Chester, NY Homes for Sale

• 

  

  

  /31

  $1,199,900

  • 4 Beds
  • 5 Baths
  • 4,624 Sq Ft

  16 Lori Ln, Chester, NY 10918

  Indulge in luxury living at this resort-style residence in Chester, NY, within the prestigious Monroe Woodbury School District. Set on a tranquil cul-de-sac, this home graces one of MW Schools' most beautiful streets. Crafted with precision by Paul Janus Building Arts, custom millwork, arched windows, and detailed moldings evoke the charm of Westchester and Bergen County homes. From the

  

  Randolph Rogers

  eXp Realty

  (845) 681-2264

  16 Lori Ln, Chester, NY 10918
• 

  Explore Chester

• 

  

  

  /29

  $564,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  391 Bull Mill Rd, Chester, NY 10918

  Welcome home to this storybook setting, where a majestic weeping cherry blossom greets you with it's graceful cascade of blossoms each spring. This beautifully preserved historical farmhouse set on 1.7 acres along a scenic country road just down the lane from a local farm where the soft "mooing" adds to the peaceful rural charm. Sitting pretty on a corner lot with a circular driveway, this home

  

  Alexandra Zinko

  Century 21 Realty Center

  (845) 412-9860

  391 Bull Mill Rd, Chester, NY 10918
• 

  

  

  /13

  $711,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 3,092 Sq Ft

  2 Dawn Ct, Chester, NY 10918

  Spectacular 4 bedrooms, 2.5 bathrooms colonial in the very desirable Sugarloaf Heights. This magnificent home offers heavenly views right from your rear deck. You never have to leave home when you can step outside and enjoy your own personal refuge with a fully fenced-in yard that brings privacy to your in-ground pool and hot tub. Home offers many recent upgrades which include updated kitchen,

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 203-6068

  2 Dawn Ct, Chester, NY 10918
• 

  

  /2

  $369,000 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft

  4703 Whispering Hills Unit 320, Chester, NY 10918

  Rare end unit in Whispering Hills. 3 bedrooms, 2 1/2 bathroom in spectacular location in the highly sought after Chester School district. Coming soon. Stay tuned....

  

  Erin Connolly

  Artisan Realty

  (845) 328-6250

  4703 Whispering Hills Unit 320, Chester, NY 10918
• 

  

  

  /42

  $575,000

  • 4 Beds
  • 3 Baths
  • 2,288 Sq Ft

  12 Juniper Ln, Monroe, NY 10950

  Welcome to this 4-bedroom, 3 full bath raised ranch offering a flexible and spacious layout designed for comfortable everyday living. Hardwood floors run throughout the main level, adding warmth and character to the home's living spaces. The primary bedroom features a private en-suite bath, creating a quiet and comfortable retreat. Three additional bedrooms provide plenty of room for family,

  

  Shaylene Neumann

  Houlihan Lawrence Inc.

  (329) 208-1641

  12 Juniper Ln, Monroe, NY 10950
• 

  

  /50

  $979,000

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft

  893 Laroe Rd, Monroe, NY 10950

  When you walk in the front door, the artful design and carefully curated surroundings immediately banish the outside world. The open floor plan and copious windows bring in the sunshine and natural light. Begin in the spacious living room with woodburning fireplace that opens into the family room. The living room flows naturally to the family room with its own fireplace, and it is surrounded by

  Lisa Fountain Corcoran Country Living

  893 Laroe Rd, Monroe, NY 10950
• 

  

  /22

  $345,000

  • 3 Beds
  • 2.5 Baths
  • 1,392 Sq Ft

  65 Darin Rd, Warwick, NY 10990

  Charming and move-in ready townhouse in desirable Kings Estates of Warwick, NY, located in the Warwick Valley Central School District with no HoA fees and 60 mins to/from NYC. This cozy 3-bedroom, 2.5-bath home offers an open-concept living and dining area filled with natural light. The updated kitchen boats stainless steel appliances, offering a modern touch to this warm and inviting home. A

  Sandra Laramore Redfin Real Estate

  65 Darin Rd, Warwick, NY 10990
• 

  

  /35

  $690,000

  • 3 Beds
  • 3 Baths
  • 3,200 Sq Ft

  23 Renies Rd, Chester, NY 10918

  Escape to your own sanctuary in this stunning 3 bedroom 3 full bath contemporary cedar home, perfectly blending modern comfort with natural charm. Inside you'll find an open-concept layout with soaring ceilings, large windows, and natural wood finishes that create a warm, modern vibe. The spacious kitchen features stainless appliances, hickory cabinets and an island ideal for entertaining. Two

