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Chester Homes for Sale

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  • /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

    Agent Photo

    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
  • /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
  • /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
  • /45

    $850,000

    • 4 Beds
    • 2.5 Baths
    • 3,656 Sq Ft

    49 Stone Mountain Trail, Chester, NY 10918

    Stunning curb appeal. Unrivaled privacy. This 3-story, 3,650+ sq. ft. contemporary colonial is a true standout, set on over 7 acres in a private cul-de-sac, blending bold design with year-round comfort. From summer pool days to winter fun on gentle backyard slopes, this estate-style property delivers space, elegance, and adventure in one powerful package.Enter through a grand two-story foyer

    Leon Klein Keller Williams Hudson Valley

    49 Stone Mountain Trail, 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /49

    $1,500,000

    206 Greycourt Rd Unit 190, Chester, NY 10918

    **Endless Opportunities Await on This Rare 3.2-Acre Property!** ZONED COMMMERCIAL INDUSTRIAL USEFor the first time in over 50 years, this prime piece of real estate is hitting the market! Nestled right off Route 17 with unbeatable exposure, this unique 3.2-acre property offers **unlimited potential** for investors, developers, or those looking for a special place to call home. Featuring **four

    Susan McMullen eXp Realty

    206 Greycourt Rd Unit 190, Chester, NY 10918
  • /7

    $874,900

    • 4 Beds
    • 2 Baths
    • 2,466 Sq Ft

    651 Lakes Rd, Monroe, NY 10950

    Rare opportunity to purchase this breath taking one of a kind estate in Monroe that consists of three homes nestled on 3.5 stately landscaped acres affording you peace and privacy! Surrounded by the original stone walls of this compound, this unique oasis offers a huge 50,000-gallon gunite in-ground pool with Italian glass tile, patios overlooking the gorgeous park-like grounds, and a new

    Frank Golio Howard Hanna Rand Realty

    651 Lakes Rd, Monroe, NY 10950
  • /13

    $450,000

    • Land
    • 2.20 Acres
    • $204,545 per Acre

    6 Lookout Terrace, Chester, NY 10918

    Looking for just the right spot to build your dream home? Close to everything but also tucked away for peace and privacy. Spread out at the end of a cul de sac lies the land that can be the footprint for your new home. Make this your personal paradise or subdivide (7 lot potential) and sell as an investment. This 2.2 acre lot will be able to have municipal water and sewer. Conveniently located

    Gina Dudgeon Howard Hanna Rand Realty

    6 Lookout Terrace, Chester, NY 10918
  • /5

    $279,999

    • Land
    • 20 Acres
    • $13,875 per Acre

    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 can truly be a mini-estate with near full privacy plus MOUNTAIN VIEWS!! FULLY ENGINEERED with NATURAL GAS, curb cuts! ... Log and Go to walk lot... Site map in photos. This is one of only two remaining lots. Some wet-lands on the property. Drive way is not

    Karen Gauvin Our House Real Estate Group

    32 Mountainside Dr, Chester, NY 10918
  • /4

    $500,000

    • Land
    • 8 Acres
    • $59,648 per Acre

    30 Harding Way, Chester, NY 10950

    Opportunity is knocking on the door for all builders/investors in the Town Of Chester, Monroe - Woodbury School District. You buy 2 lots for the price of one. 30 Harding Way is SOLD TOGETHER with the lot next to it of 8.2 acres which is located in Section 15, Block 1, Lot 32. Subdivision potential.

    Ida Payne Keller Williams Realty

    30 Harding Way, Chester, NY 10950
  • /2

    $499,000

    • Land
    • 4.50 Acres
    • $110,889 per Acre

    1414 Kings Hwy, Chester, NY 10918

    5 Lot subdivision which has been engineered and submitted to Chester planning board for approvals with water and sewer. Not approved but in the process. Buyer must finish. Site plan in documents as well as addressed planning board comments. Additional Information: SoilType:Unknown,

    Joe Distelburger Keller Williams Realty

    1414 Kings Hwy, Chester, NY 10918
  • /2

    $500,000

    • Land
    • 0.83 Acre
    • $603,355 per Acre

    0 Main St, Chester, NY 10918

    Open commercial lot directly behind the existing Cumberland Farms and just to the east of the former Brookside carwash. Good use may be for a parking lot for a building built on 42 Brookside.

