Vintage homes for sale & real estate in 12529, NY

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ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
Updated home on 1.4 acres offering 2,430 sq ft of living space. Major improvements completed within the last 5 years include roof, plumbing, flooring, kitchen updates with oak countertops, cabinets, and appliances, log siding, and more. Features a partially finished basement with a bedroom and rec room potential. New septic system installed approximately 2 years ago, plus a newer well pressure pump. Second-floor bathroom is partially finished and awaiting final touches. Great opportunity to complete remaining updates and make this property your own.

$309,900

3 beds1 bath2,430 sq ft

84 Connelly Rd #53, Hillsdale, NY 12529

Oak countertops • New septic system • Updated home

ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
A little house with a lot of soul. Set on a quiet village street in the heart of Philmont, this charming two-bedroom home makes thoughtful use of every inch of its compact footprint. Inside, warm wood ceilings, exposed beams and brick, a wood stove and an open kitchen and living area give the house a relaxed, creative character. Large windows bring in plenty of natural light, while the simple, unfussy interiors feel both rustic and modern. Outside, the fenced backyard is a surprisingly private little oasis, with established plantings, room to garden and dine outdoors and a sweet detached studio/workspace with French doors, a perfect spot for art, writing, yoga or simply getting away from th

$335,000

2 beds1 bath806 sq ft

4 Summit St, Philmont, NY 12534

Access to nature • Detached studio • Fenced backyard

ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
Three buildings on two adjoining Church Street parcels, conveyed together, all vacant. 5 Church Street is four units, broom-clean and cosmetic: wide-plank pine already refinished, plaster sound, original moulded casings and baseboards intact, a three-sided bay with a curved ceiling, and a varnished panelled entry with its dentil shelf, cast escutcheon and period bell. It wants exterior paint, porch repair and tenants. 7 Church Street is the showpiece -- full-height round tower, curved colonnaded porch on classical columns, leaded gable light, envelope sound, laid out as separate residences. Behind it stands a third building, stripped to framing with a concrete foundation: demolition sunk, s

$895,000

7 beds— baths— sq ft

5 Church St, Philmont, NY 12565

Four units • Three sided bay • Curved ceiling

ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
PRICE REDUCTION - Under 300,000 dollars on Copake Lake! Welcome to 81 SW Colony Road, a charming 2-bedroom, 1-bath bungalow now offered at a newly adjusted price point that makes owning a piece of Columbia County paradise more accessible than ever. Experience the quintessential upstate lifestyle just over two hours from New York City and 30 minutes from both the Hudson and Wassaic train stations--perfect for a weekend escape, summer lake house, or year-round getaway. Take an immediate look inside with our 3D Virtual Tour on Homes.com to explore this unique property, which boasts 15 feet of coveted, deeded access to the pristine, 425-acre waters of Copake Lake. Adventure awaits in every dire

$299,888

2 beds1 bath736 sq ft

81 SW Colony Rd, Hillsdale, NY 12529

Taconic state park • Bash bish falls • 6,534 sq ft lot

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
Welcome to Hawthorne Cottage, a circa 1900 updated residence on Main Street in the heart of Philmont's historic district, set on a sloping lot with a stone wall and partial woodland in one of Columbia County's most authentic small villages. The home has been fully renovated. Open shelving and curated details create inviting living spaces full of warmth and character. The kitchen includes butcher block counters, a herringbone tile backsplash, stainless steel appliances, and striking navy cabinetry accented by brushed brass hardware. New laminate floors run through every room and bathrooms have been updated. The cozy layout spans 1,392 square feet, with a half bath on the first floor and thre

