Orange County NY Homes under $500,000

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  /47

  $499,888

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft

  3 Pine Ln, Greenwood Lake, NY 10925

  This pristine contemporary Cape Cod home in Greenwood Lake offers the perfect blend of style, comfort, and location. Inside, you'll find an open-concept living space with soaring vaulted ceilings, gleaming hardwood floors, and a cozy pellet stove that adds warmth and charm. The spacious kitchen features granite countertops, ample cabinetry, and an inviting eat-in dining area. Set on a private

  Peter Kontrafouris eXp Realty

  3 Pine Ln, Greenwood Lake, NY 10925
• 

  

  

  /22

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft

  626 Union Ave, New Windsor, NY 12553

  All-brick 3-bedroom, 2-bath ranch on a half-acre corner lot in New Windsor. This home has a one-car garage, a wide driveway, and a huge backyard—plenty of space for entertaining, gardening, or just enjoying the outdoors. Inside, it offers a practical layout with good-sized rooms. Great location close to shops, schools, and major roads. Clean and well-kept, with room to make it your own.

  JOSE SANTOS K Fortuna Lighthouse Realty

  626 Union Ave, New Windsor, NY 12553
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  /28

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,666 Sq Ft

  101 Old Plank Rd, Sparrowbush, NY 12780

  Tucked away within the woods this effortlessly chic home has every nook and cute cranny you have been craving! Airy open kitchen design with white marble countertops with views of the serene garden and growing spaces. Outdoor living at its best! Plus ..just around the corner from the reservoir. The perfect blend of modern comfort and natural beauty..Solitude..soul nurturing lush gardening..

  Debbie Jagel Cabins & Canoes Real Estate

  101 Old Plank Rd, Sparrowbush, NY 12780
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  /12

  $425,000

  • 3 Beds
  • 1 Bath
  • 1,350 Sq Ft

  15 Queen St, New Windsor, NY 12553

  Check out this charming brick 3 bedroom 1 bath home in the Town of New Windsor. This home offers beautiful hardwood floors, stainless steel appliances, and a rear sun room for entertaining. This is a perfect home for any first time home buyer. Close to restaurants, shopping, and all major highways this is in a perfect location for any commuter. Come check it out!

  Tyler Prokosch John J Lease REALTORS Inc

  15 Queen St, New Windsor, NY 12553
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  /38

  $449,000

  • 4 Beds
  • 2 Baths
  • 2,140 Sq Ft

  31 Highland Ave, Otisville, NY 10963

  Step back in time with this beautifully preserved 1900 colonial, offering 4 bedrooms, 2 full baths, and 2,150 sq ft of timeless charm. Stunning natural woodwork, handcrafted details, and gorgeous period features fill the spacious living areas, including a large living room, formal dining room, and an eat-in kitchen complete with an original dumbwaiter and Butler’s staircase. Upstairs, the primary

  Karen McCabe Weichert Realtors

  31 Highland Ave, Otisville, NY 10963
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  /20

  $469,000

  • 4 Beds
  • 3 Baths
  • 3,555 Sq Ft

  711 Homestead Ave, Maybrook, NY 12543

  Historic 1780's home in the sweet village of Maybrook. Center entrance colonial with symmetrical, well proportioned rooms flanking the center staircase. Five fireplaces, very large den. Hardwood floors as seen. Long wood barn with two car garage (see photos)Two bedrooms en suite on second story with another quaint bedroom, and sewing room (easily converted to home office). Eat-in kitchen

  MaryBeth O'Hara Ellis Sotheby's Intl Realty

  711 Homestead Ave, Maybrook, NY 12543
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  /28

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  170 Clove Rd, Salisbury Mills, NY 12577

  Step into comfort and style! This bright, airy home features an inviting living room and a spacious dining area, perfect for entertaining. The gorgeous kitchen offers crisp white cabinetry, sleek granite countertops, and modern stainless steel appliances. Gleaming hardwood floors flow throughout the home. Outside, a huge front yard and a sprawling, level backyard provide endless space for

  Lazar Schvimmer Blooming Realty

  170 Clove Rd, Salisbury Mills, NY 12577
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  /25

  $410,000

  • 4 Beds
  • 2.5 Baths
  • 2,043 Sq Ft

  41 Liberty St, Newburgh, NY 12550

  Gorgeous, fully detached Victorian with 4 spacious bedrooms, 3 full bathrooms, and sun-drenched interiors, this home features oversized windows, gleaming hardwood floors, and a flowing layout perfect for living and entertaining. Charming front porch and private rear deck overlooking the yard.Finished attic offers a full bath, skylights, and flexible space—perfect for a home office, guest

