Wilton, CT, Realtor &
Luxury Listing Agent
Judy Michaelis is a licensed Connecticut real estate broker specializing in Wilton luxury homes, estates, antique properties, and architecturally distinctive residences. Thirty years in Fairfield County, $600M+ in closed sales, and the pricing strategy, marketing, and negotiation expertise that made her the area’s top listing agent.
88 Drum Hill Road
$250,001 over asking, in 6 days.
The house came to market on a Thursday with professional photography shot two weeks earlier and a marketing plan already built. It was under a contingency-free contract six days later, in cash, a quarter of a million dollars above the asking price.
The highest offer was not the one that was accepted. Read the full breakdown of how the offers were evaluated and why.
Beyond The Comps
Every market has its own mechanics. In Wilton, four of them do most of the work — and all four are settled before the sign goes up.
What buyers come for
- Acreage, wooded privacy and the approach to the house
- A deep supply of antique and architecturally distinctive houses that resist formulaic comps
- Land and setting at a price point that brings buyers in from across the region
- A limited number of comparable sales each year
Hiring The Right Agent Matters
- Pricing has to be argued from the property, not averaged from the ZIP code
- Photography and staging carry more weight when the house is the differentiator
- The buyer pool reaches well beyond the town, so marketing reach matters more than local presence
- Days on market behaves differently — a slower first two weeks is not the signal it would be in a busier market
Six Neighborhoods,
Six Different Markets.
Wilton is a distinct real estate community, and Judy’s local knowledge of home sales helps sellers list their homes based on factors beyond comps and square footage.
Cannondale
Historic village character, the Metro-North stop, and some of the town's most distinctive older houses.
Silvermine
The arts-colony corner shared with Norwalk and New Canaan. Artist studios, river frontage, strong architectural pedigree.
Drum Hill
Elevated, private, generous parcels. Where 88 Drum Hill sold $250,001 over asking.
Nod Hill & Ridgefield Road
The Route 33 corridor and the Weir Farm side of town — acreage, stone walls, and considerable estate inventory.
Georgetown
The northern village, shared with Redding and Ridgefield. Mill-town history and a distinct price profile.
Sturges Ridge & Belden Hill
Established residential Wilton, close to the center, with the town's deepest pool of family buyers.
Estates & acreage
Multi-acre parcels where the land carries as much of the value as the house. Pricing these from square-foot comps leaves money on the table.
Antique & historic homes
Period houses with real provenance. The buyer pool is narrower and further away, which changes how and where the house needs to be marketed.
Architecturally distinctive
Contemporary, mid-century and architect-designed houses that have no true comparable. These sell on presentation and on finding the one right buyer.
Judy sells over asking
in days, not weeks.
Every figure below is a closed transaction, not an estimate.
Both houses came to market in 2026. Both were under contract six days later. Both closed above asking.
Thinking of selling your Wilton home?
Sell With Judy
Judy brings three decades of Fairfield County pricing, marketing and negotiation to Wilton sellers.
Thirty years in Fairfield County real estate, more than 600 homes sold and over $600 million in closed sales. A founding agent of the Coldwell Banker Westport office and a member of the International Society of Excellence. When you hire Judy, you work directly with Judy — from the pricing conversation through preparation, offers, negotiation and closing.
- Licensed Connecticut Real Estate Broker
- Coldwell Banker Global Luxury Director
- Graduate, REALTOR® Institute (GRI)
- Seniors Real Estate Specialist® (SRES®)