Orange County NY Homes under $400,000

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  $399,999

  Coming Soon

  • 5 Beds
  • 2 Baths
  • 1,664 Sq Ft

  341 Highland Ave Extension, Middletown, NY 10940

  Welcome to 341 Highland Ave Ext, a bright and airy 4-bedroom, 2-bath split-level home conveniently situated in the heart of town. An inviting open floor plan creates effortless flow throughout the main living spaces, offering comfort, style, and plenty of natural light. Enjoy a level, fenced-in backyard—ideal for outdoor gatherings or peaceful relaxation. With local eateries, shopping, and daily

  Valerie Jewis Keller Williams Realty

  341 Highland Ave Extension, Middletown, NY 10940
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  /39

  $399,000

  • 4 Beds
  • 1 Bath
  • 1,335 Sq Ft

  239 Leslie Ave, New Windsor, NY 12553

  239 Leslie Ave offers the perfect blend of charm, comfort, and convenience in one of New Windsor’s well-established neighborhoods. This beautifully maintained 4-bedroom Cape Cod sits on a spacious .34-acre lot with a fenced backyard, mature landscaping, and easy access to shopping, restaurants, gyms, major highways, and the NYS Thruway. Inside, you’ll find 1,335 square feet of inviting living

  Juan Bautista Serhant LLC

  239 Leslie Ave, New Windsor, NY 12553
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  /41

  $385,000

  $4K PRICE DROP

  • 3 Beds
  • 2 Baths

  72-1/2 Henry Ave, Newburgh, NY 12550

  PRICE IMPROVEMENT!! 72-1/2 Henry Avenue presents a standout opportunity in the heart of Newburgh’s Washington Heights neighborhood. Ideal for both owner-occupants and savvy investors seeking immediate income with future upside. Set on an oversized double lot, this legal two-family property with separate utilities offers approximately 1,452 square feet with two residential units plus an additional

  Hamar Clarke Clarke Realty & Associates LLC

  72-1/2 Henry Ave, Newburgh, NY 12550
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  /18

  $350,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,380 Sq Ft

  6 Erin Ct, Cornwall, NY 12518

  3 Bedroom 1 bath Cape Cod In Cornwall! Located on 1.25 Acres, this cape offers living room with brick fireplace/wood stove & hardwood flooring, family room with tons of natural light, open kitchen, formal dining room & a dinette with bay window & additional of built in cabinet space. 3 season mudroom with door out to side deck. Upper level with 3 bedrooms & full bath. Plenty of parking in your 2

  Ernie Acampora River Realty Services, Inc.

  6 Erin Ct, Cornwall, NY 12518
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  /25

  $390,000

  • 4 Beds
  • 2 Baths
  • 1,652 Sq Ft

  21 Albert St, Middletown, NY 10940

  Charming 4-bedroom, 2-bath home in the heart of Middletown offering space, character, and endless potential! Nestled on a sidewalk-lined street, this property features a welcoming wraparound porch — the perfect spot to relax. Step inside the inviting foyer and into a spacious living room adjacent to the dining room and kitchen featuring a center island, with bathroom conveniently located on the

  Christina Wilger RE/MAX Benchmark Realty Group

  21 Albert St, Middletown, NY 10940
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  /22

  $350,000

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft

  457 1st St, Newburgh, NY 12550

  Imagine having an entire home to call your own — no upstairs neighbors, no shared walls — just your own private space to settle in and make lasting memories. This charming 3-bedroom, 1-bath home offers the comfort, privacy, and breathing room that can be hard to find. Step inside to bright, sun-filled living areas with a welcoming layout that feels inviting from the moment you enter. The three

  Kerri Stretch Howard Hanna Rand Realty

  457 1st St, Newburgh, NY 12550
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  /29

  $399,999

  $25K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 1,658 Sq Ft

  160 Lander St, Newburgh, NY 12550

  Amazing and spacious income-producing multi-family townhouse ready for its next owner! Both units feature two levels and an abundance of natural light, creating a warm and inviting atmosphere. Unit 1 is a newly renovated 3-bedroom, 1-bath apartment with a spacious living area and an open-concept kitchen that flows into the dining room. Two large bedrooms are complemented by two bonus

