Homes with Parking for Sale in Chester, NY

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ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
UNLOCK UNLIMITED POTENTIAL IN WARWICK VALLEY SCHOOLS! Are you ready to stop renting, build instant equity, and design your dream home from the ground up? This hidden gem off Gibson Hill Road is your golden ticket into one of Orange County’s most desirable school districts at a rare and unbeatable entry-level price! Whether you are a savvy investor looking for your next high-margin flip, a contractor seeking a prime project, or a first-time homebuyer eager to earn serious sweat equity, the upside potential here is off the charts! Nestled in a peaceful setting with a shared private access setup off well-maintained Speranza Ct, you get the perfect balance of serene rural living with ea

$374,900

3 beds1.5 baths1,644 sq ft

260 Gibson Hill Rd, Chester, NY 10918

Private access • Countryside retreat • Peaceful setting

Listing by Keller Williams Realty

NEW 11 HRS AGO

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
69 Cedar Pond Lane, an Chester estate capturing mountain views. Offering great living, proven Airbnb/rental potential, and extensive recent upgrades, this expansive home spans 3 fully finished levels. The sun-drenched main level features soaring skylights, picture windows, an open living/dining area with wood-burning fireplace, and a chefâ€™s kitchen with new countertops, custom backsplash, breakfast bar, dining nook, wine rack, new refrigerator, and beverage fridge. Two bedrooms and 2.5 baths complete the level, plus walkout access to a large patio with outdoor bar, fireplace, and lounge area. Upstairs, the luxurious primary suite boasts mountain views, walk-in closet, and

$1,685,000

6 beds7.5 baths— sq ft

69 Cedar Pond Ln, Chester, NY 10918

Recent upgrades • Chef kitchen • Mountain views

Listing by Prominent Properties Sotheby's International Realty-Alpine, (201) 768-9300

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
WHISPERING HILLS! PRIME LOCATION! Largest Unit! Two Story Living! End Unit! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen! Dining/ Living Room with Fireplace! Master Bedroom Suite with Walk In Closet! Central Air! Country Club Living! Clubhouses! Pools! Tennis! Basketball! Tot Lot! Dog Walk! Perfect Commuter Location! Close to Major Highways, Buses & Shopping! Walk to NYC Bus!

$374,900

3 beds2.5 baths1,331 sq ft

2921 Whispering Hls, Chester, NY 10918

End unit • Eat in kitchen • Largest unit

Listing by ARC Realty 1 in Sales

FLOOR PLAN

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
Welcome to this charming ranch style home set on 4 picturesque acres, featuring beautiful flowing hardwood floors and a peaceful, private setting. The inviting kitchen offers gorgeous marble countertops, an abundance of cabinetry, a sink positioned beneath the windows, and stainless-steel appliances. From the living room, double sliding doors open onto the expansive wraparound porch, creating an effortless connection to the serene backyard perfect for relaxing, entertaining, or enjoying the surrounding nature. The spacious primary suite features a huge closet and a private master bath. Two additional bedrooms offer generous closet space, providing plenty of room for family, guests, or a hom

$550,000

3 beds2 baths1,583 sq ft

50 Hambletonian Ave, Chester, NY 10918

Marble countertops • Enlarged backyard • Private master bath

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
Welcome to Whispering Hills! This spacious two-level, 2-bedroom, 1.5-bath condo with a 1-car garage features a great combination of updates and an ideal commuter location. Step inside to a freshly painted interior featuring an updated kitchen and bathrooms. The inviting living room features a fireplace and sliders leading to a private patio, perfect for relaxing and enjoying the outdoors. Additional updates include a newer furnace, central air conditioning and water heater! Enjoy country club-style living with fantastic community amenities including clubhouses, swimming pools, tennis courts, basketball courts, playgrounds, walking areas and a dog run. An excellent commuter location with NYC

