Middletown, NY Houses for Sale

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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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  /25

  $405,000 Open Sat 2:30PM - 4PM

  • 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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  /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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  /21

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,639 Sq Ft

  389 Fair Oaks Rd, Middletown, NY 10940

  Beautiful contemporary capecod offers 3 to 4 bedrooms and 2 full bathrooms. Open kitchen/dining room with stainless steel appliances, brand new stove, microwave is only 1 year old. Large patio in front of the house. Ceramic tiles and hardwood floors throughout. Primary bedroom has a walk-in closet. First floor bedroom makes an ideal guest room, or for someone that doesn't want to do do stairs.

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 208-1615

  389 Fair Oaks Rd, Middletown, NY 10940
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  /25

  $350,000

  • 4 Beds
  • 2 Baths
  • 1,716 Sq Ft

  29 Beth Dr, Middletown, NY 10941

  Nice sized Raised Ranch in an established neighborhood in the desirable Pine Bush Schools. Owned by the original owners since 1978. Home consists of a kitchen/livingroom combo on the first floor with a full bath and 3 bedrooms down the hall and beautiful hard wood floors.Down stairs is a family room and an additional bedroom and bath along with a two car garage. Needs some work but a great

  

  Lynelle Alessi

  Keller Williams Hudson Valley

  (329) 209-8449

  29 Beth Dr, Middletown, NY 10941
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  /41

  $575,000

  • 4 Beds
  • 2.5 Baths
  • 2,672 Sq Ft

  1583 Mountain Rd, Middletown, NY 10940

  Looking for your piece of paradise?... You just found it! This great contemporary home offers 4 to 5 bedrooms, 2.5 bathrooms, a 2 car garage on 1 acre of land. Large windows, vaulted ceilings and skylights allow the flow of natural light throughout the house. You'll also find beautiful hardwood floors throughout. Kitchen was updated in 2020 offering plenty of cabinets and stainless steel

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 208-3559

  1583 Mountain Rd, Middletown, NY 10940
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  /50

  $879,000

  • 4 Beds
  • 2.5 Baths
  • 3,437 Sq Ft

  3 Kings Dr, Middletown, NY 10941

  Luxury Living in Hamptonburgh. Nestled in the prestigious Windsor Estates enclave, within the sought-after Goshen School District, this exceptional Contemporary residence offers a rare blend of elegance, comfort, and convenience. With nearly 3,500 sqft of thoughtfully designed living space, this striking home features 4 spacious bedrooms, 3 bathrooms, and a 3-car garage. Step into a grand

  

  Christina Rowan

  Howard Hanna Rand Realty

  (845) 393-3879

  3 Kings Dr, Middletown, NY 10941
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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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  /50

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,566 Sq Ft

  166 Hilly's Ln, Middletown, NY 12455

  Escape to your own private retreat on 13.2 acres in the charming community of New Kingston. This updated cedar sided chalet offers 3 bedrooms plus a cozy sleeping nook, 2 beautifully renovated baths, and a long list of thoughtful upgrades within the past 24 months. A Tuli Kivi soapstone stove fireplace insert brings warmth and charm, but the true showstopper is the 18’ x 18’ screened

  Susan Doig Listing by Coldwell Banker Timberland Properties

  

  166 Hilly's Ln, Middletown, NY 12455
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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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  /29

  $569,000

  • 4 Beds
  • 2.5 Baths
  • 2,284 Sq Ft

  88 James Clark Dr, Middletown, NY 10940

  Nestled in the scenic Town of Wallkill and within the Pine Bush School District, this elegant 2,284 sq. ft. stucco-front center hall colonial offers timeless charm and modern convenience. The grand entryway welcomes you with an automatic chandelier, gleaming hardwood floors, formal dining room and an inviting layout designed for both comfort and entertaining. Enjoy year-round comfort with central

  Debbie Goldstein Howard Hanna Rand Realty

  88 James Clark Dr, Middletown, NY 10940
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  /21

  $479,900 Open Sat 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,055 Sq Ft

