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Browse All Westport CT Properties with Pool for Sale

39 Whitney Glen, Unit 39, Westport image
39 Whitney Glen, Unit 39, Westport — Whitney Glen $925,000

Move right into this gut renovated townhouse condo in Whitney Glen, a sought after community in Westport. Thoughtfully updated throughout, this sun filled home features a...

  • 2 Beds
  • 2 Baths
  • 24217459 MLS
  • Whitney Glen Bldg.
92 Compo Rd N, Westport image
92 Compo Rd N, Westport $3,395,000

92 Compo Road N. pairs classic architecture, meticulous craftsmanship, private 1 acre property, pool and spa with an enviable near town location. Moments from Main Street...

  • 4 Beds
  • 5 Baths
  • 24217119 MLS
17 Greenbrier Rd, Westport image
17 Greenbrier Rd, Westport $3,450,000

Welcome to 17 Greenbrier Rd- an irreplaceable masterpiece that perfectly balances elite, high-end refinement with effortless daily livability. Nestled high in a vibrant N...

  • 4 Beds
  • 4 Baths
  • 24216789 MLS
41 Richmondville Ave Unit 311, Westport image
41 Richmondville Ave Unit 311, Westport — The Mill $1,799,000

Experience the pinnacle of sophisticated, carefree living in this stunning luxury condominium at Westport's historic and reimagined landmark, The Mill. Seamlessly combini...

  • 2 Beds
  • 2 Baths
  • 24216042 MLS
  • The Mill Bldg.
313 Harvest Commons Unit 313, Westport image
313 Harvest Commons Unit 313, Westport — Harvest Commons $1,300,000

Warm and welcoming from the moment you enter - this light and bright new condominium offering will make you feel at home. Vaulted ceilings, gleaming hardwood floors throu...

  • 2 Beds
  • 3 Baths
  • 24215497 MLS
  • Harvest Commons Bldg.
159 Easton Rd, Westport image
159 Easton Rd, Westport $4,450,000

YES - we have the CO!! :) The home you've been waiting for is ready for sale and yes; you can close and move in in time to host for the holidays!! How much would you love...

  • 6 Beds
  • 8 Baths
  • 24215185 MLS
61 Clapboard Hill Rd Unit A, Westport image
61 Clapboard Hill Rd Unit A, Westport $7,900,000

Exceptional architecture, refined craftsmanship, and a country/coastal lifestyle. This spectacular Westport estate, to be built by Soundmark Luxury Homes, offers a rare e...

  • 6 Beds
  • 7 Baths
  • 24211051 MLS
58 Terra Nova Cir Unit 58, Westport image
58 Terra Nova Cir Unit 58, Westport — Terra Nova At Westport $1,649,000

Seller has requested best and highest offers by Wednesday, October 28, 2026 at 4PM. Move right in to this pristine townhome in Westport's exclusive Terra Nova condomini...

  • 2 Beds
  • 3 Baths
  • 24214379 MLS
  • Terra Nova At Westport Bldg.
14 High Point Rd, Westport image
14 High Point Rd, Westport $2,999,999

Classic Colonial 5 Bedroom 5 - 1/2 Bath set on over 1 acre with a Gunite Swimming Pool on Westport's longest and perhaps, most sought after Cul-De-Sac! Almost 4700 sq ft ...

  • 5 Beds
  • 6 Baths
  • 24213615 MLS
4 Surrey Ln, Westport image
4 Surrey Ln, Westport $2,795,000

Lovingly cherished by the same family for over 50 years, this 1965 five bedroom home presents a wonderful opportunity to create something truly special in one of Westport...

  • 5 Beds
  • 4 Baths
  • 24213304 MLS
142 Easton Rd, Westport image
142 Easton Rd, Westport $2,950,000

A rare opportunity to own an exceptional woodland estate, where space, serenity, and natural beauty converge. Set beyond a long, gracefully winding driveway, this expansi...