  Kristie Jacques Century 21 Full Service Realty

  23 Renies Rd, Chester, NY 10918
• 

  

  /43

  $699,000

  • 4 Beds
  • 2.5 Baths
  • 2,548 Sq Ft

  165 Creamery Pond Rd, Chester, NY 10918

  The timeless, elegant Colonial in the Warwick School District is ready for a new hallmark. Situated just behind the Sugarloaf Arts Village—home to over 50 vibrant small shops, restaurants, and unique places to explore—this residence offers both charm and convenience. Spacious and filled with natural light, it’s perfect for peaceful enjoyment with your loved ones. A gas fireplace adds warmth and

  Kichka Pascaru Christie's Int. Real Estate

  165 Creamery Pond Rd, Chester, NY 10918
• 

  

  /8

  $899,900

  • 4 Beds
  • 2.5 Baths
  • 2,603 Sq Ft

  32 Mountainside Dr, Chester, NY 10918

  A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living

  Karen Gauvin Our House Real Estate Group

  32 Mountainside Dr, Chester, NY 10918
• 

  

  /50

  $879,000

  • 4 Beds
  • 4 Baths
  • 4,489 Sq Ft

  11 Saddle Hill Rd, Chester, NY 10918

  **Welcome to 11 Saddle Hill Road – A Perfect Blend of Luxury, Space & Location**This stunning brick Colonial offers the perfect balance of private luxury and everyday convenience. With over **5,000 square feet** of impeccably finished living space, this home provides ample room for everyone to **live, work, and relax in comfort**.Step into the **grand two-story foyer**, flooded with

  Alissa Taylor-Vetell Keller Williams Realty

  11 Saddle Hill Rd, Chester, NY 10918
• 

  

  /45

  $700,000

  • 5 Beds
  • 2.5 Baths
  • 3,115 Sq Ft

  507 Bull Mill Rd, Chester, NY 10918

  Welcome to this beautifully maintained colonial with a charming wrap-around front porch, set on 1.5 private acres within the sought-after Monroe-Woodbury School District. Offering over 3,100 square feet of living space, this 5-bedroom, 2.5-bath home blends timeless style with thoughtful design.Step inside the two-story foyer and you’ll find a bright, flowing layout designed for both

  Alison Orlando Keller Williams Hudson Valley

  507 Bull Mill Rd, Chester, NY 10918
• 

  

  /8

  $799,999

  • 4 Beds
  • 3 Baths
  • 1,867 Sq Ft

  34 Mountainside Dr, Chester, NY 10918

  ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.).

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918
• 

  

  /48

  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 4,467 Sq Ft

  53 Odyssey Dr, Chester, NY 10918

  Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a

  Hilary Ryan Goldman Howard Hanna Rand Realty

  53 Odyssey Dr, Chester, NY 10918
• 

  

  /50

  $975,000

  • 4 Beds
  • 3 Baths
  • 2,370 Sq Ft

  2 Primrose Ln, Chester, NY 10918

  Introducing an exceptional opportunity to own your dream property with over 18 acres wooded land! This stunning colonial is a perfect blend of luxury and functionality. Spanning 2370 square footage plus finished basement with 4 spacious bedrooms and 3 elegantly designed bathrooms, this home boasts an inviting atmosphere that caters to both relaxation and entertaining.As you step inside,

  Joel Friedman MS Realty Group USA, Inc

  2 Primrose Ln, Chester, NY 10918
• 

  

  /37

  $724,000

  • 4 Beds
  • 2.5 Baths
  • 3,977 Sq Ft

  278 Gibson Hill Rd, Chester, NY 10918

  AMAZING PROPERTY -- offers something for everyone! Gorgeously restored 3,977 square foot colonial farmhouse on 5.1 private acres, and with a pool, 5 bay carport, a 38x40 garage (with it's own entrance from road -- can rent out for income), and so much more! . . . Located in the Warwick Valley School District (and just a half mile to the Warwick town line). Just minutes to all downtown Warwick has

