Chester, NY Homes

/38
$327,000 Pending
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
2323 Whispering Hills Unit 213, Chester, NY 10918

Rare Opportunity in Whispering Hills! Discover this uniquely reimagined end-unit condo, expertly converted from a three-bedroom layout into a sprawling, sun-drenched two-bedroom retreat. This home is a masterclass in modern comfort, featuring eight brand-new Andersen windows and a matching Andersen door (2025) that perfectly frames spectacular, far-reaching horizon views. Much of the interior has

Luanne McGann

Century 21 Full Service Realty

(845) 516-8714

2323 Whispering Hills Unit 213, Chester, NY 10918
Explore Chester
/6
$2,100 Per Month
- 1 Bed
- 1 Bath
- 800 Sq Ft
- Condo for Rent
7 Kennedy Ln Unit 3, Monroe, NY 10950

Property Id: 2505575Welcome to this well-kept 1 bedroom + extra bonus room apartment located at — perfect for anyone needing a little extra space for a home office, guest room, or creative setup.•1 large bedroom + versatile bonus room•Private front & back entrances•Covered patio + backyard access•Small private yard space•Metal shed for extra storage•Off-street

(845) 604-9599

7 Kennedy Ln Unit 3, Monroe, NY 10950
$1,225,000 Sold Apr 17, 2026

10 Damian Ct, Chester, NY 10918
- 11 Beds
- 6.5 Baths
- 4,327 Sq Ft
- Built 2004
Last Sold Summary
- 11% Below List Price
- $283/SF
- 47 Days On Market
Current Estimated Value $1,359,100

Last Listing Agent Elimelech Kremer MS Realty Group USA, Inc

10 Damian Ct, Chester, NY 10918

/5
Not Listed For Sale

L34 Lane Rd, Chester, NY 12853
L34 Lane Rd, Chester, NY 12853

Last Sold Summary
- 27 Days On Market
- Last Sold Price $41,500
- Apr 28, 2025
Last Listing Agent Julia Pucciarelli Gallo Realty ADK Inc

/44
$450,000
- 4 Beds
- 2 Baths
- 1,642 Sq Ft
82 Southside Dr, Monroe, NY 10950

Welcome to 82 Southside Dr in Monroe — a beautifully renovated ranch-style home offering effortless one-level living in the highly sought-after Monroe-Woodbury School District. This 4-bedroom, 2-bath home features a versatile layout with an additional home office or den, ideal for remote work, a playroom, or guest space. Fully renovated from top to bottom, the home showcases brand-new flooring

Ammar Iqbal

eXp Realty

(329) 214-0985

82 Southside Dr, Monroe, NY 10950
/20
$15,805

Total Monthly Price
- 7 Beds
- 6 Baths
- Condo for Rent
45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918

The advertised rate of $15,806/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 13, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it

(845) 599-0724

45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918
/9
$43,000 Sold Oct 31, 2025

L17 Vanderwalker Rd, Chester, NY 12817
- Land
- 4 Acres
- $10,750 per Acre
Last Sold Summary
- 12% Below List Price
- 5 Days On Market
Last Listing Agent Zachary Layton Four Seasons Sotheby's International Realty

L17 Vanderwalker Rd, Chester, NY 12817

Est $232,549 Not Listed For Sale

495 Laroe Rd, Chester, NY 10918
- 3 Beds
- Built 2025
495 Laroe Rd, Chester, NY 10918

Last Sold Summary
- 38% Above List Price
- $83/SF
- 170 Days On Market
- Last Sold Price $168,000
- Dec 29, 2023
Last Listing Agent Dylan Piazza Howard Hanna Rand Realty

/41
$1,159,900
- 4 Beds
- 5 Baths
- 4,624 Sq Ft
16 Lori Ln, Chester, NY 10918

Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sac lot in the Monroe-Woodbury area of Orange County. This custom residence delivers the space, craftsmanship, and lifestyle today's relocation and move-up buyers are searching for, with approximately 4,624 square feet, refined architectural detail, mountain views, and seamless indoor-outdoor living. From the

