Columbia County Real Estate Specialists logo

Real Estate Brokerage Services in Columbia County, NY

Homes Over $500,000

Columbia County Real Estate Specialists is proud to offer these fine homes and country estates for sale. Take your time to browse our gallery of exceptional properties throughout Columbia County. Call us at (518) 325-9784 and we will be happy to assist with your search in any way that we can. The right home, land parcel or country estate can be found with the Realtors® of Columbia County Real Estate Specialists.

----describe photo---

Hillsdale Homestead

177 Old Town Road, Hillsdale, NY

MLS # 149688

This impeccable 1890's Hillsdale home is a beautiful combination of original character, tasteful updating and fine craftsmanship. The quaint 3-bedroom, 2-bath, center hall eyebrow colonial is as special as they come, semi secluded on a back road, close to town. A stylish entryway addition features copper gutter, period details, standing seam roof and magnificent front door. You will enjoy the bright and airy kitchen featuring exposed beams, vaulted ceiling, hardwood floor and skylight. The warm open kitchen-dining room-living room floor plan includes a great room with built-in shelving, coffered ceiling and original wide-board floor. Board and batten interior doors with original hardware and handcrafted radiator covers add to the overall character and charm. The home has been well maintained and wrapped in cedar siding. It is set up beautifully for entertaining with an extensive white oak wrap-around deck overlooking the private back yard and babbling Mud Creek trout stream. There are two substantial outbuildings. A detached heated garage with studio space above and a (28x32) heated shop with full insulated basement below. Private, secluded and close to everything. Make this special property the home you'll treasure forever. *Main house has 3 bedrooms, 2 baths. *Studio/Office above garage has small kitchen, laundry and bathroom. *Workshop heated with 2 levels, many possibilities for this great space. *Basement, well insulated, perfect for home gym/storage space.

Perfectly located in the Hillsdale Hamlet, getway to the Berkshires, this property is just two hours from NYC / Boston with easy access to Tanglewood, the Berkshire International Filf Festival, Jacob's Pillow Dance Festival, Hancock Shaker Village and so much more. 3+ bedrooms, 2 baths on the corner of Cold Water Street & Maple Street.

Listing Agent: Margaret Bower Avenia, Principal Broker

----describe photo---

Residential / Commercial ~ Sale Pending

10394 Route 22, Hillsdale, NY

MLS # 145815

Charm is everywhere in this early 20th century turnkey farmhouse on 6 glorious acres with million- dollar views.  Beautiful original details throughout the home, including a classic living room that features a bay window, wood floors and the original fireplace. Numerous improvements have been made by the owners including a standing seam metal roof, updated stainless kitchen with Viking range/hood, new barn roof in 2011, new furnace and fuel tank in 2014 and insulated window replacements in 2016. The 6-acre parcel features gently sloping lawn and pasture, wonderful views from North Hillsdale to Catamount, a kidney shaped in ground pool, an additional 2-story garage and the original outhouse.The property is zoned residential-commercial and was most-recently home of Hillsdale Barn Antiques. The extraordinary post and beam barn offers three stories of open floor space ideal for antiques, Yoga, Music or art studio, dry storage, or even as a venue for weddings and other events. Historic homes don't become available often. Particularly ones in excellent condition with breathtaking views and the unlimited potential offered by the spacious barn and garage buildings.

Listing Agent: Margaret Bower Avenia, Principal Broker

Four Maples, Hillsdale NY

1790 Center Hall Colonial

3728 Route 9G, Germantown NY

MLS # 147133


Discover this opportunity to own an historic Hudson Valley mini-farm. The 1790 Center Hall Colonial is situated on a 5-acre parcel that includes a 2-story barn, horse barn, fenced paddock, in-ground pool, large pool house and additional outbuildings. The generously sized home has five bedrooms plus den, a full bath on each level, large living room with fireplace, sunny dining room, large eat-in kitchen, wide board planks wood floors throughout and classic covered front porch. The large barn contains two garage stalls, a workshop and second story hayloft just waiting to be converted into whatever can be imagined. PLUS, another barn with horse stall and fenced in run. The southern Columbia County location is ideal in so many ways. Only a short distance to Amtrak stations in either Rhinebeck or Hudson, Olana, Clermont State Park, boating on the Hudson River and fun things to do in every direction. Come see what makes this special property such an exciting opportunity..

Listing Agent: John A. Avenia, Associate Broker

Four Maples, Hillsdale NY

Quainte Copake Falls ~ Sale Pending

610 Breezy Hill Road, Hillsdale/Copake Falls, NY

MLS # 147266

Breezy Hill Road is well known as one of Columbia County's most sought-after destinations, featuring breathtaking views, high-end homes and close proximity to Catamount Ski Area, the HVRT, Bash Bish Falls and the Berkshires for fine dining and entertainment.

