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
• 

  

  

  /29

  $369,000

  • 3 Beds
  • 2.5 Baths
  • 1,585 Sq Ft

  252 Heritage Ln, Monroe, NY 10950

  Welcome to this beautifully maintained 3 bedroom, 2.5-bath townhouse located in a highly sought after community within the Monroe-Woodbury School District. This move-in ready home features an open-concept main level with a spacious living room and kitchen area, perfect for entertaining. Enjoy the convenience of private in-unit laundry and assigned parking, with plenty of additional parking

  Brenda Wiley Howard Hanna Rand Realty

  252 Heritage Ln, Monroe, NY 10950
• 

  

  

  /50

  $995,000

  • 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
• 

  

  

  /50

  $975,000

  • 4 Beds
  • 2.5 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
• 

  

  

  /42

  $899,000

  • 5 Beds
  • 4 Baths
  • 4,496 Sq Ft

  10 Spectrum Dr, Chester, NY 10918

  Serene Country Retreat in an Upscale Chester Neighborhood!Set on over 5 peaceful acres with sweeping mountain views, this stunning contemporary home offers the perfect mix of style, comfort, and privacy. With 4 bedrooms and 4 bathrooms, the layout is ideal for both everyday living and effortless entertaining.The sun-drenched living room is a true showpiece—featuring dramatic cathedral

  David Hopstein eRealty Advisors, Inc

  10 Spectrum Dr, Chester, NY 10918
• 

  

  /35

  $789,000

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

  48 Brennan Ct, Chester, NY 10918

  Open and sun filled 4 BR, 2 1/2 bath Colonial is set on beautifully landscaped 5 acre grounds on a private cul de sac! 2 story foyer! Soaring ceilings in family room with large custom window and gas fireplace! Formal LR and DR, vaulted Great room! Kitchen has granite counters, stainless steel appliances, and lots of cabinets and opens to eating area with sliders to large deck with pergola!

  Linda Clark Hudson Valley Griffith

  48 Brennan Ct, Chester, NY 10918
• 

  

  /49

  $649,000

  • 4 Beds
  • 2.5 Baths
  • 2,402 Sq Ft

  9 June Rd, Chester, NY 10918

  Welcome to 9 June Road, a rare gem offering 3,122 square feet of well-designed living space in the heart of the Village of Chester.From the moment you arrive, the curb appeal draws you in with a classic rocking chair front porch and custom pavers lining the driveway and walkways. Step into a grand open foyer with a formal living room to the right and an elegant dining room to the left,

  Jason Madison eXp Realty

  9 June Rd, Chester, NY 10918
• 

  

  /48

  $699,000

  • 4 Beds
  • 2 Baths
  • 3,330 Sq Ft

  114 Old Mansion Rd, Chester, NY 10918

  Charming Colonial with 4 Bedrooms on Nearly an Acre – Prime Location!Welcome to this beautifully maintained Colonial-style home nestled on a generous 0.92-acre lot, offering space, comfort, and convenience. This freshly painted home features 4 spacious bedrooms, 2 full bathrooms, and a versatile layout perfect for modern living.The first floor boasts gleaming hardwood floors, a

  Hershel Lowy Master Realty Group Inc.

  114 Old Mansion Rd, Chester, NY 10918
• 

  

  /43

  $699,000

  • 5 Beds
  • 5.5 Baths
  • 5,403 Sq Ft

  4 Debbie Ct, Chester, NY 10918

  Experience unparalleled luxury and spaciousness in this stunning 5400 sq. ft. property, where every corner is designed for both elegance and practicality!! With expansive living areas, high-end finishes, and modern amenities, this home is perfect for entertaining or enjoying quiet family moments. Embrace a lifestyle of comfort and sophistication in a space that truly feels like a retreat all year

  Joseph Rosenfeld Flag Realty Group

  4 Debbie Ct, Chester, NY 10918
• 

  

  /45

  $699,900

  • 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 one-of-a-kind custom-built Country Contemporary home perfectly set on a private 2.3-acre hilltop. This unique property offers a rare blend of privacy, space, and convenience, just minutes from the NYS Thruway, nearby state parks, and only 45 minutes to New York City.The bright, open floor plan is designed to welcome natural light into every room.

