Hillsdale, NY Homes for Sale with Garage

A Home of Distinction -- there are two distinct sections of this 4+ BR, 4.5 BA, 2 office spaces, 3,666 sf home that is sited on 18.5 private acres. Wood-burning fireplace, 2 gas wood stoves. Pond with gazebo. The main section has 3 BR's, living room, family room, eat-in kitchen, access to the deck with Catamount views and an attached 2-car garage. The addition has a welcoming entrance, 1 BR.

Lindsay Lebrecht Copake Lake Realty Corp.

Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side brings in the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

AUCTION BIDDING OPEN: Bidding ends September 17th. Previously listed at 8.85M. Current high bid 2.5M. Open House Saturday and Sunday, and showings available daily by appointment.An extraordinary architectural masterpiece awaits at The Bald Mountain Estate, commanding eighty-five pristine acres atop Columbia County's highest peaks. This four-building contemporary compound epitomizes Hudson

Rachel Haley Houlihan Lawrence Inc.

Nestled on a hillside just outside the vibrant hamlet of Hillsdale sits this exceptional 2007 Cape Cod cedar sided home. The views are simply one-of-a-kind, directly overlooking the Rheinstrom Hill Audubon Sanctuary and offering distant views reaching from the Taconic Range to the Catskill peaks. Energy saving features include a geo-thermal heating and cooling system, fully conditioned

John Avenia Columbia County RE Specialist

This picturesque four-bedroom, three-bath 1800's farmhouse has been lovingly restored and thoughtfully updated, blending timeless historic farmhouse charm with modern comfort, including fiber-optic internet. Set on 18.5 acres of pure serenity, it offers a storybook setting with two meandering streams, an enchanting spring-fed pond,and a rolling lawn that opens to forests and trails.

Nancy Felcetto Brown Harris Stevens Hudson

1940's stone cottage sited on 10 acres along the Green River. Main house has a lovely kitchen, with center island and soapstone counters, open to the dining area with French doors to screened porch. Stone fireplace in the living room with recent gas insert for ease of use. There is also a small den, full bath and laundry on this level. Upstairs there are two bedrooms, a hall bath and landing

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

This handsome Greek Revival sits on a quiet street occupying a generous village lot in the historic Hamlet of Hillsdale. Built around 1848, the home feels historic and fresh with plenty of room to spread out. A wide front porch with Doric columns welcomes you inside to a central foyer. To one side, a front parlor opens to a spacious dining room with elegant moldings. The kitchen is a highlight,

MATTHEW CAREY Rouse + Co Real Estate LLC

Historic Upstate NY Sanctuary - 8.7 Magical Acres in Hillsdale, NY - known for its scenic beauty and small-town charmEscape to your own private paradise on this enchanting 8.7-acre property featuring a charming 1820's cottage, pristine swimming pond with waterfall, and endless outdoor adventures. This secluded sanctuary offers the perfect blend of historic character and natural beauty, just

Chris Getman Houlihan Lawrence Inc.

Elevate Your Lifestyle in Columbia CountyDiscover the pinnacle of modern luxury in this extraordinary Columbia County estate, set against the breathtaking backdrop of the Berkshire Hills and Catamount Mountains. Spanning over 10 meticulously landscaped acres, this architectural gem blends serene country living with sophisticated design.Step into a grand double-height foyer that

Christopher Halliburton Beach & Bartolo Realtors

Peace and seclusion on a private road.Pass through a stone gate and travel a long, winding driveway to reach this exceptional property, quietly nestled into the mountainside. The setting is serene, with only the sounds of birds and the breeze in the air. From its elevated position, the home offers uninterrupted, layered views of the Berkshire mountains stretching far beyond to distant

John Barbato Compass, Hillsdale

Ultra-private dead-end lot overlooking Hillsdale, this extraordinary home offers some of the most breathtaking panoramic views in the entire Hudson Valley. Set on 11.9 totally private acres, the property is a rare combination of refined living and natural serenity, with a gentle stream meandering below and a charming footbridge crossing over—straight out of a storybook. There is even a pond with

Michael Castellano Gilcrest Properties

Nestled along a picturesque, secluded country dirt road--surrounded by a serene pond, a flowing creek, and wooded acreage--this charming 2 bedroom log cabin offers the perfect escape. The expansive property spans 193 acres, with 18 acres located outside the Columbia Land Conservancy and Forestry Program, allowing for reduced taxes and enhanced privacy.An additional structure on the

Janet Kain The Kinderhook Group, Inc.

Price reduction.1800s farm house. Just waiting for some TLC. This property consists of the main farm house. one very large barn. Addtional 3 out building. One of the back building contains an attractive apartment.The property butts up to the Harlem Valley Rail Trail. Walking distant to the Hamlet of Hillsdale. Including the Roe Jan Brewing Co. IGA, The Hillsdale House, The town park. Less then 5

Gerard Meenagh The Meenagh Group Realty

Ridge Lane in Hillsdale is the perfect country retreat. Set on 7+ acres on a quiet dead end road. This newly built farmhouse captures the charm and solitude that make Hillsdale so desired. Come in to the mudroom, kick off your shoes and enjoy the space of a real country kitchen. The open living space flows easily to the dining area and living room or out to the deck to enjoy the blue sky. An

Emma French Gabel Real Estate

Where Norman charm meets Hudson Valley splendor, "Dragonfly" stands as a fine example of country living - a rare 130-acre estate that marries grand European sophistication with the pastoral beauty of Claverack. Just twenty minutes from the cultural centers of Hudson and the Berkshires, this property strikes a balance between secluded sanctuary and connected countryside living.A winding private

Chris Getman Houlihan Lawrence Inc.

Minutes to Great Barrington, this 300 acre wilderness provides waterfalls, stream frontage, pond frontage and something for every outdoor enthusiast. Own your own mountain with trails throughout for hunting, hiking and camping. Build your dream house overlooking a stocked pond and classified trout stream while staying in the 3 bedroom 3 bath caretakers house. The possibilities are endless. Swim

Andrew Gates Houlihan Lawrence

Rarely available private gated island property, offered below market value.Sought after and water-front home on a private island in the middle of the only high-speed motor boat lake in Columbia County. A modern lake cottage and carriage house on 1.1 acres with four-season hot tub, large private dock and over 100ft of direct water frontage.The main house has 2 proper bedrooms and 2 full bathrooms,

John Barbato Compass, Hillsdale

New construction home on a private gated island with the possibility to customize further for 2026 completion.Exclusive location on a private island in the middle of the only water ski motor boat lake in Columbia County. A contemporary house on 1.1 acres with a large private dock and over 120ft of direct water frontage on Lake Copake. This beautiful home has 5 proper bedrooms (with the

John Barbato Compass, Hillsdale