The median home value in Hillsdale, NY is $480,000.
This is
higher than
the county median home value of $390,000.
The national median home value is $338,100.
The average price of homes sold in Hillsdale, NY is $480,000.
Approximately 46.23% of Hillsdale homes are owned,
compared to 13.61% rented, while
40.16% are vacant.
Hillsdale real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Hillsdale real estate agent to arrange a tour today!
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 drive leads to the 7,200-square-foot Normandy-style residence with its stately stucco facade. Inside "Dragonfly'', the great room emerges as the heart of this extraordinary home, where soaring ceilings and dramatic walls of glass dissolve the boundary between interior luxury and a wall of white birches and the natural woodlands that lead to the private swimming pond beyond.Twin wood-burning fireplaces anchor this light-drenched gathering space, which flows to outdoor terraces and a dining room that adapts as gracefully to intimate family gatherings as it does to large dinner parties. The chef's kitchen has a professional-grade 48-inch range, generous island, and abundant storage, with a wall of french doors opening to a large terrace for summer gatherings.The primary suite is accessible via a sculptural staircase with a beautiful artisanal, wrought iron railing. The suite features a sitting room, spa-inspired bathroom with dual shower and soaking tub, walk-in closet, and a serene bedroom warmed by a gas fireplace. A private balcony offers a view over the estate's pastoral panorama.Four additional en-suite bedrooms are distributed throughout the residence, ensuring privacy and comfort for family and guests alike. The home's lower level spans the full footprint, including dedicated quarters for a caretaker."Dragonfly" is more than a home; it's a rare mix of architectural grace and a natural landscape that threads through the historic, stone walls to the private swimming pond and dock.For the discerning buyer seeking an extraordinary estate property in one of the Hudson Valley's most coveted locations, this singular offering is worth a visit.
This large 2-family home, circa 1888, in the Hamlet of Hillsdale is a rare find. The house consists of 2,500+ sq.ft. of living space, with five bedrooms and three baths, (public records show 4 bedrooms/2 baths) The 0.25-acre property is part of the Hillsdale municipal septic system, with a nice deep back yard that boast two, 2-car garages. Historically approximately 1940's housed a bakery and then later, approximately 1960's housed a general store. Each apartment has separate heat/100-amp circuit breakers. The wall studs go from basement to attic in one piece. Roof done in 1987. Updates across the board will be required. With housing in such short supply, the rehab of these units will produce big dividends. If you are in the market for an income property, or perhaps a spacious home, this is an opportunity you need to see.
Courtesy: BHHS Hudson Valley Properties
845-473-1650
Welcome home." We finally got our lake house honey." This is the dream of many, the memories of your home at the lake will remain beautiful from childhood to retirement. Our custom ranch has so many extras. This beauty offers 3 good-sized bedrooms upstairs, and two additional bedrooms/ office downstairs. The setup is a mother-daughter. Two kitchens, two living rooms, separate bedrooms, and separate entrances all connected from upstairs. The owners have lived in this home for 27 years. It's been their dream home. They describe it as "the most tranquil place on earth." They lovingly cared for it. Upgrades include: an updated heating system, roof, whole house generator, and updated septic system 1,000 gallon concrete. There are 1.10 acres of beautiful property to explore, plant a garden, and make your oasis. The lake is slightly visible from the backyard not lakefront but truly convenient. There is a right away for access at the community entrance. One of the most beautiful features is the three-season sunporch. Right off the porch is a double deck. Loads of storage. The owner states no water issues and the house is well insulated. He has records dating back to 1997. This is a solid home with plenty of room for extended family or possibly rent out the lower level for additional income and let this lake home pay for itself. COPAKE LAKE Conservatory is a wealth of information. Hudson, NY, and Great Barrington, MA. are convenient for shopping and other adventures. Have lunch or dinner at the Greens County Club and play 18 holes on the well-manicured golf course. Get out the fishing poles and pack your bags; it's lake time. Appliances: Gas RangeWater Softener Owned BuildingAreaSource: Other, ConstructionDescription: Aluminum Siding, Vinyl Siding, ExteriorFeatures: None, Flooring: Ceramic Tile, FoundationDetails: Block, InteriorFeatures: Storage, LaundryFeatures: Gas Dryer Hookup, In Basement, Laundry Room, Washer Hookup, LotFeatures: Back Yard, Front Yard, OtherEquipment: Fuel Tank(s), Generator, Utilities: Propane,
Wonderful southern exposure on one of the most scenic byways in Columbia County. Large parcels and restrictive covenants on abutting land. High fields and ancient tree lines dotted with maples and old stone walls. Nice mix of open and wooded to tuck your home into the hedge row without another home in site. Distant views of Catamount Mountain. Close to Hawthorne Valley School and the Berkshires. Usable land for horses or any animals. The perfect parcel to build your dreams on. Located in an area of fine estates, generational farms and old country farmhouses. Frontage on the Roeliff Stream. A true Eden.
