Vintage homes for sale & real estate in 12529, NY

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ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
Colonial Home on a Beautiful Country Parcel with New Garage Nestled on a peaceful country road, this charming two-bedroom Colonial offers the perfect blend of privacy, comfort, and convenience. Set back from the road on a beautiful parcel, the home welcomes you into a bright, open-concept living and dining area filled with natural light and complemented by attractive hardwood floors. The galley-style kitchen features stainless steel appliances, making meal preparation and entertaining effortless. Enjoy dinner in the adjoining dining area, relax in the inviting three-season sunroom, or step outside to the spacious rear deck to soak in the surrounding countryside. The first floor also offers

$392,500

2 beds2 baths1,494 sq ft

Laundry area • New garage • Full bathroom

155 Pumpkin Hollow Rd N, Hillsdale, NY 12529

Listing by Elyse Harney Real Estate

NEW 23 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
95 - 97 Main St: Prime Investment Opportunity in the Heart of Philmont is An exceptional opportunity to acquire a fully leased, mixed-use building. * This two-story building consists of approximately 5,800 Square feet. * There are a total of four units. * There are two fully leased commercial storefronts at street level and two three-bedroom apartments above. * The property also features a large lot with ample off street parking for both the commercial and residential needs. Highlight: Fully leased portfolio Strong, diversified income stream Mixed-use property in a central Main Street location Attractive investment with long-term growth potential Ideal for investors seeking stable ca

$535,000

6 beds4 baths5,800 sq ft

Stable cash flow • Large lot • 0.27 acre lot

95-97 Main St, Philmont, NY 12565

NEW 22 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
100 - 102 Main St: Prime Investment Opportunity in the Heart of Philmont is An exceptional opportunity to acquire a fully leased, mixed-use building. * This two-story building consists of approximately 4,400 Square feet. * There are a total of five units. * There are two fully leased commercial storefronts at street level and two one-bedroom apartments and one two-bedroom apartment above. Highlight: Fully leased portfolio Strong, diversified income stream Mixed-use property in a central Main Street location. Attractive investment with long-term growth potential. Ideal for investors seeking stable cash flow in a desirable small-town commercial corridor.

$525,000

4 beds5 baths4,400 sq ft

Mixed-use property • 2,613 sq ft lot • Built 1910

100-102 Main St, Philmont, NY 12565

ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
Are you dreaming of times spent tucked away in a rustic cabin, preferably wrapped in a cozy blanket in front of a roaring fireplace? Or maybe you're dreaming of barefoot in the stream that feds into the Green River and sunbathing with rays of sunshine beaming through the trees? Welcome to 251 Overlook, Hillsdale NY! Cira 1900 Cottage in the woods, built on the side of a mountain, on 4.5 Acres. A wood lover's dream. Some features include one bedroom, one bath, eat-in kitchen with classic refrigerator, knotty pine walls, 2-story fieldstone fireplace with enamel stove w/ thermal glass doors, a fully lined chimney, cathedral ceiling with exposed beams and a sleeping loft overlooking it all. L

$365,000

1 bed1 bath684 sq ft

Knotty pine walls • Eat-in kitchen • Cathedral ceiling

251 Overlook Dr, Hillsdale, NY 12529

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

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

152 Main St, Philmont, NY 12565

Listing by Houlihan Lawrence Inc

Property at 81 SW Colony Rd, Hillsdale, NY 12529, 2 beds, 1 bath

$325,000

2 beds1 bath736 sq ft

81 SW Colony Rd, Hillsdale, NY 12529

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

$649,000

3 beds2 baths1,475 sq ft

81 Black Grocery Rd, Hillsdale, NY 12529

Listing by Houlihan Lawrence, Inc

Property at 44 SW Colony Rd, Copake, NY 12529, 3 beds, 1.5 baths

$859,000

3 beds1.5 baths1,293 sq ft

44 SW Colony Rd, Copake, NY 12529

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

$949,900

3 beds2 baths1,600 sq ft

2955 State Route 23, Hillsdale, NY 12529

Listing by Coldwell Banker Advisor Realty

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

$3,600,000

5 beds5.5 baths5,083 sq ft

335 Dawson Rd, Hillsdale, NY 12529

Listing by Brown Harris Stevens HV LLC

Property at 9659 Ny-22, Hillsdale, NY 12529, 3 beds, 1 bath

$339,900

3 beds1 bath1,381 sq ft

9659 Ny-22, Hillsdale, NY 12529

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 16 Elm St, Philmont, NY 12565, 3 beds, 2.5 baths

