Homes for Sale near Middletown High School

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  /50

  $568,000 Open Sun 11AM - 2PM

  • 7 Beds
  • 4.5 Baths
  • 3,592 Sq Ft

  104-108 Highland Ave, Middletown, NY 10940

  Historic Elegance Meets Modern-Day Convenience in this circa 1860 home in the heart of Middletown, NY. Pristinely positioned back from the road, set on just shy of an acre, this historic gem offers 3500+ square feet of timeless character and space. From the moment you enter, soaring ceilings, rich hardwood floors, built-ins and detailed crown molding set the tone. The expansive dining room,

  

  JoAnn Maxwell

  Howard Hanna Rand Realty

  (329) 210-1132

  104-108 Highland Ave, Middletown, NY 10940
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  Explore Middletown High School

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  /48

  $483,900

  • 3 Beds
  • 3.5 Baths
  • 2,521 Sq Ft

  53 Cornwall Ln, Middletown, NY 10940

  Beautifully renovated 3-bedroom, 3.5-bathroom townhouse with a 2-car garage, located in the highly desirable Woodside Knolls community. This spacious home offers modern updates throughout, providing comfort, style, and functionality for today’s living. Conveniently situated just minutes from the Garnet Health Medical Center, Galleria Mall, Metro-North, shops, supermarkets, and major highways,

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 217-0628

  53 Cornwall Ln, Middletown, NY 10940
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  /2

  $175,000

  • 1 Bed
  • 1 Bath
  • 784 Sq Ft

  45 Knapp Ave, Middletown, NY 10940

  Attention investors! This is a true “what you see is what you get” opportunity. Bring your tools and imagination and transform this property into a valuable addition to your rental portfolio. Perfect for investors seeking potential and long-term returns. Cash buyer or rehab loan needed.

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 210-1290

  45 Knapp Ave, Middletown, NY 10940
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  /2

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,620 Sq Ft

  46 Knapp Ave, Middletown, NY 10940

  This oldie but goodie is full of potential! With a little love, fresh paint, and imagination, this home can truly shine as a wonderful starter home. It also presents a great opportunity for investors looking to expand their rental portfolio, long-term tenants would love the option to stay. Features include some hardwood floors, a detached 2-car garage, and a recently paved blacktop driveway.

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 209-9787

  46 Knapp Ave, Middletown, NY 10940
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  /46

  $489,000

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

  59 Woodside Knolls Dr, Middletown, NY 10940

  Welcome home to this impeccably maintained, tri-level townhouse nestled in the heart of the scenic Hudson Valley. Boasting over 2,400 sq. ft. of modern living space, this home features 9' ceilings, gleaming hardwood floors, and an open layout. The kitchen shines with countertops, stainless steel appliances, and a charming breakfast area. Retreat to the spacious primary suite with a walk-in closet

  

  Donna Reese

  Keller Williams Hudson Valley

  (329) 209-9797

  59 Woodside Knolls Dr, Middletown, NY 10940
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  /33

  $499,000 Open Sat 1:30PM - 3:30PM

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

  60 Magnolia Park Rd, Middletown, NY 10940

  Beautifully cared-for 3 bedroom, 2.5-bath townhouse in the heart of Middletown! Spanning three levels, this home offers comfortable, versatile living with hardwood floors throughout both the main and second levels. The bright main floor features an open-concept living area featuring a fireplace, a dining area, along with a modern kitchen complete with granite countertops and ample cabinet space.

  Sandra Laramore Redfin Real Estate

  60 Magnolia Park Rd, Middletown, NY 10940
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  /35

  $499,900

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

  19 Sunflower St, Middletown, NY 10940

  Welcome to easy, carefree living in the highly sought-after 55+ community of Wildflower at Wallkill. This beautifully maintained two-bedroom ranch offers the perfect blend of comfort, style, and convenience, all set within a vibrant, amenity-rich neighborhood. This home has been meticulously cared for, including fresh paint and new carpeting, ensuring a move-in-ready experience. Step inside to

  Patricia Sassi RE/MAX Benchmark Realty Group

  19 Sunflower St, Middletown, NY 10940
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  /50

  $615,000

  • 3 Beds
  • 2.5 Baths
  • 3,013 Sq Ft

  38 Putters Way, Middletown, NY 10940

  Well-maintained 3-bedroom, 2.5-bath townhome with a finished basement in the gated community of The Fairways, set alongside a golf course and conveniently located near major highways, Garnet Health Medical Center, shopping, and dining. The main level features hardwood flooring and an open layout connecting the kitchen, dining, and living areas with a gas fireplace. The kitchen includes a

