Tag Archives: KMS Team at Compass

“06880” Historic Homes Tour Returns November 1

Posted on September 30, 2026 | Leave a comment

Westport is a town of teardowns and new construction.

“06880” reports often on both.

But there are still plenty of historic homes. For decades — centuries, even — owners have cared for them lovingly, restored them beautifully, and adapted them to today’s life.

On Sunday, November 1 (12 noon to 4 p.m.)., you can tour 5 of Westport’s most classic — and coolest — houses.

Our 4th annual “Historic Homes of 06880” tour — presented with our friends at KMS Team at Compass — is our most impressive yet.

We’ve added a 5th home to our usual 4. We added an extra hour too.

We’ve found 5 remarkable properties — from Greens Farms and Long Lots to Compo and Old Hill — that will prove that history lives, architecture is stunning, and our neighbors are very creative folks.

As you explore all 5 houses, you’ll learn the stories behind each one. Homeowners and docents will point out highlights of each home. You’ll get a brochure giving added background and info too.

Tickets are $75 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.

And now … 2026’s “5 Historic Homes of 06880.”

311 Greens Farms Road

This house was built in 1790 by Peter Jennings. It passed later to Edwin Jennings, the first commercial greenhouse owner in Green’s Farms, known nationally for his pansies. It was the home of 4 generations of that family for more than 150 years, until its sale in 1948.

A later owner, Allan Pifer, was president of the Carnegie Corporation. He renovated the handsome fireplaces.

The present owners purchased the home in 2018. Working with Rocco DiLeo, they added an addition, connected by a narrow wing that includes the 14-inch white pine floorboards in the original home. Upstate they found reclaimed exposed timbers, complementing the post and beam timbers in the original home.

The owners were extremely conscientious, restoring almost every aspect of the home. With all original details replicated — including gas sconces — the architecture, scope and warm charm is enhanced throughout.

Moving from the lovingly maintained original portion, into the well-designed addition, highlights the seamless blend of 1790 and 2026 life.

311 Greens Farms Road

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50 Turkey Hill Road North

One of the most recognizable houses in Westport — on the Turkey Hill North/Long Lots Road corner, opposite St. Luke Church — this was built between 1788 and 1799. by the famous Burr family.

It was an inn and tavern, then given as a wedding present by Daniel Burr to his son Jonathan and his bride. It passed later into the equally famous Banks family, who owned it through 1920, and served for a while as a farm.

The current owners have restored other antique homes. They fell in love with the scale of the house. They renovated the oversized kitchen (originally a barn/shed for crops). The post and beam architecture is spectacular; the pine floors are original.

Fireplaces throughout are reminders of the days when they warmed the entire home. The one in the dining room features a very rare wood lintel. There are 7 bedrooms.

Outside, the current owners restored stone walls. Perennial gardens have bordered the property since the 1920s.

In back, the 19th century barn was redesigned as space for the owners’ parents.

50 Turkey Hill Road North

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50 Sylvan Road North

History bursts from every part of this 3-acre property.

The Tudor Revival was built by Charles Cutler more than a century ago for the president of Dun & Bradstreet. He designed (among others) the Patagonia building downtown (now the Compass office), and Greens Farms Elementary School.

Previous owners include actor Frank Gorshin (The Riddler on “Batman”), and billionaire Marc Lasry. The current owners have spent 3 years restoring the home and the grounds.

The stone walls are 2 feet thick. The 9 bedrooms and 8 bathrooms include carvings of Latin sayings and animals. There is even a room where the chauffeur could pull in and wait (he was not allowed anywhere else).

The grounds are as magnificent as the interior. Landscape architects Beate Hochman and Emilio Mandujano discovered and resurrected long-lost gardens, statues and fountains. A new farm building includes chickens and ducks, with a koi pond nearby.

50 Sylvan Road North

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56 Sylvan Road North

The “9 Hearths House” was built around 1791 by Noah Nash. (Fun fact: It actually has 11 hearths.) A famous later occupant was Daniel Webster. While living there, he created Westport’s Minute Man monument.

But Nash and Webster are not the only famous names to own this special property. The current owners are Mo and Jen Tooker — she is Westport’s former 1st selectwoman, now running for state comptroller.

Original wide wood plank floors and ceiling beams remain throughout the oldest section of the house (now the main living area). A mudroom and breakfast room were added in 2013.

The Colonial Revival received a Historic District Commission Preservation Award in 2014, for “meticulous care of the property.” Living space has been updated for a modern family, while the antique character of the house is felt everywhere.

