Middletown, NY Homes for Sale

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  /49

  $350,000 Coming Soon

  • 5 Beds
  • 2.5 Baths
  • 3,581 Sq Ft

  57 Overhill Rd, Middletown, NY 10940

  Discover a rare mid-century contemporary set on just under an acre in Middletown. With more than 3,500 square feet, this 5 bedroom, 2 bath home offers incredible space, soaring ceilings, and floor-to-ceiling windows that fill every corner with natural light. The open, airy layout highlights the home’s architectural character, creating the perfect canvas for a modern makeover. The full basement

  Kewin Garabito eXp Realty

  57 Overhill Rd, Middletown, NY 10940
• Explore Middletown

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  /35

  $999,999

  • 3 Beds
  • 2.5 Baths
  • 3,315 Sq Ft

  535 County Route 22, Middletown, NY 10940

  Looking to Enjoy Life? Experience 535 Ct Rt 22 in the Minisink School District. Unique Handcrafted Home that is surrounded by Nature and Privacy. This Amazing property is backed up to a NYS Protected Conservation in addition to the existing 21 1/2 Acres of Privacy. Gorgeous Breath-taking views can be seen from almost every window of the home. Enjoy the Dramatic, Sundrenched, Eye Popping Open

  John Biasi Howard Hanna Rand Realty

  535 County Route 22, Middletown, NY 10940
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  /33

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  270 Crystal Run Rd, Middletown, NY 10941

  Step into your Middletown New York home that feels ready for you from day one. This move in ready three bedroom two bathroom home offers an easy flow, warm natural light, and the kind of layout that makes everyday living feel calm and effortless. The kitchen is lined with rich wood cabinetry and generous counter space, so cooking, meal prep, and gathering with the people you love feels relaxed

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (329) 209-8831

  270 Crystal Run Rd, Middletown, NY 10941
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  /25

  $360,000 Open Sat 11:30AM - 1PM

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  71 Commonwealth Ave, Middletown, NY 10940

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

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (329) 212-0993

  71 Commonwealth Ave, Middletown, NY 10940
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  /23

  $319,900

  • 2 Beds
  • 1 Bath
  • 836 Sq Ft

  36 Bert Crawford Rd, Middletown, NY 10940

  Cute and cozy and very affordable; plus close to everything. This is a great starter or a downsizing home run. All original hardwood floors, large bathroom and a large rear deck leading to quiet back yard to play and relax. Brand new hot water heater, newer roof and windows, in addition this home has been freshly painted. Situated close to major highways, train station, shopping and restaurants

  Tom Pahucki Keller Williams Realty

  36 Bert Crawford Rd, Middletown, NY 10940
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  /35

  $500,000

  • 3 Beds
  • 2.5 Baths
  • 2,211 Sq Ft

  17 Magnolia Park Rd, Middletown, NY 10940

  Discover easy living in this beautifully maintained 3 bedroom, 2.5 bath townhouse located in the heart of Middletown! Offering three levels of comfortable space, this home features a bright main floor with gleaming hardwood floors, and open living and dining area, and a modern kitchen complete with granite countertops and ample cabinet space. Step outside to your private deck, perfect for morning

  Amy Rossi Howard Hanna Rand Realty

  17 Magnolia Park Rd, Middletown, NY 10940
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  /40

  $409,999 Open Sat 12PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  2729 W Conkling Ave, Middletown, NY 10940

  Welcome to your next home at 29 W Conkling Avenue, located in the heart of Middletown. This charming 3 bedroom ranch-style residence offers many upgrades including updated kitchen with stainless steel appliances, hardwood floors, recessed lighting, solar panels, and a spacious walkout basement that dramatically expands your livable space. Enjoy the level double-lot backyard perfect for relaxing,

  Amanda Rivera Sepulveda Keller Williams Realty

  2729 W Conkling Ave, Middletown, NY 10940
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  /2

  $529,000

  • 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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  /23

  $310,000

  • 2 Beds
  • 2.5 Baths
  • 1,473 Sq Ft

  146 Deer Ct Dr Unit 146, Middletown, NY 10940

  Don't miss out on this this 2-bedroom, 2.5-bath townhouse in the highly desirable Deer Run Condo community in Middletown, NY. This well-kept, two-floor unit features spacious bedrooms, large windows, a master bath, central air, and second floor laundry room. From the living door, you have a sliding glass door out to your Patio, perfect for comfortable living and easy entertaining. Enjoy access to

