Orange County NY Houses 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

  (845) 447-9473

  138 Reinhardt Rd, Middletown, NY 10940
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  /25

  $420,000 Open Sat 2PM - 4PM

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  71 Commonwealth Ave, Middletown, NY 10940

  Welcome to the perfect blend of comfort, character, and location. Nestled in the vibrant heart of Middletown, NY—just 70 miles from NYC—this beautifully updated home offers a peaceful retreat without sacrificing proximity. Whether you’re commuting for work or play, nearby transportation options, including the Metro-North train and major highways, make travel to the city a breeze. And when you're

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (845) 436-3953

  71 Commonwealth Ave, Middletown, NY 10940
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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
• 

  

  

  /23

  $459,900

  • 3 Beds
  • 1 Bath
  • 1,222 Sq Ft

  19 Dussenbury Dr, Florida, NY 10921

  Live the Life You've Always Imagined – In the Heart of Florida, NYStep into a storybook setting where every season feels like a scene from your favorite Hallmark movie. Nestled in the heart of the charming Village of Florida, this fully reimagined raised ranch offers more than just a home—it offers a lifestyle.Picture yourself waking up in a beautifully updated 3-bedroom, 1-bath

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (845) 581-3474

  19 Dussenbury Dr, Florida, NY 10921
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  /34

  $400,000

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  303 Chandler Ln, Montgomery, NY 12549

  This updated Town of Montgomery ranch home is located on a corner parcel. The oversized remodeled custom eat-in kitchen is a chef's delight with new stainless steel appliance (still under warranty), Kitchen Aid cabinet with roll-outs in breakfast peninsula with storage and the rest of cabinets are Cubetech, ceramic flooring and even a "pot filler" at the stove. There are hardwood floors on the

  

  Frank Gerbes

  RE/MAX Benchmark Realty Group

  (845) 478-8428

  303 Chandler Ln, Montgomery, NY 12549
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  /46

  $475,000

  • 3 Beds
  • 1.5 Baths
  • 2,128 Sq Ft

  42 Knox Dr, New Windsor, NY 12553

  Spacious, well-kept 3-plus bedroom split level home in a quiet neighborhood. A wide drive, mature landscaping.Inside, an airy foyer opens to the formal living room, where a bay window fills the space with natural light and hardwood floors extending through most of the main level. The adjoining open dining room sits steps from the updated kitchen. Granite counters and abundant cabinetry.

  

  Samantha Ortiz

  Howard Hanna Rand Realty

  (845) 552-4305

  42 Knox Dr, New Windsor, NY 12553
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  /38

  $445,000

  • 4 Beds
  • 2 Baths
  • 1,356 Sq Ft

  34 Round Lake Ave, Monroe, NY 10950

  Your Retreat Awaits in the Exclusive Round Lake Community!Discover the perfect blend of comfort, charm, and potential in this inviting 4-bedroom, 2-bathroom home nestled in one of the area's most sought-after private lake communities. With exclusive access to a members-only lake, you’ll enjoy tranquil mornings, peaceful paddleboarding, or weekend escapes just steps from your

  

  Franklyn Crowe

  Weichert Realtors

  (845) 273-3305

  34 Round Lake Ave, Monroe, NY 10950
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  /33

  $429,000

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  15 Riley Rd, New Windsor, NY 12553

  Welcome to 15 Riley Road: This delightful residence was fully renovated from top to bottom. Airy open living space with a gorgeous fire place, four bedrooms and two and a half bathrooms, split unit heating and cooling system.Brand new deck to sip coffee or a get together overlooking a great half an acre property!Do not miss this amazing opportunity!

  

  Inna Sobel

  Atelier Properties LLC

  (845) 382-8386

  15 Riley Rd, New Windsor, NY 12553
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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 to

  

  Kristen Velez

  RE/MAX Benchmark Realty Group

  (845) 412-8180

  93 Weygant Hill, Highland Mills, NY 10930
• 

  

  /23

  $465,000

  • 4 Beds
  • 2 Baths
  • 1,888 Sq Ft

  63 Valley Ave, Newburgh, NY 12550

  This home has so much to offer. From it's location, to the inviting front & back yards where you can sit & relax, or entertain on your back deck & in the pool. As you enter the home, you are greeted by an open & inviting living room with beautiful wood floors. With an open concept galley kitchen, you can easily talk & entertain your guests. Off of the main living area there is a full bath, as

  

  Nicole Gold

  RE/MAX Benchmark Realty Group

  (845) 442-1468

  63 Valley Ave, Newburgh, NY 12550
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  /27

  $429,999

  • 3 Beds
  • 1.5 Baths
  • 2,275 Sq Ft

  4 Bijou Ln, Otisville, NY 10963

  This cozy 3-bedroom, 1.5-bath Cape Cod sits on a peaceful private road in the highly sought-after Minisink School District.From the moment you step inside, you’ll notice craftsmanship that speaks volumes. Check out the remodeled kitchen—it’s a cook’s dream with granite countertops, stylish shaker cabinets, and a gas cooktop and double wall oven that makes hosting or weeknight meals a