  Jie Liu Keller Williams Hudson Valley

  38 Putters Way, Middletown, NY 10940
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  /26

  $319,000

  • 3 Beds
  • 1.5 Baths
  • 1,484 Sq Ft

  15 Rivervale Rd, Middletown, NY 10940

  Welcome to this 3-bedroom, 1.5-bath townhouse. The main level features a kitchen with a refrigerator updated in 2023, along with a dining area and living room. The living room opens to the backyard through sliding doors. A convenient half bathroom and a washer (updated in 2023) are also located on the first floor. Upstairs, you will find three bedrooms and a full bathroom with a double-sink

  Jie Liu Keller Williams Hudson Valley

  15 Rivervale Rd, Middletown, NY 10940
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  /43

  $460,000

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

  3 Arden Ct, Middletown, NY 10940

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

  Justin Jordan Keller Williams Realty

  3 Arden Ct, Middletown, NY 10940
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  /45

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  17 Ross Ln, Middletown, NY 10941

  WOW!! THIS IS THE ONE!! Wonderful family home in the heart of Scotchtown. FIRST time on the market in over half a century!! Well maintained, must see to believe! Located on over 1/4 of an acre, this home is one of a kind! Hardwood floors throughout the home. The eat in kitchen provides convenience AND easy access to the HUGE back deck. The home offers a Formal Dining Room, a Living Room with

  David Furlin BHHS Hudson Valley Properties

  17 Ross Ln, Middletown, NY 10941
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  /50

  $839,000

  • 6 Beds
  • 4 Baths
  • 3,900 Sq Ft

  225 van Duzer Rd, Middletown, NY 10940

  Discover A stunning Brand New Colonial Home over 3900 SQFT - Legal Mother Daughter Home with a Separate Entrance. This gorgeous home is now offering a beautiful outdoor kitchen with a bar setup, spacious backyard with retaining walls and a paved driveway. Featuring a grand front entrance boasts with a two-story foyer with iron stair balusters and a gorgeous combination of iron and wood. The main

  Anita S. Cristiano HomeSmart Homes & Estates

  225 van Duzer Rd, Middletown, NY 10940
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  /33

  $259,000

  • 2 Beds
  • 1.5 Baths
  • 1,230 Sq Ft

  129 Concord Ln Unit 129, Middletown, NY 10940

  An exceptional opportunity for homeowners and savvy investors, this sun-drenched, southeast-facing condo is located in one of Middletown’s rare communities with NO rental restrictions. Experience the comfort of two-level living with a thoughtful layout featuring a spacious living room on the main floor and private bedrooms upstairs. This home offers ultimate peace of mind with a Boiler and Water

  Hai Li Keller Williams Hudson Valley

  129 Concord Ln Unit 129, Middletown, NY 10940
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  /39

  $249,999

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  18-20 Bedford Ave, Middletown, NY 10940

  Welcome to this charming 2 bedroom, 1 bath Cape Cod located in the heart of Middletown, NY. Perfect starter home, ideal for those looking to downsize, or a fantastic investment opportunity. Upon entering, you are welcomed by beautiful hardwood floors, warm character, and a cozy feel that makes this home instantly inviting. Offering approximately 864 square feet of living space, this home is

  Jennifer Lappe Keller Williams Realty

  18-20 Bedford Ave, Middletown, NY 10940
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  /21

  $329,000

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

  209 Deer Ct Dr, Middletown, NY 10940

  Welcome to Deer Run, this inviting condo in the heart of Middletown, NY, where convenience meets comfort. Perfectly situated for commuters, this home offers easy access to major highways, shopping, dining, and transportation, making daily travel a breeze. Enjoy the best of suburban living with a peaceful atmosphere, all while being close to everything you need. Whether you're starting out,

  Beverly Huaman Howard Hanna Rand Realty

  209 Deer Ct Dr, Middletown, NY 10940
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  /21

  $485,000

  • 2 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’s lifestyle. Step inside to find a bright and inviting layout featuring two spacious bedrooms, each with generous closet

