Fairfield County Real Estate News, Market Trends, & Tips
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Why the Greenwich Market Data You're Reading Probably Doesn't Apply to You
If you're reading the Greenwich market data and thinking it applies to you, the odds are you're wrong. What you see is: prices are up, inventory is tight, it's a seller's market. But that's not necessarily true.
By Charlie Vinci, Greenwich CT Realtor
It's a universal response, and you're making a seven- or eight-figure decision on it.
The truth is that the market is more nuanced than that, and you know it. You can feel it. You even see it when you find a house and ask yourself, why didn't this house conform to the market data?
To be frank, I can't answer that question for every house. But what follows will give you a clearer picture of the Greenwich market, and I promise you'll never see it the same way again.
If this is the first time we're meeting, my name is Charlie Vinci. I'm a Greenwich realtor, and I keep my own database of this market — every listing, every sale, every price cut — so I can analyze it in depth for you.
Why My Numbers Don't Match the Ones You'll See Elsewhere
It's not because their data is wrong. It's that it takes a tremendous amount of effort to fix the problem.
Greenwich runs on two different listing systems. There's the Greenwich MLS — it's local, the one Greenwich Realtors like myself have used for decades — and there's the larger statewide system that most of Connecticut uses.
It's my opinion that if you wanted to give your client the most exposure possible, you'd list on both. But that's not always what happens. Some homes are only listed on one or the other.
That creates a problem. It's incredibly difficult to deduplicate the listings because of subtle differences in the address, the start and end dates, and so on. So when you see a market stat online, you're often looking at numbers that are either double-counted, or pulled from just one system and missing half the picture.
My team and I have fixed that. We've deduplicated every listing across both MLS systems, which creates the most accurate version of the market. It's tedious, unglamorous work, and I don't know anyone else who does it.
It's the difference between a number you can bet a seven-figure decision on, and a number that just sounds about right.
There Are Four Distinct Markets in Greenwich
Looking at the data, I can see four distinct markets in Greenwich, and you have to know which one you're in. Here's a big-picture understanding of all four and how they differ.
Market One
The Condo Market
Historically, the condo market has had more supply than comparably priced single-family homes, and it's also more likely to be listed on only one of the MLS systems. The compound effect: if you were looking for a more affordable single-family home in town, you'd go in assuming the market was slower than it actually is. And if you were shopping for a condo, you'd go in thinking the market was more brisk — and that's assuming you had condo-specific data, which is rare.
Market Two
The Mainstream Single-Family Market
Prices will change over time, but currently this is single-family homes in the roughly $1.5M to $4M range. This segment is incredibly brisk, and if you're shopping in it, you feel it. The market data as a whole does not give you a clear picture of what you're in for.
To be frank, if you want a good home in Greenwich, you don't need to spend more than $4M. But if you wanted something above average in town, you'd shop in the next segment.
Market Three
The Premium Market
This market typically ranges from $5M to $10M. Notice I left out the $4M to $5M range — that's because it's a fuzzy transition, and the house and location weigh heavily on which market you'd fall into. The premium market is a strong market, but it's not as intense as the mainstream market. Demand is real — just calmer than the frenzy below it.
Market Four
The High-End Market
$10M and up. This is where the mainstream market data is completely useless. It's a different world. It's a buyer's market for now. If you find a great value, move on it — but otherwise, buyers usually have time and real negotiation leverage.
Want the Numbers for Your Specific Segment?
I know you want to know what the metrics look like for your segment, and I want to deliver on that. So here's what I'm going to do: in the first week of July, I'll have data for the first half of 2026, broken down into these four market segments, so you can see exactly what your market looks like.
Here's how to get the data early. If you sign up on my website and do a quick search of Greenwich properties, I'll give you early access by email. Otherwise, keep an eye out for it — and as always, give me a call if you want to discuss your plans.
The high-end market in Greenwich is literally being fabricated right in front of your eyes, and buyers are being duped.
If it wasn’t already obvious, the Bloomberg article last September made it clear to everyone that Greenwich’s $10MM-and-up market was on a new pace. If this had been a low-key source, it probably wouldn’t have received the attention it did. But it was Bloomberg.
Word traveled quickly, and now we have plenty of $10MM-plus inventory. So where did it all come from? And perhaps more importantly—is it real? Agents have been struggling to find new inventory, so why do we suddenly have so many options?
