Homes for Sale near Middletown High School

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  /30

  $410,000

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft

  25 Fairways Dr Unit 1, Middletown, NY 10940

  Step into this fully updated, move-in ready luxury condo located in one of the area’s most sought-after gated communities. This stunning first-floor residence has been meticulously upgraded from top to bottom—featuring designer finishes, fresh modern paint tones, and premium luxury flooring throughout. The custom kitchen is outfitted with elegant cabinetry, granite countertops, and stylish

  

  Randolph Rogers

  eXp Realty

  (845) 299-8068

  25 Fairways Dr Unit 1, Middletown, NY 10940
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  Explore Middletown High School

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  /25

  $420,000

  • 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

  (845) 436-3953

  71 Commonwealth Ave, Middletown, NY 10940
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  /42

  $475,000

  • 3 Beds
  • 3 Baths
  • 2,542 Sq Ft

  138 Reinhardt Rd, Middletown, NY 10940

  Nestled on 1.5 park like acres with lots of privacy in the back, built in 1969 and lovingly cared for by the same family for over 56 years is this unique front back split level with four levels in the home. Step through the front door to find a half bath, home office with lots of shelving already in place, and second room used as a craft room, play room,or additional home office conveniently

  

  Lynelle Alessi

  Keller Williams Hudson Valley

  (845) 447-9473

  138 Reinhardt Rd, Middletown, NY 10940
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  /2

  $250,000

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  13 Smith St, Middletown, NY 10940

  Looking to add a rental property to your porfolio? This 3 bedroom, 1 bathroom home might be the one. Long term tenant looking to stay. Located in the heart of the city of Middletown. Walking distance to local shops, restaurants, supermarket, park and much more. Located on a one way street with low local traffic. Call today for appoiintment.

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 299-0839

  13 Smith St, Middletown, NY 10940
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  /26

  $410,000

  • 4 Beds
  • 2 Baths
  • 1,668 Sq Ft

  31 Beattie Ave, Middletown, NY 10940

  Great 2 family home in the city of Middletown. Each apartment features 2 bedrooms, 1 bathroom. This property is located in a zoning that requires one of the apartments is occupied by the owner. House is well maintained and cared for. Large lot offers plenty of yard and parking. Walk-up attic offers plenty of storage. Each tenant has their own washer and dryer hook-up. Detached 2 car garage ideal

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 286-4605

  31 Beattie Ave, Middletown, NY 10940
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  /2

  $380,000

  • 5 Beds
  • 2 Baths
  • 2,440 Sq Ft

  44 Houston Ave, Middletown, NY 10940

  Excellent opportunity to own a 2 family house whether you are an investor or want to live in one of the units and rent the second one. Spacious apartments. First floor apartment has 3 bedrooms and 1 bathroom, second floor apartment has 2 bedrooms and 1 bath. Conveniently located, walking distance to Touro College where students are always looking for close by rentals. Minutes to I86 and I84,

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 497-6793

  44 Houston Ave, Middletown, NY 10940
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  /21

  $599,000

  • 4 Beds
  • 3 Baths
  • 2,552 Sq Ft

  125 Whipple Rd, Middletown, NY 10940

  Discover the perfect blend of serenity and comfort in this stunning 4-bedroom, 3-bathroom raised ranch nestled on a sprawling 1.5-acre lot in the heart of Middletown, NY. As you step inside, the heart of the residence, a spacious and sunlit living area, invites family gatherings and effortless entertaining. Culinary enthusiasts will delight in the modern kitchen, boasting sleek appliances and

  Eboni Navas Julia B Fee Sothebys Int. Rlty

  125 Whipple Rd, 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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  /35

  $589,000

  • 4 Beds
  • 3 Baths
  • 2,732 Sq Ft

  24 3rd St, Middletown, NY 10940

  BETTER THAN NEW! SPACIOUS 4-Bedroom, 3-Full Bath Bi-Level ColonialWelcome to this meticulously maintained home offering over 2,700 sq ft of beautifully finished living space that blends modern style with timeless charm.Step into the gorgeous eat-in kitchen, thoughtfully designed with:A large center island with ample seatingGleaming hardwood floorsVaulted

  Jane Panico Realty Promotions Inc

  24 3rd St, Middletown, NY 10940
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  /38

  $499,999

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

  7 Avoncroft Ln, Middletown, NY 10940

  Discover the perfect balance of modern design and everyday comfort in this beautifully updated 3-bedroom, 3-bath corner townhouse, ideally located in one of Middletown’s most sought-after neighborhoods. Step inside and be welcomed by a bright, open-concept living space that feels both chic and inviting. The stylishly renovated kitchen is a true standout and it is complete with sleek countertops,

