Homes for Sale near Middletown High School

• 

  

  

  /36

  $349,000

  $30K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,770 Sq Ft

  26 1/2 Ridge St, Middletown, NY 10940

  Beautifully renovated single-family home offering a clean, comfortable layout with thoughtful updates throughout. This residence features 4 spacious bedrooms filled with natural light and a brand-new kitchen equipped with appliances and ample cabinetry. Fresh finishes throughout the home create a bright, move-in-ready feel. Enjoy additional storage space in both the attic and basement, providing

  Cheskel Werzberger Mount Realty

  26 1/2 Ridge St, 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
• 

  

  

  /37

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,246 Sq Ft

  293 Highland Ave Extension, Middletown, NY 10940

  Offering over 1,200 square feet of one-level living, this home still has some of the fun details that made the 1950’s so memorable. A classic Dutch door? Check. Original woodwork? Absolutely. Hardwood floors hiding beneath the carpeting? They’re just waiting to make their comeback. And that fabulous pink-tiled bathroom? We say embrace it! The enclosed porch is another favorite—a cozy little spot

  Patricia Sassi RE/MAX Benchmark Realty Group

  293 Highland Ave Extension, Middletown, NY 10940
• 

  

  

  /50

  $549,999

  • 4 Beds
  • 3.5 Baths
  • 2,298 Sq Ft

  19 Davidge Rd, Middletown, NY 10940

  Welcome to 19 Davidge Road, where luxury, comfort, and functionality come together in one exceptional home. Nestled in the highly sought-after Presidential Heights neighborhood, this impressive 4-bedroom, 4-bathroom residence offers the perfect blend of elegant living spaces and incredible amenities designed for today's lifestyle.From the moment you enter, you'll be captivated by the soaring

  Kevin Grier KW Hudson Valley United

  19 Davidge Rd, Middletown, NY 10940
• 

  

  

  /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
• 

  

  /17

  $320,000

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

  18 Deer Ct Dr Unit Building 19 unit 18, Middletown, NY 10940

  Well-maintained 2-bedroom, 2 bathroom condo in the Deer Run Community with a 53-foot, 3-car garage. Hardwood floors are throughout the open-concept living/dining room. The kitchen features stainless steel appliances. Recently updated washer, dryer (2025) ,water heater (2025), and new windows. Conveniently located on the Dolson Avenue side of Middletown, less than 10 minutes from SUNY Orange

  David Wilson Hudson Premium Realty

  18 Deer Ct Dr Unit Building 19 unit 18, Middletown, NY 10940
• 

  

  /17

  $629,000

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft

  744 Mt Hope Rd, Middletown, NY 10940

  Welcome to this stunning new Colonial home, currently under construction and set on approximately 3 beautiful acres in the desirable Town of Wallkill. Offering approximately 2,600 square feet of finished living space, including a finished basement, this spacious home features 4 bedrooms, 3 full bathrooms, and a one-car garage. The inviting open-concept design showcases gleaming hardwood floors

  Anita S. Cristiano HomeSmart Homes & Estates

  744 Mt Hope Rd, Middletown, NY 10940
• 

  

  /49

  $495,000

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

  58 Cobblestone Ln, Middletown, NY 10940

  Welcome to this beautifully maintained 2,500 sq. ft. townhouse in the desirable Woodside Knolls community. This spacious home offers 3 bedrooms, each featuring a walk-in closet, and 2.5 bathrooms. The open-concept floor plan seamlessly connects the living area and modern kitchen, creating an inviting space for everyday living and entertaining.Additional features include a two-car attached

  Doreen Crowther Howard Hanna Rand Realty

  58 Cobblestone Ln, Middletown, NY 10940
• 

  

  /35

  $399,999

  $15K PRICE DROP

  • 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

  Sheyla Falesto Howard Hanna Rand Realty

  80 Beattie Ave, Middletown, NY 10940
• 

  

  /5

  $335,000

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft

  41 Clinton St, Middletown, NY 10940

  3 Bedroom 1 bath ranch in Middletown! Close to Commuter Highways, Trains & ShoppingSOLD AS-IS SIGHT UNSEEN! CASH ONLY! DO NOT DISTURB OCCUPANTS!!

  Ernie Acampora River Realty Services, Inc.

