239 properties for sale in South Highland, Philipstown town Putnam County New York

24 Leisure Way
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Condo · for sale
USD 499,000
USD 376/sq.ft
24 Leisure Way
South Highland, Philipstown town Putnam County New York
· 1,324 sq.ft · 2 Bedrooms · 2 Baths · Condo
South Highland, Philipstown town Putnam County New York · 1,324 sq.ft · 2 Bedrooms · 2 Baths · Condo
Welcome Home to this quintessential lakeside Community where nature greets you at your doorstep! This much sought after townhouse styled condominium sited in Villas on the Lake is truly the BEST place to live. Minutes to the Taconic State Parkway and 3 miles from Metro North makes this a commuter's DREAM! Sited on Mohegan Lake this condo offers an unparalleled lifestyle of recreation, nature, convenience and affordability! Curb appeal exudes from the moment you walk upon the meandering sidewalk. This end unit offers privacy as well as additional windows to allow so much light to stream in. Also the cross breezes in the home are idea for ventilation. Enter into your foyer where you can keep your shoes, coat rack and umbrellas. There is a nice sized storage which extends under the staircase. Perfect for suitcases for your next vacation, sporting goods, hobby storage or excess furniture. Exceptional living room with solid oak build-ins that can store your collections, decorations, and tra
Welcome Home to this quintessential lakeside Community where nature greets you at your doorstep! This much sought after townhouse styled condominium sited in Villas on the Lake is truly the BEST place to live. Minutes to the Taconic State Parkway and 3 miles from Metro North makes this a commuter's DREAM! Sited on Mohegan Lake this condo offers an unparalleled lifestyle of recreation, nature, convenience and affordability! Curb appeal exudes from the moment you walk upon the meandering sidewalk. This end unit offers privacy as well as additional windows to allow so much light to stream in. Also the cross breezes in the home are idea for ventilation. Enter into your foyer where you can keep your shoes, coat rack and umbrellas. There is a nice sized storage which extends under the staircase. Perfect for suitcases for your next vacation, sporting goods, hobby storage or excess furniture. Exceptional living room with solid oak build-ins that can store your collections, decorations, and tra
USD 499,000
65 Lake Drive
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House · for sale
USD 625,000
USD 496/sq.ft
65 Lake Drive
South Highland, Philipstown town Putnam County New York
· 1,259 sq.ft · 2 Bedrooms · 2 Baths · House
· Fireplace
South Highland, Philipstown town Putnam County New York · 1,259 sq.ft · 2 Bedrooms · 2 Baths · House · Fireplace
Direct Lakefront Ranch – Lake Peekskill, NY Discover an exceptional direct lakefront retreat in the heart of Lake Peekskill. Designed for effortless entertaining and relaxed waterfront living, this charming ranch delivers panoramic lake and mountain views that change beautifully with every season. Step outside to your private waterfront oasis featuring a spacious dock, gazebo, and tiki hut. Swim, fish, canoe, or kayak right from your own shoreline, or simply unwind with outdoor dining while taking in spectacular sunrises and sunsets. It’s an ideal setup for hosting family and friends or enjoying quiet days by the water. Inside, the home offers remodeled flooring, a cozy fireplace, and stunning lake views from the dining area, creating a warm, inviting atmosphere. Additional highlights include abundant storage and above-ground oil heat for comfortable year-round living. A rare, one-of-a-kind opportunity to own a true private waterfront escape where every day feels like a vacation
Direct Lakefront Ranch – Lake Peekskill, NY Discover an exceptional direct lakefront retreat in the heart of Lake Peekskill. Designed for effortless entertaining and relaxed waterfront living, this charming ranch delivers panoramic lake and mountain views that change beautifully with every season. Step outside to your private waterfront oasis featuring a spacious dock, gazebo, and tiki hut. Swim, fish, canoe, or kayak right from your own shoreline, or simply unwind with outdoor dining while taking in spectacular sunrises and sunsets. It’s an ideal setup for hosting family and friends or enjoying quiet days by the water. Inside, the home offers remodeled flooring, a cozy fireplace, and stunning lake views from the dining area, creating a warm, inviting atmosphere. Additional highlights include abundant storage and above-ground oil heat for comfortable year-round living. A rare, one-of-a-kind opportunity to own a true private waterfront escape where every day feels like a vacation
USD 625,000
26 Winhaven Court
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Condo · for sale
USD 450,000
USD 220/sq.ft
26 Winhaven Court
South Highland, Philipstown town Putnam County New York
· 2,045 sq.ft · 2 Bedrooms · 2 Baths · Condo
· Office room · Deck · Cellar
South Highland, Philipstown town Putnam County New York · 2,045 sq.ft · 2 Bedrooms · 2 Baths · Condo · Office room · Deck · Cellar
