Middletown, NY Homes for Sale

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  /38

  $979,900

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  255 Howells Rd, Middletown, NY 10940

  Enter the gates of this remarkable 36.8-acre estate to discover a distinguished 5-bedroom, 5-bathroom residence offering 4,200 square feet of living space. The property includes a substantial two-story post-and-beam barn with horse stalls, multiple wells, and an additional hay barn—ideal for equestrian or agricultural use. A serene natural pond and a mix of rolling pastures and wooded areas

  Jonathon Lee Keller Williams Hudson Valley

  255 Howells Rd, Middletown, NY 10940
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  /48

  $675,000

  • 4 Beds
  • 3 Baths
  • 4,080 Sq Ft

  225 Brown Rd, Middletown, NY 10941

  STUNNING 4-Bedroom, 3-Bathroom CONTEMPORARY LUXURY Home with Modern Upgrades. This turn-key beauty features a gorgeous updated eat-in kitchen with quartz countertops and an island, brand new stainless steel appliances fresh out the box, new cabinets a stylish backsplash with doors that lead to the back deck, perfect for entertaining. A formal fining room is followed by an oversized living room/

  Sandra Arnez Keller Williams Hudson Valley

  225 Brown Rd, Middletown, NY 10941
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  /26

  $479,900

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

  15 High Ridge Ln, Middletown, NY 10940

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

  Patricia Sassi RE/MAX Benchmark Realty Group

  15 High Ridge Ln, Middletown, NY 10940
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  /10

  $339,900

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  37 California Ave, Middletown, NY 10940

  MLS Listing Description: Charming 3-bedroom, 2-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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  /2

  $40,000

  • 550 Sq Ft

  40 Ivory Ln, Middletown, NY 10940

  SPACIOUS LAND AVAILABLE FOR SALE IN DESIRABLE AREA OF MIDDLETOWN NY

  ALISON NIXON eXp Realty

  40 Ivory Ln, Middletown, NY 10940
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  /12

  $260,000

  $9K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 802 Sq Ft

  11 Philcox Rd, Middletown, NY 10940

  Rare opportunity to own two homes next door to each other in the Pine Bush School District. Single family home 2 bed, 1 bath, recently updated. Quiet road with only two homes, both originally owned by the same family, offering privacy and flexibility. Conveniently located near shopping, dining, train service, Resorts World Catskills, Kartrite Waterpark, and Bethel Woods Center for the Arts. Easy

  Joseph Rubeo Keller Williams Hudson Valley

  11 Philcox Rd, Middletown, NY 10940
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  /48

  $725,000

  • 3 Beds
  • 2.5 Baths
  • 2,678 Sq Ft

  428 Prosperous Valley Rd, Middletown, NY 10940

  Tucked away on 16 private acres, 428 Prosperous Valley Road offers the space, privacy, and custom details you’ve been looking for. This 3 bedroom, 2.5 bath home features a bright open layout, highlighted by a dramatic great room with 18-foot ceilings and beautiful natural light. The main level offers 9-foot ceilings, custom hardwood floors, formal moldings, Andersen windows, and a spacious

  John Olivero Keller Williams Realty

  428 Prosperous Valley Rd, Middletown, NY 10940
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  /44

  $299,999

  • 3 Beds
  • 1.5 Baths
  • 1,428 Sq Ft

  54 Whitman Ct, Middletown, NY 10941

  Welcome home—a move-in ready 3-bedroom, 1.5-bath townhouse located in a quiet cul-de-sac within the Pine Bush School District. With NO HOA fees, this is an incredible opportunity for buyers seeking low-maintenance living without the added monthly costs.This well-maintained home offers a functional and inviting layout, perfect for everyday living and entertaining. The kitchen and dining area

  Jennifer Lappe Keller Williams Realty

  54 Whitman Ct, Middletown, NY 10941
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  /11

  $339,900

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

  5 Kendal Ln, Middletown, NY 10940

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

  Jonathon Lee Keller Williams Hudson Valley

  5 Kendal Ln, Middletown, NY 10940
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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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  /21

  $589,900

  • 3 Beds
  • 2.5 Baths
  • 2,504 Sq Ft

  37-39 Wisner Ave, Middletown, NY 10940

  Welcome to this newly remodeled 3 to 4-bedroom, 3-bath Colonial situated on a rare double lot at 37–39 Wisner Ave in Middletown. This move-in-ready home offers spacious living areas, modern updates, and a convenient location close to everything. The first floor features a generously sized living room, a formal dining room, and a bright kitchen with dinette area that opens through sliding doors to

  Jonathon Lee Keller Williams Hudson Valley

  37-39 Wisner Ave, Middletown, NY 10940
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  /48

