How To Prepare For Short-Term Renters Next Door

My neighbour Bill just told us he is going to rent out his home on a short-term-rental site. Our neighbourhood has always been quiet and peaceful and filled with year-round, full-time residents, so this is new and sort of scary to all of us. How concerned should we be?

Signed, Bill’s Neighbour (a fictitious human)

Dear Bill’s Neighbour:

It was nice of Bill to mention that he was going to be renting the house. I note, however, that you did not say he asked if you would mind, so we have to assume he doesn’t care. Is Bill a little bit of a jerk? A “shovels his driveway but not the old lady across the street” kind of a guy? It doesn’t matter because Bill is now dead to us. You and your neighbours have to worry about yourselves.

The amount of concern you should have about the new, rotating cast of renters next door ranges from “none at all” to “Why is there a car in our pool?” To assist you and your community in dealing with this uninvited incursion by unknown vacationing-type people and other itinerants into your peaceful neighbourhood, here are the various types of short-term renters, and a colour-coded threat level and action plan for each.

Renter type: Invisible

Identified by: Nothing. You literally won’t know they’re there. They are quieter than the neighbours who own the house. This type of renter most likely represents the vast majority of short-term renters; people who just want a quiet family vacation somewhere cool in a nice house. Maybe some porch beers. Wave if you see them, which you won’t.

Threat level: Cellophane. A complete absence of threat. You don’t need to do anything unless you want to, which you won’t.

Renter type: Cool New Friends

Identified by: Musical selections—be it Lizzo, Kenny Chesney or The Carpenters—that coincidentally match yours and are played at socially appropriate hours and decibel levels. They beckon you to come over for drinks when they see you because they want to learn more about your interesting home town. You dig them. You swap emails and make plans to connect when you’re in their home town.

Threat level: Pink… for—LOVE them!!

Renter type: Gang of Inconsiderate Clods

Identified by: Large groups who you can hear talking even when inside your own house because they are always talking at the top of their lungs, though standing mere feet apart. Their cars fill your neighbour’s driveway, part of the street, and will, at some point, block you from leaving your driveway. They give you stink eye when approached about moving the cars. Their music and parties are not quite loud enough and not quite late enough to force you to call the cops, but you’re always a few seconds away from dialing those three magic numbers.

Threat level: Chartreuse. Ignore them to the extent possible. They will be gone in a week.

Renter type: Only People on the Planet

Identified by: Late night parties with music that appears to be entirely bass, screaming fights on the front yard, toddlers meandering aimlessly and unchaperoned on the street, animals of all sorts running off leash, at least three appearances by the cops. Hammering on your front door at 3 a.m. by confused/lost renters demanding to be let in or else they’ll “kick in your teeth.” These renters have zero respect for, indeed seem unaware of, the fact that they are not the only people on Earth.

Threat level: Red mist. Before you wake up in the backyard of Bill’s house with a gas can and a lighter, with no idea how you got there, have a heart to heart with him. Tell him his renters are not only destroying the fabric of the community and violating the town noise ordinances, but they are trying to saw up his wooden patio furniture for the fire pit, have dumped a bunch of green Jello powder into his pool, and are turning his garage door into a mural of some sort. Don’t feel bad about lying. It’s the least of the sins currently occurring on or near your property.

Renter type: Rave Advertised on TikTok

Identified by: Thousands and thousands of people. Unconscious or tweaking partiers everywhere, including your bathtub. (Does it matter at this point how they got there?) SWAT team response with National Guard unit on standby.

Threat level: For Sale. Move out as soon as you can. Then list with a local real-estate agent who is a good liar (redundancy alert), or find out which short-term-rental site Bill is using.

Greenwich, Connecticut, is in New England (just barely), but that doesn’t mean it’s a quaint, sleepy small town with covered bridges and white churches on the green.

It’s leafy, certainly, but it’s also a luxury-minded power centre close to New York City, with many celebrity residents (director Ron Howard, singer Diana Ross, actor Meryl Streep and, at one time, Australia’s own Mel Gibson).

The main shopping street, Greenwich Avenue, is home to brand stores such as Hermès, Kate Spade, Saks Fifth Avenue, and Tiffany & Co.

And Greenwich, particularly in the “back country” north of the Merritt Parkway, is host to some of the most exclusive real estate in the world.

The average price for a single-family home in the second quarter of 2025 was USD $3.25 million (AUD $4.9 million). But that’s merely an entry point, buying a smaller home in one of the town’s less desirable neighbourhoods.

What does USD $43 million (AUD $66 million) buy in Greenwich?

