beautiful living space, plus an additional 2,400sf in the finished lower level, this exceptional residence combines luxury, comfort, and functionality. Featuring 6 spacious bedrooms and 5.2 baths, the home is thoughtfully designed for both everyday

  Paul Cranick eXp Realty

  25 Hermit Ln, Westport, CT 06880
• 

  

  

  /40

  $8,450,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 9,893 Sq Ft

  10 Beltas Farm Ln, Westport, CT 06880

  Extraordinary New Construction home on one of Westport's newest premier cul-de-sacs. Offering nearly 10,000 SF of impeccably finished living space, this exceptional home blends timeless elegance w/ modern luxury & showcases the finest craftsmanship throughout.Designed with an uncompromising attention to detail, features include exquisite millwork, stunning custom cabinetry, spectacular ceiling

  Linda Skolnick Coldwell Banker Realty

  10 Beltas Farm Ln, Westport, CT 06880
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  /38

  $1,999,000

  • 5 Beds
  • 3.5 Baths
  • 2,864 Sq Ft

  110 Cross Hwy, Westport, CT 06880

  Experience modern luxury in this beautifully reimagined home, set on 1.57 scenic, park-like acres. Thoughtfully renovated, this 2,864 sq ft residence offers open-concept living spaces filled with natural light and sophisticated finishes throughout. The designer kitchen features a stunning island and premium cabinetry, flowing seamlessly into the dining and living areas with a dramatic linear

  Stephanie Ferreira BHGRE Gaetano Marra Homes

  110 Cross Hwy, Westport, CT 06880
• 

  

  /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
• 

  

  /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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  /14

  $6,650,000

  New Construction

  • 5 Beds
  • 7 Baths
  • 11,000 Sq Ft

  4 Lantern Hill Rd, Westport, CT 06880

  An exceptional opportunity to create a custom luxury residence on 1.2 acres in Westport. With approved plans and permits already in place, buyers may bring their preferred builder and collaborate with the project architect to tailor the home to their vision. The property offers a streamlined path toward creating a distinctive residence while retaining flexibility in design, specifications, and

  Ian Defronze Serhant Connecticut, LLC

  4 Lantern Hill Rd, Westport, CT 06880
• 

  

  /10

  $9,200,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 8,623 Sq Ft

  38 Prospect Rd, Westport, CT 06880

  A bold expression of sculptural architecture and modern organic design, this exceptional Green's Farms estate is set on 1.19 artfully layered acres with stacked stone walls, gardens, and a striking stone and white stucco facade. Walls of glass flood the interiors with natural light, seamlessly connecting the home to the private grounds and heated pool. Every space is composed with architectural

  Jaclyn Picarillo Higgins Group Bedford Square

  38 Prospect Rd, Westport, CT 06880
• 

  

  /40

  $2,799,000

  • 5 Beds
  • 3.5 Baths
  • 4,471 Sq Ft

  4 Crawford Rd, Westport, CT 06880

  Privately nestled in Westport's coveted Old Hill neighborhood, this extraordinary five-bedroom New England residence offers a rare opportunity to own a home where timeless character & modern comfort come together beautifully. Thoughtfully updated while preserving its remarkable architectural details, the residence features sun-filled interiors, beautifully scaled rooms, & an inviting warmth

  Barbara Sweeney Coldwell Banker Realty

  4 Crawford Rd, Westport, CT 06880
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  /6

  $3,500,000

  • 3 Beds
  • 3.5 Baths
  • 1,299 Sq Ft

  0 Calf Pasture Island Unit 24147619, Norwalk, CT 06854

  Opportunities like this are rare. Calf Pasture Island is one of just 10 private islands off the coast of Norwalk, offering a uniquely private coastal setting and a blank canvas for imagination. Properties like this remain in the same hands for many decades and do not come up for sale often. Located approximately a half mile offshore, it is among the closest islands to the mainland and takes its

  Andrew Whiteley Brown Harris Stevens

  0 Calf Pasture Island Unit 24147619, Norwalk, CT 06854
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  /5

  $1,399,000

  Open Thu 11AM - 2PM Coming Soon

  • 4 Beds
  • 2 Baths
  • 1,834 Sq Ft

  4 Half Mile Common, Westport, CT 06880

  Welcome to a home that makes everyday living and entertaining easy. Set on a friendly cul-de-sac where neighbors wave hello, and bike rides and dog walks are part of the rhythm of the street. This 4-bedroom split-level offers space, warmth, and a location that's hard to beat. At the heart of the home is an open-plan living room and modern eat-in kitchen, highlighted by soaring vaulted ceilings