Now You Can See Around Corners: Discover this extraordinary one-of-a-kind 1,700-sf octagonal contemporary barn home, conceived and built by its visionary owner, architectural designer Angela Patterson, and tucked away on more than four acres of woodlands on one of the most desirable streets in Columbia County. Boasting huge, pivoting picture windows that invite a flood of natural light and beautifully frame the natural surroundings, this one-level architectural gem offers a unique blend of modern elegance and rustic charm and truly re-defines country living. Inside, a soaring ceiling crowned by a cupola, as well as radiant-heat polished concrete floors enhance the airy, open-plan design. There's also an expansive floating propane-fired fireplace, a fully equipped designer kitchen that flows seamlessly into the living spaces, two loft-like bedrooms and two glass-and-stainless steel baths. This home is perfect for modern and sophisticated living and entertaining and is situated to provide ultimate privacy while being minutes from the charming Hillsdale hamlet, Hudson, and the cultural hubs of Egremont and Great Barrington in the Berkshires. A mere 2.5 hours to either NYC or Boston, this residence is an ideal full-time or weekend retreat for those seeking luxury, relaxation, tranquility, and convenience.
Contemporary compound perched amongst the oaks with spectacular sunset views over the hills and dale of Hillsdale. The 3 bedroom, 2-1/2 bath 2,218 square foot main home has a tree-top wrap-around deck with access from both the great room and a main floor primary en-suite which includes a laundry area, walk-in closet, and a bath configured with double sinks, separate shower and tub. The 25' x 22' living/dining area features a massive wood burning fireplace, vaulted 14 foot ceilings and picture windows offering a sweeping view overlooking the valley, pond and the hills beyond. The multi-level home also offers two lower level bedrooms with a full bath, and a few steps up from the main living area you will find a family room or office. Also on this level is the eat-in galley kitchen which is adjacent to a sky-lit yoga studio. The prior owner (a noted craftsman) had a well-ventilated workshop a few steps down from the main level and accessible from the attached two-stall garage, which could be whatever you need it to be: additional storage, a new in-house gym?From the home's thoughtfully planted entrance courtyard, follow the bluestone path to the detached garage, showroom and workshop, which can be reconfigured to your needs. With two very large half baths and two levels of open space, this somewhat blank slate can be reconfigured for whatever you desire -- a tremendous gathering place, a display space for large collections, a studio? In addition, this 4+ acre property is part of the Overlook Development association which maintains walking trails and a swim pond, within a short walking distance. Bring your vision to this wonderful property, which offers so much and has even more potential.
Create Your Own VisionEscape to 33.31 acres of untouched beauty nestled between Columbia County, NY, and Great Barrington, MA. This stunning parcel of wooded land offers complete privacy with no neighbors in sightjust you and the tranquility of nature.Imagine the possibilities as you explore the lush, wooded landscape teeming with wildlife. With over 1,677 feet of road frontage, access is easy. There is an old roadway, that climbs gently up a hillside that be used for your driveway. With some selective cutting, you may be able to get some nice views from your home site. With this parcel you'll feel miles away from it all. Whether you envision a secluded retreat, a dream home, or an outdoor sanctuary, this is a canvas waiting for your vision.Owner would consider short term financing for qualified buyers.Don't miss the chance to own your own piece of Columbia County. Schedule a visit today and start planning your future in this serene woodland escape!