  Jason Madison eXp Realty

  1 High Ridge Ln, Middletown, NY 10940
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  /36

  $420,000

  • 3 Beds
  • 1 Bath
  • 1,616 Sq Ft

  525 Bloomingburg Rd, Middletown, NY 10940

  Your next chapter begins here! The bright, spacious living room sets the tone—an inviting space where you can unwind and recharge after a busy day. The generous open concept kitchen is ready for you to craft your favorite recipes and enjoy effortless everyday living.Convenience shines with a first floor bedroom and full bathroom offering comfort and flexibility. Upstairs, you’ll find two

  Kichka Pascaru Christie's Int. Real Estate

  525 Bloomingburg Rd, Middletown, NY 10940
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  /10

  $379,900

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

  37 California Ave, Middletown, NY 10940

  MLS Listing Description: Charming 3-bedroom, 2-bath traditional two-story home featuring a spacious, enclosed backyard—perfect for outdoor enjoyment and entertaining. The first floor offers an oversized living room, an open dining area, and a functional kitchen layout ideal for everyday living. Upstairs, you’ll find three comfortable bedrooms and a full bath. A walk-up attic provides convenient

  Jonathon Lee Keller Williams Hudson Valley

  37 California Ave, Middletown, NY 10940
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  /46

  $489,999

  • 2 Beds
  • 2 Baths
  • 1,612 Sq Ft

  10 Cyprus Dr, Middletown, NY 10940

  Welcome to 10 Cyprus at Wildflowers at Wallkill, where comfort, style, and easy living come together in one beautiful home. This meticulously maintained 2-bedroom, 2 full bath residence offers the convenience of single-level living with a bright, open-concept layout designed for both everyday living and effortless entertaining. Sunlight pours through oversized windows, filling the space with

  Hilary Ryan Goldman Howard Hanna Rand Realty

  10 Cyprus Dr, Middletown, NY 10940
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  /58

  $575,000

  • 12 Beds
  • 10 Baths
  • 5,004 Sq Ft

  5 Wawayanda Place, Middletown, NY 10940

  CASH ONLY - Totally renovated large home with 12 bedrooms, 8 of them being suites with their own full bathroom. 10 full bathrooms total. Home also features game room, large dining area, living room, spacious eat in kitchen with stainless appliances & island, laundry off the kitchen, large fenced patio & inground pool. Conveniently located around Orange County Community College, tennis & skate and

  Jamie Sittner Find Advisors

  5 Wawayanda Place, Middletown, NY 10940
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  /49

  $590,000

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

  48 Connors Rd, Middletown, NY 10941

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

  Kewin Garabito eXp Realty

  48 Connors Rd, Middletown, NY 10941
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  /27

  $425,000

  • 4 Beds
  • 2 Baths
  • 1,666 Sq Ft

  39 Hanford St, Middletown, NY 10940

  Coming Soon - prewar colonial in the heart of the City of Middletown.

  Soleil Jackman Howard Hanna Rand Realty

  39 Hanford St, Middletown, NY 10940
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  /13

  $560,000 Open Sat 1PM - 3PM

  • 5 Beds
  • 4 Baths
  • 1,911 Sq Ft

  35 Dogwood Dr, Middletown, NY 10940

  Just pack your bags and move in. Spacious, Comfortable and Cozy 5 bedroom 1 family house for sale. This house features 4 Bedrooms and 2 bathrooms on the upper level with a walk in closet and a bathroom in the master bedroom. The first features a 1/2 bath, renovated kitchen, separate living and dinning rooms and a walkout deck. The ground floor features a 2 car garage, finished basement with 1

  Lenworth Brisco Keller Williams Realty NYC Grp

  35 Dogwood Dr, Middletown, NY 10940
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  /37

  $199,990

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  238 Concord Ln, Middletown, NY 10940

  Welcome to 238 Concord Lane, a beautifully refreshed home in the heart of Middletown that is truly move-in ready, featuring fresh paint throughout, brand new flooring, and modern lighting that creates a bright, clean, and inviting atmosphere from the moment you step inside; ideally located just minutes from Middletown’s shops, restaurants, and everyday conveniences, this home offers the perfect

  Andi Berisha BHHS Hudson Valley Properties

  238 Concord Ln, Middletown, NY 10940
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  /8

  $159,000

  • Land
  • 0.43 Acre
  • $372,365 per Acre

  47 Carpenter Ave, Middletown, NY 10940

  PRICE IMPROVED - Available for Sale is this Prime Vacant Lot with great visibility and traffic count. Zoned HC (Highway Commercial). Permitted uses include Financial institutions, office, religious, retail and service and repair shops. Uses by special permit include clubs and lodges, day care facilities, eating/drinking establishments, funeral parlors, hotel/motel, shopping centers, veterinary

