Homes with Parking for Sale in Chester, NY

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ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
Stunning Chester Home with Pool, Pond & Private Backyard Oasis! Discover your own private retreat in this meticulously maintained 3-bedroom, 2.5-bath home in Chester. Perfectly positioned for privacy on a scenic lot featuring its own backyard pond, this property offers a rare combination of comfort and outdoor amenities. Step inside to a bright and airy main level where hardwood floors connect the spacious living room and dining area. This home has an ideal layout for gatherings. The living room features a cozy fireplace, adding warmth and ambiance to the space. The kitchen is ready for the home chef, boasting stainless steel appliances, ample cabinetry, and a convenient breakfast bar

$499,900

3 beds2.5 baths1,934 sq ft

6 Vista Dr, Chester, NY 10918

1.1 acre lot • 2 garage spots • Pool

Listing by Keller Williams Realty

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
B"H Grab this opportunity!!! Cozy Home in great condition sitting on a 3.2 ACER Property!!! Enjoy the above ground pool !!! Wonderful neighborhood and calm area. Open living room with wood burning fireplace, The kitchen offers a breakfast bar, Center island, Stainless steel appliances, Multiple counter space and cabinets. Finished lower level with a Den/office, Family room and full bathroom. Full unfinished attic with lots of storage space. Sq. Ft. is approximate

$699,000

3 beds3 baths3,000 sq ft

360 Prospect Rd, Chester, NY 10918

Above ground pool • Breakfast bar • Center island

Listing by eRealty Advisors, Inc

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
DISCOVER THE EPITOME OF LUXURY LIVING! With 5400 sq ft of breathtaking property, where every corner is designed for both elegance and practicality!! With expansive living areas, high-end finishes, and modern amenities, this home is perfect for entertaining or enjoying quiet moments. Embrace a lifestyle of comfort and sophistication in a space that truly feels like a retreat all year round!! Featuring a main house of 3800 sq. ft. with 4 bedrooms and 3.5 baths, complemented by a beautifully finished basement that adds three additional rooms and another bath. The open kitchen boasts elegant granite countertops, while two sunrooms and spacious living areas provide ample space for relaxation and

$849,000

5 beds5.5 baths5,403 sq ft

4 Debbie Ct, Chester, NY 10918

5.4 acre lot • 2 garage spots • Built 1982

Listing by Flag Realty Group

3D WALKTHROUGH

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with original wooden and stone mantles, 10' ceilings, and large sun-filled windows throughout. The main level offers two gracious living rooms, a formal dining room, a dedicated office, and an updated kitchen outfitted with a Wolf range, cherry cabinetry, generous storage, and a walk-in pantry. A dedicated fi

$1,395,000

4 beds2.5 baths3,866 sq ft

2948 State Route 94, Chester, NY 10918

Hand carved banister • Five fireplaces • Updated kitchen

Listing by Tuxedo Hudson Realty Corp

OPEN JAN 11, 12PM TO 2PM

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
Discover modern living at its best in this beautifully designed 2,870 sq ft contemporary home with flexible floor plan and wonderful tranquility! Set on 4.1 private acres and featuring its own pond and seasonal babbling brook, 16 Oxford Springs Road is perfect for those seeking a full-time residence or Hudson Valley getaway. This home offers retreat-like privacy yet is only minutes to all amenities and approx 60 miles to NYC. Inside, oak hardwood floors flow across both levels, setting a warm yet sophisticated tone. The main level boasts a bright eat-in kitchen, sunken living room with fireplace and sliders to the expansive backyard, a recently updated full bathroom, and 4 living spaces tha

$750,000

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

Property at 3120 Whispering Hls, Chester, NY 10918, 2 beds, 1.5 baths

$310,000

2 beds1.5 baths1,072 sq ft

3120 Whispering Hls, Chester, NY 10918

Listing by John J Lease REALTORS Inc

Property at 1503 Whispering Hls, Chester, NY 10918, 3 beds, 2.5 baths

$309,900

3 beds2.5 baths1,331 sq ft

1503 Whispering Hls, Chester, NY 10918

Listing by Century 21 E & M Williams Rlty

Property at 3917 Whispering Hls, Chester, NY 10918, 2 beds, 1.5 baths

$319,000

2 beds1.5 baths1,072 sq ft

3917 Whispering Hls, Chester, NY 10918

Listing by Keller Williams Hudson Valley

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

$1,050,000

5 beds3 baths5,080 sq ft

4 Camelback Rd, Chester, NY 10918

Listing by Prominent Properties Sotheby's

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

$725,000

5 beds2.5 baths3,124 sq ft

9 Country Woods Dr, Chester, NY 10918

Listing by Howard Hanna Rand Realty

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

$509,999

3 beds2 baths1,800 sq ft

391 Bull Mill Rd, Chester, NY 10918

Listing by Century 21 Realty Center

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

$1,875,000

6 beds7.5 baths7,034 sq ft

69 Cedar Pond Ln, Chester, NY 10918

Listing by Four Seasons Sothebys Intl

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

$734,000

4 beds2.5 baths3,112 sq ft

15 Old Dominion Rd, Blooming Grove, NY 10914

Listing by Blooming Realty

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 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 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

