Orange County NY Homes under $500,000

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  /23

  $474,900

  $25K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  157 Stage Rd, Monroe, NY 10950

  Village living at 157 Stage Road delivers charm, walkability, and carefully preserved character paired with thoughtful, modern upgrades. Located in the heart of the Village of Monroe, this sidewalk neighborhood home features updated vinyl siding and has been meticulously and masterfully renovated while maintaining its warm historic appeal. Inside, beautiful pine floors, exposed brickwork, and

  Rosalie Cook Weichert Realtors

  157 Stage Rd, Monroe, NY 10950
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  /34

  $485,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,656 Sq Ft

  108 St Andrews Rd, Walden, NY 12586

  Welcome home to this charming, Cape Cod on 3/4 of an acre of scenic views in the Valley Central School District. You will be pleasantly surprised with this well maintained, light filled home showing off the attractive hardwood floors on the first floor, thermal windows, including bright bay window with seat, as well as a wood burning fireplace. The outdoor space is a beautiful and peaceful level

  Lisa Maraday eXp Realty

  108 St Andrews Rd, Walden, NY 12586
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  /35

  $349,999

  • 2 Beds
  • 1 Bath
  • 1,244 Sq Ft

  23 Ardmore St, New Windsor, NY 12553

  Rare opportunity to own a well-maintained 2-bedroom ranch in the desirable Cornwall School District for under $350,000! Situated on just over 1/3 of an acre in an established neighborhood, this one-level home offers comfortable living with great outdoor space and scenic mountain views.The home features a welcoming covered front porch and a side deck, ideal for relaxing or entertaining.

  Thomas Lawrenson Howard Hanna Rand Realty

  23 Ardmore St, New Windsor, NY 12553
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  /34

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  24 Crescent Place, Middletown, NY 10940

  Welcome to 24 Crescent Place, Middletown, NY. Affordable, move-in-ready homes with a detached garage, private driveway, and recent updates are becoming increasingly difficult to find, making this an exceptional opportunity for both homeowners and investors. This charming Colonial features 3 bedrooms, 1 full bathroom, comfortable living spaces, ample storage, and a functional layout designed for

  Yisroel Weiss Team W Realty LLC

  24 Crescent Place, Middletown, NY 10940
• 

  

  

  /35

  $465,000

  • 3 Beds
  • 2.5 Baths
  • 1,701 Sq Ft

  18 Saint Joseph Place, New Windsor, NY 12553

  Welcome to this gorgeous 3 Bedroom 3 Bathroom ( 2 Full, 1 Half) two story with 1700 sq ft of living space. Updated kitchen with stone counter tops. Hardwood flooring throughout. Three bedrooms upstairs featuring a primary bedroom with en suite full bathroom. One car detached garage with space for several cars on the paved asphalt driveway. Awesome patio area in the back of the house. This

  Scott R. Amendolare, Sr. RE/MAX Benchmark Realty Group

  18 Saint Joseph Place, New Windsor, NY 12553
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  /50

  $225,000

  $150K PRICE DROP

  • Land
  • 3 Acres
  • $75,000 per Acre

  331 Mountain Lodge Rd, Blooming Grove, NY 10914

  Only 90 minutes from NYC. Reminiscent of the iconic swimming holes of the Catskills, let the sounds of nature soothe you from your private stream and 20-foot waterfall. Fully engineered for a 3 bedroom, 3 bath home, the leg work has already been done. Complete survey with topography, perk test, soil samples and well and septic engineering were done. The 3-acre lot spans across a cleared homesite,

  Lisa Mulcahy Ellis Sotheby's Intl Realty

  331 Mountain Lodge Rd, Blooming Grove, NY 10914
• 

  

