Orange County NY Homes under $500,000

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  /42

  $475,000

  • 3 Beds
  • 3 Baths
  • 2,542 Sq Ft

  138 Reinhardt Rd, Middletown, NY 10940

  Nestled on 1.5 park like acres with lots of privacy in the back, built in 1969 and lovingly cared for by the same family for over 56 years is this unique front back split level with four levels in the home. Step through the front door to find a half bath, home office with lots of shelving already in place, and second room used as a craft room, play room,or additional home office conveniently

  

  Lynelle Alessi

  Keller Williams Hudson Valley

  (329) 208-2838

  138 Reinhardt Rd, Middletown, NY 10940
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  /49

  $498,000

  • 4 Beds
  • 3 Baths
  • 3,670 Sq Ft

  29 Maiden Ln, Port Jervis, NY 12771

  Due to a job transfer, the current owner must sell - giving you a rare chance to own this beautifully maintained, custom-built brick ranch in one of Port Jervis' most sought-after neighborhoods. Now offered with an additional adjoining lot (.11 acre), this property provides expanded outdoor space and endless potential. Step into timeless sophistication as you enter the grand foyer, where an

  

  RoseMarie Christner

  STEPPING STONE REALTY

  (845) 723-3474

  29 Maiden Ln, Port Jervis, NY 12771
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  /40

  $450,000

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft

  10 Wood Terrace, Newburgh, NY 12550

  This Town of Newburgh four bedroom two- and one-half bath Cape Cod is minutes from the Newburgh/Beacon bridge and Metro North and a commuter's dream. Located in a low traffic community, this home is on almost 1/2 acre. The main floor has hardwood floors under the carpeting. The living room is bright from the large picture window and features a glass enclosed brick fireplace visible from the

  

  Frank Gerbes

  RE/MAX Benchmark Realty Group

  (845) 606-0651

  10 Wood Terrace, Newburgh, NY 12550
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  /21

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,639 Sq Ft

  389 Fair Oaks Rd, Middletown, NY 10940

  Beautiful contemporary capecod offers 3 to 4 bedrooms and 2 full bathrooms. Open kitchen/dining room with stainless steel appliances, brand new stove, microwave is only 1 year old. Large patio in front of the house. Ceramic tiles and hardwood floors throughout. Primary bedroom has a walk-in closet. First floor bedroom makes an ideal guest room, or for someone that doesn't want to do do stairs.

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 208-1615

  389 Fair Oaks Rd, Middletown, NY 10940
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  /49

  $417,000

  • 3 Beds
  • 1 Bath
  • 1,446 Sq Ft

  71 Furnace Trail, Greenwood Lake, NY 10925

  Welcome to 71 Furnace Trail! This one of a kind charmer is waiting for you! Features include- 3 br, updated full bath, stone fireplace, spiral staircase, private deck with backyard views and patio.......All just steps away from commuter bus to NYC. Hurry to schedule a showing!

  

  Tiffany Megna

  RE/MAX Town & Country

  (845) 328-5921

  71 Furnace Trail, Greenwood Lake, NY 10925
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  /37

  $485,000

  • 6 Beds
  • 2 Baths
  • 1,800 Sq Ft

  26 Patricia Ln, Washingtonville, NY 10992

  This spacious six-bedroom residence offers a rare blend of comfort, flexibility, and opportunity. For families, it provides an expansive layout with room for everyone—whether you need multiple bedrooms, guest space, dedicated home offices, or creative areas. The bright sunroom, central air conditioning, and thoughtful updates throughout create a welcoming atmosphere, while the oversized yard with

  

  Alicia Goldman

  Christie's Int. Real Estate

  (329) 216-0754

  26 Patricia Ln, Washingtonville, NY 10992
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  /27

  $469,999

  • 4 Beds
  • 4 Baths
  • 2,800 Sq Ft

  4 Linden Dr, Highland Mills, NY 10930

  Priced to MOVE.....This rare 4-bedroom, 4-bathroom townhome in the sought-after Timber Ridge community of Woodbury, NY—offering many updates, and a versatile location! This spacious multi-level home features a brand new roof (installed June 2025) and an open-concept main level with vaulted ceilings, skylights, and sun-drenched interiors. The oversized kitchen flows into the dining area, which

