Tag Archives: KMS Team at Compass

Real Estate: A Multi-Generational Tale

For decades, suburban families have been stereotyped as a dad, mom and kids, in a house with a picket fence.

The picket fence has been replaced by a faux stone wall. Dad and mom may now live next door to a single parent, dad and dad, or mom and mom. 

There are other configurations too, like multi-generational housing. Today, our friends at KMS Team at Compass  — where at least one associate lives with her own parent — explore the trend.

We hear increasingly common requests these days about the need for multi-generational housing. This includes ADUs (accessory dwelling units), and homes with ample space within for privacy and independence.

The trend began during COVID. It continues for a variety of reasons, including the desire of grandparents to be part of grandchildrens’ lives (and the help they can provide for working parents); the difficulty young buyers face in finding homes in their budget, and more.

Two substantial multi-generational transactions were recently recorded in Westport.

Several Beachside Avenue properties (#120-122, 124-128 and 26) were purchased by an undisclosed buyer for their extended family.

128 Beachside Avenue: plenty of room for generations to share.

And the Kowalsky farm property at 109 Morningside Drive South was purchased by Marc Lasry, who may build homes for a few of his children on the property.

On a more standard level, we recently guided a mother, daughter and grandchildren into a new home in Westport. The search took us along many paths.

From the outset, we knew the property would need to offer an existing accessory dwelling unit (ADU), the ability to build one, or an in-law suite with enough separation to provide privacy for everyone.

This significantly narrowed the field, but we explored every viable option.

We even considered a new construction opportunity. While the home itself had potential, the location was not ideal, and the many decisions required when designing a home from the ground up quickly became overwhelming.

Our search refocused on homes that were complete, and ready to enjoy.

A new opportunity came on the market. We toured it that day. The home checked nearly every box.

It had been completely remodeled by the owner, meaning the property required no cosmetic updates or improvements.

Location was another key factor. The home is just minutes from the Westport train station, making commuting into the city convenient for her daughter.

It is also part of a small enclave of homes that share access to a pool, private dock and beach.

Having owned a home with a pool previously, the mother loved the idea of having pool access, without the responsibility of its maintenance.

Sitting on just over an acre, the property was another plus. There was room for the grandchildren to play, and it could easily accommodate an ADU. The builder had even drafted plans for one while considering it for his own use.

An ADU, designed by architect John Rountree.

Particularly intriguing was the space above the garage. The large, fully finished bedroomand bathroom provided an excellent foundation for a private living area.

Rather than building a separate ADU on the property, our client plans to expand this space to create a larger suite with its own living area and kitchen.

Westport is no longer a town filled almost only with parents and children. Multi-generational housing is one more piece of our changing demographics.

(“06880” regularly covers real estate trends — and everything else in town. If you enjoy stories like this, please click here to support our work. Thank you!)

Maida Webster and her husband (right) added a full addition to the home their adult children (left, with their own children) in 2017. The 3 generations enjoy proximity, but also privacy.

“Dual Representation” In Real Estate: What’s The Deal?

We sometimes hear real estate agents brag about “getting both sides of the deal” — meaning they represent both the buyer and seller in one transaction.

It sounds like they score twice the commission, for just a little extra work.

That may not show  the full picture. “06880” asked our friends at KMS Team at Compass about “dual representation.”

They said: “The listing agent has a considerably heftier lift — more time, more responsibility, more liability, and more room for misunderstanding.

“Representing both sides responsibly takes deep expertise, patience, and an unwavering commitment to ethics. Yet some sellers even manage to negotiate a lower overall commission rate, should the buyer come direct.

“Buyers may come directly to a listing — unrepresented — not out of manipulation, but because they feel empowered. They may have done a few online searches, think they can navigate the process themselves, and sometimes even expect a discount because ‘there’s no buyer’s agent involved.’

“Maybe they believe the process is simpler with fewer people involved.

This new construction on Dogwood Lane includes 6 bedrooms and 8 bathrooms. The 9,100-square foot home is listed for $10.65 million.

“From the listing agent’s perspective, these direct buyers usually come with a set of challenges. They may be less informed about market conditions, unfamiliar with the intricacies of the buying process, and suspicious that the listing agent is prioritizing the seller’s interests — which, of course, they are required to do (see our blog on agency relationships). This dynamic can create confusion and tension.