$110,000

3 beds2.5 baths1,480 sq ft

16 Elm St, Philmont, NY 12565

Listing by Gilcrest Properties

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

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 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

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NEW 24 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
This 3-bedroom, 1 bath row house in the village of Philmont has been updated with new windows, modernized electrical systems, and a substantial amount of plaster and lathe replaced with sheetrock. The home includes a 3-season porch, offering a great space to enjoy the outdoors most of the year, and a small outdoor space with a work or storage shed. Located just minutes from both Hudson and Chatham, the house provides easy access to shopping, dining, and local attractions.

$165,000

3 beds1 bath1,200 sq ft

Work or storage shed • Outdoor space • New windows

9 Prospect St, Philmont, NY 12565

ABOUT THIS HOME
Vintage Home for sale in 12529, MA:
Set on over 2 acres in beautiful Egremont, this lovingly maintained four-bedroom, 2½-bath home blends classic character with thoughtful updates and additions made over the years. Built in 1920's, the house retains the warmth and craftsmanship of its era, including charming built-ins and inviting spaces that make it feel truly like home. A large deck provides the perfect setting for morning coffee, summer gatherings, or simply taking in the peaceful surroundings and lovely seasonal views. The property offers plenty of room to garden, explore, and enjoy the outdoors. A barn and chicken coop add to its country appeal. A detached garage with a large workshop provides excellent space for

$685,000

4 beds2.5 baths2,333 sq ft

Large deck • Barn • Over 2 acres

138 Hillsdale Rd, Egremont, MA 01258

ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
A truly distinctive Hudson Valley property, 1781 State Route 23 pairs a charming 1930 Arts and Crafts-style parsonage with the fully historic former Craryville United Methodist Church. Both buildings have been renovated with new kitchens, baths and heating and cooling. The parsonage residence offers approximately 1,458 square feet, split into two 1 bedroom apartments. While the separate church building features roughly 1,358 square feet, soaring ceilings, a full bath, a full kitchen, and a lower-level work and shop space. Set on approximately . 8 acre between Hudson and Great Barrington, this one-of-a-kind property presents exciting possibilities for residential, creative, commercial, live

$795,000

3 beds3 baths2,816 sq ft

New kitchens • Full kitchen • New baths

1781 New York 23, Craryville, NY 12521

ABOUT THIS HOME
Vintage Home for sale in 12529, MA:
Perched high on Baldwin Hill! Set far back from the road on a beautiful 2.5-acre lot, this thoughtfully updated South Egremont residence offers a rare balance of scenic tranquility and unbeatable convenience. Positioned to capture sweeping mountain views, the property places you seconds from charming Egremont village, minutes from vibrant downtown Great Barrington, and right down the road from Prospect Lake and French Park. The owners have completed major updates so you can simply arrive and unpack. Recent improvements bring fresh energy throughout the home, including brand-new siding, new windows that flood the spaces with natural light, and a refreshed kitchen featuring new flooring and b

$599,000

3 beds2 baths1,649 sq ft

2.5-acre lot • New siding • New flooring

18 Baldwin Hill Rd, Egremont, MA 01230

ABOUT THIS HOME
Vintage Home for sale in 12529, MA:
Originally built in the 19th century, this Egremont schoolhouse has undergone a radical, ''down-to-the-studs'' transformation, and has been thoughtfully designed to create a high-performance home for modern living, while honoring its historic character. Sound structural integrity, with state of the art insulation, custom engineered windows, a new HVAC system, and a solar array for near zero energy overhead make this home immensely comfortable and sustainable for decades to come. The Great Room features dramatic vaulted ceilings anchored by original exposed beams and a new, high-efficiency propane free standing stove. The chef's kitchen has custom cabinetry topped with honed marble counters.

