29

Chester, NY Homes for Sale under $1,000,000

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  • /49

    $700,000

    • 4 Beds
    • 2.5 Baths
    • 3,296 Sq Ft

    13 Bianca Blvd, Chester, NY 10918

    Gracious Colonial home features the best of the traditional style with the appeal of a contemporary open floor plan in the kitchen - family room area. Meticulously maintenance and stylish updates create easy living spaces that are great for daily relaxation as well as entertainment. The full-length deck, large seating area around the fire pit and expansive yard provide outdoor areas to relax,

    Theresa Powers

    Keller Williams Realty

    13 Bianca Blvd, Chester, NY 10918
  • /36

    $749,900

    • 4 Beds
    • 4 Baths
    • 3,080 Sq Ft

    20 Mountainside Dr, Chester, NY 10918

    20 Mountainside Drive, Chester, NY offers a spacious Colonial-style single-family home on approximately 1.6 acres with 4 bedrooms, 2 full baths, 2 half baths, 10 total rooms, and approximately 3,080 sq. ft. of above-ground living space. Built in 2021, this Chester residence features central cooling, gas heat, a full basement, fireplace, covered porch, patio, and Attached garage. Located in Orange

    Agent Photo

    Randolph Rogers

    eXp Realty

    20 Mountainside Dr, Chester, NY 10918
  • /37

    $789,900

    • 5 Beds
    • 4 Baths
    • 4,697 Sq Ft

    19 Grand View Terrace, Chester, NY 10918

    Welcome to 19 Grand View Terrace in Chester, NY, an impressive Colonial offering approximately 4,697 square feet, five bedrooms, and four full bathrooms. Set on approximately 0.42 acres, this expansive Orange County residence provides the space, comfort, and flexibility needed for everyday living, entertaining, working from home, and hosting guests. The generous interior features multiple living

    Agent Photo

    Randolph Rogers

    eXp Realty

    19 Grand View Terrace, Chester, NY 10918
  • /50

    $990,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,955 Sq Ft

    1 Oakland Ave, Chester, NY 10918

    Welcome to Brook Farm - Village of Chester, New York - Circa 1851 - 6.8 Acres. There's a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of

    Agent Photo

    Christina Rowan

    Howard Hanna Rand Realty

    1 Oakland Ave, Chester, NY 10918
  • /30

    $750,000

    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft

    1 Sanford Ave, Chester, NY 10918

    Welcome to 1 Sanford Avenue, a beautifully designed 4-bedroom, 3-bath Bilonial offering over 2,200 square feet of thoughtfully finished living space in Chester. The inviting exterior features a welcoming entry, attached 2-car garage, and attractive curb appeal.Inside, the open-concept layout is enhanced by soaring high ceilings, hardwood floors throughout, and a tiled foyer. The spacious

    Danielle Hinton Redfin Real Estate

    1 Sanford Ave, Chester, NY 10918
  • /2

    $750,000

    • 5 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    3 Hilltop Ln, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

    Moshe Kaufman MK Realty Inc

    3 Hilltop Ln, Chester, NY 10918
  • /5

    $759,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,250 Sq Ft

    90 Pewter Cir, Chester, NY 10918

    This beautiful custom home is planned to be built in the highly sought-after Sugar Loaf area, offering the convenience of municipal water and sewer. The main level welcomes you with warm hardwood floors and a kitchen featuring a choice of elegant granite or quartz countertops, a stainless steel appliance package, a center island perfect for meal preparation, and a spacious dining area with a

    Carla Terranova Keller Williams Realty

    90 Pewter Cir, Chester, NY 10918
  • /7

    $900,000

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

    651 Lakes Rd, Monroe, NY 10950

    Rare opportunity to purchase this gorgeous property that consists of 3 homes nestled on 3.5 beautiful acres. The main Colonial residence has been gutted and will need to be renovated/rebuilt, however, you can live in one of the additional two residences while you renovate! The 2nd residence called the “stone cottage” has 2 fieldstone fireplaces, a full kitchen, a vaulted ceiling in the bedroom, a