“When there’s no buyer’s agent in the mix, all the responsibilities of guiding, educating, and facilitating the buyer’s side don’t go away — they simply shift to the listing agent. Managing the timeline, addressing questions, coordinating with their attorney, lender, appraiser, inspectors, decorators, architects and even liaising with a condo board to complete detailed due diligence are all tasks that fall to the listing agent.

“In a properly balanced transaction, both the buyer and the seller have professional advocates. The buyer’s agent explains market context, strategizes around offers, financing, inspections and contingencies, helps manage overall expectations and makes sure crucial details aren’t missed. Meanwhile, the listing agent focuses on marketing and presenting the property, negotiating in their client’s best interest, and keeping the transaction on track.

“Both roles are separate, but equally crucial. Each agent helps streamline communication, protect their client’s interests, and reduce risk. Great deals happen when both sides are represented by skilled professionals who know their roles, respect the process, and work collaboratively toward a smooth closing.

“Because real estate transactions aren’t just about houses — they’re about people, emotions, and major life decisions.”

(“06880” reports regularly on the Westport real estate scene — and everything else in town. If you enjoy coverage like this, please click here to support our work. Thank you!)

“All-Cash” Real Estate Offers: What’s The Deal?

In this strong real estate market — with many properties selling above the asking price — we hear a lot about “all-cash offers.”

Is that true? Are they really all cash? Or are buyers seeking financing, but waiving any mortgage contingencies?  What does it mean for multiple-offer scenarios, which are common with most new listings?

We asked our friends at KMS Team at Compass. They say:

In a competitive market like Westport, cash offers can provide a distinct advantage. Sellers often prefer the certainty and speed of cash transactions, which can bypass the delays and contingencies tied to traditional mortgages.

According to SmartMLS, 56.5% of Westport’s 2025 buyers paid all cash.

But for most buyers, paying all cash upfront doesn’t mean they have the cash sitting idle. After all, the average price of Westport’s 2025 sales reported as cash purchases was $3.11 million.

This 5-bedroom, 7-bathroom, 6,050-square foot new construction on Owenoke is listed for $11.795 million. Will the buyer pay all cash?

So how does one come by all cash for a purchase?

While the KMS Team at Compass cannot provide investment advice, tax guidance or determine appropriate financing options for clients, we have seen many strategies in practice. These may be ideas to discuss with your financial advisor.

For those with significant assets in stocks and other investments, margin loans can be an intriguing option. By borrowing against the value of a portfolio without liquidating holdings, you may avoid triggering capital gains and preserve the potential for further market gains.

However, margin loans come with risk — the possibility of a margin call if the value of the portfolio declines. It’s a strategy that requires careful planning, and a strong stomach for market fluctuations.

The stock market rose in 2025. But that’s not always the case.

Another tactic is to “borrow” retirement resources. Presently, the IRS does not consider a withdrawal of funds taxable if the total amount withdrawn is replaced in the account within 60 days.

With proper timing and planning, funds can be repaid with proceeds from the sale of an existing home, or with money borrowed after closing.

After closing, buyers can access the equity in their home using several methods.

● Delayed financing: This requires purchasing the home with cash, and applying for a cash-out refinance immediately or within a few months.
● Home equity loan: A lump-sum loan, with fixed payments over time.
● Home equity line of credit (HELOC): A revolving line of credit, allowing you to borrow and repay as needed, similar to a credit card.

Others borrow, or are gifted, funds from relatives to purchase their home

So purchasing with “all cash” does not mean buyers tie up their capital indefinitely in real property. For some, it opens the door to strategic financing after the deal is done.

Many affluent buyers take a different approach to traditional 30-year fixed-rate mortgages. They may opt for interest-only loans,or other products that allow them to borrow at lower rates and keep their cash working, at a higher return, elsewhere. With the interest potentially deductible, the strategy becomes even more attractive.

Approximately 37% of Connecticut homeowners own their homes outright, with the percentage dropping to 23.6% for those homeowners of working age.

So yes: More than half of buyers strongly position their offers without financing contingencies to secure a home.

However, “cash” does not always mean cash.

And for those who can’t quite get there, many lenders have products that complete the underwriting process in advance and can present an actual loan commitment, subject only to property appraisal (if necessary) and homeowners insurance. This is as close to a cash offer as you can get.

