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

• 

  

  

  /9

  $49,000

  • Land
  • 4.00 Acres
  • $12,250 per Acre

  L17 Vanderwalker Rd, Chester, NY 12817

  Nestled in the heart of the Adirondacks, this peaceful 4-acre parcel offers a rare opportunity to own your own private slice of nature. The property features a quiet, wooded setting - ideal for a future homesite or a recreational getaway. A large existing shed structure on-site provides immediate utility for storage or workspace. Conveniently located just minutes from downtown Chestertown, Loon

  

  Zachary Layton

  Four Seasons Sotheby's International Realty

  (518) 608-2854

  L17 Vanderwalker Rd, Chester, NY 12817
• 

  

  

  /29

  $564,000 Open Sun 1PM - 4PM

  • 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
• 

  

  

  /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
• 

  

  /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
• 

  

  /50

  $849,900

  • 5 Beds
  • 3 Baths
  • 3,485 Sq Ft

  284 Bull Mill Rd, Chester, NY 10918

  Monroe's Stunning Mini Mansion Awaits Its New Owner!This exquisite home offers everything you've been dreaming of in an ideal location. Step into this 5-bedroom, 3-bath residence featuring a beautiful double-height entrance and a striking palladium window, welcoming you with its elegant double-sided luxury staircase.Before heading upstairs, prepare to be impressed by the spacious chef's

  Jayne Mangieri Keller Williams Valley Realty

  284 Bull Mill Rd, Chester, NY 10918
• 

  

  /37

  $675,000 Open Sat 11AM - 2PM

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

  9 Mount Ridge Ct, Monroe, NY 10950

  Tucked away on a peaceful cul-de-sac, this lovingly maintained 5-bedroom, 3-full-bath home offers 3,000 square feet of light-filled living space and a layout designed for comfort and flexibility. Owned by the original homeowner since day one, this property has been thoughtfully cared for and is ready for its next chapter.Inside, you’ll find big, bright rooms and an easy flow perfect for

  James Feldhaus eXp Realty

  9 Mount Ridge Ct, Monroe, NY 10950
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /48

  $875,000

  • 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
• 

  

  /45

  $700,000 Open House 8/09

  • 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
• 

  

  /11

  $40,000

  • Land
  • 1.80 Acres
  • $22,222 per Acre

  L27 Carriage Knolls Rd, Chester, NY 12817

  Seller financing now available! This property has been cleared and excavated in preparation for a new home. Site-plans are complete, perc tests are complete, septic plans have been completed, and an electric pedestal has been installed. (The small shed on-site is included as part of this transaction. Larger building also available separately and would need to be removed once the house certificate

  Walter Swartz Gallo Realty ADK Inc

  L27 Carriage Knolls Rd, Chester, NY 12817
• 

  

  /46

  $449,000

  • 4 Beds
  • 2 Baths
  • 1,788 Sq Ft

  57 Hubshop Rd, Chester, NY 10918

  Welcome to 57 Hubshop Rd, where comfort and convenience will make you feel right at home when walking through the door. The brand-new kitchen is a chef's dream featuring plenty of counter space, a center island and comfortable seating for all your guest. The living room is cozy and welcoming with many couches ready to embrace you after a long day. The family room is basked in sunshine, with a

  Avi Samet Avion

  57 Hubshop Rd, Chester, NY 10918
• 

  

  /26

  $370,000

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

  2503 Whispering Hills, Chester, NY 10918

  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. Don’t miss the opportunity to call this charming

  Sonia Gonzalez Keller Williams Hudson Valley

  2503 Whispering Hills, Chester, NY 10918
• 

  

  /39

  $525,000

  • 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
• 

  

  /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
• 

  

  /50

  $620,000

  • 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
• 

  /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

  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
• 

  

  /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
• 

  

  /45

  $650,000 Open Sun 1PM - 3PM

  • 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

  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

  $585,000

  • 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
• 

  

  /28

  $459,900

  • 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
• 

  

  /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

  $1,700,000

  • 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
• 

  

  /18

  $179,900

  • Land
  • 3.14 Acres
  • $57,293 per Acre

  2 Dixon Rd, Chester, NY 12817

  Fish, paddle, build! Your very own 509' of private frontage plus your own mini island on the Schroon River! Over 3 acre buildable lot with driveway in place and power at the road. Just south of the dam (no acess to Schroon Lake). Ideal location for fishing, paddling, rafting & swimming. Conveniently located to the Adirondack Northway and area amenities!

  Angie Mead Gallo Realty ADK Inc

  2 Dixon Rd, Chester, NY 12817
• 

  

  /5

  $46,900

  • Land
  • 7 Acres
  • $6,634 per Acre

  L30 Lane Rd, Chester, NY 12853

  You won't want to miss out on this opportunity! A little over 7 acres (2 parcels) in the heart of the Adirondacks. Close proximity to all the local lakes (Schroon Lake, Loon Lake, Brant Lake) & 10 minutes from Gore Mountain.

  Julia Pucciarelli Gallo Realty ADK Inc

  L30 Lane Rd, Chester, NY 12853

Showing Results 1 - 40, Page 1 of 2

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 $542,794.

Are home prices dropping in Chester?

Yes, home prices in Chester are down 29% in the last 12 months.

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

37 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 $574,900. If you put a 20% down payment of $115,000 and had a 30-year fixed mortgage with an interest rate of 6.74%, your estimated principal and interest payment would be $2,980 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $128K 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 61 days on the market compared to the national average of 70 days. The median sale price for homes in Chester, NY over the last 12 months is $565,000, down 26% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$565,000

Median Single Family Sale Price

$565,000

Median 2 Bedroom Sale Price

$345,000

Average Price Per Sq Ft

$268

Number of Homes for Sale

1

Last 12 months Home Sales

37

Months of Supply

0.30

Median List Price

$574,900

Median Change From 1st List Price

13%

Median Home Sale Price YoY Change

-26%