  Rachel Hunt Realty Promotions Inc

  4 Bijou Ln, Otisville, NY 10963
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  /32

  $410,000

  • 2 Beds
  • 2 Baths
  • 1,532 Sq Ft

  285 Riley Rd, New Windsor, NY 12553

  Welcome to your new home! This beautifully maintained Hi-Ranch offers the perfect blend of comfort, space, and convenience. Step into a bright, open living room that flows effortlessly into the dining area, complete with a convenient pass-through to the kitchen—ideal for everyday living and entertaining.Enjoy outdoor relaxation on the deck overlooking a private, fenced-in backyard

  Elizabeth Zambuto Stepping Stone Realty

  285 Riley Rd, New Windsor, NY 12553
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  /34

  $449,000

  • 5 Beds
  • 1.5 Baths
  • 3,370 Sq Ft

  2223 New York 94, Beaver Dam Lake, NY 12577

  Welcome to this charming 5-bedroom, 1.5-bathroom farmhouse in Washingtonville, NY. This property offers a perfect blend of classic farmhouse charm and modern functionality. With a spacious layout and thoughtful design, this home is ready to become your new sanctuary. The heart of the home features a formal dining room, ideal for gatherings and special occasions. The expansive living areas are

  Donna Gray Redfin Real Estate

  2223 New York 94, Beaver Dam Lake, NY 12577
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  /31

  $480,000

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft

  295 Lybolt Rd, Middletown, NY 10941

  Spacious home with large yard on a quiet street - what more could you want? This beautiful contemporary home has had many upgrades over the last few years! The main level features an open kitchen, dining room and living room with partial wrap around deck - perfect for entertaining or just extended living space. Three large bedrooms and two full bathrooms complete the upper level. Downstairs

  Britanni Gaucher Keller Williams Realty

  295 Lybolt Rd, Middletown, NY 10941
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  /50

  $459,000

  • 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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  /31

  $459,000

  • 3 Beds
  • 2.5 Baths
  • 1,362 Sq Ft

  904 W Kaisertown Rd, Montgomery, NY 12549

  Welcome to 904 West Kaisertown Road, a well-maintained 3-bedroom, 2.5-bath colonial set on 2.1 private, wooded acres in Montgomery. This home offers a bright, comfortable layout with thoughtful updates throughout. The main level features hardwood floors, abundant natural light, and a pellet stove in the living room that provides whole-house heating. Upstairs, all bedrooms are well-sized and

  Robert Mahling Howard Hanna Rand Realty

  904 W Kaisertown Rd, Montgomery, NY 12549
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  /28

  $490,000

  • 5 Beds
  • 3.5 Baths
  • 2,048 Sq Ft

  101 Patton Rd, Newburgh, NY 12550

  This spectacular Ranch Home is perfect for a mother-daughter setup and offers plenty of space! Recently updated, it features a brand-new kitchen with modern appliances and a pantry, renovated bathrooms, wood floors, and tiled kitchen and baths. Relax by the cozy fireplace or enjoy the spacious family room. There’s even a separate area with a summer kitchen, great for hosting guests! The deck

  Kelly Roebuck Curasi Realty, Inc.

  101 Patton Rd, Newburgh, NY 12550
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  /20

  $488,800

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  1089 County Road 12, New Hampton, NY 10958

  Spacious 1900's Farmhouse in Picturesque New Hampton, New YorkLocated along a quiet and scenic county road in New Hampton, New York, this 4-bedroom, 2.5-bath farmhouse offers the perfect blend of comfort, space, and rural charm. Set on 1.3 acres of land with pastoral views, it’s the ideal retreat for those seeking country living with convenient access to amenities.A massive master

  Rebecca Hundley BHHS Gross & Jansen

  1089 County Road 12, New Hampton, NY 10958
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  /14

  $489,000

  • 3 Beds
  • 1.5 Baths
  • 1,582 Sq Ft

  50 James Rd, Monroe, NY 10950

  Discover the convenience of single-level living in this inviting ranch home nestled in a peaceful Monroe neighborhood. The main living space welcomes you with warm hardwood flooring and a seamless layout. A well-appointed kitchen features, appliances, and clean recessed lighting—perfect for both everyday meals and weekend hosting. The adjoining dining area makes gathering a breeze.