(Speaking of which … you can support “06880” by credit card, check, PayPal, Venmo, or dropping off a bag of cash. Click here for the first 4 options; email us at 06880blog@gmail.com for the 5th!)

Buying Or Selling A Home? Realtors Offer “Wish List” Tips

As the new year begins, many people make “wish lists” for the coming 12 months.

(Others wish they had the time or energy to do so.)

Realtors are no different than you or me.

I asked the crack staff at KMS Team at Compass what they wished their clients would do. They said:

Home buyers

Speak with a mortgage broker, and get pre-approved for a purchase.

Select a trusted buyer agent, who has strong local knowledge and relationships to represent you.

If you plan to purchase with cash, have a “proof of funds” letter ready to go from a trusted advisor or investment counselor.

Evaluate your situation. Be clear about top priorities. and realistic goals and needs. Understand where you might have flexibility, or be willing to shift gears to break into this competitive market.

For some people, living directly on the water is non-negotiable. Others may be more flexible. (Photo/Jimmy Izzo)

Explore town websites. Speak to friends and acquaintances who already live and/or work in the area. What insider tips can they provide?

Spend a day exploring the town(s) you are thinking about. Drive through shopping areas and downtowns. Grab a coffee or drink. Eat there. Take a hike, walk the beach, visit the library, use a school playground, see what you think. How does it feel?

Start going to open houses. Familiarize yourself with the inventory. See how homes are presented and priced. Photographs are one thing; visiting the space, and walking though it, is another.

Ask your partner or agent team about private exclusives or pocket listings that have not yet been listed publicly.

Home owners

Tackle your maintenance to-do lists. Ordinary seasonal cleaning and repairs should never be left to the last minute.

Even if you are not thinking of listing in the short term, make the improvements now with a team you know. That includes:

  • Refinish floors
  • Update a kitchen or bathroom if needed (“new” is considered within the last 5-7 years)
  • Neutralize paint colors. to clean the palette and presentation
  • Have your roof evaluated. Replace poor shingles or repair entirely, if necessary.  This is a particular sticking point for insurance carriers today.
  • Have your attic and basement evaluated for mold and mildew.

Remove dead trees, branches or tired landscaping for a cleaner presentation; less is more. Consider maintenance-free options and evergreens that provide greenery and privacy year-round.

Dead trees can cause big damage. (Photo/David Pogue)

Evaluate your curb appeal. Does the driveway need resealing or repaving? How does the garage — especially if detached — complement the house? Are the garage doors in good shape, and work well?

Most importantly: Make needed improvements so you can enjoy them before you sell.

Home sellers

Declutter, declutter, declutter!

If you need help to get motivated or sorted out, hire an organizer..

Clean and purge all closets. Buyers will want to see space for their family to move into.

Pack things up now. You’ll have to move things eventually, so pack it up, donate it, and/or sell it!

Get a home inspection before listing. Address problems you may not know about.

Service mechanicals if they have not been examined within 12 months of listing.

Clean up the yard. Plant bulbs in the fall, flowers in spring.

Flowers add to curb appeal. (Photo/Patricia McMahon)

Wash windows, inside and out.

Clean gutters; make sure all downspouts are operational.

Fresh paint is the quickest refresh for the least amount of money

Hardwood floors in pristine condition are like gold. Show them off!

Hire a handyman to address annoying items that need fixing.

Paint the front door — first impressions are very important. Plant flowers, or put  planters at the front door.

Take photos in the fall, if you plan to list during the winter or early spring.

Swap out old light fixtures to make the house look more current, with updated styles. These do not have to be very expensive fixtures.

January was Radon Action Month. Did you have your house tested? Connecticut requires a reading of 4.0 or less.

(Not ready to buy or sell a home today? No problem. But you can click here, to make a tax-deductible contribution to “06880.” It’s also a good investment — and a lot cheaper.)

Real Estate 2025: A Very Good — But Tight — Year

2025 is in the books.

Real estate-wise, in many ways it was one for the books.

Our friends at KMS Team at Compass have compiled some stats. They show a robust market — particularly at the high end.

Last year, 1/3 of all MLS-marketed single-family homes surpassed $3 million.

