Chester, NY Homes for Sale with Pool

Secluded Trout Brook Estate: Expansive 5,700+ Sq Ft, 6-Car Garage, Ready for Multi-Gen Living and Entertaining. Nestled on nearly six private acres in the exclusive Trout Brook Estates, this expansive Colonial-style estate blends classic elegance with modern comfort. Built in 1993 and thoughtfully designed for multi-generational living and refined entertainment, the home offers generous space,

Carmela Lopez Borrazas Serhant LLC

Welcome to this beautifully maintained end-unit townhouse offering serene lakefront living and an exceptional array of community amenities, including a pool, playground, basketball & tennis courts. Freshly painted throughout the first floor and enhanced with elegant crown molding, this home showcases quality finishes and pride of ownership. Attractive vinyl plank flooring extends through the

Donna Gennaro Howard Hanna Rand Realty

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

Frank Golio Howard Hanna Rand Realty

Own a true piece of history with the iconic Hambletonian House, a one-of-a-kind Victorian estate built in the 19th century by William Rysdyk, original owner of Hambletonian 10—the legendary sire that shaped nearly all modern Standardbred racehorses. Perfectly positioned on nearly three private acres atop a knoll in the heart of Chester, New York, this meticulously maintained property offers a

Beth Palma Keller Williams Realty

Peaceful country living in this two-story center lakefront unit with full basement located in Windridge community. Enjoy incredible mountain views from this large private Townhome. Primary bedroom on upper level with walk in closet and large sitting area which can be used as home office. Slider to rear patio with beautiful lake views!! Large living and dining area. Beautiful quiet complex close

Margaret Galatro ARC Realty 1 in Sales

Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home.Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday

DAVID DEBERARDINIS Serhant LLC

Imagine ending everyday watching the sun set from your front porch, experiencing views that change with every season. Sunset views, fenced yard, brand new Trex deck, pool, home office and room for four sleeping spaces make this the perfect property. Perched at the top of the highly sought-after Fieldcrest subdivision, this stunning Colonial captures breathtaking panoramic views and unforgettable

Gina Dudgeon Howard Hanna Rand Realty

Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing

Rosalie Cook Weichert Realtors

Welcome home to this beautifully updated 3-bedroom, 2-bathroom condominium with a 1-car garage, perfectly situated in the highly sought-after Whispering Hills community. Offering modern upgrades, spacious living, and resort-style amenities, this home is truly move-in ready. Step inside to discover a bright, open floor plan featuring gleaming hardwood floors, an updated chef-inspired kitchen with

Kevin Grier KW Hudson Valley United

Step into this gorgeous Townhouse.Upon entering you’ll be welcomed by a perfect floor plan. The inviting living room features wooden floors, a cozy fireplace, and windows. The stylish kitchen has a functional layout and is outfitted with stainless steel appliances and granite countertops. The master-bedroom offers a modern feel and a walk in closet. Enjoy the amenity centers. Stop dreaming and

Jasmine Wadhwa Howard Hanna Rand Realty

Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that

Jake Garay Serhant LLC

Welcome to this beautifully maintained raised ranch, perfectly situated on a desirable corner lot in Chester. This inviting 3-bedroom, 2 full and 1 half bath home blends comfort, style, and modern convenience in a location you'll love. Filled with natural light, the home features spacious living areas and a well-appointed kitchen with stainless steel appliances. The finished basement offers

Daniella Restrepo Coldwell Banker Realty

Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining.Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and

Janet Rendle Weichert Realtors

Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

Elimelech Kremer MS Realty Group USA, Inc

Spacious and well-maintained 3BR/2.5BA townhouse in desirable Windridge community. Features include updated laminate hardwood flooring, fireplace, eat-in kitchen, stainless steel appliances, private balcony off primary bedroom, sliding glass doors to private patio, attached 1-car garage with storage loft, and pull-down attic access. Community amenities include pool, clubhouse, and park.

Martin Remo RE/MAX Prime Properties

Escape to your own private retreat at 49 Stone Mountain Trail. Tucked away on more than 7 acres with mountain views, this contemporary home delivers the perfect balance of comfort, space, and outdoor enjoyment. Imagine mornings filled with sunlight streaming through oversized windows, evenings gathered around the stone fireplace, and summers spent relaxing by the in-ground pool surrounded by

Arya Rabinovits eRealty Advisors, Inc

Located in the Warwick School district on a coveted street sits this larger than life home with impressive presence. The curved driveway welcomes you to the wide porch, perfect for rocking chairs and relaxing. The impressive entrance with custom stairway and window seat is just the first of impressive touches in this home. Large kitchen overlooks the yard and is well appointed with Thor

Kimberly Corkum Keller Williams Realty

Set on 3.2 acres within the Monroe-Woodbury School District, 335 Laroe Road offers a rare combination of space, functionality, and a convenient Chester location. Step inside to the welcoming two-story foyer featuring an open staircase and you'll immediately appreciate the size of the home. The main level offers a functional layout with multiple living spaces, including a living room, formal

Christina D'Altiiio Coldwell Banker Choice Prop.

From the moment you arrive, it's clear this is a home whose character and setting are best experienced firsthand. The bright, open-concept living area features vaulted ceilings and abundant natural light, creating an inviting space for everyday living and entertaining. A beautiful den with two walls of windows and a gas fireplace overlooks the pool and surrounding landscape. The thoughtfully

David White Owner Entry.com

Beautiful Colonial set on just under an acre of meticulously landscaped property, offering breathtaking sunset views from a very private backyard. The taxes may be reduced by up to 20%; however, a tax appeal cannot be filed until 2027. Great spacious front porch! On a quiet cul-de-sac, this home features a stunning in-ground pool with a new heater, cover & pump. Pool filter, and liner are about 4

Sharon Kushner eXp Realty

Welcome Home! Well maintained two bedroom unit with lake and mountain views. Spacious living room with access to a private balcony. Eat in kitchen has updated counter tops and new appliances. Both bedrooms have ample closet space. Windridge is a quiet community conveniently located minutes from town. Great commuter location. Amenities include pool, playground, tennis and basketball courts,

Valerie Quinn Keller Williams Realty