Homes for Sale near Middletown High School

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  /25

  $360,000

  • 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
• 

  Explore Middletown High School

• 

  

  

  /24

  $599,000

  • 4 Beds
  • 3 Baths
  • 2,392 Sq Ft

  5 Oak Ridge Rd, Middletown, NY 10940

  Built in 2020, this spacious 2,392 sq ft home offers 4 bedrooms, 3 full bathrooms, and a 2-car garage. The upper level boasts an open-concept layout with vaulted ceilings, a modern kitchen featuring granite countertops and stainless steel appliances, a bright living room, and three bedrooms, including the primary suite, and two full baths. The finished lower level adds even more living space with

  Sandra Laramore Redfin Real Estate

  5 Oak Ridge Rd, Middletown, NY 10940
• 

  

  

  /22

  $699,000

  • 5 Beds
  • 4.5 Baths
  • 3,642 Sq Ft

  14 Lincoln Terrace, Middletown, NY 10940

  Welcome to 14 Lincoln Terrace, a rare 3,642 sq ft, five-bedroom, 4.5-bath residence that embodies luxury, comfort, and smart living. As you enter through the distinctive entry, you’ll notice brand-new Italian marble floors set against brand new warm hardwoods that flow throughout the home. The formal living and dining spaces are light-filled and ideal for entertaining, while a well-appointed

  Chrissa Diakopoulos Bouklis Group Marketing Corp

  14 Lincoln Terrace, Middletown, NY 10940
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  /36

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 2,760 Sq Ft

  214 Phillips St, Middletown, NY 10940

  Welcome to this beautiful newly built 4-bedroom, 3.5-bath home featuring a spacious 2,760 sqft layout across three levels of living space. The gourmet kitchen features an island with a breakfast bar and flows seamlessly into a large dining area. The luxurious primary suite includes a full ensuite bath with dual vanities, a shower, and a separate soaking tub, all highlighted by expansive windows.

  Donna Gray Redfin Real Estate

  214 Phillips St, Middletown, NY 10940
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  /43

  $549,900

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

  21 Cyprus Dr, Middletown, NY 10940

  Welcome to Wildflower at Wallkill—offering easy, one-floor living in one of Orange County’s most sought after 55+ active communities. This well-designed Woodbridge model features two bedrooms and two full baths, along with an open living and dining room combination, while the open kitchen and family room area makes everyday living and entertaining effortless! Enjoy the oversized composite deck,

  Patricia Sassi RE/MAX Benchmark Realty Group

  21 Cyprus Dr, 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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  /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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  /42

  $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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  /21

  $439,900 Open Sat 1PM - 3PM

  • 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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  /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 New windows, a brand-new kitchen with quartz countertops, tiled backsplash, and stainless-steel appliances. Enjoy gleaming hardwood floors, warm fireplace (professionally cleaned) spacious and bright living areas, modern bathrooms, and tasteful finishes throughout. Nothing to do

  Naomi Streicher Q Home Sales

  9 Randall Heights, 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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  /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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  /50

  $499,000

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

  119 Meadow View Dr, Middletown, NY 10940

  Maple Fields Luxury Townhouse – desirable end unit located privately toward the back of the community with its own front entrance. The open-concept main level features a cozy fireplace, perfect for entertaining or relaxing on winter nights. The kitchen offers an island with granite countertops, stainless steel appliances, and custom espresso cabinetry with soft-close drawers. Step out to one of

  Jie Liu Keller Williams Hudson Valley

  119 Meadow View Dr, Middletown, NY 10940
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  /21

  $439,900

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

  16 Leers Rd, Glen Spey, NY 12737

  Beautifully Built in 2025! Nestled in the peaceful woods of the Town of Lumberland, this gorgeous Cape Cod offers the perfect blend of comfort, style, and nature. The open-concept design creates a seamless flow between the living room, kitchen, and dining areas—ideal for entertaining or relaxing at home. The first floor features two spacious bedrooms, a full bath, a convenient laundry room, and

  Chris Ogden Realty Promotions Inc

  16 Leers Rd, Glen Spey, NY 12737
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  /44

  $460,000

  • 3 Beds
  • 2.5 Baths
  • 2,567 Sq Ft

  23 Avoncroft Ln, Middletown, NY 10940

  Welcome to 23 Avoncroft Ln., a stunning 3-bedroom end-unit townhome in the highly sought-after Woodside Knolls community! This beautifully maintained home shines with modern upgrades, including a brand-new stove, microwave, stainless steel appliances, and central AC, ensuring comfort and efficiency. Cozy up by the gas fireplace or enjoy the versatile, fully finished basement with a walkout and a

  Carol Cruz Keller Williams Hudson Valley

  23 Avoncroft Ln, Middletown, NY 10940
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  /21

  $479,900 Pre-Foreclosure

  • 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 generous room for everyday living.The main level features an open floor plan with hardwood floors, a sunlit living room that opens to a private backyard patio, and a dining area