  

  Erin Connolly

  Artisan Realty

  (845) 393-6635

  4 Linden Dr, Highland Mills, NY 10930
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  /32

  $489,999

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

  93 Weygant Hill, Highland Mills, NY 10930

  Move-in ready with recent updates! Start your day with expansive, picturesque views of the valley, stretching as far as the eye can see. This delightful 3-bedroom, 2-bath home features a first-floor primary suite, an additional bedroom and full bath on the main level, and a spacious upper-level bedroom that offers privacy and versatility.Step outside to your backyard retreat, which backs up

  

  Kristen Velez

  RE/MAX Benchmark Realty Group

  (845) 412-8180

  93 Weygant Hill, Highland Mills, NY 10930
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  /26

  $410,000

  • 4 Beds
  • 2 Baths
  • 1,668 Sq Ft

  31 Beattie Ave, Middletown, NY 10940

  Great 2 family home in the city of Middletown. Each apartment features 2 bedrooms, 1 bathroom. This property is located in a zoning that requires one of the apartments is occupied by the owner. House is well maintained and cared for. Large lot offers plenty of yard and parking. Walk-up attic offers plenty of storage. Each tenant has their own washer and dryer hook-up. Detached 2 car garage ideal

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 208-3980

  31 Beattie Ave, Middletown, NY 10940
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  /9

  $499,900

  • Land
  • 40.2 Acres
  • $12,435 per Acre

  Lot 69.31 Liberty Corners Rd, Warwick, NY 10969

  Absolutely Beautiful Land, level to rolling hills with Gorgeous views on this 40 Acre Parcel. Would be perfect for a residential subdivision, farm enthusiast, grow crops, build your dream farmhouse, build a barn brewery, establish a vineyard, have a solar farm, do some aqua farming in the charming pond. So many possibilities! On the New York New Jersey Border only 90 minutes NYC. Your dream

  

  Donna Geba

  Century 21 Geba Realty

  (845) 622-6154

  Lot 69.31 Liberty Corners Rd, Warwick, NY 10969
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  /37

  $445,000

  • 4 Beds
  • 2 Baths

  34 Round Lake, Monroe, NJ 10950

  

  Franklyn Crowe

  WEICHERT REALTORS

  (845) 606-6760

  

  34 Round Lake, Monroe, NJ 10950
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  /44

  $400,000

  • 2 Beds
  • 1.5 Baths
  • 1,286 Sq Ft

  130 Continental Rd, Cornwall, NY 12518

  This newly listed, move-in ready Contemporary Colonial in the sought-after Town of Cornwall is waiting for you! Nestled on a quiet country road and surrounded by wildflowers and woods, this charming home offers a serene retreat from the hustle and bustle of city life. The newly planted arborvitae trees will provide even more privacy as the years go by. As you step inside, you’ll be welcomed by a

  

  Thomas Lawrenson

  Howard Hanna Rand Realty

  (845) 614-9381

  130 Continental Rd, Cornwall, NY 12518
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  /22

  $449,000

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft

  65 Carson Ave, Newburgh, NY 12550

  Here’s your chance to own an income-generating two-family home in the heart of Newburgh—with owned solar panels, a backyard, and all the updates already done for you. Live in one unit and rent out the other, or keep both as a smart investment. Either way, you’ll love the bright interiors, modern finishes, and the sunny backyard that’s perfect for weekend lounging or hosting friends. And thanks to

  

  Steven Gray

  Compass Greater NY, LLC

  (845) 599-8081

  65 Carson Ave, Newburgh, NY 12550
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  /31

  $475,000

  • 3 Beds
  • 1 Bath
  • 1,242 Sq Ft

  77 Prospect St, Newburgh, NY 12550

  Welcome to 77 Prospect, an impeccably renovated ranch in the City of Newburgh offering the perfect blend of style and comfort. This move-in ready home features three spacious bedrooms and one beautifully updated bathroom, with a bright and open layout that flows seamlessly throughout. The modern kitchen has been thoughtfully redesigned with today’s finishes, opening into the living spaces for

