Middletown, NY Homes for Sale

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  /49

  $799,000

  • 5 Beds
  • 4.5 Baths
  • 4,085 Sq Ft

  3 Truman Ct, Middletown, NY 10940

  Step into refined living with this beautifully maintained 5-bedroom Colonial-style home, where classic charm meets upscale upgrades. From the moment you enter, you’re welcomed by exquisite craftsmanship, including detailed crown molding and rich hardwood floors that flow seamlessly throughout the main living spaces.This spacious residence features three elegant fireplaces, creating warm and

  Dominick Tufano RE/MAX Benchmark Realty Group

  3 Truman Ct, Middletown, NY 10940
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  /28

  $434,999

  • 3 Beds
  • 2 Baths
  • 1,614 Sq Ft

  9 Chestnut St, Middletown, NY 10940

  Move in ready Colonial that perfectly balances classic charm with tasteful updates. This home has been meticulously maintained and features a bright, inviting interior. The kitchen serves as the heart of the home, updated with white shaker cabinets, granite countertops, an oversized island, and a full suite of stainless steel appliances. For added convenience, the first floor includes a dedicated

  Christian Lugo Howard Hanna Rand Realty

  9 Chestnut St, Middletown, NY 10940
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  /17

  $429,000

  $30K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,097 Sq Ft

  4 Kless Ct, Middletown, NY 10940

  Welcome to this well-kept 3-bedroom home with a bonus loft, set in the Maple Fields community. The first floor offers an easy, open layout with a comfortable living area that leads out to a private patio, along with a dining space and a kitchen that includes a pantry, tile accents, and stainless steel appliances. Upstairs you’ll find the primary bedroom featuring a walk-in closet and its own

  Bryant Moran YourHomeSold Guaranteed Realty

  4 Kless Ct, Middletown, NY 10940
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  /50

  $399,000

  • 3 Beds
  • 1.5 Baths
  • 1,446 Sq Ft

  4 Saint Eve Ct, Middletown, NY 10940

  Situated on a quiet cul-de-sac, this spacious and versatile home offers the perfect blend of comfort, convenience, and flexibility. Enjoy a large yard ideal for entertaining, complete with a deck and patio for outdoor gatherings and relaxation. Inside, the home features ample parking, 3-zone heating for year-round comfort, and an all-inclusive room/office perfect for working from home, guests, or

  Robin Cohen Keller Williams Realty

  4 Saint Eve Ct, Middletown, NY 10940
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  /41

  $479,000

  • 3 Beds
  • 2.5 Baths
  • 2,228 Sq Ft

  217-219 Highland Ave, Middletown, NY 10940

  Spacious and charming 3-bedroom, 2.5-bath home featuring a welcoming wraparound porch and an abundance of living space throughout. The main level offers an entry foyer, living room, formal dining room, kitchen, family room, den, powder room, and laundry room. Upstairs features a primary bedroom with private bath, two additional bedrooms, and a full hall bathroom. The walk-up third level offers

  Wenpeng Guan KW Hudson Valley Untied

  217-219 Highland Ave, Middletown, NY 10940
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  /4

  $1,650,000

  • Land
  • 7.5 Acres
  • $220,000 per Acre

  32 Gibbs Ct, Middletown, NY 10940

  32 Gibbs Court | Wallkill, NYPrime 3.20 Acre Commercial Development PAD on 7.5-acre lot Opportunity in the Heart of WallkillUnlock the full potential of this premier 3.20 PAD on a 7.5-acre commercial parcel, ideally located in the thriving Town of Wallkill. Situated within the highly desirable Town Center District, 32 Gibbs Court offers a rare development opportunity with broad zoning

  Peter Janis Berkshire Hathaway HS NE Prop.