  Kewin Garabito eXp Realty

  7 Avoncroft Ln, Middletown, NY 10940
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  /27

  $429,000

  • 3 Beds
  • 2.5 Baths
  • 2,223 Sq Ft

  104 Monhagen Ave, Middletown, NY 10940

  Step into timeless charm with this beautifully renovated Victorian-style home! This bright and sunny 3-bedroom, 2.5-bath residence has been thoughtfully updated while maintaining its classic character. Gleaming hardwood floors flow throughout, and the inviting wrap-around porch offers the perfect spot for morning coffee or evening relaxation. Inside, you’ll find an open and airy layout with

  Jeffrey Hozias Howard Hanna Rand Realty

  104 Monhagen Ave, Middletown, NY 10940
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  /39

  $415,789

  • 5 Beds
  • 2 Baths
  • 1,920 Sq Ft

  15 Rowan St Unit 13, Middletown, NY 10940

  Discover the perfect blend of comfort and charm in this beautifully updated home, nestled on a coveted double corner lot. Surrounded by lush hedges and offering ample parking, this residence welcomes you with curb appeal and room to spare. Inside, you'll find five spacious bedrooms, including a convenient first-floor bedroom, ideal for guests or flexible living needs. The home boasts two full

  Juan Bautista Keller Williams Realty

  15 Rowan St Unit 13, Middletown, NY 10940
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  /35

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,823 Sq Ft

  30 Wilson St, Middletown, NY 10940

  MAGAZINE READY!!!! HGTV CALLED, YOUR DREAM HOME JUST HIT THE MARKET! Absolutely Stunning Newly Renovated Raised Ranch in Middletown! Prepare to be impressed by this incredible, newly renovated raised ranch, ideally situated in a quiet and peaceful Middletown neighborhood. Thoughtfully redesigned with impeccable taste and high end, on-trend finishes, this home offers both style and substance in

  Frank Muccari Cronin & Company Real Estate

  30 Wilson St, Middletown, NY 10940
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  /17

  $309,900

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

  71 Jordan Ln, Middletown, NY 10940

  Welcome to this sought-after 2-bedroom, 2.5-bath townhouse in Mountainside Hills Condominium. The main level has hardwood floors, a kitchen dining area, a spacious living room with access to your private deck, a powder room, and an in-unit laundry room. Upstairs, you'll find the primary bedroom with an ensuite bathroom and walk-in closet, plus an additional bedroom and a full bath. The home also

  Jonathon Lee Keller Williams Hudson Valley

  71 Jordan Ln, Middletown, NY 10940
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  /31

  $589,900

  • 4 Beds
  • 2.5 Baths
  • 2,628 Sq Ft

  658 Ingrassia Rd, Middletown, NY 10940

  Welcome to this beautifully maintained Cape Cod-style home offering 2,628 square feet of versatile living space set on a private and picturesque 2.3-acre lot. This charming residence blends classic design with modern comfort, featuring generous room sizes, abundant natural light, and timeless appeal. The main level boasts a thoughtfully designed floor plan, ideal for both daily living and

  Rebecca Matta-Candela Keller Williams Realty

  658 Ingrassia Rd, Middletown, NY 10940
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  /26

  $265,000

  • 2 Beds
  • 2 Baths
  • 1,146 Sq Ft

  162 Deer Ct Dr, Middletown, NY 10940

  Beautiful Condo in a Prime Location!Experience the perfect blend of comfort and convenience in this ideally located condo, perfect for commuters and those who love being close to the action. Just minutes from major highways, this home offers easy access to shopping centers, restaurants, and daily essentials.For city bound travelers, transportation is a breeze with nearby access to the

  Beverly Huaman Howard Hanna Rand Realty

  162 Deer Ct Dr, Middletown, NY 10940
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  /20

  $269,900

  • 2 Beds
  • 2.5 Baths
  • 880 Sq Ft

  147 Ruth Ct, Middletown, NY 10940

  Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in Middletown! Featuring a spacious and inviting layout, this condo boasts a generously sized primary bedroom with a walk-in closet. Conveniently located close to shops, restaurants, and entertainment, you'll love the ease of access to everything you need. Whether you're relaxing at home or exploring the vibrant local area, this