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NEW 23 HRS AGO

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
The Wait Is Over!!! Hidden Creek of Monroe has an end unit for sale right now! You will be impressed with the privacy, space and upgrades that this home has. With yard space on the side and a backyard with mountain views you're going to fall in love. This open layout gives way for you to decorate any way you want with whatever size furniture you have and the end units were built with additional windows which allow for more natural light. Inside you'll see the hardwood floors flow throughout the main floor living area and up to the second level. Do you like to entertain? The formal dining area can accommodate all of your dinner guests. The kitchen flows from one end to the other so you are

$489,000

2 beds3 baths1,777 sq ft

10 Silas Seaman St, Monroe, NY 10950

Custom cabinets • Open layout • Formal dining area

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
Brand New Construction in Hamptonburgh – Private 2.6 Acres & Minutes to Metro North! Why choose between privacy and a convenient commute when you can have both? Welcome to this stunning, brand-new construction raised ranch located in the sought-after Town of Hamptonburgh and Washingtonville School District. Tucked away down a long, private driveway on an expansive 2.6-acre lot, this home is your own secluded retreat that keeps you connected to everything. Ideally situated for commuters, you are just 10 minutes from two Metro North train stations and minutes from NY Stewart International Airport. Enjoy easy access to local shopping and dining without sacrificing the peace of coun

$649,900

3 beds2 baths1,560 sq ft

3368 State Route 208, Campbell Hall, NY 10916

2.6 acre lot • 2 garage spots • Built 2025

Listing by Keller Williams Hudson Valley

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
15 Duelk Ave, Monroe, NY — Enjoy a refreshing lifestyle with your own swimming pool at this charming single-family home. Offering 4 bedrooms and 1.5 bathrooms, this property features a finished basement, an attached garage, and a spacious yard perfect for gatherings and relaxation. Nestled in a quiet residential neighborhood and conveniently close to schools, shopping, and local amenities—this is a wonderful opportunity to own a comfortable home in Monroe.

$999,999

6 beds3 baths2,350 sq ft

15 Duelk Ave, Monroe, NY 10950

Spacious yard • Close to schools • Swimming pool

Listing by eRealty Advisors, Inc

3D WALKTHROUGH

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
One-floor living at its finest! This beautifully renovated 3-bedroom, 1-bath home has been completely updated inside and out and is truly move-in ready. The home is filled with abundant natural light, creating a warm and inviting atmosphere throughout. Exterior improvements include a brand-new roof, new vinyl siding, and new windows. Inside, you’ll find a stunning high-end kitchen featuring all-new stainless-steel appliances, including a dishwasher, along with a stylishly updated full bathroom. Behind the scenes, enjoy peace of mind with all-new electrical, plumbing, and insulation. Ideally located close to major highways for easy commuting, and just minutes from golf courses, farms,

$425,000

3 beds1 bath1,312 sq ft

60 W Jeanibo Rd, Monroe, NY 10950

One-floor living • Renovated bungalow • New vinyl siding

Listing by Keller Williams Realty

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
Welcome to your private retreat in the heart of Monroe! Tucked into a serene neighborhood, this charming 4 bedroom, 2.5 bath offers the perfect blend of indoor comfort and outdoor enjoyment. Set on a beautifully landscaped lot, the home greets you with a long driveway leading to the attached 2 car garage. Enter to find a bright and inviting home with hardwood floors, recessed lighting and a cozy fireplaces. The formal dining room leads into the sun filled kitchen with an open concept that flows into the spacious breakfast nook. You'll find four generously sized bedrooms, including a primary suite with an en-suite bath. Central air conditioning ensures year-round comfort. Enjoy summers by th