  /34

  $450,000

  Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,498 Sq Ft

  99 Univoice St, Maybrook, NY 12543

  Turn-Key Perfection on a Premier Corner Lot! Welcome home to 99 Unavoice Street, a beautifully maintained and spacious classic high-ranch situated on a bright, manicured corner lot in Maybrook, NY. Priced right and move-in-ready, this property perfectly blends smart design with everyday functionality, nestled in a peaceful, sidewalk-lined neighborhood known for its small-town charm and

  John Ricco Keller Williams Realty

  99 Univoice St, Maybrook, NY 12543
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  /44

  $415,000

  $25K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,203 Sq Ft

  27 Cooper Dr, Monroe, NY 10950

  Charming ranch-style home located on a quiet dead-end street in a desirable area of Monroe. This well-maintained 3-bedroom, 1-bathroom home offers comfortable single-level living and a highly convenient commuter location, approximately one hour from New York City with easy access to major highways, as well as nearby train and bus transportation. The home features an eat-in kitchen with new

  Susan Giordano Hudson Premium Realty

  27 Cooper Dr, Monroe, NY 10950
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  /14

  $220,000

  $29K PRICE DROP

  • Land
  • 5 Acres
  • $44,000 per Acre

  0 Cronk Rd Unit ONEH6301028, Newburgh, NY 12589

  Now is the time!! Come take a look! Recently mowed and ready for your showing. This wooded 5 acre lot waiting for the house of your dreams to be built. This property gives the appeal of shade and privacy, with an area already graded off for a house. These 5 acres are surrounded by lots of mature green trees and stone walls around much of the property. It is located on a private road just off of

  MaryAnn Barnhart HomeSmart Homes & Estates

  0 Cronk Rd Unit ONEH6301028, Newburgh, NY 12589
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  /17

  $240,000

  • 3 Beds
  • 2 Baths
  • 1,435 Sq Ft

  6 White St, Port Jervis, NY 12771

  Located on a quiet neighborhood street, this spacious 3 bedroom, 2 full bath home is full of character, charm, and opportunity. You’ll appreciate the original wood trim, hardwood floors in the living and dining rooms that are waiting to be brought back to life, and the inviting layout that offers both functionality and flexibility. A standout feature of the home is a large bonus room on the main

  Dominick Tufano RE/MAX Benchmark Realty Group

  6 White St, Port Jervis, NY 12771
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  /34

  $299,900

  • 3 Beds
  • 1.5 Baths
  • 1,532 Sq Ft

  87 W Peenpack Trail, Sparrow Bush, NY 12780

  Opportunity to get 10 acres of land while living in a spacious country residence, featuring an open kitchen, large living room, three bedrooms and office area. 2 car garage with loft and full front and back yards roll out to several acres of woods for recreational use. All on a quiet dead end road.

  Asa Lennon RE/MAX Benchmark Realty Group

  87 W Peenpack Trail, Sparrow Bush, NY 12780
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  /15

  $439,900

  • 3 Beds
  • 1.5 Baths
  • 1,650 Sq Ft

  310 Aristotle Dr, Maybrook, NY 12543

  This lovely village home is picture perfect with updated kitchen, stainless appliances, new flooring, formal dining room with sliding doors to the deck overlooking the fenced in yard. Central Air in time for Summer! Beautiful mature tree on the front lawn. Downstairs has a den and enough room for your home office. The two-car garage is attached with plenty of space. This is tucked into a smaller

  Christina Gordon I Realty LLC

  310 Aristotle Dr, Maybrook, NY 12543
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  /26

  $499,999

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,446 Sq Ft

  27 Cedar Trail, Monroe, NY 10950

  Beautiful colonial offering nearly 2,500 sq ft of living space on a quiet paved road near the mountains. Bright open layout with living room flowing into a spacious eat-in kitchen featuring cathedral ceilings, granite countertops, center island, stainless steel appliances, and abundant cabinetry. Main level also includes a full bath, laundry hookup, and flexible room with French doors to the

