20

Chester, NY Houses for Sale with Garage

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  • /33

    $395,000

    • 3 Beds
    • 1 Bath
    • 1,038 Sq Ft

    12 Oak St, Chester, NY 10918

    Located in a peaceful area on a picturesque corner lot in the Village of Chester, this ranch style home in the Cherry Heights neighborhood has been meticulously well maintained with perennial flowers, mature trees, and privacy hedges. Inside, the home boasts a spacious living room with a large picture window that offers views of the front covered porch and a vibrant Japanese maple tree. The

    Agent Photo

    Jennifer Loprieno

    Howard Hanna Rand Realty

    (845) 539-1929

    12 Oak St, Chester, NY 10918
  • /50

    $799,900

    • 5 Beds
    • 4 Baths
    • 3,418 Sq Ft

    118 Murray Dr, Chester, NY 10918

    Nestled on 2.8 acres of lush, mature landscaping that borders the serene Goosepond Mountain State Park, this custom-designed contemporary ranch showcases a timeless blend of materials, with stone and brick construction lending both character and durability. Crafted by its original owners with meticulous attention to detail, the home offers a harmonious connection to its natural surroundings. A

    Agent Photo

    Brian Caplicki

    Keller Williams Hudson Valley

    (845) 409-8716

    118 Murray Dr, Chester, NY 10918
  • /50

    $859,900

    • 4 Beds
    • 3.5 Baths
    • 4,021 Sq Ft

    157 Creamery Pond Rd, Chester, NY 10918

    Welcome to Creamery Estates of Sugarloaf, where your dream home awaits just an hour’s drive from New York City. Nestled within walking distance of the charming downtown hamlet of Sugarloaf, this lovely residence is minutes away from schools, boutique shops, restaurants, grocery stores, the Sugar Loaf Performing Arts Center, wineries, breweries, apple orchards, the Appalachian trails, local

    Carla Terranova Keller Williams Realty

    157 Creamery Pond Rd, Chester, NY 10918
  • /39

    $650,000

    • 4 Beds
    • 2.5 Baths
    • 2,592 Sq Ft

    2 Laura Dr, Chester, NY 10918

    Fall in love with this stunning updated 4-bedroom Colonial located in Sugar Loaf Heights within the Warwick School District. You will feel like you apparated into the latest issue of Better Homes & Gardens the moment you enter. Agents - better schedule extra long showings as your clients will never want to leave! Step into the inviting living room featuring warm hardwood floors, soft recessed

    Virginia Corbett eXp Realty

    2 Laura Dr, Chester, NY 10918
  • /47

    $675,000

    • 4 Beds
    • 2.5 Baths
    • 2,608 Sq Ft

    174 Creamery Pond Rd, Chester, NY 10918

    Welcome to this beautifully maintained 4 bedroom, 2.5 bath Colonial nestled in the historic craft village of Sugar Loaf and award winning Warwick Valley Schools. This classic home offers timeless curb appeal, a spacious layout perfect for entertaining. The great room features an elegant stone fireplace, perfect for cozy evenings. A flowing layout with separate living, dining and great rooms

    Michele Tobin Keller Williams Realty

    174 Creamery Pond Rd, Chester, NY 10918
  • /42

    $719,000

    • 4 Beds
    • 4 Baths
    • 3,626 Sq Ft

    56 Sunset Ridge Rd, Monroe, NY 10950

    Welcome to 56 Sunset Ridge Road which sits by the private cozy cul-de-sac, a Magnificent backdrop on five luscious acres that envelope this tremendous center hall colonial. A beautiful driveway brings you home to your rocking chair front porch. Two story foyer gives way to the main level formal spaces. Living room, Dining Room, & a separate office leads you to an easy flowing, beautiful, recently

    Moses Schreiber MS Realty Group USA, Inc

    56 Sunset Ridge Rd, Monroe, NY 10950
  • /33

    $699,000

    • 4 Beds
    • 2.5 Baths
    • 2,452 Sq Ft

    138 Dug Rd, Chester, NY 10918

    Welcome home to this beautifully maintained Dutch Colonial situated on 2.6 serene acres within the desirable Monroe-Woodbury School District. This inviting home offers 4 spacious bedrooms, 2.5 bathrooms, and 2,452 square feet of well-appointed living space, thoughtfully designed for both comfort and functionality. Upon entering, you'll notice the natural light accentuating the gleaming hardwood