  Chris Cardinal Keller Williams Realty

  146 Deer Ct Dr Unit 146, Middletown, NY 10940
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  /22

  $279,999

  • 3 Beds
  • 1 Bath
  • 1,340 Sq Ft

  356 Sands Rd, Middletown, NY 10941

  This charming, updated home is an idyllic private retreat on over two acres of wooded land. Move-in ready, the house features fresh paint and new flooring throughout. The cozy living room provides ample natural lighting and leads right into the modern kitchen and dining area. The home offers three comfortable bedrooms and one full bathroom. Step outside to explore your own expansive wooded

  Samantha McCrory Exit Realty Connections

  356 Sands Rd, Middletown, NY 10941
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  /16

  $350,000

  • 3 Beds
  • 2.5 Baths
  • 930 Sq Ft

  65 Monhagen Ave, Middletown, NY 10940

  This beautifully updated Cape Cod–style single-family home offers 3 bedrooms and 2.5 baths, including a generous first-floor primary suite. The main level features a spacious living room with a fireplace, a formal dining room, and an elegant kitchen with granite and wood countertops along with stainless steel appliances. High ceilings, detailed moldings, a full bath, and a convenient laundry area

  Jonathon Lee Keller Williams Hudson Valley

  65 Monhagen Ave, Middletown, NY 10940
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  /26

  $325,000

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

  24 Kent Ct, Middletown, NY 10940

  Elegant 2-Bedroom, 3-Bath End Unit in Sought-After Waters Edge Community Welcome to this beautifully maintained 2-bedroom, 2.5-bath end-unit condo in the desirable Waters Edge community—where comfort meets convenience in a peaceful, lakefront setting. Designed for easy living, this home offers a bright, open layout filled with natural light and modern charm. The first floor features a spacious

  Jonathon Lee Keller Williams Hudson Valley

  24 Kent Ct, Middletown, NY 10940
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  /21

  $230,000

  • 2 Beds
  • 2 Baths
  • 880 Sq Ft

  261 Ruth Ct, Middletown, NY 10940

  Why rent when you can own your own home in the Eagles Point community? This first-floor two-bedroom, two-full-bath condo offers easy living and convenient access to everything Middletown has to offer. Step inside to find a spacious living room with sliding doors that open to your private patio, perfect for relaxing outdoors. The well-equipped kitchen provides ample cabinet space and a comfortable

  Patricia Sassi RE/MAX Benchmark Realty Group

  261 Ruth Ct, Middletown, NY 10940
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  /34

  $650,000

  • 4 Beds
  • 2.5 Baths
  • 2,424 Sq Ft

  235 Maples Rd, Middletown, NY 10940

  This well-maintained spacious Colonial Home is ideally situated on a 2 Acre Lot in the Town of Wallkill Countryside. Lovely Kitchen W/Breakfast Nook overlooks a Large Level Backyard & Private Rear Entertainment Deck. An entry foyer greets you when you arrive at this home, that features a Formal Dining Room, Living Room, Family Room, Powder Room, & mud Room/Laundry to complete the 1st Floor. The

  Shernette Hall VYLLA Home

  235 Maples Rd, Middletown, NY 10940
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  /35

  $625,000

  • 2 Beds
  • 3 Baths
  • 2,975 Sq Ft

  24 Juniper Cir, Middletown, NY 10940

  WELCOME TO WILDFLOWER AT WALLKILL — Orange County's premier 55+ Community! This elegant Tarrington model offers nearly 3,000 square feet of beautifully designed living space, combining comfort, sophistication, and convenience. Inside, you’ll find an open dining and living room combination creates the perfect flow for gatherings, while the expansive kitchen and family room with cathedral ceilings

  Patricia Sassi RE/MAX Benchmark Realty Group

  24 Juniper Cir, Middletown, NY 10940
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  /14

  $341,999

  • 3 Beds
  • 1.5 Baths
  • 1,528 Sq Ft

  21 N Aspen Rd, Middletown, NY 10940

  Move-in ready 3-bedroom, 2-bath townhouse in the Middletown School District. Home features new roof and siding (2023), new windows, and great flooring throughout. No repairs needed! Gas heat (no oil), fenced-in backyard, and covered porch. Delivered vacant at closing. Convenient location near schools, parks, shopping, and major routes. Perfect turnkey property for homeowner or investor!

