You’ve Lost the Bidding War On Your Dream Home

If you are trying to buy a house right now, you’re in the middle of a real-life Hunger Games. You finally find that perfect little house that you can’t live without, and there will be 13 other people who feel the same way.

That means you’ll be sucked into the worst possible outcome in any house-hunting scenario—a bidding war. Those other house hunters, like you, will do whatever is required and use all the weapons at their disposal to land the place. And when you lose, which you most likely will, you will watch your dreams—of backyard cookouts, of being able to get out of bed on both sides, of room to turn around in the bathroom without bumping your butt on the sink, of a kitchen in which your pots and pans don’t all have to live in the oven—evaporate. You will be gutted. You will grieve mightily, just like when [your childhood pet’s name here] got hit by a car.

The good news is that you will get over it, eventually. But first, you’ll have to go through the five stages of grief that accompany the loss of any bidding war. The stages start right after you stop swearing. Here’s what each stage looks like, plus some suggested coping mechanisms to get through them:

Stage One: Denial

You didn’t really want that stupid house. It’s a stupid house. Forget that house.

You should: Keep saying this to yourself until this stage wears off. It’s the best you’re going to feel for awhile.

Stage Two: Anger

That house wasn’t stupid! It was awesome and you lost it. Why do you keep on LOSING?? Why can’t you ever WIN anything? It’s just like the high school state basketball championship that you LOST. And all those times you lost the lottery. Oh great! Now there’s a hole in the wall above the TV from you throwing your laptop in loser rage. Loo. Zer.

You should: Stop with the throwing. You’re going to be in your house awhile. But don’t repair the hole. That’s just conceding that you are never moving out. Go buy a painting to cover it up. It will take your mind off all the losing.

Stage Three: Bargaining

You are brilliant! Why didn’t you think of this before? You tell your broker to offer 5% above the winning offer, no matter what it was. Your broker tells you it was all cash, 30% over asking, included a new Range Rover, the buyers are closing on the property in eight hours, and their moving truck is already idling outside the house. “Face it,” your broker says. “You lost.” “NO!” you think really loudly to yourself. “You lost, broker person. YOU lost.”

You should: Drink and cry. But whatever you do, don’t watch HGTV. All those clueless, insanely picky, delusional, yet somehow winning house hunters will make you throw things at the TV, which you can’t replace because you need your savings for a downpayment. Theoretically.

Stage Four: Depression

You will never find a house. Just quit looking. It’s pointless. Why even bother? You’re going to be stuck in this dumb, ugly house for the rest of your life, looking at that terrible painting you just bought to put over the hole. You hate that painting. What is that even a painting of? An angry bee stinging a… a walrus of some sort? Is it even hung the right way up? It looks like a five-year-old drew it. It’s a stupid painting.

You should: Stop drinking and go to bed. Leave the picture alone. It’s hung properly. You maybe should have paid for a nicer one, or bought some fine art photography of the Eiffel Tower or a foggy Brooklyn Bridge. Deal with that tomorrow. If you have dreams about blowing up that house that someone else won, that’s a normal part of the grieving process.

Stage Five: Acceptance

Wait. That’s not a bee and walrus. It’s a flower in a garden. Now that the morning sunlight is hitting it, it’s not that bad of a painting. The colours go with the comfy chair. Like you planned it that way. You sort of like it now. You’re gonna sit in that comfy chair and admire your new painting, have a cup of coffee and take a quick scroll through the listings sites to see if anything came on the market overnight. You’ll use your phone, since your laptop is in pieces.

You should: Love the one you’re with. Maybe go ahead and fill in that hole. Keep the faith. Your house is out there. It might take you a year to find it. You might need to look at 100 houses or more. Maybe you’ll have to wait until this insane market crush has calmed down a bit. But you’ll find it. In the meantime, remember to be thankful that you’ve got a roof over your head, be that as it may.

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.