25

Chester Houses for Sale

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  • /29

    $550,000 Open Sun 12PM - 2PM

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

    391 Bull Mill Rd, Chester, NY 10918

    Motivated Seller!! 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

    Agent Photo

    Alexandra Zinko

    Century 21 Realty Center

    (845) 412-9860

    391 Bull Mill Rd, 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,

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    Shaylene Neumann

    Houlihan Lawrence Inc.

    (329) 208-1641

    12 Juniper Ln, Monroe, NY 10950
  • /33

    $711,000

    • 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,

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    Dulce M Ferrera

    Keller Williams Hudson Valley

    (845) 203-6068

    2 Dawn Ct, Chester, NY 10918
  • /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
  • /44

    $674,999 Open Sun 11AM - 1PM

    • 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
  • /40

    $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
  • /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
  • /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
  • /37

    $724,000 Open Sun 12PM - 2PM

    • 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
  • /24

    $489,900

    • 4 Beds
    • 1.5 Baths
    • 1,570 Sq Ft

    22 Bridle Ln, Chester, NY 10918

    This well-maintained 4-bedroom raised ranch located in Surrey Meadows, is just a short walk to a town park and local schools. The home features an updated kitchen and bathrooms, a bright and functional layout, and 400 square feet of finished space in the basement with a family room, bedroom, storage and laundry area. Let’s not forget about the inviting sunroom—perfect for morning coffee,

    Jennifer Lucas Keller Williams Realty

    22 Bridle Ln, 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
  • /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
  • /26

    $225,000

    • 2 Beds
    • 1 Bath
    • 484 Sq Ft

    42 Heaton Rd, Monroe, NY 10950

    This quaint two-bedroom home is located in the lake region of Monroe. It is a short walk down Heaton rd. to Walton Lake. There is an enclosed porch when you enter the home that has bright sunny windows. The kitchen and living room are one open room. There is one bathroom, both bedrooms have nice size closets. Full attic with pull down stairs for storage. Great starter home or perfect for

    Maureen Schroder Keller Williams Valley Realty

    42 Heaton Rd, Monroe, NY 10950
  • /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
  • /37

    $569,999

    • 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
  • /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

    • 6 Beds
    • 4.5 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
  • /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
  • /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
  • /23

    $455,000

    • 3 Beds
    • 1 Bath
    • 1,561 Sq Ft

    33 Meadow Ave, Chester, NY 10918

    One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space.Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

    Ernie Acampora River Realty Services, Inc.

    33 Meadow Ave, Chester, NY 10918

Home Trends in Chester, NY

Housing Trends

Median Sale Price
$475,000
Median Single Family Sale Price
$569,999
Median Townhouse Sale Price
$335,000
Median 2 Bedroom Sale Price
$290,000
Median 1 Bedroom Sale Price
$185,000
Average Price Per Sq Ft
$269
Number of Homes for Sale
26
Last 12 months Home Sales
147
Months of Supply
2.10
Median List Price
$515,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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