Well, I think the story is a little bigger than it looks at first glance.
I’m Charlie Vinci, a Greenwich Realtor. My website is full of information for relocators and sellers—take a look if that’s you.
One of the Fastest-Growing $10MM+ Markets in the World
Greenwich just became one of the fastest-growing ten-million-plus markets in the world. Not in Connecticut. Not in the Northeast. In the world. And when a market doubles, money chases it.
Seventeen sales in 2024. Thirty-eight in 2025—shattering a record that had stood since 2007. And we’re clearly on pace to beat 2025’s numbers.
Year over year, the $10MM-plus market is currently looking at an increase of 18% for units and 20% for dollar volume over 2025. And if past years are any evidence, the biggest sales and highest volume are yet to come. It’s likely we’ve only seen about a third of the $10MM-plus market for the year.
The Problem: The Fakers Have Arrived
The problem is, sellers and agents know it. Knight Frank reports that nearly every $10MM market was up worldwide last year. And to be fair—because I know the comments are coming—Greenwich’s top end did grow faster than every major luxury market Knight Frank tracks.
But that’s the problem. The fakers have arrived. Suddenly, properties that should be $7MM or $8MM are being priced up to $10MM. Same with higher-priced properties: homes that should be $15MM are now $20MM. $20MM becomes $30MM.
That boom attracted imitators. There are thirty-one homes asking ten million or more in Greenwich right now. About 20% of this market will go under contract in less than 30 days—those are the ones priced right.
Buyers are seeing a distorted view because so many people are jumping on the gravy train. You have got to know the market trend.
Connecticut's New Housing Growth Bill Is a Game-Changer for Fairfield County — Here's What Buyers and Sellers Need to Know
Governor Lamont has signed HB 8002, the Housing Growth Bill, into law following a special legislative session in November 2025 — and it represents the most significant overhaul of Connecticut's land use regulations in decades. Starting July 1, 2026, zoning regulations must permit residential buildings of two to nine units on any lot zoned for commercial or mixed-use development through a streamlined, non-discretionary review process. Municipalities can no longer require parking minimums for new residential developments of 16 or fewer units. And every Fairfield County community — including Greenwich, Stamford, Darien, Norwalk, Westport, and Fairfield — must complete Housing Growth Plans by June 2029. If you own, buy, or sell property in our area, this law deserves your full attention.
Why This Law Is Unlike Anything Connecticut Has Seen Before
This is, without exaggeration, the most consequential piece of housing legislation Connecticut has passed in a generation. The core of the law is straightforward but powerful: beginning July 1, 2026 — just a few months from now — any lot currently zoned for commercial or mixed-use development must allow residential buildings of two to nine units through a streamlined, non-discretionary approval process. What does "non-discretionary" mean in practical terms? It means that towns cannot simply deny these projects on a case-by-case basis. If a proposal meets the established zoning requirements, it moves forward. The days of local boards exercising broad discretion to block housing proposals in these zones are effectively over.
For towns like Greenwich, Darien, and New Canaan, where zoning has historically been one of the primary tools for controlling density, this is nothing short of a paradigm shift. Commercial corridors, village centers, and mixed-use zones throughout Fairfield County are now going to see housing proposals that would have been unthinkable even two years ago. On top of that, the elimination of parking minimums for projects of 16 units or fewer removes yet another barrier to development in walkable, transit-accessible areas. Developers who were previously discouraged by the cost and complexity of meeting parking requirements now have a much clearer path to building in the kinds of locations where housing demand is strongest.
What This Means for Property Values — It Depends on Where You Sit
The natural question on every homeowner's mind is: how does this affect my property value? The honest answer is that it depends on the specifics of your situation. If you own a single-family home on a quiet residential street, the immediate impact is likely minimal. The law's most direct effects target commercial and mixed-use zones, not established residential neighborhoods. Your home in a cul-de-sac with a big yard and access to top-rated schools is not suddenly going to have a multifamily building going up next door.
However, if you own property near a commercial corridor or in a town center, the character of your neighborhood could evolve meaningfully over the next several years as new multifamily projects come online. That evolution is not necessarily negative — in many cases, thoughtfully developed mixed-use and multifamily housing can enhance walkability, support local businesses, and increase the vibrancy of a neighborhood. But it is a change, and property owners in these transitional zones should be paying close attention to what gets proposed and approved in their area.