  Dean Diltz Keller Williams Realty

  278 Gibson Hill Rd, Chester, NY 10918
• 

  /2

  $769,000

  • 4 Beds
  • 2.5 Baths
  • 3,063 Sq Ft

  48 Brennan Ct, Chester, NY 10918

  Welcome to this stunning home nestled on 5 acres near the heart of Chester, NY. Tucked away for ultimate privacy, yet just minutes from shopping, dining, and major highways-it's the perfect blend of seclusion and convenience. Step inside this spacious 4-bedroom 3-bathroom retreat, designed for comfort and style. This open layout flows seamlessly with plenty of natural light pouring in through

  Claude Brischoux Keller Williams Realty

  48 Brennan Ct, Chester, NY 10918
• 

  

  /44

  $674,999

  • 5 Beds
  • 3 Baths
  • 2,983 Sq Ft

  9 Mount Ridge Ct, Monroe, NY 10950

  Tucked away on a quiet cul-de-sac, 9 Mount Ridge Court offers a rare opportunity to own a lovingly maintained 5-bedroom, 3-bath home with 3,000 square feet of light-filled living space. Owned and cared for by the original homeowner since day one, this residence combines warmth, comfort, and flexibility—ready for its next chapter.Step inside to find spacious, sun-filled rooms with an easy

  James Feldhaus eXp Realty

  9 Mount Ridge Ct, Monroe, NY 10950
• 

  

  /34

  $359,000

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft

  2409 Whispering Hills, Chester, NY 10918

  Just Move in and Enjoy! Beautifully maintained, sun filled and open 3 BR, 2 1/2 bath end unit in Whispering Hills! Lovely wood floors on 1 st floor! LR with fireplace opens to Dining area. Updated Kitchen with stainless steel appliances has sliders to private patio! Updated baths! New garage door and opener! A/C replaced about 5 years ago. Water heater replaced about 2 years ago.

  Linda Clark Hudson Valley Griffith

  2409 Whispering Hills, Chester, NY 10918
• 

  

  /45

  $549,000

  • 4 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  11 Lakeview Dr, Chester, NY 10918

  Split-level spacious home in desirable Chester neighborhood within Warwick Valley School District! This home features newer vinyl siding, a custom front entry door, hardwood floors, ceiling fans, and radiant electric ceiling heat. The 2-car garage includes windows and an automatic opener. Enjoy the fully fenced-in yard with an in-ground pool, deck with gazebo, shed, and play set—all included.

  Nicole Renda IBNA Real Estate Group

  11 Lakeview Dr, Chester, NY 10918
• 

  

  /3

  $199,000

  • Land
  • 1.85 Acres
  • $107,568 per Acre

  0 Renies Rd, Chester, NY 10918

  Seize the opportunity to own this serene, buildable lot nestled in a quiet, desirable location. Perfect for your dream home. This parcel offers privacy, natural beauty, and close to everything! Convenient access yet tucked away for peace and quiet. Don’t miss out—schedule your visit today!

  Kristie Jacques Century 21 Full Service Realty

  0 Renies Rd, Chester, NY 10918
• 

  

  /13

  $620,800

  • Land
  • 194 Acres
  • $3,200 per Acre

  68 Walter Foote Rd, Chester, NY 12853

  194 Acres in the Adirondack Park - Endless Possibilities. Two contiguous lots 32.-1-24 and 32.-1-23 located on the side of a mountain, minutes to Gore Mountain skiing, whitewater rafting & hiking trails. It offers privacy & seclusion with close proximity to amenities in North Creek. There are existing logging roads for access. Features include: a brook, pond, small wetland area, tool shed, old

  Cindy Brower Coldwell Banker Prime Properties

  68 Walter Foote Rd, Chester, NY 12853
• 

  

  /48

  $499,000

  • 5 Beds
  • 2.5 Baths
  • 3,120 Sq Ft

  358 Bull Mill Rd, Chester, NY 10918

  CHARM, SPACE and OPPORTUNITY in the highly rated Monroe-Woodbury School District! Classic vintage 5 bedroom colonial on 3.10 level acres offering the perfect blend of character and potential - all just 50 miles from NYC yet a world away from the hustle and bustle of city life. Located on a winding country road, the home sits on a large, level lot with mature trees and an in ground pool (condition

  Amy Wilhelm Corcoran Baer & McIntosh

  358 Bull Mill Rd, Chester, NY 10918
• 

  

  /41

  $449,000

  • 4 Beds
  • 1.5 Baths
  • 1,386 Sq Ft

  47 Greycourt Ave, Chester, NY 10918

  Classic farmhouse feel with contemporary updates on a generous 1.3-acre lot, with this home you get it all! This 3/4bedroom, 1.5-bath home combines classic warmth with modern comforts, including a kitchen featuring granite countertops, hardwood flooring and a spacious island perfect for prep and entertaining. along with a huge sunken living room with recessed lighting and a pellet stove to save

  Pedro Garcia Curasi Realty, Inc.

