Westport, CT Homes for Sale with Pool

• 

  

  

  /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
• 

  

  

  /19

  $4,250,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 7,499 Sq Ft

  6 Janson Dr, Westport, CT 06880

  Exceptional new construction by AR Luxury Homes with 7,500+/- square feet of thoughtfully designed living space across four finished levels in a prime Westport location. This 6-bedroom, 6 full and 3 half bath residence blends refined craftsmanship with modern functionality, featuring an open-concept layout ideal for both everyday living and entertaining. The heart of the home is a custom-designed

  

  Brett Lieberman

  The Riverside Realty Group

  6 Janson Dr, Westport, CT 06880
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  /37

  $6,495,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,260 Sq Ft

  16 Westport Ave, Westport, CT 06880

  Experience the future of coastal living in this brand-new smart home located just steps from the sands of Compo Beach. This is the only just-completed residence on the Compo Beach side of Westport delivered as a fully integrated, self-monitoring home: rooftop solar power w/battery storage, intelligent load management, leak detection w/automatic water shutoff, energy-recovery ventilation, radiant

  Karen Scott Compass Connecticut, LLC

  16 Westport Ave, Westport, CT 06880
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  /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
• 

  

  

  /40

  $11,995,000

  New Construction

  • 5 Beds
  • 7 Baths
  • 6,050 Sq Ft

  14 Owenoke Park, Westport, CT 06880

  Summer starts here. Set on prestigious Owenoke Park steps from Compo Beach, this brand-new 6,050 sqft coastal masterpiece delivers the ultimate Westport lifestyle - pool and spa, Gray's Creek waterfront access, Long Island Sound views throughout, and a rare 3-car garage. Five ensuite bedrooms, double-island kitchen with scullery, elevator, primary suite sauna, and a lower-level loggia built for

  Deirdre Andreoli Compass Connecticut, LLC

  14 Owenoke Park, Westport, CT 06880
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  /40

  $6,795,000

  • 7 Beds
  • 6.5 Baths
  • 9,209 Sq Ft

  21 Compo Pkwy, Westport, CT 06880

  A rare offering in Westport's coveted Compo Beach neighborhood, this extraordinary estate sits on a prized double lot just moments from Compo Beach, Longshore Club, train & vibrant downtown. Featured in Westport Magazine, the property masterfully blends the charm of a beautifully preserved historic residence from 1928 w/ a remarkable 6,000 sq ft addition completed in 2008. The result is a

  Sarah Fair William Raveis Real Estate

  21 Compo Pkwy, 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
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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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  /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
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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

  $4,495,000

  New Construction $255K PRICE DROP

  • 6 Beds
  • 6.5 Baths
  • 6,611 Sq Ft

  21 Lockwood Cir, Westport, CT 06880

  Imagine a residence where every element has been considered for gracious living in stylish surroundings. This newly completed home by awardwinning Able Construction is set on a peaceful Coleytown estatearea street, framed by scenic land that enhances its sense of calm. A dramatic foyer with a woodaccented ceiling and millwork feature wall introduces interiors defined by creative decor, walls of

  Doug Bross Coldwell Banker Realty

  21 Lockwood Cir, 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
• 

  

  /40

  $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 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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  /25

  $6,800,000

  • 5 Beds
  • 3.5 Baths
  • 3,967 Sq Ft

  52 Compo Mill Cove, Westport, CT 06880

  The best vacations are the ones you never have to leave. Set on the shores of Compo Mill Cove in the heart of Westport's coveted Compo Beach neighborhood, this exceptional FEMA compliant Michael Greenberg-designed waterfront home offers the ultimate coastal lifestyle. State-of-the-art systems, including geothermal heating and cooling and tankless hot water, provide exceptional efficiency and

  Carly Woodard William Pitt Sotheby's Int'l

  52 Compo Mill Cove, 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

  • 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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  /40

  $6,375,000

  $500K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,444 Sq Ft

  21 Covlee Dr, Westport, CT 06880

  Boater's Paradise-Live the Ultimate Saugatuck Shores Waterfront Lifestyle. Experience unparalleled, direct waterfront access from this striking contemporary perched directly on the shores of Long Island Sound. Featuring its own rare private dock, this property is a true boater's/water lover's paradise. Enjoy all that Saugatuck Shores has to offer-boating, jet-skiing, paddle boarding, or kayaking

  John Foran Compass Connecticut, LLC

  21 Covlee Dr, 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

  $6,895,000

  New Construction $605K PRICE DROP

  • 6 Beds
  • 9 Baths
  • 9,576 Sq Ft

  8 Loretta Ct, Westport, CT 06880

  Introducing an exceptional new build from Simple Plan Home Builders, multiple HOBI Award winners known for iconic Westport homes. Just a short stroll to Compo Beach, this striking modern coastal retreat is privately set on a coveted cul-de-sac, blending luxury, light, and effortless living. Spanning four levels, this six-bedroom home features an airy layout with refined finishes throughout. The