$325,000

3 beds1.5 baths1,392 sq ft

152 Main St, Philmont, NY 12565

Fully renovated • Navy cabinetry • 9,147 sq ft lot

Listing by Houlihan Lawrence Inc

Property at 2955 State Route 23, Hillsdale, NY 12529, 3 beds, 2 baths

$849,900

3 beds2 baths1,600 sq ft

2955 State Route 23, Hillsdale, NY 12529

Listing by Coldwell Banker Advisor Realty

Property at 81 Black Grocery Rd, Hillsdale, NY 12529, 3 beds, 2 baths

$624,000

3 beds2 baths1,475 sq ft

81 Black Grocery Rd, Hillsdale, NY 12529

Listing by Houlihan Lawrence, Inc

Property at 2999 New York 23, Hillsdale, NY 12529, 4 beds, 2.5 baths

$725,000

4 beds2.5 baths2,225 sq ft

2999 New York 23, Hillsdale, NY 12529

Property at 100-102 Main St, Philmont, NY 12565, 4 beds, 5 baths

$525,000

4 beds5 baths4,400 sq ft

100-102 Main St, Philmont, NY 12565

Property at 335 Dawson Rd, Hillsdale, NY 12529, 5 beds, 5.5 baths

$3,485,000

5 beds5.5 baths5,083 sq ft

335 Dawson Rd, Hillsdale, NY 12529

Listing by Brown Harris Stevens HV LLC

Property at 95-97 Main St, Philmont, NY 12565, 6 beds, 4 baths

$535,000

6 beds4 baths5,800 sq ft

95-97 Main St, Philmont, NY 12565

Property at 9960 Route 22, Hillsdale, NY 12529, 4 beds, 3 baths

$1,250,000

4 beds3 baths2,395 sq ft

9960 Route 22, Hillsdale, NY 12529

Listing by Four Seasons Sothebys Intl

Property at 2666 New York 23, Hillsdale, NY 12529, 3 beds, 4 baths

$1,100,000

3 beds4 baths2,880 sq ft

2666 New York 23, Hillsdale, NY 12529

Property at 90 W End Rd, Hillsdale, NY 12529, 4 beds, 2 baths

$3,600,000

4 beds2 baths3,200 sq ft

90 W End Rd, Hillsdale, NY 12529

Property at 2666 Ny-23, Hillsdale, NY 12529, 3 beds, 4 baths

$1,100,000

3 beds4 baths5,000 sq ft

2666 Ny-23, Hillsdale, NY 12529

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ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
Welcome to 1100 Harlemville Road, a c. 1850 farmhouse set on more than nine bucolic acres with sweeping views across the Taconic Hills. Perched above the road, the property enjoys a sense of privacy and a setting that feels quintessentially upstate. The drive approaches the rear of the home, where a covered porch offers the perfect vantage point to enjoy the landscape. Enter through a mudroom clad with vibrant wallpaper. Checkered tile floors lead to a spacious country kitchen; patterned tin accenting the walls lend character and texture. A generous pantry conceals the refrigerator while providing ample shelving and storage. The kitchen flows seamlessly into the dining room, anchored by a w

$1,300,000

3 beds2 baths1,858 sq ft

1100 Harlemville Rd, Ghent, NY 12075

Bucolic acres • Covered porch • Generous pantry

Listing by Rouse + Co Real Estate LLC

ABOUT THIS HOME
Vintage Home for sale in 12529, MA:
Recently expanded, neat-as-a-pin cottage in the village of South Egremont. This sweet home feels like a retreat, but it's conveniently located minutes away from shopping, restaurants, skiing, and all that town has to offer. Thoughtfully and tastefully updated, this home has a gracious primary suite, with spacious bath with high-end finishes, walk-in shower and separate bathtub, large walk-in closet, and large sliding doors to a private deck. The guest bath has been renovated with the same thought and attention to detail. An additional deck off the main living area, and a screened-in porch invite you to take a seat, relax and enjoy the peaceful country setting.

$545,000

3 beds2 baths1,288 sq ft

52 Sheffield Rd, Egremont, MA 01230

Private deck • Screened-in porch • Expanded cottage

ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
Opportunity awaits as this super cozy year-round unique 3bedroom 1.5 bath traditional retreat with an awesome huge deck which overlooks the High Falls State Conservation Area and Ogowamuck creak hits the market! This home features a large cozy family with hardwood floors, large eat in kitchen, huge 3 season sun porch, living room with custom bar, laundry room, den! Centrally located to everything including the Conservation area features hiking trails, trout fishing and Waterfall! A must see!

$250,000

3 beds1.5 baths1,536 sq ft

57 Main St, Philmont, NY 12565

3 season sun porch • Eat in kitchen • Custom bar

Listing by Newcomb Realty Group LLC

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 12529, MA:
Charming North Egremont Village colonial. This sweet New England village farmhouse sits tucked into the loveliest setting with a rocking chair front porch, lovely gardens, mature shade trees and a white picket fence. The first floor holds a comfortable open living / dining room with a wood burning fireplace, a wainscotted kitchen, sunny family room, and a full bath with laundry. Upstairs are 3 comfortable bedrooms, a full bath with lots of storage, and a sunny deck off the primary bedroom. Close by is French Park for tennis, and the North Egremont store is just a short stroll away. Also nearby is Prospect Lake for swimming, paddle boarding, and kayaking , as well as the Cliff House, for la

$749,000

3 beds2 baths1,852 sq ft

11 Prospect Lake Rd, Egremont, MA 01252

Wainscotted kitchen • White picket fence • Sunny family room

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
Discover the possibilities in this charming farmhouse, originally built in 1850, set on 9.3 acres (comprised of two lots. the house is on 3 acres and the barn is on 6.3 acres) of land offering a mix of open fields and wooded acreage. The property features 2/3 bedrooms and 2 full bathrooms, along with a flexible additional room that could potentially be used as a fourth bedroom, den, home office, or studio, depending on your needs. Outside, the property offers a peaceful rural setting with an open field, a wooded portion providing privacy and natural beauty, and an old barn that adds to the property's historic farm character. With ample acreage and a variety of potential uses, this property