Good News for Buyers, Reassurance for Sellers
For buyers, this law is ultimately positive news. More housing supply, particularly in the rental and smaller multifamily segments, should help relieve some of the intense price pressure that has defined the Fairfield County market in recent years. The region has been severely constrained on the supply side, and any meaningful increase in available housing — especially workforce and moderate-income units — creates more options and more breathing room for people trying to get into the market. It will not happen overnight. The Housing Growth Plans are not due until June 2029, and construction timelines extend well beyond that. But the trajectory is clear: more housing is coming to Fairfield County, and over time that should make the market more accessible for a wider range of buyers.
For sellers of single-family homes in established residential neighborhoods, there is no reason to panic. Demand for detached homes with yards in top school districts remains extremely strong, and this law does not change that fundamental calculus. Families moving to the area for the schools, the commute to New York, and the quality of life are still going to compete fiercely for those homes. If anything, the gradual addition of workforce and moderate-income housing could actually benefit the broader local economy by ensuring that teachers, first responders, and service workers can afford to live closer to where they work. A community that can retain the people who keep it running is a stronger community — and that strength supports property values over the long term.
How Local Towns Will Respond — And Why You Should Be Watching
One of the most important things to understand about this law is that while the state has set the framework, the implementation will play out at the local level. Each town in Fairfield County will approach its Housing Growth Plan differently, and those local decisions will have a significant impact on what actually gets built and where.
Greenwich and Darien, for example, will likely push for carefully managed implementation — working within the new requirements while trying to preserve as much of their existing character as possible. Stamford and Norwalk, which already have more urbanized cores and established multifamily housing markets, may embrace the new flexibility more readily and move more quickly to approve projects under the new rules. The differences in approach could be substantial, and they will shape the housing landscape in each community for the next decade or more.
The takeaway for anyone who lives in, owns property in, or is considering buying in Fairfield County is simple: pay attention to your town's planning and zoning meetings over the next year. The local decisions being made right now — about where to encourage density, how to manage the transition, and what standards to apply — will determine how this law actually plays out in your neighborhood. This is not a distant, abstract policy change. It is happening now, and the window for community input is open.
The Bottom Line
Connecticut's Housing Growth Bill marks a turning point for how housing gets built in Fairfield County. The law opens the door to meaningful new development in commercial and mixed-use zones, removes longstanding barriers like parking minimums, and sets every municipality on a timeline to plan for growth. For buyers, it is a welcome signal that more supply is on the way. For sellers of single-family homes, it is a reminder that the market for well-located homes in great school districts remains as strong as ever. And for everyone in between, it is a reason to stay informed and engaged as your town shapes its response. The decisions being made in the next few years will define the housing landscape for a generation — and now is the time to be part of the conversation.
Westport’s odds of selling dropped to 58% in 2025. Meanwhile, Greenwich, Darien, and New Canaan all became hotter markets, making Westport the weakest performer among the four premium Gold Coast towns.
At first glance, that statistic can sound concerning for sellers. But there is an important detail most agents are not pointing out.
The Numbers Are Not the Same Across All Price Points
This trend is not consistent across every segment of the market.
In fact, the $2M to $4M price range in Westport is performing about 8% better than the overall odds of selling would suggest.
That means the headline number does not tell the full story. When you look more closely at the data by price range, a different picture begins to emerge.
A Pricing Strategy Shift Is Happening
There is also a noticeable shift in pricing strategy happening right now.
Some sellers are testing their pricing to make sure they are not part of the roughly 34% of homes that do not sell. The approach is changing as sellers and agents respond to current market conditions and the data behind them.
Want the Full Breakdown?
If you are thinking about selling and want to understand where your property fits into these trends, I can walk you through it.
Call me for a 15-minute market briefing tailored to your specific situation. I have built a custom analysis that shows exactly where this opportunity sits and how to capitalize on it.
Greenwich vs Darien in the $2M to $3M Price Point: A Clear Comparison Framework
Should you buy in Greenwich or Darien in the $2M to $3M price point? Most agents will tell you it comes down to commute time or property taxes. Those factors matter, but they are not always the deciding factors when the actual decision gets made.
The real differentiation almost always comes down to three things: value, meaning what you get for your money, how far you are willing to stretch from New York City, and your vibe preference.
1. Value: What You Get for Your Money
In Greenwich, you typically get more square footage.