  Joe Goldberg Golden Star Realty Group Inc

  50 James Rd, Monroe, NY 10950
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  /33

  $490,000

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  9 Vascello Rd, New Windsor, NY 12553

  Gorgeous, meticulously maintained, and recently updated 3 bed 2 bath home located in the highly sought-after Beaver Dam Lake community with Washingtonville Schools. Notice the curb appeal as soon as you pull into the just re-done driveway lined with solar lights and new siding. Walk in and notice the gleaming hardwood floors and freshly painted walls throughout. Open floor plan allows the main

  Tremaine Selby Weichert Realtors

  9 Vascello Rd, New Windsor, NY 12553
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  /26

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,334 Sq Ft

  24 Patricia Ln, Washingtonville, NY 10992

  Welcome to 24 Patricia Lane, a beautifully updated single-family home in the heart of Washingtonville! Featuring 3 bedrooms, 2 full bathrooms, and 1,340 sq ft of thoughtfully designed living space, this home combines modern comfort with classic charm.Step inside to find fresh paint throughout, gleaming hardwood floors, and a bright, open layout perfect for both everyday living and

  Siobhan Scanlan Win Morrison Realty-K

  24 Patricia Ln, Washingtonville, NY 10992
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  /33

  $451,000

  • 2 Beds
  • 1 Bath
  • 1,072 Sq Ft

  17 Northside Ln, Greenwood Lake, NY 10925

  This One-of-A-Kind home you don't want to miss! Legal 2 Bedroom / 1 Bath has so much more to offer! Master Bedroom with a walk-in closet that's just as big. Part of which could be converted into a master bathroom. Fully finished basement area with storage galore and its own outside entrance. Use your imagination to make this space anything you want. A FROG (sq. ft. not included) over 2 car

  Kim Cross HomeSmart Homes & Estates

  17 Northside Ln, Greenwood Lake, NY 10925
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  /41

  $460,000 Open Sun 12PM - 2PM

  • 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
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  /21

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  513 3rd St, Newburgh, NY 12550

  Call this gem your forever home! The craftmanship in this stunning one level living town of Newburgh home is exceptional. First level presents a beautiful new kitchen (November 2022), including quartz counter tops and subway tile backsplash. All the bedrooms boast handcrafted closet organizers. Second story includes a huge primary bedroom with elegant ensuite bathroom, two walk in closets and a

  Kathleen Rafferty RE/MAX Benchmark Realty Group

  513 3rd St, Newburgh, NY 12550
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  /23

  $459,000

  • 1 Bed
  • 1 Bath
  • 564 Sq Ft

  582 Jersey Ave, Greenwood Lake, NY 10925

  Imagine your own private Fourth of July fireworks show, right from your lakefront deck. With panoramic water views and the sky lit up in color, there's no better seat for the celebration! 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,

  Brenda Wiley Howard Hanna Rand Realty

  582 Jersey Ave, Greenwood Lake, NY 10925
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  /49

  $455,000

  • 3 Beds
  • 1 Bath
  • 1,625 Sq Ft

  7 Archery Rd, Newburgh, NY 12550

  Absolutely gorgeous 3 bedroom well-maintained brick ranch with nothing to do but move-in! Large living room with bow window and carpet installed 1 year ago. Dining room showcases gleaming hardwood floors. Eat-in kitchen equipped with newer stainless steel appliances, custom backsplash, plenty of cabinet space, and double sink. Kitchen leads to beautiful sunroom lined with windows and sky lights,

  Tremaine Selby Weichert Realtors

  7 Archery Rd, Newburgh, NY 12550
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  /27

  $460,000

  • 3 Beds
  • 2 Baths
  • 2,252 Sq Ft

  13 Valley View Dr, New Windsor, NY 12553

  Amazing Price Adjustment!! This charming Cape Cod-style retreat is filled with warmth, comfort, and timeless character. Enjoy the ease of being close to major routes, without the typical traffic noise — the home is well-situated for peace and privacy. Property offers an inviting living room with hardwood floors and a classic brick fireplace — perfect for cozy evenings. The

  Viola Taliaferrow Keller Williams Realty Group

  13 Valley View Dr, New Windsor, NY 12553
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  /41

  $450,000

  • 6 Beds
  • 2 Baths
  • 2,955 Sq Ft

  265 Goodwill Rd, Montgomery, NY 12549

  This spacious 6-bedroom home is full of potential and ready for your vision. Set in a highly desirable area, it offers a rare opportunity to create your dream home in a prime location. With five bedrooms upstairs and a large main-level bedroom, this layout is ideal for multi-generational living or flexible space needs. The home features an oversized living room, two full bathrooms, a dedicated

  Denise Clancy Curasi Realty, Inc.

