By Mike Diago and Kathryn Walsh
The year 2020 will likely go down as one of the wildest rides in Hudson Valley real estate history, beginning with the late-March shutdowns — which prohibited home showings — and ending with a record-breaking year for home sales, driven largely by folks fleeing NYC in search of greener pastures.
During this ultra-tight market, with low inventory and climbing prices, the questions on buyers’ minds are not only where is the best place to live, but where are there homes to buy, and what do I need to do to get my dream home?
We asked these questions to local realtors, who told us they are encouraging buyers to: think of the type of town they want to live in more than a specific town, be willing to look at towns near their dream location, and be ready to pounce and offer above the asking price.
Here we serve you some of the most desirable villages, towns, and cities that may already be on your radar, along with some that may not be. Fortunately the types of living that the region is known for — sleepy walkable villages, small industrial river towns, and bucolic rural escapes — are plentiful.
“The beauty of living in the Hudson Valley is that you can live in one of our many small towns and be 20 minutes away or less from another lovely community,” says Linda Lindsay, of Corcoran Country Living.
Without further ado, these are some of the best places to live in the Hudson Valley:
The village of Rhinebeck has long been seducing city dwellers into abandoning busy urban lives, even if just for the weekend. It is home to the oldest Inn in America — Beekman Arms — where grand figures from George Washington to Oprah Winfrey have been lulled to sleep. Trotting along its main streets (Montgomery, Market, and Mill) past an old-fashioned-style candy shop, a 50-year-old movie theater, and some of the best restaurants in the Valley, it is easy to understand the appeal. As such, home prices have been high for a long time, and like everywhere else around here this year, they have gone up.
The median sale price for a single-family home increased 50% in the fourth quarter of 2020 compared to the same quarter in 2019, landing at $675,000. According to realtor Laurel Kerr of Corcoran Country Living, “There are almost always bidding wars. A home in Rhinebeck listed at $900,000 could sell for well over a million. To get something between $350,000 and $450,000 you have to go to surrounding towns.”
Sandi Park, a broker with Berkshire Hathaway HomeServices, reports that, “Rhinebeck is poised for saturation at the above one million mark.” She says, “I think the ‘under the radars’ are the towns surrounding or near the key villages of Rhinebeck, Millerton, and Millbrook, such as Clinton, Stanford, North East, Milan, and Red Hook.”
While Red Hook’s village has virtually no inventory, there are some homes available in the town of Red Hook for diligent buyers — median home price has risen 26% to $445,000 since fourth quarter 2019. Anywhere in the vicinity will put you within a quick drive to farms, like Greig Farm; restaurants, including the Historic Village Diner, an iconic 1920 steel bullet diner; and entertainment and culture at Bard College.
Moving east, Stanford may be the hottest little town on the list. According to Park, sales have increased 113% since 2019, the biggest jump in the Valley in 2020. It is yet another beautiful rural town — yes, we have a lot of those — with just under 4,000 residents, access to trails at Buttercup Farm Audubon Sanctuary, and Wilcox Memorial Park. The median home price is $423,000. For that you get a true piece of Americana, spending weekends outside in the fresh air or lazing the day away inside a big country home playing board games and eating popcorn with family.
Linda Lindsay of Corcoran Country Living says, “My favorite under-the-radar place is the town of Pine Plains. The village itself is reminiscent of small towns throughout America where people still sit on porches, ride bikes, and stroll.
There are wonderful outdoor activities: Twin Island Lake offers boating, swimming, and fishing, including a beach and picnic area (Stissing Lake Park also has swimming and a beach); there is the Thompson Pond Preserve and Stissing Mountain for hiking. The village provides a grocery store, a wine store, a pharmacy, a bookstore, an inn, and several lovely restaurants. The land surrounding Pine Plains is beautiful with sweeping, bucolic views and gorgeous farmland.”
While the median single-family home price in Pine Plains has shot up 64% since the fourth quarter of 2019 to $320,000, it is still a relatively modest price for a charming town in northern Dutchess County. For a lower price, one would have to go further east towards Connecticut border to towns like Millerton and Amenia where the median home prices during the same period were $272,000 and $289,000 respectively.
