The Fall Market Isn’t Finished: 12 Fresh Westport, CT Listings Worth a Look

Westport’s fall market may be nearing its traditional finish line, but this week’s new inventory says the season still has another act. Twelve homes came to market between October 1 and October 8, ranging from a $995,000 Saugatuck townhome to a $6.595 million modern-coastal estate near Compo Beach.

There are also stories behind the “new” labels. One waterfront home sold only months ago and is already back at a higher price; another luxury build has returned with a meaningful reset from its original spring ask. Together, the listings offer a sharper snapshot of how Westport sellers are positioning homes as the fall window narrows.

8 Loretta Court

$6,595,000 · 6 bedrooms · 7.5 baths · 9,588 sq. ft. · Listed October 2

A short walk from Compo Beach, this new modern-coastal home by Simple Plan Home Builders spans four levels on a private cul-de-sac. Its open main floor brings together a statement fireplace, glass-enclosed office, scullery, and oversized mudroom, while the primary suite adds its own fireplace, dual walk-in closets, dressing area, and spa bath. A private top-floor suite and a walk-out lower level with gym, bar, wine cellar, media space, and office broaden the layout. Outside, a pool, multiple terraces, grilling area, and three-car garage complete the beach-area retreat.

Market note: This home first reached the market in March at $7.5 million, was reduced to $6.895 million in June, and has now returned under a fresh MLS entry at $6.595 million, about 12% below its original spring ask. That reset makes it an especially useful read on how the upper end is positioning itself as fall inventory competes for year-end buyers.

View the full listing →Listed by Coldwell Banker Realty

19 Harding Lane

$5,995,000 · 6 bedrooms · 7.5 baths · 9,824 sq. ft. · Listed October 7

Set on a flat acre at the end of a Greens Farms cul-de-sac, this new construction by AR Luxury Homes is planned for late-spring 2027 completion. The design brings together 10-foot main-level ceilings, a custom kitchen, expansive great room, formal living and dining spaces, office, wet bar, and mudroom. Six bedrooms, a finished walk-out lower level, pool and spa, and options for an elevator and additional third-floor space make this the week’s largest and highest-priced arrival, with time remaining to personalize select finishes.

View the full listing →Listed by The Riverside Realty Group

191 Bayberry Lane

$4,299,000 · 5 bedrooms · 4.5 baths · 5,981 sq. ft. · Listed October 7

Reimagined in 2025, this five-bedroom residence pairs the character of a country retreat with a bold, modern interior. A gated drive leads through landscaped grounds to generous living and entertaining spaces, including a sun-filled office, a custom kitchen with Viking appliances, and a dramatic primary suite with two dressing rooms. Outdoors, the 1.72-acre property is arranged like a private resort, with a stone terrace, summer kitchen, pool, and hot tub.

View the full listing →Listed by Coldwell Banker Realty

11 Woodside Lane

$4,050,000 · 5 bedrooms · 5.5 baths · 6,698 sq. ft. · Listed October 5

Designed by architect Peter Wormser, this private Old Hill residence combines dramatic scale with understated finishes across four completed levels. Highlights include a fireplace primary suite, two offices, a third-floor recreation room, and a finished lower level with theater, gym, and play space. Covered porches and a stone patio with a full outdoor kitchen extend entertaining outside, while downtown is just over a mile away and the New York-bound train is about nine minutes from the property.

View the full listing →Listed by William Pitt Sotheby’s International Realty

79 Riverside Avenue

$2,895,000 · 3 bedrooms · 3.5 baths · 1,841 sq. ft. · Listed October 7

Floor-to-ceiling glass and four levels of carefully planned space connect this modern home to the Saugatuck River at nearly every turn. The layout gives each bedroom a sense of separation, including a private primary suite, a guest level with its own balcony, and a lower-level family room beside another en suite bedroom. Smart-home upgrades, a waterside terrace, and dock approvals nearing completion add to the turnkey appeal, all within moments of downtown Westport. The home was designed and built by Vita Design Group, a Westport-based architecture-led design-build firm.

Market note: This is the week’s clearest boomerang listing. SmartMLS and public-sale history show that the newly built waterfront home sold for $2.65 million on June 10, 2026. Less than four months later, it is back at $2.895 million, a $245,000, or roughly 9.2%, increase over the June sale price.

View the full listing →Listed by William Pitt Sotheby’s International Realty

23 Punch Bowl Drive

$2,500,000 · 5 bedrooms · 4.5 baths · 4,017 sq. ft. · Listed October 6

On 1.25 peaceful Coleytown acres, this five-bedroom Georgian Colonial balances formal rooms with warm, character-rich gathering spaces. The standout is a large bonus room crafted with reclaimed barn wood, exposed beams, wide-plank floors, and its own fireplace. A spacious primary suite, a second suite with a private balcony, and a backyard centered on an in-ground pool and fireplace-equipped pool house give the home a strong indoor-outdoor entertaining story.

