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Chester, NY Homes for Sale with Fireplace

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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
  • /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

    Agent Photo

    Alexandra Zinko

    Century 21 Realty Center

    (845) 412-9860

    391 Bull Mill Rd, 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /10

    $369,900

    • 3 Beds
    • 1.5 Baths
    • 1,376 Sq Ft

    264 Heritage Ln, Monroe, NY 10950

    Move-In Ready 3-Bedroom Condo in the Monroe-Woodbury School District. Discover comfort, convenience, and community in this 3-bedroom, 1.5-bath condo located in one of the most desirable areas of the Hudson Valley. The open-concept main level features a bright and spacious living room, a dining area, and a well-appointed kitchen—perfect for everyday living and entertaining. Upstairs, you’ll find

    Frank Golio Howard Hanna Rand Realty

    264 Heritage Ln, Monroe, NY 10950
  • /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
  • /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
  • /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
  • /45

    $650,000

    • 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 custom-built Country Contemporary set on a private 2.3-acre hilltop. This one-of-a-kind property offers the perfect balance of privacy, space, and convenience, just minutes from the NYS Thruway, state parks, and only 45 minutes to NYC.Inside, the bright open floor plan is filled with natural light, featuring rich hardwood floors, custom

    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

    $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
  • /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
  • /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
  • /70

    $299,900

    • Land
    • 166 Acres
    • $1,807 per Acre

    L9 Atateka Rd, Chester, NY 12817

    This is a fantastic opportunity to own your own patch of beautiful Adirondack woods, nearly 166 acres, complete with a perennial stream, beaver pond, mature timber, and plenty of wild game. Use this property as your own recreational playground or build your dream home or camp in this peaceful, wooded retreat. The Potter Brook Timberlands property has abundant large, mature native tree

    John O'Donnell Timberland Realty

    L9 Atateka Rd, Chester, NY 12817
  • /78

    $699,900

    • Land
    • 337 Acres
    • $2,077 per Acre

    L 13.2 Friends Lake Rd, Chester, NY 12817

    With nearly 2,200 feet of frontage along the Upper Hudson River, a wild, whitewater backcountry river, and immediate access to nearly 1,600 acres of State Forest Preserve, the Hudson River Woods & Wildwater property is the "complete package" of Adirondack property. With over 4,500 feet of road frontage (with electric) on Friends Lake Road, it's an ideal location for a camp, second

    John O'Donnell Timberland Realty

    L 13.2 Friends Lake Rd, Chester, NY 12817
  • /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
  • /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
29
Last 12 months Home Sales
139
Months of Supply
2.50
Median List Price
$549,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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