According to Lindsay, “Millerton is busier than Pine Plains but still has a bit of that sleepy, much-sought—after, small-town feeling. The Harlem Valley Rail Trail is wonderful for biking and hiking, running 11 miles to the Wassaic Train Station. It also has a great book store and a movie theater.”
Amenia, which is just south of Millerton, is home to Four Brothers Drive-In, which was featured on the Today show last summer; Serevan Restaurant (chef Serge Madikians was twice voted best chef by this magazine’s readers), and Troutbeck, a historic estate inn whose restaurant made Esquire’s list of Best New Restaurants in America 2020. The Appalachian Trail runs through Northwestern Dutchess and — if you’d rather not take your long trips on foot — so do the Taconic State Parkway and the Metro-North Harlem Line.
Silo Ridge Field Club, a members-only gated dreamscape situated in Amenia, among the slopes and fields of eastern Dutchess County, offers a curated lifestyle where those who can afford it can build their field of dreams. (Really: Someone built an on-site baseball field in a cornfield inspired by the movie.) Homes are available on the 850-acre parcel — surrounded by another 500 acres of land protected by the North American Land Trust — for prices starting at $2 million for a plush two-bedroom condominium to $10 million for a six-bedroom estate.
There are existing homes to choose from, or you can pick a site and build a completely custom home from scratch. Buyers can meet with an architect and visit a planning site where you can pick out your doorknobs, fixtures and other home features.
According to Dan O’Callaghan, director of sales, “In the past, many families have used their Silo Ridge residence as a second home. But with the pandemic shift toward virtual work and learning, more people are using it as a primary home.”
But you don’t just get the house, you are in a community — there are 245 single-family homes, condominiums, and townhouses on-site — of happy residents, who likely include business tycoons, entertainment personalities, and sports professionals with a taste for luxury indulgences and services.
For example, if you own a property and go on vacation, you can call on your way back and say, “Hey, I’m coming in!” and the staff will stock your fridge with your favorite liquor or cheese. If you want to go camping but don’t have time to buy a tent, they’ve got you covered.
There is an 18-hole golf course, an NHL regulation ice hockey rink, an 11,000-sq.-ft. barn with dining and projectors for watch parties, a bowling alley, a lake with a beach and a 150-foot slide, and an organic garden with a green house. There is even a resident gardener who will help you garden, and most of the seasonal produce is used in the on-site restaurant.
Rockland has the reputation of being more bohemian than nearby Westchester — especially Nyack, which has been home to writers, actors, and artists for generations (the most famous being Edward Hopper). On a given night at a village bar, you might find a magazine illustrator for Rolling Stone in conversation with a singer and the mayor.
If you want to be able to walk to that village bar, you’ll want to live in the village itself. Large condo-complexes and luxury housing developments, like Pavion, can put you steps away from dozens of nightlife options, including restaurants, Maureen’s jazz club, a wine cellar, and several bars with live rock music.
For a large Italianate home on a leafy lot along the river, look toward Upper Nyack, and for a colorful Victorian on a quiet, dead end street, you’ll want to be in South Nyack. There is some stylistic overlap.
Dale Lydecker, of Lydecker Realty, tells us, “Anywhere in Rockland County, the smallest county in the Hudson Valley, is hot. The towns are all easy to get to — 20 minutes would be the farthest drive across Rockland. The median price in 2019–2020 was $465,000. Demand is now very high and inventory very low, creating bidding wars. What used to sell for $465,000 is now $525,000 with many houses selling the first week on the market.”
In addition to Nyack, rivertowns like Palisades, Piermont, Grandview, and Upper Grandview are also in high demand as the best places to live in the region.
Georgine Addeo of Ellis Sotheby’s International Realty says, aside from the rivertowns, the town of Clarkstown, especially New City and Congers, are also hot, thanks to amenities such as town pools and camps, senior activities and senior transportation, an award-winning education system, community activities that include summer concerts, and walking and hiking paths along Rockland Lake State Park.
In the North Rockland area, with hamlets like Stony Point — where 3rd quarter sales from 2019 to 2020 experienced a rise of 13% — “the price point of homes tends to be more affordable,” says Addeo, while offering reliable transportation, recreational facilities including public golf courses, and close proximity to Bear Mountain and Harriman State Park.
“In Rockland, there can be a house in a buyer’s price range if they are willing to buy a home that needs some work, or a property that might be further [from the] location they originally wanted,” says Addeo.
