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Chester NY Real Estate

The Orange County Town of Chester, in the black dirt region of Warwick Valley, is encircled by flourishing orchards, horse farms and wineries. In the 1970s, the village was a crafts center of dedicated artisans, now the Sugar Loaf Arts & Crafts Village, comprising everything from workshops and galleries in original 1700s structures to a world-class performing arts center, in the benevolent shadow of Sugar Loaf Mountain.

Chester is, of course, more than the village. One of the tastiest tidbits about Chester is that Philadelphia cream cheese originated here. For proof, visit the Chester Historical Society to see photos of William Lawrence’s rustic creamery and the Lawrence Neufchatel cream cheese imprint plate. In a nutshell, Kraft bought Lawrence’s plant in 1928, and to this day sells his Neufchatel as Philadelphia cream cheese, interestingly enough with the date 1872 on the label, which can only relate to Lawrence’s era. A fun fact!

The Town of Chester can boast of a heritage that goes far beyond cream cheese, and some of the surviving buildings are on the National Register of Historic Places. For one, there’s the 1915 Erie Station, Chester’s local history museum, where the Historical Society holds its monthly meetings. To get an authentic taste of the town, don’t miss their events, including the annual yard sale fundraiser, penny social and holiday special exhibitions. Being directly on the Heritage Trail, several yearly charity walks and runs avail themselves of the Museum's hospitality. We have the Historical Society to thank for a nice long list list of all kinds of cool people, places and things nearby.

 


 

Chester Properties For Sale

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$900,000 - $1,000,000 Over $1,000,000
New
7 Black Meadow Road, Chester
  • Commercial Sale
  • 0 Beds
  • 0 Baths
  • 0 SqFt

7 Black Meadow Road, Chester

$8,000,000 ↑ $1,000,000
New
1253 Kings Highway, Chester
  • Land
  • 0 Beds
  • 0 Baths
  • 0 SqFt

1253 Kings Highway, Chester

$2,000,000
New
151 Kings Highway Bypass, Chester
  • Residential
  • 4 Beds
  • 5 Baths
  • 5,539 SqFt

151 Kings Highway Bypass, Chester

$2,000,000 ↓ $195,000
New
42 Brookside Avenue, Chester
  • Commercial Sale
  • 0 Beds
  • 0 Baths
  • 0 SqFt

42 Brookside Avenue, Chester

$1,750,000
New
1 Oakland Avenue, Chester
  • Residential
  • 6 Beds
  • 4 Baths
  • 4,837 SqFt

1 Oakland Avenue, Chester

$1,600,000
New
143 Conklingtown Road, Chester
  • Residential
  • 4 Beds
  • 4 Baths
  • 2,852 SqFt

143 Conklingtown Road, Chester

$1,200,000
New
45 Rock Ridge Road, Chester
  • Residential
  • 3 Beds
  • 3 Baths
  • 3,235 SqFt

45 Rock Ridge Road, Chester

$1,195,000 ↓ $300,000
New
16 Sunset Ridge Road, Chester
  • Residential
  • 4 Beds
  • 4 Baths
  • 5,712 SqFt

16 Sunset Ridge Road, Chester

$999,999
New
158 Kings Highway Bypass, Chester
  • Residential
  • 4 Beds
  • 4 Baths
  • 3,202 SqFt

158 Kings Highway Bypass, Chester

$975,000
150 Kings Highway Bypass, Chester
  • Residential
  • 4 Beds
  • 4 Baths
  • 3,202 SqFt

150 Kings Highway Bypass, Chester

$975,000
144 Kings Highway Bypass, Chester
  • Residential
  • 4 Beds
  • 4 Baths
  • 3,202 SqFt

144 Kings Highway Bypass, Chester

$925,000
New
148 Brookside Avenue, Chester
  • Commercial Sale
  • 0 Beds
  • 0 Baths
  • 0 SqFt

148 Brookside Avenue, Chester

$799,000

 


 

 

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Things To Do In Chester, NY

LODGING

When you’ve been new-home-hunting in Chester, stay over at the Holiday Inn right in the Village of Chester! Or choose from one of the elegantly decorated rooms at the Stagecoach Inn! 

Sports & Outdoor Activities

Explore Goosepond Mountain State Park’s 1,500 acres! Put the clubs in the car & head to Bill Flynn’s course at Monroe Country Club! Shoot hoops at Chester’s Oak & Carpenter parks! 

Arts & Entertainment

Creativity is alive & well in Chester at Sugar Loaf Performing Arts Center! From cumbia to country, trip the light fantastic at Diva Dance Studio! Take in a film at Elite Cinema 6! 

Farms & Markets

Shop for all your chemical-free veggies & fruit at Bienskie Farm & Sun Sprout Farm! In the market for edible flowers? Chester Agricultural Center has them… & organic watermelons! 

FOOD

Agua Fresca & Frijoles at Sabor A Casa!  Felafel & Tzatziki at Allan’s! Tofu & Spicy Soup at Magoya! Bacon Burger at Christopher’s Bistro! Maple Latte & Croissants at Meadow Blues! 

Fitness & Lifestyle

Take up Tae Kwon Do at Northeastern Martial Arts! If you’ve ever imagined yoga in mid-air, see what they’re up to at Flexibility In Flight! Then smarten up at Chris Cuttz Barbershop! 