  Amy Swanson William Raveis Real Estate

  4 Half Mile Common, Westport, CT 06880
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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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  /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 mere minutes from top-rated schools, shopping, restaurants and all that Westport has to offer. Sited on 2 private acres, this extraordinary property offers panoramic views of a 7-acre nature preserve, affording permanent tranquility. The meticulous renovations center around a gracious farmhouse-style

  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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  /37

  $4,450,000

  New Construction

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

  159 Easton Rd, 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 Easton Rd, Westport, CT 06880
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  /40

  $3,400,000

  • 5 Beds
  • 4.5 Baths
  • 6,166 Sq Ft

  27 Woody Ln, Westport, CT 06880

  This beautifully renovated Ward French custom home offers elegant formal spaces, a chef's kitchen, flexible guest and office accommodations, a luxury primary suite, fitness studio and sitting room with balcony. The home's 2,442 square foot lower level offers tremendous untapped potential, providing an opportunity to create customized luxury amenities such as a home theater, golf simulator, wine

  Allan Styer Compass Connecticut, LLC

  27 Woody Ln, 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
• 

  

  /40

  $10,500,000

  $5M PRICE DROP

  • 7 Beds
  • 6.5 Baths
  • 6,215 Sq Ft

  4 Sherwood Island Ln, Westport, CT 06880

  Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings ever offered. For more than 65 years, it has been held and enjoyed by the same family as a place to gather, unwind, and take in the ever-changing views across Sherwood Island Park and Long Island Sound. Surrounded by protected

  Andrew Whiteley Brown Harris Stevens

  4 Sherwood Island Ln, Westport, CT 06880
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  /34

  $1,850,000

  Open Sun 1AM - 4PM

  • 6 Beds
  • 4 Baths
  • 3,240 Sq Ft

  5 Aspetuck Ln, Westport, CT 06880

  Rare Opportunity to own two private acres on the Aspetuck River in Westport. Tucked away at the end of a quiet cul-de-sac, this gracious Colonial offers an extraordinary blend of privacy, natural beauty and relaxed country living. Set on two spectacular acres, the property extends to and beyond the banks of the river, creating a truly unique waterfront retreat. A natural riverside setting invites

  Beverly Walsh William Raveis Real Estate

  5 Aspetuck Ln, Westport, CT 06880
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  /17

  $7,990,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 6,000 Sq Ft

  4 Compo Pkwy, Westport, CT 06880

  Build your coastal dream home on a rare, full acre* property along one of Compo Beach's most coveted cul-de-sacs, where opportunities of this caliber seldom become available. Ideally positioned just across from Longshore and moments from the shoreline, this extraordinary setting places Westport's most treasured amenities at your fingertips: golf, tennis, swimming, boating, beaches, playgrounds,

  Jaclyn Picarillo Higgins Group Bedford Square

  4 Compo Pkwy, Westport, CT 06880
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  /2

  $1,600,000

  • Land
  • 1.13 Acres
  • $1,415,929 per Acre

  0 River Ln, Westport, CT 06880

  Lee's Pond Retreat | 1.13 Acres of Opportunity A rare opportunity to create your dream home on 1.13 acres along the shores of Lee's Pond in Westport. This residentially zoned property offers a unique combination of privacy, natural beauty, and exceptional potential. Currently home to an existing tennis court, the property is ready for a developer or end user to bring their vision to life and

  Kim Harizman Compass Connecticut, LLC

  0 River Ln, Westport, CT 06880
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  /2

  $1,495,000

  • Land
  • 1 Acre
  • $1,495,000 per Acre

  9 Berkeley Rd, Westport, CT 06880

  **Plans submitted and waiting on final approvals likely completed July/August.** Rare opportunity to build new in one of Westport's most sought-after neighborhoods. Set on approximately one acre on a quiet Coleytown side street, this property offers the ideal combination of privacy, natural surroundings, and convenience. Surrounded by established homes and just minutes from top-rated schools,

  Jonathan Makovsky Compass Connecticut, LLC

  9 Berkeley Rd, Westport, CT 06880
• 

  

  /22

  $4,995,700

  New Construction

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

  22 Dawn Dr, Westport, CT 06880

  Come walk this stunning 1.5 acre lot with me - totally private, tucked at the end of a cul de sac in Long Lots. Peace, quiet, and the highest quality custom home spec'd to your wishlist by Coastal Luxury Homes is yours at 22 Dawn Drive. Go bigger/smaller, add an in-law suite or extra bedroom, an art studio, include a pool/spa, pickle court... let's discuss all the possibilities. Square footage

  Jaclyn Picarillo Higgins Group Bedford Square

  22 Dawn Dr, Westport, CT 06880
• 

  