  • 5 Beds
  • 6 Baths
  • 24212624 MLS
4 Turkey Hill Ln, Westport image
4 Turkey Hill Ln, Westport $3,295,000

Built in 2013 by Chris O'Dell, this 5-bedroom, 5.5-bathroom, 5,318 sq. ft. home sits on 1.07 acres in Westport's Long Lots neighborhood. Used exclusively as a summer retr...

  • 5 Beds
  • 5 Baths
  • 24212748 MLS
19 Harding Ln, Westport image
19 Harding Ln, Westport $5,995,000

Magnificent new construction by AR Luxury Homes on a flat, private acre at the end of a coveted cul-de-sac in Greens Farms. Thoughtfully designed finishes by Tara Benet D...

  • 6 Beds
  • 9 Baths
  • 24199970 MLS
41 Richmondville Ave Unit 303, Westport image
41 Richmondville Ave Unit 303, Westport — The Mill Westport $1,799,000

Welcome to The Mill offering a sophisticated, effortless approach to Westport living, pairing a distinctive setting with thoughtful amenities and the convenience of a con...

  • 2 Beds
  • 2 Baths
  • 24211506 MLS
  • The Mill Westport Bldg.
8 Loretta Ct, Westport image
8 Loretta Ct, Westport $6,595,000

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...

  • 6 Beds
  • 9 Baths
  • 24211630 MLS
8 Tar Rock Rd, Westport image
8 Tar Rock Rd, Westport $7,399,000

With views over rooftops and to the Long Island Sound, this extraordinary new residence brings a new level of luxury to Westport's coveted Compo Beach area. Inspired by i...

  • 6 Beds
  • 7 Baths
  • 24205429 MLS
41 Richmondville Ave Unit 105, Westport image
41 Richmondville Ave Unit 105, Westport — The Mill Westport $1,949,000

Historic character meets refined modern design in this beautifully appointed one-bedroom plus den, two-bath residence at The Mill Westport. A gracious foyer provides a pr...

  • 2 Beds
  • 2 Baths
  • 24209251 MLS
  • The Mill Westport Bldg.
20 Turkey Hill Cir, Westport image
20 Turkey Hill Cir, Westport $6,800,000 ▼

The home offers timeless and classic New England, the charm you have been seeking. Set up on a quiet hill in the heart of Green Farms, this picturesque shingle home check...

  • 5 Beds
  • 9 Baths
  • 24206974 MLS
51 Compo Beach Rd, Westport image
51 Compo Beach Rd, Westport $7,200,000

Exceptional coastal living in Westport's coveted Compo Beach neighborhood. Built in 2024, 51 Compo Beach Road is a stunning four-bedroom home with spectacular Long Island...

  • 4 Beds
  • 4 Baths
  • 24204128 MLS
9 N Ridge Rd, Westport image
9 N Ridge Rd, Westport $3,400,000

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 be...

  • 6 Beds
  • 7 Baths
  • 24208426 MLS
14 Owenoke Park, Westport image
14 Owenoke Park, Westport $10,985,000

100% FEMA compliant & storm friendly AND 100% completed, this special new construction Bluewater Home is priced to SELL. Located steps from Compo Beach on prestigious Owe...

  • 5 Beds
  • 7 Baths
  • 24207610 MLS
21 Sturges Commons, Westport image
21 Sturges Commons, Westport $6,250,000

NEW CONSTRUCTION NEAR COMPLETION IN THE COVETED HUNT CLUB NEIGHBORHOOD BY THE MOST SOUGHT-AFTER LUXURY BUILDER, MATTERA CONSTRUCTION, celebrated for creating architectura...

  • 6 Beds
  • 9 Baths
  • 24194597 MLS
35 Bonnie Brook Rd, Westport image
35 Bonnie Brook Rd, Westport $1,629,000

New Listing! First time on the market in 50 years! Bonnie Brook Road is the kind of neighborhood where the quiet is noticeable. It's a place where you can actually use th...