    Sandra Spector Howard Hanna Rand Realty

    651 Lakes Rd, Monroe, NY 10950
  • /46

    $839,000

    • 4 Beds
    • 4 Baths
    • 2,707 Sq Ft

    34 Boville Ct, Chester, NY 10918

    Welcome to 34 Boville Court, a stunning, fully updated farmhouse colonial tucked away on a peaceful cul-de-sac and set on just shy of two acres. Thoughtfully designed with timeless style and modern functionality, this completely move-in-ready home offers an exceptional blend of space, comfort, and sophistication. Step inside to beautiful hardwood floors and a bright, inviting layout made for both

    Jillian Laga Keller Williams Valley Realty

    34 Boville Ct, Chester, NY 10918
  • /3

    $750,000

    • 5 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    2 Boville Ct, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

    Moshe Kaufman MK Realty Inc

    2 Boville Ct, Chester, NY 10918
  • /36

    $750,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    985 Craigville Rd, Chester, NY 10918

    Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home.Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday

    DAVID DEBERARDINIS Serhant LLC

    985 Craigville Rd, Chester, NY 10918
  • /49

    $749,999

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,718 Sq Ft

    58 Nancy Ln, Chester, NY 10918

    Imagine ending every day watching the sun set from your front porch, with breathtaking views that change beautifully through every season. Sunset views, a fenced backyard, brand-new Trex deck, above-ground pool, home office, and the flexibility of **four sleeping spaces** make this property truly stand out. Perched atop the highly sought-after Fieldcrest subdivision, this stunning Colonial is

    Gina Dudgeon Howard Hanna Rand Realty

    58 Nancy Ln, Chester, NY 10918
  • /9

    $879,900

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

    1414 Kings Hwy, Chester, NY 10918

    Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with

    Carla Terranova Keller Williams Realty

    1414 Kings Hwy, Chester, NY 10918
  • /20

    $894,000

    $105K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,535 Sq Ft

    220 Oxford Rd, Chester, NY 10918

    220 Oxford Road is a Truly Impressive Property! Offering over 3,500 sq ft of beautifully maintained living space, this home features 3 bedrooms plus an additional upper-level room, 3 full baths, and 1 half bath. Spacious living room, stunning family room, and a practical, well-designed kitchen. The home showcases elegant finishes throughout along with brand new flooring that adds a fresh modern

    Moche Halpern Blooming Realty

    220 Oxford Rd, Chester, NY 10918
  • /2

    $725,000

    • 3 Beds
    • 2.5 Baths
    • 2,677 Sq Ft

    1 Arborvitae Ct, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 9 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

    Moshe Kaufman MK Realty Inc

    1 Arborvitae Ct, Chester, NY 10918
  • /50

    $750,000

    • 5 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    3 Boville Ct, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

    Dovid Hoffman MK Realty Inc

    3 Boville Ct, Chester, NY 10918
  • /7

    $900,000

    • 4 Beds
    • 2.5 Baths
    • 2,588 Sq Ft

    60 Whitetail Run, Chester, NY 10918

    Beautifully maintained Colonial set on a picturesque and private property offering the perfect blend of comfort, space, This spacious home features an inviting layout with generously sized rooms, hardwood flooring, elegant moldings, and abundant natural light throughout. The heart of the home is the oversized eat-in kitchen with granite countertops, extensive cabinetry, pantry space, and

    Isaac Rottenberg Realty Blue Corp

    60 Whitetail Run, Chester, NY 10918
  • /42

    $849,900

    • 4 Beds
    • 3 Baths
    • 2,370 Sq Ft

    2 Primrose Ln, Chester, NY 10918

    Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining.Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and

    Janet Rendle Weichert Realtors

    2 Primrose Ln, Chester, NY 10918
  • /34

    $949,000

    $50K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,136 Sq Ft

    12 Damian Ct, Chester, NY 10918

    Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

    Elimelech Kremer MS Realty Group USA, Inc

    12 Damian Ct, Chester, NY 10918
  • /43

    $949,000

    • 4 Beds
    • 2.5 Baths
    • 3,332 Sq Ft

    19 Bull Mine Rd, Chester, NY 10918

    Set on 2.3 acres in Chester, this impressive property offers space, versatility, and scenic surroundings. The residence features approximately 3,332 square feet of living space with 4 bedrooms, 2 full baths and 1 half bath, thoughtfully designed for comfortable everyday living and entertaining. Interior highlights include generously sized living areas, a fireplace, abundant natural light, and