  

  Alicia Goldman

  Christie's Int. Real Estate

  (845) 448-8797

  77 Prospect St, Newburgh, NY 12550
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  /23

  $475,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,856 Sq Ft

  27 Clinton Dr, Washingtonville, NY 10992

  A must see!! Welcome home to this lovingly maintained ranch now ready for YOU to call it home! This double yarded side walk community home located within the Village of Washingtonville has a library, parks, restaurants, public transit to NYC, access to major highways & more! This charming property features 3 bedrooms and 2 full bathrooms. The long driveway leads to mature landscaping with an open

  

  Menecia Jackson

  Keller Williams Realty NYC Grp

  (329) 218-0594

  27 Clinton Dr, Washingtonville, NY 10992
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  /50

  $489,999

  • 5 Beds
  • 2.5 Baths
  • 3,024 Sq Ft

  99 Walnut St, Walden, NY 12586

  WELCOME TO 99 WALNUT ST AND LOOK NO FURTHER! This incredible 125-year-old colonial home within the village of Walden has withstood the test of time. From the moment you step inside you’ll be delighted to see that much of the home’s original character has been beautifully preserved and well maintained throughout. The warm foyer is flanked by a private dining area on the right and a large formal

  Vincent McAteer Terrie OConnor

  99 Walnut St, Walden, NY 12586
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  /41

  $474,999 Open Sat 10AM - 12PM

  • 3 Beds
  • 3 Baths
  • 1,817 Sq Ft

  688 River Rd, Montgomery, NY 12549

  Charming Cape Cod with River & Meadow Views – Valley Central Schools!!! Step into timeless charm with this beautifully maintained 1932 Cape Cod style home offering 3 bedrooms and 3 full bathrooms, located in the Valley Central School District. Perfectly set on a spacious lot, this property combines classic character with modern updates and stunning views of both the Wallkill River and a sprawling

  Richard Baxter Keller Williams Realty

  688 River Rd, Montgomery, NY 12549
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  /26

  $459,999

  • 4 Beds
  • 2 Baths
  • 2,180 Sq Ft

  40 Westwood Dr, Newburgh, NY 12550

  Welcome to this beautifully updated, bright, open and spacious 4-bedroom, 2-bathroom Ranch-style home the beautiful Hudson Valley, NY at Colden Park in the town of Newburgh within the sought-after Valley Central School District. Enjoy a newly renovated kitchen with granite countertops, renovated bathrooms, new roof and siding. This home offers ample space and style. This single home blends

  Marie Touzin Century 21 Realty Center

  40 Westwood Dr, Newburgh, NY 12550
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  /40

  $489,900

  • 3 Beds
  • 2.5 Baths
  • 1,899 Sq Ft

  11 Cobblestone Ln, Middletown, NY 10940

  Welcome to this bright and spacious 3-bedroom, 2.5-bath townhouse, that’s perfect for today’s busy lifestyle. The spacious layout is filled with natural light, creating a warm and inviting atmosphere for all to gather. The main level offers plenty of room for both everyday living and entertaining, while the upper level features comfortable bedrooms, including a primary suite with its own private

  Antoinette Gundersen HomeSmart Homes & Estates

  11 Cobblestone Ln, Middletown, NY 10940
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  /33

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,165 Sq Ft

  33 Mailler Ave, Cornwall, NY 12518

  Come see this beautifully updated ranch home, ideally situated in the highly regarded Cornwall Central School District. This property features a stunning kitchen equipped with quartz countertops and high-end appliances, complemented by a welcoming living room with recessed lighting. Additional features include a spacious garage with overhead storage, a delightful sunroom, and a beautifully flat