  265 Goodwill Rd, Montgomery, NY 12549
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  /28

  $459,900

  • 3 Beds
  • 1.5 Baths
  • 1,410 Sq Ft

  8 Hom St, Chester, NY 10918

  This well kept ranch located on a quiet cul-de-sac offers over 1400 sqft and boasts an open and welcoming floor plan with plenty of natural light, making it a warm and inviting space for both you and your guests. With three bedrooms, living room, family room and 1 and 1 1/2 baths, there's plenty of space for a growing family. Hardwood floors throughout creates a cohesive look and feel, while the

  Joao Rodrigues Preferred Properties Real Esta

  8 Hom St, Chester, NY 10918
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  /36

  $459,000

  • 3 Beds
  • 3 Baths
  • 1,820 Sq Ft

  10 Cannon Dr, New Windsor, NY 12553

  Available for sale from original owners ,in move in condition.Split level 3 Bedroom 1Full and 2 Half Baths,Corner lot on a .45 acre in well established neighborhood in New Windsor.Close to the Historic "Knox headquarter", twenty minutes to West Point.50 miles from GWB. Ideal location for commuters.Close to bus terminal,train station,N J transit/metro north and route 84/87

  Pietro Altomare

  10 Cannon Dr, New Windsor, NY 12553
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  /26

  $450,000

  • 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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  /41

  $454,999

  • 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
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  /20

  $455,000 Pre-Foreclosure

  • 3 Beds
  • 2.5 Baths
  • 2,127 Sq Ft

  2 Gerri Ct, Wallkill, NY 12589

  Charming Colonial Near Chadwick Lake – Wallkill SchoolsWelcome to this classic Colonial nestled on over half an acre in the perfectly located near scenic Chadwick Lake. Set within the desirable Wallkill School District, this home offers an excellent opportunity for buyers looking to customize and add their own personal touch.Step inside to find a traditional layout featuring

  Steve Esposito HomeSmart Homes & Estates

  2 Gerri Ct, Wallkill, NY 12589
• 

  /2

  $459,900 Coming Soon

  • 2 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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  /30

  $450,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 1 Bath
  • 1,517 Sq Ft

  11 Willow Ln, New Windsor, NY 12553

  Welcome home to this charming L- shaped brick ranch in desirable New Windsor! Featuring 3 bedrooms, 1 full bath, and 1,517 square feet of living space, this single-level home sits on a generous 0.31-acre lot with room to relax, garden, or entertain outdoors. Updated kitchen featuring brand new white cabinets, a center island with breakfast area and pendant lighting, quartz countertops, new

  Ebru Celik Keller Williams Hudson Valley

  11 Willow Ln, New Windsor, NY 12553
• 

  

  /37

  $419,000

  • 3 Beds
  • 1.5 Baths
  • 1,104 Sq Ft

  87 Coach Ln, Newburgh, NY 12550

  Welcome to 87 Coach Lane in Newburgh, NY — a stunning 3-bedroom, 1.5-bathroom home that has been completely renovated from top to bottom. Step inside to find a stylish but cozy, modern interior featuring refinished hardwood floors, an updated kitchen with contemporary finishes, and freshly painted walls throughout. Every corner of this home has been thoughtfully redesigned for comfort and

  Waldina Almazan RE/MAX Benchmark Realty Group

  87 Coach Ln, Newburgh, NY 12550
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  /30

  $449,900 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,558 Sq Ft

  14 Briarwood Dr, Middletown, NY 10940

  Welcome to 14 Briarwood Drive, a well maintained ranch-style home in the sought after Minisink Valley School District. Perfectly setback from the road giving off a high end presence. Beautiful landscaping and mature trees elevate the curb appeal even further. As you walk through the foyer, you are greeted by a cozy family room featuring a with a French door that opens to a beautiful worry free

  Frank Muccari Cronin & Company Real Estate

  14 Briarwood Dr, Middletown, NY 10940
• 

  

  /33

  $425,000 Open Sun 12PM - 2PM

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

  7 Bigert Dr, New Hampton, NY 10958

  Perfect starter home in the Goshen School District is conveniently located off 17M in New Hampton. This charming home is move-in ready with Life Proof and hardwood floors throughout. Newer architectural roof, newer natural gas boiler and many new energy star rated windows and 2 new energy star storm doors. The home has Solar panels on the roof that contribute to its energy efficiency. There

  Mary Rice Israelski Howard Hanna Rand Realty

  7 Bigert Dr, New Hampton, NY 10958
• 

  

  /27

  $429,000

  • 3 Beds
  • 2.5 Baths
  • 2,223 Sq Ft

  104 Monhagen Ave, Middletown, NY 10940

  Step into timeless charm with this beautifully renovated Victorian-style home! This bright and sunny 3-bedroom, 2.5-bath residence has been thoughtfully updated while maintaining its classic character. Gleaming hardwood floors flow throughout, and the inviting wrap-around porch offers the perfect spot for morning coffee or evening relaxation. Inside, you’ll find an open and airy layout with

  Jeffrey Hozias Howard Hanna Rand Realty

  104 Monhagen Ave, Middletown, NY 10940

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