Westport, CT Homes for Sale with Acreage

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  /40

  $1,995,000

  • 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

  71 High Point Rd, Westport, CT 06880
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  /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

  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

  0 Clapboard Hill Rd Unit (New Build), Westport, CT 06880
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  /40

  $2,850,000

  • 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
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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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  /34

  $5,499,000

  • 6 Beds
  • 8 Baths
  • 7,748 Sq Ft

  359 Greens Farms Rd, Westport, CT 06880

  Tucked behind elegant wrought-iron gates at the end of a long private driveway, this exceptional Greens Farms estate offers the perfect blend of privacy, luxury, and convenience in one of Westport's most coveted neighborhoods. Surrounded by mature landscaping, this meticulously maintained residence feels like a private retreat while remaining steps from the Greens Farms train station, Burying

  Judy Michaelis Coldwell Banker Realty

  359 Greens Farms Rd, Westport, CT 06880
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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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  /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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  /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
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  /40

  $6,500,000

  • 6 Beds
  • 10 Baths
  • 9,349 Sq Ft

  124 Hillandale Rd, Westport, CT 06880

  An exceptional home in coveted Greens Farms, 124 Hillandale Road captures the essence of classic Connecticut living. Timeless, elegant, and impeccably maintained, this beautiful estate is surrounded by mature landscaping and a peaceful, private setting, while remaining just minutes from everything Westport has to offer. Spanning four finished levels connected by an elevator, the home seamlessly

  Meredith Cohen Serhant Connecticut, LLC

  124 Hillandale Rd, Westport, CT 06880
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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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  /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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  /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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  /39

  $2,499,000

  • 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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  /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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  /40

  $4,450,000

  New Construction Open Sun 1PM - 4PM

  • 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

  Open Sun 1PM - 4PM

  • 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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  /30

  $1,299,000

  Open Sun 12PM - 2PM

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

  5 Lehn Farm Rd, Westport, CT 06880

  In the owners' words... We moved to this home looking for an escape from city life and a place to grow our family. It has offered us all of that and more. Every inch of the home serves a purpose, creating a space that feels intentional and complete. The thoughtful size and open layout means we are never far from one another. We can prepare meals in the kitchen while watching our little ones play

  Lynne Nolan Compass Connecticut, LLC

  5 Lehn Farm Rd, 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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  /34

  $2,100,000

  $98K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,810 Sq Ft

  2 Charcoal Ln, Westport, CT 06880

  Exceptional privacy meets modern luxury on over 2 secluded acres at the end of a quiet cul-de-sac in Westport's sought-after Charcoal Hill neighborhood. Bordering a 7-acre Aspetuck Land Trust preserve, this rare property offers a peaceful, protected setting just minutes from downtown Westport, Coleytown schools, and the Merritt Parkway. Featuring 3 bedrooms, 3 full baths, and 2 additional

  Alexey Gavrilov William Pitt Sotheby's Int'l

  2 Charcoal Ln, 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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  /39

  $4,449,000

  • 6 Beds
  • 5.5 Baths
  • 6,775 Sq Ft

  48 Bayberry Ln, Westport, CT 06880

  Set on a breathtaking professionally designed acre, 48 Bayberry Lane is a beautifully reimagined 6,775sf estate offering four finished levels of exceptional living. Thoughtfully enhanced & meticulously maintained by the current owner, the home blends timeless elegance with modern comfort in a private, resort-like setting. A dramatic double-height foyer welcomes sun-filled interiors featuring

  Jaclyn Picarillo Higgins Group Bedford Square

  48 Bayberry Ln, Westport, CT 06880
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  /4

  $6,495,000

  New Construction

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

  5 Baldwin Place, Westport, CT 06880

  NEW CONSTRUCTION-READY FOR MOVE-IN! 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 spans 9,062 sq. ft. with 6 bedrooms and

  Lori Popkin Coldwell Banker Realty

  5 Baldwin Place, Westport, CT 06880
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  /40

  $15,000,000

  • 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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  /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
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  /40

  $4,795,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 8,185 Sq Ft

  2 Windy Hill Rd, Westport, CT 06880

  Resort-style living meets modern luxury at 2 Windy Hill Road. Set on a private landscaped acre, this newly completed 8,100+ SF estate by HOBI Award-winning builder Cypress Development was thoughtfully designed for the way today's luxury buyer lives, entertains, and unwinds. A dramatic two-story foyer introduces light-filled interiors highlighted by soaring ceilings, white oak flooring, natural

  Jacob Bivona Keller Williams Prestige Prop.

  2 Windy Hill Rd, Westport, CT 06880
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  /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
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  /6

  $9,860,000

  New Construction

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

  9 Over Rock Ln, Westport, CT 06880

  An exceptional modern residence by Compo Luxury Homes, designed by renowned architect Tanner White, set on over two private acres just minutes from downtown Westport, Compo Beach, and the train-approximately one hour from NYC. This 6-bedroom home spans approximately 9,200 square feet and showcases custom European windows and doors, sophisticated interiors, and seamless indoor-outdoor living. At

  Danna Rogers Higgins Group Bedford Square

  9 Over Rock Ln, Westport, CT 06880
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  /38

  $5,999,999

  New Construction Open Sun 1PM - 3PM

  • 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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  /40

  $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
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  /18

  $1,475,000

  • Land
  • 1.05 Acres
  • $1,404,762 per Acre

  50 Sylvan Rd N, Westport, CT 06880

  ATTENTION BUYERS : FLAT DRY, ONE -OF-A-KIND LAND OPPORTUNITY NOW HUGELY IMPROVED WITH WELL DEFINED SITE PLAN. Do you hope for new custom construction no bigger than "about" 4500sf, yet continue to see 7000sf and larger get the edge? Stop wishing for it and take action! Bring your architect or builder to consider a new home that meets your dream to be practically-sized for every life stage. No

  Martha Eidman Coldwell Banker Realty

  50 Sylvan Rd N, Westport, CT 06880
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  /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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  /40

  $2,790,000

  • 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
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  /40

  $3,499,000

  Open Sun 12PM - 2PM

  • 4 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
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  /36

  $5,500,000

  • 5 Beds
  • 5.5 Baths
  • 9,421 Sq Ft

  1 Twin Oaks Ln, Westport, CT 06880

  Discover exceptional modern living in this stunning new construction home set on 1.68 acres of private, serene property in Westport, CT. Designed with both luxury and functionality in mind, this residence offers 5 spacious bedrooms and 7 beautifully appointed bathrooms. The primary suite is a true sanctuary, featuring three generous closets and a spa-inspired feel. Each additional bedroom is

  Zuzana Dankova HomeSmart Homes and Estates

  1 Twin Oaks Ln, Westport, CT 06880
• 

  

  /40

  $5,599,000

  • 6 Beds
  • 9 Baths
  • 9,394 Sq Ft

  5 W Branch Rd, Westport, CT 06880

  Carefully crafted Connecticut modern farmhouse by award-winning Heine Development, this exceptional 6-bedroom residence blends timeless architecture with refined contemporary living amongst 4 finished levels on 2 private, level acres in one of Westport's most convenient luxury locations. Designed with perfection in symmetry, detail, and craftsmanship, the home pairs classic farmhouse inspiration

  Linda Skolnick Coldwell Banker Realty

  5 W Branch Rd, 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

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