    Jake Garay Serhant LLC

    138 Dug Rd, Chester, NY 10918
  • /35

    $899,900

    • 4 Beds
    • 4 Baths
    • 4,854 Sq Ft

    4 Camelback Rd, Chester, NY 10918

    Stunning 4-Bedroom Home with Breathtaking Mountain Views!This is the one you've been waiting for! Nestled on a serene, tree-lined cul-de-sac, this luxurious 4-bedroom, 4-bath home offers the perfect blend of elegance, comfort, and spectacular mountain views.Step inside to a sun-drenched living room, where gleaming hardwood floors create an inviting ambiance. The spacious family room features a

    Veronica Goldzberg 2Win Realty LLC

    4 Camelback Rd, Chester, NY 10918
  • /36

    $624,242

    • 4 Beds
    • 2.5 Baths
    • 2,236 Sq Ft

    20 Hubshop Rd, Chester, NY 10918

    CAPTIVATING CAPE COD! 1.5 Private Acres! 4 Bedrooms! 2 1/2 Bathrooms! 1 Car Garage! Gorgeous Updated Eat In Kitchen with Granite Counter Tops, Stainless Steel Appliances & Breakfast Nook! Master Bedroom Suite with Walk In Closet Located on the First Floor! Living Room with Double Sided Fireplace! Gleaming Hard Wood Floors! New Carpeting! Recessed Lighting! Laundry Room! Full Basement! Rocking

    Amanda Dnistrian ARC Realty 1 in Sales

    20 Hubshop Rd, Chester, NY 10918
  • /45

    $850,000

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

    49 Stone Mountain Trail, Chester, NY 10918

    Nestled in a peaceful and private cul-de-sac, this stunning three-story contemporary colonial offers the perfect blend of elegance, space, and modern comfort. Set on an over 7 acre expansive lot, this home features a sprawling front and backyard, ideal for outdoor activities year-round—whether it’s summer fun by the pristine inground pool or winter ice sliding across the gentle slopes. A 2-car

    Leon Klein Keller Williams Hudson Valley

    49 Stone Mountain Trail, Chester, NY 10918
  • /7

    $899,900

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

    651 Lakes Rd, Monroe, NY 10950

    Build and Customize your dream home today on this compound in Monroe, Only one of its kind! The owner/builder has three plans for you tochoose from starting at 2600 sq feet - 5000 sq feet. This elegant, multi-family property consists of 3 residences nestled on over 3.5 statelylandscaped acres affording you peace and privacy. Surrounded by the original stone walls of this compound, this

    Frank Golio Howard Hanna Rand Realty

    651 Lakes Rd, Monroe, NY 10950
  • /2

    $600,000 Coming Soon

    • 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
  • /26

    $475,000

    • 4 Beds
    • 2 Baths
    • 1,554 Sq Ft

    4 Wood Rd, Chester, NY 10918

    Welcome to this stunning 4 bedroom ranch situated in sought after Sugar Loaf! As you enter you'll notice the spacious family room with vaulted ceilings, fire place, and hardwood flooring. This home is full of many updates such as a central air system, updated main bathroom, Trex front porch, SS appliances, and new flooring / paint on the lower level. Enjoy entertaining and spending time on the

    Matthew Skowronski HomeSmart Homes & Estates

    4 Wood Rd, Chester, NY 10918
  • /31

    $549,000 Open Sat 2PM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,844 Sq Ft

    13 Tulip Ln Unit 4, Monroe, NY 10950

    Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the heart of Monroe, NY. This inviting property offers an ideal blend of comfort, functionality, and outdoor enjoyment. Step inside to discover a sun-filled living room, formal dining room, and an eat-in kitchen complete with granite countertops, stainless steel appliances, and sliding doors that open to a spacious