Limited inventory at lower price points drove prices up. Homes in the $2 million to $2.99 million range sold for an average of 103.5% of their asking price.

Those listed between $1.4 million and $1.99 million fetched 104.5% of the asking price.

But MLS may not capture every sale. In the luxury sector, KMS Team says, the need for privacy and discretion often results in off-market transactions.

Those are not included in the reported figures. The firm expects a further rise in private offerings in 2026.

Five lots on Beachside Avenue — sold together to one buyer, for $54 million — was the largest sale in Westport last year. Or any year. The listing agent was Leslie Clarke Team at Compass.

Despite record-breaking sale prices, last year saw the lowest number of single-family home sales in a decade.

The median sale price — $2.3 million — was double that of 2019, and up 7% from the previous year. The average sale was $2,746,382 — up 10% from 2024.

The total number of reported transactions was 299, down 3% from 2024. The total volume was $821,168,364 — up 7% from the previous year — while the average price per square foot was $655.

The condo market experienced significant growth too, reaching an average sales price of $833 per square foot. KMS Team says that condo demand was driven largely by buyers seeking to downsize, or buy a second home in Westport.

Looking ahead, the realtors expect a modest increase in transaction volume in all types of properties, coupled with steady single-digit price growth.

The most expensive property currently listed is also on Beachside Avenue. The asking price for the 8-bed, 8 1/2-bathroo, 9,995-square foot home on 3.55 acres is $19.8 million.

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What about rentals?

Are you sitting down?

According to MLS, the highest monthly summer rental in 2025 was a fully furnished property on Fraser Lane. It could have been yours for only $78,000 a month, though someone else snatched it up.

Five other homes rented for between $45,000 and $48,000 a month during the summer season.

Three — on Soundview Drive, Bluewater Hill South and Spriteview Avenue — offered water views.

Of the 2 that did not, one on Weston Road — with a heated pool and pool house, and “exceptional” game room — carried an off-season rate of $19,000.

A property on Hitchcock Lane featured a 40-foot saltwater pool.

According to MLS, the most expensive unfurnished annual rental in Westport was on Woody Lane. Initially listed at $35,000 per month, it closed at $30,000.

The listing described it as an “outdoor paradise with exceptional grounds,” including a 44-foot pool; tennis, basketball and pickleball courts; an outdoor kitchen with a pizza oven, and a separate-entry apartment.

This 5-bedroom, 5 1/2-bathroom, 3,770-square foot house on Compo Cove was originally listed for rent at $60,000, for the month of August. The price dropped to $50,000 — but it was never rented.

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Weston, meanwhile, remains very appealing to buyers seeking more space, both inside and outdoors.

In 2025, the average acreage of properties sold in Weston was 2.25; in Westport it was 1.05.

Weston homes offered considerably more square footage in every price category: 12.6% larger in the $3 million-plus range, 38.8% bigger in the $2 million to $2.99 million category, and a whopping 60.8% larger in $1.4 million to $1.99 million.

Weston recorded 146 sales in 2025, up 8% from 2024. The median sale was $1.399 million, up 3.6%; the average sale ($1.530,901) was up 4.2%. The average price per square foot was $385.

In Weston, the upward trend in prices is slowing. KMS anticipates modest growth in 2026.

The most expensive property listed in Weston right now is this 5-bedroom, 7 1/2-bathroom, 11,450-square foot home, on 2.07 acres on Old Redding Road. The asking price is $3,999,999.

(Not ready to buy a home today? No problem. But you can click here, to make a tax-deductible contribution to “06880.” It’s also a good investment — and a lot cheaper.)

Roundup: “06880” House Tour & Stroll, Election Day Signs & Stats, Lynsey & Darcy …

Lovingly preserved homes and beautiful fall weather were the perfect combination for yesterday’s very educational, very high energy and very fun “Historic Homes of 06880” house tour.

Over 130 guests toured 2 properties on Greens Farms Road (both once owned by the Bedford family), and 2 other equally cool ones, on Long Lots Road and Wilton Road.

“06880” board members Dan Donovan and Bill Scheffler flank KMS Team at Compass members Mary Ellen Gallagher and Susan Seath, at 249 Greens Farms Road. Built by Edward T. Bedford, its interior is similar to the 1923 Westport YMCA building — which he endowed too.