  Shulem Goldberger Capital Estate Realty LLC

  33 Mailler Ave, Cornwall, NY 12518
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  /37

  $459,000 Open Sat 12PM - 3PM

  • 3 Beds
  • 3 Baths
  • 1,600 Sq Ft

  2 Hopkins Terrace, Goshen, NY 10924

  A ranch in Goshen is hitting the market very soon! Tucked away on a peaceful dead-end road just outside the Village of Goshen, this 3-bedroom, 3-bath ranch is the kind of home where comfort meets convenience. With 1,600 sq. ft. of living space upstairs and an additional 1,400 sq. ft. of recreation space downstairs, there’s room here for everything you love—whether it’s hosting family, working

  Martha Randazzo Howard Hanna Rand Realty

  2 Hopkins Terrace, Goshen, NY 10924
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  /25

  $494,900

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

  38 Cobblestone Ln, Middletown, NY 10940

  Must see !!! 3 bedroom 2.5 bathroom townhome with crown molding throughout 3 levels of living space Hardwood floors (Acacia)in most rooms with the exception of 1 bedroom and basement which is carpeted.Home features living room with gas fireplace custom mantle and granite surround ,sliding doors to patio and private backyard.2 story open foyer with chandelier. Study / office with French doors for

  Sandra Johnson Keller Williams Realty

  38 Cobblestone Ln, Middletown, NY 10940
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  /45

  $489,900 Open Sat 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 1,692 Sq Ft

  205 Oriole Dr, Montgomery, NY 12549

  Come join the wonderful world of Sweet Montgomery with village and country life at its best! This lovely home located in a desirable tree lined neighborhood has space for everyone to relax and enjoy the lifestyle of a charming town with quaint main street, wonderful shops, museum, restaurants, beautiful village park with fun for all ages (playground, pickleball, basketball & more!) and of course

  Rose Daversa Hudson Valley Home Connection

  205 Oriole Dr, Montgomery, NY 12549
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  /48

  $465,000

  • 3 Beds
  • 2.5 Baths
  • 1,910 Sq Ft

  1004 Hawthorn Way, New Windsor, NY 12553

  Welcome to this light-filled, meticulously maintained townhouse in the desirable community of The Grove. Offering nearly 2,000 square feet of livable space across three levels, this 3-bedroom, 2.5-bath home blends modern finishes with timeless charm. The spacious living room features a cozy gas fireplace flanked by custom built-ins and a custom built-in window seat—perfect for relaxing or

  Jo-Ann Campagiorni

  1004 Hawthorn Way, New Windsor, NY 12553
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  /33

  $460,000

  • 3 Beds
  • 1 Bath
  • 1,284 Sq Ft

  145 S Main St, Florida, NY 10921

  Perfect Starter or Downsize Opportunity on Half an Acre in the Heart of Florida, NY.Welcome to this 3-bedroom, 1-bath home set on a spacious half-acre lot in the desirable village of Florida, NY. Ideal for first-time buyers or those looking to downsize, this property offers a comfortable layout filled with natural light, solid bones, and room to make it your own.Enjoy small-town living

  Veronika Doherty Keller Williams Realty

  145 S Main St, Florida, NY 10921
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  /50

  $464,900 Open Sun 12PM - 3PM

  • 2 Beds
  • 2.5 Baths
  • 2,132 Sq Ft

  241 Tamerisk Ln, New Windsor, NY 12553

  Welcome to Plum Point on Hudson and this spacious, bright and airy, corner unit, townhome that offers plenty of living space and a relaxing lifestyle. Walk into this spacious, freshly painted, open concept living/dining combination with hardwood floors and a fireplace to keep it cozy! There is plenty of storage in the kitchen and natural light streaming through the sliders that lead to the

  Gina Antonucci Easy Lifestyle Real Estate

  241 Tamerisk Ln, New Windsor, NY 12553
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  /26

  $459,900

  • 3 Beds
  • 1 Bath
  • 1,184 Sq Ft

  23 Highland Ave, Monroe, NY 10950

  Welcome to 23 Highland Avenue — a timeless village home in the heart of Monroe, NY.This beautifully refreshed three-bedroom, one-bath residence sits on a quiet, tree-lined street just a short stroll from the center of town. Whether you're commuting to the city or embracing a more relaxed lifestyle, the location couldn’t be more ideal—just minutes from major highways, NYC bus lines, and