  Johnni Lindsay HomeSmart Homes & Estates

  160 Lander St, Newburgh, NY 12550
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  /11

  $349,999

  $25K PRICE DROP

  • Land
  • 4.9 Acres
  • $71,428 per Acre

  8 Camelback Rd, Chester, NY 10918

  Nestled at the end of a private cul-de-sac, this 5 acre homesite offers breathtaking mountain and valley views in the sought-after Bull Mill Road area of Monroe/Chester, NY. The property’s gentle slopes create the perfect opportunity for a walkout lower level, allowing you to capture spectacular sunsets. This shovel-ready, fully approved, and engineered building lot features Belgian block

  James Feldhaus eXp Realty

  8 Camelback Rd, Chester, NY 10918
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  /5

  $380,000

  • Land
  • 3.4 Acres
  • $111,765 per Acre

  0 Mountain Farm Rd Unit KEY911830, Tuxedo, NY 10987

  Unique property with easy access from Mountain Farm Road. Perfect flat area for a home, with beautiful stream and seasonal waterfall. Partial lake views in the winter.All within 40 miles of New York CityEqual Opportunity Housing

  Anna Shaw Compass Greater NY, LLC

  0 Mountain Farm Rd Unit KEY911830, Tuxedo, NY 10987
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  /28

  $309,900

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 885 Sq Ft

  34 Lake St, Highland Falls, NY 10928

  Village brick ranch captures the essence of Hudson Valley living with its blend of character, convenience, and historic surroundings! Just minutes from the United States Military Academy at West Point and the scenic Hudson River, this charming home features an eat-in kitchen, generous living room, two spacious bedrooms, and full bath. Beautiful hardwood floors and original woodwork throughout.

  Patricia Tompkins Weichert Realtors

  34 Lake St, Highland Falls, NY 10928
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  /31

  $345,500

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  97 Maple St, Newburgh, NY 12550

  The Ultimate Newburgh Sanctuary | Renovated Stucco Colonial Step into a residence where the timeless elegance of 1920s architecture meets the sophisticated, high-end modern updates today’s most discerning buyers demand. Nestled on a quiet, tree-lined street in an established residential neighborhood, this impeccably maintained Stucco Colonial offers a perfect balance of style, comfort, and

  Jeffrey Morrissey Epique Realty

  97 Maple St, Newburgh, NY 12550
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  /33

  $399,900

  • 5 Beds
  • 1 Bath
  • 1,978 Sq Ft

  189 Lakeside Rd, Newburgh, NY 12550

  Offered for the first time in nearly fifty years, this 1943 Cape Cod sits on a tree-lined stretch of Newburgh's established Orange Lake hamlet. The home lives easily on a single floor, with the primary bedroom, full bath, open kitchen, and main living spaces all on the ground level, plus a full basement for storage or future build-out. Major systems and exterior have been thoughtfully maintained

  Ashley Bartels J. Morreale, LTD

  189 Lakeside Rd, Newburgh, NY 12550
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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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  /35

  $350,000

  • 2 Beds
  • 2 Baths
  • 1,084 Sq Ft

  9 Wildwood Dr, Greenwood Lake, NY 10925

  Charming and well-maintained single-level home offering comfort, versatility, and numerous updates in a desirable commuter-friendly location. This 2-bedroom, 2 full bathroom home features a bright and inviting living room with laminate flooring, vaulted ceilings, skylights, and a cozy wood-burning stove. A loft area provides additional flexible space ideal for storage, a home office, or

  Susan Giordano John J Lease REALTORS Inc

  9 Wildwood Dr, Greenwood Lake, NY 10925
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  /10

  $319,900

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  37 California Ave, Middletown, NY 10940

  MLS Listing Description: Charming 3-bedroom, 1-bath traditional two-story home featuring a spacious, enclosed backyard—perfect for outdoor enjoyment and entertaining. The first floor offers an oversized living room, an open dining area, and a functional kitchen layout ideal for everyday living. Upstairs, you’ll find three comfortable bedrooms and a full bath. A walk-up attic provides convenient

  Jonathon Lee Keller Williams Hudson Valley

  37 California Ave, Middletown, NY 10940
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  /17

  $324,999

  $10K 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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  /14

  $329,500

  $15K 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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  /8