  Ammar Iqbal eXp Realty

  65 Oxford Springs Rd, Chester, NY 10918
• 

  

  /37

  $749,000

  • 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
• 

  

  /48

  $949,000

  • 4 Beds
  • 3.5 Baths
  • 3,929 Sq Ft

  7 Gabriels Dr, Chester, NY 10918

  Don’t miss this opportunity to own a beautifully designed Colonial on 3.9 acres in a child-safe cul-de-sac, built with craftsmanship, comfort, and connection to nature in mind. Offering 3,929 sq ft of living space across 10 well-appointed rooms, this 4-bedroom, 3.5-bath home is very well maintained and features a spacious kitchen with granite countertops and stainless steel appliances—perfect for

  Chaim Weiss Exit Realty Venture

  7 Gabriels Dr, Chester, NY 10918
• 

  

  /42

  $750,000

  • 3 Beds
  • 2 Baths
  • 2,020 Sq Ft

  1711 Kings Hwy, Chester, NY 10918

  Nestled amidst the tranquil woods of Chester, NY, this stunning contemporary home offers a perfect sanctuary for those seeking a harmonious blend of modern design and natural beauty. The moment you step inside, floor-to-ceiling windows reveal breathtaking wooded vistas, flooding the interior with natural light and creating a seamless connection between indoor comfort and outdoor serenity. This

  Carmela Lopez Borrazas Keller Williams Realty

  1711 Kings Hwy, Chester, NY 10918
• 

  

  /32

  $325,000

  • 2 Beds
  • 1.5 Baths
  • 1,086 Sq Ft

  3107 Whispering Hills, Chester, NY 10918

  Whispering Hills – Updated 2 Bedroom, 2 Bath Apartment-Style Unit! Spacious and stylish multi-level condo featuring an updated kitchen with stainless steel appliances, fireplace, and central A/C. Unique layout with bedrooms and baths on separate levels for added privacy. The primary bedroom includes a walk-through closet with direct access to the bathroom. Enjoy the convenience of a 2-car garage,

  Hershel Lowy Master Realty Group Inc.

  3107 Whispering Hills, Chester, NY 10918
• 

  

  /37

  $365,000

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

  3911 Whispering Hills, Chester, NY 10918

  Whispering Hills – End Unit Condo! Beautifully updated 3 Bedroom, 2 Full Bath unit with 1-Car Attached Garage. Features an updated kitchen with quartz countertops, stainless steel appliances, and hardwood floors in the kitchen, dining area, and primary bedroom. Spacious living room with cathedral ceilings, electric fireplace with blower, and a decorative tiled accent wall. Primary suite includes

  Hershel Lowy Master Realty Group Inc.

  3911 Whispering Hills, Chester, NY 10918
• 

  

  /50

  $575,000

  • 4 Beds
  • 2.5 Baths
  • 2,144 Sq Ft

  18 Grant Dr, Monroe, NY 10950

  This bi-level home offers both charm and abundant sunshine, meticulously maintained by its original owners, showcasing obvious pride of ownership. The living and dining combination exudes luxury with its gleaming hardwood floors, while the kitchen is efficiently designed with a granite countertop, stainless steel appliances, a pantry, and a tiled backsplash. The three bedrooms on the first floor

  Donna Gennaro Howard Hanna Rand Realty

  18 Grant Dr, Monroe, NY 10950
• 

  /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
• 

  

  /21

  $86,500

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

  38 Granite Ridge Rd, Chester, NY 12817

  Seller financing available...2.84 acres of gently rolling property cleared for a potential future house or cabin. All stumps and undergrowth have been removed. Underground power to the site including a raised electrical pedestal. Driveway has been roughed-in and shed on-site for storage. 2019 travel trailer can be included for additional $10,000.00. (2019 Jay Flight B174BH) Road maintained

  Walter Swartz Gallo Realty ADK Inc

  38 Granite Ridge Rd, Chester, NY 12817
• 

  

  /28

  $485,000

  • 2 Beds
  • 2.5 Baths
  • 1,696 Sq Ft

  212 Sugarloaf Mountain Rd, Chester, NY 10918

  Picture your mountain retreat in this farmhouse built in 1900, blending historic charm with modern potential, set in the scenic Warwick Valley. Just two miles from Sugar Loaf’s artisan shops and dining, this 2-bedroom home offers tranquility and an express bus to NYC.Enter the living room, where exposed beams, hardwood floors, and a fireplace create a cozy feel. Sliding doors lead to a back

  Luisa Figlia BHG Real Estate Green Team

  212 Sugarloaf Mountain Rd, Chester, NY 10918
• 

  

  /43

  $539,999

  • 4 Beds
  • 2 Baths
  • 1,758 Sq Ft

  10 Tulip Ln, Monroe, NY 10950

  Welcome to this meticulously maintained 4-bedroom, 2-bath raised ranch in a quiet and friendly neighborhood, ideally situated in the highly rated Monroe-Woodbury School District. With thoughtful updates, quality finishes, and a flexible floor plan, this home is ready for its next chapter.The main level features gleaming hardwood floors throughout the living room, dining room, and three upper

  Philip Szumlaski Keller Williams Realty

  10 Tulip Ln, Monroe, NY 10950
• 

  