56 Sylvan Road North

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217 Compo Road South

This home was built in 1855 by Rufus Bennett. His family dates back to the Revolutionary War; they watched the British march by on their way Danbury. It passed into the hands of Rufus Wakeman, a member of another famous Westport family.

In 2002 the house was saved from demolition. Realtor Jill O’Shea spent years fully restoring it. The current owners have re-designed this Victorian farmhouse, making it work well for themselves and their 2 young children.

Highlights include chestnut flooring, an exposed brick fireplace, a custom kitchen, gas lanterns, front porch and bluestone patio with a fire pit, enclosed by mature specimen trees and a perennial garden.

It is a great example of a home that’s a true antique outside, while inside it supports a modern lifestyle. The interior maximizes well-laid out, compact space. Hidden storage is key.

The current owners also renovated a carriage house/detached garage into a fully compliant accessory dwelling unit. It too is on display, as a thoughtful modern use of historic space.

217 Compo Road South

(Tickets are $75 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.)

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Roundup: Flood & Erosion Board, Historic Homes Tour, Home Heating Help …

Posted on September 23, 2026 | Leave a comment

When the Flood & Erosion Control Board meets October 7 (7:30 p.m., Zoom), the first agenda item will be the biggest.

Both physically. and in terms of town impact.

Members will hear an application to subdivide the property at 55-57 Greens Farms Road, to demolish an existing office building and replace it with a 250-unit housing development. The proposed activity is within the waterway protection line area of Pussy Willow Brook.

Meeting materials have not yet been posted on the town website.

Plan for “The Fitzgerald” (lower center, which would replace an existing office building. A pond, fountain and other waterways are shown in blue.

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The “06880” Historic Homes Tour is back — and bigger than ever.

By which we mean: This year, we’re adding a 5th home to the annual look-at-Westport’s-amazing-heritage event.

With our friends from KMS Team at Compass, we’ve put together 5 amazing homes.

All have been around for decades — even centuries.

All have been lovingly maintained.

And all are as remarkable inside as out.

We’ll roll out the big reveal next week. But right now, save the date: Sunday, November 1, from 1 to 4 p.m.

See you on the tour!

This house was on a previous “06880” Historic Homes tour. This year, we’ve got 5 very intriguing new — as in “old” — ones.

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Worried about paying for this winter’s heat?

Applications for the Connecticut Energy Assistance Program (CEAP) open October 1.

Westport residents can apply through the Department of Human Services by confidential appointment only. Calll 203-341-1050 or email humansrv@westportct.gov. Home visits are available for homebound residents. Returning applicants will receive instructions by mail.

Eligibility may be established if your household receives SNAP, TANF, SSI, qualifying means-tested Veteran’s benefits or other qualifying benefits, or if your gross annual household income is at or below 60% of Connecticut’s State Median Income (SMI).

The maximum annual income ranges from $48,714 for a 1-person household, to $129,279 for 8.

Residents who heat with oil or propane are encouraged to apply early in the heating season to help ensure they receive the full benefit for which they qualify.

For more information, click here.

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Put money in the pot.

Gat a pot.

That’s the idea of Pippa Bell Ader’s 2nd annual fundraiser.

Set for a week from tomorrow (Thursday, October 1, 10 a.m. to 2 p.m.), it’s a chance for Westport Farmers’ Market shoppers to donate to the Green Village Initiative. The Bridgeport-based (and Westport-born) gardening, farming, sustainability, education and advocacy non-profit

Donors receive in return a homemade pot. Perfect for — of course — growing something, and keeping the circle of life alive.

Last year’s Pippa’s (and Friends) Pots event raised over $1,600. Let’s blow past that this year!

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Planning on getting married?

Not so fast!

Sal Liccione — a Westport justice of the peace — notes that as of October 1, there will be a minimum 48-hour waiting period from a time the couple completes their marriage license application in the Town Clerk’s office where the marriage ceremony will take place, until they can be issued their license.

In addition, the marriage license will now be valid for 65 days from the date it is handled to the couple.

Longshore is a popular spot for Westport weddings. The rainbow is extra. (Photo/David Dellinger)

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It happens a lot more rarely than a Cribari Bridge opening.

But when the railroad bridge over the Saugatuck River, a few yards south, opens for maintenance, it’s always an impressive sight.

It tilted upward yesterday, to allow a barge with a large crane underneath. Jonathan Alloy caught the action.

(Photo/Jonathan Alloy)

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he Westport Rotary Club had 2 featured speakers yesterday.

Dr. Scott Kellermann, founder of the Bwindi Hospital in Buhoma, Uganda described its growth to become one of the best hospitals in East Africa. Westport Rotarians have provided substantial assistance since 2009.

