Real Estate

Some towns are drive throughs or fly overs. You don’t know exactly where they are, where they begin, or where they end. There’s no center, no bank, no traffic light, no school – sometimes there’s not even a post office. 

Milan, NY, is one of those in-between towns on the way to the Taconic Parkway or Millerton. It is bordered by Rhinebeck and Red Hook to the west, Pine Plains to the east, Stanford to the southeast, Clinton to the south, and Gallatin in Columbia County to the north. With a population of 2,245 it is the least populous town in Dutchess County but the fastest growing one since 1980. 

Originally the western part of the Little Nine Partners Patent of 1706, Milan was largely an area of farms and small local mills. In 1818 the New York State Legislature officially created the town, but no one knows why an area settled originally by Palatines was named Milan or why the accent falls on the “Mi” not the “lan” like the Italian city. 

The opening of the Erie Canal fostered the growth of Hudson River towns, and then the railroad cut down on the east-west road traffic crossing Milan, and the population declined after 1840. The forested terrain is not quite mountainous but undulates with rock outcroppings, and some areas have views across the Hudson Valley to the Catskills. During the Gilded Age, wealthy New Yorkers, including Frederic Wilcox, purchased struggling farms and created grand estates. 

Milan roadside attractions

Route 199 is the only major east-west thoroughfare in Milan, with three landmarks all west of the Taconic. The solitary Milan Town Hall, which has the look of a country club, is surrounded by lawns and has a view of the Catskills. Lacking a post office, it is the only spot for community gatherings. The building was donated to the town by Irene Kilmer Wilcox who also gave it the 615-acre Wilcox Park, one of Dutchess County’s largest parks, named in honor of her husband and son and located the border of Red Hook and Milan. 

People drive hours to cut their Christmas trees at Battenfelds or buy anemone bouquets from its green houses. The Mad Man of Milan, Steve Schreiber’s 31-foot-tall steel “Fork in the Road” along with other whimsical sculptures mark the borders of Rhinebeck, Red Hook, and Milan at the convergence of Route 199 and Route 308. 

Surprising sales results

Like the rest of the Hudson Valley, Milan has seen a steady increase in median price over the last ten years rising from $300,000 in December 2013 to a peak in August 2021 of $725,000 before declining to $510,000 in December 2023. Generally, Milan median prices are below Rhinebeck’s, often above those of Red Hook, and consistently above those of Pine Plains, whose December 2023 median price was $350,000. The same relative values are true in price per square foot; Milan’s $202 was well over Pine Plains’ $115, but below Rhinebeck’s $243. 

Both Pine Plains and Milan are smaller in terms of people and parcels with only 20 to 25 closed sales a year compared to the more populous river towns of Red Hook and Rhinebeck, which range from 70 per year to a peak of almost 150 in 2021. Realtors hypothesize that Milan’s strong numbers are due to its proximity to Red Hook and Rhinebeck and their superior school systems, closeness to the Taconic State Parkway, and availability of land. Most residents who live in the town seem to identify with Rhinebeck but value the privacy Milan offers.

Luxury properties in Milan

“High-end modern home builders have been attracted to Milan over the last few years for its larger land parcels, which offer both more natural beauty and very much coveted privacy,” according to Joseph Briggs, a realtor with William Pitt Sotheby’s in Chatham, NY. 

Sales statistics confirm that in the category over $1,000,000, Milan sells higher priced homes than Rhinebeck with a median sale of $1,667,500, although the number of sales is far fewer. The best example of this is Sylvan Rock, the first private residential estate designed by Aston Martin, which listed pre-construction at $8,250,000 and is now pending. It offers a sleek design, four bedrooms, and six baths on a 56-acre lot.

Milan right now

Looking online for property for sale in Milan is confusing because listings are typically coded by zip codes and post offices, so some homes that appear in Stanford, Red Hook, Rhinebeck, and Pine Plains may well be in Milan. To peruse availability, be sure to type “Milan” into your search. 

Twelve homes are actively listed in Milan in a range of prices up to $3,500,000, with small discounts taken from listing prices. In any given year, Milan averages about ten residential lots for sale, including three on Academy Hill, each for $300,000. Yearly home sales in Milan average between 20 and 25 – it’s a steady, unhurried market that’s well worth the time to explore. •

Christine Bates is a registered real-estate agent in New York and Connecticut with William Pitt Sotheby’s. She has written about real estate and business since Main Street Magazine’s first issue in 2013.