  Jacqueline Henry-Thompson Jackie Henry Realty LLC

  47 Carpenter Ave, Middletown, NY 10940
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  /17

  $599,900

  • 4 Beds
  • 3 Baths
  • 2,560 Sq Ft

  55 Eisenhower Dr, Middletown, NY 10940

  Stunning Ranch in a Highly Desired Neighborhood! Welcome to this beautifully renovated ranch-style home, perfectly situated on a spacious corner lot of over 1/3 of an acre. Offering 4 generously sized bedrooms, 3 full bathrooms and central air, this home is ideal for comfortable living and entertaining.Step inside to a huge sun-filled living room featuring oversized windows that flood the

  Jennifer Kubler eRealty Advisors, Inc

  55 Eisenhower Dr, Middletown, NY 10940
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  /13

  $455,000

  • 4 Beds
  • 2 Baths
  • 1,466 Sq Ft

  225 Monhagen Ave, Middletown, NY 10940

  Great location with mixed-use zoning potential! This nicely maintained property offers a comfortable and practical layout that is perfect for family living.The home features 4 bedrooms and 2 full bathrooms, providing generous and comfortable living space. A finished basement offers additional room that can be used for entertainment, a recreation area, home office, or extra living

  Jin Pang Panorama Realty

  225 Monhagen Ave, Middletown, NY 10940
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  /8

  $490,000

  • 3 Beds
  • 2.5 Baths
  • 2,191 Sq Ft

  19 Magnolia Park Rd, Middletown, NY 10940

  Welcome to this beautifully maintained newer-construction home in the sought-after Magnolia Park section of the Maple Fields community in Middletown. Built in 2019–2020, this spacious residence offers approximately 2,100 square feet of modern living with an open-concept layout designed for today’s lifestyle. The main level features a bright and airy living space, a stylish kitchen with granite

  Daniel Amodeo AMO Realty

  19 Magnolia Park Rd, Middletown, NY 10940
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  /30

  $515,000

  • 3 Beds
  • 2.5 Baths
  • 2,763 Sq Ft

  17 Woodrose Ct, Middletown, NY 10940

  Discover the perfect blend of classic charm and modern comfort in this beautiful Colonial-style home. Filled with warmth and character, this cozy yet spacious residence features soaring high ceilings that create an open, airy feel throughout. Each room is thoughtfully designed to offer both elegance and comfort, making the home feel inviting from the moment you step inside. With its timeless

  Ermelinda Mclaughlin eXp Realty

  17 Woodrose Ct, Middletown, NY 10940
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  /31

  $399,998

  • 4 Beds
  • 1 Bath
  • 1,296 Sq Ft

  10 Wisner Ave Unit 12, Middletown, NY 10940

  Welcome to 10 Wisner Avenue, a beautifully updated ranch that seamlessly blends style, comfort, and modern convenience. Renovated in 2023, this home features a new roof, life-proof flooring throughout, a stunning kitchen with butcher block countertops, subway tile backsplash, and stainless steel appliances, a Navien tankless heater, and a new washer and dryer. Enjoy the ease of single-level

  Sean Israelski Howard Hanna Rand Realty

  10 Wisner Ave Unit 12, Middletown, NY 10940
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  /43

  $430,000

  • 3 Beds
  • 1.5 Baths
  • 1,363 Sq Ft

  24 Rockwell Ave, Middletown, NY 10940

  Welcome home to 24 Rockwell Avenue, a beautifully updated residence that seamlessly blends comfort with modern convenience. Completely renovated in 2023, this move-in ready home features a new roof, life-proof flooring throughout, a stylish kitchen with stainless steel appliances and butcher block countertops, as well as a new washer and dryer. The functional center hall colonial layout offers

  Sean Israelski Howard Hanna Rand Realty

  24 Rockwell Ave, Middletown, NY 10940
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  /12

  $349,900

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

  70 Linden Ave, Middletown, NY 10940

  Wonderful Colonial Home located in a very convenient location in the heart ofMiddletown. Walk to all the wonderful Restaurants and Shops. Enjoy the spaciousness of the home that features a Large Living Room, Formal Dining Room,Working Kitchen and Full Bathroom. Second level offers a Primary Bedroom and two additional Bedrooms and Full Bathroom. Huge walk up Attic. Full Basement. Nice

  John Biasi Howard Hanna Rand Realty

  70 Linden Ave, Middletown, NY 10940
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  /27

  $574,999 Open Sat 1PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 2,255 Sq Ft

  53 Daly Rd, Middletown, NY 10940

  Say hello to the best of both worlds! A peaceful residence located in Middletown, NY! This beautifully designed residence offers a seamless flow for modern living. The heart of the home is an expansive kitchen, connected to a generous dining area—ideal for hosting dinner parties or holiday gatherings. Step outside through the sliding doors to your private oasis: an extra large refinished deck

  Michelle Pepe Curasi Realty, Inc.