  Matthew Gibbs Keller Williams Hudson Valley

  147 Ruth Ct, Middletown, NY 10940
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  /16

  $429,999

  • 6 Beds
  • 2 Baths
  • 1,878 Sq Ft

  19 Wawayanda Ave, Middletown, NY 10940

  Price reduced....... A Must see... Fully available opportunity knocks to own this colonial home, located in the heart of the Hudson Valley. Entering this home with a long foyer that leads into a living room, spacious dining room with plenty of natural light, eat in kitchen, Kitchen is updated with lots of cabinet space front deck, back porch, new flooring for the entire house. New roof,

  Samar Tarazi Keller Williams Realty

  19 Wawayanda Ave, Middletown, NY 10940
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  /30

  $449,900

  • 3 Beds
  • 2.5 Baths
  • 1,987 Sq Ft

  7 Roosevelt Ave, Middletown, NY 10940

  Welcome to this charming ranch-style home located on a desirable corner lot in the city of Middletown. Spanning just under 2,000 square feet, this inviting residence features spacious rooms throughout. As you enter, you'll be greeted by custom woodwork and elegant wainscoting that add a touch of sophistication throughout this home. The layout is accentuated by tile flooring that flows seamlessly

  Patricia Sassi RE/MAX Benchmark Realty Group

  7 Roosevelt Ave, Middletown, NY 10940
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  /26

  $410,000

  • 4 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  47 Prince St, Middletown, NY 10940

  Welcome to this lovely, renovated. Formerly a 3 bedroom/2-bathroom house, this home has been renovated in 2023 into a 4 bed/2.5 bath adding a 1st Floor Master Bedroom Suite, increasing the square footage of living space. This house has plenty of character and is better than new construction. Open Concept Layout, Enclosed Porch, Luxury Vinyl Flooring, Stainless Steel Appliances, Butcher Block

  D'Wana Haynesworth YourHomeSold Guaranteed Realty

  47 Prince St, Middletown, NY 10940
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  /2

  $419,000 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,245 Sq Ft

  77 Prince St, Middletown, NY 10940

  Welcome to this beautiful well maintained contemporary two story home nestled in the heart of Middletown. Offering you a bright and spacious living room to a formal dining room, a beautiful kitchen, 3 great size bedrooms, 2.5 bathrooms with a full size basement and a car garage. Plus plenty of closets with its laundry room. With its level backyard and great size deck, you will enjoy your

  Anita S. Cristiano HomeSmart Homes & Estates

  77 Prince St, Middletown, NY 10940
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  /34

  $319,000

  • 3 Beds
  • 2.5 Baths
  • 1,452 Sq Ft

  15 Silo Ln, Middletown, NY 10940

  The owner of this home decided to give you a fresh coat of paint and add new flooring to the first level to instantly make you fall in love with the home as soon as you walk in! This home located in the desirable The Meadows Community in the Town of Wallkill. Let's talk about how this is an end unit which allows privacy and a spacious yard. When you enter you will notice the eat in kitchen that

  Pedro Garcia Curasi Realty, Inc.

  15 Silo Ln, Middletown, NY 10940
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  /19

  $369,000

  • 4 Beds
  • 1.5 Baths
  • 1,272 Sq Ft

  35 Woods Place, Middletown, NY 10940

  This charming four-bedroom, one-bathroom home offers comfortable living space with a versatile layout. The layout provides plenty of room with flexible living spaces. Located in a welcoming Middletown neighborhood, you'll enjoy easy access to quality schools, convenient public transportation, and shopping options just minutes away. Whether you're starting fresh or looking to upgrade, this

  Kevin Sanabria eRealty Advisors, Inc

  35 Woods Place, Middletown, NY 10940
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  /16

  $599,000

  • 3 Beds
  • 2 Baths
  • 2,584 Sq Ft

  35 Harrison St, Middletown, NY 10940

  Discover exceptional rental income potential with this spacious six-bedroom, two-bathroom multi-family property in the heart of Middletown. This investment opportunity offers generous living spaces. Located near Middletown Mini Market for daily essentials and close to Beattie Hill Park for outdoor recreation. The property sits conveniently near Middletown High School and public transportation via

  Kevin Sanabria eRealty Advisors, Inc

  35 Harrison St, Middletown, NY 10940
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  /29

  $329,000

  • 4 Beds
  • 2 Baths
  • 2,460 Sq Ft

  9 Albert St, Middletown, NY 10940

  3 FINISHED FLOORS! Welcome to this exceptional income generating multi-residential property! Ideally situated near Middletown’s restaurants, shopping malls, public transportation to NYC, major highways, and hospital facilities. This property offers unmatched convenience. Each apartment boasts two spacious bedrooms, an over-sized living room perfect for your largest furniture set, and an