Sara Kempner, director of creative campaigns and collaborations at the US Vote Foundation, spoke about her nonpartisan organization that educates people on the logistics of voting in every state. A recent campaign involved placing a QR code linked to voter registration on pizza boxes.

Dr. Scott Kellermann shows Westport Rotarians in Uganda. (Photo/Alec Foege)

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Nature can be both beautiful and vicious. Today’s “Westport … Naturally” image shows both. Photographer Jamie Walsh calls it “the web of life.”

(Photo/Jamie Walsh)

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And finally … in honor of Connecticut’s new wedding laws (item above):

(If you’re not getting married — and have, say 20 seconds to spare – please click here to support this hyper-local blog. And you don’t even have to get us a present. Thank you!)

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Maintenance Is Preservation: Homeowners Can Help Prevent Teardowns

Posted on September 5, 2026 | 13 comments

Every Monday, “06880” features 4 “Then & Now” homes: one that was torn down, and the home that replaced it.

There are many reasons why new owners opt for new construction. The house they bought may not fit their needs. It may be too small, architecturally outdated, or lacking modern amenities.

But there’s another reason: It was not maintained well.

For sellers who hope their home survives the wrecking ball, that’s one variable they can control.

Our friends at KMS Team at Compass know all about maintaining a home. They say:

Westport’s teardown issue isn’t just about developers. Deferred maintenance plays a role, too.

Plenty of buyers appreciate older homes, and see them as a more affordable way into town. But when years of deferred maintenance add up, renovating may no longer make financial sense, and the value shifts to the land.

Taking care of our older homes helps preserve the character of Westport, and gives the next buyer a reason to renovate rather than tear down.

Maintenance is preservation.  Homeowners who consistently care for the fundamentals of an older home give future buyers the option to renovate and preserve it, rather than making the land itself the property’s greatest value. The goal is not to make an older home new. It is to keep it healthy.

This 1939 River Lane home has been expanded to 6 bedrooms. Its architectural details have been well maintained.

Maintaining a home does not mean constantly renovating it, or having the latest kitchen and bathrooms. It means taking care of the bones of the house — the roof, foundation, drainage, electrical, plumbing, heating and cooling systems, chimney, septic or sewer connection, and environmental and safety issues.

Cosmetic updates are relatively easy for a buyer to envision. What can become overwhelming is a house with years of deferred maintenance. An older kitchen can be charming; a failing roof, water intrusion, outdated electrical system and neglected mechanicals are much harder to overlook.

Buyers are much more willing to work with an older home when they believe the underlying house is sound.

We see buyers who genuinely appreciate Westport’s Capes, ranches and older colonials. They may be perfectly happy renovating a kitchen, opening up a floor plan or adding a primary suite. But when they start adding up a new roof, windows, HVAC, electrical, plumbing, drainage, mold remediation and structural work, the economics can quickly change.

At some point buyers stop asking, “How can I make this house my own?” and start asking, “Does it make more sense to start over?” That’s often how a perfectly appealing older home becomes viewed primarily for its land.

Owners should think of home maintenance as an ongoing program — not something to address right before selling.

This High Gate Road home looks fresh and appealing. 

Start with the basics: Clean your gutters, keep water away from the house, address leaks immediately, service HVAC equipment, inspect the roof and chimney, maintain septic systems where applicable, watch for rot and insect damage, and periodically evaluate plumbing and electrical systems.

Keep trees and vegetation from damaging the house. Pay attention to basements and crawl spaces for moisture.

Save invoices, permits, warranties and information about major improvements. When it comes time to sell, being able to show buyers that a home has been consistently cared for creates confidence.

Fall is a good time to address maintenance issues. Focus on gutters and drainage, roof and chimney condition, heating system servicing, exterior wood and trim, tree limbs near the house, outdoor faucets and irrigation, and identifying any areas where water or ice could cause damage over the winter.

If you’re thinking about selling but have not done much maintenance, there are several steps to take. But putting money into cosmetic renovations before addressing deferred maintenance can be the wrong investment.

Don’t assume you need to renovate everything. First, look at the house the way a buyer and home inspector will. Identify significant structural, mechanical, environmental and safety issues first. Then prioritize the items most likely to frighten buyers, or make the cost of owning the house feel unpredictable.

A homeowner preparing to sell might be much better served spending money correcting water intrusion, repairing a roof, addressing electrical or plumbing concerns, servicing mechanical systems, removing mold or repairing exterior rot than installing a brand-new kitchen that the next owner may replace anyway.

