Westport, CT Houses for Sale with Private Pool

/28
$6,995,000
- 6 Beds
- 6 Baths
- 5,190 Sq Ft
2 Bluewater Hill S, Westport, CT 06880

Discover unparalleled living at 2 Bluewater Hill South, a magnificent 5000+ SF estate on one of Westport's most prestigious street just steps from Compo Beach. This exceptional home combines sophisticated coastal elegance with resort-style amenities, offering 6 bedrooms, 6 baths, and breathtaking LI Sound views. The coveted Bluewater Hill location provides exclusive private beach access while

Susan Lieberman

The Riverside Realty Group

(203) 350-0478

2 Bluewater Hill S, Westport, CT 06880
/25
$3,999,000
- 6 Beds
- 8 Baths
- 6,000 Sq Ft
57 Evergreen Ave, Westport, CT 06880

Walk to downtown shops and restaurants from this stunning, reimagined, & rebuilt 1920 Dutch colonial home, situated on a spacious 1.17-acre in-town property.This is truly a work of art, as 2 properties have been seamlessly combined into one, creating a private oasis set way back from the road.Upon entering the home, you will be captivated by the meticulous attention to detail & the perfect blend

Hyleri Katzenberg

Compass Connecticut, LLC

(475) 253-3404

57 Evergreen Ave, Westport, CT 06880
/40
$4,750,000
- 3 Beds
- 3 Baths
- 2,650 Sq Ft
34 Shorehaven Rd, Norwalk, CT 06855

Exclusive Waterfront Retreat in Gated Island Community - Just One Hour from NYC. Welcome to a rare opportunity to own one of only twelve homes on a secluded private island on the Long Island Sound. This 3-bedroom, 3-bathroom waterfront home offers the perfect escape from city life while remaining effortlessly connected to the best of Fairfield County. Perched between the sparkling waters of Long

Toni Mickiewicz

William Pitt Sotheby's Int'l

(475) 405-1946

34 Shorehaven Rd, Norwalk, CT 06855
/2
$4,895,000 New Construction
- 6 Beds
- 9 Baths
- 9,224 Sq Ft
21 Warnock Dr, Westport, CT 06880

Expected for completion end of summer 2025, this striking architectural design meets refined luxury in a meticulously crafted 9,200+/- sq ft, 6-bedroom, 6 full, & 3 half bath new residence. Showcasing the collaborative excellence of AR Luxury Homes w/ interior design by Mary Beth Woods & architectural vision by Donald William Fairbanks, this exceptional property represents the pinnacle of modern

Brett Lieberman

The Riverside Realty Group

(475) 255-6647

21 Warnock Dr, Westport, CT 06880
/40
$2,995,000
- 4 Beds
- 4.5 Baths
- 5,629 Sq Ft
166 Long Lots Rd, Westport, CT 06880

Your private oasis awaits! This beautifully renovated home offers an ideal location with easy access to town, shopping, and the beach. Designed with comfort and style in mind, the home features inviting living spaces including a two-story family room with an open staircase. The gourmet eat-in kitchen is open to a sitting area with a corner fireplace. Two family bedrooms with en-suite baths

Michelle Genovesi William Raveis Real Estate

166 Long Lots Rd, Westport, CT 06880
/40
$6,980,000 New Construction
- 5 Beds
- 4.5 Baths
- 4,791 Sq Ft
22 Apple Tree Trail, Westport, CT 06880

PRICE ADJUSTED! Compo Beach living, 2 short blocks from beach on private road! Luxury construction, just completed. 5 bed, 4.5 bath modern home w/ all of the lush amenities seen in the finest resorts both inside & out. Custom Italian cabinetry by L'Ottocento in kitchen, butler's pantry, bathrooms, and mudroom. 9ft.+ ceilings, open stairs w/ glass railings & oak floors. Entry hall w/ crystal

Deborah Aulfinger Goldan Home Realty, LLC.