  Derek Greene Greene Realty Group

  21 N Aspen Rd, Middletown, NY 10940
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  /24

  $215,000

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  326 Concord Ln, Middletown, NY 10940

  Buttonwood Hills Condominiums now offers a 2 bedroom/2 bath unit for your purchase & to call home! A ground level end unit with open floor 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 with a Suite with double closets and a private full

  Sandra Arnez Keller Williams Hudson Valley

  326 Concord Ln, Middletown, NY 10940
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  /21

  $439,900 Open Sat 11AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,736 Sq Ft

  74 Pocatello Rd, Middletown, NY 10940

  Welcome to this bright and spacious 3-bedroom, 2.5-bath high ranch offering comfort, style, and convenience. The main level features an open-concept living and dining room with hardwood floors, high ceilings, and recessed lighting, creating a warm and inviting atmosphere. The modern kitchen provides plenty of cabinet space and is perfect for both everyday meals and entertaining. Down the hall,

  Catherine Eichner Eichner Realty Group Inc.

  74 Pocatello Rd, Middletown, NY 10940
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  /21

  $479,900 Open Sat 1PM - 3PM

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

  4 Avoncroft Ln, Middletown, NY 10940

  Welcome to Woodside Knolls!Step into this bright and spacious 3-bedroom, 2.5-bath townhouse, where comfort and convenience meet modern style. Built in 2009, this 2,427 sq. ft. home with a finished basement offers plenty of space for everyday living. On the main level, enjoy an open floor plan with hardwood floors, a sunny living room that opens to the backyard patio, and a dining area perfect

  Jonathon Lee Keller Williams Hudson Valley

  4 Avoncroft Ln, Middletown, NY 10940
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  /32

  $529,000

  • 3 Beds
  • 2 Baths
  • 1,868 Sq Ft

  9 Randall Heights, Middletown, NY 10940

  Wow! Absolutely stunning, fully renovated 3-bedroom, 2-bath ranch — completely renovated! This beautiful home features a brand-new kitchen with quartz countertops, tiled backsplash, and stainless-steel appliances. Enjoy gleaming hardwood floors, spacious and bright living areas, modern bathrooms, and tasteful finishes throughout. Nothing to do but move right in and start enjoying your new home!

  Naomi Streicher Q Home Sales

  9 Randall Heights, Middletown, NY 10940
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  /15

  $289,000

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

  11 Jordan Ln, Middletown, NY 10940

  Great opportunity for investors for fix and flip.Minimal work needed to make it presentable.Town house located in a beautiful neighborhood.

  Siju John Kerala Realty, LLC

  11 Jordan Ln, Middletown, NY 10940
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  /33

  $450,000

  • 4 Beds
  • 2.5 Baths
  • 2,139 Sq Ft

  10 Scott Dr, Middletown, NY 10941

  Welcome Home! Inviting & Charming Bi-Level Ranch in a Friendly NeighborhoodDiscover the perfect home for your growing family in this beautifully maintained bi-level ranch, ideally situated in a quiet friendly neighborhood within the highly regarded Pine Bush School District.This inviting residence has been thoughtfully updated and features gleaming hardwood floors, new windows, a

  Rudis Rodriguez Keller Williams Realty NYC Grp

  10 Scott Dr, Middletown, NY 10941
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  /22

  $335,000

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft

  98 Watkins Ave, Middletown, NY 10940

  Beautiful Colonial Home located in one of the nicest neighborhoods in all of Middletown. This lovely home features a large sun-drenched Living room a brick Fireplace. Formal Dining Room, Very nice Kitchen with solid wood cabinetry and lots of countertop space. Second level offers a Tiled main bathroom. 3 VerySpacious bedrooms and plenty of closet space. Huge walk-up attic. Enclosed porch.

  John Biasi Howard Hanna Rand Realty

  98 Watkins Ave, Middletown, NY 10940
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  /50

  $620,000

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

  179 Reservoir Rd, Middletown, NY 10940

  Warmth, comfort & space in the Hudson Valley. Welcome home to this spacious Colonial on 2.8 acres offering 3–4 bedrooms, 2 full baths, and a detached 2-car garage with oversized loft. The heart of the home is the large family room — cathedral ceilings, a stunning stone fireplace, and beautiful hardwood floors — the perfect place to gather. The private second-floor primary suite has its own full