  41 Clinton St, Middletown, NY 10940
• 

  

  /50

  $419,900

  $10K PRICE DROP

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

  21 Harrison St, Middletown, NY 10940

  Welcome to this well-maintained 4-bedroom, 1.5-bath Victorian home offering a functional layout with numerous updates throughout. A covered front porch welcomes you inside, where the main level features a spacious living room, formal dining room, comfortable family room, updated kitchen, and a convenient half bath. Upstairs, you'll find four bedrooms and a full bathroom, providing a practical

  Jie Liu KW Hudson Valley United

  21 Harrison St, Middletown, NY 10940
• 

  

  /22

  $399,000

  $26K PRICE DROP

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

  19 Putters Way Unit 9, Middletown, NY 10940

  Welcome to a move-ready condo in the desirable Walkill community. This splendid duplex has been 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 bedrooms lend a dramatic vibe for a

  Abraham Lefkowitz Access Realty Team Inc

  19 Putters Way Unit 9, Middletown, NY 10940
• 

  

  /50

  $299,000

  $11K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,398 Sq Ft

  4 Lincoln St, Middletown, NY 10940

  This 3-bedroom, 2-bath Colonial offers 1,398 square feet of comfortable living space on a 0.11-acre lot. Built in 1890, the home blends timeless style with thoughtful upgrades while keeping its original charm. Enjoy bright mornings with natural light, cozy evenings at home, and a neighborhood close to shopping, restaurants, parks, schools, and local services. All utilities are available, making

  Matthew Gibbs KW Hudson Valley United

  4 Lincoln St, Middletown, NY 10940
• 

  

  /19

  $333,000

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  23 Harrison St Unit 25, Middletown, NY 10940

  Come see this well maintained 2 story colonial style home. Centrally located in the City of Middletown which allows you to be minutes away to all the great eateries and to all major shopping and public transportation. The home has taken a few updates over the years. Home has a spacious living room that leads into a formal dining room. Kitchen has plenty of cabinet space as well. The central a.c

  Pedro Garcia Curasi Realty, Inc.

  23 Harrison St Unit 25, Middletown, NY 10940
• 

  

  /33

  $650,000

  $150K PRICE DROP

  • Land
  • 137.3 Acres
  • $4,734 per Acre

  TBD Eatontown Rd, Greenville, NY 10940

  137 Acres of Prime Land in the Town of Greenville – Endless Possibilities 137-acre offering in the Town of Greenville, presenting an exceptional opportunity for future development, subdivision potential, or a private recreational retreat. This expansive parcel features miles of scenic wooded trails ideal for hunting, camping, hiking, horseback riding, four-wheeling, and year-round outdoor

  Joe Distelburger Keller Williams Realty

  TBD Eatontown Rd, Greenville, NY 10940
• 

  

  /3

  $179,900

  • Land
  • 3.15 Acres
  • $57,111 per Acre

  182 Pocatello Rd, Middletown, NY 10940

  Build your dream home on this fully engineered and Town of Wallkill-approved 3+ acre parcel, located within the desirable Middletown School District. This ready-to-build lot offers the perfect combination of privacy and convenience, with a peaceful setting while remaining just minutes from major highways, shopping, dining, and everyday amenities. A rare opportunity to own a fully approved

  Jonathon Lee KW Hudson Valley United

  182 Pocatello Rd, Middletown, NY 10940
• 

  

  /49

  $370,000

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft

  15 Old Anvil Ln, Middletown, NY 10940

  Welcome to 15 Old Anvil Ln, Middletown, a lovingly cared for end unit townhouse in the sought after "The Meadows" community. This unit has been lived in and cared for by the same owners for approximately 40 years. The owner is a builder so he has not skipped on his own improvements and care. The unit offers 3 bedrooms and 2.5 bathrooms, a kitchen and formal dining room with a slider to a

  Valeria Rios KW Hudson Valley United

  15 Old Anvil Ln, Middletown, NY 10940
• 

  

  /33

  $400,000

  • 4 Beds
  • 2 Baths
  • 2,241 Sq Ft

  34 Spring St, Middletown, NY 10940

  Welcome to 34 Spring Street, a spacious multi-family property offering a total of 4 bedrooms and 2 full bathrooms. This versatile home presents an excellent opportunity for investors, owner-occupants, or buyers seeking a flexible living arrangement for extended family. Live in one unit while renting the other, or add both residences to your investment portfolio for potential rental income. Each