    Courtney Tablante Keller Williams Realty

    13 Tulip Ln Unit 4, Monroe, NY 10950
  • /36

    $395,000

    • 3 Beds
    • 2.5 Baths
    • 1,528 Sq Ft

    100 Marian Ct, Warwick, NY 10990

    Step into a MINT beautiful 3-bedroom end-unit Townhouse gem, perfectly perched with panoramic views in Kings Estates! This spacious townhouse is move-in ready and offers the ideal blend of space, privacy, and everyday convenience. Enjoy municipal water, sewer, natural gas, central air, and NO HOA fees. Just one hour to NYC, it’s a commuter’s dream and ideally situated. Inside, you’ll find a

    Jennifer DiCostanzo RE/MAX Town & Country

    100 Marian Ct, Warwick, NY 10990
  • /38

    $585,000

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft

    12 Bianca Blvd, Chester, NY 10918

    Charming Colonial with Endless Potential – Priced to Sell!This stately Colonial is bursting with character and waiting for the right owner to bring it back to life! Nestled in a desirable neighborhood, this home offers classic architectural details, generous living spaces, and a layout perfect for modern living. While it needs some TLC, the potential here is undeniable—original hardwood

    Aoife Freeman Howard Hanna Rand Realty

    12 Bianca Blvd, Chester, NY 10918
  • /50

    $490,000

    • 3 Beds
    • 2.5 Baths
    • 1,716 Sq Ft

    16 Ayr Rd, Chester, NY 10918

    3/31/25 Multiple offers received. Please submit your highest and best by Wednesday, April 2, at 5:00. Include in your offer how any potential appraisal gap will be handled. Thank you for your interest in this home.This beautifully situated ranch style home offers amazing views, privacy, and convenience. The kitchen window displays a huge backyard with beautiful greenery in the spring and

    Luanne McGann Century 21 Full Service Realty

    16 Ayr Rd, Chester, NY 10918
  • /27

    $319,000

    • 4 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    156 Hardscrabble Rd, Chester, NY 10918

    Attention Skiers and/or Lovers of the Adirondacks -- Enjoy this spacious and warm 4 bedroom home. Natural light enhances the beauty of this home. Master bedroom on main floor, country eat-in kitchen and dining room, new washer and dryer, garage doors. Attic above the mudroom with stairs going up to spacious storage area. Running and play fenced-in area for pets. Screened-in porch and glassed-in

    Carol Monroe Najer Realty

    156 Hardscrabble Rd, Chester, NY 10918
  • /33

    $569,000

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    92 Pickerel Rd, Monroe, NY 10950

    Year end gifts are always wonderful to receive. Welcome to 92 Pickerel road Monroe, New York. A meticulous home awaiting its new owners and features including 3 to 4 bedrooms, 2 full baths, hardwood flooring, recently installed windows, roof, and boiler. A large eat in custom kitchen with granite, stainless appliances and Sub-Zero refrigeration. Dining room is adjacent and well placed.

    Richard Wawrynek Howard Hanna Rand Realty

    92 Pickerel Rd, Monroe, NY 10950
  • /24

    $1,900,000

    • 6 Beds
    • 4.5 Baths
    • 3,512 Sq Ft

    17 Bonnie Brook Rd, Monroe, NY 10950

    PICTURE-PERFECT MINI-ESTATE ON 20.6 ACRES - Nestled on a sprawling 20.6-acre parcel, this remarkable mini-estate offers the perfect blend of tranquility and opportunity. The property includes a newly renovated home, a charming older house primed for renovation, and a classic 1900s barn, all set against the backdrop of your own private lake and stunning grounds. Step inside the beautifully

    Michael Canter Keller Williams Hudson Valley

    17 Bonnie Brook Rd, Monroe, NY 10950

Home Trends in Chester, NY

Home Trends

Median Price (12 Mo)
$493,650
Median Single Family Price
$555,000
Median Townhouse Price
$320,000
Median 2 Bedroom Price
$289,000
Median 1 Bedroom Price
$185,000
Average Price Per Sq Ft
$266
Number of Homes for Sale
24
Last 12 months Home Sales
132
Months of Supply
2.20
Median List Price
$499,000
Median Discount From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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