Middletown, NY Homes for Sale with AC

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  /32

  $1,799,000

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

  3 Bristol Dr, Middletown, NY 10941

  Welcome to 3 Bristol Road, a rare brick colonial estate set on 1.4 private acres, offering nearly 8,000 square feet of living space plus a spectacular 3,200-square-foot indoor pool pavilion designed for year-round enjoyment.Built in 2002, this 6-bedroom, 8.55-bathroom residence features expansive, light-filled interiors and estate-scale proportions ideal for both entertaining and everyday

  

  Mohamed Elgoarany

  All American Realty Management

  (329) 215-0309

  3 Bristol Dr, Middletown, NY 10941
• Explore Middletown

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  /24

  $369,000

  • 4 Beds
  • 3.5 Baths
  • 1,692 Sq Ft

  19 Red Barn Ln, Middletown, NY 10940

  Investment Opportunity! This conveniently located 3-level townhouse. Located on a cul de sac, this 4 bedroom, 3 1/2 baths provides plenty of space. First floor features a living room, eat in kitchen and a walk-in pantry and1/2 bath while the fully finished basement offers a den, bedroom and full bathroom with its own entry. On the 3rd floor you will find the primary bedroom with full bathroom and

  

  Sharon Reynolds

  Keller Williams Hudson Valley

  (329) 219-1188

  19 Red Barn Ln, Middletown, NY 10940
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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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  /25

  $389,000

  • 2 Beds
  • 1.5 Baths
  • 1,346 Sq Ft

  36 Vincent Dr, Middletown, NY 10940

  This home is located in a desirable neighborhood in Middletown, this beautifully maintained home offers the perfect blend of comfort, space, and convenience. Step inside to find a bright and inviting layout featuring spacious living areas, abundant natural light, and a seamless flow ideal for both everyday living and entertaining.The home boasts a well-appointed kitchen with ample cabinetry

  

  Donna Reese

  Keller Williams Hudson Valley

  (329) 210-1922

  36 Vincent Dr, 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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  /41

  $699,900

  • 4 Beds
  • 2.5 Baths
  • 2,174 Sq Ft

  TBD Kirbytown Rd, Middletown, NY 10940

  Welcome to your brand-new home, located on a 2.4 acre wooded lot in the Minisink Valley school district. The Reese model colonial was thoughtfully designed, offering 4 bedrooms and 2.5 baths with plenty of space to grow and make memories. On the first floor, you’ll find a bright and inviting living room with beautiful hardwood floors and a cozy fireplace—perfect for movie nights or gathering with

  

  Chris Ogden

  Realty Promotions Inc

  (329) 209-9962

  TBD Kirbytown Rd, Middletown, NY 10940
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  /22

  $469,000

  • 3 Beds
  • 2 Baths
  • 2,056 Sq Ft

  171 High Barney Rd, Middletown, NY 10940

  Welcome to 171 High Barney a charming three-bedroom, two-bath home tucked away on a quiet dead-end street just before the cul-de-sac. This inviting property offers a bright, cozy living room and a modern kitchen equipped with stainless steel appliances, quartz countertops, and plenty of cabinet space. The lower level features a spacious family room along with bonus space ideal for a home office,

  

  Haakim Byrd

  HomeSmart Homes & Estates

  (329) 201-4415

  171 High Barney Rd, Middletown, NY 10940
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  /50

  $829,000

  • 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

  (329) 208-2931

  3 Kings Dr, Middletown, NY 10941
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  /22

  $329,000 Open Sat 12PM - 3PM

  • 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 Open Sat 11AM - 1PM

  • 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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  /38

  $979,900

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  255 Howells Rd, Middletown, NY 10940

  Enter the gates of this remarkable 36.8-acre estate to discover a distinguished 5-bedroom, 5-bathroom residence offering 4,200 square feet of living space. The property includes a substantial two-story post-and-beam barn with horse stalls, multiple wells, and an additional hay barn—ideal for equestrian or agricultural use. A serene natural pond and a mix of rolling pastures and wooded areas

  Jonathon Lee Keller Williams Hudson Valley

  255 Howells Rd, Middletown, NY 10940
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  /48

  $900,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 3 Baths
  • 4,090 Sq Ft

  464 Union School Rd, Middletown, NY 10941

  Nestled on a private 5.1-acre property, this custom contemporary Cape-style home offers the perfect balance of luxury, comfort, and natural beauty. Thoughtfully designed with refined finishes and exceptional living spaces, this residence creates an inviting retreat while still being close to the many attractions of the Hudson Valley. Step inside to discover a bright and spacious main level