Last autumn’s most expensive listing offered a 1,068-square-metre waterfront home with eight bedrooms and 11 bathrooms, plus “Gatsby-like lawns”, a gym, games room, party room, wine cellar, fruit orchard, pool and spa. The front and side porches have heated floors.

Prefer something more traditional and secluded? For USD $33 million (AUD $50 million), buyers could close on an 11,760-square-metre Georgian manor on 3.2 hectares, featuring eight fireplaces, an elevator, and a dumbwaiter.

The first floor features a three-storey cascading chandelier. For bibliophiles, there’s a two-storey mahogany library. If bocce is more your pace, a similar USD $25 million compound on 7.5 hectares, built for a liquor magnate in 2009, may appeal. Fourteen bathrooms should suffice.

The Greenwich market is strong, but not without challenges.

“The big problem is that there’s no inventory,” said Evangela Brock, an agent with Douglas Elliman. “It’s extremely low at all price points.”

In November, just 15 properties under USD $1 million (AUD $1.52 million) were listed without contracts, compared with 23 above USD $10 million (AUD $15.2 million). Of those, six had contracts pending. Greenwich has more than 17,000 single-family homes.

Kanebridge Quarterly toured two mid-priced houses in Greenwich. “You don’t lose money in Greenwich real estate,” said Beth MacGillivray, a realtor with the Higgins Group. “This is the hot spot.”

MacGillivray opened the door to a 733.9-square-metre Georgian colonial in the Sherwood Farms Association development her family built in 2005. The house was expected to sell for about USD $5 million (AUD $7,743,535).

The six-bedroom, four-level house is move-in ready, with staged furniture showing its potential and many of the amenities that buyers in this range expect.

Visitors enter through a two-storey foyer with a marble floor. A circular staircase leads to an airy living room with double-height ceilings.

There’s a main bedroom with his-and-hers bathrooms, a cherry-panelled library with cigar-smoke venting, five fireplaces, and a state-of-the-art kitchen with a breakfast nook by Greenwich-based designer Christopher Peacock.

Most rooms have huge walk-in wardrobes. Even the laundry room has granite countertops. Custom millwork, cabinetry and fixtures are evident throughout.

The drawbacks? A smaller yard and no pool. Still, refugees from the city would marvel at the abundant interior space.

Not far away, an entirely different house was on the market for USD $2.66 million.

The imposing 696.7-square-metre, nine-bedroom, seven-bath Georgian/Federal home on Shady Lane in the Glenville neighbourhood was built in 1900. Its good bones and inherent grandeur were apparent, as was a clear need for updating.

“It’s a good project for someone,” said realtor Kaori Higgins. “It needs the right buyer, someone who is looking to return it to its stately original condition.”

Given the hot market, some buyers may be tempted to tear it down and build anew.

But the house is filled with charming period details, including hand-built stone fireplaces, reading nooks, pocket doors, leaded windows and beautiful original millwork.

The second floor offers a vast veranda with views of Long Island Sound and a built-in swimming pool.

The drawbacks? Bathrooms that were awkwardly redesigned in the 1970s, unsightly flooring on the upper levels, and crumbling exterior elements.

Higgins noted that a nearby sister property, fully renovated, sold for USD $11 million (AUD $17 million). Any buyer of Shady Lane’s faded elegance would need both imagination and deep pockets.

For contrast, Kanebridge Quarterly left Greenwich for nearby Fairfield’s upscale Greenfield Hill neighbourhood to visit Lion’s Gate, a 595 square metre Tudor Revival home built as a modest dwelling in the 1920s but extensively expanded and remodelled in 2000.

With three acres of land, a guest cottage, an artist’s studio and a pool house, the asking price is USD $3.3 million (AUD $5 million). Like the Sherwood home, Lion’s Gate is flawlessly move-in ready, with designer touches throughout.

The entire second floor was added during the renovation and features parquet flooring, a massive main suite, arched doorways and 2.74-metre ceilings.

Many rooms include walk-in wardrobes, extensive carved millwork and built-ins. The wood-panelled library (on the site of the former stable) is warm and inviting.

The expansive kitchen includes a window seat with a hand-painted ceiling, a wine cooler and a butler’s pantry.

Realtor Lorelei Atwood said Fairfield faces the same inventory shortage as Greenwich.

“Demand is growing as more New York-based executives are being told they have to report to the office,” she said. “Fairfield has always been a commuter town.”

Why is this home USD $3.3 million (AUD $5 million), and the Sherwood property around USD $5 million (AUD $7,743,535)?

Location. Greenfield Hill is lovely, but Greenwich real estate occupies a rarefied class of its own.

Note: Thanks to realtor Sherri Steeneck for chaperoning.

This story appeared in the Autumn issue of Kanebridge Quarterly, which you can buy here.