$290,000

2 beds1.5 baths1,053 sq ft

1005 Whispering Hls, Chester, NY 10918

Newer furnace • Community amenities • Private patio

Listing by Century 21 Full Service Realty

Property at 38 Shore Dr, Blooming Grove, NY 10914, 3 beds, 3 baths

$949,000

3 beds3 baths3,591 sq ft

38 Shore Dr, Blooming Grove, NY 10914

Listing by KW Hudson Valley United

Property at 121 Conklingtown Rd, Chester, NY 10918, 4 beds, 2.5 baths

$749,000

4 beds2.5 baths2,599 sq ft

121 Conklingtown Rd, Chester, NY 10918

Listing by MS Realty Group USA, Inc

Property at 2124 Whispering Hls, Chester, NY 10918, 2 beds, 1 bath

$299,000

2 beds1 bath1,084 sq ft

2124 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 32 Surrey Rd, Chester, NY 10918, 4 beds, 1.5 baths

$475,000

4 beds1.5 baths1,820 sq ft

32 Surrey Rd, Chester, NY 10918

Listing by eXp Realty

Property at 1 Sanford Ave, Chester, NY 10918, 4 beds, 3 baths

$750,000

4 beds3 baths2,280 sq ft

1 Sanford Ave, Chester, NY 10918

Listing by Redfin Real Estate

Property at 20 Mountainside Dr, Chester, NY 10918, 4 beds, 3 baths

$749,900

4 beds3 baths3,080 sq ft

20 Mountainside Dr, Chester, NY 10918

Listing by eXp Realty

Property at 13 Bianca Blvd, Chester, NY 10918, 4 beds, 2.5 baths

$700,000

4 beds2.5 baths3,296 sq ft

13 Bianca Blvd, Chester, NY 10918

Listing by Keller Williams Realty

Property at 173 Creamery Pond Rd, Chester, NY 10918, 3 beds, 2.5 baths

$699,000

3 beds2.5 baths2,533 sq ft

173 Creamery Pond Rd, Chester, NY 10918

Listing by Keller Williams Realty

Property at 176 Beverly Rd, Chester, NY 10918, 4 beds, 2.5 baths

$699,900

4 beds2.5 baths2,715 sq ft

176 Beverly Rd, Chester, NY 10918

Listing by Owner Entry.com

Property at 1 Bell Way, Chester, NY 10918, 3 beds, 2 baths

$565,000

3 beds2 baths1,724 sq ft

1 Bell Way, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 63 Hubshop Rd, Chester, NY 10918, 4 beds, 2.5 baths

$459,000

4 beds2.5 baths2,060 sq ft

63 Hubshop Rd, Chester, NY 10918

Listing by Keller Williams Realty

Property at 21 Trotting Dr, Chester, NY 10918, 3 beds, 2 baths

$475,000

3 beds2 baths1,624 sq ft

21 Trotting Dr, Chester, NY 10918

Listing by Keller Williams Realty

Property at 34 Boville Ct, Chester, NY 10918, 4 beds, 3 baths

$839,000

4 beds3 baths2,707 sq ft

34 Boville Ct, Chester, NY 10918

Listing by Keller Williams Valley Realty

Property at 3409 Whispering Hls, Chester, NY 10918, 3 beds, 2.5 baths

$360,000

3 beds2.5 baths1,331 sq ft

3409 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 66 Whitetail Run, Chester, NY 10918, 3 beds, 1.5 baths

$449,000

3 beds1.5 baths1,500 sq ft

66 Whitetail Run, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 2522 Whispering Hls, Chester, NY 10918, 3 beds, 2.5 baths

$369,000

3 beds2.5 baths1,331 sq ft

2522 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 3 Garnett Hill Rd, Chester, NY 10918, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths2,516 sq ft

3 Garnett Hill Rd, Chester, NY 10918

Listing by Keller Williams Realty

Property at 412 Laroe Rd, Chester, NY 10918, 3 beds, 2 baths

$615,000

3 beds2 baths1,848 sq ft

412 Laroe Rd, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 4 Debbie Ct, Chester, NY 10918, 5 beds, 5.5 baths

$785,000

5 beds5.5 baths5,403 sq ft

4 Debbie Ct, Chester, NY 10918

Listing by Flag Realty Group

Property at 4008 Whispering Hills Dr, Chester, NY 10918, 2 beds, 1.5 baths

$290,000

2 beds1.5 baths1,072 sq ft

4008 Whispering Hills Dr, Chester, NY 10918

Listing by Howard Hanna Rand Realty

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

$370,000

3 beds1 bath1,561 sq ft

33 Meadow Ave, Chester, NY 10918

Listing by River Realty Services, Inc.