  47 Greycourt Ave, Chester, NY 10918
• 

  

  /34

  $299,999

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft

  2317 Whispering Hills, Chester, NY 10918

  Welcome to your new home at 2317 Whispering Hills, Chester, NY 10918, where resort-style living meets suburban charm! This meticulously updated property offers an incredible opportunity to enjoy a life of comfort and convenience.This delightful 2-bedroom, 1.5-bathroom home has been thoughtfully renovated from top to bottom. The kitchen is a chef's dream with brand-new stainless steel

  Jeffrey Morrissey HomeSmart Homes & Estates

  2317 Whispering Hills, Chester, NY 10918
• 

  

  /10

  $369,900

  • 3 Beds
  • 1.5 Baths
  • 1,376 Sq Ft

  264 Heritage Ln, Monroe, NY 10950

  Move-In Ready 3-Bedroom Condo in the Monroe-Woodbury School District. Discover comfort, convenience, and community in this 3-bedroom, 1.5-bath condo located in one of the most desirable areas of the Hudson Valley. The open-concept main level features a bright and spacious living room, a dining area, and a well-appointed kitchen—perfect for everyday living and entertaining. Upstairs, you’ll find

  Frank Golio Howard Hanna Rand Realty

  264 Heritage Ln, Monroe, NY 10950
• 

  

  /22

  $295,000

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft

  3708 Whispering Hills, Chester, NY 10918

  Welcome to this fantastic 2-bedroom, 1.5-bathroom condo, perfectly situated in the desirable Whispering Hills community. This unit offers a perfect blend of comfort and convenience, with an array of amenities that make everyday living a breeze. Step inside and discover a spacious, bright living area that flows seamlessly into the dining space. The updated kitchen is a true highlight, featuring

  Nikki Grzegorzewski Keller Williams Realty

  3708 Whispering Hills, Chester, NY 10918
• 

  

  /26

  $357,000

  • 3 Beds
  • 2.5 Baths
  • 1,316 Sq Ft

  2503 Whispering Hills, Chester, NY 10918

  PRICE REDUCED NEED TO SELL!!! Motivated Seller -- Discover this beautiful 3-bedroom, 2.5-bath duplex offering 1,316 sq ft of comfortable living in the highly desirable Whispering Hills condo community in Chester, NY. Enjoy great outdoor space, perfect for relaxing or entertaining. Ideal for commuters with easy access to major highways, and located within the sought-after Chester School District.

  Sonia Gonzalez Keller Williams Hudson Valley

  2503 Whispering Hills, Chester, NY 10918
• 

  

  /39

  $525,000 Open Sat 2:30PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 2,898 Sq Ft

  25 High St, Chester, NY 10918

  25 High St in Chester, NY, is a Victorian gem rich with character and ready for your personal touch. Step inside to discover original wide-plank wood floors throughout and preserved under carpeting, offering timeless warmth and authenticity. The bright modern kitchen is ready for gatherings, while the spacious formal dining room sets the stage for memorable meals. Two large living rooms provide

  Alicia Goldman Christie's Int. Real Estate

  25 High St, Chester, NY 10918
• 

  

  /13

  $89,900

  • Land
  • 15 Acres
  • $6,116 per Acre

  L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817

  Beautiful 14.7 acres located in Adirondack Heights! Private & secluded. Some clearing has been done- roughed in driveway. Site plan available- approved building lot. 20 minutes to Gore Mountain. Close to all the local lakes, restaurants, & shopping. Your Adirondack adventure awaits!