View the full listing →Listed by William Pitt Sotheby’s International Realty

7 Marsh Road

$2,049,000 · 3 bedrooms · 3 baths · 2,091 sq. ft. · Listed October 7

This Saugatuck Shores beach house is designed around the water and the relaxed rhythm of coastal living. The main level combines a stone-fireplace living room, formal dining room, and polished kitchen with custom cabinetry, professional-grade appliances, a large island, and Carrara marble. A screened porch, rear deck, and private primary-suite balcony create multiple places to take in the views, while Westport’s restaurants, shopping, train, and major routes remain just minutes away.

View the full listing →Listed by Compass Connecticut, LLC

33 Bridge Street

$1,999,999 · Coming Soon · Listed October 4

This Saugatuck opportunity combines two parcels, 29 and 33 Bridge Street, and is being offered together in as-is condition. The rear parcel holds a two-bedroom cottage, while the front parcel includes a six-bedroom, two-family residence. With options that may suit an investor, owner-occupant, renovator, or buyer exploring possible subdivision, the property stands apart from the week’s more conventional offerings. Buyers should complete their own due diligence regarding use and development possibilities.

Market note: Priced one dollar below $2 million, this is the outlier in the group: two parcels, a cottage, and a two-family residence rather than a conventional single-home offering. Its value will depend as much on due diligence and possible future use as on the buildings themselves.

View the full listing →Listed by RE/MAX Heritage

11 Turkey Hill Circle

$1,990,000 · 7 bedrooms · 4.5 baths · 4,125 sq. ft. · Listed October 4

Set on more than two acres in Greens Farms, this updated home offers unusual flexibility for multigenerational living, guests, or working from home. The renovated kitchen opens to a new deck and landscaped backyard, while the adjacent family room adds a cathedral ceiling and fireplace. Five bedrooms occupy the main bedroom level, a separate wing has its own kitchen and entrance, and the walk-out lower level contributes another bedroom, full bath, storage, and recreation space. Recent improvements include the roof, windows, exterior doors, furnace, water heater, and oil tank. It is also close to Martha Stewart’s former Westport stomping grounds on Turkey Hill Road South.

View the full listing →Listed by Coldwell Banker Realty

41 Richmondville Avenue

$1,799,000 · 2 bedrooms · 2 baths · 1,300 sq. ft. · Listed October 2

At The Mill, this bright two-bedroom residence pairs high-end finishes with a full-service condominium lifestyle. The kitchen includes new premium appliances, a large island, and generous storage, while the primary suite offers two walk-in closets. Residents share a pool, outdoor lounge and grilling spaces, rooftop terrace, resident lounge, coffee station, and on-site concierge, all within easy reach of Westport’s restaurants, shops, arts, and transportation.

Context: The polished interiors sit inside a property with a much longer story. The Mill is the adaptive reuse of the former Richmondville Manufacturing Company complex, connecting a contemporary amenity package to a piece of Westport’s industrial and artistic history.

View the full listing →Listed by Coldwell Banker Realty

4 Lookout Lane

$1,699,000 · 4 bedrooms · 3.5 baths · 2,301 sq. ft. · Listed October 5

About a mile from the beach in Greens Farms, this four-bedroom home sits on a landscaped acre with mature gardens and room to make the property your own. Its current interiors offer an inviting, carefully curated starting point, while the lot provides potential to expand or rework the home over time. A 2021 roof, 2025 oil tank, newer windows and furnace, and a whole-house generator address many of the practical details, with beaches, train service, schools, shopping, and dining all nearby.

View the full listing →Listed by Compass Connecticut, LLC

1 Sunrise Road, Unit B

$995,000 · 2 bedrooms · 2.5 baths · 1,202 sq. ft. · Listed October 7

For buyers seeking turnkey convenience, this two-bedroom Saugatuck townhome offers stylish, low-maintenance living close to the train, dining, shops, and entertainment. The open plan features hardwood floors, custom built-ins, a gas fireplace, and a quartz-topped kitchen with high-end appliances. A fenced bluestone patio extends the living space outside, while the upper-level primary suite, garage, automated shades, and durable Hardie Board exterior round out a thoughtful lock-and-leave package.

View the full listing →Listed by Coldwell Banker Realty

At this point in the season, the most revealing detail may be the variety: a buyer can move from a nearly $10,000-square-foot new build to a compact in-town condominium, a Saugatuck Shores beach house, or a multi-parcel investment opportunity without leaving Westport. The market is thinner than it was in spring, but it is not sleepy, and the pricing histories behind several of these homes show that sellers are still testing where value sits.

Availability and pricing can change quickly. Follow the links above for current status, complete details, and full photo galleries.

Listing information is from SmartMLS and was checked on October 8, 2026. Prior-sale and price-history notes were cross-checked against SmartMLS-syndicated and public-record sources. Information is deemed reliable but not guaranteed. Equal Housing Opportunity.