  32 Gibbs Ct, Middletown, NY 10940
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  /47

  $349,999

  • 3 Beds
  • 4 Baths
  • 1,854 Sq Ft

  36 Prospect St, Middletown, NY 10940

  This beautiful colonial-style home is in need of some TLC! Due to its status as a Short Sale, the property is being sold “As-Is” with subject approval from a third party. This charming property boasts four bedrooms, two full baths, a well-equipped kitchen, a formal dining and living room, an unfinished basement and attic, a private driveway, and a spacious lot. Whether you’re an investor or a

  Vladimir Charles-Pierre Our Community Realty Ltd

  36 Prospect St, Middletown, NY 10940
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  /42

  $649,000

  $30K PRICE DROP

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

  481 Dosen Rd, Middletown, NY 10940

  ABSOLUTELY GORGEOUS!!! MUST SEE!! QUALITY BUILT WITH BRAND NEW ADDITION AND BRAND NEW DETACHED POLE BARN!!! OVER 7 ACRES !!! 481 Dosen Road offers a rare combination of quality construction, privacy, and usable space, set on 7.4 peaceful acres. This custom-built Lok-N-Logs log home was thoughtfully designed to blend the character of a true log cabin with the comforts needed for everyday living.

  Frank Muccari Cronin & Company Real Estate

  481 Dosen Rd, Middletown, NY 10940
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  /25

  $579,990

  • 3 Beds
  • 2.5 Baths
  • 2,205 Sq Ft

  30 Daly Rd, Middletown, NY 10940

  New Construction. This 3-bedroom, 2.5-bath colonial is situated on a 2-acre level/partially wooded lot. The first floor offers an oversized living room, dining room, a kitchen with granite countertops and stainless appliances, and sliders leading to a backyard deck. Also on the first floor, you'll find a den/study, a laundry room, and a good-sized 1/2 bath. The second floor features a large loft

  Jonathon Lee KW Hudson Valley Untied

  30 Daly Rd, Middletown, NY 10940
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  /39

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 2,053 Sq Ft

  45 Randall Heights, Middletown, NY 10940

  PRESIDENTIAL HEIGHTS welcomes you to make this LUXURY CONTEMPORARY home yours today! Set in the highly desirable Presidential Heights neighborhood, known for its beautiful homes, peaceful atmosphere, and close proximity to everyday essentials. A large wrap araund blacktopped driveway along with paver stone walkway leads you inside this newly remodeled gem. Discover an incredible blend of space,

  Sandra Arnez KW Hudson Valley Untied

  45 Randall Heights, Middletown, NY 10940
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  /18

  $499,000

  • 4 Beds
  • 2 Baths
  • 1,932 Sq Ft

  12 Walnut Ln, Middletown, NY 10940

  Beautifully maintained home in a desirable Middletown neighborhood featuring a bright, functional layout and a spacious backyard. One of the most valuable features of this property is its flexible bedroom layout. Four total bedrooms, including two conveniently located on the first floor, offering rare flexibility for multi-generational living, guests, a home office, or easy single-level living.

  Xiaohui Cui KW Hudson Valley Untied

  12 Walnut Ln, Middletown, NY 10940
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  /36

  $485,000

  • 3 Beds
  • 2.5 Baths
  • 2,084 Sq Ft

  1 High Ridge Ln, Middletown, NY 10940

  Welcome to refined, low maintenance living in one of Middletown’s most sought after gated communities. This beautifully maintained end unit townhouse offers the perfect balance of space, comfort, and convenience, with over 2,000 square feet of living space designed for today’slifestyle. Step inside to find a bright and inviting layout featuring spacious bedrooms each with generous closet

  Jason Madison eXp Realty

  1 High Ridge Ln, Middletown, NY 10940
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  /30

  $450,000

  • 5 Beds
  • 3 Baths

  37 Monhagen Ave, Middletown, NY 10940

  Welcome to an opportunity that is becoming harder and harder to find. This multi-family property sits on a nearly half-acre lot in the City of Middletown and offers investors, contractors, and ambitious buyers the chance to create significant value. With 2,151 square feet, five bedrooms, three full bathrooms, and income-producing potential, this is the type of property that rewards vision and