22 Apple Tree Trail, Westport, CT 06880
/5
$4,899,000
- 5 Beds
- 8 Baths
- 7,400 Sq Ft
10 Tierney Ln, Westport, CT 06880

This is the second of 2 custom homes in final stages of completion, beautifully sited at the end of a private lane in the heart of Greens Farms. Combining classic design with modern detailing by an established local builder of premier residences, this masterfully crafted home is sure to delight even the most discerning buyer. The main level showcases expert millwork and warm white oak accents

Laurie Crouse Coldwell Banker Realty

10 Tierney Ln, Westport, CT 06880
/37
$4,895,000
- 7 Beds
- 7.5 Baths
- 9,035 Sq Ft
26 Morningside Dr S, Westport, CT 06880

Welcome to 26 Morningside Drive South - the first completed residence in the prestigious Sherwood Estates at Greens Farms, where timeless heritage and modern luxury meet. This newly built, four-story home is a masterclass in design, set in one of Westport's most sought-after neighborhoods. Every element has been thoughtfully curated to elevate daily living and impress when entertaining. Step

John Schiaroli Coldwell Banker Realty

26 Morningside Dr S, Westport, CT 06880
/8
$7,399,000
- 6 Beds
- 7.5 Baths
- 8,035 Sq Ft
7 Roshab Ln, Westport, CT 06880

This listing includes 1000 SF pool house/ADU. Set on over 2 acres in one of Westport's most prestigious neighborhoods, this stunning new construction by HOBI award winner Rick Benson, blends modern luxury with timeless design. Surrounded by mature trees, the home offers privacy & serenity minutes from trains, shopping, & beaches. Inside, discover 6 spacious bedrooms, 7 full/1 half baths,

Totney Benson Coldwell Banker Realty

7 Roshab Ln, Westport, CT 06880
/34
$4,200,000
- 6 Beds
- 8 Baths
- 6,960 Sq Ft
42 Morningside Dr S, Westport, CT 06880

Nestled within a picturesque enclave of distinguished luxury homes in Westport's coveted Greens Farms neighborhood, you'll know you've arrived as mature, stately hedges guide you down a flowering, tree-lined driveway. This Hampton-style home has been masterfully reimagined and updated by its current owners. It sings with natural light, refined millwork, custom moldings, and offers an elegant

Jaclyn Picarillo Higgins Group Bedford Square

42 Morningside Dr S, Westport, CT 06880
/40
$4,300,000
- 7 Beds
- 8 Baths
- 6,981 Sq Ft
102 Compo Rd S, Westport, CT 06880

THE ESTATES AT SOUTH COMPO - SIR Development presents a stunning new enclave of two luxury residences set back on beautiful property, each with their own distinct Modern style and pool. Officially designated by the State of CT as a Scenic Roadway, this location offers ultimate convenience to every amenity that makes Westport one of the most highly desired towns in the nation. This home begins

Doug Bross Coldwell Banker Realty

102 Compo Rd S, Westport, CT 06880
/40
$5,950,000
- 6 Beds
- 9 Baths
- 8,817 Sq Ft
29 Sturges Commons, Westport, CT 06880

Masterfully crafted by Mattera Construction, this 12,000+/- sq ft residence sits on 1.3+/- pastoral acres on coveted Sturges Commons, a vibrant neighborhood known for block parties and a strong sense of community. Designed for both luxury and functionality, this home boasts exquisite custom finishes, soaring ceilings, and impeccable interior design. The main level offers a chef's kitchen, a

Doug Bross Coldwell Banker Realty

29 Sturges Commons, Westport, CT 06880
/22
$4,900,000
- 7 Beds
- 5.5 Baths
- 7,995 Sq Ft
37 Green Acre Ln, Westport, CT 06880

A rare investment opportunity to own a storied 1936 estate on a desirable, private street in the heart of Westport. Set on 4.3 acres at the end of a tranquil cul-de-sac, this legacy property offers the ultimate in privacy and location, just one mile from both Westport's vibrant town center and the beach. The primary residence spans approximately 8,000 square feet, rich with timeless architecture

