Homes for Sale in Columbia County NY with 5-Bedrooms

• 

  

  

  /57

  $575,000

  • 5 Beds
  • 3 Baths
  • 3,200 Sq Ft

  105 McNamee Rd, Canaan, NY 12029

  Extensively renovated in 2024, this exceptional year-round Queechy Lake retreat offers a rare combination of lifestyle, privacy, and income potential with a very active summer and winter activities in the lake or on the ice! Spanning three finished levels, the property features a total of 5 bedrooms and 2 full bathrooms. Thoughtful renovations throughout deliver a truly move-in-ready home with

  

  Joseph Cardinale

  Howard Hanna Capital, Inc.

  (518) 768-9819

  105 McNamee Rd, Canaan, NY 12029
• 

  

  

  /32

  $3,885,000

  • 5 Beds
  • 6 Baths
  • 6,062 Sq Ft

  420 Warren St, Hudson, NY 12534

  Public Remarks: Built in 1887 in the Aesthetic Movement Style, this red brick building commands the center of Warren Street in the heart of Hudson. The exterior features extensive ornamental terra-cotta panels and trim. The historic interior retains elaborate wood beam ceilings with richly paneled rooms, oak and cherry fireplace mantles and intricate parquet floors. Originally the private

  

  Paul Barrett

  Houlihan Lawrence, Inc

  (518) 800-2717

  420 Warren St, Hudson, NY 12534
• 

  

  

  /37

  $3,995,000

  • 6 Beds
  • 5 Baths
  • 12,000 Sq Ft

  147 Rock City Rd, Old Chatham, NY 12136

  A rare offering of scale, privacy, and refinement, Bellavista Country Estate is a magnificent 12,000-square-foot Georgian brick residence set on over 25 secluded acres in the foothills of the Berkshires, perfectly positioned between the Hudson River Valley and the Berkshires. Designed for elegant country living at the highest level, the estate offers six to nine beautifully appointed bedrooms,

  

  Joseph Briggs

  William Pitt Sotheby's

  (518) 741-3264

  147 Rock City Rd, Old Chatham, NY 12136
• 

  

  

  /23

  $665,000

  • 7 Beds
  • 5 Baths

  80 County Route 7, Pine Plains, NY 12567

  This beautifully updated legal 2-family home seamlessly blends vintage charm with modern convenience, offering exceptional flexibility for multigenerational living, rental income, or guest accommodations. Located just 7 minutes from Pine Plains Village and set on a scenic lot with sweeping countryside views and a neighboring 200-acre farm, the property features meticulously maintained grounds,

  

  Margaret Mondello

  Margaret Mondello Real Estate

  (518) 608-3993

  80 County Route 7, Pine Plains, NY 12567
• 

  

  

  /32

  $3,995,000

  • 5 Beds
  • 4.5 Baths
  • 6,518 Sq Ft

  167 New Concord Rd, East Chatham, NY 12060

  Perched High on a Hill, A Modern Sanctuary of Timeless Elegance. Set atop 74 acres of extraordinary privacy in the historic hamlet of New Concord, this refined center hall colonial commands sweeping views of rolling meadows, wooded trails, hay fields, and distant Catskill horizons. Bathed in sunlight throughout the day, the property offers a rare sense of peace and expansiveness, where nature,

  

  Joseph Briggs

  William Pitt Sothebys Intn'l

  (518) 735-6773

  167 New Concord Rd, East Chatham, NY 12060
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  /44

  $2,650,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,000 Sq Ft

  5988 New York 9h, Hudson, NY 12534

  Set way back from the road is this spacious, 5-Bedroom, 4.5 Bath Contemporary farmhouse which embodies timeless craftsmanship and country charm. This carefully curated home is a blend of natural stone, hand-hewn repurposed Hemlock timber beams, honey colored wide board Pine flooring, fine finishes and efficient systems throughout. Inside the front door lies a Great Room with a 25' high cathedral

  

  Paul Barrett

  Houlihan Lawrence Inc.