  Julia Pucciarelli Gallo Realty ADK Inc

  L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817
• 

  /2

  $139,900

  • Land
  • 46 Acres
  • $3,053 per Acre

  0 William Hill Rd, Chester, NY 12817

  Lovely large lot on William Hill Road, more pics to come.AO 6/28

  Jason Minch William Raveis-New York LLC

  0 William Hill Rd, Chester, NY 12817
• 

  

  /13

  $86,500

  • Land
  • 2.84 Acres
  • $30,458 per Acre

  38 Granite Ridge Rd, Chester, NY 12817

  Great opportunity to build your own Adirondack dream home not far from Lake George. Seller financing available . Includes 2.84 acres of gently rolling property cleared for a potential house or a cabin. All stumps and undergrowth have been removed. 200 amp underground electrical service with 30 amp and 50 amp receptacles for camper hook up. Extra sleeve for future broadband or satellite. Winding

  Walter Swartz Gallo Realty ADK Inc

  38 Granite Ridge Rd, Chester, NY 12817
• 

  

  /45

  $650,000

  • 5 Beds
  • 3.5 Baths
  • 3,617 Sq Ft

  65 Oxford Springs Rd, Chester, NY 10918

  Welcome to 65 Oxford Springs Road, Chester, NY — a custom-built Country Contemporary set on a private 2.3-acre hilltop. This one-of-a-kind property offers the perfect balance of privacy, space, and convenience, just minutes from the NYS Thruway, state parks, and only 45 minutes to NYC.Inside, the bright open floor plan is filled with natural light, featuring rich hardwood floors, custom

  Ammar Iqbal eXp Realty

  65 Oxford Springs Rd, Chester, NY 10918
• 

  

  /50

  $1,775,000

  • 4 Beds
  • 2.5 Baths
  • 3,348 Sq Ft

  20 Goshen Rd, Chester, NY 10918

  Discover a rare opportunity to own a one-of-a-kind estate set on 53 sprawling acres in the heart of Chester, NY—perfectly suited for luxury living, farming, or future development with subdivision potential. This impressive property features a 3-car garage with 10-foot doors, outdoor wood-burning furnace, and two 250-gallon oil tanks for efficient heating.Nature lovers and hobby farmers will

  Ramanjit Dhanoa eXp Realty

  20 Goshen Rd, Chester, NY 10918
• 

  

  /37

  $575,000

  • 4 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  78 Pickerel Rd, Monroe, NY 10950

  Welcome to this charming Colonial set in the desirable Trout Brook ll subdivision of Monroe. This lovely home offers the perfect balance of privacy and convenience—just minutes to local shops and the village, and a short 10–15 minute drive to all major highways. Plus, you're only an hour from NYC, making it ideal for commuters or weekend getaways. Outdoor enthusiasts will love the close proximity

  Dylan Piazza Howard Hanna Rand Realty

  78 Pickerel Rd, Monroe, NY 10950
• 

  

  /48

  $1,099,000

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  5 Gabriels Dr, Chester, NY 10918

  Exquisite Colonial Estate: Timeless Grandeur Meets Modern LuxuryNestled gracefully on a private cul-de-sac amidst meticulously manicured grounds, this sprawling Colonial estate offers an unparalleled blend of classic elegance and contemporary comfort. From the moment you approach the stately wrought-iron fenced property and enter through the grand foyer, you are greeted by a magnificent staircase

  Beth Palma Keller Williams Realty

  5 Gabriels Dr, Chester, NY 10918
• 

  

  /50

  $1,300,000

  • 4 Beds
  • 2.5 Baths
  • 3,955 Sq Ft

  90 Main St, Chester, NY 10918

  "The House on the Hill" Proudly offered for the first time in over 70 years. This expansive and character-rich home overlooks the heart of the village while offering nearly 10 acres of space, privacy, and endless potential. Set across three separate parcels totaling 9.68 acres, the property features a main house with approximately 4,000 sq ft, a charming 2-bedroom guest cottage, a large dairy

  STEVEN WROBEL JR. Serhant LLC

  90 Main St, Chester, NY 10918
• 

  

  /35

  $1,650,000

  • 10 Beds
  • 6.5 Baths
  • 3,512 Sq Ft

  17 Bonnie Brook Rd, Monroe, NY 10950

  Over 20 sprawling acres with serene life, pond frontage, this is a true sanctuary. Located in Monroe-Woodbury this unique property offer two distinct residences and a spacious barn, providing endless possibilities. House 1: Contemporary Modern originally built in 1965. The first home boasts a generous 3,500+ sq ft of premium living space. Designed with a flexible layout, the home features two

  Pamela Henning Keller Williams Hudson Valley

  17 Bonnie Brook Rd, Monroe, NY 10950
• 

  