  /22

  $9,860,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 9,200 Sq Ft

  9 Over Rock Ln, Westport, CT 06880

  Newly completed by Compo Luxury Homes, this exceptional modern estate offers approximately 9,200 square feet on 2.1 private acres just minutes from downtown Westport, Compo Beach, and Metro-North. Thoughtfully designed with European craftsmanship, premium finishes, and sophisticated smart-home technology, the home blends timeless design with exceptional functionality. A dramatic floating

  Danna Rogers Higgins Group Bedford Square

  9 Over Rock Ln, Westport, CT 06880
• 

  

  /40

  $5,999,999

  New Construction

  • 7 Beds
  • 7.5 Baths
  • 8,700 Sq Ft

  13 Edgemarth Hill Rd, Westport, CT 06880

  Set on 1.70 private acres in the heart of Greens Farms, this distinctive new construction by Dwell offers a rare combination of timeless design, exceptional privacy, and resort-caliber outdoor living. Offering 8,700+/- sq ft, this exceptional residence features 7 bedrooms, 8 bathrooms, and thoughtfully designed living spaces crafted with an emphasis on enduring design rather than passing trends.

  Doug Bross Coldwell Banker Realty

  13 Edgemarth Hill Rd, Westport, CT 06880
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  /40

  $3,795,000

  $55K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,418 Sq Ft

  61 Clapboard Hill Rd, Westport, CT 06880

  Located in prestigious Greens Farms, this European-inspired Colonial offers a rare opportunity to enjoy immediate charm while planning for the future. Set behind private gates on expansive, picturesque grounds, the property is surrounded by multimillion-dollar estates-making it an exceptional canvas for new construction or a significant estate expansion. The existing home is beautifully

  Lorelei Atwood Higgins Group Real Estate

  61 Clapboard Hill Rd, Westport, CT 06880
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  /39

  $5,925,000

  • 6 Beds
  • 9 Baths
  • 6,561 Sq Ft

  3 Stony Point W, Westport, CT 06880

  Located within the highly desirable Stony Point association, this exceptional home offers a rare combination of privacy, water views, and convenience just moments from the train, local restaurants, and everyday amenities. This particular home enjoys private dock membership, providing summer boat access just steps from your door. Completely transformed and expanded in 2016, the home features over

  Debra Shaughnessy Coldwell Banker Realty

  3 Stony Point W, Westport, CT 06880
• 

  

  /16

  $1,899,000

  • 4 Beds
  • 3.5 Baths
  • 3,514 Sq Ft

  36 Lyons Plain Rd, Westport, CT 06880

  Rarely does an opportunity like this become available in Westport. Set on 2.36 private acres with approximately 300 feet along the scenic Aspetuck River, this exceptional property offers a remarkable setting to renovate, expand, or create the custom estate you've always envisioned. The existing four-bedroom residence features a spacious primary suite with fireplace, an expansive kitchen, and a

  Charlotte Cotton William Raveis Real Estate

  36 Lyons Plain Rd, Westport, CT 06880
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  /20

  $6,495,000

  New Construction

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

  5 Baldwin Place, Westport, CT 06880

  Rarely does a new construction home and property like this come on the market in Westport. Set at the end of a cul-de-sac, in the coveted Long Lots neighborhood, this 2.3-acre, flat property offers a rare combination of privacy and convenience to town. The property features a resort-style, saltwater pool w/spa and automatic safety cover, expansive covered and open-air patios, and a fully equipped

  Lori Popkin Coldwell Banker Realty

  5 Baldwin Place, Westport, CT 06880
• 

  /2

  $2,650,000

  • Land
  • 1.23 Acres
  • $2,154,472 per Acre

  4 Lantern Hill Rd, Westport, CT 06880

  Rare opportunity to build a custom residence on 1.2 acres in Westport. The previous home has been demolished, and the property is offered with approved architectural plans. Bring your preferred builder and collaborate with the project architect to tailor the design to your vision. Also listed as a to-be-built single-family residence.

