Homes with Parking for Sale in Chester, NY

27 homes

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ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
Discover modern living at its finest in this beautifully designed 2,870 sq ft contemporary home set on 4.1 stunning acres featuring a peaceful pond and a seasonal babbling brook. Offering wonderful privacy and an effortless indoor–outdoor lifestyle, this property is a rare retreat surrounded by nature. Inside, oak hardwood floors flow across both levels, setting a warm yet sophisticated tone. The lower level welcomes you with a sleek entry area leading into multiple stylish living spaces, including a formal living room and a sunken living room with fireplace and sliders that open directly to the expansive backyard. The bright eat-in kitchen features newer stainless steel appliances (d

$779,000

3 beds3 baths2,870 sq ft

16 Oxford Springs Rd, Chester, NY 10918

4.1 acre lot • 2 garage spots • Built 1988

Listing by RE/MAX Benchmark Realty Group

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
Motivated sellers. Welcome to Whispering Hills, one of the most sought-after communities in the area with resort style amenities and unbeatable commuter convenience. Picture yourself coming home to this beautiful space. The large living room opens to sliding glass doors that lead out to your private deck, the perfect spot to unwind after a long day. Cathedral ceilings create an open, airy feel, and the fireplace adds cozy charm on cool nights while you enjoy a cup of hot chocolate or a glass of wine. The kitchen has been thoughtfully updated with stainless steel appliances, a five-burner chef’s gas stove, granite countertops, subway tile, and a spacious pantry. The dining area feels p

$290,000

2 beds1 bath1,084 sq ft

2812 Whispering Hls, Chester, NY 10918

$420 HOA • Garage • Community pool

Listing by Exit Realty Connections

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
WHISPERING HILLS!! SOLD AS IS!!! Largest Model! Two Level Living! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen! Living Room! Master Bedroom Suite with Walk in Closet! Patio! Country Club Living! Clubhouses! Pools! Tennis! Basket Ball! Tot Lot! Dog Walk! Perfect Commuter Location! Walk to NY Bus! Close to Major Highway & Shopping!

$299,900

3 beds2.5 baths1,331 sq ft

2104 Whispering Hls, Chester, NY 10918

Eat in kitchen • Master bedroom suite • Walk in closet

Listing by ARC Realty 1 in Sales

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
Nice end unit 3 bedroom 2.5 bath condo with 2 car garage in whispering hills. Primary bedroom with private full bath and 2 nice size extra bedrooms plus a hall bath on the 2nd floor. Warm up on those cold nights with the fireplace in the living room. Enjoy a quiet moment on your private patio sipping your coffee. Great location with playground and tennis across the street, pool, clubhouse and bus stop just 1 block over. Convenient to Route 17, and the NYS Thruway for commuters. Legoland is just 10 minutes away! Convenient shopping, and restaurants nearby. Quaint downtown Sugarloaf shopping area, The Castle Fun Center and local theatre is within a few minutes drive.

$339,900

3 beds2.5 baths1,331 sq ft

1503 Whispering Hls, Chester, NY 10918

Clubhouse • Private patio • Pool

Listing by Century 21 E & M Williams Rlty

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
This is a "Neat as a pin" ranch in the Village of Chester. The kitchen has many updated appliances and a custom pantry with large pull-out drawers. The Living room wood floors were refinished and are immaculate. The bathroom has been updated and built to be ADA-compliant with a space-saving "pocket door. " There is a large shed in the backyard, all near all the activities the Village has to offer.

$369,900

2 beds1 bath1,084 sq ft

18 Oakland Ave, Chester, NY 10918

0.36 acre lot • Garage • Built 1955

Listing by Keller Williams Realty

Property at 4 Camelback Rd, Chester, NY 10918, 5 beds, 3 baths

$1,098,888

5 beds3 baths5,080 sq ft

4 Camelback Rd, Chester, NY 10918

Listing by Prominent Properties Sotheby's

Property at 1401 Whispering Hls, Chester, NY 10918, 2 beds, 1 bath

$295,000

2 beds1 bath1,084 sq ft

1401 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 9 Country Woods Dr, Chester, NY 10918, 5 beds, 2.5 baths

$739,900

5 beds2.5 baths3,124 sq ft

9 Country Woods Dr, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 80 Pewter Cir, Chester, NY 10918, 3 beds, 2.5 baths