Discover Your Dream Retreat: 49+ Acres of Serenity and Potential!Nestled between the charming towns of Chatham, NY, and Great Barrington, MA, this stunning parcel of over 49 acres offers a unique blend of privacy and accessibility. With impressive road frontage on two roads, this property is easily accessible while still providing a tranquil escape.Imagine waking up to the soothing sounds of the Cranse Stream, which gracefully winds through the wooded landscape, enhancing the natural beauty that surrounds you. The abundant trees provide a serene backdrop, perfect for hiking, wildlife watching, or simply enjoying the peace of nature.The property features a cleared building site where a home once stood, equipped with a unique artesian well that ensures a continuous supply of fresh water above ground, available 24/7. This means you can start planning your dream home or getaway without the hassle of drilling for water. In addition, there is an older septic system still in place as well as a rough drivewayWhether you envision a cozy cabin, a spacious family retreat, or an investment in your future, this land is ripe with potential. Explore the endless possibilities for recreation, gardening, or simply enjoying the great outdoors. Owner would consider short term financing for well qualified buyers.Seize this rare opportunity to own a piece of Columbia county that balances seclusion with convenience. Don't wait your dream property awaits!
Nestled on over 4 acres of serene land, this property features a private pond, fenced garden and renovated cabin offering a large studio living space. An attached 1-car garage, and wrap-around deck complete this cozy home. Additionally, there is a potential building site where an old abandoned home currently stands, offering opportunities for expansion.Situated on a quiet country road along the border of Massachusetts, this property ensures privacy while still being easily accessible. Enjoy the convenience of being just a short drive from Great Barrington, and only 15 minutes from Hillsdale, NY, and 15 minutes to the Mass Pike.Whether you're looking for a peaceful retreat, a weekend getaway, or a place to call home, this unique property is ready for new ownership to take it to its next chapter!
Courtesy: Elyse Harney Real Estate
518-789-8800
Discover the charm of this 1800s cedar-shingled home on 29 scenic acres in Hillsdale. The property features a heated pool, private tennis court, and meticulously maintained grounds. With 4 spacious bedrooms and 3.5 baths, it offers comfort and elegance. The living room has a working fireplace and opens to a bright dining room with a bluestone floor. The main-floor primary suite also has a fireplace for cozy nights, and an additional ensuite bedroom offers guest privacy or serves as a den. A three-season porch with a propane stove overlooks the gardens. Upstairs, find two more bedrooms and a full bath. Framed by stone walls, a serene pond, and fenced vegetable and floral gardens, the property is perfect for outdoor lovers with hiking trails leading to Catamount ski trails. Additional amenities include a three-car garage and generator, as well as proximity to Hillsdale Center and Great Barrington. A rare find in the Berkshires!
Secluded Hillsdale Contemporary on 27.7 acres with incredible far reaching views. Located off a scenic country road, the long private driveway leads to this 2200 square foot home. Originally built in 1970, the house has been upgraded with new windows and sliding doors which create walls of glass for enjoying the natural beauty of the surrounding landscape. The house features 3 bedrooms, 2.5 baths, a light filled great room with wood burning fireplace, maple floors throughout, cedar lined closets and cedar shake siding, metal roof, covered patio entry and an expansive wraparound deck. The detached 2 car garage has potential for a number of other uses. The property is a combination of open and wooded land with a meadow area and a spring fed pond. Wonderful area for outdoor enthusiasts with skiing, hiking and the rail trail close by. Only 8 minutes to Catamount Mountain Resort, 16 minutes to Great Barrington Airport, 30 minutes to Tanglewood and 35 minutes to Hudson Amtrak Station.
Commercial Rental for Service or Retail. Great location at Junction of Route 22 and 23, opposite Stewart's. Former real estate office on ground floor. 6 month lease, pay own utilities. Private bath.
Courtesy: Houlihan Lawrence Inc.
845-677-6161
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 all summer in your own pond. Pull a trophy buck in the fall. Hike to the peak and back country ski down in the wintertime. Be the first to catch a trout in your own private trout stream.
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 captures 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 you look you stop to take in the view, large bath with walk-in closet and laundry. The inner courtyard has a heated pool, sunken jacuzzi, outdoor shower, screened porch with fireplace and beautiful perennial gardens. Hidden off the drive is a guest cottage with open living area, bedroom and full bath.
Courtesy: Keller Williams Realty Partner
914-962-0007
This beautiful lot with breathtaking views is waiting for you to come build your dream home, exactly how you want it. With over 20 acres of raw, wooded land, you can create a compound of homes with your family or friends, or build a possible subdivision. This property offers the privacy you're looking for while still being close to town. Minutes from Route 23 and Taconic Hills School.