  Isaiah Lopez KW Hudson Valley Untied

  37 Monhagen Ave, Middletown, NY 10940
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  /32

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 2,929 Sq Ft

  1 Parkview Dr, Middletown, NY 10940

  Welcome to 1 Parkview Dr. in beautiful Presidential Park in Middletown, NY. Located on a corner lot, this expanded raised ranch shines. Gleaming hardwood floors and spacious room size are only some if it's great features. Eat in kitchen boasts an atrium that looks out to its lovely landscaped backyard. Spend time in this space and you'll feel like you're on vacation. Beautiful inground pool is

  Marie Altieri Howard Hanna Rand Realty

  1 Parkview Dr, Middletown, NY 10940
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  /36

  $599,900

  • 6 Beds
  • 3.5 Baths
  • 2,948 Sq Ft

  669 Mountain Rd, Middletown, NY 10940

  Country Escape of 6 spacious bedrooms offers space, privacy, and a serene setting on 3.38 acres. Just about 75 miles from New York City, it’s close enough for convenient weekend escapes yet far enough to feel like a true retreat feels like a private estate—perfect for those seeking a refined escape from city life A grand foyer opens to a bright, airy layout with high ceilings, large windows, and

  Michelle Gruberger Real Estate Circuit Inc

  669 Mountain Rd, Middletown, NY 10940
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  /48

  $849,900

  • 4 Beds
  • 4 Baths
  • 3,699 Sq Ft

  21 Lincoln Terrace Unit 19, Middletown, NY 10940

  A rare opportunity to own an architectural masterpiece designed and personally occupied by renowned local architect Dennis Jurow. Privately nestled on a beautifully wooded one-acre setting in Middletown, this iconic mid-century modern residence offers over 4,000 square feet of thoughtfully curated living space where architecture, art, and nature exist in perfect harmony. From the moment you

  Patricia Sassi RE/MAX Benchmark Realty Group

  21 Lincoln Terrace Unit 19, Middletown, NY 10940
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  /32

  $279,000

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  19 Hulse Ave, Middletown, NY 10940

  Opportunities like this don't come around often! Welcome to 19 Hulse Avenue, a charming and updated ranch offering the perfect combination of comfort, convenience, and value. Featuring 2 bedrooms, 1 full bath, plus a versatile loft space perfect for a home office, guest area, playroom, or extra storage, this home is ready for its next chapter! Step inside to find updated vinyl flooring

  Juan Bautista Serhant LLC

  19 Hulse Ave, Middletown, NY 10940
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  /30

  $844,000

  $5K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 3,764 Sq Ft

  238 S Centerville Rd, Middletown, NY 10940

  Spacious Country Retreat on 22.6 Acres in Minisink Valley School District This exceptional property offers privacy, comfort, and extensive amenities set on 22.6 picturesque acres. The master bedroom and bathroom were updated in 2016, complemented by a wet bar in the family room—perfect for entertaining. The home features three fireplaces and a wood stove, creating warmth and character throughout.

  Linda VanDeWeert BHG Real Estate Green Team

  238 S Centerville Rd, Middletown, NY 10940
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  /26

  $134,999

  $15K PRICE DROP

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

  79 Stern Scenic Dr, Middletown, NY 10940

  Welcome to this updated 3-bedroom, 2-bath double-wide mobile home offering comfort, space, and convenience in Middletown. Recent updates enhance both style and functionality, while the open and spacious layout provides plenty of room to relax or entertain. The primary bedroom features a private bath, and the additional bedrooms are generously sized. Conveniently located near local shopping,

  Ivan Carvalho Exit Realty Connections

  79 Stern Scenic Dr, Middletown, NY 10940
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  /15

  $95,000

  $10K PRICE DROP

  • Land
  • 5.1 Acres
  • $18,627 per Acre

  Lot 11 Meadow Brook Dr, Middletown, NY 12455

  Tucked away in the pastoral rolling hills, just a short drive from down town Margaretville, this very special 5 acre parcel is sure to check many boxes on your wish list. A peaceful and serene setting with beautiful scenic views and rolling open meadows backed by magical woods to explore. With several possible building sites this parcels offers what most are looking for. Easy access, and close to