  93 Rolling Meadows Rd, Middletown, NY 10940

  Looking for more space, peace and comfort while still being close to New York City? Welcome to this beautiful four bedroom PLUS home nestled in one of the most desirable counties. With easy access to major highways, NYC commuter route and just minutes from the famous Woodbury Common Premium Outlets, this home offers the best of both convenience and tranquility. Step inside and discover updated

  Suzanne Bongiorno Century 21 E & M Williams Rlty

  93 Rolling Meadows Rd, Middletown, NY 10940
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  /47

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 2,032 Sq Ft

  29 Keasel Rd, Middletown, NY 10940

  Welcome to 29 Keasel Road—a private oasis that perfectly blends elegance, comfort, and convenience. Just minutes from the expressway and premier shopping, this stunning home boasts thoughtful upgrades including a brand-new dishwasher and gutters (2024) and well-maintained windows (5–10 years). Step outside to your own resort-style retreat featuring a sparkling in-ground pool, serene functioning

  Ramanjit Dhanoa eXp Realty

  29 Keasel Rd, Middletown, NY 10940
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  /45

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 2,933 Sq Ft

  116 Lewis Landing Rd, Middletown, NY 10940

  Wow! Country setting with all the room you need.1.8 acres with fenced back yard and surrounded by trees. This raised ranch is in the Minisink Valley School District and close to commuter routes and transport. It comes with an attached oversized 2 car garage(26'X30'),and a two car turn around off the driveway entrance. A recent addition offers a first-floor flex space; family room/office with a

  Thomas Smith Cronin & Company Real Estate

  116 Lewis Landing Rd, Middletown, NY 10940
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  /33

  $539,999 Open Sat 1PM - 3PM

  • 3 Beds
  • 3 Baths
  • 2,696 Sq Ft

  2 Danielle Ct, Middletown, NY 10940

  Welcome to 2 Danielle Court, a stunning stucco home tucked away on just over a half-acre of land in desirable Middletown, NY. With 3 spacious bedrooms, 3 full bathrooms, and a versatile media room on the lower level, this property offers comfort, style, and endless possibilities.Step inside and you’ll immediately notice the home’s inviting flow and abundant natural light. The open spaces and

  Ravyn Green YourHomeSold Guaranteed Realty

  2 Danielle Ct, Middletown, NY 10940
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  /35

  $799,000

  • 5 Beds
  • 3.5 Baths
  • 4,255 Sq Ft

  24 Woodside Ct, Middletown, NY 10941

  This stunning upgraded Colonial offers rare privacy at the end of a quiet cul-de-sac, just 10 mins outside of Middletown. A dream kitchen with high-end appliances, marble Carrara countertops, convection microwave, and double oven air fryer. Bonus room over the garage. Hardwood and tile floors throughout, marble / granite countertops in all baths, three walk-in closets, LED recessed

  Philip Barnao eXp Realty

  24 Woodside Ct, Middletown, NY 10941
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  /48

  $599,000

  • 4 Beds
  • 3.5 Baths
  • 2,747 Sq Ft

  31 Highland View Place, Middletown, NY 10940

  Welcome to your dream home! Enjoy easy one floor living in this expansive ranch with its timeless decor and most tasteful updates! Meticulously maintained with exceptional attention to detail, inside and out, is evident as soon as you pull up to the front of the house with its extra wide paver stone driveway and mature landscaping. Step inside to discover light filled spaces, vaulted ceilings,

  Abbe Distelburger Keller Williams Realty

  31 Highland View Place, Middletown, NY 10940
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  /40

  $449,000

  • 4 Beds
  • 2 Baths
  • 1,634 Sq Ft

  100 Academy Ave, Middletown, NY 10940

  WELCOME HOME!!! A lovely and spacious single family property in the center of Middletown is looking for its new owners, ready to move in!!!The house features a total of 4 bedrooms, 2 full baths, plus a office room, with a semi finished basement for laundry and storage.The 1st floor consists of a nice kitchen with granite countertops, big entry foyer, dining room, living room and a full