$525,000

2 beds2 baths1,490 sq ft

1798 Harlemville Rd, Chatham, NY 12037

Old barn • Country homestead • 9.3 acres

OPEN TODAY, 11:30AM TO 1:30PM

ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
Set on just over six acres along a quiet country road, 861 Snydertown Road is a charming Hudson Valley retreat where open meadows, mature plantings, and three picturesque ponds create a wonderfully private setting. At the heart of the property is a remodeled 1930s country cottage with three bedrooms and two baths. Warm pine floors, abundant natural light, and an easy, relaxed character define the home. The inviting kitchen features a deep cast-iron sink, gas range, stainless steel appliances, and plenty of country charm. Move-in ready, with updated mechanicals, the cottage offers an effortless escape to the Hudson Valley. Outside, the property truly comes to life. Lilacs surround the expans

$524,000

3 beds1.5 baths2,356 sq ft

861 Snydertown Rd, Claverack, NY 12521

Inviting kitchen • Fenced garden • Six acres

Listing by The Kinderhook Group, Inc.

Property at 4 Sheffield Rd, South Egremont, MA 01258, 3 beds, 3 baths

$1,295,000

3 beds3 baths3,048 sq ft

4 Sheffield Rd, South Egremont, MA 01258

Property at 2934 County Road 7, Copake, NY 12516, 5 beds, 3 baths

$275,000

5 beds3 baths2,124 sq ft

2934 County Road 7, Copake, NY 12516

Property at 190 Egremont Plain Rd, Egremont, MA 01258, 1 bed, 1 bath

$885,000

1 bed1 bath1,377 sq ft

190 Egremont Plain Rd, Egremont, MA 01258

Property at 158 Knapp-carpenter Rd, Claverack, NY 12513, 3 beds, 1.5 baths

$695,000

3 beds1.5 baths1,542 sq ft

158 Knapp-carpenter Rd, Claverack, NY 12513

Property at 43 Main St, South Egremont, MA 01258, 5 beds, 3 baths

$699,000

5 beds3 baths4,127 sq ft

43 Main St, South Egremont, MA 01258

Property at 156 Farm Rd, Copake, NY 12516, 5 beds, 4 baths

$1,200,000

5 beds4 baths3,046 sq ft

156 Farm Rd, Copake, NY 12516

Listing by Corcoran Country Living

Property at 522 Roxbury Rd, Hudson, NY 12534, 3 beds, 1 bath

$575,000

3 beds1 bath1,336 sq ft

522 Roxbury Rd, Hudson, NY 12534

Property at 1643 County Route 7a, Copake, NY 12516, 4 beds, 1 bath

$524,900

4 beds1 bath1,758 sq ft

1643 County Route 7a, Copake, NY 12516

Property at 1492 County Route 7A, Copake, NY 12516, 3 beds, 2 baths

$585,000

3 beds2 baths2,064 sq ft

1492 County Route 7A, Copake, NY 12516

Listing by Corcoran Country Living

Property at 9 Prospect St, Philmont, NY 12565, 3 beds, 1 bath

$165,000

3 beds1 bath1,200 sq ft

9 Prospect St, Philmont, NY 12565

Property at 138 Hillsdale Rd, Egremont, MA 01258, 4 beds, 2.5 baths

$685,000

4 beds2.5 baths2,333 sq ft

138 Hillsdale Rd, Egremont, MA 01258

Property at 1781 New York 23, Craryville, NY 12521, 3 beds, 3 baths

$795,000

3 beds3 baths2,816 sq ft

1781 New York 23, Craryville, NY 12521

Property at 235 Birch Hill Rd, Copake, NY 12516, 3 beds, 1 bath

$389,000

3 beds1 bath1,080 sq ft

235 Birch Hill Rd, Copake, NY 12516

Listing by Helen Schweitzer Realty, LLC

Property at 7 Mellenville Sq, Claverack, NY 12534, 4 beds, 2 baths

$749,900

4 beds2 baths1,800 sq ft

7 Mellenville Sq, Claverack, NY 12534

Based on information submitted to the MLS GRID as of Sun Oct 04 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in 12529

There are currently 15 vintage homes for sale in 12529 at a median listing price of $712K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 12529 stay on the market for 126 days. This map is refreshed with the newest listings in 12529 every 15 minutes.

In the past month, 5 homes have been sold in 12529. In addition to houses in 12529, there were also 0 condos, 1 townhouse, and 4 multi-family units for sale in 12529 last month. Find your dream home in 12529 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 12529 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 12529. If you're looking to sell your home in the 12529 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 12529 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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