  *DNC* Andres Santiago ReAttached

  41 Liberty St, Newburgh, NY 12550
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  /31

  $480,000

  • 3 Beds
  • 2 Baths
  • 1,898 Sq Ft

  45 Bible Camp Rd, Bloomingburg, NY 12721

  Welcome to this renovated split-level with a large barn located in the Pine Bush school district. This home PLUS large renovated barn is set just minutes from wine trails, orchards bursting with fruit, artisan breweries like Gardiner Brewing, and the magic of Sam's Point and the Ice Caves, this home is more than a place—it's a lifestyle. Fish in freshwater streams by day, catch a show at City

  Davina Thomasula Four Seasons Sotheby's Int'l-K

  45 Bible Camp Rd, Bloomingburg, NY 12721
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  /37

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 1,671 Sq Ft

  87 Barr Ln, Monroe, NY 10950

  Beautiful Townhouse Style Condo located in the sought after Meadow Glen of Monroe. This 3 bedroom condo offers 3 levels of living. Entry foyer leads to stairs to formal living room and gorgeous eat in kitchen with new stainless steel appliances , Master bedroom suite with private bath, 2 additional bedrooms , 1 car Garage, all town services and close to all major highways for commuting

  Kathleen Milich RE/MAX Benchmark Realty Group

  87 Barr Ln, Monroe, NY 10950
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  /23

  $499,900

  • 3 Beds
  • 1.5 Baths
  • 2,228 Sq Ft

  307 Route 17k, Newburgh, NY 12550

  Explore this 2228 sq ft colonial, featuring 3 beds and1.5 baths, poised for residential or commercial use pending zoning change. Ideal for professionals like doctors or attorneys seeking office space, or potential as a boutique or even a gas station given its prime corner location. Positioned in a thriving area, this property offers both immediate comfort and long-term investment potential.

  Don Maher BHHS Hudson Valley Properties

  307 Route 17k, Newburgh, NY 12550
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  /34

  $475,000

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  411 Liberty St, Newburgh, NY 12550

  AS IS - SELLER MOTIVATED Located in the Historic District, next to Mount Saint Mary College Campus. This end brick row house is attached on one side. Two separate porches to enter each floor thru apartment. Completely renovated, newly painted, new floors, new lighting and SS appliances. Open floor dining shared with living room. Backyard for use.Separate utilities, all

  Maria Ferguson 1st Independent Realty Grp

  411 Liberty St, Newburgh, NY 12550
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  /38

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  16 Birch Dr, Greenwood Lake, NY 10925

  Welcome to this beautifully updated 3-bedroom, 2-bath home offering comfort, style, and functionality in every corner. With high ceilings that create an open and airy feel, this home features modern updates throughout, providing a fresh and move-in ready space. The spacious living areas are perfect for entertaining or relaxing, and the thoughtfully designed layout ensures both privacy and

  Brandy Seltzer Century 21 Elite Realty

  16 Birch Dr, Greenwood Lake, NY 10925
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  /39

  $429,000

  • 3 Beds
  • 2.5 Baths
  • 1,614 Sq Ft

  10 Ironwood Dr, Highland Mills, NY 10930

  Welcome to this delightful and spacious townhouse in Timber Ridge. This two-story residence offers 3 bedrooms and 2.5 baths. It features numerous upgrades. The first floor includes a galley kitchen with granite countertops, a stylish backsplash, and organized drawers. You'll find new appliances such as a refrigerator, microwave, and dishwasher. Adjacent to the kitchen, there's a generous

  Jacob Katz Exit Realty Venture

  10 Ironwood Dr, Highland Mills, NY 10930
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  /3

  $425,000

  • 5 Beds
  • 2 Baths
  • 1,560 Sq Ft

  449 3rd St, Newburgh, NY 12550

  2-family house in City of Newburgh featuring a 3 bedroom upstairs and a 2 bedroom downstairs. With a full walkout basement. Huge driveway with a detached garage. Close to stores on Broadway

  Bryan Dale eXp Realty

  449 3rd St, Newburgh, NY 12550
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  /3

  $475,000

  • 4 Beds
  • 2 Baths
  • 2,844 Sq Ft

  10 Pleasant St, Florida, NY 10921

  Welcome to 10 Pleasant Street a spacious 4 bedroom, 2 bathroom home offering 2844 square feet of living space, situated on a generous .62-acre lot in the heart of the charming Village of Florida, NY. Located in the highly regarded Warwick Valley School District, this home combines small- town living with room to grow.Being sold as-is, this home is an excellent opportunity for buyers looking