  /11

  $450,000

  • 4 Beds
  • 2 Baths
  • 1,872 Sq Ft

  15 Vivian Ln, Chester, NY 10918

  Desirable Family Neighborhood! This 4BR, 2BA Colonial Home is in sought-after Surrey Meadows. It's a great place to start or for a family looking for more space and bedrooms. The main floor has an open floor plan living/dining room. Updated kitchen with newer stainless steel appliances. First-floor laundry room. Both bathrooms are updated as well. The second floor has a master bedroom plus three

  Joseph Giglio Keller Williams Realty

  15 Vivian Ln, 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

  $589,000

  • 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
• 

  

  /43

  $499,000

  • 4 Beds
  • 2 Baths
  • 1,888 Sq Ft

  15 Mari Rd, Chester, NY 10918

  Move right into beautiful 15 Mari Road. Situated in a choice neighborhood and inclusive of Warwick Valley Schools, you will appreciate your newly updated home featuring mature landscaping, ample parking and close proximity to the arts and crafts hamlet of Sugarloaf. Stepping inside you will notice the brand-new gleaming hardwood floors throughout the main level. This level provides an open floor

  Nicholas Carbone HomeSmart Homes & Estates

  15 Mari Rd, Chester, NY 10918
• 

  

  /22

  $428,000

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  68 Southside Dr, Monroe, NY 10950

  Located in a prime Monroe, NY location with Monroe-Woodbury Schools, this wonderful home is surrounded by level, well groomed property and offers the perfect blend of classic charm and modern convenience with generous sized rooms throughout. A FIRST FLOOR BEDROOM & FULL BATH is ideal for flexible living arrangements. Step into the bright and airy living room, where natural light pours in and

  Carol Buchanan BHG Real Estate Green Team

  68 Southside Dr, Monroe, NY 10950
• 

  

  /22

  $1,499,999

  • 4 Beds
  • 4 Baths
  • 7,308 Sq Ft

  37 Main St, Chester, NY 10918

  Prime Investment Opportunity in the Heart of Chester Village – 37-39 Main Street & 9 Bank StreetNestled in the charming and historic Village of Chester, this fully updated mixed-use property presents an exceptional investment opportunity. Originally built in 1935, this rustic yet modernized building seamlessly blends timeless character with contemporary upgrades.The property features:• Fully

  James Feldhaus eXp Realty

  37 Main St, Chester, NY 10918
• 

  

  /28

  $474,900

  • 3 Beds
  • 1.5 Baths
  • 1,410 Sq Ft

  8 Hom St, Chester, NY 10918

  This well kept ranch located on a quiet cul-de-sac offers over 1400 sqft and boasts an open and welcoming floor plan with plenty of natural light, making it a warm and inviting space for both you and your guests. With three bedrooms, living room, family room and 1 and 1 1/2 baths, there's plenty of space for a growing family. Hardwood floors throughout creates a cohesive look and feel, while the

  Joao Rodrigues Preferred Properties Real Esta

  8 Hom St, Chester, NY 10918
• 

  

  /38

  $585,000

  • 4 Beds
  • 2.5 Baths
  • 2,516 Sq Ft

  7 Cambridge Cir, Monroe, NY 10950

  Move in ready Colonial with ADA Accessable features! Welcome to 7 Cambridge Circle, a perfect blend of colonial home living with access for ALL! This home welcomes you into a large entry foyer with HW floors, flowing into your formal living room to your right and your formal dining to your left. Past the large staircase, is your updated kitchen with new SS appliances and corian countertops. Off

  Alissa Taylor-Vetell Keller Williams Realty

  7 Cambridge Cir, Monroe, NY 10950
• 

  

  /23

  $549,000

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

  1 Winding Trail, Chester, NY 10918

  Welcome to 1 Winding Trail in the Town of Chester. This well-maintained home sits on a picturesque 1.2 acre lot located in the desirable Bull Mill Road area with Monroe-Woodbury Schools. With an easy flow, the home’s first floor boasts a spacious family room with fireplace, an office/den and a half bath. Walk-up a few steps into the large living room and a formal dining room both of which

  Donald Serotta Howard Hanna Rand Realty

  1 Winding Trail, Chester, NY 10918
• 

  

  /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
• 

  

  /47

  $596,000

  • 4 Beds
  • 2 Baths
  • 1,987 Sq Ft

  411 Prospect Rd, Chester, NY 10918

  Welcome to this spacious and well-laid-out home offering over 1,900 square feet of comfortable living space. With 4 bedrooms and 2 full bathrooms, there's room for everyone to enjoy. The upper level features two bedrooms and a full bath. One of the bedrooms offers generous space, perfect for a primary bedroom or flexible use. The eat-in kitchen is both functional and inviting—great for cooking,

  Dana Posner Howard Hanna Rand Realty

  411 Prospect Rd, Chester, NY 10918
• 

  

  /35

  $1,830,000

  • 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

  $925,000

  • 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
• 

  