“In a town with a train, like Pearl River, prices may be a little higher since they are located near NJ Transit transportation,” Addeo continues. “If a buyer is willing to go to West Nyack, the same house could be in their price range.” There, you’ll also find the Palisades Center and Rockland Center for the Arts, a true gem of the Hudson Valley, offering exhibitions, classes, events, and summer camps for kids and teens.
All of our small cities have beautiful architecture along a main corridor, but the historic row houses along Hudson’s Warren Street seem taller, older, grander, or somehow just…more. Perhaps it is because they are so beautifully preserved or because Hudson, far from Manhattan, has had to exist on its own terms. Echoes of the past — the whalers, the iron and brick workers, generations of migrants, and Hudson River School painters — mingle with the chatter of the designers, chefs, farmers, and tastemakers who drive its energy today.
Realtor James Male tells us, “It is a great transition when moving from New York City. You won’t have cultural shock because Hudson is a mini downtown Manhattan from 20 years ago. There are enough people to allow for autonomy and it’s also like a village where, if you want to get involved, you can. It is an urban paradise. If you want to feel like [you’re in] a country town, you can, but if you want to get dressed up and go to lunch, you won’t be the only one.
Warren Street is fast approaching what Bleecker Street was in Greenwich Village at one time: Small independent stores, a little grocery store, a bodega, a fashion store. It is small town America writ large, and easily one of the best places to live in the Hudson Valley. You can always find a house if you wait and look — there are just very few. An average three-bedroom house would cost more than $500,000. There may be something you could find for $400,000 but it would be further from the historic center.
Realtor Guy Barreta says, “Everybody who comes up wants to look at Hudson. But there are great towns nearby that won’t carry the same price tag. [Just across the river] Catskill has a wonderful downtown with good restaurants and an artist’s flair. The town is reinventing itself and speaking to a lot of people.”
Gary DiMauro of Gary DiMauro Real Estate agrees, and adds, “An artist class has found those places and there is a generational shift happening.”
Male says of Athens, “It has a limited housing stock and anything there gets snapped up quickly. Athens is always desirable. Previously, it was a sleepy bywater. Now it is becoming the next Sag Harbor. It has a hotel, a couple of restaurants, and a wine shop.”
Germantown sits near the border of Dutchess and Columbia counties and is also one of the best places to live in the Hudson Valley. Historically, it is a farming community founded by Palatine German immigrants. The rolling farmland and farmhouses surround a central village with an updated old grocer, Otto’s, where you can get a breakfast sandwich on site and then pick up local produce and specialty groceries like Roberta’s frozen pizzas or Black Seed bagels. Around the corner, Gaskins, the buzzing upscale tavern on a corner of the main street, makes you feel right at home. When people come to Germantown, they tend to stay, so watch closely and have your ducks in a row to snag a property there. It won’t be easy. Median home sale prices there were $340,000, though the few properties available right now are closer to $500,000.
Both Male and DiMauro think that nearby Philmont is an under-the-radar town that deserves a second look. Male says, “There are some beautiful houses there. It was built as a mill town. Most houses tend to be smaller and similar in style. There is a little bit more housing stock there. There is a lake in the middle of the village, a couple of good restaurants — Local 111 is in a converted garage with an excellent chef, Josephine Proul; the old hotel has been revived. It’s near Hawthorne Valley School, it’s near the Taconic Parkway, and it’s less than 15 minutes to Hudson where you have Amtrak.”
Despite Kingston’s well-established reputation as the cool capital of the Hudson Valley, Gary DiMauro tells us, “I still feel like Kingston is a sleeper.” We were surprised to find that in some ways he is right. For a mid-Hudson city with so much personality — the old maritime feel of the Rondout, the historic appeal and nighttime bustle of Uptown — to have a median home sale price under $300,000 is astounding.
Prices have gone up 21% since the end of 2019, but that change isn’t as dramatic as in many other parts of the Valley. Still, the market is fiercely competitive, and buyers have to be aggressive and fast to overcome competing bids. It is true that Kingston has been absorbing more than its share of the exodus of New Yorkers into the Valley, but it isn’t too late to find great properties.
