Pleasant Valley, NY Homes for Sale with Pool

Hilltop Retreat, built in the Millenium Mansion style, provides an incomparable experience of country living. This gracious residence is approached via a meandering driveway past stone walls and a pond and is secluded within 66 acres of curated lawns w/ majestic trees, a shimmering pond, old growth forest, and year-round Catskill mountain views. Casually formal, w/over 7,000sqft of living space

Eliane Abramoff Four Seasons Sothebys Intl

Timeless Elegance Meets Modern Comfort in the Heart of the Hudson Valley. Step into a world of refined charm and historic grandeur with this magnificent estate, originally constructed in 1867 and meticulously restored to preserve its legacy. Lovingly maintained over generations, the property blends classic architectural detail with the comforts of contemporary living, offering an unparalleled

Jillian Pajer Douglas Elliman Real Estate

CONVERTED BARNS WITH POOL. This charming getaway offers fun lofty spaces to gather, entertain and enjoy the countryside, while conveniently located to the TSP and Millbrook Village. This 19th century converted barn was beautifully preserved and showcases the exposed beams and wide board floors. Upon entering, one is enamored by the soaring vaulted ceilings with exposed beams in the center of the

PAULA REDMOND Corcoran Country Living

Timeless Elegance Meets Modern Comfort in the Heart of the Hudson Valley. Step into a world of refined charm and historic grandeur with this magnificent estate, originally constructed in 1867 and meticulously restored to preserve its legacy. Lovingly maintained over generations, the property blends classic architectural detail with the comforts of contemporary living, offering an unparalleled

Jillian Pajer Douglas Elliman Real Estate

This historic home was originally built in Millbrook, New York in 1733 by one of the nine partners of the early English land grant. The carefully maintained original architectural features reflect its heritage. On 10 ½ acres the property is a mixture of meadows and woods and bordered on 2 sides by a year round running stream. Clipped lawns surround the house and a privately situated

HEATHER CRONER William Pitt Sothebys Int Rlty

Luxury meets sustainability in this one-of-a-kind custom estate home nestled on 9 serene, wooded acres. Meticulously designed with an eye for elegance and a commitment to energy efficiency, this 4-bedroom, 3.5-bath residence blends sophisticated craftsmanship with modern environmental consciousness.Step inside to find wide-plank white oak flooring, soaring ceilings, and an abundance of

Rich Rundle Greenan Properties RE Agency

Nestled at the end of a quiet cul-de-sac in the charming, historic town of Hyde Park, this one-of-a-kind Hudson Valley estate offers the perfect blend of elegance, comfort, and resort-style living. Set on over 2.5 beautifully landscaped acres, the property features an expansive 4,766 sq ft primary residence, a spacious 1,600 sq ft multi-level pool house, and a luxurious heated in-ground saltwater

David Feinstein BHHS Hudson Valley Properties

Welcome to this stunning contemporary masterpiece, featuring a resort-style indoor pool and exquisitely designed spaces to suit every lifestyle. Offering over 6,000 square feet of beautifully finished living space, designed for those who appreciate modern style, open spaces, and effortless entertaining. Set on a private, tranquil property, yet just minutes from the vibrant Eastdale Village, this

Jake Garay Serhant LLC

Set amid the rolling hills of Pleasant Valley, The Gallagher offers a harmonious blend of financial opportunity and country tranquility, boasting nearly $200K in annual rental revenue. Designed for gatherings and getaways, this 5-BR, 3.5-BA home unfolds across an open, light-filled layout. The heart of the home is the expansive chef's kitchen - outfitted with dual convection ovens, a gas range

Alexandria Mickle Houlihan Lawrence Inc.

Why wait for new construction and settle for builder-basic when you can have THIS? Built in 2022 and absolutely loaded with upgrades, this stunning rocking chair front porch Colonial in the sought-after Arlington School District blends classic elegance with the modern features today’s buyers crave. Step inside to a bright, open layout designed for both everyday living and effortless

Jennifer Amicucci

Welcome to your dream home in the prestigious Mill Valley Estates, located within the highly-sought-after Arlington Central School District. This stunning colonial, nestled on over 2 private acres, offers an exquisite blend of luxury, comfort, and functionality. As you approach, a picturesque setting the lush landscaping greets you. Step inside to discover a meticulously maintained interior

Jennifer Lappe Keller Williams Realty

Highest and Best offers due by Friday 7/8 at 5:00 pm. Welcome to your private slice of paradise! This beautifully maintained 3–4 bedroom multi-level home sits on a serene 2-acre lot in one of Pleasant Valley’s most desirable neighborhoods. Whether you're hosting summer pool parties or savoring peaceful mornings on the sun porch, every corner of this property invites comfort and style. Inside,

Ellen Mallet

MULTIPLE OFFERS HIGHEST AND BEST 4 PM 7/7/25. One-Level Living at Its Best in The Gables! Welcome to this beautifully maintained home in the sought-after Gables Community. This light-filled, open floor plan offers effortless living with 3 bedrooms and 2 full baths, all on one convenient level. Step onto the charming front porch, perfect for enjoying warm summer afternoons. Inside, you’ll love the

Laurie Webber BHHS Hudson Valley Properties

Modern Farmhouse Retreat - Discover this beautifully reimagined 1870 farmhouse, set on over 25 private secluded acres in the heart of the Hudson Valley. Fully renovated in 2025 with modern finishes throughout, this 3-bedroom, 2-bath residence is a rare blend of historic charm and today’s design sensibility—perfect as a second home or peaceful weekend retreat.Tucked away down a long drive,

Curtis Darragh Legacy Land & Homes LLC

Welcome to Highview Estates located within the Arlington School District! This spacious and updated 1-bedroom, 1-bath garden-style unit offers approximately 850 sq ft of comfortable living in the heart of Poughkeepsie. Located on the lower level, Unit 416 features a bright, open layout with a large living room that opens to a private balcony—perfect for relaxing or entertaining. The kitchen

Ashley Bou KW MidHudson

Welcome to Timberstock Farm, a stunning property in the heart of Dutchess County horse country. This Adirondack-style estate offers a harmonious blend of rustic elegance and modern luxury, set on 33.26-acre lot with a pristine 9-acre pond. The bespoke stone and wood home boasts 4,592 square feet of living space sited at the highest elevation point on the property, casting views to the Catskills

Kyle Irwin Corcoran Country Living

Four bedroom, 3.5 Bathroom home in Hyde Park School District in the Town of Poughkeepsie on 0.58 acres! Wooded back yard. Configured with an accessory apartment building department says property is only a legal single family. Great opportunity to get in to the market and build sweat equity. Close to shopping, schools and amenities. Sold as-is. Buyer to pay NYS and any local transfer

Brian Smith River Realty Services, Inc.

Looking for 1 level living? This 2 Bedroom, 1 Bathroom Ranch in Town of Hyde Park might be for you! Hard wood flooring through out, Large open kitchen, living room with brick fireplace. Fenced in yard & rear porch Close to Culinary Institute, Marist College, FDR Estate, Dutchess Community College & Vanderbilt Mansion, shopping, schools and amenities.

Ernie Acampora River Realty Services, Inc.