$534,900

3 beds2.5 baths1,946 sq ft

80 Pewter Cir, Chester, NY 10918

Listing by BHG Real Estate Green Team

Property at 7 Park Pl, Chester, NY 10918, 4 beds, 3.5 baths

$740,000

4 beds3.5 baths2,780 sq ft

7 Park Pl, Chester, NY 10918

Listing by Century 21 Full Service Realty

Property at 10 Damian Ct, Chester, NY 10918, 11 beds, 6.5 baths

$1,375,000

11 beds6.5 baths4,327 sq ft

10 Damian Ct, Chester, NY 10918

Listing by MS Realty Group USA, Inc

Property at 16 Mari Rd, Chester, NY 10918, 4 beds, 3 baths

$500,000

4 beds3 baths2,098 sq ft

16 Mari Rd, Chester, NY 10918

Listing by Keller Williams Realty

Property at 3 Derose Ln, Chester, NY 10918, 5 beds, 3.5 baths

$650,000

5 beds3.5 baths2,550 sq ft

3 Derose Ln, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 25 High St, Chester, NY 10918, 4 beds, 2.5 baths

$515,000

4 beds2.5 baths2,898 sq ft

25 High St, Chester, NY 10918

Listing by Christie's Int. Real Estate

Property at 278 Gibson Hill Rd, Chester, NY 10918, 4 beds, 2.5 baths

$722,000

4 beds2.5 baths3,977 sq ft

278 Gibson Hill Rd, Chester, NY 10918

Listing by Keller Williams Realty

Property at 39 Shore Dr, Blooming Grove, NY 10914, 2 beds, 2.5 baths

$465,000

2 beds2.5 baths2,282 sq ft

39 Shore Dr, Blooming Grove, NY 10914

Listing by Windsor Realty Services Inc

Property at 391 Bull Mill Rd, Chester, NY 10918, 3 beds, 2 baths

$519,999

3 beds2 baths1,800 sq ft

391 Bull Mill Rd, Chester, NY 10918

Listing by Century 21 Realty Center

Property at 33 Meadow Ave, Chester, NY 10918, 3 beds, 1 bath

$430,000

3 beds1 bath1,561 sq ft

33 Meadow Ave, Chester, NY 10918

Listing by River Realty Services, Inc.

Property at 69 Cedar Pond Ln, Chester, NY 10918, 6 beds, 7.5 baths

$1,975,000

6 beds7.5 baths7,034 sq ft

69 Cedar Pond Ln, Chester, NY 10918

Listing by Four Seasons Sothebys Intl

Property at 507 Bull Mill Rd, Chester, NY 10918, 5 beds, 2.5 baths

$674,999

5 beds2.5 baths3,115 sq ft

507 Bull Mill Rd, Chester, NY 10918

Listing by Keller Williams Hudson Valley

Property at 32 Mountainside Dr, Chester, NY 10918, 4 beds, 2.5 baths

$849,900

4 beds2.5 baths2,603 sq ft

32 Mountainside Dr, Chester, NY 10918

Listing by Our House Real Estate Group

Property at 15 Old Dominion Rd, Blooming Grove, NY 10914, 4 beds, 2.5 baths

$774,000

4 beds2.5 baths3,112 sq ft

15 Old Dominion Rd, Blooming Grove, NY 10914

Listing by Blooming Realty

Property at 34 Mountainside Dr, Chester, NY 10918, 4 beds, 3 baths

$699,990

4 beds3 baths1,867 sq ft

34 Mountainside Dr, Chester, NY 10918

Listing by Our House Real Estate Group

Property at 53 Odyssey Dr, Chester, NY 10918, 4 beds, 3.5 baths

$1,100,000

4 beds3.5 baths4,467 sq ft

53 Odyssey Dr, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 20 Goshen Rd, Chester, NY 10918, 4 beds, 2.5 baths

$1,775,000

4 beds2.5 baths3,348 sq ft

20 Goshen Rd, Chester, NY 10918

Listing by eXp Realty

Property at 5 Gabriels Dr, Chester, NY 10918, 4 beds, 2.5 baths

$1,099,000

4 beds2.5 baths2,722 sq ft

5 Gabriels Dr, Chester, NY 10918

Listing by Keller Williams Realty

Property at Oxford Rd, Blooming Grove, NY 10918

$325,000

— beds— baths— sq ft

Oxford Rd, Blooming Grove, NY 10918

Listing by RE/MAX Benchmark Realty Group

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Based on information submitted to the MLS GRID as of Fri Nov 28 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes with Parking for Sale in Chester

There are currently 27 homes with parking homes for sale in Chester at a median listing price of $499K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chester stay on the market for 39 days and receive 4 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 4 homes have been sold in Chester. In addition to houses in Chester, there was also 1 condo, 1 townhouse, and 1 multi-family unit for sale in Chester last month. Find your dream home in Chester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chester. Our Chester real estate stats and trends will give you more information about home buying and selling trends in Chester. If you're looking to sell your home in the Chester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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