  Robert 'Bob' & Frances 'Fran' Murray Howard Hanna Rand Realty

  9 Albert St, Middletown, NY 10940
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  /30

  $399,999

  • 3 Beds
  • 1.5 Baths
  • 1,160 Sq Ft

  5 Mills Ave, Middletown, NY 10940

  LOCATION, LOCATION, LOCATION! Don’t miss this charming 3 Bedroom, 1.5 Bathroom Two-Story Home located in the heart of Middletown and within the Middletown School District. This home offers unbeatable convenience—just minutes from local restaurants, shopping centers, banks, healthcare facilities, and postal services. Situated close to elementary and secondary schools, and just blocks from Orange

  Richard Baxter Keller Williams Realty

  5 Mills Ave, Middletown, NY 10940
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  /27

  $430,000

  • 5 Beds
  • 2 Baths
  • 2,447 Sq Ft

  2 Mountain Ave, Middletown, NY 10940

  Step into this spacious and versatile raised-ranch style two-family home, perfectly located in the quiet neighborhood of Middletown!This well-maintained property offers a total of 5 bedrooms, 2 full bathrooms, and a bonus room ideal for a home office, playroom, gym, or guest space tailored to fit your lifestyle.The upper-level unit features a bright and open layout with a spacious living

  Jeaneth Pino-Bartchak RE/MAX Benchmark Realty Group

  2 Mountain Ave, Middletown, NY 10940
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  /50

  $645,000

  • 3 Beds
  • 2.5 Baths
  • 2,548 Sq Ft

  8 Green Ct, Middletown, NY 10940

  This well-maintained 3-level townhome sits within a luxury gated community of The Fairways, right next to a golf course and just minutes from major highways, Garnet Health Medical Center, shopping, and restaurants. The home offers a 2-car garage, a finished basement with garage-level entry, and a practical layout designed for comfortable living. Hardwood floors span the main level, which features

  Jie Liu Keller Williams Hudson Valley

  8 Green Ct, Middletown, NY 10940
• 

  

  /27

  $295,000

  • 3 Beds
  • 1.5 Baths
  • 1,400 Sq Ft

  105 Sheffield Dr, Middletown, NY 10940

  Town of Wallkill Townhouse - Low Taxes - Great InvestmentThis charming 3-bedroom, 1.5-bath home is your perfect mix of space, location, and value. Nestled on a generous lot with a large yard, there's plenty of room for play, gardening, or entertaining under the stars. Step out from your primary bedroom onto a balcony—the ideal spot for morning coffee or winding down with a book while

  Cindy-Lee Dorcely Keller Williams Hudson Valley

  105 Sheffield Dr, Middletown, NY 10940
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  /21

  $519,000

  • 2 Beds
  • 2 Baths
  • 3,090 Sq Ft

  6 Broad St, Middletown, NY 10940

  Great two family duplex located in the City of Middletown. It's conveniently located walking distance to Touro College , I84 and I86, and also close to local shops and restaurants . Located approximately 70 miles North of New York City this property has a strong income potential with long term upside . At one time this was a triplex and is now a legal duplex. The 2nd floor apartment has 2

  Neal Kolze Curasi Realty, Inc.

  6 Broad St, Middletown, NY 10940
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  /15

  $465,000

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

  30 Avoncroft Ln, Middletown, NY 10940

  **Welcome to 30 Avoncroft Lane, Middletown, NY!**This beautifully maintained 3-bedroom, 2.5-bath townhouse is nestled in the desirable Woodside Knolls community. Step inside to discover updated flooring throughout and a bright, versatile layout perfect for modern living. The spacious finished basement offers endless possibilities—use it as a home gym, playroom, family room, or your own

  Cindy-Lee Dorcely Keller Williams Hudson Valley

  30 Avoncroft Ln, Middletown, NY 10940
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  /5

  $280,000

  • 4 Beds
  • 3 Baths
  • 1,374 Sq Ft

  22 Bonnell St, Middletown, NY 10940

  Welcome to 22 Bonnell St, a charming 4-bedroom, 3-bathroom home situated on a desirable corner lot on a quiet street in the heart of Middletown, NY. This spacious residence is brimming with potential, offering a unique opportunity to customize and create your dream home exactly the way you envision it. While the home could benefit from some updating, its solid foundation and prime location make

  Emmett McDowell Keller Williams Rlty Integrity

  22 Bonnell St, Middletown, NY 10940
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  /45

  $450,000

  • 5 Beds
  • 2 Baths

  16-18 Claremont Ct, Middletown, NY 10940

  Charming Renovated Duplex in Prime Middletown Location! Located just a short walk from Fancher-Daviage Park and pool, this beautifully updated duplex offers exceptional value and flexibility for owner-occupants or investors alike.The main unit features three spacious bedrooms and one stylishly updated bathroom, showcasing gleaming hardwood floors, a sun-filled lanai-style room, and a modern