  Jonathon Lee Keller Williams Hudson Valley

  4 Avoncroft Ln, Middletown, NY 10940
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  /2

  $505,000 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 2,996 Sq Ft

  22 Rosecrest Ct, Middletown, NY 10940

  Discover refined living at 22 Rosecrest Court, a nearly 3,000 sq ft designer-inspired townhome blending modern comfort, thoughtful upgrades, and a lifestyle of ease within one of Middletown’s most desirable communities. Crafted in 2015 and meticulously enhanced since, this residence reflects the kind of pride and attention that only comes from true Max Effort living. From the moment you enter,

  Pete Wolven Hudson Valley Home Connection

  22 Rosecrest Ct, Middletown, NY 10940
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  /20

  $249,900

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  193 Schutt Rd, Middletown, NY 10940

  Why rent when you can purchase this updated, move-in-ready 3-bedroom home? This property presents an excellent opportunity for first-time homebuyers, especially with its low taxes. The kitchen features granite countertops, ample cabinet space, stainless steel appliances, and a breakfast bar open to the living room. The spacious living room is filled with natural light, making it a welcoming

  Jeanmarie Valentin HomeSmart Homes & Estates

  193 Schutt Rd, Middletown, NY 10940
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  /6

  $1,550,000

  • 5 Beds
  • 5.5 Baths
  • 4,365 Sq Ft

  79 Bisch Rd, Middletown, NY 10940

  Discover the allure of 89 sprawling acres in Orange County, New York, featuring a charming farm house and a tranquil pond. The farmhouse, with its rustic charm and scenic surroundings, holds immense potential as a delightful Airbnb destination or a mini vacation retreat. Its spacious interior, cozy ambiance, and proximity to nature make it an idea I spot for relaxation and rejuvenation.

  Siang Liu P R O Links Realty Inc

  79 Bisch Rd, Middletown, NY 10940
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  /12

  $268,000

  • 2 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  17 N Aspen Rd, Middletown, NY 10940

  This renovated 2-bedroom, 1.5-bath townhouse in Middletown offers a perfect blend of comfort and convenience! The inviting living room, filled with natural light, leads into a modern kitchen with brand-new stainless steel appliances and an adjacent washer/dryer setup. The dining room features a sliding door that opens up to a private fenced-in backyard—ideal for outdoor relaxation or

  Jonathon Lee Keller Williams Hudson Valley

  17 N Aspen Rd, Middletown, NY 10940
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  /32

  $330,000

  • 3 Beds
  • 1.5 Baths
  • 1,470 Sq Ft

  10 Royce Ave, Middletown, NY 10940

  MIDDLETOWN MAKES AN IDEAL PLACE TO CALL HOME, WITH IT'S VIBRANT DOWNTOWN AND EASY ACCESS TO MAJOR HIGHWAYS AND PUBLIC TRANSPORTATION TO NYC. SITUATED CLOSE TO LOCAL SHOPS, RESTAURANTS & NEARBY PARKS SITS THIS VERY WELL MAINTAINED 3 BEDROOM, 1.5 BATHROOMS, FINISHED ATTIC CHARMING COLONIAL HOME. LOCATED IN A HIGHLY DESIRABLE NEIGHBORHOOD THIS GEM FEATURES A SPACIOUS LAYOUT WITH CLASSIC

  ALISON NIXON eXp Realty

  10 Royce 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, pus close to everything. This is a great starter home or perfect for downsizing. All original hardwood floors, large bathroom and a large rear deck leading to a quiet back yard to play and relax. Brand new hot water heater and newer roof and windows. This home is close to public transportation and stores and restaurants. Original stone fireplace has not been

  Tom Pahucki Keller Williams Realty

  36 Bert Crawford Rd, Middletown, NY 10940
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  /40

  $409,999

  • 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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  /28

  $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
• 

  

  /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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  /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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  /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
• 

  

  /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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  /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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  /43

  $329,000 Open Sat 11AM - 1PM

  • 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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  /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
• 

  

  /41

  $569,000

  • 4 Beds
  • 3 Baths
  • 2,964 Sq Ft

  20 Seaman Rd, Circleville, NY 10919

  Set on 2.3 private acres in Wallkill, Orange County within the Middletown School District, this beautifully maintained 4-bedroom, 3-bath raised ranch offers nearly 3,000 square feet of flexible living space designed for comfort and connection. The open-concept main level features a kitchen with stainless steel appliances, generous counter space, and a natural flow into the dining and living

  Virginia Corbett eXp Realty

  20 Seaman Rd, Circleville, NY 10919
• 

  

  /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
• 

  

  /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
• 

  

  /25

  $399,900

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  56 Mulberry St Unit 54, Middletown, NY 10940

  CALLING ALL INVESTORS! This well-maintained two-family home in the heart of Middletown is a must-see opportunity! Each apartment offers two bedrooms, a spacious living room, a den/office and a full kitchen, perfect for tenants seeking comfort and convenience. Recent updates include a new roof, siding, soffits, and gutters—all completed within the past few months, ensuring peace of mind for years

  Patricia Sassi RE/MAX Benchmark Realty Group

  56 Mulberry St Unit 54, Middletown, NY 10940

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