Laurel Kerr of Corcoran Country Living tells us, “There are still some great, unique properties available in Kingston; one is a church renovated by a well-known artist. The Rondout area on the waterfront is an artist community; the Stockade area [Uptown] has great shops and restaurants, and there is more opening there all the time. It is really alive.” A quick search on Zillow yields a three-bedroom, three-bath, well-kept farmhouse with hardwood floors at $350,000; a four-bedroom, two-family home at $299,900; and a three-bedroom, two-bath in need of cosmetic upgrades near Kingston Point Beach for $194,500.
For more space, but close proximity to all that Kingston has to offer, one could move west toward the land of summertime swimming holes and cold mountain streams. Between the Catskill and Shawangunk Mountains, you find earthy towns like Rosendale and High Falls, where you’ll be among all manner of artisans, or the towns of Marbletown and Stone Ridge, which DiMauro describes as, “somewhat frothier.”
Best-selling author Jonathan Lee says, “Our family moved to Stone Ridge over the summer of 2020, having spent the first months of the pandemic in an apartment in Brooklyn. It didn’t take long to decide to stay permanently and build a new life here.” Among the draws is a school “where most of the learning is outdoors, and there’s a focus on art and music,” says Lee, whose family enjoys walking on the O&W rail trail, exploring Mohonk Preserve, and visiting cafes, restaurants, hardware stores, and independent bookstores in Stone Ridge, High Falls, Rosendale, Marbletown, and Kingston.
South of Kingston and directly across the Walkway Over the Hudson from Poughkeepsie, small town life skips along in the town of Lloyd, which comprises the hamlet of Highland. The saying goes, “Highland is an island” because a strong tradition of community participation within the fire department, the schools, and other institutions shows that Highland folks love their community and take care of their own. At the popular Underground Coffee and Ales, school teachers might keep tabs on former students who are now pulling the tap handle behind the bar. In a town relatively untouched by the wave of city folks, newcomers are welcome and encouraged to join in. House prices here are on the rise but current homes on the market range from a three-bedroom, one-bathroom in need of renovation for $139,999 to an updated four-bedroom, two-and-a-half bath house on a spacious lot for $495,000.
East of the Hudson, Westchester buyers are pushing their usual boundaries. “Buyers anticipate continuing the work-from-home model and have ventured further North,” said Elizabeth Nunan, president and CEO of Houlihan Lawrence, in the brokerage’s 2020 year-end report. Northern Westchester (with the likes of Bedford, Chappaqua, Katonah, North Salem, Pound Ridge, and Somers) was the biggest winner with home sales up 41% and inventory down 40%. Countywide for the year, Westchester’s inventory was down 27% while pending sales were up 46%.
Lindsay Matthews of Houlihan Lawrence has found that, even pre-pandemic, people from NYC were venturing further north than they had in the past. “It’s a whole mindset of people who really are excited about the country, and maybe down-county (think Scarsdale and Rye) is not country enough for them,” she says. The appeal grew stronger during the pandemic when more people rented in Westchester or stayed in Airbnbs and “realized that the suburbs aren’t as scary as they thought they would be,” says Matthews. “It’s not their parents’ suburbs anymore.”
The first item on Matthews’ tips to buyers is: Be ready to move fast. “If you can drop everything and come out and see [a property] in the first 24 hours, that’s a great idea. And you want to present an offer that has the least risk for the seller.” Sometimes that’s the sales price, but it could also be flexibility in moving, waiving the inspection (which Matthews thinks is risky), or waiving the appraisal contingency. “Not everyone can bid cash,” she notes. “So, you just have to get creative.” And that’s where the real estate professional comes in: “You have to make sure your agent is reaching out to the seller’s agent and knows the situation.”
When asked which Westchester towns are hottest, realtor Scott Goldman of William Raveis tells us, “without a doubt, Croton-on-Hudson,” citing the village’s schools, access to nature, sense of community, and easy commute to Grand Central. “Finding a home is very difficult as there is pent-up demand coming from the boroughs and a lack of inventory, making for a seller’s market. Homes are going into bidding wars. Median sales price is $640,000, which is a 33%, increase from 2019, and inventory is down 46%.” Goldman notes that the neighboring hamlet of Cortlandt Manor (which is in the Town of Cortlandt, along with Croton) is a good option. “For families with school-age kids, both the Croton-Harmon School District and Hendrick Hudson School District (comprising seven municipalities, including parts of Croton and Cortlandt Manor) are well-regarded and exceptional.”