  $310,000

  • 2 Beds
  • 1 Bath
  • 1,384 Sq Ft

  50 Schneider Ave, Highland Falls, NY 10928

  Welcome to 50 Schneider Avenue in the heart of Highland Falls! This well-maintained 2-bedroom, 1-bath home offers a bright kitchen with high ceilings and recessed lighting throughout, creating an open and inviting atmosphere. Recent updates include a roof and hot water heater both under 5 years old, providing added peace of mind for the next owner. Conveniently located near West Point, Bear

  Ramanjit Dhanoa eXp Realty

  50 Schneider Ave, Highland Falls, NY 10928
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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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  /24

  $318,980

  • 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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  /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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  /15

  $369,000

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

  13 N Aspen Rd, Middletown, NY 10940

  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 features gleaming granite

  Carmela Lopez Borrazas Serhant LLC

  13 N Aspen Rd, Middletown, NY 10940
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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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  /19

  $395,000

  Open Sun 1PM - 3PM

  • 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
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  /34

  $375,000

  • 4 Beds
  • 3.5 Baths
  • 3,658 Sq Ft

  102 W Wiley St, Maybrook, NY 12543

  We are proud to offer an amazing opportunity to restore the historic 1912 Colonial located at 102 W Wiley Street in Maybrook. This remarkable home, built entirely from redwood shipped from the West Coast, boasts incredible structural integrity and timeless architectural details. The house features 4 bedrooms, 4 bathrooms, and a total of 12 rooms. One section of the house was formerly used as a

  Aron Ungar eRealty Advisors, Inc

  102 W Wiley St, Maybrook, NY 12543
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  /39

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,224 Sq Ft

  1100 State Route 17a, Greenwood Lake, NY 10925

  Turnkey 3 bedroom, 2 bath home on a corner lot in desirable Greenwood Lake featuring a 1 car detached garage and an impressive list of recent updates. The first floor offers new flooring throughout, a renovated kitchen, and a comfortable living room. Both the primary and secondary bedroom include a walk-in closet. Laundry is conveniently located on the first floor with a stackable washer and

  Tanner Sommese Keller Williams Rlty Integrity

  1100 State Route 17a, Greenwood Lake, NY 10925
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  /9

  $399,900

  • Land
  • 13.6 Acres
  • $29,404 per Acre

  0 Four Corners Rd, Warwick, NY 10990

  13.6 acres, front of the property is wooded, that then opens up to beautiful field property. Property includes some horse fencing. Subdivision map filed with Town. Road frontage access from Four Corners Rd

  Catherine White Raynor Country

  0 Four Corners Rd, Warwick, NY 10990
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  /5

  $300,000

  • Land
  • 6 Acres
  • $50,000 per Acre

  0 Mount Hope Rd, Middletown, NY

  Looking to build? Land available in prime location. Situated directly between Middletown and Town of Mount Hope with easy access to all major roadways. Zoned for residential and agriculture. Buyer/builder to subdivide 5-6 acres from this 37+ acre parcel as agreeable to seller and proposed in contract. Flat, open, cleared land may be suitable for 1-3 building lots. Land to purchase provides

  Amanda Ferrantello Hudson Valley Griffith

  0 Mount Hope Rd, Middletown, NY
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  /11

  $309,900

  $15K PRICE DROP

  • 6 Beds
  • 2 Baths
  • 2,490 Sq Ft

  115 William St, Newburgh, NY 12550

  This is a great legal two family investment property large back yard fenced in. All minor repairs have been done. Noo violations or open permits. First floor has one bedrooms. Second floor has four bedrooms. This is a great value in this market.. Call to see this today. Access,,, Keys are in the listing office for entry after accepted showing. Call for access to Keys after confirmation. More

  Patrick Casilli John J Lease REALTORS Inc

  115 William St, Newburgh, NY 12550
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  /34

  $329,000

  • 4 Beds
  • 1 Bath
  • 1,946 Sq Ft

  14 West St, Port Jervis, NY 12771

  Classic and Spacious Duplex in a desirable neighborhood location in the City of Port Jervis NY. This charming old style inviting duplex offers comfortable, practical rooms with 2 bedrooms upstairs on each side for privacy. One side offers 1.5 baths for added value. Oversized paved driveway gives ample parking space and leads up to a garage building that will support your storage needs. Utilities