Lisa Bortz William Pitt Sotheby's Int'l

37 Green Acre Ln, Westport, CT 06880
/31
$6,500,000
- 6 Beds
- 6.5 Baths
- 6,585 Sq Ft
69 Beachside Ave, Westport, CT 06880

Nestled along Westport's prestigious 'Gold Coast,' this architecturally magnificent estate on 4+ acres of park-like grounds with a breathtaking pool and professional-grade Har-Tru tennis court is a haven for luxury living and distinguished entertaining. Surrounded by major estates in one of the most sought-after coastal regions in the Northeast, it boasts access to pristine beaches, sophisticated

Doug Bross Coldwell Banker Realty

69 Beachside Ave, Westport, CT 06880
/30
$5,200,000
- 6 Beds
- 7.5 Baths
- 9,630 Sq Ft
355 Greens Farms Rd, Westport, CT 06880

Exceptional Gated Estate in Greens Farms! Welcome to 355 Greens Farms Rd, a spectacular 2.25 acres estate designed for luxurious living and ultimate entertaining. This stunning home is a dream for car enthusiasts, featuring a four-car garage with room for lifts, making it perfect for showcasing and maintaining your collection. Step inside to find a brand-new kitchen and a newly designed primary

Meredith Cohen Serhant Connecticut, LLC

355 Greens Farms Rd, Westport, CT 06880
/40
$4,375,000
- 6 Beds
- 11 Baths
- 10,414 Sq Ft
5 Boxwood Ln, Westport, CT 06880

Refined living awaits on Boxwood Lane, a prime Hunt Club cul-de-sac featuring tranquil private entrances to stately colonial style homes. From its cobblestone-lined, semi-circular driveway to the backyard pool and bluestone patio oasis, the grounds of 5 Boxwood Lane are simply spectacular. The home itself stands apart, meticulously designed with exquisite details and custom amenities. Four

Karen Scott Compass Connecticut, LLC

5 Boxwood Ln, Westport, CT 06880
/40
$5,850,000
- 6 Beds
- 5.5 Baths
- 6,588 Sq Ft
17 River Ln, Westport, CT 06880

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

Alex Chingas Coldwell Banker Realty

17 River Ln, Westport, CT 06880
/37
$4,999,000
- 4 Beds
- 4.5 Baths
- 5,885 Sq Ft
10 Surf Rd, Westport, CT 06880

Offered for the first time in over 50 years, this cherished, custom-built waterfront retreat on Bermuda Lagoon is an extraordinary find. Lovingly maintained and never flooded, 100 feet of private beach, a deepwater dock, and breathtaking views of Long Island Sound and Bermuda Lagoon. Designed for year-round enjoyment, the home's soaring ceilings and expansive windows perfectly frame the stunning

Inna Agujen Coldwell Banker Realty

10 Surf Rd, Westport, CT 06880
/40
$4,600,000
- 4 Beds
- 3.5 Baths
- 4,636 Sq Ft
87 Red Coat Rd, Westport, CT 06880

MOST UNIQUE HOUSE IN WESTPORT LARGE LOG HOME ON THE RIVER THAT IS STOCKED WITH TROUT. INGROUND GUNITE POOL BEAUTIFUL GROUNDS VERY PRIVATE ONE FLOOR LIVING. 4 BEDROOMS 3.5 BATHS. 1 HOUR TO NYC BEACH ACCESS. WONDERFUL RARE OPPORTUNITY TO OWN THE HOME YOU HAVE ALWAYS WONDERED ABOUT. THE BEAUTIFUL TRANQUIL RIVERVIEW LODGE LOG HOME THAT SITS ON THE MAJESTIC SAUGATUCK RIVER. WITH OVER 500+ FEET OF