  (518) 634-9174

  5988 New York 9h, Hudson, NY 12534
• 

  

  /39

  $599,000

  • 8 Beds
  • 4 Baths
  • 3,864 Sq Ft

  3122 High St, Valatie, NY 12184

  Turnkey four-unit investment opportunity in the Village of Valatie offering stable in-place income with clear upside potential. This solid brick building has been meticulously maintained by the same owners for over 30 years and is fully occupied with long-term, reliable tenants, providing immediate cash flow and operational stability.The property consists of four spacious two-bedroom units,

  Dina Coluccio Monticello

  3122 High St, Valatie, NY 12184
• 

  

  /27

  $330,000

  • 7 Beds
  • 2 Baths
  • 2,668 Sq Ft

  35 Church St, Philmont, NY 12565

  Opportunity meets flexibility at this beautifully updated duplex in the Village of Philmont. Whether you're looking to offset your ownership expenses or expand your investment portfolio, this property offers both comfort and potential in one inviting package.Apartment 1 is currently rented, providing immediate income, while Apartment 2 is vacant and in the final stages of a thoughtful tenant

  Heather Davala Davala Real Estate, LLC

  35 Church St, Philmont, NY 12565
• 

  

  /34

  $319,900

  • 6 Beds
  • 3 Baths
  • 2,962 Sq Ft

  53 Main St, Philmont, NY 12565

  Versatile Multi-Family Opportunity in the Heart of Philmont Discover the potential of this spacious and character-filled property, ideal for investors or owner-occupants alike. Currently configured as a two-family home, this residence also offers the flexibility to be converted back into a single-family home to suit your needs. Boasting over 3,000 square feet of living space, this impressive

  Jason Walch Coldwell Banker Advisor Realty

  53 Main St, Philmont, NY 12565
• 

  

  /36

  $965,000

  • 6 Beds
  • 3 Baths
  • 2,797 Sq Ft

  379 County Route 28b, Valatie, NY 12184

  Welcome to this beautifully Restored 1870s Farmhouse. This expansive 6 bedroom, 3 bathroom home seamlessly blends historic charm with modern comfort. Set on nearly three serene acres in Valatie, the home offers privacy, space, and timeless appeal. Professionally designed by local interior design, build and restoration company, preserving it's original character details such as wide-plank hardwood

  Erin Shepherd Mahar Real Estate, LLC

  379 County Route 28b, Valatie, NY 12184
• 

  

  /16

  $1,295,000

  • 8 Beds
  • 4 Baths
  • 5,635 Sq Ft

  358 Warren St, Hudson, NY 12534

  A mixed use building in the heart of historic Hudson. This c1860 Federal style brick building is a fabulous investment with four beautifully updated apartments. Gut renovated in 2021, the building is completely turn key and has retained much of its historic charm. You'll find a studio garden apartment in the lower level, a 2BR apartment on street level which could also be used as

  Annabel Taylor Four Seasons Sotheby's Int.

  358 Warren St, Hudson, NY 12534
• 

  

  /65

  $2,585,000

  • 5 Beds
  • 6 Baths
  • 3,600 Sq Ft

  282 Ridge Rd, Schodack Landing, NY 12156

  Welcome to your 112 acre dream home/farm. The main house, built 2024, has 3 bedrooms, 2.5 baths and a wonderful front porch. Open concept living room - kitchen with large center island. 30' x 60' Morton barn/garage. The secondary home (Cape Cod) has 2 bedrooms, 2.5 baths built in 2023. Great for guest house, in-law or rental. The fully insulated 42' x 124' equine Morton barn has 16 stalls,

  Karen Westman Berkshire Hathaway HomeService

  282 Ridge Rd, Schodack Landing, NY 12156
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  /49

  $819,000

  • 5 Beds
  • 3.5 Baths
  • 2,622 Sq Ft

  823 Warren St, Hudson, NY 12534

  Exceptional opportunity to own a fully vacant, three-unit multi-family property in the heart of Hudson's vibrant Warren Street. This charming building offers a unique blend of investment potential and personal use, with a proven track record as a successful short-term rental and owner use property. Featuring three distinct units, this property is ideal for investors, or live in owners. Prime