Croton-on-Hudson newcomers Margaret and Zach Gorin did not get into a bidding war for their home, located near Teatown Lake Reservation, but they did act fast. “We put a bid on the house within 12 hours of it being listed,” says Margaret. “There was already another offer, but we came in significantly above ask and the other bidder did not counter, so we were automatically accepted.”
The couple — Westchester natives who moved here from Brooklyn — was looking at Westchester’s rivertowns, plus Briarcliff and Pleasantville. In their Croton home they found exactly they were looking for, including enough space for a baby, nanny, and home office; a nice property “not on top of neighbors;” a house that was architecturally interesting (nothing cookie cutter); a commute that “wouldn’t kill us if we ever go back to the office;” and “a town with highly rated schools — on the smaller side in terms of enrollment — and a liberal vibe with people from diverse backgrounds.”
For nightlife at bars like Peekskill Brewery, good eats at restaurants like Birdsall House and Whiskey River, and immediate access to Metro-North, Peekskill, a river city of 24,000, is a good bet. The train can get you to 125th street in under an hour. Median home prices are among the lowest in the Northern Westchester region at $395,000 as of the fourth quarter of 2020. Older Victorians, craftsman bungalows, and larger multi-family homes are situated along and atop the city’s steep hills; many of them have great river views. There is a strong artist community in town centered around the town’s Peekskill Arts Alliance and about a dozen galleries, venues, and Hudson Valley MOCA, a contemporary art museum.
Just north, in Putnam County, realtor William Spinelli tells us, “If money was no object I would go to Garrison or Cold Spring since it is right on the train line, but Putnam Valley is our sleeper. Closed sales in the last 12 months are up 10.4 percent. I’ve been in real estate for four years, and I’ve never seen that much growth. But when you compare it to the other towns — Southeast +39.8%, Kent +23.8%, Patterson +39.5%, and Philipstown +32% — you see why I still say it’s the sleeper.” The town is large, about 43 square miles (Manhattan is about 23 square miles for comparison), but loosely populated, with just under 12,000 residents.
Spinelli describes Putnam Valley as “a very cute little town. There are only a few stores around a post office near the Westchester County line, an IGA grocery store, and a library. You get a town with 200-year-old stone walls, mostly existing real estate and renovations, forests, lake houses around the three major lakes in town, plus Fahnestock State Park and the convenience of the Taconic State Parkway. There are 25 available homes now. The lowest is a one-bedroom, one-bath at $229,900, and the highest active listing is $1.49 million — a family compound on 67 acres with a couple of houses on it.”
According to Houlihan Lawrence’s 2020 report, the number of pending sales in Putnam (and Dutchess) increased triple digits over 2019, as many sought more open space and value. Many properties were purchased as second homes to be used as a refuge, while the number of primary home purchases rose substantially.
The biggest city in Dutchess County and the “Queen City of the Hudson” seems primed for the same arts-driven buzz that places like Hudson and Beacon have seen and that Kingston and Newburgh are now seeing. New York rocker Patti Smith’s declared 10 years ago: “New York has closed itself off to the young and the struggling. But there are other cities. Detroit…Poughkeepsie.”
Poughkeepsie, with its twin industrial engines, IBM and Global Foundries, its world class colleges and universities — Vassar College, Marist College, and the nearby Culinary Institute of America in Hyde Park — and its position at the end of the Metro-North Hudson line, is ready. Median sale price for a single-family home is still low for the region at $272,000, up only 6.7% since the same time last year.
The city of Poughkeepsie’s neighborhoods are irresistible. Little Italy, for example, is a few blocks of row houses nestled under a trestle that crosses the river, dotted with businesses, like an Italian pastry shop and Essie’s restaurant, that welcome new regulars.
Steven Kratchman, a Westchester- and NYC-based architect is one of its biggest fans. “The core of the city street layout is 18th century, mostly built out in the 19th century and early 20th. Historic single-family neighborhoods on small lots of partial acres and ornamental flourishes on live music venues provide the visual structures that give the city its character.”