  Marcus Soler Soler Realty

  10 Pleasant St, Florida, NY 10921
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  /33

  $499,000

  • 4 Beds
  • 2 Baths
  • 1,880 Sq Ft

  611 Twin Arch Rd, Rock Tavern, NY 12575

  Back on market! Brand new well pump and freshly painted kitchen. Welcome home to this lovingly-maintained 4 bedroom colonial home set on 1.3 acres. Spread out on the main floor, which offers a large country kitchen with an abundance of storage, main living room, plus 2 bonus rooms, full bath, and laundry, perfect for guests, extended family, with no-step living. Upstairs you'll find 4 bedrooms,

  Karen Klos Ellis Sotheby's Intl Realty

  611 Twin Arch Rd, Rock Tavern, NY 12575
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  /41

  $480,000

  • 4 Beds
  • 2.5 Baths
  • 2,848 Sq Ft

  4 Thistle Ln, Middletown, NY 10940

  Spacious & Versatile Raised Ranch in Prime Middletown Location!Not your average bi-level! This move-in-ready, raised-ranch-style home in Middletown, within the Minisink Valley School District, offers the perfect blend of convenience and comfort. Located near Garnet Medical Center, Crystal Run, shopping centers, supermarkets, and with easy access to Metro-North and major highways, it’s an

  Soleil Jackman Howard Hanna Rand Realty

  4 Thistle Ln, Middletown, NY 10940
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  /23

  $424,999

  • 5 Beds
  • 3 Baths
  • 2,400 Sq Ft

  17 Brooklyn St, Port Jervis, NY 12771

  Step into this stunning brand new home, where every detail has been thoughtfully designed from the ground up! Featuring 5 bedrooms and 3 full baths, this home boasts a brand new kitchen with modern cabinetry, sleek granite countertops and all new appliances. Every bathroom will be beautifully done, while new windows, a new roof, and all new mechanicals provide peace of mind for years to come.

  Gloria Rivera Keller Williams Hudson Valley

  17 Brooklyn St, Port Jervis, NY 12771
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  /19

  $450,000

  • 3 Beds
  • 3 Baths
  • 2,470 Sq Ft

  52 Lander St, Newburgh, NY 12550

  Welcome to 52 Lander St., Property offers a shared entrance with one apartment down stairs and one upstairs. Recently converted to a multi fam. Both units are newly renovated and fully occupied with great tenants. Owner currently does not allow tenants to smoke or to have pets inside the building. Each unit has s/s appliances, ceiling fans, multiple outlets ,1 full bath with shower. Rooms are

  Melissa Forsyth Hudson Valley Home Connection

  52 Lander St, Newburgh, NY 12550
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  /5

  $500,000

  • Land
  • 0.46 Acre
  • $1,086,957 per Acre

  23 Central Valley, Monroe, NY 10950

  Experience the ultimate in natural beauty on this expansive lot, spanning nearly half an acre, perfectly situated within the prestigious Woodbury Junction. With its prime location, this lot offers breathtaking panoramic views, providing a stunning backdrop for your future outdoor endeavors. Build your custom dream house on this incredible property, tailored to your every need and desire. Bring

  Joel Jeremias eRealty Advisors, Inc

  23 Central Valley, Monroe, NY 10950
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  /43

  $499,000

  • 2 Beds
  • 1 Bath
  • 1,596 Sq Ft

  140 Orrs Mills Rd, Salisbury Mills, NY 12577

  New Spring Price Adjustment - Very private, scenic, secluded location, with incredible endless views. Enjoy the peaceful, calmness, water and trestle views in rear of property. Massive, level front yard, oversized 2 car cement block garage. Lovingly cared for family residence boasting 2 bedrooms with an additional possible 3rd or use as office/den/guest, kitchen, living room, dining rm.,

  Maureen Wallace Smitchger Realty

  140 Orrs Mills Rd, Salisbury Mills, NY 12577
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  /26

  $420,000

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  241 Smith Clove Rd, Highland Mills, NY 10930

  What a view! Charming cottage style home located on 1.5 private acres is adjacent to open land and has splendid views of the surrounding mountains! Just an hour or so from New York City, this is a perfect spot for your weekend getaway. Or make it your new home! The house is in the Monroe Woodbury school district and includes the coveted Woodbury Recreation – the John Burke Memorial Pool, also the