  Mordy Abelesz eXp Realty

  100 Academy Ave, Middletown, NY 10940
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  /31

  $470,000

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft

  295 Lybolt Rd, Middletown, NY 10941

  Spacious home with large yard on a quiet street - what more could you want? This beautiful contemporary home has had many upgrades over the last few years! The main level features an open kitchen, dining room and living room with partial wrap around deck - perfect for entertaining or just extended living space. Three large bedrooms and two full bathrooms complete the upper level. Downstairs

  Britanni Gaucher Keller Williams Realty

  295 Lybolt Rd, Middletown, NY 10941
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  /32

  $539,000

  • 3 Beds
  • 2.5 Baths
  • 2,994 Sq Ft

  43 Last Rd, Middletown, NY 10941

  Stunning large ranch zoned 215 - 1 Family Res w/Apt, many updates set up for extended family...two kitchens! Come see this beautifully maintained home features master bedroom with bath, walking closet, sunken living room, large open kitchen featuring dining area with sliding door to huge deck overlooking a fenced in level yard and shed. This cedar sided home has been meticulously maintained,

  Mary Jo Coleman Curasi Realty, Inc.

  43 Last Rd, Middletown, NY 10941
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  /37

  $499,999

  • 4 Beds
  • 3 Baths
  • 2,160 Sq Ft

  612 Shoddy Hollow Rd, Middletown, NY 10940

  Located on one of the most scenic and peaceful roads in Orange County, this spacious mother-daughter home offers exceptional privacy on a full acre of land, just minutes from Middletown shopping, dining, and NYC train access. Tucked away on a quiet road, the home provides a rare sense of seclusion while still being close to everyday conveniences. Inside, you’ll find two full kitchens with

  Kewin Garabito eXp Realty

  612 Shoddy Hollow Rd, Middletown, NY 10940
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  /25

  $535,000

  • 1 Bed
  • 1 Bath
  • 1,088 Sq Ft

  727 Route 17m, Middletown, NY 10940

  Single Family home and mix-use property in prime location. Live on the property and have your business or use entirely for commercial purposes. This unique property offers incredible potential for various business or residential opportunities in a highly commercial area. Zoned Light Enterprise, this property provides flexibility for special uses, making it ideal for entrepreneurs,

  AnnaMarie O'Brien Curasi Realty, Inc.

  727 Route 17m, Middletown, NY 10940
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  /41

  $480,000

  • 4 Beds
  • 2.5 Baths
  • 2,848 Sq Ft

  4 Thistle Ln, Middletown, NY 10940

  Spacious & Versatile Raised Ranch in Prime Middletown Location!Not your average bi-level! This move-in-ready, raised-ranch-style home in Middletown, within the Minisink Valley School District, offers the perfect blend of convenience and comfort. Located near Garnet Medical Center, Crystal Run, shopping centers, supermarkets, and with easy access to Metro-North and major highways, it’s an

  Soleil Jackman Howard Hanna Rand Realty

  4 Thistle Ln, Middletown, NY 10940
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  /2

  $525,000

  • 5 Beds
  • 4 Baths
  • 3,140 Sq Ft

  7 Highland View Place, Middletown, NY 10940

  Welcome home to this beautifully maintained 5-bedroom, 4-bathroom raised ranch, ideally situated near the highly-rated Presidential Park Elementary School in Middletown, NY. Perfect for growing families or multi-generational living, this expansive home offers generous living space, natural light throughout, and thoughtful updates that make it move-in ready.Step inside to discover an open-concept

  Hilary Hemans-Mensah Keller Williams Realty

  7 Highland View Place, Middletown, NY 10940
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  /2

  $450,000 Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft

  3 Bonnie Brae Dr, Middletown, NY 10941

  Welcome to 3 Bonnie Brae Dr in Middletown (Pine Bush Schools). This 3-bedroom, 1-bath home offers 1,584 sq ft of living space on a 0.28-acre lot, highlighted by an in-ground pool and a charming gazebo, perfect for summer relaxing and entertaining. A detached oversized garage with a finished room above provides versatile bonus space for a studio, office, gym, or hobbies. Inside, the layout flows

