Luxury homes for sale & real estate in Chester, NY

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ABOUT THIS HOME
Luxury Home for sale in Chester, NY:
The one you don't to miss. Nestled on a serene cul-de-sac in the executive subdivision of Country Woods, this magnificent home sits on one of the most beautiful streets within the sought-after Monroe-Woodbury School District. Step into perfection as you enter the grand foyer and are immediately welcomed by a light-filled, open floor plan that exudes elegance and sophistication. This meticulously maintained home showcases exquisite craftsmanship and attention to detail throughout Custom moldings, gleaming hardwood floors, designer lighting, and stately architectural columns that evoke the feel of a Westchester or Bergen County estate. The bright and spacious formal living room flows seamless

$1,098,888

5 beds3 baths5,080 sq ft

4 Camelback Rd, Chester, NY 10918

Open floor plan • Grand foyer • Custom moldings

Listing by Prominent Properties Sotheby's

ABOUT THIS HOME
Luxury Home for sale in Chester, NY:
Listed on the National Register of Historic Places in the Sugar Loaf Historic District, this stunning Victorian is a Circa 1910 Sears Roebuck Kit Home (#118 The Clyde). Not only is this your dream home located in beautiful Sugar Loaf, NY, it is also zoned for extensive commercial use. Just a 1-minute walk to the quaint Sugar Loaf Arts & Crafts Village, cafes and Sugar Loaf Performing Arts Center. Enjoy morning coffee on the porch and head to work in your office with custom built library and pocket doors on the first level. With a whole house generator on stand-by you never have to worry about a storm leaving you without power. Purchased by an artist this home has been extensively and

$875,000

3 beds2.5 baths2,302 sq ft

2 Pine Hill Rd, Chester, NY 10918

50-year shingle roof • Custom moldings • Custom built library

Listing by SHAHAR Management LLC

ABOUT THIS HOME
Luxury Home for sale in Chester, NY:
Welcome to 10 Damian Court — a stunning custom Colonial set on 2.6 acres of beautifully landscaped grounds in a peaceful Chester cul-de-sac. Built in 2004, this impressive home offers over 4,300 sq ft of elegant living space, featuring 11 bedrooms and 6.5 baths designed for comfort and flexibility. Enjoy a spacious eat-in kitchen with granite counters and pantry, a formal dining area, and a bright family room perfect for gatherings. The primary suite includes a private bath and walk-in closet, offering a true retreat. Additional highlights include central air, a full basement, and a 3-car garage. Surrounded by nature yet conveniently close to major shopping and transit, this property

$1,375,000

11 beds6.5 baths4,327 sq ft

10 Damian Ct, Chester, NY 10918

Primary bathroom • 2 fireplaces • Peaceful cul-de-sac

Listing by MS Realty Group USA, Inc

ABOUT THIS HOME
Luxury Home for sale in Chester, NY:
Set on 10 private acres with sweeping mountain views from nearly every room, 69 Cedar Pond is a five-bedroom, eight-bath estate that exemplifies expansive design and contemporary style. The striking A-frame architecture, double-height windows, and soaring ceilings create dramatic, light-filled interiors where every angle frames the surrounding landscape and sunsets. A three-story entry sets the tone, leading into an open great room anchored by a statement fireplace. Walls of glass blur the line between indoors and out, opening to an 1,800 sq ft deck that wraps the home with extraordinary vistas and flows seamlessly to an outdoor bar, dining, and lounge area with fire pit—perfect for e

$1,975,000

6 beds7.5 baths7,034 sq ft

69 Cedar Pond Ln, Chester, NY 10918

Private acres • Soaring ceilings • Open great room

Listing by Four Seasons Sothebys Intl

ABOUT THIS HOME
Luxury Home for sale in Chester, NY:
Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a harmonious main floor, where an open-flow layout seamlessly blends with versatile spaces tailored for a home office, music room, or study. Freshly painted in a neutral palette, the living room, complete with a TV and Bose surround sound system (included), sets the stage for memorable gatherings. The ad

$1,100,000

4 beds3.5 baths4,467 sq ft

53 Odyssey Dr, Chester, NY 10918

5.5 acre lot • 2 garage spots • Pool

Listing by Howard Hanna Rand 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 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 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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ABOUT THIS HOME
Luxury Home for sale in Chester, NY:
LAND VALUE!!! This property is zoned to build two new homes on it!! Or you can enjoy the charm of the existing home. THIS LAND OFFERS BREATHTAKING SUNSET VIEWS! Description of current 'move in ready' updated home: The main level features 2 bedrooms, 1 full bath, a spacious living room, a formal dining room, and a kitchen. The lower level provides a second kitchen, a laundry room with a washer and dryer, garage access, and half bathroom. For showings, please keep the door CLOSED at all times to ensure the cat does not get out.

