Orange County NY Homes under $500,000

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  /21

  $325,000

  • 2 Beds
  • 2 Baths
  • 1,029 Sq Ft

  1103 Washington Green, New Windsor, NY 12553

  This First Floor Unit in Washington Green is a rare find. It is one of the few with an oversized storage closet in unit off living room + a concrete walkway from the back patio stretching around to the parking lot, leaving almost no stairs. This End-unit living space backs up to the woods for complete privacy + tranquility, where you can enjoy your own gardening space and lawn. The Washington

  Lauren Racanelli RE/MAX Benchmark Realty Group

  1103 Washington Green, New Windsor, NY 12553
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  /2

  $350,000

  • Land
  • 41,817 Sq Ft
  • $364,583 per Acre

  21 Cerone Place, Newburgh, NY 12550

  .94 acres, vacant lot, RH Zoning -Residential High Density. Development parcel, to be combined with 31 Cerone Pl (adjacent 12,200 sq/ft Office on 1.5 acres). which provides flexibility for additional parking, new construction, or future redevelopment (see attached plans), making this a rare assemblage opportunity in the City of Newburgh Owners prefer to sell together with the adjacent 31 Cerone

  Charles Emanuel Rand Commercial

  21 Cerone Place, Newburgh, NY 12550
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  /26

  $289,999

  $30K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,112 Sq Ft

  18 Dubois St, Port Jervis, NY 12771

  Charming Bungalow in a Fantastic Port Jervis Neighborhood!Absolutely adorable bungalow-style home located in a desirable residential area of Port Jervis. This inviting property features beautiful hardwood flooring throughout, a formal dining room, three comfortable bedrooms, and a spacious full bathroom. The walk-up attic offers partially finished space—perfect for a playroom, home office, or

  Christian Zube Realty Executives Exceptional

  18 Dubois St, Port Jervis, NY 12771
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  /26

  $479,900

  • 2 Beds
  • 2.5 Baths
  • 1,762 Sq Ft

  15 High Ridge Ln, Middletown, NY 10940

  Welcome to this impeccably maintained center-unit townhouse in the desirable Fairways at Wallkill, a gated community known for its convenience and low-maintenance lifestyle. This two-bedroom, two-full bath and one-half bath home offers a clean, modern interior with nothing to update. The main level features an open layout with gleaming hardwood floors, neutral tones, and abundant natural light

  Patricia Sassi RE/MAX Benchmark Realty Group

  15 High Ridge Ln, Middletown, NY 10940
• 

  

  

  /19

  $455,000

  • 3 Beds
  • 1 Bath
  • 1,646 Sq Ft

  42 Waterstone Rd, Greenwood Lake, NY 10925

  Welcome to this charming 3-bedroom, 1-bath ranch, perfectly positioned in one of Greenwood Lake’s most desirable locations. Just a short stroll to the lake and the vibrant village center, you’ll enjoy effortless access to local shops, dining, parks, and everyday conveniences—all while tucked away in a peaceful residential setting. This home offers the ideal balance of tranquility and

  Lynn Palmieri Keller Williams Realty

  42 Waterstone Rd, Greenwood Lake, NY 10925
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  /31

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,512 Sq Ft

  21 Maine Dr, Newburgh, NY 12550

  Welcome home to the highly sought-after subdivision of Wedgewood Park in the Town of Newburgh. Set on an oversized lot with a fully fenced-in yard, this updated ranch offers a solid layout, modern upgrades, and fresh interior paint throughout. A tile entryway opens into bright, well-appointed living spaces with an easy, functional flow, including a dedicated dining room ideal for gatherings and

  Michael Rostanzo Tactical Realty LLC

  21 Maine Dr, Newburgh, NY 12550
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  /17

  $299,999

  $35K PRICE DROP Pre-Foreclosure

  • 4 Beds
  • 1.5 Baths
  • 1,706 Sq Ft

  3 Emerald Trail, Monroe, NY 10950

  Unique property offering space, flexibility, and privacy in quiet Mountain Lodge Park setting. One of the standout features is the oversized detached garage with a large open loft space above. Possibilities are endless providing excellent potential for a workshop, studio, hobby space, extensive storage, or even additional living space for multi-generational living. The main home offers a spacious

  Michelle Getty HVG Realty, Inc.