  53 Daly Rd, Middletown, NY 10940
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  /45

  $564,900

  • 4 Beds
  • 2.5 Baths
  • 2,344 Sq Ft

  1 Hulse St, Middletown, NY 10940

  "NEW CONSTRUCTION!" Stunning corner-lot home in a calm suburban setting with beautiful mountain views — offering space, upgrades, and thoughtful design throughout. This impressive property offers approximately 2,344 sq ft of living space and features 9-ft ceilings on the main level and 8-ft ceilings upstairs, enhancing the open and airy layout. The upgraded 400+ sq ft kitchen is a true highlight,

  Chaim Friedman MS Realty Group USA, Inc

  1 Hulse St, Middletown, NY 10940
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  /24

  $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 Keller Williams Hudson Valley

  30 Daly Rd, Middletown, NY 10940
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  /17

  $259,999

  • 4 Beds
  • 1 Bath
  • 1,140 Sq Ft

  29 Parsons Ln, Middletown, NY 10940

  Fantastic opportunity at 29 Parsons! This property is being offered as a cornerstone of a 3-parcel investment package. While individually the 4 bedroom home on 6+ acres of land the complete 3-property bundle—including an additional 5+ acres of land—is available for a package. The home is a 4 bedroom & lives as a 2 large bedrooms and a laundry room. Perfect for developers or those looking for a

  Camelia Pena-Rivera RE/MAX Distinguished Hms.&Prop

  29 Parsons Ln, Middletown, NY 10940
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  /3

  $350,000

  • Land
  • 1.42 Acres
  • $245,752 per Acre

  65 James P Kelly Way, Middletown, NY 10940

  Great location for a business. C-3 Zoning allows for any business, commercial or residential mix use. 262 feet frontage. Annual Average Daily Traffic (AADT) for 2023 is 10,569. There was a pre-approved building plan for a doctor's office building. The land is in the city of Middletown. The city will provide water and sewer. C-3 allow for 6 story mix-use business and residential building with the

  Jonathon Lee Keller Williams Hudson Valley

  65 James P Kelly Way, Middletown, NY 10940
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  /44

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 2,809 Sq Ft

  7 Starhaven Ave, Middletown, NY 10940

  This well-maintained home offers strong structural integrity, reliable mechanicals, and a flexible layout—ideal for buyers seeking a move-in-ready foundation with the opportunity to personalize cosmetic finishes over time. The main level features comfortable living and dining areas, an efficient kitchen layout, and generous natural light throughout. All bedrooms and the hallway include existing

  Michelle Gruberger Real Estate Circuit Inc

  7 Starhaven Ave, Middletown, NY 10940
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  /46

  $674,900

  • 4 Beds
  • 2.5 Baths
  • 2,360 Sq Ft

  320 Highland Avenue Extension, Middletown, NY 10940

  Rare Gem – Like-New Home with Park-Like Setting; StunningDesign. Welcome to a truly special property—an exceptional home thatcombines style, comfort, and an unbeatable location. Homes Like thisrarely come to market. Meticulously maintained and showing Like new,this residence offers the perfect blend of elegance and convenience with a tastefully designed interior with modern

  Matthew Gibbs Keller Williams Hudson Valley

  320 Highland Avenue Extension, Middletown, NY 10940
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  /29

  $650,000

  • 3 Beds
  • 4 Baths
  • 2,320 Sq Ft

  33 O Brian Rd, Middletown, NY 10940

  Seeking privacy and tranquility without complete seclusion? This charming log home sits on 15 acres surrounded by natural beauty (partially wetlands) and peaceful views of a neighboring lake. The expansive deck is ideal for entertaining and summer barbecues, while the three-season porch provides a cozy retreat in any weather. Inside, the great room impresses with vaulted ceilings, exposed beams,

  Kokoshen Li Corcoran Country Living

  33 O Brian Rd, Middletown, NY 10940

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