  /31

  $915,000

  • 3 Beds
  • 2.5 Baths
  • 2,302 Sq Ft

  2 Pine Hill Rd, Chester, NY 10918

  Listed on the National Register of Historic Places in the Sugar Loaf Historic District, this stunning Victorian is a Circa 1910 Sears Roebuck Kit Home (#118 The Clyde). Not only is this your dream home located in beautiful Sugar Loaf, NY, it is also zoned for extensive commercial use. Just a 1-minute walk to the quaint Sugar Loaf Arts & Crafts Village, cafes and Sugar Loaf Performing Arts

  Debbie Walsh SHAHAR Management LLC

  2 Pine Hill Rd, Chester, NY 10918
• 

  

  /35

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,484 Sq Ft

  576 Bull Mill Rd, Chester, NY 10918

  A fantastic opportunity for investors or future homeowners! This well-maintained home is set on a large, flat lot in a quiet, nature-filled neighborhood and offers strong rental potential with long-term flexibility. Inside, you’ll find a spacious living room, formal dining area, kitchen, and comfortable layout ideal for everyday living. Recent updates include fresh interior paint (2021), and a

  Lazar Schvimmer Blooming Realty

  576 Bull Mill Rd, Chester, NY 10918

Showing Results 1 - 40, Page 1 of 3

Why Live in Chester

Chester, NY, is a rural town with a rich history in the dairy industry, famously known as the birthplace of Philadelphia-style cream cheese. Located minutes from Hudson Valley attractions and retail centers in Woodbury, Chester offers a mix of small-town single-family homes and larger farmhouses on multi-acre lots. The town is accessible via Route 17, making it a convenient location with relatively lower home prices compared to nearby towns like Monroe. Chester features diverse recreational options, including the family-friendly Castle Fun Center with carnival rides, mini golf, and an indoor roller-skating rink. Carpenter Community Park serves as the town's central green space, offering a playground, picnic pavilion, and sports courts, while Goosepond Mountain State Park provides 1,500 acres of trails for hiking and horseback riding. The Orange Heritage Trail, accessible from the historic Erie Depot, runs almost 20 miles through the county. Local attractions include Legoland in nearby Goshen and the Capelli Sports Complex. Chester Mall offers grocery shopping at ShopRite and movies at Flagship Premium Cinemas, while the Chester Agricultural Center provides farm-fresh produce. Dining options include the Rustic Wheelhouse Restaurant, known for its Italian cuisine. Homes in Chester range from older, smaller houses to larger contemporary and Craftsman-style homes on spacious lots. The Windridge Mews condo subdivision offers two to three-bedroom units. The Chester Union Free School District serves the town, with Chester Elementary and Chester Academy providing various after-school activities. Commuters can reach New York City or Newark in about an hour and a half via Interstate 87 or Coach USA buses.

Learn more about living in Chester

Frequently Asked Questions

What is the average home price in Chester, NY?

Homes for sale in Chester, NY have an average home price of $594,693.

How many homes have sold over the last 12 months in Chester, NY?

139 homes have sold in Chester, NY over the last 12 months.

What are the most popular zip codes in Chester, NY?

The most popular zip codes in Chester, NY include 10918, 10990, 10950, 10924 and 10921.

How much do you need to make to afford a house in Chester?

The median home price in Chester is $549,000. If you put a 20% down payment of $109,800 and had a 30-year fixed mortgage with an interest rate of 6.56%, your estimated principal and interest payment would be $2,790 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $120K a year to afford the median home price in Chester.

How are the schools in Chester, NY?

Chester, NY has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Warwick Valley High School, Scotchtown Avenue School and Warwick Valley Middle School. Browse all the schools in Chester, NY to learn more.

Home Trends in Chester, NY

On average, homes in Chester, NY sell after 70 days on the market compared to the national average of 52 days. The median sale price for homes in Chester, NY over the last 12 months is $525,000, up 7% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$525,000

Median Single Family Sale Price

$581,000

Median Townhouse Sale Price

$327,500

Median 2 Bedroom Sale Price

$295,000

Median 1 Bedroom Sale Price

$185,000

Average Price Per Sq Ft

$266

Number of Homes for Sale

30

Last 12 months Home Sales

139

Months of Supply

2.60

Median List Price

$549,000

Median Change From 1st List Price

0%

Median Home Sale Price YoY Change

7%