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 207-0914

  179 Reservoir Rd, Middletown, NY 10940
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  /33

  $558,000

  • 3 Beds
  • 2.5 Baths
  • 2,108 Sq Ft

  78 Commonwealth Ave, Middletown, NY 10940

  Luxury Post & Beam Contemporary Home with Pool, Gardens & Private Elevator Experience timeless craftsmanship and modern luxury in this exceptional Post & Beam contemporary home. Designed for both comfort and style, this one-of-a-kind property offers warm architectural character, elegant finishes, and thoughtfully designed spaces for everyday living and entertaining. The spacious eat-in kitchen

  Jonathon Lee Keller Williams Hudson Valley

  78 Commonwealth Ave, Middletown, NY 10940
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  /38

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 1,858 Sq Ft

  5 Cobblestone Ln Unit 4301, Middletown, NY 10940

  Welcome to this spacious 3-bedroom, 2.5-bath townhouse located in the desirable Woodside Knolls Community. Built in 2011, this 1,858-square-foot home (plus finished basement) offers a comfortable and functional layout designed for everyday living. The main level features hardwood and carpet flooring, an open dining area, and a bright living room that connects to the backyard patio, creating a

  Virginia Corbett eXp Realty

  5 Cobblestone Ln Unit 4301, Middletown, NY 10940
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  /8

  $100,000

  • 1 Bath
  • 480 Sq Ft

  115 Concord Ln Unit 115, Middletown, NY 10940

  Looking for an affordable and convenient place to call home? This bright studio condo in the desirable Buttonwood Estates community offers comfort and value in one package! Features include a galley-style kitchen, open living/sleeping area, and low-maintenance living—perfect for first-time buyers, downsizers, or investors. Enjoy the benefits of a well-kept community close to shopping, dining, and

  Malik Subhani Weichert Realtors

  115 Concord Ln Unit 115, Middletown, NY 10940
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  /17

  $259,900

  • 2 Beds
  • 2 Baths
  • 1,291 Sq Ft

  118 Deer Ct Dr Unit bldg 5, Middletown, NY 10940

  DEER RUN! Low Taxes! End Unit! 2 Bedrooms! 2 Full Bathrooms! 3 Car Garage! Master Bedroom Suite with Walk In Closet! Over Sized Living Room/Dining Room! Hard Wood Floors! Recessive Lighting! Central Air! Clubhouse! Pool! Close to Major Highways, Buses, Trains & Shopping!

  Amanda Dnistrian ARC Realty 1 in Sales

  118 Deer Ct Dr Unit bldg 5, Middletown, NY 10940
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  /40

  $489,900

  • 3 Beds
  • 2.5 Baths
  • 1,827 Sq Ft

  15 Lindentree Ln, Middletown, NY 10940

  Almost new Townhome in Maples Field is waiting for you! Welcome to our Spacious 3 bedroom, 2.5 bathroom home with 3 levels of space! Enter the open floor plan with hardwood flooring, sun filled living room and dining area. The kitchen features oversized cabinetry with granite countertops, stainless steel appliances and a center island that is perfect for entertaining! Step onto the lovely patio

  Regina Clark Real Estate Circuit Inc

  15 Lindentree Ln, Middletown, NY 10940
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  /15

  $268,000

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

  100 Hillside Dr Unit C1, Middletown, NY 10941

  Charming 2-Bedroom, 2-Bath Home in a Gated Community — Excellent Goshen Schools! Welcome to this bright and inviting first-floor corner condo located in a desirable gated community within the highly rated Goshen School District. This spacious and sunny home offers 2 bedrooms, 2 full bathrooms, wall-to-wall carpeting, and ample closet space throughout. The modern kitchen features new stainless

  Jonathon Lee Keller Williams Hudson Valley

  100 Hillside Dr Unit C1, Middletown, NY 10941
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  /25

  $329,900

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  114 Sarah Ln, Middletown, NY 10941

  WOW! Please check this beautiful end unit townhouse in the town of Wallkill with Goshen school district! This 3 bedrooms and 1.5 bathrooms house has almost everything brand new! New Roof, new flooring in the living room and dining are, new bathrooms, new carpet on the staircase through the hallway and the 3 bedrooms plus new hot water heater and new paved driveway for at least 6 cars! You will be

  Anita S. Cristiano HomeSmart Homes & Estates

  114 Sarah Ln, Middletown, NY 10941
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  /43

  $339,900

  • 4 Beds
  • 2 Baths
  • 1,696 Sq Ft

  28 Spring St, Middletown, NY 10940

  BACK ON MARKET: Your Dream Home Awaits at 28 Spring St, Middletown.Don't let this second chance slip away. This beautiful, 4 bedroom, 2 bathroom home is back on the market. Previous buyer's financing fell through. This is an incredible opportunity for you to step right in and secure a truly remarkable property. The seller has invested in significant updates to make this home move-in ready.