  3 Emerald Trail, Monroe, NY 10950
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  /2

  $350,000

  • Land
  • 2 Acres
  • $175,000 per Acre

  220 Oxford Rd, Chester, NY 10918

  A rare opportunity in Blooming Grove! This beautiful and flat 2-acre property offers endless potential in a calm and peaceful setting with a road frontage. Conveniently located just minutes from Prospect Garden, the land sits within the Monroe-Woodbury School District. With easy access to permits, this property is ideal for building your dream home or future investment. The neighborhood holds

  Chaim Weiss MS Realty Group USA, Inc

  220 Oxford Rd, Chester, NY 10918
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  /6

  $380,000

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,432 Sq Ft

  20 Redwood Dr, Highland Mills, NY 10930

  Looking for the perfect starter or downsizer? This 2 Bedroom, 1.5 Bathroom Townhouse end unit in Village of Woodbury might be for you! Close to I-87 shopping, schools and amenities.

  Ernie Acampora River Realty Services, Inc.

  20 Redwood Dr, Highland Mills, NY 10930
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  /32

  $269,900

  • 4 Beds
  • 2 Baths
  • 1,876 Sq Ft

  47 Ulster Ave, Walden, NY 12586

  Opportunity, space, and potential all come together at 47 Ulster Ave in the heart of Walden. This large village home offers a flexible layout with endless possibilities for the next owner, including an ideal setup for a potential mother daughter living situation. The property features 2 kitchens shown on tax record, 2 electric meters, and a layout that reflects its previous multifamily-style use,

  Jason Madison eXp Realty

  47 Ulster Ave, Walden, NY 12586
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  /45

  $479,900

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft

  38 Emperor Ln, Montgomery, NY 12549

  Set at the end of a cul-de-sac on a level one-acre lot, this 3-bedroom, 2-bath ranch offers 1,744 square feet of living space with a layout designed for easy everyday living. Hardwood floors run throughout the main living areas, while multiple updated windows bring in consistent natural light. Buyers searching for a ranch with a sunroom, full unfinished basement, and large outdoor space in Orange

  Virginia Corbett eXp Realty

  38 Emperor Ln, Montgomery, NY 12549
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  /36

  $439,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,436 Sq Ft

  21 Stonecrest Dr, New Windsor, NY 12553

  Welcome to 21 Stonecrest Drive in the heart of New Windsor — a well-maintained and inviting 3-bedroom, 1 full bathroom home offering 1,436 square feet of comfortable living space. Featuring beautiful hardwood floors throughout the main level, this home offers warmth and character along with a practical layout perfect for everyday living. Enjoy the convenience of a one-car attached garage, a large

  Steve Moreau Tactical Realty LLC

  21 Stonecrest Dr, New Windsor, NY 12553
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  /14

  $315,000

  $30K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,762 Sq Ft

  104 Oak St, Walden, NY 12586

  Welcome to 104 Oak St. A charming 3 Bedroom 1 Bath home situated in the heart of the Village of Walden, giving an outstanding blend of comfort and convenience. This home is an excellent house to call home or as an investment venture, boasting granite countertops, gleaming hardwood floors and bright airy rooms. Recent updates include new rear deck and stairs, new baseboard heat and water heater,

  Joseph Critelli Keller Williams Realty

  104 Oak St, Walden, NY 12586
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  /39

  $424,999

  • 3 Beds
  • 1 Bath
  • 1,499 Sq Ft

  53 Bible Camp Rd, Bloomingburg, NY 12721

  Discover the perfect blend of modern sophistication and serene country living in this beautifully updated, 1,499-square-foot single-family retreat. Nestled on an expansive 4.8-acre lot, this property offers a rare combination of ultimate privacy and effortless convenience within the vibrant Orange and Sullivan County region.From the moment you step inside there is a seamless flow through the