  Austin Urban Venture Fox Realty Group LLC

  823 Warren St, Hudson, NY 12534
• 

  

  /20

  $420,000

  • 6 Beds
  • 4 Baths
  • 3,945 Sq Ft

  7 Ellsworth St, Philmont, NY 12565

  Well-maintained 4-unit multifamily property located at 7-9 Ellsworth St in the heart of Philmont. This solid investment opportunity features three 1 bedroom, 1 bath apartments and one spacious 3 bedroom, 1 bath unit. Each apartment offers in-unit washer and dryer hookups, providing added convenience for tenants.Three of the four units are currently rented with active leases in place, while

  Heather Davala Davala Real Estate, LLC

  7 Ellsworth St, Philmont, NY 12565
• 

  

  /12

  $408,451

  • 8 Beds
  • 4 Baths
  • 2,700 Sq Ft

  7 S 7th St, Hudson, NY 12534

  Located just blocks from Hudson's Warren Street corridor, the Amtrak station, and the waterfront, the property offers strong long-term potential for redevelopment into multi-unit housing, live/work space, or other residential configurations subject to City approvals and located in the historical district. This 4 unit building is being offered as a full gut renovation project for experienced

  Elizabeth Hendler Berkshire Hathaway HomeService

  7 S 7th St, Hudson, NY 12534
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  /53

  $680,000

  • 9 Beds
  • 9 Baths
  • 6,935 Sq Ft

  1121 New York 295, East Chatham, NY 12060

  2-Story/5-Apartment/9BR/6BA building PLUS 2BR/1BA Ranch home on about a half acre. Fully occupied, leases, both structures fully up to date and move-in condition. Tenants pay all utils. Landlord provides maintenance, snow/trash removal, water/sewer, off-street parking, fridge/stove each unit. 2 SBL lot numbers - properties not sold separately. Assessment/tax figures herein reflect total due for

  Natalia de Amorim Preferred Country Properties

  1121 New York 295, East Chatham, NY 12060
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  /37

  $689,365

  • 5 Beds
  • 3.5 Baths
  • 2,964 Sq Ft

  118 Old Shaker Rd, New Lebanon, NY 12125

  Historic eyebrow colonial with deep Shaker heritage. Stunning views, privacy, mature flowering trees, mountain and valley views, gazebo, all add to the special qualities of this one of a kind property. Built in the 1800's this gem boasts a quaint country kitchen, butcher block counters, original wood floors, views out every window. 3.5 baths, 5 bedrooms, oversize 2 car garage with work space.

  Sharon McArdle Berkshire Hathaway Home Services Blake

  118 Old Shaker Rd, New Lebanon, NY 12125
• 

  

  /65

  $1,395,000

  • 5 Beds
  • 4 Baths
  • 3,640 Sq Ft

  83 Silvernail Rd, Valatie, NY 12184

  Tucked away at the end of a quiet dead-end road in the glorious countryside of Chatham, this exceptional property offers privacy, history, and sweeping natural beauty. The circa 1840's five-bedroom farmhouse combines timeless character with comfortable living, featuring a first floor primary en suite, an inviting library, and a warm living room with a fireplace. The charming hobby room and

  Linnea VanTassel Country Life Real Estate, LLC

  83 Silvernail Rd, Valatie, NY 12184
• 

  

  /30

  $440,000

  • 8 Beds
  • 4 Baths
  • 2,840 Sq Ft

  142 Main St, Hudson, NY 12534

  142 Main Street, Philmont, NY 12565 Fully Rented 4-Unit Investment Opportunity Turn-key multi-family property in the heart of Philmont featuring four fully rented units with strong rental income and diverse layouts. Ideal for investors seeking immediate cash flow in a centrally located village setting. This building offers: Unit 1 (1st Floor): 2 Bedrooms, 1 Bath Approx. 800 sq ft. Unit 2 (2nd