  Shari Felder Keller Williams Realty

  16-18 Claremont Ct, Middletown, NY 10940
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  /16

  $649,900

  • 4 Beds
  • 3 Baths
  • 2,444 Sq Ft

  744 Mount Hope Rd, Middletown, NY 10940

  A beautiful colonial home sitting on 10.80 acres with open layout is being built in the town of Wallkill. Offering about 2400 SQFT living space including the finished basement with 4 bedrooms, 3 full bathroom and a one car garage. From the living room to a dining area and it's open to a beautiful kitchen with Quartz countertops, an island and stainless appliances. This gorgeous home will have 1

  Anita S. Cristiano HomeSmart Homes & Estates

  744 Mount Hope Rd, Middletown, NY 10940
• 

  

  /40

  $489,000

  • 3 Beds
  • 2.5 Baths
  • 2,491 Sq Ft

  5 Cornwall Ln, Middletown, NY 10940

  Welcome to this ending unit townhouse nestled in the community of Woodside Knolls. This beautifully maintained home offers 3 spacious bedrooms, 2.5 bathrooms, and an attached 2-car garage. With over 2,400 square feet of living space, this residence seamlessly blends comfort, and functionality. Step inside to discover the Oak Hardwood Floors throughout the main level. The bright and airy living

  Wenpeng Guan Keller Williams Hudson Valley

  5 Cornwall Ln, Middletown, NY 10940
• 

  

  /22

  $249,900

  • 2 Beds
  • 1 Bath
  • 820 Sq Ft

  58 Wawayanda Ave, Middletown, NY 10940

  A Great Place to Call Home or perfect for those looking to expand your real estate investment portfolio, this charming Middletown home offers the perfect blend of comfort, convenience, and value. Cozy yet spacious, this home has been thoughtfully updated and is truly move-in ready! With 2 bedrooms, a home office which offers much potential for additional space and a full bath you will have all

  Frank Muccari Cronin & Company Real Estate

  58 Wawayanda Ave, Middletown, NY 10940
• 

  

  /17

  $315,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,220 Sq Ft

  38 Sheffield Dr, Middletown, NY 10940

  Welcome to this beautiful 3-bedroom, 1.5-bath townhouse-style single-family home, ideally located on a spacious corner lot in the heart of Middletown, NY. This charming residence has been freshly painted throughout and features brand-new carpeting, offering a bright, clean, and move-in-ready atmosphere from the moment you step inside.The home’s thoughtful layout provides a comfortable and

  Malik Subhani Weichert Realtors

  38 Sheffield Dr, Middletown, NY 10940
• 

  

  /29

  $349,750

  • 2 Beds
  • 1 Bath
  • 1,324 Sq Ft

  9 Grandview Ave, Middletown, NY 10940

  Step inside this Middletown ranch home and be pleasantly surprised by the spacious layout, updated features, and inviting vibe that make this home a true gem. With newer windows, kitchen appliances, and central air conditioning, comfort and convenience are already checked off your list. The cute breezeway connecting the garage to the house adds a fun bonus space—think sunny sitting area or

  Patricia Sassi RE/MAX Benchmark Realty Group

  9 Grandview Ave, Middletown, NY 10940
• 

  

  /9

  $395,000

  • 4 Beds
  • 2 Baths

  25 Mill St, Middletown, NY 10940

  Beautifully recently renovated 2 story, with 2 br apartment on second for at $2000./month, has 2 yr lease, vacant first floor unit with matching new renovation, includes washer and dryer. New kitchen with granite counters, new full tile bath. High efficiency furnaces. First floor is a commercial space, ready to occupy. Tenant pay utilities. Come and see!!!!

  Mark Tierney Howard Hanna Rand Realty

  25 Mill St, Middletown, NY 10940
• 

  

  /15

  $349,000

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft

  112 Sunrise Park Rd, New Hampton, NY 10958

  Welcome to 112 Sunrise Park Road! Tucked away at the end of a quiet cul-de-sac, this 2-Bedroom, 1-Bath gem offers the perfect blend of privacy and convenience. Located just outside of town, you’ll enjoy peaceful living with quick access to all major highways and town amenities. The home features an oversized 2-car garage and a full unfinished basement brimming with potential—whether you envision

  Ryan Barrett Keller Williams Realty

  112 Sunrise Park Rd, New Hampton, NY 10958

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