In Darien, you are generally getting less space, but the market tends to be favorable to first-time buyers who commute.
Both towns can get you to Grand Central relatively quickly. But the difference in value is not just about size. It is about how that size aligns with your priorities.
2. Proximity and Commute Stretch
Both Greenwich and Darien offer convenient access to New York City. The question is not simply how fast the train is. It is how far you are willing to position yourself from the city in exchange for what you gain in space, pricing, or neighborhood setting.
3. Vibe Preference
What often determines the final decision is not the spreadsheet. It is the vibe.
Which town fits your lifestyle? Which one feels aligned with how you want to live day to day? That is the part many buyers overlook until after they move.
A Simple Framework Before You Decide
Before you choose, take the time to clarify your priorities. Start by listing everything you want in your next home. Then narrow that list down to your must-haves. From there, rank your top three priorities.
Once you have clarity, go visit both towns. Do a true vibe check. Walk around. Spend time there. See how it feels.
If you would like help working through that process, call me before you decide. I can walk you through a structured buyer consultation to help you identify which town actually fits your life, not just your budget.
You are likely to live there for ten years or more. Let’s make sure you choose the right one.
Typically, the next step is the inspection. There is a bit of a question mark around inspections these days, but ideally, we are still conducting one. During the inspection period, the attorneys are usually going back and forth drafting the contract.
With any luck, we complete the inspection quickly enough so the attorneys can finalize the contract without delay. In most cases, they prefer the inspection to be completed before the contract is finalized.
Once the inspection is complete and everything looks good, or if any major repairs have been identified and addressed, the contract is signed. When the contract is signed, that is what truly kicks off the mortgage process.
After the Contract Is Signed
Once the mortgage process begins, there is generally not much direct interaction between the buyer and the agent. At that stage, our role becomes more of a watchdog.
We are overseeing the process and making sure everyone is doing what they are supposed to do. That includes the attorneys, the mortgage representative, inspectors if necessary, and the sellers. We provide oversight and help ensure the transaction stays on track.
Offer Accepted vs. Contract Signed
It is important to understand that an offer being accepted and a contract being signed are two different things.
There are several ways a transaction can unfold depending on the town and, quite frankly, depending on where the listing agent is based and how their office typically handles transactions. There are a few broad variations, but in the overwhelming majority of cases, once an offer is accepted, two attorneys need to agree on the written contract. Your attorney and the seller’s attorney work together to draft and negotiate the terms.
Different attorneys may want different modifications to the contract. If the seller’s attorney proposes changes that create additional risk for you as the buyer, your attorney is there to protect you. They serve as a balance in the process. The attorneys negotiate the language until both sides agree on the final version. Only once both parties sign that finalized contract is the agreement fully secured.
Because of this back and forth process, there is typically a window of time where the offer has been accepted, but the contract has not yet been signed. During that period, you have not fully secured the property.
Is the Home Still on the Market?
When an offer has been accepted but no contract has been signed, the home is technically still on the market.
At the same time, it is somewhat secured. The answer is yes, but with nuance.
There are ways you should present your offer and ways you should conduct yourself throughout the process. A significant part of our role is coaching you on how to navigate this period strategically. The goal is to position you as a buyer the seller wants to stay with.
That is the key. If you come across as a buyer the seller feels confident in and wants to move forward with, they are far less likely to walk away if another offer comes in.
What Does $3MM to $4MM Get You in Connecticut’s Gold Coast?
As buyers move into the $3MM to $4MM range on Connecticut’s Gold Coast, expectations tend to shift. This price point opens the door to larger homes, bigger lots, and higher-end finishes, but the experience still varies meaningfully by town.
Below is a town-by-town look at what buyers can realistically expect in the $3MM to $4MM range across Greenwich, Westport, New Canaan, and Darien.
Greenwich
In Greenwich, the $3MM to $4MM range is dominated by single-family homes. The median home size in this bracket is around 4,000 square feet, and buyers will typically find homes with five bedrooms and four bathrooms.
Smaller homes in this range are often more updated, while larger homes may require renovation. In practice, the size and condition that tends to trade in this bracket is more than sufficient for most busy families.
Homes in this price range are most commonly found in Mid-Country, Cos Cob, Riverside, and Old Greenwich. It is far less common to find homes at this price point in Belle Haven, Byram, Pemberwick, or Glenville.