Huge props to our friends at KMS Team at Compass, who helped organize the event, and provided historical background and other materials; Pat Shea of Coldwell Banker, who is involved with one of the Bedford homes, and the “06880” board of directors, who greeted visitors warmly and offered additional insights.

In a town filled with new construction, residents love to take a peek into homes that have stood for a century or two. There are many around — and we’ll show off 4 more great ones next year.

Totney and Rick Benson, admiring the Prohibition Era-bar at 209 Wilton Road. The young owners have renovated it with an eye toward its 155-year-old history.

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And speaking of “06880” activities: The 5th annual Holiday Stroll returns Saturday, December 6!

From 4 to 7 p.m., the Westport Downtown Association and “06880” present a now-traditional, action-packed and family-friendly kickoff to the holidays.

The Orphenians will sing. Santa and other characters will pose for photos. There’s a DJ, face painting, food, special deals for shoppers, and much more — including a dedication of the new WDA clock.

More details coming soon. But for now: Save the date!

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Tomorrow is Election Day. (Polls are open from 6 a.m. to 8 p.m. Click here for information on candidates and polling places.)

Which means that on Wednesday, thousands of yard signs will be obsolete.

Most candidates do a good job of removing them, within the 48 hours required by law.

But what next?

Representative Town Meeting (RTM) members recycle theirs. Many run every 2 years; it’s a non-partisan body, so their signs just say their name and district.

Yet the signs for those running for boards and commissions — often on a ticket with others — are instantly outdated.

They might save the metal stands. The signs themselves are destined for landfill.

Unless someone has a better idea.

Can artwork be created, perhaps as a school project? Is there another use for them?

I have no idea. But “06880” can start a good discussion.

If you know a good use for thousands of suddenly useless yard signs, click “Comments” below.

Yard signs near the transfer station. Is that where they will all end up? (Photo/Matt Murray)

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Speaking of the election: Early voting ended yesterday. It was the first time in Connecticut, for local races.

After 2 weeks, 16.7% — 3,177 out of 19,020 eligible Westport voters — cast ballots.

The breakdown:

  • Democrats: 1,772 of 7,945 eligible voters (22.30%)
  • Republicans: 488 of 3,332 eligible voters (14.65%)
  • Unaffiliated: 899 of 7,588 eligible voters (11.85%)

Of course, how they voted will not be known until tomorrow night. “06880” will have the results when they are announced, some time after 8 p.m.

Lucia Scotti (left) came home yesterday from the University of Connecticut, to vote at Town Hall. She was joined by her parents, Janine and Pietro.

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Pulitzer Prize-winning journalist (and 1991 Staples High School graduate) Lysney Addario’s new film, “Love+War” — a documentary about her work in conflicts around the globe — has gotten great reviews.

On “Weekend Edition,” she spoke with NPR’s Ayesha Rascoe about the balance between her work and life. Click here to read the interview, and/or to listen. (Hat tip: Dick Lowenstein)

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The Westport Book Shop’s guest exhibitor this month is well-known artist Darcy Hicks.

Specializing in metal leaf and oil paint, she is drawn to anything that reflects aggressive light.

Hicks is the director of education at the Norwalk Art Space, which provides free art and music education to low-income students. The Westport native earned a bachelor’s in fine arts from Smith College, a master’s of education from Lesley University, and an MFA in creative writing from Fairfield University.

A reception is set for November 12 (6 p.m.). All artwork on display is available for purchase. 25% of the proceeds will be donated to the Arbor Day Foundation, which has planted half a billion trees.

Darcy Hicks, with her work at the Westport Book Shop.

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Veterans Green was packed yesterday with air-cooled car owners, their admirers — and of course, the vehicles themselves.

The 12th annual event was sponsored by the Small Car Company,

Some of the many air-cooled cars on Veterans Green. (Photo/Susan Garment)

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Drivers taking advantage of this train station spot are going to have to wait a lot longer than 15 minutes.

(Photo/John McCarthy)

Donut Crazy closed in April.

But in terms of outdated signs, this one has nothing on Jesup Green.

A sign there indicated a Minnybus stop.

Nearly 40 years after the diesel bus made its last run.

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Get your game on!