  Karin Poggio HomeSmart Homes & Estates

  241 Smith Clove Rd, Highland Mills, NY 10930
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  /3

  $450,000

  • 8 Beds
  • 1 Bath
  • 4,741 Sq Ft

  56 Ball Rd, Warwick, NY 10990

  The Ball Farm Homestead represents the splendor of the 19th century in historic Warwick. Construction began during the Civil War and was finally completed in 1865. This four-story Grand Dame is waiting for the history lover that wants to restore her to her original magnificence. Features include original unpainted woodwork, marble fireplace surrounds, central halls with substantial hardwood

  Theresa Powers Keller Williams Realty

  56 Ball Rd, Warwick, NY 10990
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  /13

  $450,000

  • Land
  • 2.20 Acres
  • $204,545 per Acre

  6 Lookout Terrace, Chester, NY 10918

  Looking for just the right spot to build your dream home? Close to everything but also tucked away for peace and privacy. Spread out at the end of a cul de sac lies the land that can be the footprint for your new home. Make this your personal paradise or subdivide (7 lot potential) and sell as an investment. This 2.2 acre lot will be able to have municipal water and sewer. Conveniently located

  Gina Dudgeon Howard Hanna Rand Realty

  6 Lookout Terrace, Chester, NY 10918
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  /21

  $435,000

  • 3 Beds
  • 1.5 Baths
  • 1,984 Sq Ft

  325 Powell Ave, Newburgh, NY 12550

  Nestled in the heart of Newburgh, this charming 3-bedroom, 1.5-bathroom home offers both comfort and convenience in a prime location! Situated directly across from Mount Saint Mary College, this property provides easy access to schools, shopping, dining, and transportation. Key Features: • 3 Bedrooms: Spacious and bright rooms perfect for families or extra space for an office or hobby room. • 1.5

  Patrick Casilli John J Lease REALTORS Inc

  325 Powell Ave, Newburgh, NY 12550
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  /20

  $430,000

  • 2 Beds
  • 1.5 Baths
  • 1,497 Sq Ft

  47 Valley Ave, Walden, NY 12586

  Beautifully, recently renovated & refreshed, 6 room, 3 bedroom colonial bordering Tin Brook in the heart of the Village of Walden. Close to major shopping, Hannaford Supermarket, many parks, eateries,Stewart International Airport, Valley Central schools, I84 & I87 to commute. It has a gorgeous kitchen with plentiful white cabinetry, granite counters, high ceilings and recessed lights, stainless

  Marion Bruhns Howard Hanna Rand Realty

  47 Valley Ave, Walden, NY 12586
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  /4

  $500,000

  • Land
  • 8 Acres
  • $59,648 per Acre

  30 Harding Way, Chester, NY 10950

  Opportunity is knocking on the door for all builders/investors in the Town Of Chester, Monroe - Woodbury School District. You buy 2 lots for the price of one. 30 Harding Way is SOLD TOGETHER with the lot next to it of 8.2 acres which is located in Section 15, Block 1, Lot 32. Subdivision potential.

  Ida Payne Keller Williams Realty

  30 Harding Way, Chester, NY 10950
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  /29

  $499,000

  • 6 Beds
  • 4 Baths
  • 3,550 Sq Ft

  12 Brown St, Port Jervis, NY 12771

  Back on the Market July 2025. This one-of-a-kind Two-family home with a large finished separate basement, renovation completed this June. After receiving multiple as high as $550,000-this gem is now being offered at a reduced price of $499,000. Due to previous buyers being unable to secure financing, the owner is now seeking cash buyers or those with non-contingent mortgage offers only. Designed

  Katya Bruen Avenues Residential

  12 Brown St, Port Jervis, NY 12771
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  /22

  $475,000

  • 3 Beds
  • 1.5 Baths
  • 1,858 Sq Ft

  10 Cane Rd, Greenwood Lake, NY 10925

  Welcome to Greenwood Lake! Presenting the opportunity to own a cozy move-in ready raised ranch on a quiet road! This home has hardwood flooring under the carpeting and throughout, with a kitchen, a spacious living room, a full bathroom, and three bedrooms on the top level and a finished lower level with ample space for recreation and a bonus room that can be used as an office or additional fourth

  Nicholas Cuomo Keller Williams Realty

  10 Cane Rd, Greenwood Lake, NY 10925
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  /2

  $499,000

  • Land
  • 4.50 Acres
  • $110,889 per Acre

  1414 Kings Hwy, Chester, NY 10918

  5 Lot subdivision which has been engineered and submitted to Chester planning board for approvals with water and sewer. Not approved but in the process. Buyer must finish. Site plan in documents as well as addressed planning board comments. Additional Information: SoilType:Unknown,

