Your #1 Wilton Realtor &
Luxury Listing Agent
Judy Michaelis is the top Westport & Wilton real estate broker specializing in Wilton luxury homes, estates, antique properties, and architecturally distinctive residences. Trusted by sellers since 1994, $600M+ in closed sales, and the pricing strategy, marketing, and negotiation expertise that makes her a top local listing agent for Wilton.
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 must 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 just as much as local presence
- Days on market behaves differently—a slower first two weeks doesn't mean it won't be in a busier market
Explore the data
Judy Knows Your Market
Recent Wilton Sales.
Every closed single-family sale in Wilton this year, plus four neighboring Fairfield County towns. Filter by neighborhood, price, beds, baths, or style to see how homes like yours are selling right now.
Recent closings
Thinking of selling your Wilton home?
Sell With JudyThe Wilton market, then and now
Prices up.
Sellers down.
Unique Properties in Wilton
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 rely on reaching the right buyer.
Judy sells over asking in days, not weeks.
Every figure below is a closed transaction, not an estimate.
Video-First Premium Listings. For Today's Buyer.
Not all video is equal. AI-stitched photos give buyers a slideshow. Real video gives them a scroll-stopping house they want to walk through. Your home’s first showing happens on a screen. Judy makes it count with professional photos and film guaranteed to attract buyers. Judy’s listings are filmed and published as video tours on her YouTube channel. Today, she has more than 400 videos and 1.28 million views to date, with a single house tour reaching 28,000 viewers recently.
- Every new listing video gets over 5,000 views in the first 30 days!
- 58% of buyers expect video as part of their home search
- Listings with aerial drone footage sell 68% faster.
Cinematic Storytelling:
We do not shoot simple phone walk-throughs. We craft immersive visual tours using dynamic camera movement, curated soundtracks, and strategic composition to evoke an immediate, powerful emotional response.
Drone Photography:
Drone work anchors the house in its setting, whether that is four acres, a shoreline, or a long approach through trees. Every Fairfield County property is different, and the aerial is where the difference shows.
Masterful Lighting:
True luxury lives in the details. Our production team understands how to harness natural light and supplement it to highlight high-end finishes, rich textures, and architectural brilliance without looking artificial.
Thinking of selling your Wilton home?
Sell With Judy
Trusted by Fairfield County sellers since 1994.
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
- Certified Public Accountant (CPA)
- Graduate, REALTOR® Institute (GRI)
- Seniors Real Estate Specialist® (SRES®)