Randolph Rogers

eXp Realty

(845) 493-2930

16 Lori Ln, Chester, NY 10918
/37
$5,300 Per Month
- 4 Beds
- 2 Baths
- 3,412 Sq Ft
- House for Rent
66 Murray Dr, Chester, NY 10918

Welcome to Refined Living — A Contemporary Ranch renovated for Elevated Year-Round Living with ease, entertainment and privacy! Perfectly set on 1.2 acres with Mountain views just one hour from New York City, this FULLY FURNISHED and fully equipped 3,412 square-foot home provides the convenience of one level living blended with the luxury of upscale design features. The bright and open Foyer

Tehillah Deslandes Howard Hanna Rand Realty

66 Murray Dr, Chester, NY 10918
$320,000 Sold Mar 11, 2026

2912 Whispering Hills, Chester, NY 10918
- 2 Beds
- 1 Bath
- 1,084 Sq Ft
- Built 1987
Last Sold Summary
- 5% Above List Price
- $295/SF
- 19 Days On Market
Current Estimated Value $304,383

Last Listing Agent Rebecca Matta-Candela Keller Williams Realty

2912 Whispering Hills, Chester, NY 10918

Not Listed For Sale

303 Sugarloaf Mountain Rd, Chester, NY 10918
- 4 Beds
- 3 Baths
- 2,287 Sq Ft
- Built 2024
303 Sugarloaf Mountain Rd, Chester, NY 10918

Last Sold Summary
- $306/SF
- 35 Days On Market
- Last Sold Price $700,000
- Jul 23, 2024
Last Listing Agent Courtney Tablante Keller Williams Realty

/9
$369,900
- 3 Beds
- 2.5 Baths
- 1,331 Sq Ft
3910 Whispering Hills, Chester, NY 10918

Welcome to 3910 Whispering Hills — a refined, turnkey townhome in one of Chester’s most desirable residential enclaves. This thoughtfully appointed 3-bed, 2.5-bath home blends classic suburban elegance with low-maintenance living. Set within a mature, amenity-rich community, you’ll enjoy direct access to commuter transit, shops, and parks while savoring the quiet privacy prized by Hudson Valley

Randolph Rogers

eXp Realty

(845) 957-9249

3910 Whispering Hills, Chester, NY 10918
/35
$4,300 Per Month
- 6 Beds
- 4.5 Baths
- 3,968 Sq Ft
- House for Rent
4 Ayr Rd, Chester, NY 10918

Welcome to 4 Ayr Court in Chester, NY — a spacious and beautifully maintained 6-bedroom, 4-bathroom home available for rent! Nestled on a quiet street, this impressive property offers the perfect blend of space, comfort, and convenience. Step inside to find a bright and inviting interior featuring generous living areas, ideal for both everyday living and entertaining. The expansive layout

Danielle Riggs Keller Williams Hudson Valley

4 Ayr Rd, Chester, NY 10918
$260,000 Sold Mar 11, 2026

2104 Whispering Hills, Chester, NY 10918
- 3 Beds
- 2.5 Baths
- 1,331 Sq Ft
- Built 1984
Last Sold Summary
- 13% Below List Price
- $195/SF
- 24 Days On Market
Current Estimated Value $274,041

Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

2104 Whispering Hills, Chester, NY 10918

Est $111,620 Not Listed For Sale

30 Mount Ridge Ct, Monroe, NY 10950
30 Mount Ridge Ct, Monroe, NY 10950

Last Sold Summary
- 22% Above List Price
- 49 Days On Market
- Last Sold Price $91,500
- Jul 29, 2024
Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

/32
$450,000
- 3 Beds
- 2 Baths
- 1,882 Sq Ft
5 Roggia Rd, Chester, NY 10918

Welcome to this spacious and versatile home nestled at a dead end st. in the desirable town of Chester. Offering an abundance of living space, this property is ideal for those seeking privacy, comfort, flexibility, and room to grow. The home features a functional layout with generously sized bedrooms, a bright and inviting living area, and a well-appointed kitchen designed for everyday living and

Nazma Sooknanan

Nazma Real Estate LLC

(845) 606-3972

5 Roggia Rd, Chester, NY 10918
/45
$2,490 Per Month
- 2 Beds
- 1.5 Baths
- 1,053 Sq Ft
- Townhouse for Rent
1208 Whispering Hills, Chester, NY 10918

Super Clean & Bright Rental in Whispering Hills. 2 Bedrooms, 1.5 Baths, 1 Car Garage with Central Air, Young Kitchen and Appliances, Laminate Flooring on 1st Floor with Laundry and updated Half Bath. Freshly Painted in 2022. Upstairs you will find Primary Bedroom with Vaulted Ceilings, Walk in Closet w/Organizers, Updated Full Bath, Skylight and Spacious Guest Room. Upstairs offers Carpeting.