  Kerri Stretch Howard Hanna Rand Realty

  34 Spring St, Middletown, NY 10940
• 

  

  /12

  $97,777

  $37K PRICE DROP

  • Land
  • 5,000 Sq Ft
  • $851,716 per Acre

  43 Clinton St, Middletown, NY 10940

  The parcel is shovel-ready with ALL Approvals and ready for you to build. Included in the land sale are the Building Plans, the Survey, the Building Department Approvals for the Building Plan, and the Permit to start building. You are welcome to use your own building plans. Buy "AS-IS". Current Property Owner/Builders can build this house plan for you... OR... your plans. This sale is NOT

  Lena Silk National Veterans Realty Group

  43 Clinton St, Middletown, NY 10940
• 

  

  /10

  $85,000

  • Land
  • 1.9 Acres
  • $44,737 per Acre

  64 Brola Rd, Middletown, NY 10940

  Fantastic opportunity to build a new home within the Minisink school district. Level, 1.9 acre lot featuring frontage on the Little Shawangunk Kill. The location is serene yet in close proximity to your everyday conveniences such as shops, restaurants, parks and much more.

  Nicholas Carbone HomeSmart Homes & Estates

  64 Brola Rd, Middletown, NY 10940
• 

  

  /4

  $129,000

  • Land
  • 3 Acres
  • $43,000 per Acre

  114 Highland Lake Rd, Wallkill, NY 10940

  Discover this scenic 3-acre vacant parcel offering privacy, mature trees, and endless possibilities for recreational use or long-term investment. Buyer to verify all permitted uses with the appropriate municipality.

  Wenpeng Guan KW Hudson Valley United

  114 Highland Lake Rd, Wallkill, NY 10940
• 

  

  /43

  $415,000

  • 4 Beds
  • 2.5 Baths
  • 1,625 Sq Ft

  23 W Conkling Ave, Middletown, NY 10940

  BEAUTIFUL turn-key home located in a quiet neighborhood behind Orange County Community College of MIDDLETOWN! Do NOT let the ouside fool you as this home is bigger than expected... Step inside this Ranch that is in mint condition with the upgrades it offers. Open floor layout from Living room to kitchen. New vinyl floors and recessed lighting throughout. Modern eat-in kitchen with new white

  Sandra Arnez KW Hudson Valley United

  23 W Conkling Ave, Middletown, NY 10940
• 

  

  /32

  $430,000

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

  13 Forest Ave, Middletown, NY 10940

  Fresh updates. New improvements. New opportunity.13 Forest Avenue is officially back on the market after completing repairs and updates, and it's ready for its next owner. This spacious home offers comfortable living, updated features, and a convenient location near schools, shopping, restaurants, and commuter routes. The recent improvements provide added value and confidence for buyers

  Pete Wolven Hudson Valley Home Connection

  13 Forest Ave, Middletown, NY 10940
• 

  

  /35

  $549,000

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

  45 Randall Heights, Middletown, NY 10940

  PRESIDENTIAL HEIGHTS now offers this LUXURY CONTEMPORARY home to make your forever home 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 around blacktopped driveway along with paver stone walkway leads you inside this newly remodeled gem. Discover an incredible blend

  Sandra Arnez KW Hudson Valley United

  45 Randall Heights, Middletown, NY 10940
• 

  

  /19

  $575,000

  • 3 Beds
  • 3 Baths
  • 5,157 Sq Ft

  20 John St, Middletown, NY 10940

  For Sale: Income-Producing Mixed-Use Building in Prime Downtown MiddletownTake advantage of this exceptional opportunity to own a versatile, income-generating property in the heart of Downtown Middletown—an up-and-coming city with a pro-business government and strong growth potential.Property Overview:First Floor:Spacious 2,000 sq. ft. commercial space, currently used

  Jonathon Lee KW Hudson Valley United

  20 John St, Middletown, NY 10940
• 

  