  Colin Seitz RE/MAX Benchmark Realty Group

  464 Union School Rd, Middletown, NY 10941
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  /43

  $499,000 Open Sat 12PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft

  7 Gene Rd, Middletown, NY 10941

  Welcome to this beautifully updated 4-bedroom, 2.5-bath raised ranch offering a versatile and comfortable layout. The main level features bright and inviting living spaces, while the lower level includes a spacious recreation room and additional family/multi-purpose room—ideal for a variety of lifestyle needs. Enjoy an expansive backyard and generous deck space, perfect for outdoor relaxation or

  Joseph Lukic Compass Greater NY, LLC

  7 Gene Rd, Middletown, NY 10941
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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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  /46

  $618,000

  • 3 Beds
  • 2.5 Baths
  • 1,977 Sq Ft

  70 King Rd, Middletown, NY 10941

  Welcome to a truly special property, a wonderful home that combines style, comfort, and a park-like location. Close to all Middletown has to offer. The heart of the home is the living room — this sunny room features a fireplace, hardwood floors, and a cathedral ceiling, making it the perfect place to retreat to after sharing a meal in the connected dining room. Cooking in the new kitchen on the

  Jeanine Stoddard Coldwell Banker Village Green

  70 King Rd, Middletown, NY 10941
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  /47

  $475,000 Open Sat 11AM - 2PM

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

  59 Meadow View Dr, Middletown, NY 10940

  This beautiful 3 bed 2 1/2 bath townhome is nestled in the heart of Middletown with so much to offer and just minutes from transportation to and from NYC. Upon entering you'll find beautiful hardwood floors throughout the first floor. An open floor plan including a sun drenched living room with a full glass door leading to a very spacious deck for outdoor grilling and relaxation. Just opposite

  Kevin Grier Keller Williams Hudson Valley

  59 Meadow View 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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  /21

  $560,000

  • 4 Beds
  • 3 Baths
  • 2,162 Sq Ft

  77 Upper Rd, Middletown, NY 10940

  This beautiful ranch-style property is ready to move in. Amazing upgrades were made to this home with beautiful hardwood floors, 4 bedrooms, 3 bathrooms, a huge finished basement with 3 additional rooms for storage or home office, and it also has space for a personal gym with access to an amazing backyard that features a beautiful above-ground pool, a tennis court, volleyball court, or basketball

  Yajaira Silva Madison Allied LLC

  77 Upper Rd, 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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  /13

  $560,000

  • 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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  /30

  $289,000

  • 2 Beds
  • 2 Baths
  • 1,049 Sq Ft

  185 Ruth Ct, Middletown, NY 10940

  INVESTOR'S DREAM: TURN-KEY CONDO WITH IMMEDIATE CASH FLOW! This meticulously maintained 2-bedroom, 2-full bath end-unit condo is an absolute standout in one of Middletown's most sought-after communities. Recently upgraded with fresh paint and brand-new flooring in late 2024, the property also features a new central AC condenser installed in 2025, ensuring long-term mechanical reliability. The

  Hai Li Keller Williams Hudson Valley

  185 Ruth Ct, Middletown, NY 10940
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  /28

  $489,999

  • 3 Beds
  • 2.5 Baths
  • 1,832 Sq Ft

  20 Tammy Dr, Middletown, NY 10941

  LOCATION,LOCATION,LOCATION CLOSE TO WALMARTTHE METRO NORTH TRAIN STATION TO NYC, Abundance of Dining and Grocery options, The Galleria Mall, Garnet Medical Center, Major Highways Route 17M & Interstate I84, Home has 3 bedrooms and 2.5 bathrooms, Stainless Steel Appliances, Granite counter top with a breakfast nook., Hardwood Floor, En-suite bathroom in master bedroom, Large deck on upper level

  Sol Perry BHG Real Estate Green Team

  20 Tammy Dr, Middletown, NY 10941
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  /35

  $599,900

  • 6 Beds
  • 3.5 Baths
  • 2,948 Sq Ft

  669 Mountain Rd, Middletown, NY 10940

  Country Escape of 6 spacious bedrooms offers space, privacy, and a serene setting on 3.38 acres. Just about 75 miles from New York City, it’s close enough for convenient weekend escapes yet far enough to feel like a true retreat feels like a private estate—perfect for those seeking a refined escape from city life A grand foyer opens to a bright, airy layout with high ceilings, large windows, and

  Michelle Gruberger Real Estate Circuit Inc

  669 Mountain Rd, Middletown, NY 10940
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  /17

  $629,000

  • 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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  /7

  $799,000

  • 4 Beds
  • 3.5 Baths
  • 2,696 Sq Ft

  1 Winters Ln, Middletown, NY 10940

  Welcome to your dream home! This stunning new construction craftsman-style home is now being built on Lot 1 of the coveted Lane Meadow Farm subdivision, located in the Town of Mamakating, Sullivan County, NY. Enjoy the serenity and natural beauty of one of Sullivan County's newest and most sought-after neighborhoods, where peaceful country living meets exceptional craftsmanship. Featuring

