October 2026

WHEN THE HEADLINES QUIET DOWN, LOCAL DATA MATTERS MOST

ABOUT

LISTINGS

RECENTLY SOLD

CONNECT

WHERE DO WESTPORT BUYERS MOVE FROM?

• According to a 2025 report, Connecticut is the leading source. Many purchasers are already living in the state, including people moving from neighboring communities or within Westport itself.
• New York is a significant source of buyers. This is consistent with Westport's appeal to people who want a suburban home while retaining connections to the New York metropolitan area.
• Other states contribute smaller shares. Texas, Massachusetts, California, Florida, and New Jersey were among the origins identified in the local report.

OCTOBER TOPIC: When headlines quiet down, local data matters most.

October reminds us that real estate is deeply local and resilient.

MARKET SNAPSHOT:

MARKET RECAP:

September brought a mixed market across Fairfield County, with home prices holding strong in some towns while sales activity and inventory levels shifted. Weston and Fairfield saw median sale prices rise 6% and 16%, respectively, while Westport and Wilton experienced declines; notably, homes continued to sell at or above asking price in all four towns, with sale-to-list ratios ranging from 100.2% to 104.9%. Meanwhile, rising inventory in Westport, Fairfield, and Wilton offers buyers more options, while sellers who price strategically and present their homes well remain best positioned to attract serious buyers.

OCTOBER SELLER TIP:

Presentation and pricing matter more than seasonality.

OCTOBER BUYER TIP:

October can offer leverage before year-end.

HOUSE of the MONTH:

56 WRIGHT STREET

This previous Old Hill listing from Jillian Klaff is an excellent example of a value driven home that appeals to strategic buyers. With its sought after location, generous size and potential to meet a range of lifestyle needs, the property highlights how savvy buyers can look beyond the price tag to recognize a home's long-term value, versatility, and possibilities.

WHAT'S HAPPENING LOCALLY?

• Beginning Oct 1st through the end of March, dogs are allowed back at the beach. Designated areas are prohibited and there are clean-up and leash requirements so make sure you know and follow the Compo Beach Dog Rules.
• Westport Mom's 6th Annual Fall Festival- Sat 10/24, 10 -2PM, Gilbertie's Westport. Family fun for kids of all ages! Face Painting, Pumpkin Decorating, Costume Contest, Food Trucks & Music $25/Family
• Westport Country Playhouse - Ken Ludwig's Pride and Prejudice, Part 2: Napoleon at Pemberley. 10/20 - 11/7. · Westport Country Playhouse
• Earthplace Woodside Bash - Oct. 17th, 6-9PM. Earthplace's Annual Fundraiser Party. A fun night with great food and coktails. adults only. 10 Woodside Lane.
• Annual Westport Halloween Parade and Trick or Treating.Wed, Oct. 28th Downtown Westport. Parade starts on Main St. and ends at Veteran's Green with a Monster Mash Party. Kids up to age 8
• Westport Sunrise Rotary Hosts Westport Uncorked.Nov 5th, 6-9PM, The Inn at Longshore. Come for a wonderful night of great food and wine tasting at the newly renovated Longshore Inn. Every dollar supports important Westport charities.
• Southport Congregational 31st Annual Design Rooms with a View - This year's weekend event celebrates The Enduring Influence of British Design. Nov. 6th-8th
• Westport Public Library- Check the website for Oct. classes, events and activities for all ages
• Westport Farmer's Market - Thursdays 10am - 2 pm, 50 Imperial Ave., through Nov. 5th
• La Plague at Longshore Inn has reopened!
• New: Tremble Pilates - Downtown Westport
• hi'Amba - Just Opened for Brunch and lunch/Dinner coming soon!!- New Mediterranean Restaurant & Market from Award Winning Chef, Bill Taibe. 33 Jessup Rd
• The Chase - New bar/restaurant in Weston where Lunch Box was located.

OCTOBER TIP:

October is a great month to sell to buyers that need to move before year's end and a great time to buy from sellers that need to sell before year's end.

CLOSING THOUGHTS.....

Now that fall is officially here, Fairfield County remains a market of opportunity, but the results are increasingly property-specific. As we move further into the fall, local knowledge, thoughtful preparation and realistic pricing will make the difference. September cooled slightly from the summer pace but stayed competitive.

Sellers can still attract serious buyers with well-presented and correctly priced homes. An informed pricing strategy is crucial. Buyers have more choices with an increase in inventory but desirable properties can still sell quickly. Preparation and a clear understanding of market value remain essential.—and if you’re thinking about making a move, I can help you.

Not sure whether to sell now or wait? Let's run the numbers

Warmly,

Jillian

P.S. before you go...

"The only thing scarier in October than Halloween, is overpricing a home!"

TOP 1.5% OF REAL ESTATE PROFESSIONALS IN AMERICA

203-858.2095 | [email protected] | jillianklaffhomes.com