  /21

  $299,900

  Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,884 Sq Ft

  2 S Aspen Rd, Middletown, NY 10940

  Say hello to possibility! A Middletown townhouse with space, flexibility, and room to make it your own. With 3 bedrooms, and a main-level flex space w/ closet, 2.5 bathrooms, plus inviting outdoor space, this home is ready for your personal touch. Close to everything Middletown offers—shops, dining, parks, and commuter routes—this is a smart move with big potential. Make 2 S. Aspen Rd your next

  Derek Greene Greene Realty Group

  2 S Aspen Rd, Middletown, NY 10940
• 

  

  /38

  $399,900

  $20K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,204 Sq Ft

  39 California Ave, Middletown, NY 10940

  More space than meets the eye! This well-maintained 4-bedroom home features two first-floor bedrooms, a first-floor full bath, an enclosed sunroom, a full basement, a detached two-car garage, and a deep, level backyard. Notable improvements include a new roof, gutters, electrical panel, and exterior painting (2024); a new driveway (2023); whole-home updates in 2018 including new flooring

  Guoqing Ouyang Dalton Wade Real Estate Group

  39 California Ave, Middletown, NY 10940
• 

  

  /46

  $450,000

  • 3 Beds
  • 1.5 Baths
  • 1,640 Sq Ft

  21 Manhattan Ave Unit 19, Middletown, NY 10940

  **Opportunities on Manhattan Avenue are few and far between. If you've been waiting for a home in this desirable neighborhood, your wait is over! ** Situated on a beautiful .25-acre lot, this inviting split-level offers the perfect combination of comfort, space, and style with **3 bedrooms, 1.5 baths, a one-car garage, and central air**.From the moment you walk through the door, you'll

  Rosalie Cook Weichert Realtors

  21 Manhattan Ave Unit 19, Middletown, NY 10940
• 

  

  /35

  $329,900

  • 2 Beds
  • 1.5 Baths
  • 1,340 Sq Ft

  50 Sycamore Dr, Middletown, NY 10940

  Welcome to Clemson Park!Discover this beautifully updated and well-maintained townhouse in the desirable Clemson Park community. Featuring 2 bedrooms and 1.5 bathrooms, this home offers a spacious open floor plan perfect for both everyday living and entertaining.The bright living and dining area includes plush, well-maintained carpeted floors and sliding glass doors that open to a

  Maliki Cottrell Cottrell & Associates RE Corp.

  50 Sycamore Dr, Middletown, NY 10940
• 

  

  /36

  $475,000

  Open Thu 5:30PM - 7PM

  • 3 Beds
  • 2.5 Baths
  • 2,257 Sq Ft

  4 Woodrose Ct, Middletown, NY 10940

  Welcome to 4 Woodrose Court, located in the peaceful Highrose Ridge community! Built in 2019, this modern townhome offers a bright, open layout with high ceilings, oversized windows and plenty of natural light.Step inside to hardwood floors throughout the main level and an open-concept kitchen featuring granite countertops, stainless steel appliances, a center island and plenty of space for

  Alyssa Scancarello Howard Hanna Rand Realty

  4 Woodrose Ct, Middletown, NY 10940
• 

  

  /43

  $385,000

  • 3 Beds
  • 2.5 Baths
  • 1,496 Sq Ft

  43 Mayer Dr, Middletown, NY 10940

  Welcome to this three-level townhouse in Middletown with no HOA, offering greater flexibility and no monthly association fees. The main level features a living room with hardwood flooring, a kitchen and dining area, and a half bathroom. The kitchen offers stainless steel appliances and ample cabinet and counter space. Sliding glass doors provide easy access to the rear deck and backyard for

  Wenpeng Guan KW Hudson Valley United

  43 Mayer Dr, Middletown, NY 10940
• 

  

  /39

  $505,000

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

  111 Jasmine Dr, Middletown, NY 10940

  Welcome to Wildflower at Wallkill, one of the Hudson Valley's premier 55+ communities, where beautifully maintained grounds, outstanding amenities, and a true sense of community create an exceptional place to call home. Residents enjoy a beautiful clubhouse, fitness center, business center, indoor and outdoor swimming pools, tennis courts, recreation facilities, gated entry, and professionally

  Christina D'Altilio Coldwell Banker Choice Prop.