  Joe Distelburger Keller Williams Realty

  1414 Kings Hwy, Chester, NY 10918
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  /2

  $500,000

  • Land
  • 4.00 Acres
  • $125,000 per Acre

  0 Fortune Rd E Unit KEYH6205613, Scotchtown, NY 10941

  Approved for 13000 SF of Office and or Day Care with water and sewer. Great location in the busy Town of Wallkill, near the Galleria Mall, Adams Supermarket, Hotels, Tractor Supply, Hannaford Shopping Center. Additional 17.7 Acres available, MLS 6205621. See documents for TC (Town Center) allowed uses. Site plan in docs Additional Information: SoilType:Unknown,

  Joe Distelburger Keller Williams Realty

  0 Fortune Rd E Unit KEYH6205613, Scotchtown, NY 10941
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  /2

  $500,000

  • Land
  • 0.83 Acre
  • $603,355 per Acre

  0 Main St, Chester, NY 10918

  Open commercial lot directly behind the existing Cumberland Farms and just to the east of the former Brookside carwash. Good use may be for a parking lot for a building built on 42 Brookside.

  Claude Brischoux Keller Williams Realty

  0 Main St, Chester, NY 10918
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  /5

  $450,000

  • Land
  • 2.90 Acres
  • $155,172 per Acre

  0 Airport Rd Unit ONEH6195533, Scotchtown, NY 10940

  Great zoning which allows any non residential use on this corner lot at the intersections of Airport Rd and Dolsontown Rds on the roundabout next to new Sunoco gas station and strip mall. See zoning in docs Additional Information: SoilType:Unknown,

  Joe Distelburger Keller Williams Realty

  0 Airport Rd Unit ONEH6195533, Scotchtown, NY 10940
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  /2

  $499,999

  • 3 Beds
  • 2.5 Baths
  • 2,186 Sq Ft

  9 Utopian Place, Walden, NY 12586

  Coming Soon to the market.

  Richard Baxter KELLER WILLIAMS REALTY

  9 Utopian Place, Walden, NY 12586
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  /2

  $410,000

  • 2 Beds
  • 1 Bath
  • 1,091 Sq Ft

  6 Stropkov Ct Unit 304, Monroe, NY 10950

  Prime Location! Located near schools, shopping centers, and business centers, yet on a quiet cul-de-sac! Enjoy the calmness and convenience of this home! This top second floor apartment features a large kitchen, dining room, and 2 spacious bedrooms. The outside features lots of space for kids' play and car parking.

  Jacob Katz Exit Realty Venture

  6 Stropkov Ct Unit 304, Monroe, NY 10950
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  /2

  $429,000

  • 5 Beds
  • 4 Baths
  • 2,600 Sq Ft

  1265 Us Highway 6, Port Jervis, NY 12771

  3-Family INVESTOR ALERT$$$ Investment Opportunity with Strong Cash Flow $$$This turnkey 3-Family is ready for you to start earning in the Minisink Valley School District! This well-maintained, 3-family investment property offers the perfect blend of affordability, income, and location. Whether you're a first-time homebuyer looking to live in one unit while the rental income helps pay your

  Jackie Siracuse Absolute Real Estate of NY Inc

  1265 Us Highway 6, Port Jervis, NY 12771
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  /2

  $449,000

  • 7 Beds
  • 3 Baths
  • 2,508 Sq Ft

  172 Chambers St, Newburgh, NY 12550

  Great Investment opportunity; the owner has done some of the heavy lifting already, the balance is there for you to customize as you see fit. Currently configured as 3 units, two 2 Bedroom units and one 3 Bedroom unit, located in the heart of Newburgh.

  Adam Kaplan Renaissance Realty Cons Group

  172 Chambers St, Newburgh, NY 12550
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  /2

  $425,000

  • 3 Beds
  • 3 Baths
  • 2,376 Sq Ft

  36 Edward St, Newburgh, NY 12550

  Enjoy the views of the Hudson River from this Townhouse Fixer Upper. Three apartments on a peaceful block close to other residential and commercial developments. This is a great value add opportunity. Views of the Hudson, need I say more? Great investment opportunity.

  Adam Kaplan Renaissance Realty Cons Group

  36 Edward St, Newburgh, NY 12550
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  /2

  $449,000

  • 5 Beds
  • 4 Baths
  • 3,986 Sq Ft

  205 Broadway, Newburgh, NY 12550

  The Fixer Upper you've been looking for, lots of upside, value add potential with this one. Plans in hand to convert from 4 units to 5. Located in the Broadway Corridor of historic Newburgh, this architectural gem is the ready for its new owner.

  Adam Kaplan Renaissance Realty Cons Group

  205 Broadway, Newburgh, NY 12550

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