  Pete Wolven Hudson Valley Home Connection

  3 Bonnie Brae Dr, Middletown, NY 10941
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  /10

  $329,000

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  64 Wawayanda Ave, Middletown, NY 10940

  FULLY AVAILABLE AND MOVE IN READY! 3 bedroom, 2 full bath home in a great commuter location. Home offers species kitchen with quartz counter tops & stainless steel appliances. Bright Living room, large tile baths, light fixtures and hardwood floors throughout. Cozy master bedroom with 2 closets and private bath located on the 2st floor. 2 other bedrooms and a full bath is located on main floor.

  Nathan Landau Loop Realty Inc

  64 Wawayanda Ave, Middletown, NY 10940
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  /34

  $950,000

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

  190 Crans Rd, Middletown, NY 10941

  Location, Location, Location! This private 55 acre Orange County, New York horse friendly property is located 75 miles north of Manhattan and features: a brand new roof (July 2025), an open floor plan house tucked at the end of a long driveway, a 4 stall center aisle horse barn with water and electric and two large horse paddocks, each with their own Nelson brand automatic waterer and 2 run-in

  Deb Cor Exclusively Equine Prop LLC

  190 Crans Rd, Middletown, NY 10941
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  /16

  $330,000

  • 2 Beds
  • 1 Bath
  • 1,016 Sq Ft

  3 Chappell Pkwy, Middletown, NY 10940

  Move-in ready and priced to sell! This charming 2-bedroom, 1-bath home at the end of a quiet cul-de-sac in Middletown offers an open living and dining area, an eat-in kitchen, a small unfinished basement for storage, and a walk-out one-car garage with additional driveway parking. Enjoy the convenience of being minutes from historic downtown Middletown’s shops, restaurants, and the Paramount

  Antonio Sanchez Harbor Gray Real Estate LLC

  3 Chappell Pkwy, Middletown, NY 10940
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  /19

  $389,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  1 Chestnut St, Middletown, NY 10940

  A must see home! This beautiful corner lot home has everything brand new inside - from the windows, closed porch, all walls with plumbing and electrical lines, kitchen with brand new cabinets, countertops and appliances: refrigerator, oven/range, microwave and dishwasher, beautiful bathrooms with tiles, - all NEW. Featuring 3 bedrooms and 2 full bathrooms. It has a great size yard for your summer

  Anita S. Cristiano HomeSmart Homes & Estates

  1 Chestnut St, Middletown, NY 10940
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  /40

  $415,000

  • 4 Beds
  • 3 Baths
  • 2,040 Sq Ft

  167 Rockwell Ave, Middletown, NY 10940

  Charming Single-Family Home for SaleWelcome to this beautifully designed, spacious single-family home, offering a perfect blend of comfort and style. Nestled in a serene space, this home is ideal for those seeking both tranquility and convenience.As you step inside, you’re greeted by an inviting open-concept layout that seamlessly connects the living, dining, and kitchen areas. The living

  Ermelinda Mclaughlin eXp Realty

  167 Rockwell Ave, Middletown, NY 10940
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  /28

  $305,000

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  111 Apple Lane Dr, Middletown, NY 10940

  Picked just for you is this adorable home on Apple Lane! From the moment you walk in, you’ll be greeted by a delightful blast from the past — knotty pine paneling, hardwood floors and an original kitchen complete with metal cabinets and whimsical upper metal cupboards with sliding glass doors that scream mid-century character. Whether you’re a fan of retro style or ready to put your modern touch

  Patricia Sassi RE/MAX Benchmark Realty Group

  111 Apple Lane Dr, Middletown, NY 10940
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  /32

  $1,888,000

  • 5 Beds
  • 9 Baths
  • 7,794 Sq Ft

  3 Bristol Dr, Middletown, NY 10941

  Amazing Mini Mansion Luxury Hse on this one ! For those that look for the very best and finest that the Hudson Valley has to offer you are sure to be amazed as you enter this 11200 plus sq ft luxurious brick colonial mansion including 3200 sq ft Indoor Pool room ! Yes you read that correctly, this home is one of the very few that features a 16 by 32 ft indoor pool attached to a 10 person jacuzzi