SLOBs — the Staples Service League of Boys, a hard-working and very popular organization — hosts a 3-v-3 basketball fundraiser. Proceeds go to Staples Tuition Grants — a very worthy cause for the teens — in memory of their friend Perrin Delorey.

The November 21 event (6 p.m.) includes pizza. Registration is $25 per participant; Venmo @jhgillman.

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Jeff Lea — the winningest coach in Staples boys soccer history — has just won again.

The 2nd permanent head coach — who served in 1970, then from 1978 to 2002, and won 5 state championships plus 12 FCIAC titles en route to a 357-77-42 record — will be inducted on March 7, at the Doubletree in Bristol.

Lea’s selection brings to 12 the number of Connecticut Soccer Hall of Fame inductees with Staples ties. They include Loeffler, Steve Baumann, Paul Hunter, Tim Hunter, Jim Kuhlmann, Kyle Martino, Ken Murphy, Kevin Murphy, Mark Noonan, Mike Noonan and Dan Woog.

Jeff Lea (far left), with members of the 1970 state championship team (from left): Tracy McIntosh, Fred Cantor, Neil Brickley, Steve McCoy.

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Josie McAllister took advantage of yesterday’s spectacular autumn weather to enjoy the Compo Beach jetty.

Her human friend Gwen Tutun was happy to record the moment, for “06880”‘s daily “Westport … Naturally” feature.

(Photo/Gwen Tutun)

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And finally … that early darkness yesterday caught you by surprise, right?

It happens every year, when Daylight Savings ends justlikethat.

But don’t worry. Only 125 days until it begins again.

(“06880” is more than just a blog. We sponsor an annual house tours, 2 strolls a year, and a variety of good causes. But we can’t do it without you! Please click here to support our work. Thank you!)

Sunday’s “Historic Homes Of 06880” Tour Almost Sold Out

Only a few tickets remain for the 3rd annual “Historic Homes of 06880” house tour. This Sunday’s event (November 2, 1 to 4 p.m.) includes 4 very cool (and different) homes.

Tickets are $60 each, $100 for 2. Proceeds help fund “06880”‘s work — which, as always, chronicles Westport’s past, present and future.

Click here for tickets — and read on! Our friends at KMS Team at Compass once again co-sponsor the tour.

249 Greens Farms Road

The house was built in 1907 by Charles Bedford, president of the Vacuum Oil Company and son of wealthy businessman Edward T. Bedford. (A second Bedford house on Greens Farms Road is also on this year’s house tour. See below for details.)

Charles married Happy Briggs, and sold the property  to Michael Hawie in 1920.  The property was sold to multiple people until the current owners purchased the property. The home is on the market, listed by KMS Team at Compass.

A veranda, rear porch and several balconies offer views of the expansive grounds, and luxurious pool. It’s a great example of Westport’s Victorian-style homes.

Plus, it’s just steps away from another home on our 3rd annual tour:

.221 Greens Farms Road

Edward T. Bedford — the businessman and philanthropist who endowed the Westport YMCA and Bedford Elementary School, among many other gifts — built the Colonial Revival in 1904 to replace a Federal house that burned. His son Frederick owned it until his death. His daughter Ruth Bedford lived there from 1950 to 1963. When she died a decade ago, her $120 million estate was divided between the Westport Y, Norwalk Hospital and the Foxcroft School.

The Colonial Revival style reflects the finest quality work of the period.  Architectural details include a conical tower with a Palladian window. The home is on the market, listed by Coldwell Banker.

209 Wilton Road

Known as the Nathaniel S. Kirk House, this circa 1870 antique was expanded in 1900, 1930 and 1989. Many may not even know it exists, behind the perimeter fencing. A quick glance shows only the old well.

The current owners have worked tirelessly for nearly 5 years to add their own touch. Original fireplaces, wide board flooring and beams help retain the character and charm of this Connecticut classic. A beautifully paneled family room and incredible Prohibition Era bar room often have guests staying well past their welcome.

155 Long Lots Road

This beautiful, somewhat humble 1938 Cape Cod-style home has been expanded more than once over time, by previous owners.

The current owners have created more natural light, and a more open floor plan, with exposed beams. There is a wonderful loft space above the barn-style garage. Think “Easthampton meets Westport.”

Outdoor amenities include a pool and tennis court (recently transformed into a pickleball magnet).