Perched at the top of the hill sits a curated, modern home overlooking the valley with stunning views of the Catskills and breath-taking sunsets. Next to the 1,000 acre Rhinestrom Hill Audubon Society wildlife sanctuary in Hillsdale, this perfect getaway is private yet minutes to everything. Grand room with fireplace, wet/coffee bar, and a wall of glass. Fully-equipped chef's kitchen. Wideboard, rift-sawn White Oak flooring. 3 ensuite bedrooms on main level. 5.5 baths. Primary suite with spa bath - double showers, dual vanities, soaking tub. Custom millwork throughout. Lower level playroom, movie theater, and sauna. Home office with separate entrance that could be used as an additional bedroom with full bath. Screened porch with infrared heaters and outdoor television. Heated saltwater pool with automatic cover, extensive hardscape patio, mature landscaping, fire pit, and storage shed/playhouse. Pool bunkhouse has two full-size day beds to sleep additional guests, a kitchenette and its own full bath. Geothermal heating & cooling. Whole-house backup generator. Oversized, 2 car garage.
Nestled into the hillside, this property is known as Springhill Farm, which dates back to the 1700s, an artist retreat. Since 2017, it has been recreated to combine a comfortable live and work environment. A Scandinavian inspired home and apartment built in 2019 & 2020 offer modern amenities and create a peaceful atmosphere. The 2 bedroom, 1 bath house features a large living space with a cozy woodstove for cooler months and large deck for entertaining and taking in the landscape. A barn apartment offers additional living space ideal for guests or rental income. Outside enjoy the expansive 25X50 barn, Cranse Creek, walking paths to a small pond, a fire pit, and an additional studio space. This property offers so much opportunity to live and work while enjoying the surrounding nature. With established rental history,Springhill Farm is ready to continue its journey to the next level.
Courtesy: Rouse + Co Real Estate LLC
845-750-0196
Located down a private winding drive The Passive House is an architect-designed modern home set amidst 15.7 wooded and pastoral acres. The home was designed and constructed to attain a rigorous level of energy efficiency and is a certified passive house (certified by the Passive House Institute US (PHIUS)). Conceived as a fossil-fuel free, all-electric home, solar panels work to bring this house close to net-zero. An ERV (Energy Recovery Ventilator) system is built into the HVAC, ensuring that fresh, clean air is circulating throughout every room at all times. The home is positioned to capture southern light and distant views. A bright, welcoming foyer leads to the first wing, which includes a bedroom, office space, full bathroom, and mechanical room. Steps lead past a powder room into the heart of the home a spacious, open-concept kitchen / dining / living area featuring 13-foot ceilings and floor-to-ceiling sliding doors that frame bucolic meadows and Catamount Mountain views. Beyond the living room, the west wing of the home has a media room/second living room, and a hall that leads to the additional two bedrooms, a second full bath, and the primary bedroom with ensuite bathroom. All bedrooms feature high quality triple glazed windows and doors. Enjoy indoor spaces that flow easily to the outdoor spaces creating a beautiful modern aesthetic blending seamlessly with nature. A 3-car garage pre-wired for EV charging and back bluestone patio complete this offering. Located in Hillsdale just minutes from the hamlet, 15 min to Great Barrington, and under 30 min to both Hudson and Millerton.
Courtesy: BHHS Hudson Valley Properties
845-473-1650
A Lake house in the country is perfect for those seeking a simple way of life. You'll feel like you're living in a storybook. Watch your story unfold before your eyes. Leona's Country Cottage is not your average cottage. It was architecturally designed and built to last many years to come. A new rebuild from the foundation up between 2020-2021 With all new requirements for efficiency and new code requirement for electrical and plumbing, you're getting one of the best constructed homes on Copake Lake. It's a perfect blend of modern craftmanship and comfort. Regarding value consideration, Copake Lake Real Estate is rarely available in this private community and has no HOA. New builds are selling from 620k to millions. The construction plans, survey and CO are available upon your request. There is direct access to the lake from the cottage. A newly constructed staircase will bring you to your dock. Deeded Right away & lake rights come with your ownership and a shed for storage. Important details: Septic is a 500 Gallen Poly Septic installed in 2011. Propane is owned, Electric is 200amps. 3 Ductless systems -Provides heat and air. Electric Company is NYSET. Yearly cost 1200. COPAKE LAKE Conservatory is a wealth of information. All appliance included in sale. Hudson NY and Great Barrington Ma. is convenient for shopping and more adventures. Have lunch or dinner at the Greens County club and play 18 holes on the well-manicured golf course. Get out the fishing poles, pack your bags its lake time. Note: Part of the front steps up to the house are owned by neighbor to the left. Survey pin near steps angles to metal post. Right away to lake is for multiple people to use as per deed. The dock, shed and lower-level land is owned by the current owner- The right of way is for 3 neighbors for access only as per deed. Additional Information: Amenities:Stall Shower, Appliances: Electric Water Heater ConstructionDescription: Vinyl Siding, InteriorFeatures: Built-in Features,
Very private location at end of dead end road. Access to Route 22 and the Taconic Parkway. Easy drive to Hudson, Hillsdale, Catamount Ski Area and Great Barrington.