  $574,990

  • 3 Beds
  • 2 Baths
  • 2,596 Sq Ft

  12 Oak Ridge Rd, Middletown, NY 10940

  Welcome to 12 Oak Ridge Road, located in the Presidential Heights residential neighborhood, an upscale sought-after community with picturesque mountain views. Upon entering this meticulously kept contemporary home, you are welcomed by a warm character, and a cozy feel that makes this home instantly inviting. Offering approximately 2600 square feet of living space, this home is thoughtfully laid

  Jacqueline Henry-Thompson Jackie Henry Realty LLC

  12 Oak Ridge Rd, Middletown, NY 10940
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  /49

  $575,000

  $15K PRICE DROP

  • 5 Beds
  • 1.5 Baths
  • 1,790 Sq Ft

  48 Connors Rd, Middletown, NY 10941

  Looking for a move-in ready 5-bedroom Dutch Colonial in the 10940 area? 48 Connors Road offers a fully renovated interior, updated major systems, and a finished walk-out basement, delivering flexible living space and modern finishes in a convenient Middletown location. Come take a look at 48 Connors Road, a beautifully renovated colonial in Middletown that has been updated from top to bottom with

  Kewin Garabito eXp Realty

  48 Connors Rd, Middletown, NY 10941
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  /35

  $200,000

  • Land
  • 51.7 Acres
  • $3,868 per Acre

  Tbd Hall Rd, Middletown, NY 12455

  Hike up to see this spectacular 51.7 acres of prime Real Estate. This property has everything except a road which will have to be built. A previous right of way was moved years ago due to flooding. The walk in does require waterproof boots and a lot of good energy. The parcel has every kind of topography you could imagine. Mouch of it is a large lightly wooded plateau. The southeastern boundary

  William Chris St. John Win Morrison Realty

  Tbd Hall Rd, Middletown, NY 12455
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  /13

  $298,000

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  100 Hillside Dr Unit E16, Middletown, NY 10941

  Highly sought-after Hillside Village community! This quiet upstairs unit offers 2 bedrooms and 2 full bathrooms within a secure, gated environment. Located in the prestigious Goshen School District, this home provides peace of mind and privacy, complemented by the convenience of a recently updated driveway and parking lot.The interior boasts an airy and bright feel thanks to the soaring

  Hai Li Keller Williams Hudson Valley

  100 Hillside Dr Unit E16, Middletown, NY 10941
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  /2

  $99,900

  • Land
  • 13,068 Sq Ft
  • $333,000 per Acre

  28 Genung St, Middletown, NY 10940

  **Great investment opportunity in desirable area in Middletown** This property is zoned C-2. Approved for a Two-family dwelling, but the street level has to be commercial use, per my conversation with the building department ( (475/20 C2 #12 or#16) Not many vacant properties on the market that offer the possibility to build a multi-family unit. This lot is set back from the main road, just behind

  Evelyn Unger Tmimi Weichert Realtors

  28 Genung St, Middletown, NY 10940
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  /8

  $699,999

  • 6 Beds
  • 4 Baths
  • 2,040 Sq Ft

  2467 Route 302, Middletown, NY 10941

  Excellent location and property seeking a savvy investor. Pine Bush schools, fully leased near Highway and less than 5 miles to train. Close to shopping too. Hurry to see before it is gone.

  Myrna Lattore eRealty Advisors, Inc

  2467 Route 302, Middletown, NY 10941
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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

  $1,475,000

  • Land
  • 92.31 Acres
  • $15,979 per Acre

  0 Red Kill Rd, Middletown, NY 12430

  92.30 acres for sale in the Catskill Mountains New York.This secluded and versatile property is now for sale for the first time since 1996. Set above the charming Village of Fleischmanns and just 0.6 miles from Main Street, this 92-acre parcel offers the privacy of a wilderness retreat with the convenience of a village doorstep.-Interior roadways.-A large man-made spring-fed pond and

  peter neumann Listing by Keller Williams Upstate NY Properties

  

  0 Red Kill Rd, Middletown, NY 12430
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  /43

  $745,000

  $670K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 1,395 Sq Ft

  903 Rd, Middletown, NY 12421

  Rare Catskills Investment Retreat — Pool, Views & Proven Short-Term Rental Income. One of the few properties in the Catskills with a private pool and the income to match, this turnkey 4-bedroom, 2-bath mountain retreat on 5+ acres offers a competitive edge that most area listings simply cannot. The private pool extends peak demand well beyond the winter ski season, attracting premium summer

  Ashley O'Malley Listing by Jewett and Jewett LLC

  