  Eliezer Safdie Sage Realty Center LLC

  27 Cedar Trail, Monroe, NY 10950
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  /13

  $289,000

  $110K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 965 Sq Ft

  21 Center St, Highland Falls, NY 10928

  Discover the perfect blend of history, culture, and outdoor living in the heart of the Hudson Valley, just moments from the Hudson River. This beautifully renovated 3-bedroom, 1.5-bath home features updates completed in 2023 and offers both comfort and charm. Enjoy walkable village living with nearby shops, restaurants, cafes, and everyday conveniences, along with close proximity to schools,

  Paula Rostron Keller Williams Hudson Valley

  21 Center St, Highland Falls, NY 10928
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  /26

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  11 Oxford Depot, Chester, NY 10918

  Discover the charm and potential of 11 Oxford Depot Rd, Chester, NY — a spacious and inviting 3-bedroom, 2-bath home packed with character, versatility, and value. From the moment you enter, you’ll appreciate the warm hardwood floors, oversized living spaces, and flexible layout designed for today’s lifestyle. Whether you need a home office, playroom, guest room, or creative space, this home

  Aneudy Rosa Keller Williams Realty

  11 Oxford Depot, Chester, NY 10918
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  /27

  $315,000

  • 2 Beds
  • 1.5 Baths
  • 1,202 Sq Ft

  169 Dupont Ave, Newburgh, NY 12550

  Welcome to this charming and inviting home, perfectly suited for first-time buyers, those looking to downsize, or anyone seeking a wonderful and affordable alternative to renting. Nestled in a quiet, peaceful setting, this property offers a sense of tranquility that’s hard to find, while still being conveniently located near major highways, shopping, and a variety of restaurants.This cozy

  Maryann Ryan Weichert Realtors

  169 Dupont Ave, Newburgh, NY 12550
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  /2

  $460,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths

  1 Royce Ave, Middletown, NY 10940

  Excellent investment opportunity in the heart of Middletown! This well-maintained, fully occupied two-family residence offers immediate cash flow with a total monthly income of $3,500. The first-floor unit features a comfortable 1-bedroom, 1-bathroom layout currently rented for $1,600, while the second-floor unit offers a spacious 2-bedroom, 1-bathroom configuration rented for $1,900.

  Joseph Baratta Joseph Baratta Company Realty

  1 Royce Ave, Middletown, NY 10940
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  /17

  $315,000

  $25K PRICE DROP

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

  1155 Washington Green, New Windsor, NY 12553

  2 bedroom, 2 full bath condo. Peaceful, bright, sunny, penthouse unit. Cathedral ceilings, fireplace, new central a/c, brand new washer/dryer in unit. Updated kitchen with quartz counter tops and stainless steel appliances. Relax on your walk out balcony with mountain views. Unit has front and rear entrance. HOA includes clubhouse with pool, tennis, dog park and playground. Garbage and water

  Matthew Hart World Prop Intl Sea to Sky

  1155 Washington Green, New Windsor, NY 12553
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  /9

  $460,000

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

  8 Roberts St, Middletown, NY 10940

  Charming and spacious 2-family home offering versatility, character, and investment potential all in one. Featuring high ceilings, bright airy interiors, and generously sized rooms, this property is ideal for multi-generational living or rental income. Conveniently situated near downtown Middletown’s shops, restaurants, parks, and transportation. Whether you’re an investor or looking to offset

  Yosseline Genao Keller Williams Hudson Valley

  8 Roberts St, Middletown, NY 10940
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  /28

  $329,990

  $3M PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,050 Sq Ft

  289 1st St, Newburgh, NY 12550

  Step into a fully renovated Hudson Valley gem. This beautifully updated home offers a modern, open kitchen with upgraded cabinetry, granite countertops and a massive granite island perfect for cooking and storage. The kitchen opens directly to the backyard for effortless indoor-outdoor living and entertaining. Upstairs you’ll find two comfortable bedrooms and a full bath with tub. The entire

  Serena Johnson eXp Realty

  289 1st St, Newburgh, NY 12550
• 

  

  /14

  $393,000

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  1 Chestnut St, Middletown, NY 10940

  Beautifully renovated 3 bedroom 1 bathroom, everything is brand new, electrical, plumbing and heating, plus with a big corner lot. Plenty of space, beautiful kitchen - come see it today.