Welcome to this beautifully maintained 2-bedroom, 2.5-bath townhouse style condominium offering approximately 2,000 square feet of comfortable living space in the intimate Winhaven Park Condominiums, a community of approximately 20 residences. The main level features a spacious open floor plan designed for easy everyday living and entertaining. A bright and inviting den filled with natural light provides flexible space for a home office, sitting room, or reading area. The living room features sliding glass doors leading to the deck, creating a seamless connection to the outdoors. Upstairs, you'll find two generously sized bedrooms, including a spacious primary suite with its own private en-suite full bathroom. An additional full bathroom and conveniently located second-floor washer and dryer complete this level. Pull-down attic access provides even more storage space. The finished walk-out basement adds valuable additional living space with a comfortable family room featuring a Murphy
Welcome to this beautifully maintained 2-bedroom, 2.5-bath townhouse style condominium offering approximately 2,000 square feet of comfortable living space in the intimate Winhaven Park Condominiums, a community of approximately 20 residences. The main level features a spacious open floor plan designed for easy everyday living and entertaining. A bright and inviting den filled with natural light provides flexible space for a home office, sitting room, or reading area. The living room features sliding glass doors leading to the deck, creating a seamless connection to the outdoors. Upstairs, you'll find two generously sized bedrooms, including a spacious primary suite with its own private en-suite full bathroom. An additional full bathroom and conveniently located second-floor washer and dryer complete this level. Pull-down attic access provides even more storage space. The finished walk-out basement adds valuable additional living space with a comfortable family room featuring a Murphy
USD 450,000
17 Winhaven Court 8
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Condo · for sale
USD 430,000
USD 208/sq.ft
17 Winhaven Court 8
South Highland, Philipstown town Putnam County New York
· 2,067 sq.ft · 2 Bedrooms · 2 Baths · Condo
· Office room · Gym · Parking · Air conditioning · Swimming pool · Cellar
South Highland, Philipstown town Putnam County New York · 2,067 sq.ft · 2 Bedrooms · 2 Baths · Condo · Office room · Gym · Parking · Air conditioning · Swimming pool · Cellar
Welcome home to this beautifully maintained 2-bedroom, 2.5-bath townhome nestled in one of Highland Falls' most peaceful and private communities. Offering three finished levels, including a walkout basement and attached garage, this spacious home provides the perfect blend of comfort, nature, and convenience. The bright and inviting floor plan features generous living spaces, while the primary suite boasts stunning vaulted ceilings that create an airy, relaxing retreat. The finished walkout basement offers flexible space for a family room, home office, gym, or guest area. With hardwood floors, updated central air and water heater, there's little left to do but move in. Surrounded by a quiet, wooded setting, you'll enjoy exceptional privacy while being just minutes from everything that makes the Hudson Valley special. Located near Bear Mountain State Park, you'll have easy access to miles of scenic hiking trails, the Bear Mountain skating rink, swimming pool, picnic areas, and year-roun
Welcome home to this beautifully maintained 2-bedroom, 2.5-bath townhome nestled in one of Highland Falls' most peaceful and private communities. Offering three finished levels, including a walkout basement and attached garage, this spacious home provides the perfect blend of comfort, nature, and convenience. The bright and inviting floor plan features generous living spaces, while the primary suite boasts stunning vaulted ceilings that create an airy, relaxing retreat. The finished walkout basement offers flexible space for a family room, home office, gym, or guest area. With hardwood floors, updated central air and water heater, there's little left to do but move in. Surrounded by a quiet, wooded setting, you'll enjoy exceptional privacy while being just minutes from everything that makes the Hudson Valley special. Located near Bear Mountain State Park, you'll have easy access to miles of scenic hiking trails, the Bear Mountain skating rink, swimming pool, picnic areas, and year-roun
USD 430,000
26 Fishkill Road
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House · for sale
USD 650,000
USD 365/sq.ft
26 Fishkill Road
South Highland, Philipstown town Putnam County New York
· 1,776 sq.ft · 3 Bedrooms · 3 Baths · House
· Garden · Fireplace · Parking
South Highland, Philipstown town Putnam County New York · 1,776 sq.ft · 3 Bedrooms · 3 Baths · House · Garden · Fireplace · Parking
Experience the charm of a historic Greek Revival farmhouse beautifully updated for modern living. This 1,776 sq ft, 3-bedroom, 3-bath home blends original 19th-century character with today’s comfort and efficiency. Wide-plank wood floors, a full-length columned front porch, and period architectural details create an inviting sense of history from the moment you arrive. Inside, the living room centers around a fireplace with a wood-burning stove, perfect for cozy Hudson Valley evenings. The home is equipped with a heat pump for efficient heating and cooling, plus solar panels and a Tesla Powerwall battery system, offering exceptional energy savings and peace of mind. A detached 2-car garage provides ample storage and workspace. The large front yard offers room to relax, garden, or entertain, all just minutes from the Village of Cold Spring, known for its charming shops, restaurants, and Metro-North station for an easy NYC commute. A rare opportunity to own a historic home with modern su