Real estate agents can also help homeowners prioritize. The objective is to determine which improvements will give buyers confidence that the house is worth preserving.

(“06880” reports often on all aspects of Westport’s real estate market. If you enjoy our coverage — or anything else on our hyper-local blog — please click here, to support our work. Thank you!)

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Prices High — But Real Estate Market May Be Slowing

Posted on July 18, 2026 | Leave a comment

What’s up with the Westport real estate market?

Our friends at KMS Team at Compass report: 3.6% more homes have traded hands this year than last.

Through June 30, the median sales price ($2.31 million) and average sales price ($2,941,376) are both up — the latter by 14.4% from last year.

And buyers are paying 3.4% higher, on average, than the list price.

But these statistics are dated. Transactions can be negotiated and held under contract for months before closing.

Telling signs that things in Westport are slowing include median days on market creeping higher (26, up 12%), and the number of homes actively listed or closed that have taken price reductions.

Price sensitivity and buyer discernment are particularly evident in the upper range of the Westport market:

While the vast majority of property buyers come from within Connecticut, we still attract a significant number of New Yorkers, natives or those returning to the state after spending some years in the city.

In either case, Connecticut’s outdoors and open spaces continue to be an attractive draw.

This 8-bedroom, 8 1/2-bathroom, 12,946-square foot home, on 2.6 acres on Beachside Common, is listed for $22.825 million.

(“06880” often covers the local real estate scene. If you enjoy stories like this — and can afford a few bucks after buying a home — please click here to support our work. Thank you!)

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Westport Real Estate: Modern Farmhouse Giving Way To Earthier Vibe

Posted on May 10, 2026 | 7 comments

“Then & Now” — our “06880” series showing now-demolished homes, and their replacements — has generated plenty of interest.

Readers in Westport — and those who once lived here (some in the houses featured) — have opinions on residential architecture, “then and now.”

But tastes change. What’s new? What’s on the horizon?

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

We are seeing a return to more warmth emerging over the last 1 1/2 to 2 years.  People want peace and quality, in a place that invites them to settle in and get comfortable.

Real estate staging can often look the same over time. Something more personal or unique stands out.

Now, in a sea of sameness — at almost every price  point – more interesting interiors and exteriors have emerged. People want homes and furnishings with a story or personality.

New construction, with old-fashioned front porch and shutters. (Photo/Michael Mombello)

There is a new leaning toward collecting over time with an eye toward enduring quality, not a price tag.

People seek out homes that do not feel similar or mass marketed. They want their residences to be more curated, like their travel and vacations.

New net-zero construction on Westport Avenue. It just came on the market.

There is always a mix. If we had to summarize, it feels a bit like Modern Farmhouse is giving way to a warmer, more earthy Modern Cottage vibe.

Things are moving away from stark minimalism. More natural materials and textures are being employed: natural stone, plaster, mixed woods and linen.

Natural look, with plenty of light.

Defined rooms are coming back in favor. There is a preference for fewer, better things, collected over time. Enduring quality and design integrity stand the test of time.

Exterior

  • Shutters are back, and can offer “from the curb” distinction
  • Dormers and shed dormers add roofline interest, and provide additional light on upper floors
  • Patios and crushed stone areas are favored over decks

Patio on Katydid Lane, Weston (Photo/Estative Media)

  • Outbuildings: for both work and play, they add “compound cool” to a parcel of property
  • Porches: front, back or side, they are appreciated. Covered and open, they grant shade and protection from the sun or a summer storm.
  • Ceiling fans keep the air moving, and the bugs away
  • Raised, protected garden and vegetable beds

Raised bed and organic garden. (Photo/Borgatta Photography)

  • Flower choices and gardens that respect the natural landscape
  • Garden antiques: Well-worn pieces that appear to have been there forever give the yard a sense of history and timelessness

Interior

  • Natural materials and textures
  • Beams
  • Wooden, unpainted casement openings in walnut and oak
  • Mid-tone flooring, not too white or bleached, or too dark and lifeless
  • Butcher block-topped islands and counters
  • More color, but strategically used

Family room; darker shade on walls, planked wood ceiling. (Photo/Christian Vinan for 360 Virtual Photography)

  • Vintage, tribal type oriental carpets and rugs
  • Warm and earthy palettes, and more lived-in interiors.
  • Softer whites — restaurant tones like butter yellow or light cream
  • Small, behind-the-scenes service kitchens or butler’s pantries
  • Dining rooms
  • Antique finishes on contemporary forms, and the return of silver accents
  • Free-standing showers that feel spa-like
  • Natural wood kitchens, and wood in general

New kitchen. (Photo/Estative Media)

  • Additional tile details in kitchens, bathrooms, mudrooms and entry halls
  • Cast iron enameled sinks and tubs

One other trend to note: The first-time home-buying age has steadily increased over the last few years — dramatically. Depending upon what you read, the median age is now 40.