  Safdar Mursalin eXp Realty

  1 Chestnut St, Middletown, NY 10940
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  /35

  $365,000

  $35K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  33 E Crossman Ave, Monroe, NY 10950

  Discover 33 E Crossman Avenue! A charming 2-bedroom, 1-bath ranch nestled on a serene 0.38-acre lot in the Village of Monroe. This cozy 700 sq. ft. retreat blends comfort and potential, perfect as a starter home, weekend escape, or investment property. Set in a peaceful, park-like setting with partial woods and seasonal water views, this home offers lake access and timeless character with key

  Kewin Garabito eXp Realty

  33 E Crossman Ave, Monroe, NY 10950
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  /11

  $249,000

  $30K PRICE DROP

  • Land
  • 5 Acres
  • $49,800 per Acre

  1187 Lakes Rd, Warwick, NY 10950

  Fully approved 5 acre lot, ready to build. This lot offers a prime opportunity for your dream home located in the Town of Warwick with frontage on the Trout Brook and in close proximity to enjoy the views of Fitzgerald Falls. Property is close to the Appalachian Trail for those outdoor enhthusiasts, with Trail access within walking distance. Very close to all amenities including the Hostorical

  Jason McGovern Keller Williams Hudson Valley

  1187 Lakes Rd, Warwick, NY 10950
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  /29

  $299,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  22 Seybolt Ave, Otisville, NY 10963

  Move right into this beautifully renovated ranch with beautiful finishes inside and out! This home features a modern kitchen with quartz counters and new stainless appliances, a gorgeously tiled new bathroom, new hardwood floors, a huge deck off the kitchen, and a rocking chair front porch. Updates include new landscaping, new hw tank, new heat, new siding, new windows, and a new roof. Bonus:

  Naomi Streicher Q Home Sales

  22 Seybolt Ave, Otisville, NY 10963
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  /18

  $275,000

  $31K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  423 3rd St, Newburgh, NY 12550

  New on the Market, this1920 two stories home is a perfect fixer upper and is in need of interior renovations to bring it back to its original charm. The Hardwood floors have been kept in fairly good shape throughout the home. The woodwork on all levels has been maintained throughout the home as well!The interior rooms have 3 bedrooms,2 full baths, spacious Livingroom as well as the dining

  Lou Shorette Century 21 E & M Williams Rlty

  423 3rd St, Newburgh, NY 12550
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  /20

  $429,000

  • 3 Beds
  • 2.5 Baths
  • 1,632 Sq Ft

  324 Walnut Ave, New Windsor, NY 12553

  Located in the scenic Beaver Dam Lake area, this charming two-story home offers the perfect setting for easy living and memorable adventures! Enjoy a day of boating, swimming, or fishing on the lake, then unwind in your own backyard oasis for al fresco dining. Building mechanicals have recently been updated with high-efficiency equipment for peace of mind and trouble-free operation. This location

  Charles Buser Charles J Buser

  324 Walnut Ave, New Windsor, NY 12553
• 

  

  /37

  $479,900

  • 4 Beds
  • 2.5 Baths
  • 2,331 Sq Ft

  36 Hoover Dr, Middletown, NY 10940

  Welcome to 36 Hoover Dr, a spacious 4-bedroom, 2.5-bath home located in the desirable Presidential Estates area of Middletown. Situated on a generous .41-acre lot, this property offers great curb appeal, comfortable living space, and plenty of room both inside and out. The home features a functional layout ideal for everyday living and entertaining, with spacious bedrooms, multiple baths, and a

  Luis Fernandez eXp Realty

  36 Hoover Dr, Middletown, NY 10940
• 

  