Property at 11 Old Dominion Rd, Blooming Grove, NY 10914, 4 beds, 2.5 baths

$724,000

4 beds2.5 baths2,547 sq ft

11 Old Dominion Rd, Blooming Grove, NY 10914

Listing by Mount Realty

Property at 11 Chandler Dr, Chester, NY 10918, 3 beds, 2.5 baths

$545,000

3 beds2.5 baths1,908 sq ft

11 Chandler Dr, Chester, NY 10918

Listing by Coldwell Banker Realty

Property at 424 Laroe Rd, Chester, NY 10918, 4 beds, 3 baths

$634,999

4 beds3 baths2,316 sq ft

424 Laroe Rd, Chester, NY 10918

Listing by Epique Realty

Property at 19 Grand View Ter, Chester, NY 10918, 5 beds, 4 baths

$789,900

5 beds4 baths4,697 sq ft

19 Grand View Ter, Chester, NY 10918

Listing by eXp Realty

Property at 44 Sayer Rd, Blooming Grove, NY 10914, 3 beds, 1.5 baths

$540,000

3 beds1.5 baths2,332 sq ft

44 Sayer Rd, Blooming Grove, NY 10914

Listing by Sage Realty Center LLC

Property at 7 Lakeview Dr, Chester, NY 10918, 4 beds, 2.5 baths

$549,999

4 beds2.5 baths2,098 sq ft

7 Lakeview Dr, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 985 Craigville Rd, Chester, NY 10918, 4 beds, 3.5 baths

$750,000

4 beds3.5 baths3,100 sq ft

985 Craigville Rd, Chester, NY 10918

Listing by Serhant LLC

Property at 197 Oxford Rd, Chester, NY 10918, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths3,070 sq ft

197 Oxford Rd, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 68 Conklingtown Rd Unit 1&2, Chester, NY 10918, 6 beds, 2 baths

$575,000

6 beds2 baths— sq ft

68 Conklingtown Rd Unit 1&2, Chester, NY 10918

Listing by MS Realty Group USA, Inc

Property at 2113 Whispering Hls, Chester, NY 10918, 2 beds, 1 bath

$275,000

2 beds1 bath1,084 sq ft

2113 Whispering Hls, Chester, NY 10918

Listing by Keller Williams Realty

Property at 29 Murray Dr, Chester, NY 10918, 3 beds, 3 baths

$650,000

3 beds3 baths2,520 sq ft

29 Murray Dr, Chester, NY 10918

Listing by eXp Realty

Property at 24 Walnut St, Chester, NY 10918, 4 beds, 2.5 baths

$539,000

4 beds2.5 baths2,698 sq ft

24 Walnut St, Chester, NY 10918

Listing by Keller Williams Village Sq Rlt

Property at 94 Booth Rd, Chester, NY 10918, 3 beds, 2.5 baths

$520,000

3 beds2.5 baths2,083 sq ft

94 Booth Rd, Chester, NY 10918

Listing by Compass Greater NY, LLC

Property at 2119 Whispering Hls, Chester, NY 10918, 2 beds, 1.5 baths

$295,000

2 beds1.5 baths1,086 sq ft

2119 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 58 Nancy Ln, Chester, NY 10918, 3 beds, 2.5 baths

$749,999

3 beds2.5 baths2,718 sq ft

58 Nancy Ln, Chester, NY 10918

Listing by Howard Hanna Rand Realty

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Based on information submitted to the MLS GRID as of Mon Aug 31 2026. 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 60 homes with parking homes for sale in Chester at a median listing price of $370K. 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 31 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 were also 12 condos, 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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