  Joyce Klimkiewicz Skipping Stones Realty

  14 West St, Port Jervis, NY 12771
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  /29

  $338,000

  Open Thu 5PM - 7PM

  • 2 Beds
  • 1 Bath
  • 748 Sq Ft

  21 Lakeview Dr, Monroe, NY 10950

  Lake Community Living! Whether your passion is a weekend or summer getaway, downsizing or looking for your first home that won't break the bank it's all here at 21 Lakeview Dr. This two bedroom charmer is updated and ready for you to move in. The home sits up high to access the lake view. Inside you'll find a comfortable living area, the primary bedroom with a walk in closet, a second guest

  Karen Taphorn Howard Hanna Rand Realty

  21 Lakeview Dr, Monroe, NY 10950
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  /18

  $315,000

  • 2 Beds
  • 1 Bath
  • 689 Sq Ft

  15 Anthony St, Middletown, NY 10940

  Welcome to this beautifully up to date, single-family home offering the perfect blend of comfort, style, and functionality. At approximately 690+/- sq ft, this move-in-ready home makes exceptional use of space with a bright and inviting layout ideal for everyday living.The open-concept living area features recessed lighting and flows seamlessly into a stunning kitchen highlighted by stylish

  Eliezer Salcer Preferred Properties Real Esta

  15 Anthony St, Middletown, NY 10940
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  /15

  $325,000

  $5K PRICE DROP

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

  305 Gazebo Ct, New Windsor, NY 12553

  This beautifully maintained 2 bedroom, 2 full bath ground-floor condo offers comfort, convenience, and thoughtful updates throughout. Enter inside to an open and airy floor plan featuring a cozy gas fireplace that anchors the living space—perfect for relaxing evenings at home.The spacious kitchen flows seamlessly into the dining and living areas, making entertaining effortless. Enjoy the

  Brittany Barry HV Premier Properties Realty

  305 Gazebo Ct, New Windsor, NY 12553
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  /45

  $389,900

  • 3 Beds
  • 1.5 Baths
  • 1,766 Sq Ft

  23 Raymond Dr, Port Jervis, NY 12771

  Escape to the country, in lovely Greenville NY, to a sweet, three bedroom, two bathroom haven, with peaceful surroundings and gorgeous views. Offering an open plan kitchen with granite counter tops and breakfast bar. Opening up to a comfortable good size living room. A light filled dining room flows to a den, leading out to a large deck, partially covered for relaxation and beautiful views. Lake

  Kim Lesley Spaughton Our House Real Estate Group

  23 Raymond Dr, Port Jervis, NY 12771
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  /13

  $339,999

  • 4 Beds
  • 1.5 Baths
  • 2,298 Sq Ft

  45 1/2 Sussex St, Port Jervis, NY 12771

  Beautifully renovated Colonial offering 4 bedrooms, 2 bathrooms, and a spacious layout with modern finishes throughout. Features include a stunning kitchen with stainless steel appliances, updated bathrooms, ductless cooling, and plenty of parking. Conveniently located close to shops, schools, and major routes. A great opportunity you don’t want to miss. Buyer's agents are welcome.

  David Laufer MS Realty Group USA, Inc

  45 1/2 Sussex St, Port Jervis, NY 12771
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  /32

  $324,999

  • 2 Beds
  • 1.5 Baths
  • 1,168 Sq Ft

  12 Homestead Village Dr, Warwick, NY 10990

  Desirable Village of Warwick Townhome in Amenity-Rich Homestead Village. Set in the charming and historic Village of Warwick, this pet-friendly end-unit townhome in sought-after Homestead Village offers the perfect blend of comfort, convenience, and low-maintenance living—providing added privacy and natural light.Residents enjoy access to an impressive array of amenities, including three

  Vincent Reda Keller Williams Realty

  12 Homestead Village Dr, Warwick, NY 10990
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  /20

  $335,000

  $30K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,624 Sq Ft

  70 Deer Trail N, Greenwood Lake, NY 10925

  Greenwood Lake! Dreaming of owning your own Lake House to swim, fish, boat? Located in the private Indian Park Lake Community, This 2 bedroom 1.5 bath offers huge living room with floor to ceiling windows giving views of the lake while illuminating the entire 1st floor. Upper level has full bath, 2 spacious bedrooms & an office. Walk out of your bedroom onto your rear balcony & enjoy your morning

  Ernie Acampora River Realty Services, Inc.

  70 Deer Trail N, Greenwood Lake, NY 10925

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