Before you buy a $5 million home in Greenwich, CT, check four things: who maintains the property and what that costs, how old the major systems are (roof, boilers, generator, well and septic), what each season demands, and what the property tax will be at Greenwich's 2026–27 mill rate of 10.125. "A $5M home should feel like an upgrade to your life, not a second job," says Charles Nedder of The Charles Nedder Team in Greenwich, CT. Get those answers before you write an offer.
By Charles Nedder | November 15, 2026
Here's what I tell the buyers I work with: the listing photos show you the house on its best day. They don't show you the Tuesday in February when the boiler quits, or the August weekend you spend chasing a landscaper.
At this price point, you're not just buying square footage. You're buying a workload, and you get to decide before closing how big it is.
Here's the full checklist.
Who maintains a $5M Greenwich property today?
Every large Greenwich property runs on people: landscapers, pool techs, snow removal, HVAC service, sometimes a house manager or caretaker.
Ask the sellers for a list of who does what, what they charge, and how long they've done it. If the answer is "the owner handles most of it," that's information too. It means you'll be hiring all of it from scratch.
Questions to ask before you offer:
Who maintains the grounds, and what does that cost per month?
Who handles the pool, irrigation, and outdoor lighting?
Is there a house manager or caretaker, and would that person stay on?
What happens to the house when the owners are away for the winter?
In my experience, buyers who price out the staffing before they buy rarely get surprised after. Buyers who skip it often get a very expensive first year.
What does each season demand on a large Greenwich property?
Spring: cleanup, drainage, opening the pool, starting irrigation.
Summer: mowing, irrigation, gardens, pool service.
Fall: leaves, gutters, closing the pool, winterizing.
Winter: plowing a long driveway, ice, and protecting pipes when you travel.
None of these are deal-breakers. You just want the real number before you fall in love with the view.
Which home systems should you check, and how old are they?
This is where the quiet money goes. A home can look flawless and still be running on a 25-year-old roof or an aging boiler. Ask for the age and service history of each:
Roof: material, age, and recent repairs.
Heating and cooling: boilers, furnaces, and every HVAC zone.
Backup power: generator size and what it actually covers.
Water and waste: well or public water, septic or sewer, and drainage around the house.
Pool and outdoor equipment: pumps, heaters, covers, and lighting.
A standard inspection flags today's problems. It won't tell you what's coming in three years. That's why I ask for the service records, not just the inspection report.
Is the home on a well and septic, and why does that matter in Greenwich?
Many larger Greenwich properties use a private well and a septic system instead of town water and sewer. The Town of Greenwich Environmental Health Division oversees septic installations and reviews well drilling permits, and it will look up septic and well records for a property if you email ehealth@greenwichct.org with the address, according to the town's website.
Planning a pool? On a septic property, the town says a 100% replacement area for the septic system may need to be approved first, which can require soil testing. Find out before you assume the backyard plan works.
Test for radon. The Connecticut Department of Public Health recommends that home buyers test for radon. For a real estate deal it calls for a short-term test of at least 48 hours, and mitigation if levels are 4 pCi/L or higher.
Test the well water. Ask for recent water test results and have your own test done during the inspection period.
What will the property taxes be on a $5M home in Greenwich?
Greenwich's Board of Estimate and Taxation set the 2026–27 mill rate at 10.125, or $10.125 per $1,000 of assessed value. Connecticut towns assess property at 70% of appraised market value.
Appraised value of $5,000,000 × 70% = $3,500,000 assessed value
$3,500,000 × 10.125 ÷ 1,000 = about $35,438 a year
Your bill is based on the assessor's appraisal, not your purchase price, so look up the actual assessment for the property. The Greenwich Tax Collector bills real estate tax in two installments, due July 1 and January 1.
What does the seller have to disclose in Connecticut?
Connecticut law (C.G.S. § 20-327b) requires most sellers to give buyers a written Residential Property Condition Disclosure Report before a purchase contract is signed. If the seller doesn't provide it, the contract must give the buyer a $500 credit at closing (C.G.S. § 20-327c). Read the report side by side with your inspection, and ask about anything marked "unknown."
Is the property in a flood zone?
If you're looking near the water in Old Greenwich, Riverside, Cos Cob, or Byram, check the address on FEMA's Flood Map Service Center (msc.fema.gov), ask the seller for an elevation certificate if one exists, and get a flood insurance quote before you finalize your offer.
Do the showpiece features need constant attention?
Natural stone, mature specimen trees, a wine room, a screening room, a koi pond. These are what make a home memorable. They're also what need specialists.
Some of these features are worth every dollar of upkeep, and some will become the thing you avoid thinking about. Only you can decide which is which. What I can do is make sure you see the cost before you commit.
A simple gut check
Picture the first Saturday after you move in. Are you using the property, or managing it? If it feels like managing, price in the help, or keep looking. If you're still deciding where in town you want to be, start with our guide to Greenwich neighborhoods and lifestyle fit, or see what a real example looks like in what $4,000,000 buys at 14 Shoreham Club Road in Old Greenwich. Comparing Greenwich with Westchester? See our Rye, NY and Scarsdale, NY guides.
Who is The Charles Nedder Team?
The Charles Nedder Team, led by Charles Nedder, is a luxury real estate team with Berkshire Hathaway HomeServices New England Properties, 136 E Putnam Ave, Greenwich, CT 06830. The team serves buyers and sellers across Fairfield County, CT and Westchester County, NY, and uses AI-driven marketing and market data for its clients. Its luxury marketing credentials include Zillow Showcase, Zillow Preview, Zillow Pro, Realtor.com Real Pro Agent, and preferred partner status, and the team holds a 4.9 out of 5 rating across 195 Zillow reviews (as of November 2026).
Ready to look at $5M Greenwich homes with the full picture? Call the office at (203) 654-7533, call or text Charles directly at (203) 524-4303, or contact the team online. More answers are on our FAQ page.
Frequently asked questions
How much does it cost to maintain a $5 million home in Greenwich?
It varies widely with acreage, the pool and outdoor features, and the age of the mechanical systems. Get real numbers from the sellers and their vendors before you make an offer instead of guessing.
What are the property taxes on a $5 million home in Greenwich, CT?
At Greenwich's 2026–27 mill rate of 10.125, a home appraised at $5,000,000 (assessed at 70%, or $3,500,000) would owe about $35,438 a year. The actual bill depends on the assessor's appraisal, not the purchase price.
What should I inspect before buying a luxury home in Greenwich?
Go beyond the standard inspection: roof age, boilers and HVAC, generator, well water, septic or sewer, drainage, pool equipment, and irrigation. Connecticut's Department of Public Health also recommends radon testing for home buyers.
Does a Connecticut seller have to disclose problems with the house?
Yes. Under C.G.S. § 20-327b, most sellers must provide a Residential Property Condition Disclosure Report before the contract is signed. If they don't, the buyer gets a $500 credit at closing.
Do I need a house manager for a large Greenwich home?
Many buyers at this level hire a house manager or caretaker, especially for larger lots and second homes. Decide before closing who will handle the day-to-day work.
About Charles Nedder
Charles Nedder is a Realtor and team leader in Greenwich, CT, and the leader of The Charles Nedder Team at Berkshire Hathaway HomeServices New England Properties. He helps buyers and sellers across Fairfield County, CT and Westchester County, NY with luxury sales, relocation, and AI-driven marketing. Reach Charles at (203) 524-4303 or the office at (203) 654-7533.