  Lianne Owen Coldwell Banker Realty

  8 Loretta Ct, Westport, CT 06880
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  /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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  /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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  /33

  $1,349,000

  • 2 Beds
  • 2 Baths
  • 1,825 Sq Ft

  316 Lansdowne, Westport, CT 06880

  Enjoy a Country Club life-style in this fully renovated almost 2,000 square foot end-unit townhouse offering 2-bedrooms, 2 baths both on the main level. The ante room welcomes you into the light-filled expansive living room w/gleaming floors, vaulted ceiling & wood-burning fireplace. A separate large dining room, plus den/sun room provides ample space for entertaining. The den flows seamlessly

  Debbie Fisher William Raveis Real Estate

  316 Lansdowne, Westport, CT 06880
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  /21

  $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
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  /38

  $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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  /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
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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
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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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  /36

  $5,750,000

  • 5 Beds
  • 8 Baths
  • 6,503 Sq Ft

  31 Stonybrook Rd, Westport, CT 06880

  Tucked behind a gated entry in Old Hill, this stunning 5 bedroom, 6.2 bath home offers a rare blend of elegance, privacy and natural beauty. The property has multiple serene water features-a heated saltwater gunite pool with hot tub, a tranquil private pond with fountain and picturesque Stony Brook. The stately stone and wood exterior blends seamlessly with the lush surroundings, while inside, an

  Kristi Law William Pitt Sotheby's Int'l

  31 Stonybrook Rd, Westport, CT 06880
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  /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
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  /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.

  Garvey Fox Serhant Connecticut LLC

  4 Lantern Hill Rd, Westport, CT 06880
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  /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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  /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
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  /40

  $5,650,000

  New Construction

  • 7 Beds
  • 9 Baths
  • 8,762 Sq Ft

  8 Pleasant Valley Ln, Westport, CT 06880

  Experience modern luxury in this new SIR SIGNATURE Home by SIR Development, Westport's premier builder. Set on 1.02 private acres on a coveted cul de sac, this home offers a striking approach, 3car garage, and rare backyard privacy, all within walking distance to Bedford Middle, Staples High, Wakeman Fields, and Town Farm. A fresh contemporary aesthetic features a dramatic two story foyer, 10ft

  Doug Bross Coldwell Banker Realty

  8 Pleasant Valley Ln, Westport, CT 06880
• 

  

  /15

  $6,995,826

  New Construction

  • 6 Beds
  • 10 Baths
  • 8,417 Sq Ft

  24 Edgemarth Hill Rd, Westport, CT 06880

  This Beauty will be ready Summer 2026! Construction of this 8,417SF dream residence with pool and spa on 1 private acre in coveted Greens Farms, Westport, is in full swing. 24 Edgemarth Hill was designed and will be crafted and appointed with the finest materials - see rendering photos of what's to come. Flaunting sexy floor-to-ceiling walls of windows, stone and textured accents, vaulted

  Jaclyn Picarillo Higgins Group Bedford Square

  24 Edgemarth Hill Rd, Westport, CT 06880
• 

  

  /7

  $10,650,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 9,100 Sq Ft

  11 Dogwood Ln, Westport, CT 06880

  Another extraordinary masterpiece by Coastal Luxury Homes, ideally situated in one of Westport's premier neighborhoods. Spanning over 9000 square feet of living space this 6 bedroom estate is defined by bold architectural lines, chic designer interiors, expansive balconies and seamless indoor-outdoor living. A resort caliber pool, fully equipped outdoor kitchen, and lush manicured grounds

  Jen Kass Higgins Group Bedford Square

  11 Dogwood Ln, Westport, CT 06880
• 

  

  /40

  $5,199,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 8,935 Sq Ft

  4 Sycamore Dr, Westport, CT 06880

  Tucked away on a quiet cul de sac in the desirable Hunt Club area of Long Lots in Westport is a new construction lux home from CCO Habitats. 3 levels of finished living space with 10 foot ceilings on the 1st floor give an amazing sense of openness, as well as better functionality than 4 level homes. Think about it. Who really wants to walk up to the third floor every day? That's right; no one.

  Maryann Levanti Higgins Group Bedford Square

  4 Sycamore Dr, Westport, CT 06880
• 

  

  /36

  $2,199,000

  Open Thu 11AM - 2PM Coming Soon

  • 5 Beds
  • 7.5 Baths
  • 8,392 Sq Ft

  79 Cavalry Rd, Weston, CT 06883

  Grand and gracious, this impressive custom Colonial on estate property with a gorgeous gunite pool is ideally set in convenient Lower Weston. Just 2.3 +/- miles to the Merritt Parkway & 1.6 +/- mi to the convenient school campus & town Center, this home blends the appeal of a tranquil setting with immediate access to all amenities. Introduced from a paved circular drive, this architecturally

  Alex Chingas Coldwell Banker Realty

  79 Cavalry Rd, Weston, CT 06883

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