$1,095,000

4 beds2.5 baths2,311 sq ft

11 Cliff Ct, Monroe, NY 10950

Attached garage • Long driveway • Recessed lighting

Listing by Keller Williams Realty

COMING SOON

ABOUT THIS HOME
Home with Parking for sale in Chester, NY:
* * * COMING SOON! Showings start Sunday, January 11th. Schedule your appointment today! * * * This fixer-upper home is ready for a makeover transformation! Exceptional opportunity for a full renovation in a prime location. Situated in the sought-after Village of Monroe with municipal services. This 1,792sqft Raised Ranch home features 4 bedrooms, 1.5 baths, and a 1-car garage, offering a solid footprint for your custom restoration. Situated on a level . 42-acre lot with a fenced backyard and deck, the property offers generous outdoor space and so much equity potential. Conveniently located near Route 17, I-87, Metro-North Harriman Station, NYC Bus Park & Ride, and Woodbury Com

$349,000

4 beds1.5 baths1,792 sq ft

534 High St, Monroe, NY 10950

0.42 acre lot • Garage • Built 1974

Listing by Howard Hanna Rand Realty

Property at 36 Ironworks Rd, Monroe, NY 10950, 4 beds, 2.5 baths

$590,000

4 beds2.5 baths2,229 sq ft

36 Ironworks Rd, Monroe, NY 10950

Listing by MK Realty Inc

Property at 4 Duelk Ave, Monroe, NY 10950, 3 beds, 1.5 baths

$750,000

3 beds1.5 baths2,204 sq ft

4 Duelk Ave, Monroe, NY 10950

Listing by MS Realty Group USA, Inc

Property at 4430 State Route 94, Florida, NY 10921, 3 beds, 2 baths

$650,000

3 beds2 baths2,049 sq ft

4430 State Route 94, Florida, NY 10921

Listing by Exit Realty Venture

Property at 133 W Mombasha Rd, Monroe, NY 10950, 5 beds, 3 baths

$1,295,000

5 beds3 baths3,667 sq ft

133 W Mombasha Rd, Monroe, NY 10950

Listing by eXp Realty

Property at 75 Duelk Ave, Monroe, NY 10950, 4 beds, 2 baths

$749,000

4 beds2 baths2,370 sq ft

75 Duelk Ave, Monroe, NY 10950

Listing by Blooming Realty

Property at 14 Harness Rd, Goshen, NY 10924, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths2,572 sq ft

14 Harness Rd, Goshen, NY 10924

Listing by Howard Hanna Rand Realty

Property at 13 Newbury St, Monroe, NY 10950, 3 beds, 2 baths

$675,000

3 beds2 baths1,584 sq ft

13 Newbury St, Monroe, NY 10950

Listing by Blooming Realty

Property at 1 Jessica Ct, Goshen, NY 10924, 4 beds, 2.5 baths

$725,000

4 beds2.5 baths3,627 sq ft

1 Jessica Ct, Goshen, NY 10924

Listing by Keller Williams Realty Partner

Property at 5 Fox Hollow Dr, Blooming Grove, NY 10914, 4 beds, 3.5 baths

$699,000

4 beds3.5 baths3,968 sq ft

5 Fox Hollow Dr, Blooming Grove, NY 10914

Listing by Century 21 Realty Center

Property at 9 Merriewold Ln S, Monroe, NY 10950, 3 beds, 2 baths

$769,000

3 beds2 baths1,794 sq ft

9 Merriewold Ln S, Monroe, NY 10950

Listing by Realty Blue Corp

Property at 71 Walton Ter, Monroe, NY 10950, 4 beds, 2.5 baths

$550,000

4 beds2.5 baths2,640 sq ft

71 Walton Ter, Monroe, NY 10950

Listing by Howard Hanna Rand Realty

Property at 33 Dallas Dr, Monroe, NY 10950, 4 beds, 1.5 baths

$895,000

4 beds1.5 baths1,732 sq ft

33 Dallas Dr, Monroe, NY 10950

Listing by Howard Hanna Rand Realty

Property at 72 Peddler Hill Rd, Monroe, NY 10950, 5 beds, 3 baths

$2,000,000

5 beds3 baths3,172 sq ft

72 Peddler Hill Rd, Monroe, NY 10950

Listing by Blooming Realty

Property at 7 O'sullivan Ln, Monroe, NY 10950, 4 beds, 2.5 baths

$675,000

4 beds2.5 baths2,338 sq ft

7 O'sullivan Ln, Monroe, NY 10950

Listing by Howard Hanna Rand Realty

Based on information submitted to the MLS GRID as of Sat Jan 03 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 20 homes with parking homes for sale in Chester at a median listing price of $397K. 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 17 days and receive 4 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 3 homes have been sold in Chester. In addition to houses in Chester, there were also 5 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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