Homes with Basements for Sale in Chester, NY

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ABOUT THIS HOME
Home with Basement for sale in Chester, NY:
This colonial home is truly designed for both family living and entertaining. Upon entering, a two-story entry provides easy access to all areas without needing to pass through other rooms unnecessarily. The spacious kitchen is a highlight, featuring oak cabinets, a pantry, updated appliances and a tiled backsplash and floor. For more casual gatherings, the family room offers hardwood floors. For more formal entertaining, the living room and dining room provide excellent spaces for hosting guests. The primary bedroom is a luxurious retreat, boasting a whirlpool tub, a separate shower and a walk-in closet. The additional bedrooms are all well-lit and offer ample space. The laundry is conveni

$650,000

5 beds3.5 baths2,550 sq ft

3 Derose Ln, Chester, NY 10918

Large deck • Two story entry • Spacious kitchen

Listing by Howard Hanna Rand Realty

OPEN TODAY, 12PM TO 2PM

ABOUT THIS HOME
Home with Basement for sale in Chester, NY:
Welcome to Country Woods, one of Chester’s most sought-after neighborhoods. This handsome Colonial sits on 1.7 landscaped acres and offers over 3,100 square feet of comfortable living space. A wrap-around front porch invites you inside, where a two-story foyer and 9-foot ceilings create a bright and spacious feel. The formal living and dining rooms flow seamlessly into the kitchen, complete with Corian counters and everything you need to prepare your favorite meals. The casual dining area opens to a warm and inviting family room featuring a vaulted ceiling, fireplace, and a wall of windows framing peaceful views — the perfect spot to gather for movie or game night as you watch t

$749,900

5 beds2.5 baths3,124 sq ft

9 Country Woods Dr, Chester, NY 10918

Corian counters • Vaulted ceiling • Wall of windows

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Home with Basement for sale in Chester, NY:
* * Welcome to 11 Saddle Hill Road – A Perfect Blend of Luxury, Space & Location * * This stunning brick Colonial offers the perfect balance of private luxury and everyday convenience. With over * * 5,000 square feet * * of impeccably finished living space, this home provides ample room for everyone to * * live, work, and relax in comfort * * . Step into the * * grand two-story foyer * * , flooded with natural light and featuring * * gleaming hardwood floors * * that flow throughout the home. The main level boasts a * * formal dining room * * , a versatile * * home office or flex space * * with elegant French doors, and a spacious, updated * * family ro

$845,000

4 beds4 baths4,489 sq ft

11 Saddle Hill Rd, Chester, NY 10918

Formal dining room • Eat in kitchen • Updated family room

Listing by Keller Williams Realty

ABOUT THIS HOME
Home with Basement for sale in Chester, NY:
Split-level spacious home in desirable Chester neighborhood within Warwick Valley School District! This home features newer vinyl siding, a custom front entry door, hardwood floors, ceiling fans, and radiant electric ceiling heat. The 2-car garage includes windows and an automatic opener. Enjoy the fully fenced-in yard with an in-ground pool, deck with gazebo, shed, and play set—all included. Spacious layout with attic crawl space for additional storage. Propane hot water tank installed in 2021. Home is being sold AS -IS . Freezer not included. Just a few minutes away to Legoland and desirable Sugarloaf historic area. Lots of breweries and hiking trails nearby as well. 10 minutes to l

$539,000

4 beds2.5 baths1,848 sq ft

11 Lakeview Dr, Chester, NY 10918

Fully fenced-in yard • Ceiling fans • Vinyl siding

Listing by IBNA Real Estate Group

ABOUT THIS HOME
Home with Basement for sale in Chester, NY:
Spectacular 4 bedrooms, 2.5 bathrooms colonial in the very desirable Sugarloaf Heights. This magnificent home offers heavenly views right from your rear deck. You never have to leave home when you can step outside and enjoy your own personal refuge with a fully fenced-in yard that brings privacy to your in-ground pool and hot tub. Home offers many recent upgrades which include updated kitchen, recess lighting, newer carpeting in partially finished basement. Exterior improvements include newer siding and window frames (2023), in addition to several windows being replace. Sprinkler system throughout and under ground gutter system. Home is in the Warwick School District. Short drive to shops,

$689,900

4 beds2.5 baths3,092 sq ft

2 Dawn Ct, Chester, NY 10918

8,037 sq ft lot • 2 garage spots • Pool

Listing by Keller Williams Hudson Valley

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 47 Greycourt Ave, Chester, NY 10918, 4 beds, 1.5 baths

$425,000

4 beds1.5 baths1,386 sq ft

47 Greycourt Ave, Chester, NY 10918

Listing by Curasi Realty, 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 39 Shore Dr, Blooming Grove, NY 10914, 2 beds, 2.5 baths

$469,900

2 beds2.5 baths2,282 sq ft

39 Shore Dr, Blooming Grove, NY 10914

Listing by Windsor Realty Services Inc

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

$440,000

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

$774,000

4 beds2.5 baths3,112 sq ft

15 Old Dominion Rd, Blooming Grove, NY 10914

Listing by Blooming Realty

Property at 70 Main St, Chester, NY 10918, 4 beds, 2.5 baths

$475,000

4 beds2.5 baths1,357 sq ft

70 Main St, Chester, NY 10918

Listing by Keller Williams Hudson Valley

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

$723,000

4 beds2.5 baths3,977 sq ft

278 Gibson Hill Rd, Chester, NY 10918

Listing by Keller Williams Realty

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 2 Pine Hill Rd, Chester, NY 10918, 3 beds, 2.5 baths

$915,000

3 beds2.5 baths2,302 sq ft

2 Pine Hill Rd, Chester, NY 10918

Listing by SHAHAR Management LLC

Property at 49 Stone Mountain Trl, Chester, NY 10918, 4 beds, 2.5 baths

$850,000

4 beds2.5 baths3,656 sq ft

49 Stone Mountain Trl, Chester, NY 10918

Listing by Keller Williams Hudson Valley

Property at 16 Lori Ln, Chester, NY 10918, 4 beds, 4 baths

$1,160,000

4 beds4 baths4,624 sq ft

16 Lori Ln, Chester, NY 10918

Listing by eXp Realty

Property at 37-39 Main St, Chester, NY 10918, 4 beds, 4 baths

$1,498,888

4 beds4 baths7,308 sq ft

37-39 Main St, 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 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 206 Greycourt Rd #190, Chester, NY 10918

$1,500,000

0 beds— baths— sq ft

206 Greycourt Rd #190, Chester, NY 10918

Listing by eXp Realty

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Based on information submitted to the MLS GRID as of Sun Oct 26 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 Basements for Sale in Chester

There are currently 24 homes with basements for sale in Chester at a median listing price of $440K. 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 30 days and receive 4 offers. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 1 home has 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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