  Ian Defronze Serhant Connecticut, LLC

  4 Lantern Hill Rd, Westport, CT 06880
• 

  

  /40

  $2,670,000

  $120K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,072 Sq Ft

  56 Charcoal Hill Rd, Westport, CT 06880

  A rare opportunity to own one of Charcoal Hill's signature properties, this exceptional Frazier Peters stone home pairs historic craftsmanship with a level of care and refinement that is increasingly hard to find. Set atop 2.3 +/- gated acres and introduced through a stunning circular drive, the residence showcases Peters' hallmark use of native stone, warm wood tones, and artisan detail,

  Doug Bross Coldwell Banker Realty

  56 Charcoal Hill Rd, Westport, CT 06880
• 

  

  /11

  $2,750,000

  • Land
  • 1 Acre
  • $2,750,000 per Acre

  4 Surrey Ln, Westport, CT 06880

  Set in one of Westport's most desirable locations, 4 Surrey Drive offers a rare opportunity to renovate or build new on a beautiful, level one-acre property. The existing approximately 3,500-square-foot home is being sold as-is and features a pool, providing an ideal foundation for a renovation or a chance to create a new home tailored to your vision. Enjoy the convenience of walking to the train

  Kim Harizman Compass Connecticut, LLC

  4 Surrey Ln, Westport, CT 06880
• 

  

  /40

  $3,499,000

  • 5 Beds
  • 4.5 Baths
  • 3,778 Sq Ft

  240 North Ave, Westport, CT 06880

  "MEADOW WOOD" - Nearly two acres of Westport's most spectacular land is the setting for this storied estate, which has been completely remodeled, expanded and transformed for modern living. Totally fenced & screened w/privacy trees, this unique property offers rare sophistication with a stunning main residence, gunite pool, and a 2,447+/- sqft barn. Gated driveways lead to both the main house &

  Doug Bross Coldwell Banker Realty

  240 North Ave, Westport, CT 06880
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  /43

  $14,900,000

  • 5 Beds
  • 8 Baths
  • 9,546 Sq Ft

  279 Saugatuck Ave, Westport, CT 06880

  Panoramic vistas of Long Island Sound extend from this gated, resort-style estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes in the coastal views from walls of windows, French doors, and private balconies. Effortless indoor-outdoor flow defines the main level, where a charming screened-in porch and awning-covered veranda overlook a Gunite pool with

  Joseph Barbieri Sotheby's International Realty

  279 Saugatuck Ave, Westport, CT 06880
• 

  

  /27

  $1,495,000

  • 1 Bed
  • 1 Bath
  • 1,551 Sq Ft

  11 Hitchcock Rd, Westport, CT 06880

  An exceptional offering on 1.38 private acres in the heart of Westport. Ideally situated just moments from vibrant Main Street, this centrally located property offers convenient access to shopping, dining, parks, tennis courts, beaches, the train, and Westport's award-winning schools. It provides an outstanding foundation for creating a one-of-a-kind estate. At the heart of this property stands

  Kelley Long Thrush Berkshire Hathaway NE Prop.

  11 Hitchcock Rd, Westport, CT 06880
• 

  

  /12

  $1,695,000

  • 4 Beds
  • 3.5 Baths
  • 4,572 Sq Ft

  40 Pequot Trail, Westport, CT 06880

  Located in the highly sought after Old Hill Neighborhood - set back from the street on a one acre lot. This is a 4 bedroom colonial with a spacious first floor lay out including a formal living room with a lovely mantled fireplace, formal dining room, with French doors to the sunroom, library or office with bookcases, eat-in kitchen with an island and a relaxed family room featuring a fireplace,

  John Geheran William Raveis Real Estate

  40 Pequot Trail, Westport, CT 06880
• 

  

  /40

  $4,850,000

  • 5 Beds
  • 5 Baths
  • 5,103 Sq Ft

  22 Evergreen Ave, Westport, CT 06880

  Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate

  Valerie Alvarez Serhant Connecticut, LLC

  22 Evergreen Ave, Westport, CT 06880
• 

  

  /22

  $5,900,000

  • 7 Beds
  • 7.5 Baths
  • 9,800 Sq Ft

  22 Cavalry Rd, Westport, CT 06880

  Set behind private gates in Westport's prestigious Red Coat estate area, this extraordinary luxury residence offers the utmost in privacy and sophisticated design. Thoughtfully conceived with elegant architecture, exceptional proportions, soaring 10-foot ceilings on the main level, 9-foot ceilings on the second floor and finished lower level, and light-filled interiors, the home blends

  Cyd Hamer William Pitt Sotheby's Int'l

  22 Cavalry Rd, Westport, CT 06880
• 

  

  /40

  $2,195,000

  • 5 Beds
  • 5.5 Baths
  • 5,131 Sq Ft

  159 Newtown Turnpike, Weston, CT 06883

  This exceptional 150-year-old antique estate in Lower Weston has been thoughtfully and stylishly reimagined, seamlessly blending timeless historic character with the luxurious amenities of contemporary living. The main residence strikes a perfect balance between grand, flowing entertaining spaces and cozy, intimate nooks tailored for remote work or quiet relaxation. At the heart of the home, an

  Peter Depalo William Raveis Real Estate

  159 Newtown Turnpike, Weston, CT 06883

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