Real Estate

Some real estate agents have remarked, “If clients can’t afford Rhinebeck, they buy in Millerton,” due to the similar character and structure of these two Dutchess County villages, the latter being smaller in scale, size, and population. Over the last ten years, all walkable villages and hamlets with an active center have become more sought after, exceeding the general increase in median home prices. Single-family residences in Rhinebeck, NY, have risen 200% in the last ten years from a median price of $288,000 in 2014 to $577,500 in June of this year compared to a 180% increase in Dutchess County overall to a median of $424,000. 

The vibrancy of villages with entertainment, restaurants, recreation, stores, and neighborhoods has attracted a new generation of both full-time and second-home buyers seeking the authenticity and community of a small town.

Rhinebeck has been a crossroads in the Hudson Valley for 300 years since the arrival of the Dutch in the 1680s. The Village of Rhinebeck was settled in 1686 and formally incorporated in 1834 as a separate municipality with its own mayor and government within the Town of Rhinebeck. Covering 1.5 square miles, Rhinebeck has an assessed tax base of $665 million, six times that of Millerton, and three times larger than the Village of Millbrook’s. This contributes to its comparatively low village property tax rate of 2.77 mils.

Rhinebeck is a destination village

The Village of Rhinebeck is proud of its past and boasts one of the largest historic districts in New York. FDR began his campaign for the presidency on the steps of the Beekman Arms, the oldest continually operating inn in America. George Washington actually did sleep here.

Community events like the Dutchess County Fair and the Sheep and Wool Festival at the Dutchess County Fairgrounds, the Sinter Klaus parade down Market Street in December, and the Sunday Farmers Market bring visitors year round to the sidewalks on bustling Montgomery, Market, and Mill Streets. 

With the exception of the CVS, which opened in the center of the village in 2001 over the objections of Citizens to Preserve Rhinebeck, there are no fast-food chains or big box stores in the village or town. This is a village of small family-owned businesses, an old-fashioned shoe store, a bookstore, a candy store, and an independent art movie theater. It’s a shady tree-lined village for strolling with crosswalks where traffic stops for pedestrians. It has a hospital and a highly rated school district that attracts young families. A village of just 2,700 residents, it has over 25 eating establishments from the casual Rhinebeck Bagels to excellent Italian, French, Irish, Japanese, Thai, and Indian dining and coffee shops. There’s no Starbucks in the Village, but there are excellent coffee and chocolates at Samuel’s Sweet Shop owned by Jeffrey Dean Morgan, Hillarie Burton, and Paul and Julie Rudd.

Rhinebeck has always had appealing homes

Rhinebeck’s village side streets, including Livingston, Parsonage, and especially Chestnut Street, are lined with federal, Greek revival, and Victorian homes and inviting gardens. The condition and quality of these homes account for the high median prices they continue to command. 

The percentage price increases of homes purchased and resold in the last ten years occurred across all price ranges, from 48 Arnett Road, which sold in 2015 for $220,000, the median price for all homes in 2015, to $463,500 in 2022, the median price in 2022. High-end residential sales included 27 Center Street, which sold in 2016 for $1,050,000 and in August of 2021 for $1,738,000. 

The most expensive village house during the last ten years is 21 Chestnut Street, which sold for $1,600,000 in 2018 and $3,000,000 in 2021. The demand for houses at the high end has accelerated since 2020, when homes selling for over a million dollars became more common and began to account for a much larger share of the market. 

Sales in 2024 overall have slowed because of limited inventory and high interest rates; however, four home sales over a million dollars have already been recorded in 2024. In early August there were eight homes for sale in the village, none under $500,000 and five over a million.

What does ChatGPT have to say about Rhinebeck?

After writing this article I wondered how artificial intelligence would summarize it and how different a summary in the style of Ernest Hemingway would be. Which do you prefer?

From AI: The Village of Rhinebeck has become a highly sought-after real estate market due to its vibrant community, historic charm, and appealing amenities. Over the past decade, home prices have surged by 200%, significantly outpacing the overall increase in Dutchess County. Rhinebeck’s rich history, dating back to its settlement in the 1680s, adds to its allure. It boasts a large historic district, unique local shops, and various cultural events, attracting both full-time residents and second-home buyers. The village’s real estate market features high demand for its beautiful historic homes, with sales exceeding a million dollars becoming more common. Despite recent slowdowns due to limited inventory and high interest rates, the market remains strong, with several million-dollar properties already sold in 2024.

Ernest Hemingway’s take on Rhinebeck (also via AI): Rhinebeck. A good place. Lots of old houses, some with history. People want them. Prices high. Real high. Used to be a quiet place. Now, not so much. Crowded. Expensive. Still, nice. Got some good shops, good food. People come up from the city. Look for a piece of the old life. Maybe find it, maybe not. Prices keep going up. Houses hard to find. Interest rates climbing. Still, people buy. Lots of money in this town. You want a piece of it? Better move fast. •

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.