  /40

  $345,000

  • 2 Beds
  • 1 Bath
  • 1,155 Sq Ft

  13 Dewey Rd, Chester, NY 12860

  Gorgeous Adirondack crafted home with unique rustic style. Many nice features including cathedral ceilings, S/S appliances, solid wood cabinets, full bath, living room with LP fireplace, 2 first floor bedrooms and a large sleeping loft bedroom. The home is offered with furnishings included! The woodwork throughout the house is exceptional with beautiful yellow southern pine wood floors, hemlock

  James Nester Cork Nester's True North Prop

  13 Dewey Rd, Chester, NY 12860
• 

  

  /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 3-bedroom, 2-bath 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

  Lazar Schvimmer Blooming Realty

  576 Bull Mill Rd, Chester, NY 10918
• 

  

  /50

  $2,800,000

  • 16 Beds
  • 11 Baths
  • 7,511 Sq Ft

  10 Damien Ct, Chester, NY 10918

  Don't miss this incredible opportunity to own 10 & 12 Damien Court, two stunning custom homes being sold together on nearly 6 acres of beautifully landscaped grounds located on a peaceful cul-de- sac of Chester.Together offering 16 bedrooms and 11 baths, these homes are perfect for multigenerational living, extended families, or investment potential. Enjoy gourmet eat-in kitchens, private suites,

  Elimelech Kremer MS Realty Group USA, Inc

  10 Damien Ct, Chester, NY 10918
• 

  

  /4

  $350,000

  • Land
  • 5 Acres
  • $68,627 per Acre

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

  Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

  Theresa Powers Keller Williams Realty

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
• 

  

  /5

  $74,900

  • Land
  • 1.79 Acres
  • $41,844 per Acre

  L4-5 Marina Rd, Chester, NY 12817

  This is two lots combined for better access and development and has beach rights to two beaches shown on map. HOA Owner's association fee includes beach maintenance. HOA board is working toward the possibility of installing a boat docksystem for the future. Presently there is space for non motorized craft on the beaches. Broker (John R. Palermo) is handling this property for his family's LLC

  John Palermo John R. Palermo

  L4-5 Marina Rd, Chester, NY 12817
• 

  

  /40

  $905,000

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

  11 Saddle Hill Rd, Chester, NY 10918

  Welcome to 11 Saddle Hill Road!This stunning brick Colonial seamlessly blends private luxury with everyday convenience. With over 5,000 square feet of beautifully finished living space, this home offers room for everyone to live, work, and relax in comfort. Step through the grand two-story foyer and take in the abundant natural light and gleaming hardwood floors that run throughout the home. The

  Alissa Taylor-Vetell Keller Williams Realty

  11 Saddle Hill Rd, Chester, NY 10918

Showing Results 1 - 40, Page 1 of 3

Why Live in Chester

Chester is a rural neighborhood known for its rich dairy farming history and as the birthplace of Philadelphia-style cream cheese. Located minutes from Hudson Valley attractions, Chester offers a variety of home styles, including single-family homes and larger farmhouses on multi-acre lots. The area is characterized by its park-heavy landscape, with Goosepond Mountain State Park providing 1,500 acres of trails for hiking and horseback riding. Carpenter Community Park serves as a central green space, featuring amenities like a playground, picnic pavilion, and sports courts. The Castle Fun Center offers family-friendly amusement with carnival rides, mini golf, and an indoor roller-skating rink. Chester's Erie Depot, a historic train station now a museum, connects to the Orange Heritage Trail, which runs nearly 20 miles through the county. Local attractions include Legoland, located five miles west in Goshen, and the Capelli Sports Complex, which offers various athletic facilities. Chester Mall provides shopping and entertainment options, while the Chester Agricultural Center offers farm-fresh produce. Dining options include the Rustic Wheelhouse Restaurant, known for its Italian cuisine. Homes in Chester range from brick ranch-style and midcentury split-levels to larger contemporary and Craftsman-style homes, with undeveloped lots also available. The Chester Union Free School District serves the area, offering programs like the Healthy Kids Before and After School Program. Commuters can reach New York City or Newark in about an hour and a half via Interstate 87.

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 $606,634.

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

137 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 12550, 10940, 10950, 10901 and 10956.

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

The median home price in Chester is $545,000. If you put a 20% down payment of $109,000 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $2,830 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $121K 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 50 days. The median sale price for homes in Chester, NY over the last 12 months is $525,000, up 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$525,000

Median Single Family Sale Price

$579,500

Median Townhouse Sale Price

$325,000

Median 2 Bedroom Sale Price

$290,000

Median 1 Bedroom Sale Price

$185,000

Average Price Per Sq Ft

$262

Number of Homes for Sale

32

Last 12 months Home Sales

137

Months of Supply

2.80

Median List Price

$545,000

Median Change From 1st List Price

0%

Median Home Sale Price YoY Change

6%