Rosalie Cook Weichert Realtors

1208 Whispering Hills, Chester, NY 10918
$735,000 Sold Jul 21, 2025

189 Creamery Pond Rd, Chester, NY 10918
- 4 Beds
- 2.5 Baths
- 2,980 Sq Ft
- Built 2004
Last Sold Summary
- 5% Above List Price
- $247/SF
- 19 Days On Market
Current Estimated Value $740,086

Last Listing Agent Patricia Brady Keller Williams Realty

189 Creamery Pond Rd, Chester, NY 10918

Est $371,665 Not Listed For Sale

3815 Whispering Hills Dr, Chester, NY 10918
- 3 Beds
- 2.5 Baths
- 1,331 Sq Ft
- Built 1987
3815 Whispering Hills Dr, Chester, NY 10918

Last Sold Summary
- 6% Above List Price
- $263/SF
- 23 Days On Market
- Last Sold Price $350,000
- Apr 07, 2025
Last Listing Agent Frank Golio Howard Hanna Rand Realty

/48
$1,100,000
- 5 Beds
- 4 Baths
- 5,312 Sq Ft
53 Gibson Hill Rd, Chester, NY 10918

Tucked away on over 3 private acres, this recently renovated custom residence offers a rare blend of seclusion, craftsmanship, and elevated living. Surrounded by hundreds of acres of protected state land, the setting ensures unmatched privacy with direct access to nature, including trails that connect to the Appalachian Trail just beyond your backyard. A natural waterfall adds to the serene

Ammar Iqbal

eXp Realty

(845) 328-2396

53 Gibson Hill Rd, Chester, NY 10918
/26
$2,500 Per Month
- 2 Beds
- 1 Bath
- 1,084 Sq Ft
- Townhouse for Rent
2312 Whispering Hills, Chester, NY 10918

Welcome to the RENOVATED ASPEN MODEL END UNIT in the desirable Whispering Hills community! This stunning rental offers a blend of luxury finishes and resort-style living with an unbeatable location for NYC commuters. The unit features a Brand New Kitchen with a beautiful granite countertop and stainless-steel appliances, and a New Bathroom. Enjoy the spacious living room with a cozy fireplace and

Elena James Keller Williams Realty

2312 Whispering Hills, Chester, NY 10918
$290,000 Sold Apr 09, 2026

3308 Whispering Hills Dr, Chester, NY 10918
- 2 Beds
- 1.5 Baths
- 1,072 Sq Ft
- Built 1984
Last Sold Summary
- 3% Below List Price
- $271/SF
- 39 Days On Market
Current Estimated Value $289,036

Last Listing Agent Joseph Paoli Howard Hanna Rand Realty

3308 Whispering Hills Dr, Chester, NY 10918

Not Listed For Sale

3111 Whispering Hills Dr, Chester, NY 10918
- 3 Beds
- 2 Baths
- 1,316 Sq Ft
- Built 1987
3111 Whispering Hills Dr, Chester, NY 10918

Last Sold Summary
- $258/SF
- 50 Days On Market
- Last Sold Price $339,000
- Apr 01, 2025
Last Listing Agent Annmarie Kovacs Howard Hanna Rand Realty

/48
$730,000 Pending
- 4 Beds
- 3.5 Baths
- 2,780 Sq Ft
7 Park Place, Chester, NY 10918

Welcome to your private, wooded oasis! This charming home perfectly blends convenience with comfort, featuring an ideal layout for multi-generational living or guests with two bedrooms and a full bathroom on the main floor. A cozy wood insert is the heart of the main living space, creating both warmth and a wonderful ambiance on chilly evenings. Beyond the existing bedrooms, there is additional