    Claude Brischoux Keller Williams Realty

    0 Main St, Chester, NY 10918
  • /2

    $295,000

    • 3 Beds
    • 1.5 Baths
    • 1,460 Sq Ft

    4 Maple Ln, Monroe, NY 10950

    FIX N FLIP OPPROTUNITY! With some TLC you can uncover this hidden gem! Uncover an incredible opportunity for first-time homebuyers and astute investors alike with this charming fixer-upper!!! Situated in a sought-after location, this property is full of potential. With a bit of tender loving care, you can turn this house into a beautiful home that showcases your unique style. Seize the chance to

    Joseph Rosenfeld Flag Realty Group

    4 Maple Ln, Monroe, NY 10950
  • /2

    $1,499,000

    • Land
    • 100 Acres
    • $14,990 per Acre

    0 Kings Hwy Unit ONEH6335680, Chester, NY 10918

    Located in the sought after Warwick Valley School District, here is your opportunity to develop pristine land on the corner of Kings Highway and Ridge Rd. in Chester, just outside the hamlet of Sugarloaf and minutes to the Village of Warwick, both offering restaurants, shops, live entertainment and more! With rolling hills and views of Sugarloaf Mountain, this untouched property offers many

    Kimberly Corkum Keller Williams Realty

    0 Kings Hwy Unit ONEH6335680, Chester, NY 10918
  • /8

    $5,500,000

    • Land
    • 186 Acres
    • $29,554 per Acre

    14 Johnson Rd, Chester, NY 10918

    This is an online only auction. Visit AARauctionsdotcom for complete details and bidding information. 186+/- vacant acres formed by six adjacent parcels selling "together, as-one." Seller has contemplated a warehousing development on paper for future development - or envision your plan. Route 94 is the main artery between Goshen (access to I-86, the current "Quickway," NYS

    Frank Pietrzak ABSOLUTE AUCTION AND REALTY INC

    14 Johnson Rd, Chester, NY 10918

Frequently Asked Questions Why Live in Chester

Is Chester a good place to live?
Chester is a good place to live. Chester is considered very car-dependent and somewhat bikeable. Chester has 4 parks for recreational activities. It has a median age of 41. The average household income is $137,158 which is above the national average. College graduates make up 39% of residents. A majority of residents in Chester are home owners, with 21.5% of residents renting and 78.5% of residents owning their home. A local real estate agent serving Chester can help you decide if this neighborhood is the right one for you. Learn more on our Chester neighborhood guide.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $467,343. If you put a 20% down payment of $93,500 and had a 30-year fixed mortgage with an interest rate of 6.74%, your estimated principal and interest payment would be $2,420 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $104K a year to afford the median home price in Chester. The average household income in Chester is $137K.
What are the best public schools in Chester?
The best public schools that serve Chester are:
What are the best private schools in Chester?
The best private schools that serve Chester are:
What are the most popular zip codes in Chester, Chester, NY?
The most popular zip codes in Chester, Chester, NY include 10918, 10990, 10950, 10924 and 10921.
What are the most popular neighborhoods near Chester, Chester, NY?
The most popular neighborhoods near Chester, Chester, NY are Blooming Grove, Hamptonburgh, Woodbury, Wallkill and New Windsor.

Home Trends in Chester, NY

Housing Trends

Median Sale Price
$454,160
Median Single Family Sale Price
$454,160
Median Townhouse Sale Price
$292,465
Median 2 Bedroom Sale Price
$699,000
Median 1 Bedroom Sale Price
$412,000
Average Price Per Sq Ft
$340
Number of Homes for Sale
16
Last 12 months Home Sales
108
Months of Supply
1.80
Median List Price
$467,343
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
14%
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