  Leidy Placido Howard Hanna Rand Realty

  53 Bible Camp Rd, Bloomingburg, NY 12721
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  /24

  $475,000

  • 7 Beds
  • 3 Baths
  • 3,336 Sq Ft

  95 Renwick St, Newburgh, NY 12550

  MULTI-FAMILY - NEWBURGH - INCOME PROPERTY or live in one and rent the other...Just off Liberty Street and walking distance to the main drag of the area...George Washington's Historic Headquarters, shops, restaurants and Newburgh's cosmopolitan waterfront. Just a short walk to The Bluff of the Heights for priceless views of the Hudson River to West Point and Mount Beacon...Large 3336' sq. ft.

  George Koudounas RE/MAX Benchmark Realty Group

  95 Renwick St, Newburgh, NY 12550
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  /50

  $459,900

  $10K PRICE INCREASE

  • 3 Beds
  • 1 Bath
  • 1,548 Sq Ft

  101 Highland Rd, Monroe, NY 10950

  Nestled away in the sought-after Sapphire Lake community, this charming home offers the perfect blend of peaceful lake living and exceptional convenience — ideally located just minutes from the Village of Harriman, major commuter routes, shopping, dining and Metro North service, while still enjoying the beauty and tranquility of a private lake neighborhood. Some photos have been virtually staged

  Susan Hamilton Keller Williams Realty

  101 Highland Rd, Monroe, NY 10950
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  /16

  $320,000

  $61K PRICE INCREASE

  • 4 Beds
  • 1 Bath
  • 1,764 Sq Ft

  19 East Ave, Walden, NY 12586

  12/15/2025 As per the bank appraiser bottom line for this property 304K. Sometimes I feel like I live it the twilight zone. Motivated seller Estate Sale. Priced right Come see this charming home centrally located in the Heart of Walden. Close to shopping and public transportation. This would be a great starter home. Seller is motivated. Hurry the will not last.

  Arduino Colomban Skyler Realty LLC

  19 East Ave, Walden, NY 12586
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  /6

  $500,000

  • Land
  • 9.6 Acres
  • $52,083 per Acre

  0 S Plank Rd Unit KEY880159, Wawayanda, NY 10973

  Access the property with appointments only!!!!!Approved 2 lots. Paradise found within 75 min from NYC. A rare opportunity to acquire beautiful lots and ready to build your dream home. It has a Gently rolling meadows fronting on a scenic pond in the indigot creek make this as an unique property with a small lake(BigPond).The small lake (or big pond) is fed by estuaries and hence won't be dry even

  Libin Baby Howard Hanna Rand Realty

  0 S Plank Rd Unit KEY880159, Wawayanda, NY 10973
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  /24

  $329,610

  $11K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 800 Sq Ft

  197 Wheeler Rd Unit 92 and 93, Florida, NY 10921

  ***Limited-Time Summer Starts Here Incentive available for buyers in contract by June 15. $10,000 off the purchase price, plus no site licensing fee for 12 months. See sales team for details.*** Mountain Cottages at Serenity Ridge Mountain Club may not be used as a primary residence and are intended only as second homes within a seasonal resort community. Serenity Ridge Mountain Club is Your Home

  Vanessa Wight BHG Real Estate Green Team

  197 Wheeler Rd Unit 92 and 93, Florida, NY 10921
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  /17

  $339,990

  • 2 Beds
  • 2.5 Baths
  • 1,241 Sq Ft

  5 Kendal Ln, Middletown, NY 10940

  Modern Comfort & Lake Access – The Best of Waters Edge! Welcome to this beautifully maintained 2-bedroom, 2.5-bath condo in the highly desirable Waters Edge community. Offering a perfect blend of peaceful lakeside living and modern convenience, this home is designed for those who appreciate a bright, open, and "easy-living" floor plan. Home Highlights: Bright & Airy Main Level: Enjoy a spacious