Larger lots are more typical in Mid-Country and Back-Country locations, while other areas offer a more tight-knit neighborhood feel. New construction is rare at this price point, but homes are generally larger and more updated than those found under the $3MM mark.
Westport
In Westport, it is highly unlikely to find a condo in the $3MM to $4MM range. Buyers should expect single-family homes, which can be located nearly anywhere in town, including Greens Farms.
Many of the homes in this bracket are found north of Route 1, where larger lots better accommodate larger-scale homes. Some properties may offer water views, but these are often marsh views or homes separated from the water by a road rather than direct waterfront.
A typical home in this range is around 5,000 square feet with five or more bedrooms and five or more bathrooms, marking a noticeable increase in bathroom count compared to homes under $3MM.
More updated homes tend to be smaller, while larger homes are more likely to need renovation. Buyers will also notice a clear increase in the quality of finishes at this price point. This is one of the brackets where new construction begins to appear in Westport.
New Canaan
In New Canaan, buyers in the $3MM to $4MM range may occasionally see a condo sale, typically representing one of the best units available and generally located in Town Center.
Single-family home sales in this bracket are scattered throughout town. The median home size is approximately 5,700 square feet. As with other towns, smaller homes are often more updated, while larger homes may require renovation.
Lot sizes vary widely at this price point. Buyers may choose between a smaller lot in a more tight-knit neighborhood or a four-plus-acre property in the northern part of town, with many options in between.
Homes in this range typically feature five bedrooms and five full bathrooms. More than half were built after 1980, and this is generally the price point where new construction begins to appear in New Canaan.
Darien
In Darien, the $3MM to $4MM range consists exclusively of single-family homes. These properties are found throughout town, though they are less common in the Noroton and Noroton Heights neighborhoods and on Long Neck Point.
New construction begins to appear more regularly in this price bracket. The median home size is around 4,500 square feet, with homes typically offering five bedrooms and four full bathrooms.
Smaller homes may be more updated, while larger homes may require renovation. Many homes in this range were built after 2000, and older homes tend to be well renovated.
Lots are generally larger than those found under the $3MM mark, and buyers begin to see some sales in the waterfront peninsula areas, with occasional water views.
Final Thoughts
While the $3MM to $4MM range opens up larger homes, more land, and higher-end finishes, the right fit still depends heavily on location, lifestyle priorities, and tolerance for renovation.
If you’d like help finding the right place for you, call me at (203) 952-7752.
Do Buyer's Pay Realtor Fees? (What changed in 2025?)
On October 31, 2023, a federal jury in Kansas City, Missouri delivered a verdict finding the National Association of Realtors and several major brokerages liable for conspiring to artificially inflate real estate commissions. The jury awarded nearly $2 billion in damages. The news spread quickly, and it left a lot of buyers and agents asking the same questions: What does this mean for me, and what actually changed?
Hi, my name is Charlie Vinci. I’m a Connecticut Gold Coast Realtor, and now that we’ve had time to see how this has played out, I want to break down what changed, what didn’t, and how it impacts buyers and sellers here in Connecticut.
The Three Rule Changes That Went Into Effect in August 2024
As a result of the settlement, new rules went into effect in August 2024. Here are the big three:
Sellers are not forced to pay the buyer’s agent commission.
Buyer agent commission offers are banned from the MLS (the Multiple Listing Service where agents upload listings).
Buyer agents must sign a written agreement with a buyer before touring or negotiating on a home.
One important note: this came down from the federal level, not the state level. That differentiation matters because real estate practice and existing requirements vary from state to state, including how buyer representation agreements are handled.
What This Means for Sellers in Connecticut
The headline many people focused on was that sellers are not required to pay a buyer’s agent commission. In practice, what I’ve seen is that sellers overwhelmingly still view buyer agent compensation as useful for attracting the largest pool of buyers.
The simple reality is this: the more buyers we can attract to a home, the more likely we are to generate stronger offers and achieve top dollar.
In my experience, I have not seen a reduction in seller willingness to pay a buyer’s agent commission. In fact, I have not shown a single home since the August 2024 rule changes went into effect that did not offer buyer agent compensation.
One reason this may feel less disruptive in Connecticut is that Connecticut did not require sellers to pay buyer agent compensation even before the court case. It was already voluntary here.