This charming 1940's single-story home features 3 bedrooms, 3 baths, hardwood floors throughout and a stunning stone fireplace. Sited high above Breezy Hill on over 15 glorious acres overlooking the sprawling front lawn and distant Western views to the Catskills, the home is surrounded by nature and totally secluded. Numerous recent improvements include upgraded electrical and water systems, chimney repairs, re-building the driveway, tree removal, new fuel oil tank, new appliances and high-speed internet access. If you are searching for a home in Columbia County and believe in the axiom "Location - Location - Location" this property checks all the boxes.

Listing Agent: Margaret Bower Avenia, Principal Broker

Breezy Hill Rd Copake Falls

127 Pristine Acres w/1850's Farmhouse

66 Fado Road, Craryville, NY

MLS # 146009

The popular phrases Diamond in the Rough'' and Complete Package'' are accurate descriptions of this unique property. At an asking price under $800,000 it is a tremendous value offering a wide array of features. Two tax parcels totaling 127 acres of grass fields, timber stands, wooded hillside, wetlands, stream and pond. A completely secluded setting ideal for a family compound. Bordered by a 400-acre organic farm and 1,000-acre Rheinstrom Hill Audubon Sanctuary. Well suited for organic farming and/or raising animals. An 1850's Eyebrow Colonial with fireplace, hard and wide-board floor and original details. A substantial amount of updating will be needed, but well worth the effort. Nice Post & Beam barn with hand-hewn beams. Ideal Columbia County Location within 20 minutes of Hudson and Great Barrington. Substantial properties - in sought after areas - don't come on the market often. Taking advantage of this special opportunity can pay dividends for years and generations to come!

Listing Agent: John Avenia, Principal Broker

Circa 1880 Spencertown home for sale

POSSIBLITIES ABOUND!! ~ Motivated Sellers

9494 Route 22 / 2 Tri Brook / 7 Tri Brook, Hillsdale, NY

MLS # 144879

FOUR BUILDINGS / Family Compound or Income Producing Investment - your choice!! There are four residences spread across 2 acres in Hillsdale. The main house was renovated in 2022; it features 3 bedrooms, 2 bathrooms along w/open floor plan living room with wood burning fireplace / dining room and large utility laundry room. In addition, there are two - 1 bedroom apartments and a second single family home featuring 3 bedrooms and 1 bathroom. In total there are four residential rental units across three buildings, plus a garage/workshop/storage build. The infrastructure is sound with one well and three 1,000 gallon septic systems servicing the four units. Broadband internet service is available. Each unit has its own heating and electric service. With four rental producing units this is a rare investment opportunity in an area desperate for residential rental units. BRING ALL OFFERS ~ MOTIVATED SELLERS

Listing Agent: John Avenia, Associate Broker

Four Maples, Hillsdale NY

'Unique & Special' don't do this Justice ~ Sold for $755,000

46 Collins Street, Hillsdale NY

MLS # 137189

Side Hall Colonial, Circa 1850 defined by its stunning details as one of Hillsdale's iconic properties. Featuring, beautiful wood floors thought out, three bedrooms, two baths, a dining room, living room, den (or forth bedroom), enclosed rocking chair front porch and spacious kitchen that is absolutely filled with natural light, PLUS a handsome stone outdoor fireplace. Surrounded by spectacular grounds including 100-year old maples, flowerbeds, large vegetable garden and TWO extraordinarily sites for in-ground pool. It also offers a converted run-in horse barn to now a beautiful Artist Studio or office. This classic property has been exquisitely restored and cared for by the current owners. If owning a piece of local history is important to you this is the opportunity you've been waiting for. Unique properties like this don't present themselves often, be sure not to miss it! Excellent location with City of Hudson approx 20 miles, Berkshires 15 minutes & NYC approx 2 hours.

Listing Agent: Margaret Bower Avenia, Principal Broker

Bash Bish Falls

Come Home to Peace & Harmony ~ Sold for $585,000

27 North Mountain Road, Copake Falls, NY

MLS # 142414

This magnificent property boasts some of the finest Charming 1890's Victorian farmhouse with two-story barn (w/horse fencing) on 5+/- acres with the Taconic State Park/Bash Bish Falls (i.e. walking distance to hiking trails, swimming & thousands of acres of protected land). Just steps away. Three bedroom home, two full baths, custom kitchen, hard wood floors throughout, front sunporch, rocking-chair back porch overlooking a beautiful barn, field of wildflowers, your own private pond 🙂❤️ & peacefulness. Living room was originally the master bedroom ensuite, which could easily be a first floor MBR again. Find inspiration and let 27 North Mountain Rd., Copake Falls be your happy place & let good times and happiness begin. Needs some work but well worth it. Property borders Harlem Valley Rail Trail.

Listing Agent: Margaret Bower Avenia, Principal Broker