Luanne McGann

Century 21 Full Service Realty

(845) 447-0221

7 Park Place, Chester, NY 10918
/10
$2,200 Per Month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- Townhouse for Rent
82 High St Unit 5, Chester, NY 10918

Very bright and spacious top-floor Penthouse apartment! Come see this open layout floorplan. The updated kitchen has a new stainless steel refrigerator and dishwasher. The Primary bedroom has large double closets and can accommodate a king-size bed. The living room/dining room combination is bright and sun-filled, with plenty of windows and an outside deck. You’ll appreciate the convenience of

Lynda Hoss Weichert Realtors

82 High St Unit 5, Chester, NY 10918
$323,500 Sold Aug 11, 2025

98 High St, Chester, NY 10918
- 4 Beds
- 1.5 Baths
- 1,360 Sq Ft
- Built 1950
Last Sold Summary
- 5% Below List Price
- $238/SF
- 35 Days On Market
Current Estimated Value $351,879

Last Listing Agent Zachary Foley eXp Realty

98 High St, Chester, NY 10918

Est $512,649 Not Listed For Sale

397 Bellvale Rd, Chester, NY 10918
- 2 Beds
- 2 Baths
- 1,452 Sq Ft
- Built 1983
397 Bellvale Rd, Chester, NY 10918

Last Sold Summary
- 8% Above List Price
- $327/SF
- 45 Days On Market
- Last Sold Price $475,000
- Apr 22, 2025
Last Listing Agent Juan Bautista Serhant LLC

/2
$425,000 Open House 5/17
- 3 Beds
- 2.5 Baths
- 1,331 Sq Ft
2722 Whispering Hills Unit 542, Chester, NY 10918

New beginnings offered in this light and bright completely updated end unit featuring two car garage, brand new floors, freshly painted, update kitchen with new stainless steel appliances and so much more. Located close to major highway, NYC bus and shopping. Club house with gym, basketball and tennis courts, playgrounds and 2 inground pools. Low taxes! Town and County, $1,110.66, Village

Erin Connolly-Frontino

Artisan Realty

(845) 932-1237

2722 Whispering Hills Unit 542, Chester, NY 10918
/32
$2,800 Per Month
- 4 Beds
- 1.5 Baths
- 1,605 Sq Ft
- House for Rent
98 Main St, Chester, NY 10918

Welcome to 98 Main St: a gracious Colonial in the center of the village of Chester!A huge "wrap-around" front porch greets you when you arrive. Once inside, you will be impressed with the "old world" charm of the stained-glass windows, dark wood trim, Hardwood floors and the pocket doors in the Living Room. Many large windows downstairs let in plenty of sunlight! Upstairs there are 4 nice

Eveline White Hudson Valley Griffith

98 Main St, Chester, NY 10918
$875,000 Sold Jun 13, 2025

157 Creamery Pond Rd, Chester, NY 10918
- 4 Beds
- 3.5 Baths
- 4,021 Sq Ft
- Built 2001
Last Sold Summary
- 2% Above List Price
- $218/SF
- 17 Days On Market
Current Estimated Value $872,070

Last Listing Agent Carla Terranova Keller Williams Realty

157 Creamery Pond Rd, Chester, NY 10918

Est $347,170 Not Listed For Sale

1110 Whispering Hills Dr, Chester, NY 10918
- 3 Beds
- 2.5 Baths
- 1,331 Sq Ft
- Built 1985
1110 Whispering Hills Dr, Chester, NY 10918

Last Sold Summary
- 4% Above List Price
- $252/SF
- 16 Days On Market
- Last Sold Price $335,000
- Jun 28, 2024
Last Listing Agent Yalitza Sepulveda Keller Williams Realty

/36
$395,000 Pending
- 3 Beds
- 2.5 Baths
- 1,694 Sq Ft
223 Eagleton Dr, Monroe, NY 10950

Welcome home to this tastefully updated and meticulously maintained 3 bedroom, 2.5 bath unit in a highly sought after community in the Monroe Woodbury school district. The Windridge community is clustered around ponds adding to the country feel. Located near the back of the cul-de-sac, this home features an open floorplan for easy living and entertaining. Step out of the sliding door in the