Experience the charm of a historic Greek Revival farmhouse beautifully updated for modern living. This 1,776 sq ft, 3-bedroom, 3-bath home blends original 19th-century character with today’s comfort and efficiency. Wide-plank wood floors, a full-length columned front porch, and period architectural details create an inviting sense of history from the moment you arrive. Inside, the living room centers around a fireplace with a wood-burning stove, perfect for cozy Hudson Valley evenings. The home is equipped with a heat pump for efficient heating and cooling, plus solar panels and a Tesla Powerwall battery system, offering exceptional energy savings and peace of mind. A detached 2-car garage provides ample storage and workspace. The large front yard offers room to relax, garden, or entertain, all just minutes from the Village of Cold Spring, known for its charming shops, restaurants, and Metro-North station for an easy NYC commute. A rare opportunity to own a historic home with modern su
USD 650,000
20 Division Street
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House · for sale
USD 950,000
USD 477/sq.ft
20 Division Street
South Highland, Philipstown town Putnam County New York
· 1,991 sq.ft · 4 Bedrooms · 2 Baths · House
· Equipped kitchen
South Highland, Philipstown town Putnam County New York · 1,991 sq.ft · 4 Bedrooms · 2 Baths · House · Equipped kitchen
Historic character meets a complete modern transformation at 20 Division Street in the heart of Cold Spring Village. Originally built in 1790, this four-bedroom, two-and-a-half-bathroom home has been thoughtfully reimagined from the inside out, offering 2,000+ square feet of beautifully finished living space. The fully renovated interior features an open, light-filled floor plan designed for both everyday living and entertaining. A brand-new kitchen anchors the main level, complemented by new hardwood floors, custom built-ins, exposed beamed ceilings, and carefully considered architectural details throughout. A newly added powder room completes the first floor. Upstairs, the hall bathroom has been completely updated, while the transformed primary suite features a new private full bathroom. Every space feels fresh, refined, and entirely move-in ready while preserving the character of the home’s historic origins. Outside, updated siding, a newer roof, and new paver work create an invitin
Historic character meets a complete modern transformation at 20 Division Street in the heart of Cold Spring Village. Originally built in 1790, this four-bedroom, two-and-a-half-bathroom home has been thoughtfully reimagined from the inside out, offering 2,000+ square feet of beautifully finished living space. The fully renovated interior features an open, light-filled floor plan designed for both everyday living and entertaining. A brand-new kitchen anchors the main level, complemented by new hardwood floors, custom built-ins, exposed beamed ceilings, and carefully considered architectural details throughout. A newly added powder room completes the first floor. Upstairs, the hall bathroom has been completely updated, while the transformed primary suite features a new private full bathroom. Every space feels fresh, refined, and entirely move-in ready while preserving the character of the home’s historic origins. Outside, updated siding, a newer roof, and new paver work create an invitin
USD 950,000
Amazon Rd
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House · for sale
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New
Amazon Rd
South Highland, Philipstown town Putnam County New York
· 1,109 sq.ft · 2 Baths · House
South Highland, Philipstown town Putnam County New York · 1,109 sq.ft · 2 Baths · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Rolling Way
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House · for sale
USD 293,500
USD 203/sq.ft
Updated
Rolling Way
South Highland, Philipstown town Putnam County New York
· 1,442 sq.ft · 3 Bedrooms · 2 Baths · House
South Highland, Philipstown town Putnam County New York · 1,442 sq.ft · 3 Bedrooms · 2 Baths · House
This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted
This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted
USD 293,500
Parkway Pl
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House · for sale
Request Details
Updated
Parkway Pl
South Highland, Philipstown town Putnam County New York
· 1,421 sq.ft · 3 Bedrooms · 1 Bath · House
South Highland, Philipstown town Putnam County New York · 1,421 sq.ft · 3 Bedrooms · 1 Bath · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Union Rd
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House · for sale
Request Details
Updated
Union Rd
South Highland, Philipstown town Putnam County New York
· 4 Bedrooms · 2 Baths · House