  Rosalie Glauser Listing by Frank Lumia Real Estate Plus!, LLC

  

  Lot 11 Meadow Brook Dr, Middletown, NY 12455
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  /12

  $280,250

  $15K PRICE DROP

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

  2 Durham Ct Unit 82, Middletown, NY 10940

  A Rare Find Just Got Better with a price improvement. Finding a place that balances a peaceful nature retreat with the reality of needing everyday essentials and good takeout close by is a rare find. Enter Waters Edge, Middletown’s premier condo community right on Silver Lake. This large end-unit townhome gives you all the perks of homeownership with none of the weekend-ruining yard work, meaning

  Melissa Terman River Realty Services, Inc.

  2 Durham Ct Unit 82, Middletown, NY 10940
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  /2

  $55,000

  $10K PRICE DROP

  • Land
  • 10,454 Sq Ft
  • $229,167 per Acre

  1 S Shore Dr, Middletown, NY 10940

  Quarter acre waterfront parcel located on Pocatello Lake. Scenic water views, and a peaceful setting with convenient access to local amenities in the City of Middletown and Town of Wallkill. Rare opportunity for lakefront land ownership in a desirable location.

  Soleil Jackman Howard Hanna Rand Realty

  1 S Shore Dr, Middletown, NY 10940
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  /9

  $399,900

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

  25 Mill St, Middletown, NY 10940

  Completely renovated two-unit property with Residential/CMU zoning. Ideal opportunity for an owner-user or investor — operate your business on the first floor while generating rental income from the occupied second-floor unit. Property includes 2 car parking/off-street parking, with potential for expansion subject to city approvals.

  Sammy Zambrano Keller Williams Realty

  25 Mill St, Middletown, NY 10940
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  /5

  $399,000

  $126K PRICE DROP

  • Land
  • 3.8 Acres
  • $105,028 per Acre

  TBD Silver Lake-Scotchtown Rd, Middletown, NY 10940

  Attention Builders and Developers: Presenting a rare, fully-approved 3-lot subdivision on Silverlake Scotchtown Road in the desirable Town of Wallkill, ready for the construction of three new two-family homes. Each lot is designed to accomodate a 32x80 structure which is large enough for each unit to include 3 bedrooms, 2 baths and a 1 car garage. Seller does not have architectural plans so

  Jason McGovern KW Hudson Valley Untied

  TBD Silver Lake-Scotchtown Rd, Middletown, NY 10940
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  /26

  $199,000

  $51K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 360 Sq Ft

  51 S Shore Dr, Middletown, NY 10940

  Welcome to 51 S Shore Drive, a charming and thoughtfully updated bungalow retreat nestled on a private, wooded 9,374 sq ft lot with sparkling lake views in scenic Middletown, NY. This beautifully curated 1-bedroom, 1-bath lakefront getaway offers 360 square feet of smart, stylish living space perfect for a weekend escape, vacation rental, or year-round peaceful living. Step inside to a crisp,

  Arya Rabinovits eRealty Advisors, Inc

  51 S Shore Dr, Middletown, NY 10940
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  /31

  $489,999

  Open Sat 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,832 Sq Ft

  20 Tammy Dr, Middletown, NY 10941

  LOCATION,LOCATION,LOCATION CLOSE TO WALMART THE METRO NORTH TRAIN STATION TO NYC, Abundance of Dining and Grocery options, The Galleria Mall, Garnet Medical Center, Major Highways Route 17M & Interstate I84, Home has 3 bedrooms and 2.5 bathrooms, Stainless Steel Appliances, Granite counter top with a breakfast nook., Hardwood Floor, En-suite bathroom in master bedroom, Large deck on upper level