  Heather Davala Davala Real Estate, LLC

  142 Main St, Hudson, NY 12534
• 

  

  /39

  $375,000

  • 5 Beds
  • 2 Baths
  • 2,500 Sq Ft

  60 Prospect St, Philmont, NY 12565

  In the heart of Philmont, this two-family home offers steady investment value alongside original details that maintain character and charm of its era. The lower level offers 3 bedrooms and 1 bath with generous living space, while the upper unit features 2 bedrooms and 1 bath--each enjoying abundant natural light and its own outdoor patio. Both apartments are separately metered, making management

  Paige Paluch William Raveis Real Estate

  60 Prospect St, Philmont, NY 12565
• 

  

  /21

  $1,750,000

  • 9 Beds
  • 6 Baths
  • 4,104 Sq Ft

  208 Warren St, Hudson, NY 12534

  For investors seeking ease of ownership and reliable returns, 208 Warren Street offers a fully gut-renovated six-unit building in Hudson's walkable core. The property has been completely updated with all brand-new systems and clean, modern apartments featuring updated kitchens and baths, premium appliances, split-unit heat and A/C, and preserved architectural details where possible. A strong fit

  Zev Eisenberg Hudson Modern

  208 Warren St, Hudson, NY 12534
• 

  

  /17

  $650,000

  • 6 Beds
  • 4 Baths
  • 3,193 Sq Ft

  233 Columbia St, Hudson, NY 12534

  Just moments from the energy and culture of Warren Street, this fully occupied four unit property offers both immediate income and long-term potential in the heart of Hudson. Each unit is currently month to month tenant occupied, creating a seamless turnkey opportunity for investors seeking stable cash flow in one of the Hudson Valley's most sought-after markets. Set within walking distance to

  Carrie Dandridge Find Advisors

  233 Columbia St, Hudson, NY 12534
• 

  

  /28

  $810,000

  • 6 Beds
  • 2 Baths
  • 2,998 Sq Ft

  60 Anthony St, Hillsdale, NY 12529

  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 min ride to

  Gerard Meenagh The Meenagh Group Realty

  60 Anthony St, Hillsdale, NY 12529
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  /51

  $2,895,000

  • 7 Beds
  • 4 Baths
  • 5,188 Sq Ft

  311 County Route 13, Old Chatham, NY 12136

  Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers

  Nikki Carchedi Stone House Properties, LLC

  311 County Route 13, Old Chatham, NY 12136
• 

  

  /48

  $2,895,000

  • 7 Beds
  • 4 Baths
  • 5,188 Sq Ft

  311 County Road 13, Old Chatham, NY 12136

  Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers

  Nikki Carchedi STONE HOUSE PROPERTIES, LLC

  311 County Road 13, Old Chatham, NY 12136
• 

  

  /44

  $6,950,000

  • 5 Beds
  • 4.5 Baths
  • 6,438 Sq Ft

  890 Bald Mountain Rd, Austerlitz, NY 12017

  Welcome to Bald Mountain Estate, an extraordinary private compound spanning 85 breathtaking acres overlooking the Hudson Valley and the Berkshire Hills. This four-building, ultra-contemporary estate epitomizes modern country luxury, featuring floor-to-ceiling glass walls and a steel infrastructure that creates a distinctive blend of rusticelegance and architectural sophistication.The

  Lisa Bouchard Hoe The Kinderhook Group, Inc.

  890 Bald Mountain Rd, Austerlitz, NY 12017
• 

  

  /85

  $3,250,000

  • 5 Beds
  • 5 Baths
  • 3,703 Sq Ft

  33 Broad St, Kinderhook, NY 12106

  Down a long maple-lined driveway, an early Kinderhook home and newer guest house has been given a new life as a 7BR/7BA private estate with many options for indoor and outdoor entertainment on almost nine acres. The main home, with over 3700 square feet of living space, boasts five beds and five baths, formal and informal dining areas, and a lower level rathskeller complete with a 250+ bottle