  111 Jasmine Dr, Middletown, NY 10940
• 

  

  /20

  $305,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 689 Sq Ft

  15 Anthony St, Middletown, NY 10940

  *Welcome Home!* This exceptional *fully furnished and professionally designed* single-family residence is a rare turnkey opportunity, offering the perfect combination of style, comfort, convenience, and value. Beautifully updated and thoughtfully appointed, this approximately *690+/- sq. ft.* home is ready for immediate enjoyment—simply bring your personal belongings and move right in.The

  Eliezer Salcer Preferred Properties Real Esta

  15 Anthony St, Middletown, NY 10940
• 

  

  /49

  $499,999

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft

  81 Silver Lake Scotchtown Rd Unit 4, Middletown, NY 10940

  Experience modern living in this newly built 3-bedroom, 2.5-bath home designed with comfort and style in mind. Featuring an open floor plan with soaring 10-foot ceilings, this home offers spacious living and entertaining areas filled with natural light. The gourmet kitchen boasts granite countertops, stainless steel appliances, and ample cabinetry, all flowing seamlessly into the main living

  Antoinette Gundersen HomeSmart Homes & Estates

  81 Silver Lake Scotchtown Rd Unit 4, Middletown, NY 10940
• 

  /2

  $395,000

  • 3 Beds
  • 1 Bath

  23 Bonnell St, Middletown, NY 10940

  2 family home in low traffic setting. 1st floor is 3 bedroom @ $1350./month plus utilities 2nd floor is 2 bedroom @ $1100/mo plus utilities Ist floor lease is annual until July 2027. 2nd floor month to month.Old storage building out back. Taxes about $500/mo insurance about $150./mo water about $50./mo

  Mark Tierney Howard Hanna Rand Realty

  23 Bonnell St, Middletown, NY 10940
• 

  

  /21

  $485,000

  • 3 Beds
  • 2.5 Baths
  • 1,781 Sq Ft

  34 Field Stone Dr, Middletown, NY 10940

  Wow! Move right into this beautiful corner unit in Maple Fields offering plenty of living space, 3 bedrooms, 2.5 baths, a finished basement, and a 2-car garage. Features hardwood floors on the main level, a spacious kitchen with granite counters and ample cabinetry, and comfortable bedrooms with large closets and carpeted floors. The laundry is conveniently located upstairs. The finished basement

  Naomi Streicher Q Home Sales

  34 Field Stone Dr, Middletown, NY 10940
• 

  

  /48

  $428,000

  $21K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,041 Sq Ft

  60 Peach Place, Middletown, NY 10940

  Welcome to Swan Village Estates conveniently located just minutes from Highways, stores and shopping. If space is what you need, this three-level , corner lot townhome offers that and more inside and out! The main level features a bright living room with plenty of natural window light followed by a dining area and a spacious eat-in kitchen with stainless steel appliances with plenty of cabinet

  Sandra Arnez KW Hudson Valley United

  60 Peach Place, Middletown, NY 10940
• 

  

  /10

  $299,999

  • Land
  • 27.2 Acres
  • $11,029 per Acre

  328 Bloomingburg Rd, Middletown, NY 10940

  Fully Available!! Vacant Property directly across from Fair Oaks Drive in Movie theater and a gas station with plenty of road frontage!! Minutes to RT17. 27.2 ACRES!!! Electric on road at the front of the property! Possible small farm, Big enough for horses, growing crops, family compound. R2 Zoning.The owner is currently using the property to grow crops and has an Agricultural tax exemption.

  Jeffrey Lyons Curasi Realty, Inc.

  328 Bloomingburg Rd, Middletown, NY 10940
• 

  

  /22

  $328,000

  • 3 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  43 Brick Pond Rd Unit 43, Middletown, NY 10940

  Rare opportunity in the sought-after Spring Hollow community! This very well-maintained 3-bedroom home offers a desirable and hard-to-find layout with 2 full baths and a half bath. Set on an elevated, quiet lot with a south-southeast exposure, the home enjoys beautiful lake views and a peaceful setting. The inviting living area features a wood-burning fireplace, while the updated kitchen offers

  Hai Li KW Hudson Valley United

  43 Brick Pond Rd Unit 43, Middletown, NY 10940
• 

  /2

  $24,500

  $3K PRICE DROP

  • Land
  • 1,393 Sq Ft
  • $765,625 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

Showing Results 41 - 80, Page 2 of 4