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from my desk to your door...
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Hello,
October has arrived, and what a beautiful start to fall it has been here in Westport! The air is crisp, the leaves are starting to turn, and yet we’ve been treated to stretches of sunshine that still feel like summer (and some spectacular sunsets)! While the weather may be lingering in between seasons, the reality of busy fall schedules is in full swing, with school routines, work commitments, and even college kids already returning home for their first fall breaks. Halloween is just around the corner, quickly followed by the holiday season that always seems to arrive faster than we expect.
Here in the local real estate market, activity has remained steady. Well-priced homes continue to attract significant attention, particularly those that highlight Westport’s lifestyle appeal and have close proximity to schools, beaches, and other vibrant town amenities. Inventory is still on the lean side, which has kept sellers in a strong position, while motivated buyers are moving quickly when the right home comes along.
If you’ve been thinking about selling, fall is a wonderful time to showcase your home against the backdrop of Westport’s autumn beauty. Buyers bring well-prepared and ready to act can make all the difference in securing the perfect property before year’s end.
As always, I’m here to provide insight, guidance, and support to help you achieve your real estate goals this fall, during the holidays, or in the year ahead. Whether you’re thinking about making a move soon or are simply curious about the value of your home, I’d love to be a resource. Let’s talk about how I can help you navigate the market with confidence and ease every step of the way, including getting your house ready for market. CALL ME NOW! Follow me at jillian.klaff.realtor on instagram for my latest listings and real estate tips.
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from our blog
NEIGHBORHOOD AMENITIES THAT INCREASE HOME VALUE When it comes to home values, neighborhood amenities play a crucial role. Buyers prioritize quality-of-life factors that extend beyond the home’s walls. Westport, CT, a desirable community known for its affluent neighborhoods, great schools, and easy access to New York City, highlights the importance of community amenities. Understanding which amenities increase home value can help homeowners make informed decisions when purchasing a property or investing in upgrades. Here’s a look at the top amenities that attract buyers and positively impact home values in Westport and similar high-demand communities. READ MORE.
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october opportunities
BACK ON THE BEACH! - From October 1st through March 31st, dogs are permitted in the designated off-leash area, which is located south of the brick bathhouses.
WESTPORT UNCORKED - 10/16 - Westport Sunrise Rotary’s 38th Annual WINE TASTING> The Inn at Longshore. Tickets
ARTISTS OF NORWALK HOUSE TOUR - 10/19 - A guided bus tour that will take you inside the artists’ homes who helped shape Norwalk’s rich creative heritage!
WESTPORT/WESTON YMCA FAMILY HALLOWEEN SPOOKTACULAR - 10/18, 3-5pm Pony rides, pumpkin decorating, bounce houses, a petting zoo, arts & crafts, lawn games, food trucks, and plenty of candy & popcorn with a parade
WESTPORT COUNTRY PLAYHOUSE - Get your tickets for all the great performances this fall.
WESTPORT DOWNTOWN HALOWEEN - Recommended for children up to age 8. Children may trick or treat along Main Street and in Town Hall. 10/29 Raindate 10/30
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5 Maplegrove Ave
5 BD | 2.5 BA | 2856 SF
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29 Woods Grove Rd
4BD | 3BA | 2279SF
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9-A Ludlow Road
2BD | 2.5BA |1150SF
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56 Wright St
5 BD | 3 BA | 3450 SF
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206 Good Hill Road, Weston
5 BD | 4 BA | 3149SF
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7 Dawn Drive
6 BD | 8BA | 8641 SF
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461 Tahmore Dr, Fairfield | 3BD, 3BA, 2612SF
UC 5 | Close 13 | Multiple Over Offers
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We have even more exciting new listings on the way! Go to jillianklaffhomes.com and check our listings tab on our website for updates and details. Stay tuned to my instagram jillian.klaff.realtor and come on over to my website to see what I have going on!
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The Westport real estate market reflects a tight inventory with only a 2.16 month supply, highlighting a competitive market for buyers and a strong seller’s market where demand outpaces supply. Recent data reveals a 14% decline in inventory over the past month and a significant 30% over the last year. This reduced supply may lead to swifter decision-making processes for potential homebuyers, as properties are less abundant.
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In September 2025, there were 51 new listings, with a median list price of $2,195,000.
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The active listings stand at 100, with a higher median price of $2,972,500.These figures indicate that while new listings are being added, the overall market is skewed towards higher-priced homes, reflective of Westport’s premium real estate market.
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Currently, there are 66 new pending listings at a median list price of $2,249,000, with homes spending a median of 88 days on the market before going pending.
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The median sold price is recorded at $1,800,000 with a significant -29% month-over-month change. Homes are selling with a median of 47 days on the market, and the sold to list price ratio stands at 100.84% slightly down by -2% month-over-month. This data suggests a competitive market where homes are sold close to their list prices, but with a noteworthy decrease in the median sold price, possibly indicating opportunities for buyers to find value.
The current market conditions in Westport, with its reduced inventory and competitive pricing, provide a unique opportunity for proactive buyers who are ready to act decisively. The high median prices reflect the desirability of the area, but the slight dip in median sold prices and slight flexibility in sold-to-list price ratios might be an opportunity for buyers to negotiate, particularly move-up buyers looking to leverage their existing equity.
Despite a 29% month over month decrease in median sold price, sellers have a promising opportunity with the 66 new pending listings at a median price of $2,249,000 allowing them to take a strategic approach to pricing and presentation by positioning their homes competitively and showcasing them by enhancing curb appeal and interior aesthetics to capture buyers’ attention quickly. Professional staging and high quality photography can make a significant difference in how a home is perceived.
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I’m truly honored to be recognized as a Five Star Real Estate Agent for the third time. This award reflects my commitment to providing exceptional service, expert guidance, and trusted results for every client I have the privilege to represent. I’m so proud to serve the Westport community and grateful to my clients, colleagues, and the Coldwell Banker team for their continued support and confidence.
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It’s hard to believe we’re already in October—one of my favorite times of year in Westport! The pumpkins are out, porches are glowing, and there’s that unmistakable mix of excitement and coziness in the air as we head toward Halloween and the start of the holiday season.
I’ve loved seeing the community come alive with fall festivities, from the colorful foliage and Octoberfests to the ghosts and goblins decorating the lawns. It’s a wonderful reminder of what makes Westport such a special place to call home—our sense of connection, warmth, and community spirit.
As we move toward the close of the year, it’s also a great moment to think ahead. Whether you’re considering a move before the holidays or planning for 2026, I’d be happy to discuss how to make the most of current market opportunities and position you for success.
Please take a look at my new listing at 3 Hickory Hill Road In Westport on my website for 3 Hickory Hill Road in Westport. Check out the FLIPBOOK too. It's a fabulous new construction project and I think you'll love it!
And keep in mind, If you’re considering selling, buying, or just curious about today’s market, I’d love to connect—let’s talk about how I can help you make the most of this exciting season. I have the real hard facts for really smart moves!
Have a safe and happy Halloween and get take a breath before the holidays are here!
Jillian
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jillian klaff online resources
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Social Media Everyday, we are actively sharing and engaging on our social media platforms to attract active buyers and local sellers. Join us on Instagram, Facebook, YouTube, or LinkedIn to stay informed about local market trends, view our latest listings, and learn more about the Westport community.
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JILLIAN KLAFF | TOP PRODUCER CB GLOBAL LUXURY
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