And while median sale prices are low, Poughkeepsie is also experiencing fierce competition for sought-after homes, such as those “built in the early 1900s through mid-century that have solid bones and are thoughtfully priced,” says Linda Lindsay of Corcoran Country Living. “They are snapped up quick. The 1930 house I had listed in the city of Poughkeepsie was in fully executed contract within 30 days. It sold over ask for $700,000. It was the highest residential resale in the city of Poughkeepsie in nearly 15 years.” That home also had a pool, landscaped private property, and was two miles from the train station.
Poughkeepsie is one of the best places to live, work, and play for homeowners or renters. Those in the latter category, will want to check out 40 Cannon. Owner Gina Sullivan (who, along with her husband, Jim Sullivan, also owns new music and catering venue Revel 32) tells us, “[40 Cannon] was originally a hotel; we converted it into apartments in 2016. It is very urban-chic with exposed wood, brick, and ductwork. On site, we have King’s Court Brewery, the 1915 wine cellar and bar, Cafe 40, and an art gallery in the original hotel lobby.”
In the town of Poughkeepsie, Eastdale Village is a live, work, play, shop community developed by Kirchhoff Companies. When complete, it will offer more than 400 units on 60 acres, including a 25-acre park along Wappingers Creek, a pavilion with a full calendar of weeknight and weekend events and live music, an indoor theater, a large gym, and just about every type of business — from the beloved Rossi’s deli to boutique clothing stores to a State Farm insurance office — right on site.
Joseph Kirchhoff, founder of Kirchhoff Companies, tells us, “a small studio is $1,275 a month and a very large townhouse, which we call a coach home, is 2,000 square feet with 3 bedrooms and 2.5 baths for $2,950. We have 18 different floor plans.”
While the project is only about 40 percent completed, there are already 218 families living there and several businesses operating.
“I’m a Dutchess County guy,” adds Kirchhoff. “My partner, Chris Dyson, and I felt that there was a lot missing on the east side of the town of Poughkeepsie and we felt we could meet that need.”
Newburgh’s long-standing communities have made it a rich and exciting city for decades, full of community traditions and events, like the Jaripeo festivals at the Newburgh Armory that draws thousands of Mexican Americans from all over the Northeast, the annual Newburgh National Night Out that comprises dozens of family-oriented events throughout the city each summer, and countless events organized around faith communities and other groups.
Sarah Bekham Hoof, a realtor with ReAttached says, “Living in a close-knit, diverse community is one of the things that made me want to raise my own kids here in the city of Newburgh (and the stunning Hudson River views don’t hurt). Newburgh’s industrial past means it has cool warehouse buildings that are being converted left and right into creative spaces where artists do their thing. The opportunity that Newburgh has, that other towns may not, is the ability to create leverage and cash flow from one’s home.”
Elizabeth Rowley, president and CEO of the Community Foundation of Orange and Sullivan, and her husband grew up in the area and moved to Newburgh in 2014. Rowley says, “We were attracted to the passion that people had here, folks are really community-oriented and people are proud to live in the city of Newburgh. [When looking for a house] we were drawn to the river views. At first we wanted an older fixer-upper, but we decided to get a newer home on Montgomery Street toward the edge of the historic district so we still have the views and the charm of the older homes around us, and we can walk to everything that is happening downtown.”
Rowley’s advice to people interested in moving to Newburgh is, “to take walks around and talk to people, getting involved in some of the community-based organizations is a great way to get to know people.” (Rowley is involved with both Habitat for Humanity and Safe Harbors). Rowley says she can’t wait for her daughter to be part of the school district. “I hear so much about the rich programming and the different paths you can take,” she says. “We have so many friends whose kids have gone to Newburgh Free Academy and on to achieve great things. They get access to all sorts of funding and grant streams.”
Prices range widely within the city of Newburgh. Currently on the market, there is a turnkey five- or six-bedroom estate in the Heights neighborhood, situated on a bluff overlooking the Hudson River, for north of $500,000; a three-bedroom, two-bathroom row house on densely populated urban block for $300,000; and a mid-century bungalow in the more spacious west end of town for around $250,000.
For a fully suburban lifestyle that is still close to the city action look to the adjacent town of Newburgh, where more modern developments and homes with big manicured lawns and two-car garages are widely available. Balmville, part of the town of Newburgh, offers the same amount of open space but the homes are older, more stately, and, in many cases, located in dramatic settings overlooking the river.