  /32

  $319,900

  $4K PRICE INCREASE

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft

  2820 Whispering Hills, Chester, NY 10918

  Lovely, Light and Airy 2 Bedroom 1 and 1/2 Bath Unit in Desireable Whispering Hills! Updated Kitchen and Bath, New Carpet and Freshly Painted. Downstairs has a Comfy Living Room with a Wood Burning Fireplace , Sunny Dining Room with Slider to a Patio, Convenient Galley Kitchen, Laundry Area and 1/2 Bath. Upstairs are a Spacious Primary Bedroom , Walkthrough Closet to Full Bath and a Roomy Second

  Anne Marie Scouarnec R2M Realty Inc.

  2820 Whispering Hills, Chester, NY 10918
• 

  

  /18

  $399,900

  $100K PRICE DROP

  • Land
  • 2.3 Acres
  • $173,870 per Acre

  0 Silver Stream Rd Unit KEY929366, New Windsor, NY 12553

  LOCATION - LOCATION...Endless possibilities with this 2.3 acre vacant parcel of land on LC zoning in the middle of town with access to municipal water and sewer with over 200' ft. road front. Just a mile from the main gate of Stewart International Airport and short drive to 9W and I-84 & I-87 intersection.

  George Koudounas RE/MAX Benchmark Realty Group

  0 Silver Stream Rd Unit KEY929366, New Windsor, NY 12553
• 

  

  /40

  $485,000

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

  258 Scotchtown Collabar Rd, Middletown, NY 10941

  Beautiful Single Family Residence in Scotchtown NY area. Move in ready home with nice updates and finishes. Three spacious bedrooms and two full bathrooms. Hardwood floors throughout the home. Central air conditioning with a finish basement. Property located on two acres, with low taxes. Must see. Close to schools, Stores and all major commuting routes.

  Maurice Bailey Neighborhood Assistance Corp

  258 Scotchtown Collabar Rd, Middletown, NY 10941
• 

  

  /13

  $460,000

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  1367 Kings Hwy, Chester, NY 10918

  Historic Colonial Era Home in the Heart of Sugar Loaf, NYLocated just 60 minutes from NYCZoned Residential/CommercialStep into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Original building was built in 1770, this unique property features:• One

  Mark Karten Karten Real Estate Svcs LLC

  1367 Kings Hwy, Chester, NY 10918
• 

  

  /18

  $449,900

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  59 Schobl St, Otisville, NY 10963

  Situated within the highly coveted Minisink School District, this exceptional 3–4 bedroom residence is nestled in a serene and desirable enclave of the Village of Otisville. Thoughtfully designed and beautifully updated, the home showcases a sun-drenched open-concept layout highlighted by soaring cathedral ceilings and refined finishes throughout. The inviting living room centers around a

  Jonathon Lee Keller Williams Hudson Valley

  59 Schobl St, Otisville, NY 10963
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  /36

  $399,999

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

  22 Oak Ln, Middletown, NY 10940

  Step into this beautifully updated three-bedroom home, where comfort and style come together seamlessly. The bright, airy kitchen features elegant stone countertops and sliding glass doors that open to a spacious deck overlooking a fully fenced backyard—perfect for relaxing or entertaining. Natural light fills the inviting living room, which flows effortlessly into the dining area and kitchen,

  Danielle Roche Howard Hanna Rand Realty

  22 Oak Ln, Middletown, NY 10940
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  /28

  $430,000

  • 3 Beds
  • 1.5 Baths
  • 1,784 Sq Ft

  17 Janice Dr, Middletown, NY 10941

  Welcome to 17 Janice Drive, a beautifully updated home nestled in a highly desirable neighborhood close to shopping, restaurants, schools, and major commuter routes. This move-in-ready property features a brand-new roof, fresh interior paint, refinished hardwood floors, updated bathroom tile, stylish new light fixtures, and a completely remodeled kitchen. The stunning kitchen showcases brand-new