  Mohamed Elgoarany All American Realty Management

  3 Bristol Dr, Middletown, NY 10941
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  /27

  $414,999

  • 3 Beds
  • 2.5 Baths
  • 1,795 Sq Ft

  11 Dolson Ave, Middletown, NY 10940

  Beautifully Updated Home in the Heart of Middletown!Step into this stunning 3-bedroom, 3-bath home offering 1,795 sq ft of stylish living space. The heart of the home is the modern, fully renovated kitchen featuring sleek white cabinetry, quartz countertops, a large center island with seating, stainless steel appliances, and an eye-catching tile backsplash—perfect for cooking,

  Gleny Bencosme Coldwell Banker Realty

  11 Dolson Ave, Middletown, NY 10940
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  /44

  $299,000

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  25 Lafayette Ave, Middletown, NY 10940

  Welcome to 25 Lafayette Avenue, a charming and move-in ready 2-bedroom, 1-bath bungalow located on a quiet residential street in the heart of Middletown. This well-maintained home combines comfort and character, offering central air, stylish pet resistant vinyl flooring throughout, a sun-filled living room, and a beautifully updated kitchen with quartz countertops and ample cabinet space.The

  Kathy White Exit Realty Connections

  25 Lafayette Ave, Middletown, NY 10940
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  /41

  $1,299,000

  • 6 Beds
  • 5.5 Baths
  • 4,650 Sq Ft

  80 Pine Grove Rd, Middletown, NY 10940

  Welcome to Your Private Estate in the greater Hudson Valley region, in the Town of Mount Hope, about 70 miles from NYC, set on over 120 acres of picturesque landscape, stone-lined pastures, rolling fields, serene woods, and a stocked bass pond. This remarkable property features a total of 3 master suites and 3 bedrooms, 3 Jacuzzi. All rooms have beautiful views for a peaceful recharge. It is

  Chris Ogden Realty Promotions Inc

  80 Pine Grove Rd, Middletown, NY 10940
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  /10

  $375,000

  • 3 Beds
  • 1.5 Baths
  • 1,706 Sq Ft

  715 Stony Ford Rd, Middletown, NY 10941

  Located on 1 acre in the Town of Wallkill, this 3 bedroom Split Level home is looking for a buyer who is very handy. Being sold "as-is", in need of a new upstairs bathroom, and a kitchen renovation. Minutes from highways and medical facilities.

  Gloria Allan John J Lease REALTORS Inc

  715 Stony Ford Rd, Middletown, NY 10941
• 

  

  /30

  $419,000

  • 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
• 

  

  /37

  $369,000

  • 4 Beds
  • 2 Baths
  • 1,408 Sq Ft

  51 Howard Dr, Middletown, NY 10941

  This updated ranch sits on a corner lot and has been tastefully updated with a new kitchen, front and rear decks, and baths in 2020. The home has hardwood floors throughout. The value here is excellent. All you'll need to do is unpack and move in.On the market for the first time in forty-six years, its owners are happy to know another will soon love the home.Located less than 5 minutes to

  Adrienne Volpe Keller Williams Hudson Valley

  51 Howard Dr, Middletown, NY 10941
• 

  

  /24

  $315,000

  • 3 Beds
  • 1.5 Baths
  • 1,778 Sq Ft

  58 Chaucer Ct, Middletown, NY 10941

  Your search ends here with this beautifully maintained 3-bedroom, 1.5-bath home that’s ready for its next owner. Thoughtfully updated and full of charm, this home features gleaming hardwood floors throughout and newer windows that fill each space with abundant natural light.All three bedrooms are generously sized, offering comfortable living and plenty of sunlight. Both bathrooms have

  Matthew O'Hare Coldwell Banker Realty

  58 Chaucer Ct, Middletown, NY 10941
• 

  

  /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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