  903 Rd, Middletown, NY 12421
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  /13

  $45,000

  • Land
  • 1.4 Acres
  • $32,143 per Acre

  Pocatello Road Pocatello Rd, Middletown, NY 10940

  Country Living. yet just ten minutes to Middletown NY. area of nice homes. over 249 feet county road frontage. no close neighbors private. Rt 17 Rt 24 Rt 35 all close by. for easy commute to work. Orange County is a leader in population and company relocating more jobs Avalible. five minutes to Maple Hill Elementary School zoned R2 with no water and no sewer one would need 3 Acres so this

  John Melchior Howard Hanna Rand Realty

  Pocatello Road Pocatello Rd, Middletown, NY 10940
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  /2

  $26,000

  $1K PRICE DROP

  • Land
  • 1,393 Sq Ft
  • $812,500 per Acre

  138-1/2 Linden Ave, Middletown, NY 10940

  Lot is vacant and directly between 138 & 140 Linden Ave

  Olivia Cappelli Donna Ruffino Realty Corp

  138-1/2 Linden Ave, Middletown, NY 10940
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  /39

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft

  133 Blumel Rd, Middletown, NY 10941

  A Lot of House for the $$! This well maintained 3 BR, 2 Bath home is set back on lovely 1acre grounds with private back yard! Open floor plan! HW floors! C/A. 1 Car attached garage and detached 1 car garage with electric! Gutters have leaf guards! There's a whole house fan and power attic fan! Convenient to shopping and train station!

  Linda Clark Hudson Valley Griffith

  133 Blumel Rd, Middletown, NY 10941
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  /18

  $675,000

  $75K PRICE DROP

  • 8 Beds
  • 3 Baths
  • 3,000 Sq Ft

  21-23 Highland Ave, Middletown, NY 10940

  Kathleen Christopherson EXCLUSIVE SALES AND RENTALS

  21-23 Highland Ave, Middletown, NY 10940
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  /23

  $269,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,091 Sq Ft

  188 Linden Ave, Middletown, NY 10940

  Welcome to this well-maintained ranch offering a practical and comfortable layout. The first floor features a spacious living room filled with natural light, a primary bedroom, plus two additional well-sized bedrooms, and a full bathroom. The lower level offers a large eat-in kitchen with a dedicated dining area, ideal for everyday living and entertaining, along with a spacious basement providing

  Avraham Weinberger Keller Williams Valley Realty

  188 Linden Ave, Middletown, NY 10940
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  /40

  $460,000

  • 3 Beds
  • 2.5 Baths
  • 2,427 Sq Ft

  3 Arden Ct, Middletown, NY 10940

  Welcome to 3 Arden Court, a well-maintained townhouse-style single-family home located on a quiet cul-de-sac in Middletown. Built in 2008, this home offers 3 bedrooms, 2.5 baths, and over 2,400 square feet of living space across three finished levels, providing flexibility for everyday living, working from home, or entertaining. The main level features an open layout with hardwood floors, a

  Justin Jordan Keller Williams Realty

  3 Arden Ct, Middletown, NY 10940
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  /25

  $429,900

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft

  100 Crans Rd, Middletown, NY 10941

  Looking for privacy and land but still close to shopping and restaurants? This is the one you have been waiting for! Remodeled ranch on 10+ acres with 2 bedrooms, bath, LR, DR, kitchen and an office/den on the main floor. Beautiful remodeled kitchen with stainless steel appliances, cherry cabinets and granite counters. Remodeled bath with ceramic tile. Fully finished basement with a family room,

  Darlene Provino Century 21 E & M Williams Rlty

  100 Crans Rd, Middletown, NY 10941
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  /36

  $699,900

  • 4 Beds
  • 2.5 Baths
  • 2,192 Sq Ft

  9 Schoolhouse Rd, Middletown, NY 10940

  Tired of the same predictable new construction colonial? This 2023-built residence offers something far more refined, thoughtfully customized, beautifully maintained, and curated with a level of detail that sets it apart from the expected. Set back down a long private driveway on nearly 3.5 acres, this home makes a striking first impression before you even step inside. The interior unfolds with a

  Nicole Carpenter eXp Realty

  9 Schoolhouse Rd, Middletown, NY 10940
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  /20

  $150,000

  $8K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  529 5th Ave, Middletown, NY 10941

  Fantastic opportunity for a well loved 3 bedroom, 2 bathroom mobile home. Many upgrades AND a Generac Generator as well!!! Granite counters in the kitchen. Windows have all been replaced. Pex plumbing upgrades throughout. Central a/c. Ceiling fans all around the home and many windows for natural light. Primary bedroom has walk in closet and upgraded en-suite bathroom with big closet. Huge closets

  John Nahass Century 21 Full Service Realty

  529 5th Ave, Middletown, NY 10941
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  /4