  • 4 Beds
  • 3 Baths
  • 24203692 MLS
12 Beltas Farm Ln, Westport image
12 Beltas Farm Ln, Westport $7,985,000

12 Beltas Farm Lane is an extraordinary new construction estate in Westport, Connecticut, set within Beltas Farm, one of Westport, Connecticut's newest and most distincti...

  • 6 Beds
  • 6 Baths
  • 24205532 MLS
124 Harvest Commons Unit 124, Westport image
124 Harvest Commons Unit 124, Westport — Harvest Commons $1,325,000

Nestled in a prime location within a beautifully maintained complex, this exceptional home offers access to premier community amenities-including a pool and tennis courts...

  • 2 Beds
  • 4 Baths
  • 24204033 MLS
  • Harvest Commons Bldg.
9 Over Rock Ln, Westport image
9 Over Rock Ln, Westport $9,860,000

Newly completed, this exceptional modern estate offers approximately 9,200 square feet on 2.1 private acres just minutes from downtown Westport, Compo Beach, and Metro-No...

  • 6 Beds
  • 9 Baths
  • 24205443 MLS
12 Strathmore Ln Unit 12, Westport image
12 Strathmore Ln Unit 12, Westport — Strathmore Lane $675,000

Move right in to this newly-fully-updated-in-2025 end-unit townhouse offering a fresh, stylish interior and an exceptional location. A brand-NEW kitchen anchors the open-...

  • 2 Beds
  • 3 Baths
  • 24203810 MLS
  • Strathmore Lane Bldg.
2 Windy Hill Rd, Westport image
2 Windy Hill Rd, Westport $4,600,000

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 Cypres...

  • 6 Beds
  • 8 Baths
  • 24204809 MLS
24 Edgemarth Hill Rd, Westport image
24 Edgemarth Hill Rd, Westport $7,015,000

Just 2 weeks from completion, come see this 8,417SF dream residence w/sauna, pool & spa on 1 private acre in coveted Greens Farms as the finishing touches are being made....

  • 6 Beds
  • 10 Baths
  • 24204343 MLS
32 Narrow Rocks Rd, Westport image
32 Narrow Rocks Rd, Westport $6,999,999

NEW CONSTRUCTION BY RENOWNED LUXURY BUILDER MATTERA CONSTRUCTION - STEPS TO COMPO BEACH! A rare opportunity to own a brand-new, architecturally refined home in one of We...

  • 6 Beds
  • 9 Baths
  • 24196804 MLS
31 Stonybrook Rd, Westport image
31 Stonybrook Rd, Westport $5,199,000 ▼

From the moment you enter the gates of this Old Hill estate, you know you've arrived- a rare sanctuary built with a level of custom stonework and craftsmanship impossible...

  • 5 Beds
  • 8 Baths
  • 24201547 MLS
166 Long Lots Rd, Westport image
166 Long Lots Rd, Westport $2,995,000

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 ...

  • 4 Beds
  • 5 Baths
  • 24097062 MLS
5 Baldwin Pl, Westport image
5 Baldwin Pl, Westport $6,495,000

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...

  • 6 Beds
  • 8 Baths
  • 24194674 MLS
22 Cavalry Rd, Westport image
22 Cavalry Rd, Westport $5,900,000

Set behind private gates in Westport's prestigious Red Coat estate area, this extraordinary luxury residence offers the utmost in privacy and sophisticated design. Though...

  • 7 Beds
  • 8 Baths
  • 24194285 MLS
52 Compo Mill Cv, Westport image
52 Compo Mill Cv, Westport $6,800,000

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 exceptio...

  • 5 Beds
  • 4 Baths
  • 24193394 MLS
16 Westport Ave, Westport image
16 Westport Ave, Westport $6,495,000

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 Co...