$959,000

3 beds1.5 baths1,680 sq ft

12 Strawberry Ln, Monroe, NY 10950

0.62 acre lot • Garage • Built 1965

Listing by eXp Realty

ABOUT THIS HOME
Luxury Home for sale in Chester, NY:
Experience the ultimate in natural beauty on this expansive lot, spanning nearly half an acre, perfectly situated within the prestigious Woodbury Junction. With its prime location, this lot offers breathtaking panoramic views, providing a stunning backdrop for your future outdoor endeavors. Build your custom dream house on this incredible property, tailored to your every need and desire. Bring your vision to life! This is a rare opportunity to create a bespoke estate!

$1,250,000

5 beds3.5 baths3,100 sq ft

23 Central Vly, Monroe, NY 10950

Expansive lot • Custom dream house • Bespoke estate

Listing by eRealty Advisors, Inc

ABOUT THIS HOME
Luxury Home for sale in Chester, NY:
Elegant colonial home situated on one of Monroe’s most desirable streets, Cul de sac & Gated backyard making it super safe and family friendly. house Features a gourmet kitchen with quartz countertops, custom maple cabinetry, a center island, and porcelain flooring. High end appliances, The open layout flows into a bright family room with a wood-burning fireplace and floor-to-ceiling windows. All bedrooms are spacious, with a primary suite offering dual walk-in closets. The backyard provides resort-style living with an stunning inground pool, waterfall, bar, and surround sound system. This property also includes lake rights, offering access to a private lake, and is convenientl

$885,000

3 beds3 baths3,000 sq ft

18 Peterson Rd, Monroe, NY 10950

Quartz countertops • Porcelain flooring • Gourmet kitchen

Listing by Rock Realty Group USA Inc

ABOUT THIS HOME
Luxury Home for sale in Chester, NY:
Welcome to 5 Sears Road, Blooming Grove, NY! * * Brand new Construction * * Ready to move in!! Discover this spacious and brand new 9-room apartment featuring an incredible amount of living space—perfect for anyone who values comfort and flexibility. This impressive residence offers 5 generous bedrooms and 4 modern bathrooms, ensuring everyone has their own space and privacy. Opportunities like this don’t come often. Don’t miss your chance to call this exceptional apartment, your home! Schedule a viewing today!

$879,000

5 beds3.5 baths3,058 sq ft

5 Sears Rd #102, Monroe, NY 10950

2 parking spots • Built 2025 • Listed 16 days

Listing by eRealty Advisors, Inc

ABOUT THIS HOME
Luxury Home for sale in Chester, NY:
Welcome to 5 Sears Road, Blooming Grove, NY! * * Brand new Construction * * Ready to move in!! Discover this spacious and brand new 9-room apartment featuring an incredible amount of living space—perfect for anyone who values comfort and flexibility. This impressive residence offers 5 generous bedrooms and 4 modern bathrooms, ensuring everyone has their own space and privacy. Opportunities like this don’t come often. Don’t miss your chance to call this exceptional apartment, your home! Schedule a viewing today!