  Isaiah Lopez Keller Williams Hudson Valley

  23 Highland Ave, Monroe, NY 10950
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  /36

  $457,500

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  64 Balmville Rd, Newburgh, NY 12550

  Everyone has been waiting for this house. First time on the market, ever, ever, ever! Noted Newburgh and Florida Architect Francis Abreu designed and built this Tudor side-split in 1922 for the Boynton family, the clan that shortly after Francis's brother Henry Abreu would marry into. Bespoke in every way, the house has all the original lighting, fittings, fixtures, and hardware. It is a

  Jeffrey Lease John J Lease REALTORS Inc

  64 Balmville Rd, Newburgh, NY 12550
• 

  

  /50

  $457,000

  • 3 Beds
  • 2 Baths
  • 2,318 Sq Ft

  1410 Us Highway 6, Port Jervis, NY 12771

  Welcome to this stunning 3-level split-style home, nestled on a spacious 1.5-acre lot offering both comfort and versatility. This thoughtfully designed residence features a fully equipped basement with a washer, dryer, water purifier, above-ground oil tank, and furnace. The first level boasts a large open space with walk-out access to the backyard and a cozy fireplace—ideal for energy-efficient

  Wenpeng Guan Keller Williams Hudson Valley

  1410 Us Highway 6, Port Jervis, NY 12771
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  /34

  $459,900

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  355 Temple Hill Rd, New Windsor, NY 12553

  Well-maintained, move-in ready single family home on 1 acre. Finished walk-out basement to patio and large backyard would make a GREAT GUEST OR ENTERTAINMENT space with its 3/4 bath; wet bar; and laundry area!!The lower level also has a CO for a front-facing 200sq ft BUSINESS OFFICE with 1/2 BATH IN A PRIME AREA offering very unique INCOME POSSIBILITIES OR WORK FROM HOME!!On the

  Thomas Hennerty

  355 Temple Hill Rd, New Windsor, NY 12553
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  /41

  $460,000

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

  28 Hillcrest Dr, Salisbury Mills, NY 12577

  Welcome to this beautifully updated 3 bedroom 2 bath ranch style home offering the perfect blend of comfort, style and sustainability. Step into the heart of the home-an open -concept kitchen featuring sleek granite countertops, a large center island perfect for meal prep or entertaining and top of the line stainless steel appliances. Enjoy year round peace of mind with a whole house generator

  Melissa Forsyth Hudson Valley Home Connection

  28 Hillcrest Dr, Salisbury Mills, NY 12577
• 

  

  /22

  $455,000

  • 3 Beds
  • 2.5 Baths
  • 2,390 Sq Ft

  9 Beech St, Newburgh, NY 12550

  Welcome home to this lovingly cared for 3 bedroom, 3 bath sprawling ranch, offering over 2,300 square feet of living space in sought after Balmville section of Newburgh, just minutes from the Hudson River. This spacious ranch, in a serene location, offers ample sized rooms and space to entertain, steps from the Powelton Club, close proximity to the Newburgh Waterfront, I-84 and NYS Thruway,

  Kathleen Rafferty RE/MAX Benchmark Realty Group

  9 Beech St, Newburgh, NY 12550
• 

  

  /23

  $459,000 Open Sun 1PM - 3PM

  • 1 Bed
  • 1 Bath
  • 564 Sq Ft

  582 Jersey Ave, Greenwood Lake, NY 10925

  Don’t miss this exceptional opportunity to own on one of the most desired stretches of Greenwood Lake. This 1 bedroom, 1 bath bungalow cottage features 35 feet of direct lake frontage, a private floating dock, and stunning panoramic water views. Whether you're looking to renovate, expand, or redevelop, the potential here is unmatched. Located just one hour from NYC, Greenwood Lake offers the