  $630,000

  • 10 Beds
  • 4 Baths

  309-317 E Main St Unit 309, Middletown, NY 10940

  Welcome to this beautiful two-family home located on E Main Street! Perfect for owner-occupants, investors, or extended family living, this spacious property offers incredible flexibility and charm. One unit features 6 bedrooms, while the second unit offers 4 bedrooms, providing plenty of space for large or multi-generational families. Both units have separate front and side entrances for added

  Betzaida Vericain Q Home Sales

  309-317 E Main St Unit 309, Middletown, NY 10940
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  /8

  $90,000

  • Land
  • 5.37 Acres
  • $16,760 per Acre

  0 Basil Todd Rd, Middletown, NY 12430

  Over five acres of meadow, woods and Mountain View’s to build your dream home. Minutes to Belleayre to enjoy the outdoors. With inventory down, there isn’t any need to settle. We have access to local builders, engineers and contractors to help guide you through the process. Looking for more?? There is an adjacent five acre parcel also available. Seller may be willing to finance too.

  Heather Martin United RE Hudson Valley Edge

  0 Basil Todd Rd, Middletown, NY 12430
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  /16

  $695,000

  • Land
  • 5.07 Acres
  • $137,081 per Acre

  0 Route 28 Unit 20261954, Middletown, NY 12455

  Rare opportunity: PRIME waterfront commercial lot in the heart of Margaretville on State Highway 28 -- unmatched visibility on the busy corridor. Zoned commercial with municipal sewer and water available. The East Branch of the Delaware River parallels the full length of the parcel, providing exceptional waterfront exposure and strong development potential. Seller has detailed plans available

  Katherine Keys The Catskill Dream Team

  0 Route 28 Unit 20261954, Middletown, NY 12455
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  /9

  $1,590,000

  New Construction

  • 4 Beds
  • 4 Baths
  • 5,600 Sq Ft

  375 Blumel Rd, Middletown, NY 10941

  Located at 375 Blumel Road in Scotchtown, New York, this exceptional historic multi-family investment property offers a rare opportunity to own a fully restored income-producing asset in the heart of Orange County in New York's Hudson Valley. Originally constructed in 1787 and completely renovated in 2024, the property combines historic architecture with modern upgrades and strong income

  Keegan Rehill ZORA REI

  375 Blumel Rd, Middletown, NY 10941
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  /50

  $450,000

  • 2 Beds
  • 2.5 Baths
  • 1,814 Sq Ft

  49 Oak Hill Rd, Middletown, NY 10941

  Beautiful Townhome in Prime Location! Welcome to this beautifully maintained townhome offering the perfect blend of comfort, style, and convenience. Ideally located in the sought-after Pine Bush School District, this home is move-in ready and designed for easy living. Featuring 2 spacious bedrooms and 2.5 full baths, this home boasts a bright and open layout with hardwood floors on the main level

  Carla Terranova Keller Williams Realty

  49 Oak Hill Rd, Middletown, NY 10941
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  /2

  $460,000

  $20K PRICE DROP

  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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  /48

  $447,000

  • 4 Beds
  • 2.5 Baths
  • 2,155 Sq Ft

  126 Rolling Meadows Rd, Middletown, NY 10940

  Original owner has loved this ‘must see’ raised ranch in the Meadows for over 45 years, but it is time for someone new to start making memories! Enter into a light-filled interior where hardwood floors run throughout the main floor and the open floor plan invites entertaining. Beautifully renovated kitchen boasts center island for dining, rich wood cabinets, granite countertops, stainless steel

  Laurel Lustgarten Howard Hanna Rand Realty

  126 Rolling Meadows Rd, Middletown, NY 10940
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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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  /47

  $829,000

  • 4 Beds
  • 4 Baths
  • 3,340 Sq Ft

  571 Route 17m, Middletown, NY 10940

  Steeped in character and timeless appeal, this 1930 Colonial invites you in with its striking stone facade and a graceful partial wrap-around porch—an ideal spot to enjoy quiet mornings or unwind at the end of the day. Inside, the home blends classic craftsmanship with modern comfort, featuring rich wooden floors that flow seamlessly throughout the main level.The first floor offers a warm and

  Angela Murphy BHG Real Estate Green Team

  571 Route 17m, Middletown, NY 10940
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  /36

  $589,999

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,350 Sq Ft

  9 Crane Rd, Middletown, NY 10941

  Come see what over 3,000 square feet has to offer! In Middletown, New York where comfort meets charm, and every day feels like home, all you have to do is move in. This home gives a ton of natural light, with a spacious deck off the living room, nestled on a quiet, tree-lined block. Move in and make it your home today. From the moment you enter, natural light pours through every corner,

  Shanese Williams Real Broker NY LLC

  9 Crane Rd, Middletown, NY 10941

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