Newest Homes for Sale in Middletown, NY

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  /39

  $249,999 Open Sat 11AM - 1PM

  • 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
• Explore Middletown

• 

  

  

  /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
• 

  

  

  /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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  /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
• 

  

  

  /43

  $499,000 Open Sat 2PM - 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
• 

  

  /23

  $435,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  47 Liberty St, Middletown, NY 10940

  Updated 3BR/2BA Home on Quiet Dead-End Street – Middletown Updated 3-bedroom, 2 full-bath home located on a dead-end street in the City of Middletown. First floor features a spacious eat-in kitchen with stainless steel appliances, large living room, dining area, and updated full bath. Sliding door off kitchen leads to backyard deck. Second floor offers 3 bedrooms and an updated full bath, plus

  Jonathon Lee Keller Williams Hudson Valley

  47 Liberty St, Middletown, NY 10940
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  /45

  $400,000

  • 8 Beds
  • 3 Baths
  • 2,121 Sq Ft

  29 Columbia Ave, Middletown, NY 10940

  Charming 1923 Traditional – Spacious 8-Bedroom Home with Timeless Character Step into a rare opportunity to own a beautifully expansive 3-story traditional home built in 1923, offering over 2,100 square feet of versatile living space. Brimming with classic charm and endless potential, this 8-bedroom, 3-bathroom residence is perfect for those seeking room to grow, host, or simply relax. Inside,

  Sharon Pehush HomeSmart Homes & Estates

  29 Columbia Ave, Middletown, NY 10940
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  /10

  $379,900 Open Sat 1PM - 3PM

  • 3 Beds
  • 3 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
• 

  

  /44

  $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
• 

  

  /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
• 

  /2

  $480,000

  1 Royce Ave, Middletown, NY 10940

  Excellent investment opportunity in the heart of Middletown! This well-maintained, fully occupied two-family residence offers immediate cash flow with a total monthly income of $3,500. The first-floor unit features a comfortable 1-bedroom, 1-bathroom layout currently rented for $1,600, while the second-floor unit offers a spacious 2-bedroom, 1-bathroom configuration rented for $1,900.

  Joseph Baratta Joseph Baratta Company Realty

  1 Royce Ave, Middletown, NY 10940
• 

  

  /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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  /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

  • 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
• 

  

  /20

  $335,000

  • 2 Beds
  • 1 Bath
  • 976 Sq Ft

  1110 New York 211, Middletown, NY 10940

  If you are looking for one-level living, this is the one! This 2-bedroom ranch is the perfect opportunity for a first-time homebuyer, someone looking to downsize, or an investor seeking to add to their rental portfolio. Filled with natural light, the home offers a bright and inviting atmosphere throughout. The spacious primary bedroom features a large wall-to-wall closet. A combination of

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (329) 208-3782

  1110 New York 211, Middletown, NY 10940
• 

  

  /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
• 

  

  /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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  /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
• 

  /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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  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /40

  $509,900

  • 4 Beds
  • 3 Baths
  • 2,052 Sq Ft

  127 Sproat St, Middletown, NY 10940

  There is a reason a raised ranch continues to stand the test of time... it just lives right. From the moment you step inside this move-in ready 4 bedroom, 3 bathroom home in Middletown, you feel the ease of a layout designed for real life. Head upstairs and you are immediately welcomed into a bright, open living space where natural light pours in and hardwood floors carry warmth throughout. The

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (329) 210-2066

  127 Sproat St, Middletown, NY 10940
• 

  /2

  $90,000

  • 1 Bath
  • 480 Sq Ft

  109 Concord Ln, Middletown, NY 10940

  Studio apartment

  Malik Subhani Weichert Realtors

  109 Concord Ln, Middletown, NY 10940
• 

  

  /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
• 

  

  /13

  $290,000

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  3 Top Notch Rd, Middletown, NY 10940

  This ranch-style home sits on a sizable lot with a practical single-level floor plan. The property offers potential and solid foundation for the right buyer. The property sits on a secluded wooded lot with mature evergreen borders that create natural privacy year-round. The private wooded backyard provides a peaceful retreat with considerable potential for outdoor activities and relaxation. A

  Andrea Rose Keller Williams Hudson Valley

  3 Top Notch Rd, Middletown, NY 10940
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  /36

  $509,999

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

  612 Shoddy Hollow Rd, Middletown, NY 10940

  Welcome to 612 Shoddy Hollow Road, a beautifully maintained 4 bedroom, 3 full bathroom raised ranch tucked away in sought after Mount Hope. This inviting home offers the perfect blend of comfort, space, and functionality. Upon entry, you’re greeted by a bright, open concept living room that seamlessly flows to a spacious deck overlooking the property ideal for relaxing or entertaining. The cozy

  Alexander Fayn Prominent Properties Sotheby's

  612 Shoddy Hollow Rd, Middletown, NY 10940
• 

  

  /17

  $119,888

  • 3 Beds
  • 2 Baths
  • 1,599 Sq Ft

  32 Abraham Joseph Cir, Middletown, NY 10940

  Move right in to a quiet place, a mobile/manufactured home. This lovely 3 Bedroom 2 Bath home in the Minisink school district, with vaulted ceilings, a large deck, Hardwood floors, and parking off the street.HOA maintenance fees are $780 per month, which includes water, sewer, garbage removal, taxes, and maintenance of main roads."Main roads, 20 minutes to the Galleria

  Joseph Lombardo Listing by Lombardo Homes & Estates

  

  32 Abraham Joseph Cir, Middletown, NY 10940
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /25

  $399,900

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  56 Mulberry St Unit 54, Middletown, NY 10940

  CALLING ALL INVESTORS! This well-maintained two-family home in the heart of Middletown is a must-see opportunity! Each apartment offers two bedrooms, a spacious living room, a den/office and a full kitchen, perfect for tenants seeking comfort and convenience. Recent updates include a new roof, siding, soffits, and gutters—all completed within the past few months, ensuring peace of mind for years

  Patricia Sassi RE/MAX Benchmark Realty Group

  56 Mulberry St Unit 54, Middletown, NY 10940
• 

  

  /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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