  • 4 Beds
  • 5 Baths
  • 24192357 MLS
316 Lansdowne Unit 316, Westport image
316 Lansdowne Unit 316, Westport — Lansdowne $1,349,000

Enjoy a Country Club life-style in this fully renovated almost 2,000 square foot end-unit townhouse offering Primary & 2nd bedrooms, 2 baths both on the main level. The a...

  • 2 Beds
  • 2 Baths
  • 24179902 MLS
  • Lansdowne Bldg.
10 Beltas Farm Ln, Westport image
10 Beltas Farm Ln, Westport $8,450,000

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 ...

  • 6 Beds
  • 8 Baths
  • 24190641 MLS
38 Prospect Rd, Westport image
38 Prospect Rd, Westport $9,675,690 ▲

A bold expression of sculptural architecture and modern organic design, this one-of-a-kind Green's Farms estate with stone cottage is set on 1.19 artfully layered acres w...

  • 6 Beds
  • 10 Baths
  • 24190177 MLS
13 Edgemarth Hill Rd, Westport image
13 Edgemarth Hill Rd, Westport $5,499,000 ▼

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 ...

  • 7 Beds
  • 8 Baths
  • 24183173 MLS
124 Hillandale Rd, Westport image
124 Hillandale Rd, Westport $6,500,000

An exceptional home in coveted Greens Farms, 124 Hillandale Road captures the essence of classic Connecticut living. Timeless, elegant, and impeccably maintained, this be...

  • 6 Beds
  • 10 Baths
  • 24184011 MLS
53 Clinton Ave, Westport image
53 Clinton Ave, Westport $2,499,000 ▼

Incredibly located moments from town and convenient to schools, shopping, commuting options and more, this sparkling home showcases pride of ownership. A new 2026 drivewa...

  • 5 Beds
  • 6 Baths
  • 24079819 MLS
279 Saugatuck Ave, Westport image
279 Saugatuck Ave, Westport $14,900,000

Panoramic views of Long Island Sound extend from this gated, resort-like estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes...

  • 5 Beds
  • 9 Baths
  • 24179641 MLS
22 Evergreen Ave, Westport image
22 Evergreen Ave, Westport $4,850,000

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 i...

  • 5 Beds
  • 5 Baths
  • 24172211 MLS
19 Mortar Rock Rd, Westport image
19 Mortar Rock Rd, Westport $4,699,000 ▼

Stunning modern transitional home built by Compo Luxury Homes in 2024 and ideally located just minutes to downtown Westport, Compo Beach, and the train. Set on .65 acres ...

  • 6 Beds
  • 8 Baths
  • 24174833 MLS
8 Pleasant Valley Ln, Westport image
8 Pleasant Valley Ln, Westport $5,650,000

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 offer...

  • 7 Beds
  • 9 Baths
  • 24172635 MLS
6 Janson Dr, Westport image
6 Janson Dr, Westport $4,250,000

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. ...

  • 6 Beds
  • 9 Baths
  • 24165540 MLS
11 Clapboard Hill Rd, Westport image
11 Clapboard Hill Rd, Westport $3,995,000 ▼

An antique jewel set on 3.5 extraordinary acres in the heart of Greens Farms, ready to be transformed into your forever home. Brimming with timeless charm and endless pot...

  • 6 Beds
  • 8 Baths
  • 24168553 MLS
69 Beachside Ave, Westport image
69 Beachside Ave, Westport $7,350,000

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 ...

  • 6 Beds
  • 7 Baths
  • 24152219 MLS
4 Sherwood Island Ln, Westport image
4 Sherwood Island Ln, Westport $10,500,000 ▼

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...

  • 7 Beds
  • 7 Baths
  • 24160355 MLS

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Westport Homes with Pool

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Michael Parsell
Trusted Realty Partners
(203) 880-9675
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324 Elm Street, Suite 105B

Monroe, CT 06468

Broker: John Fontana REB.0794755

(203) 880-9675
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