Rebecca Ellsley Higgins Group Bedford Square

87 Red Coat Rd, Westport, CT 06880
/40
$4,500,000
- 5 Beds
- 9 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 YellowBrick Real Estate LLC

1 Flower Farm Ln, Westport, CT 06880
/10
$4,995,000 New Construction
- 6 Beds
- 7 Baths
- 7,500 Sq Ft
107 Old Rd, Westport, CT 06880

Welcome to 107 Old Road, an exceptional new development by Joe Feinleib founder of Coastal Luxury Homes. Soon to be the only gated community development in Westport, CT, this uniqiue four-lot enclave presents unparalleled luxury and privacy. Each custom home, to be designed in collaboration with your client, boasts approximately 6,500 to 7,500 square feet of living space, with an additional 1,100

Nickolaos Andronikidis Shelby's Realty Services

107 Old Rd, Westport, CT 06880
/40
$4,395,000
- 5 Beds
- 4.5 Baths
- 6,013 Sq Ft
29 Covelee Dr, Norwalk, CT 06855

Welcome to Saugatuck Shores, an exceptional waterfront enclave offering unparalleled luxury and privacy.A boater's dream come true w/ your own dock and direct access to LI Sound.This hidden gem neighborhood has a labyrinth of quiet,walkable streets, culminating in a cul-de-sac.Private Covlee Assn membership w/ sandy beach & social gatherings.The 5 bedroom high-end masterpiece w/ elevator was

Julie Vanderblue Higgins Group Real Estate

29 Covelee Dr, Norwalk, CT 06855
/39
$2,700,000
- 5 Beds
- 4.5 Baths
- 4,179 Sq Ft
114 Cross Hwy, Westport, CT 06880

Welcome to a truly one-of-a-kind home in the heart of Westport - where timeless Colonial charm meets the elegance of a Parisian hotel particulier. Set on an acre+ this home offers sophistication, space, and serenity throughout. The light-filled LR stuns with vaulted ceilings, HW floors, a wood-burning fireplace, and French doors opening directly to the deck and pool - the perfect setting for

Robert Appell Coldwell Banker Realty

114 Cross Hwy, Westport, CT 06880
/40
$2,465,000
- 4 Beds
- 3 Baths
- 4,412 Sq Ft
8 Northfield Dr, Westport, CT 06880

This is the perfect house in the perfect location-just minutes from top-rated schools, playgrounds, ballfields, and houses of worship. Set on a picture-perfect acre of lush, manicured lawn, this Colonial style home offers serene views of a large pond while overlooking 8+ acres of private, protected meadowland. A gas-fired, whole-house generator provides seamless backup power for year-round peace

Helen Cusa Brown Harris Stevens

8 Northfield Dr, Westport, CT 06880
/40
$2,649,000
- 6 Beds
- 4.5 Baths
- 5,083 Sq Ft
4 the Fenway, Westport, CT 06880

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

Mary Kate Klemish-Boehm Brown Harris Stevens

4 the Fenway, Westport, CT 06880
/31
$3,900,000
- 6 Beds
- 5.5 Baths
- 7,468 Sq Ft
86 Old Rd, Westport, CT 06880

Magnificent move-in ready new construction brought to you by Sound Home Builders. Centrally located in the heart of Westport's coveted Long Lots, Hunt Club and Greens Farms neighborhoods. Elegant design and finishing detail, soaring ceilings and master craftsmanship throughout. Oversized European windows and doors fill the home with natural light. The kitchen features custom cabinetry, warm hues,

Tom Preston Keller Williams Realty

86 Old Rd, Westport, CT 06880
/27
$3,895,000
- 6 Beds
- 7 Baths
- 5,510 Sq Ft
2 Webb Rd, Westport, CT 06880

Welcome to everything you've ever wanted! NEW CONSTRUCTION, Pool, cul-de-sac, in a neighborhood that is great for walking and biking in central Westport. Walk to Post Rd shops/restaurants, Winslow dog park, even Main St., Library, and the Levitt Pavilion! 6 bedrooms/5 full baths/ 2 half baths. 4 finished floors of living space. Gunite Pool w/Automatic Safety Cover and Room for Cabana. HUGE, FLAT

