Pleasant Valley, NY Homes for Sale under $500,000

Beautifully updated ranch, set on a tree-lined homesite in the Town of Pleasant Valley, offering the ease of one-level living with tasteful finishes throughout. The inviting floor plan features a welcoming entry foyer, hardwood flooring, sun-filled living room with bay window, and a bright kitchen with SS Frigidaire appliances and a Samsung refrigerator. The step-down dining room is perfect for

TINA TOWNSEND BHHS Hudson Valley Properties

New to market. Relaxed living in lovely, quiet neighborhood. Won't last long. Low traffic, cul de sac road close to everything you need. Sold as package deal: 3BR w/ full basement 46 Gleason Boulevard + next door 3BR w/ full basement 48 Gleason Boulevard for $750,000 total package price. Enjoy these 2 lovely homes on the top of the hill in beautiful & central Pleasant Valley. Live in one & rent

Thomas Zengen Thomas Zengen

WELCOME HOME TO 30 SMITH! Bring your vision to this spacious 3-bedroom, 1.5-bath Cape Cod offering over 1,300 square feet in the desirable Arlington School District. Ideally located in the heart of Pleasant Valley, this home combines privacy with convenience, just minutes from schools, shopping, parks, restaurants, and commuter routes. Full of timeless character, it features hardwood floors, a

Ronald Green KW MidHudson

New to market. Relaxed living in lovely, quiet neighborhood. Won't last long. Low traffic, cul de sac road close to everything you need. Sold as package deal 48 Gleason Blvd: 3BR w/ full basement 48 Gleason Boulevard + next door 3BR w/ full basement 46 Gleason Boulevard for $750,000 total package price. Enjoy these 2 lovely homes on the top of the hill in beautiful & central Pleasant Valley. Live

Thomas Zengen Thomas Zengen

Priced to sell and delivered completely vacant! This four-family investment opportunity, located at 234 Lakeshore Drive in Pleasant Valley, offers immense value-add potential in a convenient and accessible Dutchess County location. Perfectly positioned for savvy investors, this vacant asset allows you to immediately begin strategic renovations to maximize your rental income and build substantial

Joseph Lukic Compass Greater NY, LLC

Welcome to 47 Mountain View Drive a privately situated 4-bedroom, 2.5 bath raised ranch nestled on a quiet 1-acre lot in Pleasant Valley, NY. The heavy lifting is already done here. Major mechanical upgrades are complete including a new electrical panel, new PVC and copper plumbing lines, a new furnace, a water softener, and a newer water well pressure tank — giving you a rock-solid foundation

Jahnny Crespo RE/MAX Town & Country

The Ultimate Hudson Valley Retreat: Private Living Meets an Enthusiast’s DreamEscape to your own private, tree-lined sanctuary in Pleasant Valley. Tucked away in the highly desirable Arlington School District, this custom-built, 1.7-story residence offers the perfect blend of country living, efficiency, and unmatched mechanical utility. From the moment you arrive, the towering trees and

Christine Hamilton Keller Williams Realty Partner

Set high on a hill behind a hand-stacked stone wall, this little compound is a lot more interesting than its footprint lets on. The main house is a two-bedroom, one-bath charmer painted a moody near-black, with steel casement windows, wood paneling, and so much light it almost feels theatrical from morning straight through to evening. A separate studio building, a sloping wooded backyard, and one

Arlena Armstrong Anatole House LLC

Welcome to 1666 Main Street, a beautifully renovated classic early-1900s home in the heart of Pleasant Valley. This move-in ready property offers 3–4 bedrooms, 2 full baths, and over 2,000 square feet of living space on a low-maintenance .20-acre lot in the Arlington School District with low taxes. Inside, you’ll find refinished 100+ year-old Maple and Douglas Fir hardwood floors, upgraded

Kiyoshi Henson RE/MAX Town & Country

Fully Available Welcome to 23 DuPay Road in Pleasant Valley! Nestled on a beautifully landscaped lot surrounded by mature trees, this charming ranch offers the perfect blend of comfort, character, and convenience. Featuring 2 spacious bedrooms, 1 full bath and 1/2 bath, and gleaming hardwood floors throughout most of the home, this property is move-in ready while still offering room to make it

INGRID LEILADHAR eXp Realty

Discover your private retreat at the end of a peaceful dead end street with this enchanting, move-in-ready home. This charming 3-bedroom, 2-bathroom residence seamlessly blends cozy cabin vibes with tasteful, modern updates throughout. An abundance of windows floods the entire home with natural light, highlighting the warm and inviting atmosphere. The well-appointed kitchen is a chef's delight,

Samantha McCrory Exit Realty Connections

Nestled in a beautiful, private setting, this four-bedroom farmhouse offers the perfect blend of country character, warmth, and timeless appeal. Surrounded by natural beauty, the property provides the perfect setting for those seeking space, and tranquility. The sun filled eat -in-kitchen is warmed by a wood stove perfect for cooler weather, opens onto the stone patio. The living room features a

Janet Myer Houlihan Lawrence Inc.

Welcome to this amazing weekend retreat or year-round sanctuary, privately set on 4.71 beautiful acres with a peaceful babbling brook. Surrounded by nature’s beauty, this special property offers the perfect blend of privacy, comfort, and tranquility. Step inside to a dramatic living room featuring a vaulted ceiling, a wall of glass with southern exposure, and an abundance of natural light. The

Blake Michaud BHHS Hudson Valley Properties

Welcome to Your Private Creekside Oasis in Pleasant Valley, NY - 4 Bedrooms | 3 Full Baths | 1 Acre | w/Mother-Daughter Suite. Set far back from the road, this beautifully maintained 4-bedroom, 3-full-bath home offers the perfect blend of total privacy, natural beauty, and flexible living space. Minutes from Millbrook, Pleasant Valley, Hyde Park, Rhinebeck and many other Hudson Valley hot-spots.

Christopher Virtuoso KW Hudson Valley North