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“06880” often celebrates Westport’s rich history. We honor homeowners who preserve the past, while enhancing their neighborhoods — and those who bring new life to them.

“06880” tells stories. As you explore all 4 houses, you’ll learn the stories behind each one.

The homeowners will point out cool aspects of each home. You’ll get a brochure explaining the 4 houses too.

Our friends at KMS Team at Compass are once again sponsoring the “Historic Homes of 06880” tour.

Tickets are $60 each, $100 for 2. Proceeds help fund “06880”‘s work — which, as always, chronicles Westport’s past, present and future.

Click here for tickets. Questions? Email 06880blog@gmail.com

Old Homes, New Sales Data

As we prepare for the 3rd annual “Historic Homes of “06880” tour next Sunday (November 2, 1 to 4 p.m.) — featuring 4 homes, all built between 1870 and 1938 — it’s interesting to take a look at the ages of all the homes sold in Westport thus far in 2025.

Exactly 1/3 (33.4%) of the 243 homes that changed hands were built between 1950 and 1970. 15.7% were built between 1900-1950, while 5% went up before 1900!

In other words, more than half the homes sold were built in 1970 or earlier, while just 18.6% of homes sold were built in 2010 or later.

The 4 homes on the Historic Tour date from 1870, 1904, 1907 and 1938. Each is an excellent representation of its time period. All have been restored with loving care — and enlarged to meet 21st century needs.

249 Greens Farms Road, a Bedford family gem.

Homes built in the 1920s housed an average of 4.3 people, and were approximately 1,000 square feet.

By 2014 — nearly 100 years later — home sizes had increased roughly 2 1/2 times, to an average of 2,650 square feet.

The average size of homes sold year to date in Westport is 3,851 square feet (above grade). The median size is 3,378 sf.

Homes priced in the $1.4 to $2 million dollar range remain the most sought after, deriving an average sales price of 5.5% over asking price. Homes in this price range average 2,848 square feet.

Hover over or click on to enlarge.

This information comes from our friends at KMS Team at Compass — sponsors of our November 2 Historic Homes tour.

They’ll be with “06880” representatives in the 4 homes next Sunday, ready to describe the history of each property, and answer questions about how “old” homes have been adapted for 21st century life.

To learn more about those 4 homes — 221 and 249 Greens Farms Road, both built by the legendary Bedford family, as well as 209 Wilton Road and and 155 Long Lots Road, and for tickets, click here.

155 Long Lots Road

New Addition To “Historic Homes Of 06880” Tour!

A fourth home has been added to our November 2 “Historic Homes of 06880” tour.

And it’s a beauty.

249 Greens Farms Road replaces a home on Compo Road South. The owner had to drop out, because of an illness in the family.

Our addition — the Greens Farms Road home — is a 1907 estate. It combines historic character, architectural details and modern comfort across 4 levels.

249 Greens Farms Road

The house was built in 1907 by Charles Bedford, president of the Vacuum Oil Company and son of wealthy businessman Edward T. Bedford. (A second Bedford house on Greens Farms Road is also on this year’s house tour. See below for details.)

Charles married Happy Briggs, and sold the property  to Michael Hawie in 1920.  The property was sold to multiple people until the current owners purchased the property. The home is on the market, listed by KMS Team at Compass.

A veranda, rear porch and several balconies offer views of the expansive grounds, and luxurious pool. It’s a great example of Westport’s Victorian-style homes.

Plus, it’s just steps away from another home on our 3rd annual tour:

.221 Greens Farms Road

Frederick Bedford built the Colonial Revival in 1904 to replace a Federal house that burned. His son, Edward T. Bedford — the businessman and philanthropist who endowed the Westport YMCA and Bedford Elementary School, among many other gifts — owned it until his death in 1931. His daughter Ruth Bedford lived there from 1950 to 1963. When she died a decade ago, her $120 million estate was divided between the Westport Y, Norwalk Hospital and the Foxcroft School.

The Colonial Revival style reflects the finest quality work of the period.  Architectural details include a conical tower with a Palladian window. The home is on the market, listed by Coldwell Banker.

Click here for tickets — and read on!

The other homes — announced previously — are:

209 Wilton Road

Known as the Nathaniel S. Kirk House, this circa 1870 antique was expanded in 1900, 1930 and 1989. Many may not even know it exists, behind the perimeter fencing. A quick glance shows only the old well.