Theresa Powers

Keller Williams Realty

(329) 218-1935

223 Eagleton Dr, Monroe, NY 10950
/37
$3,650 Per Month
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- Apartment for Rent
408 Bull Mill Rd Unit 2, Chester, NY 10918

***Rare opportunity***Available April 1st for occupancy! Experience peaceful country living at 408 Bull Mill Rd, Unit 2, a Victorian-style retreat set on sprawling acreage and surrounded by nature. This 1,800 sq. ft. home offers exceptional privacy, quiet, and seclusion while providing the space and charm of a classic design. Inside, you’ll find three spacious bedrooms and two full bathrooms,

Robert Addon Keller Williams Realty

408 Bull Mill Rd Unit 2, Chester, NY 10918
$610,000 Sold Mar 12, 2026

44 Cedar Pond Ln, Chester, NY 10918
- 3 Beds
- 2 Baths
- 1,876 Sq Ft
- Built 1991
Last Sold Summary
- 2% Above List Price
- $325/SF
- 48 Days On Market
Current Estimated Value $637,142

Last Listing Agent Ammar Iqbal eXp Realty

44 Cedar Pond Ln, Chester, NY 10918

/33
Not Listed For Sale

78 Panther Mtn Rd, Chester, NY 12817
- 3 Beds
- 1 Bath
- 876 Sq Ft
- Built 1961
78 Panther Mtn Rd, Chester, NY 12817

Last Sold Summary
- $291/SF
- 68 Days On Market
- Last Sold Price $255,000
- Mar 03, 2025
Last Listing Agent Angie Mead Gallo Realty ADK Inc

/45
$570,000
- 4 Beds
- 2.5 Baths
- 1,916 Sq Ft
22 Cambridge Cir, Monroe, NY 10950

Impeccably maintained contemporary raised ranch in Lake Region Estates on prime corner lot, featuring an open floor plan ideal for everyday living and entertaining. Updated kitchen with center island, stainless steel appliances, and a bright garden window perfect for herbs and plants. Spacious living room offers a cathedral ceiling and oversized windows for abundant natural light. Dining area

Jade Oliverio

Howard Hanna Rand Realty

(329) 666-0425

22 Cambridge Cir, Monroe, NY 10950
/28
$2,900 Per Month
- 3 Beds
- 2.5 Baths
- 1,452 Sq Ft
- House for Rent
60 Evan Rd, Warwick, NY 10990

Please check this well maintained, clean and great size townhouse! It is nestled in the heart of Orange County with Warwick school district. This beautiful home is offering 3 bedrooms, 2 1/2 bathrooms, one car garage and a partial finished basement great for your additional room or for storage. It is an easy commute to major highways, shopping and restaurants. You will enjoy the spacious living

Anita S. Cristiano HomeSmart Homes & Estates

60 Evan Rd, Warwick, NY 10990
$320,000 Sold Feb 13, 2026

2812 Whispering Hills Unit 577, Chester, NY 10918
- 2 Beds
- 1 Bath
- 1,084 Sq Ft
- Built 1984
Last Sold Summary
- 10% Above List Price
- $295/SF
- 22 Days On Market
Current Estimated Value $310,344

Last Listing Agent Kathy White Exit Realty Connections

2812 Whispering Hills Unit 577, Chester, NY 10918

/3
Not Listed For Sale

L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817
L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817

Last Sold Summary
- 16 Days On Market
- Last Sold Price $58,450
- Feb 06, 2025
Last Listing Agent John Palermo John R. Palermo

Showing Results 1 - 40, Page 1 of 18

New York Orange County Chester

Home Trends in Chester, NY

On average, homes in Chester, NY sell after 55 days on the market compared to the national average of 57 days. The median sale price for homes in Chester, NY over the last 12 months is $503,250, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$503,250

Median Single Family Sale Price

$672,000

Median Townhouse Sale Price

$337,450

Median 2 Bedroom Sale Price

$307,500

Average Price Per Sq Ft

$276

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

5.70

Median List Price

$574,900

Median Change From 1st List Price

Median Home Sale Price YoY Change

-4%

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Chester, NY Homes

Real Estate & Homes

Home Trends in Chester, NY

Housing Trends