  Sol Perry BHG Real Estate Green Team

  20 Tammy Dr, Middletown, NY 10941
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  /42

  $369,900

  • 3 Beds
  • 1.5 Baths
  • 1,366 Sq Ft

  41 Beers Dr, Middletown, NY 10940

  This sleepy little charmer is ready for you to put your own stamp on it. Great 3-bedroom, 1-1/2 bath, split-ranch home with hardwood floors existing throughout. You can move in today and make renovations as you see fit or not! It's up to you. This home offers a great size back yard and large back deck for Sunday BBQ's. Too hot outside? No worries the central air is on! Cozy family room located on

  Dien Le Duc Hudson Premium Realty

  41 Beers Dr, Middletown, NY 10940
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  /33

  $649,000

  $26K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,481 Sq Ft

  5 Decker Dr, Middletown, NY 10940

  Charming Farmhouse Retreat on 2.9 Acres! Nestled on a quiet country road in the Town of Greenville and located within the desirable Minisink Valley Central School District. This beautiful farmhouse-style home offers the perfect blend of comfort, charm, and country living. Inviting home features 3 bedrooms and 2.5 baths with attractive Pergo wood flooring throughout the downstairs, while upstairs

  Dominick Tufano RE/MAX Benchmark Realty Group

  5 Decker Dr, Middletown, NY 10940
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  /27

  $185,000

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  326 Concord Ln, Middletown, NY 10940

  PRICED TO SELL!!! Buttonwood Hills Condominiums now offers a 2 bedroom/2 bath unit for your purchase. Add your final touches and make it yours! A ground level end unit with open floor plan from living room to dining room with sliders that lead to a seating area where you can enjoy the outdoors. Beautiful kitchen with stainless steel appliances & plenty of cabinet space. Spacious bedrooms, one

  Sandra Arnez KW Hudson Valley Untied

  326 Concord Ln, Middletown, NY 10940
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  /40

  $449,999

  $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,055 Sq Ft

  12 Weather Vane Way, Middletown, NY 10940

  Nestled in the Rolling Meadows residential community in the Middletown School District, this 3-bedroom, 2.5-bathroom raised ranch bilevel home seamlessly blends absolute convenience with comfortable community living. The location is truly key, positioned just off East Main Street for incredibly quick access to major highways like Interstate 84 and Route 17, placing you less than 10 minutes from

  Ray Reyes Keller Williams Realty

  12 Weather Vane Way, Middletown, NY 10940
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  /35

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,577 Sq Ft

  153 Ridgewood Ave Unit 155, Middletown, NY 10940

  Welcome to 153 Ridgewood, a stunning 2022 built ranch style home that delivers the kind of single level living buyers dream about. From the moment you step inside, the vaulted ceilings, open concept layout, modern finishes, and natural flow of the home create an immediate “this is the one” feeling. With over 1,500 square feet of beautifully designed space, this home offers the rare combination of

  Isaiah Lopez KW Hudson Valley Untied

  153 Ridgewood Ave Unit 155, Middletown, NY 10940
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  /49

  $589,900

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

  311 New Vernon Rd, Middletown, NY 10940

  Nestled well off the road amid mature landscaping and expansive lawn, this custom Colonial offers a rare combination of privacy, space, and pride of ownership. Built and meticulously maintained by its original owners, the home reflects years of thoughtful updates and careful stewardship. Inside, hardwood floors extend throughout the home, creating warmth and continuity from room to room. Custom

  Patricia Sassi RE/MAX Benchmark Realty Group

  311 New Vernon Rd, Middletown, NY 10940
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  /13

  $275,000

  • 2 Beds
  • 2.5 Baths
  • 1,348 Sq Ft

  11 Jordan Ln, Middletown, NY 10940

  Welcome to 11 Jordan Lane, Middletown, NY. This 2-bedroom, 2-bathroom condo offers a practical floor plan and a convenient location close to shopping, dining, schools, healthcare facilities, and major commuter routes.With strong potential and a desirable location, the property presents an excellent opportunity for investors seeking immediate rental income or buyers looking to add value