    James Cosenza BHG Real Estate Green Team

    19 Bull Mine Rd, Chester, NY 10918
  • /8

    $869,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    10 Well Sweep Ln, Chester, NY 10918

    Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with

    Carla Terranova Keller Williams Realty

    10 Well Sweep Ln, Chester, NY 10918
  • /35

    $999,999

    • 5 Beds
    • 2.5 Baths
    • 4,772 Sq Ft

    2 Garnett Hill Rd, Chester, NY 10918

    A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5

    Rachel Baruchov Platinum Realty Associates

    2 Garnett Hill Rd, Chester, NY 10918
  • /35

    $875,000

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

    49 Stone Mountain Trail, Chester, NY 10918

    Escape to your own private retreat at 49 Stone Mountain Trail. Tucked away on more than 7 acres with mountain views, this contemporary home delivers the perfect balance of comfort, space, and outdoor enjoyment. Imagine mornings filled with sunlight streaming through oversized windows, evenings gathered around the stone fireplace, and summers spent relaxing by the in-ground pool surrounded by

    Arya Rabinovits eRealty Advisors, Inc

    49 Stone Mountain Trail, Chester, NY 10918
  • /5

    $850,000

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

    5 Hilltop Ln, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new colonial-style residence invites you in with 12 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail

    Moshe Kaufman MK Realty Inc

    5 Hilltop Ln, Chester, NY 10918
  • /2

    $750,000

    • 5 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    1 Hilltop Ln, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

    Moshe Kaufman MK Realty Inc

    1 Hilltop Ln, Chester, NY 10918
  • /36

    $875,000

    • 3 Beds
    • 2.5 Baths
    • 2,302 Sq Ft

    2 Pine Hill Rd, Chester, NY 10918

    The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. The Conklin House, a classic 1908 Queen Anne Victorian, stands as a commanding presence at the edge of the historic Village of Sugar Loaf. The home has always been used residentially but zoning permits commercial usage as well. Originally ordered from the

    Richard Ellis Ellis Sotheby's Intl Realty

    2 Pine Hill Rd, Chester, NY 10918
  • /49

    $785,000

    $14K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 5,403 Sq Ft

    4 Debbie Ct, Chester, NY 10918

    Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in desirable Chester. Offering the perfect blend of space, comfort, privacy, and lifestyle, this impressive property is surrounded by natural beauty while remaining conveniently close to shopping, dining, major highways, and the scenic Stewart State Forest.From the moment you arrive, you’ll appreciate

    Joseph Rosenfeld Flag Realty Group

    4 Debbie Ct, Chester, NY 10918
  • /36

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 3,070 Sq Ft

    197 Oxford Rd, Chester, NY 10918

    Welcome to this beautifully charming Center Hall Colonial, privately set back from the road on a picturesque property with a tranquil man-made pond, fountain, and inviting wrap-around front porch. This spacious home offers the perfect balance of classic elegance and comfortable everyday living. The thoughtfully designed floor plan features a formal living room that flows seamlessly into the warm

    Regina Carmel Howard Hanna Rand Realty

    197 Oxford Rd, Chester, NY 10918
  • /50

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 2,516 Sq Ft

    3 Garnett Hill Rd, Chester, NY 10918

    This well-maintained 4-bedroom, 2.5-bath home on 3 private acres is anchored by an expansive 3-tier Trex deck system and an on ground pool with 8-foot deep end, complemented by a sun deck and pool-surround walkway. The 2,516 square-foot home features 9-foot ceilings with wood molding, with hardwood floors and tile throughout the main floor. The main floor flows from a welcoming foyer through the

    Jacob Fried Keller Williams Realty

    3 Garnett Hill Rd, Chester, NY 10918

Home Price Trends

Median Sale Price
$500,000
Median Single Family Sale Price
$664,500
Median Townhouse Sale Price
$320,000
Median 2 Bedroom Sale Price
$310,000
Median 1 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$273
Number of Homes for Sale
69
Last 12 months Home Sales
83
Months of Supply
10.00
Median List Price
$599,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-5%
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