  Matthew Skowronski HomeSmart Homes & Estates

  17 Janice Dr, Middletown, NY 10941
• 

  

  /36

  $299,000

  • 2 Beds
  • 2 Baths
  • 1,578 Sq Ft

  3 Diane Ct, Greenwood Lake, NY 10925

  Charming Colonial with GREAT POTENTIAL in Greenwood Lake!Let your imagination be your guide. This charming Colonial-style home offers an exciting opportunity to create something truly special. With approximately 1,580 square feet of living space, the home provides generous proportions and a wonderful canvas for a buyer with vision.Originally renovated in 1989, when a second story was

  Mary Ann Mitchell eXp Realty

  3 Diane Ct, Greenwood Lake, NY 10925
• 

  

  /29

  $285,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft

  276 Temple Hill Rd Unit 2414, New Windsor, NY 12553

  Beautiful 2 Bedroom, 2 Full Bath open floor condo in the sought after Continental Manor community. Gorgeous kitchen with granite countertops, beautiful cabinets, custom backsplash, food pantry, and stainless steel appliances plus laundry. From the dining room, step onto the balcony with awesome views. Large master bedroom includes ensuite. Spacious second bedroom with walk-in closet. Newer

  Tremaine Selby Weichert Realtors

  276 Temple Hill Rd Unit 2414, New Windsor, NY 12553
• 

  

  /24

  $365,000

  • 2 Beds
  • 1 Bath
  • 1,052 Sq Ft

  7 Vincent Ln, Pine Island, NY 10969

  Set on a quiet lane in the heart of Pine Island, 7 Vincent Lane offers the ease of one-level living paired with a long list of meaningful infrastructure improvements already in place. This home balances practicality and comfort with original hardwood floors throughout the main level (even under the laminate in the bedrooms), fresh interior paint, abundant storage, and flexibility for future

  Jamie Corts Compass Greater NY, LLC

  7 Vincent Ln, Pine Island, NY 10969
• 

  

  /43

  $335,000

  Open Sun 12:30PM - 2:30PM $40K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,596 Sq Ft

  104 Canal Dr, Godeffroy, NY 12729

  Charm, Charm, Charm. Location, location, location!! This home has a surprisingly nice layout. Must be seen, very different from most homes. Has old world charm, sits pretty back off quiet country road and property extends back off the road about over 600 ft! Has many recent updates such as newer roof, tilt in windows for easy cleaning, new exterior doors, furnace and hot water heater within past

  Yara Roussos Homes By Yara Realty Group LLC

  104 Canal Dr, Godeffroy, NY 12729
• 

  

  /44

  $485,500

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft

  12 Mid Oaks Dr, Monroe, NY 10950

  Lovely and classic ranch perfectly perched up high with beautiful, peaceful views of the mountains. This home is bright and airy featuring three bedrooms, two full bathrooms, large formal dining room, sun-filled living room and a kitchen that walks out onto a deck overlooking the quiet back yard. You'll love the rich oak floors throughout. Delivered freshly painted and deep cleaned, this house is

  Layla Rose Boyles Century 21 Realty Center

  12 Mid Oaks Dr, Monroe, NY 10950
• 

  

  /36

  $385,000

  • 2 Beds
  • 2.5 Baths
  • 1,215 Sq Ft

  2 Giovanni Ct, Monroe, NY 10950

  Enjoy all that the Timber Hills community has to offer! This beautifully maintained 3-level end unit townhome/condo offers 2 bedrooms, 2.5 bathrooms, and 1,215 sq ft of comfortable living space. The home features an eat-in kitchen, spacious living area with hard wood floors and sliding glass doors leading to your private deck, and a primary bedroom with ensuite bath. The newly finished basement

  Eric Troy Howard Hanna Rand Realty

  2 Giovanni Ct, Monroe, NY 10950

Showing Results 361 - 400, Page 10 of 13