  Leidy Placido Howard Hanna Rand Realty

  28 Spring St, Middletown, NY 10940
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  /5

  $525,000

  • Land
  • 3.8 Acres
  • $138,194 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 Keller Williams Hudson Valley

  TBD Silver Lake-Scotchtown Rd, Middletown, NY 10940
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  /39

  $789,000

  • 4 Beds
  • 2.5 Baths
  • 3,129 Sq Ft

  273 Pine Grove Rd, Middletown, NY 10940

  **** HAS ACCEPTED OFFER ***** ---------COMPLETELY TURN KEY !!!!! -----------RETIRED CUSTOM BUILDERS (husband and wife) - poured their hearts into their family home.--------------GENTLY USED and IMPECCABLY maintained, ----------- It is a WHOLE LOTTA HOUSE and has MANY UPGRADES INCLUDING : ---------- BRAND NEW 30 year ROOF ------------ NEWLY REFINISHED OAK HARDWOOD floors throughout

  Douglas McVicker Suburban Investment Realty

  273 Pine Grove Rd, Middletown, NY 10940
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  /8

  $155,000

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft

  234 Concord Ln, Middletown, NY 10940

  Welcome to this inviting 1-bedroom, 1-bath residence in the heart of Middletown. Featuring an open-living layout with abundant natural light, this unit offers a seamless flow from the living room to the kitchen and plenty of storage. The generously sized bedroom boasts a large closet and easy access to the full bath. Additional perks include in-unit laundry and assigned parking. Located in a

  Malik Subhani Weichert Realtors

  234 Concord Ln, Middletown, NY 10940
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  /44

  $575,000

  • 6 Beds
  • 4 Baths
  • 2,074 Sq Ft

  126 W Main St, Middletown, NY 10940

  STUNNING MIDDLETOWN MULTI-FAMILY is now available for your purchase!! This 2-family Colonial is in turn-key condition and offers all the space that you need with nothing left to do but unpack. Ideal for an extended family or allow the rental income of the other unit pay your mortgage! The main home consists of 3 bedrooms, one being a 1st level Suite with a private bath. A 3 bedroom, 2.5 bath with

  Sandra Arnez Keller Williams Hudson Valley

  126 W Main St, Middletown, NY 10940
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  /26

  $250,000

  • 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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  /15

  $649,999

  • 4 Beds
  • 2.5 Baths
  • 2,410 Sq Ft

  217 Schoolhouse Rd, Middletown, NY 10940

  Experience the perfect blend of modern luxury and peaceful country living with this like-new colonial, built in 2022 and set on a spacious 2-acre lot in the desirable Minisink School District. Step inside to discover a thoughtfully designed, open-concept main level, where gleaming hardwood floors guide you through a bright and airy layout. A cozy fireplace anchors the living area, creating an

  Nerette Lewis RE/MAX Town & Country

  217 Schoolhouse Rd, Middletown, NY 10940
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  /14

  $315,000

  • 3 Beds
  • 1 Bath
  • 1,058 Sq Ft

  14 Pennsylvania Ave, Middletown, NY 10940

  Welcome to 14 Pennsylvania Avenue — a 3-bedroom, 1-bath ranch in the Minisink Valley School District offering convenient one-level living in a peaceful neighborhood setting. This solid home sits on a spacious 0.33-acre lot with a large, fenced-in backyard perfect for pets, play, or garden space. With good bones and a practical floor plan, it’s the perfect opportunity to bring your own style and

  Dominick Tufano RE/MAX Benchmark Realty Group

  14 Pennsylvania Ave, Middletown, NY 10940
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  /26

  $230,000

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  376 Concord Ln, Middletown, NY 10940

  Buttonwood In Middletown now offers a 2 bedroom/2 bath for you to call home! An updated unit with vinyl floors throughout, updated kitchen, stainless steel appliances & plenty of cabinet space. Open floor layout living Room/dinning room. Newer washer & dryer inside the unit for your convenience. Spacious bedrooms, one of them being a Suite with a private full bath and a walk in closet. Both

  Sandra Arnez Keller Williams Hudson Valley

  376 Concord Ln, Middletown, NY 10940

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