South Highland, Philipstown town Putnam County New York · 4 Bedrooms · 2 Baths · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Mill Ct
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House · for sale
Request Details
Updated
Mill Ct
South Highland, Philipstown town Putnam County New York
· House
South Highland, Philipstown town Putnam County New York · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Mill Court
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House · for sale
Request Details
Updated
Mill Court
South Highland, Philipstown town Putnam County New York
· House
South Highland, Philipstown town Putnam County New York · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Mill Ct # A
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House · for sale
Request Details
Updated
Mill Ct # A
South Highland, Philipstown town Putnam County New York
· House
South Highland, Philipstown town Putnam County New York · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Main St
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House · for sale
Request Details
Updated
Main St
South Highland, Philipstown town Putnam County New York
· 2,411 sq.ft · 4 Bedrooms · 2 Baths · House
South Highland, Philipstown town Putnam County New York · 2,411 sq.ft · 4 Bedrooms · 2 Baths · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Todt Hl
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House · for sale
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Updated
Todt Hl
South Highland, Philipstown town Putnam County New York
· 2,013 sq.ft · 2 Bedrooms · 2 Baths · House
South Highland, Philipstown town Putnam County New York · 2,013 sq.ft · 2 Bedrooms · 2 Baths · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Fishkill Rd
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House · for sale
Request Details
Updated
Fishkill Rd
South Highland, Philipstown town Putnam County New York
· 4 Bedrooms · 2 Baths · House
South Highland, Philipstown town Putnam County New York · 4 Bedrooms · 2 Baths · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Sagamore Ave
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House · for sale
Request Details
Updated
Sagamore Ave
South Highland, Philipstown town Putnam County New York
· 1,496 sq.ft · 3 Bedrooms · 2 Baths · House
South Highland, Philipstown town Putnam County New York · 1,496 sq.ft · 3 Bedrooms · 2 Baths · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Harrison Ave
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House · for sale
Request Details
Updated
Harrison Ave
South Highland, Philipstown town Putnam County New York
· House
South Highland, Philipstown town Putnam County New York · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Winston Ln
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House · for sale
Request Details
Updated
Winston Ln
South Highland, Philipstown town Putnam County New York
· 1,367 sq.ft · 3 Bedrooms · 2 Baths · House
South Highland, Philipstown town Putnam County New York · 1,367 sq.ft · 3 Bedrooms · 2 Baths · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Maple Ter
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House · for sale
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Updated
Maple Ter
South Highland, Philipstown town Putnam County New York
· 2,314 sq.ft · 3 Bedrooms · 2 Baths · House
South Highland, Philipstown town Putnam County New York · 2,314 sq.ft · 3 Bedrooms · 2 Baths · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Kimble Ave
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House · for sale
Request Details
Updated
Kimble Ave
South Highland, Philipstown town Putnam County New York
· 2,110 sq.ft · 3 Bedrooms · 2 Baths · House
South Highland, Philipstown town Putnam County New York · 2,110 sq.ft · 3 Bedrooms · 2 Baths · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Sagamore Ave
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House · for sale
Request Details
Updated
Sagamore Ave
South Highland, Philipstown town Putnam County New York
· 829 sq.ft · 1 Bath · House
South Highland, Philipstown town Putnam County New York · 829 sq.ft · 1 Bath · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Narraganset Rd
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House · for sale
Request Details
Updated
Narraganset Rd
South Highland, Philipstown town Putnam County New York
· 1,453 sq.ft · 3 Bedrooms · 2 Baths · House
South Highland, Philipstown town Putnam County New York · 1,453 sq.ft · 3 Bedrooms · 2 Baths · House
This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted
This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted
Request Details
Liberty St
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House · for sale
Request Details
Updated
Liberty St
South Highland, Philipstown town Putnam County New York
· House
South Highland, Philipstown town Putnam County New York · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details
Garfield St
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House · for sale
Request Details
Updated
Garfield St
South Highland, Philipstown town Putnam County New York
· House
South Highland, Philipstown town Putnam County New York · House
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank
Request Details

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