  Jacob Silberstein Parcel Realty LLC

  1 Winters Ln, Middletown, NY 10940
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  /43

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  50 Brola Rd, Middletown, NY 10940

  Bring your vision to life at 50 Brola Road. Perfectly situated in the picturesque countryside within the Minisink school district you will find a tremendous opportunity. The home itself offers a spacious and open floor plan along with ample parking, fenced rear yard, plenty of storage space and room for expansion. There is a building lot to the right of the property that can be purchased for a

  Nicholas Carbone HomeSmart Homes & Estates

  50 Brola Rd, Middletown, NY 10940
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  /8

  $490,000 Open Sat 1PM - 3PM

  • 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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  /19

  $535,000

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

  19 Sunflower St, Middletown, NY 10940

  GATED COMMUNITY – FOR ACCESS: On arrival, look up BRODSKY at the front gate callbox for gate authorization and entry. As the only property currently available in the highly desirable Wildflowers 55+ gated community, this meticulously maintained, single-level home offers a perfect blend of modern upgrades and resort-style living. Recent updates include new interior paint, a true walk-in shower, a

  David White Owner Entry.com

  19 Sunflower St, Middletown, NY 10940
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  /27

  $574,999

  • 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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  /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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  /47

  $489,998

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

  131 Meadow View Dr, Middletown, NY 10940

  Welcome to this beautifully maintained 3-bedroom, 2.5-bath end-unit three-level townhouse in the highly desirable Maple Fields community! Step inside to find gleaming hardwood floors throughout the main level, creating a warm and inviting space perfect for everyday living and entertaining. The lower level and second floor feature easy-to-care-for luxury vinyl plank flooring, offering both

  Karleen Jedziniak Howard Hanna Rand Realty

  131 Meadow View Dr, 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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  /23

  $344,900

  • 4 Beds
  • 1.5 Baths
  • 1,598 Sq Ft

  16 Mountain Ave, Middletown, NY 10940

  Welcome to 16 Mountain Ave — a well-loved home with tons of potential in the heart of town! This spacious 4-bedroom, 1.5-bath Colonial offers the perfect blend of solid maintenance and room to make it your own. An estate property that’s been cared for throughout the years, it features original hardwood floors waiting to shine beneath the carpet, central air, and a layout that truly works for

  Valerie Jewis Keller Williams Realty

  16 Mountain 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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  /24

  $439,900 Open Sun 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,905 Sq Ft

  566 County Route 49, Middletown, NY 10940

  For Sale – 566 County Route 46, Middletown, NY 10940 Welcome to this spacious 3-bedroom, 4-bath colonial-style condo located in a quiet country setting in Middletown. This home is the largest unit in the 4-unit condo complex, offering generous living space and a comfortable layout. The first floor features a bright and inviting large living room with sliding doors leading to a rear deck, perfect

  Jonathon Lee Keller Williams Hudson Valley

  566 County Route 49, 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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  /19

  $479,999

  • 6 Beds
  • 2 Baths
  • 2,424 Sq Ft

  80 Prospect Ave, Middletown, NY 10940

  Welcome to 80 Prospect Ave, a well-maintained six-bedroom, two-bathroom home situated in the peaceful suburban setting of Middletown, NY. Built in 1918, this 2,424 square foot residence combines traditional architectural charm with modern updates, offering nearly 6,800 square feet of usable lot space ideal for both living and outdoor enjoyment. The property features a classic two-story design

  Jonathan Paredes Locqube New York, Inc.

  80 Prospect Ave, Middletown, NY 10940
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  /18

  $429,000

  • 3 Beds
  • 2.5 Baths
  • 2,097 Sq Ft

  4 Kless Ct, Middletown, NY 10940

  Welcome to this well-kept 3-bedroom home with a bonus loft, set in the Maple Fields community. The first floor offers an easy, open layout with a comfortable living area that leads out to a private patio, along with a dining space and a kitchen that includes a pantry, tile accents, and stainless steel appliances. Upstairs you’ll find the primary bedroom featuring a walk-in closet and its own

  Bryant Moran YourHomeSold Guaranteed Realty

  4 Kless Ct, Middletown, NY 10940
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  /26

  $150,000

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

  79 Stern Scenic Dr, Middletown, NY 10940

  Welcome to this updated 3-bedroom, 2-bath double-wide mobile home offering comfort, space, and convenience in Middletown. Recent updates enhance both style and functionality, while the open and spacious layout provides plenty of room to relax or entertain. The primary bedroom features a private bath, and the additional bedrooms are generously sized. Conveniently located near local shopping,

  Ivan Carvalho Exit Realty Connections

  79 Stern Scenic Dr, Middletown, NY 10940

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