$879,000

5 beds3.5 baths3,058 sq ft

5 Sears Rd #101, Monroe, NY 10950

2 parking spots • Built 2025 • Listed 16 days

Listing by eRealty Advisors, Inc

ABOUT THIS HOME
Luxury Home for sale in Chester, NY:
Rare opportunity to purchase this gorgeous property that consists of 3 homes nestled on 3.5 beautiful acres. The main Colonial residence has been gutted and will need to be renovated/rebuilt, however, you can live in one of the additional two residences while you renovate! The 2nd residence called the “stone cottage” has 2 fieldstone fireplaces, a full kitchen, a vaulted ceiling in the bedroom, a washer/dryer, and a full bath. The 3rd residence is called the “white cottage” and sits atop the highest point on the property. This charming cottage has 2/3 bedrooms, a large kitchen, a full bath, and a new 400 sq ft Trex deck with custom railings that is totally private t

$874,900

4 beds2 baths2,466 sq ft

651 Lakes Rd, Monroe, NY 10950

Full kitchen • Washer dryer • Vaulted ceiling

Listing by Howard Hanna Rand Realty

Property at 1280 State Route 208, Monroe, NY 10950, 4 beds, 2.5 baths

$1,100,000

4 beds2.5 baths2,541 sq ft

1280 State Route 208, Monroe, NY 10950

Listing by Howard Hanna Rand Realty

Property at 1 Stahl Way, Monroe, NY 10950, 4 beds, 3.5 baths

$919,900

4 beds3.5 baths3,028 sq ft

1 Stahl Way, Monroe, NY 10950

Listing by Weichert Realtors

Property at 23 West Meadow Way, Warwick, NY 10990, 4 beds, 2.5 baths

$920,000

4 beds2.5 baths2,969 sq ft

23 West Meadow Way, Warwick, NY 10990

Listing by BHG Real Estate Green Team

Property at 208 Oakland Ave, Monroe, NY 10950, 4 beds, 4.5 baths

$929,000

4 beds4.5 baths3,410 sq ft

208 Oakland Ave, Monroe, NY 10950

Listing by Keller Williams Realty

Property at 5 Tappan Dr, Monroe, NY 10950, 5 beds, 2 baths

$867,000

5 beds2 baths2,000 sq ft

5 Tappan Dr, Monroe, NY 10950

Listing by eRealty Advisors, Inc

Property at 34 Twin Lakes Rd, Monroe, NY 10950, 5 beds, 2.5 baths

$950,000

5 beds2.5 baths3,166 sq ft

34 Twin Lakes Rd, Monroe, NY 10950

Listing by Rieber Realty Inc

Property at 101 Upper Wisner Rd, Warwick, NY 10990, 3 beds, 3 baths

$1,800,000

3 beds3 baths1,500 sq ft

101 Upper Wisner Rd, Warwick, NY 10990

Listing by Christie's Int. Real Estate

Property at 157 Arcadia Rd, Goshen, NY 10924, 10 beds, 5.5 baths

$2,495,000

10 beds5.5 baths6,090 sq ft

157 Arcadia Rd, Goshen, NY 10924

Listing by Iron Valley RE Tri-State

Property at 10 Fountayne Ct, Washingtonville, NY 10992, 3 beds, 2.5 baths

$1,107,000

3 beds2.5 baths2,378 sq ft

10 Fountayne Ct, Washingtonville, NY 10992

Listing by Keller Williams Hudson Valley

Property at 11 Dorian Way, Campbell Hall, NY 10916, 4 beds, 3.5 baths

$1,299,000

4 beds3.5 baths3,776 sq ft

11 Dorian Way, Campbell Hall, NY 10916

Listing by Howard Hanna Rand Realty

Property at 63 Colonial Ave, Warwick, NY 10990, 6 beds, 5.5 baths

$2,000,000

6 beds5.5 baths6,254 sq ft

63 Colonial Ave, Warwick, NY 10990

Listing by Chapin Sotheby's Intl Rlty

Property at 11 Aske St, Warwick, NY 10990, 4 beds, 2.5 baths

$985,000

4 beds2.5 baths2,752 sq ft

11 Aske St, Warwick, NY 10990

Listing by ARC Realty 1 in Sales

Property at 32 Fox Hollow Dr, Blooming Grove, NY 10914, 5 beds, 3.5 baths

$900,000

5 beds3.5 baths3,500 sq ft

32 Fox Hollow Dr, Blooming Grove, NY 10914

Listing by Keller Williams Hudson Valley

Property at 11 Merriewold Ln N, Monroe, NY 10950, 5 beds, 2 baths

$869,000

5 beds2 baths1,900 sq ft

11 Merriewold Ln N, Monroe, NY 10950

Listing by eRealty Advisors, Inc

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.

Luxury Homes for Sale in Chester

There are currently 9 luxury 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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