  Jennifer Wall Anderson Agency

  33 Broad St, Kinderhook, NY 12106
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  /35

  $375,000

  • 6 Beds
  • 2.5 Baths
  • 1,302 Sq Ft

  248 Maple Ln, Valatie, NY 12184

  This spacious home offers 6 bedrooms and 2.5 bathrooms, providing flexible living options for today's needs. The former attached garage has been thoughtfully converted into an in-law apartment, ideal for extended family, guests, or additional living space. A detached one-car garage adds convenience and extra storage. Conveniently located with easy access to local amenities, this property offers

  Sonny Patel Empire Real Estate Firm LLC

  248 Maple Ln, Valatie, NY 12184
• 

  

  /58

  $475,000

  • 5 Beds
  • 5 Baths
  • 3,296 Sq Ft

  5562 New York 9g, Hudson, NY 12534

  This income-producing multi-unit property spans a combined 4.8 acres across two parcels, located just minutes from Hudson and Germantown. The offering includes a 2-acre parcel with an existing multi-unit structure along with an adjacent 2.8-acre parcel, providing additional land, privacy, and a natural setting. The structure contains multiple residential units currently in use, with four units

  Jesse Chason Compass Greater New York, LLC

  5562 New York 9g, Hudson, NY 12534
• 

  

  /63

  $1,950,000

  • 19 Beds
  • 7 Baths
  • 6,192 Sq Ft

  514 State St, Hudson, NY 12534

  Fully Renovated Apartment House with six three-bedroom apartments and one one-bedroom unit. The three-bedroom units have one larger bedroom with two smaller bedrooms or offices. The one-bedroom apartment in the basement level, which is above grade in the rear. The renovated barn, in the rear of the building is currently rented as art studio space, brings the total rentable units to eight. Classic

  Victor Mendolia The Kinderhook Group, Inc.

  514 State St, Hudson, NY 12534
• 

  

  /90

  $1,450,000

  • 7 Beds
  • 5.5 Baths
  • 6,005 Sq Ft

  126 Shaker Ridge Dr, Canaan, NY 12029

  Welcome to Cannondale Compound. Set on 20 private acres with far-reaching mountain views, this 7,300-square-foot architectural retreat is ideally suited for large gatherings. Designed with soaring modernist lines and exceptional craftsmanship, the home offers multiple living and dining areas, seven bedrooms across two connected wings, expansive porches and balconies, and both indoor and outdoor

  Anthony D'Argenzio Houlihan Lawrence Inc.

  126 Shaker Ridge Dr, Canaan, NY 12029
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  /68

  $4,200,000

  • 5 Beds
  • 6 Baths
  • 7,974 Sq Ft

  520 Ridge Rd, Schodack Landing, NY 12156

  A private outdoor paradise perfect for recreation, agriculture, equestrian or hunting. This 9,565 sqft home has all one could ask for. Offering spacious living areas, hardwood floors, custom media room perfect for movie nights, sizable bedrooms, finished walk-out basement, there's ample space for both family and guests to gather and unwind. With spa/hot tub room, gym, a 2,400 sq. ft. heated

  Tyler Bervy Stone House Properties, LLC

  520 Ridge Rd, Schodack Landing, NY 12156
• 

  

  /50

  $749,900

  • 5 Beds
  • 2 Baths
  • 2,106 Sq Ft

  16 Aitken Ave, Hudson, NY 12534

  Charming 1940s Arts and Crafts Home - Completely Renovated! Welcome to your dream home nestled in the heart of Hudson! This stunning 1940s Arts and Crafts style residence has been meticulously restored, blending timeless charm with modern conveniences. Step inside to find gleaming hardwood floors that create a warm and inviting atmosphere throughout. The brand new kitchen is a chef's delight,

  Jahorul Liton Red Apple Realty

  16 Aitken Ave, Hudson, NY 12534
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  /51

  $2,750,000

  • 6 Beds
  • 5 Baths
  • 6,000 Sq Ft

  356 Slate Hill Rd, Chatham, NY 12037

  A rare opportunity to own a masterfully reimagined circa-1861 post-and-beam barn, transformedinto a one-of-a-kind luxury estate set on 89 pristine acres in the heart of Columbia County. Surrounded by sweeping pastoral views, open fields, and tranquil natural beauty, this exceptional property offers privacy, scale, and timeless craftsmanship. The residence spans approximately 6,000 square feet