The current owners have worked tirelessly for nearly 5 years to add their own touch. Original fireplaces, wide board flooring and beams help retain the character and charm of this Connecticut classic. A beautifully paneled family room and incredible Prohibition Era bar room often have guests staying well past their welcome.

155 Long Lots Road

This beautiful, somewhat humble 1938 Cape Cod-style home has been expanded more than once over time, by previous owners.

The current owners have created more natural light, and a more open floor plan, with exposed beams. There is a wonderful loft space above the barn-style garage. Think “Easthampton meets Westport.”

Outdoor amenities include a pool and tennis court (recently transformed into a pickleball magnet).

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“06880” often celebrates Westport’s rich history. We honor homeowners who preserve the past, while enhancing their neighborhoods — and those who bring new life to them.

“06880” tells stories. As you explore all 4 houses, you’ll learn the stories behind each one.

The homeowners will point out cool aspects of each home. You’ll get a brochure explaining the 4 houses too.

Our friends at KMS Team at Compass are once again sponsoring the “Historic Homes of 06880” tour.

Tickets are $60 each, $100 for 2. Proceeds help fund “06880”‘s work — which, as always, chronicles Westport’s past, present and future.

Click here for tickets. Questions? Email 06880blog@gmail.com

4th House Added To “Historic Homes Of 06880” Tour

A fourth home has been added to the 3rd annual “Historic Homes of 06880” tour.

And it’s very cool.

221 Greens Farms Road — rounds out the quartet, for the Sunday, November 2 (1 to 4 p.m.) event.

 

221 Greens Farms Road

Frederick Bedford built the Colonial Revival in 1904 to replace a Federal house that burned. His son, Edward T. Bedford — the businessman and philanthropist who endowed the Westport YMCA and Bedford Elementary School, among many other gifts — owned it until his death in 1931. His daughter Ruth Bedford lived there from 1950 to 1963. When she died a decade ago, her $120 million estate was divided between the Westport Y, Norwalk Hospital and the Foxcroft School.

The Colonial Revival style reflects the finest quality work of the period.  Architectural details include a conical tower with a Palladian window.

The other homes — announced previously — are:

209 Wilton Road

Known as the Nathaniel S. Kirk House, this circa 1870 antique was expanded in 1900, 1930 and 1989. Many may not even know it exists, behind the perimeter fencing. A quick glance shows only the old well.

The current owners have worked tirelessly for nearly 5 years to add their own touch. Original fireplaces, wide board flooring and beams help retain the character and charm of this Connecticut classic. A beautifully paneled family room and incredible Prohibition Era bar room often have guests staying well past their welcome.

123 Compo Road South (corner of Green Acre Lane)

The David Flynn House (circa 1853) is a pristine, updated 19th century gem. The current owner has taken the prior owners’ restoration even further, combining compelling cosmetic changes with gorgeous antique and contemporary furnishings.

Three working fireplaces are often in use. The heated stone floor in the family room is perfect for stocking feet. The stunning country kitchen opens to a bluestone terrace, small pool and magnificent gardents.

The bonus is a separate 2-car garage, built to look like an original barn, with furnished living space above it.

155 Long Lots Road

This beautiful, somewhat humble 1938 Cape Cod-style home has been expanded more than once over time, by previous owners.

The current owners have created more natural light, and a more open floor plan, with exposed beams. There is a wonderful loft space above the barn-style garage. Think “Easthampton meets Westport.”

Outdoor amenities include a pool and tennis court (recently transformed into a pickleball magnet).

==================================================

“06880” often celebrates Westport’s rich history. We honor homeowners who preserve the past, while enhancing their neighborhoods — and those who bring new life to them.

“06880” tells stories. As you explore all 4 houses, you’ll learn the stories behind each one.

The homeowners will point out cool aspects of each home. You’ll get a brochure explaining the 4 houses too.

Our friends at KMS Team at Compass are once again sponsoring the “Historic Homes of 06880” tour. The Bedford home is on the market, by Coldwell Banker.

Tickets are $60 each, $100 for 2. Proceeds help fund “06880”‘s work — which, as always, chronicles Westport’s past, present and future.

Click here for tickets. Questions? Email 06880blog@gmail.com