What the MLS Change Actually Changes
The second major shift is that buyer agent commission offers are now banned from the MLS. Practically, this means agents may not see commission information in the listing system the way they used to.
If a client has concerns about whether a seller is offering buyer agent compensation, the approach is straightforward: we contact the listing agent before scheduling or attending the showing to confirm.
The Buyer Agreement Requirement (And Why It’s Not New in Connecticut)
The third big change is the requirement for a written agreement between the buyer and the agent before touring or negotiating on a home. But here’s the key point for Connecticut buyers: this has already been a state requirement in Connecticut since 1997.
So while this part of the settlement created major headlines nationally, it is not a new concept for buyers in Connecticut.
If you’d like help navigating the current rules and making the right move, call me directly at (203) 952-7752.
What Does $1.5MM to $2MM Get You in Connecticut’s Gold Coast?
One of the most common questions buyers ask when relocating to Connecticut’s Gold Coast is simple: What does my budget actually get me?
At the $1.5MM to $2MM price point, options vary significantly depending on the town. Housing type, home size, lot size, age, and location all shift as you move from Greenwich to Westport, New Canaan, and Darien.
Below is a town-by-town breakdown of what buyers can realistically expect in this price range.
Greenwich
In Greenwich, the $1.5MM to $2MM range includes a mix of condos and single-family homes, with condos making up roughly 20% of available inventory.
Condos in Greenwich
Most condos in this price bracket are located in:
Pemberwick
Downtown Greenwich
Near the old Greenwich train station
Areas close to Cos Cob
Typical characteristics include:
3 bedrooms
2 to 3 full bathrooms
Approximately 2,000 to 3,000 square feet
For buyers prioritizing proximity to New York City and lower maintenance living, condos can offer strong value at this price point.
Single-Family Homes in Greenwich
Single-family homes between $1.5MM and $2MM are most commonly found in:
Cos Cob
Northern Riverside
Downtown Greenwich
Byram
Pemberwick
Glenville
Occasionally, opportunities also come up in Mid-Country or Back-Country locations.
What to expect:
Median size around 2,400 square feet
Typically 4 bedrooms and 2 full bathrooms
Homes built between 1900 and 1980
Smaller homes tend to be more updated, while larger homes often require renovations. The median single-family home size in this range is similar to many Greenwich condos at the same price point.
Westport
Westport offers more variety at this price range, particularly for buyers focused on single-family homes.
Condos in Westport
Roughly one-third of Westport condos fall between $1.5MM and $2MM.
Typical condo features:
2 bedrooms
Around 1,500 square feet
Buyers may find:
Newer units at The Mill Westport
Renovated units in older complexes such as Lansdowne or Harvest Commons
Single-Family Homes in Westport
The median single-family home in this price bracket is approximately 2,600 square feet.
What to expect:
4 or more bedrooms
Around 3 full bathrooms
Smaller homes tend to be updated
Larger homes may need work
Location considerations:
Homes can be found throughout town
Unlikely near Compo Beach or Greens Farms
Water proximity: focus on Saugatuck Shores
More land: explore north of the Merritt Parkway
New Canaan
In New Canaan, about 30% of sales between $1.5MM and $2MM are condos, all located in Town Center.
Condos in New Canaan
Typical condo characteristics:
Mostly 2 bedrooms (about one-third have more)
Median size around 1,900 square feet
Single-Family Homes in New Canaan
Single-family homes in this range are typically found:
South of Town Center
On the eastern side of town
It is sometimes possible to find 2+ acre lots, even at this price point.
Typical home characteristics:
Median size around 3,000 square feet
4 bedrooms and 3 full bathrooms
Homes built primarily before 1980
Smaller homes tend to be more updated, while larger homes may require renovation. An updated starter home is achievable if buyers remain flexible with must-have features.
Darien
In Darien, most condos sell below $1.5MM, so buyers in this range are typically looking at single-family homes.
Single-Family Homes in Darien
Homes between $1.5MM and $2MM are most often found in:
Downtown Darien
Noroton Heights
Other Noroton neighborhoods
Occasionally, opportunities appear:
In northern Tokeneke
On the western side of northern Darien
Typical characteristics:
Median size around 2,400 square feet
4 bedrooms
2 full bathrooms
Homes built between 1930 and 1975
Many homes in this range have already been updated. Smaller homes are often more turnkey, while larger homes may require work. An updated starter home is achievable with flexibility.