  Jonathon Lee Keller Williams Hudson Valley

  5 Kendal Ln, Middletown, NY 10940
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  /33

  $275,000

  $24K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,071 Sq Ft

  20 Pierces Rd Unit 36, Newburgh, NY 12550

  Welcome to where space, style, and location come together in a way that is increasingly hard to find in today’s market. This exceptionally oversized garden style condo offers a layout that immediately stands out. From the moment you enter, you are greeted with a bright, open flow that feels more like a home than a typical condo. The living and dining areas are expansive, giving you the

  Anesha Nesbitt eXp Realty

  20 Pierces Rd Unit 36, Newburgh, NY 12550
• 

  

  /40

  $480,000

  Open Sat 11AM - 1PM Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,350 Sq Ft

  5 Oak Ridge Dr, New Windsor, NY 12553

  Welcome to 5 Oak Ridge Drive in New Windsor! This well-maintained ranch-style home offers the convenience of single-level living with 3 bedrooms, 1.5 bathrooms, and an attached garage with an automatic electric door opener. Recent improvements include a new central air conditioning system and an upgraded electrical system, providing comfort and peace of mind for years to come. The functional

  Pete Wolven Hudson Valley Home Connection

  5 Oak Ridge Dr, New Windsor, NY 12553
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  /31

  $375,000

  • 3 Beds
  • 1 Bath
  • 1,420 Sq Ft

  34 Linden Dr, Newburgh, NY 12550

  Welcome to Colden Park! This charming 3 bedroom ranch is being offered on the market for the first time, after being in the same family since it was built. Situated on a corner lot towards the back of Colden Park, this ranch style home offers the ease and convenience of one level living, with a functional layout full of potential. Partially finished basement with permitted rec room, and a 1-car

  Gary MacEntee Keller Williams Realty

  34 Linden Dr, Newburgh, NY 12550
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  /3

  $350,000

  • Land
  • 1.42 Acres
  • $245,752 per Acre

  65 James P Kelly Way, Middletown, NY 10940

  Great location for a business. C-3 Zoning allows for any business, commercial or residential mix use. 262 feet frontage. Annual Average Daily Traffic (AADT) for 2023 is 10,569. There was a pre-approved building plan for a doctor's office building. The land is in the city of Middletown. The city will provide water and sewer. C-3 allow for 6 story mix-use business and residential building with the

  Jonathon Lee Keller Williams Hudson Valley

  65 James P Kelly Way, Middletown, NY 10940
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  /5

  $280,000

  • 7 Beds
  • 2 Baths
  • 1,740 Sq Ft

  201 W Parmenter St, Newburgh, NY 12550

  Spacious 2 Family. Great for a investor or owner occupancy. Upstairs has4 Bedrooms, kitchen, living room and full bath. Downstairs has 3 Bedrooms, kitchen, living room and full bath. All separate utilities (electric and gas), hardwoods throughout. Fenced in yard.

  Adam Kaplan

  201 W Parmenter St, Newburgh, NY 12550
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  /20

  $349,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,484 Sq Ft

  13 N Aspen Rd, Middletown, NY 10940

  NO HOA FEES! LOW TAXES!! Welcome to effortless living in the heart of Middletown! This turnkey, move-in ready 3-bedroom, 1.5-bath home has been thoughtfully updated with modern finishes and designed for comfortable everyday living. From the moment you step inside, you’re greeted by a bright, inviting foyer and a fresh, stylish interior that feels like home. The beautifully updated kitchen

  Carmela Lopez Borrazas Serhant LLC

  13 N Aspen Rd, Middletown, NY 10940
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  /50

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft

  233 Blooming Grove Turnpike, New Windsor, NY 12553

  Nestled on a lovely one acre lot, this 3-bedroom, 2-bath Colonial offers timeless character and 1,734 square feet of space. With solid bones and a classic layout, this home is ready for your updates and a fresh touch to truly shine again. Enjoy the peaceful garden setting with magnolia, apple, peach and pear trees; lots of perennials and hydrangeas too! A tranquil stream runs near one end of the