Lori Popkin Coldwell Banker Realty

2 Webb Rd, Westport, CT 06880
/40
$3,650,000
- 5 Beds
- 5 Baths
- 3,561 Sq Ft
6 Over Rock Ln, Westport, CT 06880

Showings start Wednesday afternoon. Welcome to 6 Over Rock Lane - a stunning 1920s colonial retreat in the heart of Westport, Connecticut. Created by renowned designer Dan Barsanti and artist Rena Levine, it blends timeless New England charm with sophisticated modern living. A unique move-in opportunity with curated designer furniture offered. Set on a quiet, luxurious street in one of Westport's

Judy Michaelis Coldwell Banker Realty

6 Over Rock Ln, Westport, CT 06880
/38
$3,400,000
- 5 Beds
- 9 Baths
- 8,639 Sq Ft
249 Sturges Hwy, Westport, CT 06880

Don't let the address fool you-Sturges Highway is a peaceful, tree-lined street in Westport's sought-after lower-tax area, offering privacy, serenity, and convenience just minutes from town and schools.With NEW MECHANICALS including a NEW FURNACE, NEW ROTH OIL TANK, an NEW 80 GALLON HOT WATER HEATER, and a WHOLE HOUSE GENERATOR this home is move-in ready with peace of mind.This 8,000+ sq ft home

Lainie Floyd William Pitt Sotheby's Int'l

249 Sturges Hwy, Westport, CT 06880
/31
$2,249,000
- 6 Beds
- 5.5 Baths
- 5,489 Sq Ft
130 Easton Rd, Westport, CT 06880

Unique opportunity to renovate this classic Westport estate on three professionally landscaped acres with a pool. You will love the great room with views of the pond and property. Six bedrooms makes space for everyone with a separate guest wing that is perfect for an au-pair.

David Weber Compass Connecticut, LLC

130 Easton Rd, Westport, CT 06880
/35
$2,799,000
- 4 Beds
- 3 Baths
- 3,156 Sq Ft
11 Dogwood Ln, Westport, CT 06880

Experience the best of Westport living in this stunning Mid Century Modern residence set on 1.87 prime acres in the heart of town. This is all about the property! Tucked away on a beautifully landscaped property, this 4-bedroom home offers the perfect blend of privacy, modern design, and everyday convenience. Inside, expansive windows bathe the open living spaces in natural light, with soaring

Linda Skolnick Coldwell Banker Realty

11 Dogwood Ln, Westport, CT 06880
/29
$2,249,000
- 4 Beds
- 3 Baths
- 4,231 Sq Ft
10 Twin Falls Ln, Westport, CT 06880

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

Kit Tingley Higgins Group Bedford Square

10 Twin Falls Ln, Westport, CT 06880
/40
$2,895,000
- 6 Beds
- 4.5 Baths
- 6,856 Sq Ft
5 Northside Ln, Westport, CT 06880

A true Westport landmark, Staffordshire Hall is an extraordinary gated stone estate blending timeless grandeur with modern luxury. Privately nestled on manicured grounds, this bespoke manor spans three levels of meticulously crafted living space. A sweeping circular drive leads to the columned entrance. The Great Hall stuns with a stone hearth, coffered ceilings, and French doors opening to the

Alex Chingas Coldwell Banker Realty

5 Northside Ln, Westport, CT 06880
/38
$3,525,000
- 5 Beds
- 6 Baths
- 4,668 Sq Ft
91 Turkey Hill Rd S, Westport, CT 06880

Welcome to 91 Turkey Hill Rd S a beautifully upgraded 5 bed 4 full and 2 half bath home blending classic charm with modern luxury. Every inch of this residence reflects thoughtful design and top tier craftsmanship. Step inside to discover 6 brand-new, spa-inspired bathrooms, meticulously renovated with the finest materials for a truly indulgent experience. HW floors and soaring ceilings thruout