Final Thoughts
Before you start touring homes that won’t work, give me a call. I’ll help you narrow the towns, neighborhoods, and property types that make sense for your budget so you can focus only on the right options.
Greenwich CT Pros and Cons: What Changed Since 2021
What happened in 2021 shocked even me. Today, you'd be hard pressed to find a home under a million bucks, and home prices have shot up about 70 percent since then. Before you fall in love with Greenwich, this is what you need to know.
Hi, my name is Charlie. Over the last decade I’ve helped hundreds of families relocate here from all over the world. Let’s find out if Greenwich is a fit for you.
Since I did my last 2021 pros and cons video, a lot has changed in Greenwich. I think one of the biggest and most obvious changes are prices. Clearly they’re up significantly. Depending on the data that you look at, you're up roughly 60, 65, maybe 70 percent depending on the neighborhood.
However, if you were back in the market before the big covid shift which happened in late 2020, you would have felt a little differently about the market. And so this stronger market, all of these price increases do have a sort of a pro in that you can be more confident in the housing market and the strength of the housing market. And that certainly is keeping a lot of pressure in demand on the market.
Inventory and How You Shop for Homes
Another big shift in the market is a significant reduction in inventory. Quite frankly, you shop differently for a home today. I’m not sure if this is a pro or con, but I definitely think it’s something that everybody needs to be aware of.
Prior to covid, you would quite frankly probably come and see, call it five houses. Maybe you come on another next weekend and see another five. Today, there just isn’t that much inventory.
So you may come and see a few houses and then see one at a time as the weeks go on, again depending on the time of year and how much new inventory is coming out. Perhaps a little more, a little less, but just to give you an idea, that’s a big shift. It’s a shift in the way that you shop for a home.
I used to come out and just see a bunch of homes, pick one. Today you sort of have to wait or know what you want, be really clear about it, and be ready to pull the trigger so when the right one does come, you’re ready to get it.
Bidding Wars
So the bidding wars are probably a con for some people. I think this is manageable with the right agent, the right person guiding you. They can show you how to get through it. However, it's something to be aware of. For new listings that are well priced in good homes with attributes that most people appreciate and are looking for, you're probably unfortunately going to be in a multiple offer situation, especially as we roll into the spring of 2026, seeing the low inventory rolling into the years and some of the other things going on right now.
Traffic and Congestion
Another big shift locally is the traffic. So we pulled a few more people into the area with the housing boom and unfortunately it seems as though that’s created a little bit more congestion. You may see it on Route 1 in Greenwich. You may see it on Greenwich Avenue.
I think where you're going to see it most is probably on I 95, likely the stretch even after Greenwich into Stamford is one of the problem spots. But since it backs up in Stamford, sometimes that causes some issues in Greenwich as well. But the traffic congestion is a little worse than it was 4 or 5 years ago.
The Commute
The nice thing is that if you're not traveling to work by car, which quite frankly most people going to New York City don’t do, they're going to take the train. The train has remained incredibly consistent. Times are pretty much the same now as they were pre covid and you can still get into Grand Central in about 45 minutes.
The train is consistent compared to a more stressful commute where the traffic’s up and down and you sort of don’t know exactly how much time it's going to take.
Remote Work and Internet Speed
You know another great thing about Greenwich, we’ve got a lot of people that talk to me about remote work and quite frankly, the questions around internet are quite common. Is it good enough for that type of living? Definitely. Quite frankly, not only in Greenwich but in all the surrounding towns, your internet speed is excellent. So working from home and making calls over Wi-Fi no matter where you are is just not a problem here.
Healthcare Access
Another real pro and a question I commonly get is around healthcare. What's the quality of healthcare in the area? If you need something, where do you go?
If you live in the city, you probably already know there’s a lot of great doctors in the city. When we're out here, we all have the city for doctor access, but we also have Yale New Haven sort of in the middle of the two. To be completely frank with you, between those two and many of the other hospitals that are in the area that have specialists and specialties, you really aren’t at any shortage for doctors in this particular location.
Low Taxes, Strong Schools, Strong Safety Ratings
Okay, so let’s talk about some of the things that haven’t changed but are still really good attributes for Greenwich. One is the relatively low taxes. Low compared to Westchester and low also compared to Connecticut, which is much lower typically than New York State. That persists.