Prime Commercial Property for Sale at the Heart of Hillsdale, NYLocation, Location, Location! Discover this exceptional commercial property perfectly situated at the bustling intersection of Route 22 and Route 23 in Hillsdale, NY. This high-visibility location sees significant daily traffic, making it an ideal spot for a variety of businesses looking to attract customers from near and far.Property Highlights:Renovated to Perfection:This building has been completely renovated , offering a fresh, modern space for your business needs.State-of-the-Art Systems:Benefit from all-new electrical systems and a cutting-edge Mitsubishi Electric Heating and Cooling System, ensuring a comfortable environment year-round.Prime Location:Just 16 minutes from Great Barrington, MA, and 25 minutes from Hudson, NY, this property enjoys easy access to major nearby towns. Plus, it's a quick 5-minute drive to the popular Catamount Mountain Resortperfect for attracting visitors and outdoor enthusiasts.Whether you're looking to establish a new retail location, open a professional office, or start a unique venture, this property offers an unbeatable combination of location, modern amenities, and convenience.Don't miss this opportunity to be at the center of it all. Contact me today to schedule a viewing and make this prime commercial property the new home for your business!
Courtesy: Four Seasons Sothebys Intl
518-822-0800
Purchased by the Foster family in 1790, this property encompassed the majority of what is now the Historic Hamlet of Hillsdale. Sited in the center of the Hamlet, this Greek Revival home, built in 1810 by Isaac Foster, who inherited the land from his father. Prior to 1790, the property was in the family of Catherine Van Renssalaer Schuyler - mother-in-law of Alexander Hamilton. The home has been recently renovated to preserve its historic value as the third oldest house in town. With its large backyard and mature trees, the property was fully restored to respectfully celebrate its grandeur and elegance. This designer-ready, stylish farmhouse offers a unique opportunity to anyone wanting a turnkey property in the majestic Hudson Valley. The renovation included a new dual-zoned centralized heat and cooling systems, new plumbing, electrical wiring, water heater and furnace, structural re- stabilization, and a replaced roof. All new appliances were installed, including an upstairs laundry space with stacked Samsung washer and dryer. The walls, plaster and paint have been fully re-finished. Antique glass was used to restore the period windows, and original wood flooring was kept and restored to offer warm and cozy interiors. Upon entering, there are warm oak floors, view of both the living-room and formal dining room, windows' with unique casings, an example of Greek Revival design, and the fireplace features two original miniature carved Greek friezes guarding either end of the mantel. The spacious kitchen, a walk-in pantry, granite countertops, new Bosch appliances, and informal dining space. Carrara marble in both bathrooms with a full suite of traditional-styled fittings. The primary suite features a vanity set, soaking tub, separate shower. There can be up to 4 bedrooms, (including a first-floor mother-in-law style apartment with private entrance and bathroom with a shower). The home offers a flexible floor plan for use as a residence, a business, or dual use - the building is zoned as both commercial and residential. Situated halfway between Hudson, NY and Great Barrington, MA, walking distance to amenities of Hillsdale Hamlet, a general store, florist, kitchen store, brewery, restaurants, coffee shops, and grocery store with wine shop. Catamount skiing, hiking trails, lakes, and walkable access-point to the Rail Trail.
Overlook Forest boasts one hundred and fifty beautifully wooded acresin eastern Hillsdale. This lush setting is ideal for a private retreat, family compound or camp. There are trails and stonewalls throughout the property. Rock outcroppings, seasonal streams, and plenty of ferns and mountain laurel create a magical woodland garden. Potential mountain and distant views can be had in all directions. The property lends itself to recreational activities such as hiking, cross country skiing and snow shoeing. Downhill skiing is just minutes away. The land is conveniently situated with easy access to everything the Hudson Valley and Berkshires have to offer. Just two hours and fifteen minutes from NYC.
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