Robert Appell Coldwell Banker Realty

91 Turkey Hill Rd S, Westport, CT 06880
/38
$3,375,000
- 5 Beds
- 4 Baths
- 3,700 Sq Ft
3 Nassau Rd, Westport, CT 06880

Discover Westport's Premier Coastal Gem. Immerse yourself in modern elegance with this stunning new beach house, located in the highly sought-after Saugatuck Shores neighborhood. Constructed in 2022, this five-bedroom, four-and-a-half-bathroom residence spans over 3,700 square feet of finished living space. Tucked away on a peaceful cul-de-sac, the home offers easy access to the vibrant energy

Doug Bross Coldwell Banker Realty

3 Nassau Rd, Westport, CT 06880
/2
$10,995,000
- 5 Beds
- 7 Baths
- 6,025 Sq Ft
14 Owenoke Park, Westport, CT 06880

Bluewater Home presents another beach property in the sought after Compo location. Construction has started on this 6100+sqft modern designed home with private yard, pool with spa, water views of the pond and walking distance to Compo Beach. Enjoy new construction living in the heart of Westport while peacefully tucked away on a private cul-de-sac

Deirdre Andreoli Compass Connecticut, LLC

14 Owenoke Park, Westport, CT 06880
/40
$11,800,000
- 5 Beds
- 8 Baths
- 10,800 Sq Ft
260 Hillspoint Rd, Westport, CT 06880

Experience the unparalleled luxury of this exquisite Compo Beach seaside home,a masterpiece of design and craftsmanship, designed by renowned architect Peter Cadoux. Just steps from a private beach, this architectural gem is bathed in natural light and boasts breathtaking panoramic water views from nearly every room.The full chef's kitchen opens to a radiant sunroom with a glass ceiling, perfect

Elizabeth Steffen Higgins Group Bedford Square

260 Hillspoint Rd, Westport, CT 06880
/5
$6,649,000 New Construction
- 6 Beds
- 7.5 Baths
- 8,035 Sq Ft
7 Roshab Ln, Westport, CT 06880

Set on over 2 acres in one of Westport's most prestigious neighborhoods, this stunning new construction by HOBI award winner Rick Benson, blends modern luxury with timeless design. Surrounded by mature trees, the home offers privacy & serenity minutes from trains, shopping, & beaches. Inside, discover 6 spacious bedrooms, 7 full/1 half baths, sun-filled interiors with a seamless flow between

Totney Benson Coldwell Banker Realty

7 Roshab Ln, Westport, CT 06880
/38
$5,499,000 New Construction
- 6 Beds
- 9 Baths
- 9,550 Sq Ft
11 Tierney Ln, Westport, CT 06880

Impressively positioned at the end of a private lane in the heart of the Greens Farms, this is the first of 2 custom homes in final stages of construction. Combining classic design with modern detailing, this masterfully crafted home by an established local builder of premier residences is sure to delight even the most discerning buyer. The main level exudes luxury, showcasing the expert millwork

Laurie Crouse Coldwell Banker Realty

11 Tierney Ln, Westport, CT 06880
/15
$6,875,480 New Construction
- 7 Beds
- 8 Baths
- 8,800 Sq Ft
1 Sturges Hwy Unit Lot 2, Westport, CT 06880

Design Your Dream Home with an Award-Winning Builder Step into a world of elegance and sophistication with a soon-to-be-built 6,600 sq. ft. masterpiece by Coastal Luxury Homes. Known for their innovative designs, sleek modern lines, and unparalleled craftsmanship, Coastal Luxury Homes has earned a reputation for creating some of the most sought-after residences. With a focus on prime location,

Annie Klyver Higgins Group Real Estate

1 Sturges Hwy Unit Lot 2, Westport, CT 06880

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