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Chester, NY Homes for Sale with Garage

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  • /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

    Agent Photo

    Randolph Rogers

    eXp Realty

    (845) 681-2264

    16 Lori Ln, Chester, NY 10918
  • /13

    $711,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,092 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,

    Agent Photo

    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....

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    Erin Connolly

    Artisan Realty

    (845) 328-6250

    4703 Whispering Hills Unit 320, Chester, NY 10918
  • /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

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    Alexandra Zinko

    Century 21 Realty Center

    (845) 412-9860

    391 Bull Mill Rd, 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
  • /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
  • /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
  • /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
  • /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
  • /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

    • 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
  • /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
  • /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
  • /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
  • /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
  • /35

    $295,000

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft

    42 Eagle St, Monroe, NY 10950

    Two bedroom home in Lake Region Estates. This house features two bedrooms, open kitchen, living area with brick fireplace and a laundry area. Set on a half acre park like property there is also a garage that is used as a storage area, enclosed three season room and screened in porch with slate flooring. Access to lake right across from property. Large lot with municipal sewer allows for

    Richard Froehlich RE/MAX Benchmark Realty Group

    42 Eagle St, Monroe, NY 10950

Home Trends in Chester, NY

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%
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