  Brenda Wiley Howard Hanna Rand Realty

  582 Jersey Ave, Greenwood Lake, NY 10925
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  /48

  $465,000

  • 3 Beds
  • 2 Baths
  • 1,693 Sq Ft

  243 Union St, Montgomery, NY 12549

  Charming Corner Ranch in the Heart of Montgomery Village Welcome to this beautifully updated and maintained corner ranch in the desirable Village of Montgomery! This move-in ready home features 3 spacious bedrooms and 2 fully updated bathrooms. The modern kitchen is a chef’s delight, complete with sleek granite countertops, stainless steel appliances, and fresh paint throughout.Step

  Joy Gallagher Weichert Realtors

  243 Union St, Montgomery, NY 12549
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  /41

  $454,999 Open Sat 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,448 Sq Ft

  67 Fox Hill Rd, Wallkill, NY 12589

  Price improvement! Back on the Market! Don’t miss the opportunity to make this exceptional property yours. This home features a spacious open kitchen that is truly the heart of the home. Flooded with natural light, it boasts luxurious granite countertops and rich wood floors, perfectly balanced with ample cabinet space to cater to all your culinary needs. Whether you're a gourmet chef or a casual

  Gina Dudgeon Howard Hanna Rand Realty

  67 Fox Hill Rd, Wallkill, NY 12589
• 

  /2

  $460,000

  • 4 Beds
  • 2 Baths
  • 4,312 Sq Ft

  333 Liberty St, Newburgh, NY 12550

  Prime Investment opportunity in the heart of The City of Newburgh! Listed at $460,000. This building is being sold with the adjoining lot; the address for this lot is 335 Liberty Street. Taxes on that lot in 2024 were $361.11. With this bonus additional lot, there is a rare chance to secure a versatile property package in one of the Hudson Valley's most active growth markets. Don't miss your

  Tynisha Pinckney Clarke Realty & Associates LLC

  333 Liberty St, Newburgh, NY 12550
• 

  

  /8

  $460,000

  • 3 Beds
  • 1 Bath
  • 1,380 Sq Ft

  6 Erin Ct, Cornwall, NY 12518

  3 Bedroom 1 Bathroom Cape Cod on 1.24 acres in Town of Cornwall! 2 car carport. Close to shopping, schools and amenities. Sold as-is. Buyer to pay NYS and any local transfer taxes. Cash offers only with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**PROPERTY IS OCCUPIED, NO INTERIOR ACCESS. Do not disturb occupants.

  Ernie Acampora River Realty Services, Inc.

  6 Erin Ct, Cornwall, NY 12518
• 

  

  /23

  $455,000

  • 3 Beds
  • 1 Bath
  • 1,561 Sq Ft

  33 Meadow Ave, Chester, NY 10918

  One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space.Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

  Ernie Acampora River Realty Services, Inc.

  33 Meadow Ave, Chester, NY 10918
• 

  

  /27

  $429,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 1.5 Baths
  • 1,700 Sq Ft

  54 Canterbury Ave, Cornwall, NY 12518

  Welcome to this spacious home on a desirable corner lot in Cornwall, offering both convenience and potential. Recently refreshed with a full interior paint job and beautifully refinished hardwood floors, this property is ready for its next chapter. While some updates are needed, the home’s generous layout provides endless opportunities to create your ideal space.A partially finished

  Shirley Mojica Compass Greater NY, LLC

  54 Canterbury Ave, Cornwall, NY 12518
• 

  

  /49

  $419,999

  • 2 Beds
  • 1 Bath
  • 1,037 Sq Ft

  46 Neversink Dr, Port Jervis, NY 12771

  Welcome to 46 Neversink Drive, a timeless two-story 1880 home filled with character and old-school charm. This home offers 2 bedrooms, 1 bath, and 1,037 square feet of inviting living space on a generous 0.46-acre lot. Inside, you’ll find warm, well-proportioned rooms on the second floor that showcase the home’s historic craftsmanship. Enhanced by modern updates including three brand-new

  Kewin Garabito eXp Realty

  46 Neversink Dr, Port Jervis, NY 12771

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