  Anne Harrison Country Life Real Estate, LLC

  356 Slate Hill Rd, Chatham, NY 12037
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  /38

  $1,699,900

  • 16 Beds
  • 13 Baths
  • 8,476 Sq Ft

  94 Main St, Philmont, NY 12565

  Prime Investment Opportunity in the Heart of Philmont An exceptional opportunity to acquire a fully leased, mixed-use portfolio. This offering includes three buildings located at 94 Main Street, 95-97 Main Street, and 100-102 Main Street, all generating stable income with upside potential for future growth. Property Breakdown: 94 Main StreetA two-story, approximately 4,800 SF, three-unit

  Jason Walch Coldwell Banker Advisor Realty

  94 Main St, Philmont, NY 12565
• 

  

  /49

  $775,000

  • 8 Beds
  • 8 Baths
  • 6,915 Sq Ft

  163 County Route 14, Hudson, NY 12534

  Rare offering! Versatile multi-unit property. Perfect for investors seeking strong rental income and long-term growth. The main building features five spacious one-bedroom units, each offering a generous layout and excellent rental income potential. Also included is a charming and spacious single-family home featuring three bedrooms and one and a half baths, making this an ideal owner-occupant

  Nicole Polito Coldwell Banker Village Green

  163 County Route 14, Hudson, NY 12534
• 

  

  /13

  $219,000

  • 7 Beds
  • 3 Baths
  • 1,530 Sq Ft

  14598 New York 22 Unit 1, New Lebanon, NY 12125

  Nice investment property in this two family home. Live in one side and rent out the other, or rent out both sides. One apartment is presently rented. There is a garage. Large back yard. House needs some upgrades. Walking distance to downtown New Lebanon. Right in the heart of town. Minutes to the Berkshires and skiing, close to TSP, I-90, Thruway, Albany, Hudson.

  Leonard Brown Berkshire Hathaway HomeService

  14598 New York 22 Unit 1, New Lebanon, NY 12125
• 

  

  /35

  $799,000

  • 6 Beds
  • 2 Baths
  • 2,416 Sq Ft

  843 Union St, Hudson, NY 12534

  Immaculate, income-producing townhouse, plus a separate lot with a barn on Hudson's Union Street...now available! Walkable to everything Hudson offers, this two-family residence is in excellent condition and ready for your further refinements. The upstairs unit is unoccupied and freshly renovated, featuring hardwood floors throughout and a deck in back. The downstairs unit is in similar condition

  Andrew Edwards Tri Hudson Realty, LLC

  843 Union St, Hudson, NY 12534
• 

  

  /39

  $5,950,000

  • 5 Beds
  • 4.5 Baths
  • 6,438 Sq Ft

  890 Bald Mountain Rd, Austerlitz, NY 12017

  Welcome to Bald Mountain Estate, an extraordinary private compound spanning 85 breathtaking acres overlooking the Hudson Valley and the Berkshire Hills. This four-building, ultra-contemporary estate epitomizes modern country luxury, featuring floor-to-ceiling glass walls and a steel infrastructure that creates a distinctive blend of rustic elegance and architectural sophistication. The

  Janet Kain The Kinderhook Group, Inc.

  890 Bald Mountain Rd, Austerlitz, NY 12017
• 

  

  /29

  $189,000

  • 5 Beds
  • 1 Bath
  • 2,236 Sq Ft

  31 Albany Turnpike, Old Chatham, NY 12136

  Fantastic colonial fixer upper with 5-bedrooms and one bath located in Chatham School District. Plenty of room for everyone. Light & bright kitchen with fir floors. Bedroom on first floor. Big back yard. Ready to make it your own.

  Anne Harrison Country Life Real Estate, LLC

  31 Albany Turnpike, Old Chatham, NY 12136

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