  Richu Saj Kerala Realty, LLC

  11 Jordan Ln, Middletown, NY 10940
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  /50

  $899,000

  $40K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,894 Sq Ft

  114 Last Rd, Middletown, NY 10941

  Distinctive 11-Acre Country Retreat - More than a home, this property delivers a lifestyle defined by space, privacy, and ease. Set across two parcels totaling 11.1 acres, this distinctive Cape Cod combines thoughtful design and easy, everyday living. From the expansive covered front porch to the farmhouse-style entry, the home immediately feels airy and inviting. Inside, the home balances warmth

  Michelle Genatempo Howard Hanna Rand Realty

  114 Last Rd, Middletown, NY 10941
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  /35

  $415,000

  • 3 Beds
  • 1 Bath
  • 1,032 Sq Ft

  80 Beattie Ave, Middletown, NY 10940

  Welcome Home to Comfort, Style & Convenience in the Heart of Middletown! This beautifully renovated two-story Colonial blends timeless charm with modern updates, offering the perfect place to call home. Featuring 3 bedrooms, 1 full bathroom, and thoughtfully designed living spaces throughout, this move-in-ready property has been updated to maximize both functionality and style. From the moment

  Sheyla Falesto Howard Hanna Rand Realty

  80 Beattie Ave, Middletown, NY 10940
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  /17

  $515,000

  • 4 Beds
  • 3 Baths
  • 2,484 Sq Ft

  86 Maples Rd, Middletown, NY 10940

  Beautiful Raised Ranch in Middletown, NY This stunning home features 4 spacious bedrooms and 3 full bathrooms, offering comfort, style, and plenty of space for living and entertaining. The kitchen showcases gorgeous marble countertops and detailed custom cabinetry that truly stand out. The living room boasts vaulted ceilings and a large picture window that fills the space with natural light and

  Delease Jenkins RE/MAX Town & Country

  86 Maples Rd, Middletown, NY 10940
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  /21

  $369,900

  • 4 Beds
  • 1.5 Baths
  • 1,602 Sq Ft

  15 Scotchtown Place, Middletown, NY 10941

  Welcome to this Charming, 4 bedroom 1 1/2 bath Cape style home, offering 1602 sq ft of comfortable living space. This well-laid-out residence features four bedrooms and 1 and 1/2 th bathrooms, perfect for flexible living arrangements. Hardwood floors lie beneath the carpeting in the living room, and bedrooms, ready to be restored to their original beauty. The bright living room features a cozy

  Brian Schofield DiMatteo Realty LLC

  15 Scotchtown Place, Middletown, NY 10941
• 

  

  /22

  $409,500

  $16K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,337 Sq Ft

  19 Putters Way Unit 9, Middletown, NY 10940

  Welcome to this fully updated, move-ready condo in the desirable Walkill community. This splendid duplex has been luxuriously upgraded with modern paint tones and the latest finishes. Bright and sunny rooms with updated lighting throughout. The kitchen boasts sleek, brand-new appliances and classic wood cabinetry. The bathrooms have been meticulously maintained. Cathedral ceilings in both

  Abraham Lefkowitz Access Realty Team Inc

  19 Putters Way Unit 9, Middletown, NY 10940
• 

  

  /23

  $399,999

  • 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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  /18

  $55,000

  • Land
  • 5.26 Acres
  • $10,456 per Acre

  0 Joe Todd Rd Unit R1680388, Middletown, NY 10940

  Near the end of a quiet town-maintained dead-end road, you’ll find this ideal building lot in the town of Fleischmanns. This parcel has a mix of evergreens, deciduous trees, open clearings, and a seasonal stream, most of which is on level terrain ideal for a driveway and building site. Enjoy the peace and tranquility of a wooded sanctuary just minutes up the hill from the happening main street of

  Peter Kleeman Listing by Jewett and Jewett LLC

  

  0 Joe Todd Rd Unit R1680388, Middletown, NY 10940

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