  Susan Hamilton Keller Williams Realty

  233 Blooming Grove Turnpike, New Windsor, NY 12553
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  /9

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,262 Sq Ft

  6 Riverview Ave, New Windsor, NY 12553

  Charming opportunity awaits with this 3-bedroom, 2-bath ranch-style home situated on over a half-acre in a convenient commuter location close to the New York State Thruway, Interstate 84, public transportation, shopping and dining. This property offers tremendous potential for the right buyer, featuring a spacious layout, rear deck overlooking a wooded setting, with an attached 1 car garage and a

  Steve Esposito HomeSmart Homes & Estates

  6 Riverview Ave, New Windsor, NY 12553
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  /27

  $359,000

  $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 746 Sq Ft

  797 Forest Glen Rd, Monroe, NY 10950

  Welcome to your new sanctuary in the sought-after Lake Sapphire subdivision of Monroe, New York. This charming two-bedroom, one-bathroom home serves as an ideal entry point for first-time buyers or a serene getaway for those seeking a vacation retreat within the prestigious Monroe-Woodbury School District. The interior boasts a vibrant open-concept design that centers around a stunning eat-in

  Courtney Tablante Keller Williams Realty

  797 Forest Glen Rd, Monroe, NY 10950
• 

  

  /39

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft

  173 Franke Rd, Huguenot, NY 12746

  Well maintain like new high ranch property built in 2018, sit on 6 acres lot. 3 bedrooms 2 full bathroom with 10 fts ceiling basement.tThe current year's tax is $7,559.26,

  Feng Chang Acer Realty Inc

  173 Franke Rd, Huguenot, NY 12746
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  /3

  $210,000

  $15K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,097 Sq Ft

  211 N Miller St, Newburgh, NY 12550

  Brownstone in Newburgh, NY, offering incredible potential for the investor. This handyman special needs a complete rehab, making it the perfect canvas to bring your vision to life. With five possible bedrooms, the property is spacious and full of possibilities. Located near the waterfront and downtown shops, it offers a prime location with great amenities nearby. Don’t miss this opportunity to

  Sy Mujovic I Realty LLC

  211 N Miller St, Newburgh, NY 12550
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  /12

  $489,000

  New Construction $90K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  6 Mark Dr, Port Jervis, NY 12771

  New Construction in the Town of Deerpark! Just 1.5 miles from the Historic City of Port Jervis!Be part of the process and make this home truly yours! Currently under construction, this 3-bedroom, 2-bath bi-level home offers 1,716 sq ft of thoughtfully designed living space in a quiet, desirable location.Now is the perfect time to add your personal touch - choose finishes, make

  Dominick Tufano RE/MAX Benchmark Realty Group

  6 Mark Dr, Port Jervis, NY 12771
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  /24

  $479,000

  • 4 Beds
  • 2 Baths

  92 Center St, Highland Falls, NY 10928

  Fantastic investment opportunity in the heart of Highland Falls! This well-maintained duplex features two units, each offering 2 bedrooms and 1 full bath, making it ideal for investors or owner-occupants looking to offset their mortgage with rental income. Both units provide comfortable living spaces, functional layouts, and strong rental potential. Features new flooring and freshly painted

  MARCELLA GARCIA Century 21 Alliance Rlty Group

  92 Center St, Highland Falls, NY 10928
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  /47

  $465,000

  • 3 Beds
  • 2 Baths
  • 2,055 Sq Ft

  122 Rolling Meadows Rd, Middletown, NY 10940

  Welcome to your dream home in the heart of Middletown, NY! This beautifully maintained 4 bedroom, 2 bathroom home with a bonus room/home office offers the perfect blend of comfort, convenience, and lifestyle. Nestled in a quiet neighborhood, this spacious property is ideal for today’s modern living with flexible space for working from home, entertaining guests, or simply relaxing in style. The