Shopping 

Artisans thrive at Sugar Loaf Arts & Crafts Village: Sugar Loaf Candle Shop is celebrating 40+ years! Sift through herbs, essential oils & skin care at Sugar Loaf Mountain Herbs! 

Attractions

At Castle Fun Center go from the roller skating rink to mini-golf, from the climbing wall to the arcade, from the driving range to the batting cages! There’s something for everyone! 

There's so much to do in Chester, NY - it can be hard to decide! Contact one of our Local Experts at Village Green Realty. We'd love to give you our recommendation on the best things to do in Chester.

 

 


 

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Chester NY Homes For Sale

Chester Homes For Sale

 

Another local annual community gathering is a kite festival at Knapp’s View at the foot of Sugar Loaf Mountain. The site itself is a cause for celebration, as it was rescued by the town from development and will be preserved in perpetuity as open space for “passive recreation,” including bird-watching. Apparently it’s very popular with our feathered friends!

It’s a magnificent area in general, and there are loads of things to do outdoors at the town’s parks as well as at Goosepond Mountain State Park, where you can investigate the 5,000+-year-old Greycourt Rock Shelter. The reason this area has the rich soil that’s given it the “black dirt” nickname has to do with a glacier that covered the area back in the day; there were people of a sort here quite a long time ago, and the skeletons of mastodons and their pals are well-known in the region.

Of course the area is loaded with beautiful farms; find delicious organic jams and produce at Pine Hill Farm, fruits and vegetables at Roe Orchards and organic produce at Sun Sprout Farm. And stop by the roadside shed for honey, eggs and syrup at the historic Fury Brook Farm, founded in 1731! Thirsty? Within a really small radius are four breweries: Rushing Duck, Long Lot Farm, Tin Barn and Drowned Lands Brewery.

It’s hard to express the richness of a place like Chester. It’s just like the black dirt, made up of years of hard work, history and helping hands.

 

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Chester NY Homes

Chester NY Real Estate

Exciting choices abound in Chester, like a four-bedroom, five-bath, 7,200-square-foot Aspen-style Chester estate for sale. Made for entertaining, retreats or whatever you’ve got in mind, this Chester home for sale sits on eight private acres with hiking trails, waterfalls and a luxurious backyard with outdoor kitchen, cabanas, pool, jacuzzi and a sandy beach. Cedar beams, stone details, skylights and cathedral ceilings, several dining areas and multiple living rooms, a loft area with theater, sauna/spa and helipad complete the picture of a spectacular Chester property for sale.

Another lovely, private Chester home for sale is a four-bedroom, 3.5-bath contemporary with a beautiful heated, in-ground pool out back. An open-concept dining/kitchen area and glass wall of doors overlook the pool and gardens. The custom-designed kitchen with honed marble counters, the bedroom with custom-designed bath, a large family room with fireplace and slider leading out back and a guest suite or space for extended family on the lower level add to the enjoyment. The yard has interesting rock outcroppings and a fire pit, and the detached two-car garage offers plenty of storage, all on 8.7 Chester real estate acres.

Or how about a six-bedroom, 7.5-bath, 7,000+-square-foot Chester home for sale restored from top to bottom. A private winding road leads to 10 acres of privacy for this Chester A-frame with new roof, new mechanicals, new electrical, new furnace, new luxury bathrooms, new streamlined kitchen and more. A three-story entranceway, floor-to-ceiling windows, fabulous stone fireplace and a separate apartment for extended family or guests is further enhanced by the 1,800-square-foot deck with spectacular Orange County views. Almost all furniture and fixtures included.

If you have any questions about Chester Real Estate and Chester Homes For Sale, feel free to contact Coldwell Banker Village Green Realty. We'd love to show you all that Chester NY has to offer.

 


 

Chester NY Real Estate Statistics
At Coldwell Banker Village Green Realty we love sharing our market knowledge with our clients and neighbors. Market statistics might inform whether or not you decide to sell or hold a property or they might impact which town or village you choose of the three you're considering. To the right you'll find some basic market statistics. For in-depth comparative statistical reports visit our "Market News" page.
Property Types (active listings)
Average Price: $558,287
Total Listings: 103
Avg. Days On Market: 17
Avg. Price/SQFT: $207
Highest Price: $8,000,000
Lowest Price: $950
Avg. Property Age: 54 YEARS
Basic Statistics (active listings)

 

 


 

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Hudson Gateway MLS LogoINFORMATION COPYRIGHT 2022, ONEKEY™ MLS. ALL RIGHTS RESERVED. THE SOURCE OF THE DISPLAYED DATA IS EITHER THE PROPERTY OWNER OR PUBLIC RECORD PROVIDED BY NON-GOVERNMENTAL THIRD PARTIES. IT IS BELIEVED TO BE RELIABLE BUT NOT GUARANTEED. THIS INFORMATION IS PROVIDED EXCLUSIVELY FOR CONSUMERS’ PERSONAL, NON-COMMERCIAL USE. THE DATA RELATING TO REAL ESTATE FOR SALE ON THIS WEBSITE COMES IN PART FROM THE IDX PROGRAM OF ONEKEY® MLS

Listing information last updated on September 28th, 2022 at 11:40am EDT.

Listing information last updated on September 28th, 2022 at 11:36am EDT.