(“06880” covers Westport real estate — and much more. Please click here to support our work. Thank you!)

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Real Estate Report: Classic Supply & Demand

Posted on April 15, 2026 | 8 comments

The old mantra about real estate — “location, location, location” — is true.

And when that location is Westport, this is also true: All real estate news is hyper-local.

Whatever else goes on in the rest of the country matters less — real estate-wise — than what happens in our 20 square miles.

Which is why — despite rising gas prices, increasing inflation and an uncertain economy — Westport’s real estate market is great.

If you’re selling.

Demand is sky-high. Supply is super-low. The result is exactly what you’d expect: The few homes that are for sale go very quickly.

And over the asking price.

This historic 7-bedroom home on Greens Farms Road is under contract for $3.75 million.

Karen Scott — a partner with KMS Team at Compass — puts it this way: “No inventory. Pent-up demand. Crazy prices.”

The reasons stretch as far back as COVID — when many New Yorkers and others “discovered” Westport, and commuting patterns changed.

And they’re as recent as this past long winter, which kept residents indoors and away from selling mode.

Continued limited inventory means that a new cohort has joined those who looked for homes last year, could not find them, but continue to search. That larger group is “competing ferociously,” Scott says. Often, it means homes sell for more than the asking price.

As of early April, there were just 48 homes for sale. Asking prices range from $1.035 million to $22.825 million.

The median sales price of single-family homes for the year so far is $2.345 million.

That’s up astronomically from the 12 months ending March 31, 2021 — $1.399,500 — which included the initial COVID frenzy.

There have been 59 sales, up 31% from last year. But new listings are still well below the previous year. The 102 homes that have hit the market in 2026 are 20 fewer than the same time in ’25.

Median days on market — 26 for this year — is not a true indicator of supply-and-demand, Scott notes. Many of those homes are new construction, and are not yet completed.

New construction — like this home at 16 Westport Avenue, a few steps from Compo Beach — is not yet finished. But realtors are ready to market it. 

A more indicative statistic, she says, is how quickly homes go under contract. When buyers are ready (with financing in place), and eager (waiving inspections, or having them for informational purposes only), a contract can be signed within days.

What drives all this?

“Westport has always been in demand, for all the amenities and features — the schools, beaches, arts, recreation, culture,” Scott says.

“And the town is run very efficiently. Taxes are not astronomical.”

However, she says, “people are now putting higher values” on those factors. And the word is getting out.

Those who have moved here in the last few years are telling their friends — and inviting them to see for themselves.

As prospective buyers drive and walk around town, and sit at restaurants, they strike up conversations with residents. They get a very positive, community-minded vibe.

“People who are already here are the best marketers” for Westport, Scott says. “It’s organic. It’s no one thing. It’s just a vibe that people feel when they visit. They hear that people love living here. And they enjoy sharing what they love about it.”

Casual conversations at the Black Duck (above), Nômade, Dandelion, Spotted Horse — and many other restaurants in town — help sell Westport to potential homebuyers. 

Meanwhile, some traditional sellers — empty nesters looking to downsize or “right size” — are not leaving. They may spend time in second homes, but they’re keeping this one, to enjoy their friends, the Library and many other activities.

Some invite their adult children — who are having a tough time entering the market — in.

And others who do list their houses are seeking even larger ones elsewhere in Westport, for multi-generational living with their children and grandchildren.

Adding to the tight supply: They don’t sell until they know where they’re going.

Before the pandemic, Scott says, sellers who were moving elsewhere in town listed their home. They waited months for a contract, and had “several hundred” properties on the market to choose from.

Now, it’s “buy first, then sell.”

So, in addition to “location, location, location,” add this to the current Westport housing mantra: supply and demand.

“It’s Economics 101,” Scott says. “It doesn’t get much simpler than that.”

(“06880” regularly covers real estate — and every other aspect of Westport life. If you enjoy stories like this, please click here to support our work. Thank you!)

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Real Estate: A Multi-Generational Tale

Posted on March 28, 2026 | 2 comments

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.

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

Posted on March 7, 2026 | 9 comments

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!)

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

Posted on February 14, 2026 | 3 comments

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!)

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

Posted on February 1, 2026 | 2 comments

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.)

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