  Kristine Many Keller Williams Realty

  122 Rolling Meadows Rd, Middletown, NY 10940
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  /30

  $474,999

  $25K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,419 Sq Ft

  1168 County Route 12, New Hampton, NY 10958

  Welcome to 1168 County Route 12, a charming Hudson Valley retreat offering the perfect blend of country living and commuter convenience. This spacious home sits on a generous lot, surrounded by scenic views and peaceful surroundings, yet only minutes from Route 17, I-84, and the Metro North station for an easy ride into NYC. Inside, you’ll find a bright and versatile layout with room to grow,

  Daniel Mattiello Keller Williams Realty

  1168 County Route 12, New Hampton, NY 10958
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  /7

  $500,000

  • Land
  • 9.78 Acres
  • $51,125 per Acre

  30 Harding Way, Chester, NY 10950

  An exceptional opportunity for builders and investors in the highly desirable Town of Chester and Town of Monroe, within the Monroe–Woodbury School District. This offering includes four contiguous lots for the price of one, providing significant development potential. The assemblage consists of 30 Harding Way (0.18 acres; Section 27, Block 3, Lot 11), sold together with the adjoining parcels: Lot

  Ida Payne Keller Williams Realty

  30 Harding Way, Chester, NY 10950
• 

  

  /29

  $275,000

  • 1 Bed
  • 1 Bath
  • 886 Sq Ft

  407 Old Mill Rd, Southfields, NY 10975

  Welcome Home! This uniquely styled 1st floor condo features comfort, convenience & privacy. This end unit features a large eat-in-kitchen with updated appliances, pantry and walk-out to your own rear deck. Beautiful crown molding throughout with custom blinds and unique stone wall with mantel fireplace & firebox. Large second room features custom cabinetry and can be used as 2nd bedroom with some

  Ann Marie Silvani Howard Hanna Rand Realty

  407 Old Mill Rd, Southfields, NY 10975
• 

  

  /19

  $395,000

  • 1 Bed
  • 2 Baths
  • 1,354 Sq Ft

  25 Village Cove, Warwick, NY 10990

  Welcome to 25 Village Cove in the heart of Warwick, NY — a beautifully renovated condo that perfectly blends modern updates with low-maintenance living. This move-in ready home features a thoughtfully redesigned interior with updated finishes, stylish porcelain tile flooring, an upgraded kitchen with 28 cabinets, and refreshed baths designed for today’s lifestyle. Enjoy the convenience of public

  Rebecca Matta-Candela Keller Williams Realty

  25 Village Cove, Warwick, NY 10990
• 

  

  /43

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,795 Sq Ft

  50 Holland Ave, Pine Bush, NY 12566

  Imagine finding your ideal suburban haven! This stunning property boasts vinyl siding, a spacious new patio perfect for outdoor entertaining, and a bright, airy kitchen with a center island that seamlessly blends modern style with contemporary flair. Brand new stove with built-in air fryer, new microwave and new dryer !! all add to this steal of a deal. Many high ceilings, skylights, and

  Sheri Chablis Sohn Real Estate Corp

  50 Holland Ave, Pine Bush, NY 12566
• 

  

  /38

  $499,000

  • 6 Beds
  • 3 Baths
  • 2,640 Sq Ft

  157 Chambers St, Newburgh, NY 12550

  This exceptional legal 3-family residence is perfectly situated in the sought-after Historic East End of Newburgh, just minutes from the vibrant downtown waterfront, restaurants, shops, and major transportation. A rare opportunity for investors seeking immediate cash flow and long-term appreciation in an area with strong and consistent rental demand. Beautifully renovated and move-in ready, this

  Kieran Dwyer Double C Realty

  157 Chambers St, Newburgh, NY 12550

Showing Results 241 - 280, Page 7 of 13