You want to check into the school ratings, but many people are happy with what they see there. And that’s a really important attribute for people who are buying in this town because that’s a big reason why the prices have stayed so high over the years.
I think if you look into the crime ratings, you’ll see that they’re relatively low compared to the nation as a whole and even compared to the rest of the state. That’s another attribute keeping prices strong.
The “Snooty Resident” Myth
Alright, let me address another one that I see a lot more online. I’ll be frank. I don't think anyone has ever called me and asked this question, maybe not directly, but the quote unquote snooty nature of a Greenwich resident.
Here’s what I think people misunderstand. Greenwich is part of the New York City metro. We are New York City. When you are in New York, you tend to put a shell on you, protect yourself. There’s people coming up to you asking you, trying to sell you stuff, right?
So I think naturally that transcends into our personality. And what you're seeing is a person who has a little bit of a shell, who is protecting themselves. They don’t know what you're coming up to them for.
I think what you find is once you get past that shell and past that point, you're going to find that people here are just as friendly as everywhere else. It’s just that outer shell that's throwing some people off who aren't used to it.
Beaches
And if you're a beach person, there are a lot of really great beaches in the Gold Coast. However, Greenwich Point has got to be number one in my opinion. It is 143 acres with a beach with walking trails. I’ve never taken anyone there and not have them just totally wowed.
If you live in Greenwich or are a Greenwich resident you get access. There is a pass available for non residents. It's a little tricky to get. You go to the town website, find out more about that if you'd like. But the park itself is absolutely stunning and amazing.
Diversity Concerns
Okay, let me talk about a sensitive subject. Please don’t kill the messenger. This is a really common thing that I get a call about quite often. People talk to me about diversity. Diversity in Greenwich is relatively low if you compare it to a neighboring town like Stamford. And you look at the demographics of the two, it's obvious.
What I will say is I have not experienced anything that looks like racism or sounds like somebody’s being racist. That could just be maybe my position, the people I associate with, I'm not really sure.
But what I would recommend you do is come here, explore the area, live a day here like you normally would. Come here and do some shopping on Greenwich Avenue, have a really great lunch over at Little Pub, go to Bruce Park and bring the kids to the playground.
My point to you is spend a day here like you normally would and just see if you feel like you don’t fit in. And if you feel that, you have your answer.
Walkability
Another thing that people often ask me about is walkability. Some parts of Greenwich are highly walkable. Old Greenwich in particular, downtown, even parts of Cos Cob. Highly, highly walkable.
Now, there are always places to go for a casual walk with a stroller, for a run, for a bike ride. You’ll see people doing this all over Greenwich. But when people talk about walkability, generally they’re looking for more of an urban type environment. And you’ll find that throughout different areas in Greenwich are definitely a lot of great opportunities.
Real Estate Variety
Another pro that a lot of people miss about Greenwich is the diversity of real estate. It is a very large town. That means that you can be near the coast with more of a beach lifestyle, perhaps closer knit homes closer together. And as you move north in town, the homes start to spread apart. It gets a bit more peaceful.
And so there’s an array of different types of living and you can figure out which one is the best for you.
Contractor Pricing
Another con that people often bring up to me are the high prices for home repairs and contractors. If you're not aware, in my past life before I was a realtor, I owned a construction business. We covered Greenwich and other areas across the Gold Coast.
Let me shed a little bit of light on this. There is some reality to the fact that some contractors will come to town and will price the job based on the fact that it's in Greenwich with the assumption that you could afford it more than, say, the guy in the next town.
However, what is also true is that you most likely have a higher standard than someone else, let's say, in a different town with a more modest home. That means that we need to bring better contractors. That means that contractor needs to bring his best guys. He probably needs to allow a little more time for the higher quality of job.
So it's not that you're not getting anything for the extra money. You are getting higher caliber of work. Assuming that you're doing your research to find a great contractor. And so it’s not all that money going to waste. Quite frankly, you're getting a nicer home.
Next Steps
So what's your next step beyond looking for properties? Get out and explore Greenwich and see if it’s a fit for you.
But first, give me a call, get all your questions answered, and let me know if you're planning a visit so I can show you where you’ll most likely find what you’re looking for. That way you won’t waste any time or miss anything important.
And finally, bookmark my buyers guide for the towns you’re interested in. It’s where I keep all of my maps, videos, and organized town info. It’ll give you the tools to make a great choice.