$885,000

1 bed1 bath1,377 sq ft

Solar array • New hvac system • 0.5 acre lot

190 Egremont Plain Rd, Egremont, MA 01258

ABOUT THIS HOME
Vintage Home for sale in 12529, NY:
Welcome to your dream country escape! This charming, fully renovated Cape Cod home has been meticulously rebuilt down to the studs, offering brand-new modern finishes while preserving its classic character. Step inside to discover a bright, airy open floor plan designed for effortless entertaining and comfortable daily living. Owner in process of finishes which will include, electric fireplace, front porch and new kitchen. Still time to pick cabinetry colors for kitchen once under contract. Situated just a 2-hour drive via the Taconic State Parkway, this property is the ideal second home or weekend retreat. Enjoy the tranquility of Columbia County with the ultimate convenience: you are with

$389,000

3 beds1 bath1,080 sq ft

Fully renovated • New kitchen • Front porch

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

$799,900

4 beds2 baths1,800 sq ft

7 Mellenville Sq, Claverack, NY 12534

Property at 210 Bate Rd, Claverack, NY 12521, 2 beds, 2 baths

$995,000

2 beds2 baths2,400 sq ft

210 Bate Rd, Claverack, NY 12521

Listing by Four Seasons Sothebys Intl

Property at 797 State Route 203, Spencertown, NY 12165, 3 beds, 2 baths

$479,900

3 beds2 baths1,430 sq ft

797 State Route 203, Spencertown, NY 12165

Property at 192 County Route 7a, Copake, NY 12516, 3 beds, 1 bath

$175,000

3 beds1 bath1,280 sq ft

192 County Route 7a, Copake, NY 12516

Property at 204 George Rd, Ghent, NY 12075, 5 beds, 3 baths

$849,000

5 beds3 baths3,815 sq ft

204 George Rd, Ghent, NY 12075

Property at 3493 County Road 7, Hillsdale, NY 12529, 3 beds, 2.5 baths

$650,000

3 beds2.5 baths1,977 sq ft

3493 County Road 7, Hillsdale, NY 12529

Listing by Corcoran Country Living

Property at 3493 County Route 7, Hillsdale, NY 12529, 3 beds, 2.5 baths

$650,000

3 beds2.5 baths1,977 sq ft

3493 County Route 7, Hillsdale, NY 12529

Listing by Corcoran Country Living

Property at 52 Church St, Hudson, NY 12534, 5 beds

$495,000

5 beds— baths1,872 sq ft

52 Church St, Hudson, NY 12534

Property at 48 Konig Rd, Ghent, NY 12075, 4 beds, 3 baths

$1,475,000

4 beds3 baths2,204 sq ft

48 Konig Rd, Ghent, NY 12075

Listing by Gabel Real Estate

Property at 39 Pine Crest Cross Rd, Egremont, MA 01230, 2 beds, 3 baths

$2,400,000

2 beds3 baths2,616 sq ft

39 Pine Crest Cross Rd, Egremont, MA 01230

Property at 1953 County Road 11, Claverack, NY 12513, 4 beds, 1 bath

$389,000

4 beds1 bath2,229 sq ft

1953 County Road 11, Claverack, NY 12513

Listing by Davala Real Estate LLC

Property at 1100 Harlemville Rd, Ghent, NY 12075, 3 beds, 2 baths

$1,300,000

3 beds2 baths1,858 sq ft

1100 Harlemville Rd, Ghent, NY 12075

Listing by Rouse + Co Real Estate

Property at 286 Manor Rock Rd, Craryville, NY 12521, 3 beds, 2 baths

$939,000

3 beds2 baths1,393 sq ft

286 Manor Rock Rd, Craryville, NY 12521

Listing by Houlihan Lawrence, Inc

Property at 171 Orchard Rd, Ghent, NY 12075

$599,000

Land56.00 acres (lot)

171 Orchard Rd, Ghent, NY 12075

Listing by B & L Property Group LLC

Based on information submitted to the MLS GRID as of Wed Aug 19 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 17 vintage homes for sale in 12529 at a median listing price of $770K. 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 84 days. This map is refreshed with the newest listings in 12529 every 15 minutes.

In the past month, 4 homes have been sold in 12529. In addition to houses in 12529, there were also 0 condos, 0 townhouses, and 3 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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