Colonial Homes for Sale in Middletown, NY

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  $1,680,000

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

  3 Bristol Dr, Middletown, NY 10941

  Welcome to 3 Bristol Drive, a rare brick colonial estate set on 1.4 private acres, offering nearly 8,000 Sqft of living space plus a spectacular 3,200-square-foot indoor pool pavilion designed for year-round enjoyment. Built in 2002, this 6-bedroom suits, 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

  3 Bristol Dr, Middletown, NY 10941
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  /50

  $850,000

  $45K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,296 Sq Ft

  411 Mt Joy Rd, Middletown, NY 10941

  Space, privacy, and thoughtful design come together at this well-maintained 4-bedroom, 2.5-bath Colonial, built in 2005, offers 3,296 sq ft of living space on 11.7 private acres—giving you room to breathe while staying conveniently close to everything Middletown has to offer.Step inside and you'll immediately notice the 9-foot ceilings that elevate every room with an airy, open feel. The main

  

  Donna Reese

  KW Hudson Valley United

  411 Mt Joy Rd, Middletown, NY 10941
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  /26

  $339,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft

  101 N Beacon St, Middletown, NY 10940

  Move in ready 3 bedrooms, 2 bathroom home. Clean and freshly painted. Updated kitchen and bathrooms. Located on a dead end street. Private Fenced-in yard. Conveniently located minutes from local shops, restaurants, Galleria Mall, Garnet Health and close proximity to I86 and I84. Very easy to show. Call today for your own private viewing.

  

  Dulce M Ferrera

  KW Hudson Valley United

  101 N Beacon St, Middletown, NY 10940
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  /48

  $425,000

  $50K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,074 Sq Ft

  57 Boorman Rd, Middletown, NY 10940

  Seller is willing to contribute towards closing costs. Welcome home to this fully renovated Dutch Colonial set on 5+ private acres in the desirable Minisink Valley Central School District, located just minutes from Middletown! Step inside to a beautifully updated kitchen featuring sleek quartz countertops, ceramic tile flooring, a subway tile backsplash, new cabinetry, and stainless steel

  

  Lynelle Alessi

  KW Hudson Valley United

  57 Boorman Rd, Middletown, NY 10940
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  /50

  $550,000

  Open Sat 1PM - 3PM $70K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 3,080 Sq Ft

  179 Reservoir Rd, Middletown, NY 10940

  Warmth, comfort & space in the Hudson Valley. Welcome home to this spacious Colonial on 2.8 acres offering 3–4 bedrooms, 2 full baths, and a detached 2-car garage with oversized loft. The heart of the home is the large family room — cathedral ceilings, a stunning stone fireplace, and beautiful hardwood floors — the perfect place to gather. The private second-floor primary suite has its own full

  

  Dulce M Ferrera

  KW Hudson Valley United

  179 Reservoir Rd, Middletown, NY 10940
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  /41

  $699,900

  New Construction

  • 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

  TBD Kirbytown Rd, Middletown, NY 10940
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  /50

  $999,500

  $101K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,787 Sq Ft

  441 Scotchtown Collabar Rd, Middletown, NY 10941

  Colonial Masterpiece - This one-of-a-kind Hudson Valley residence artfully combines authentic, historic character with flawless contemporary design set on a bucolic, level parcel. The c. 1790’s antique colonial portion of the home features a timeless natural stone facade, standing seam roof, and welcoming red front door evoking true period charm. An architecturally inspired contemporary wing clad

  Jacob Matthews Ellis Sotheby's Intl Realty

  441 Scotchtown Collabar Rd, Middletown, NY 10941
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  $420,500

  • 3 Beds
  • 1.5 Baths
  • 1,656 Sq Ft

  34 Adams Ave, Middletown, NY 10940

  Welcome to this charming 3-bedroom, 1.5-bath Colonial nestled on a level, fenced lot in the heart of Middletown. Built in 1941, this well-maintained home beautifully blends timeless character with everyday functionality, showcasing original hardwood floors, classic woodwork, detailed moldings, and elegant arched doorways throughout. The inviting first floor features a spacious living room, formal

  Linda Potyak Iron Valley RE Tri-State

  34 Adams Ave, Middletown, NY 10940
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  /47

  $739,000

  $60K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,085 Sq Ft

  3 Truman Ct, Middletown, NY 10940

  Step into 5-bedroom Colonial-style home, where classic charm meets upscale upgrades. From the moment you enter, you’re welcomed by exquisite craftsmanship, including detailed crown molding and rich hardwood floors that flow seamlessly throughout the main living spaces.This spacious residence features three elegant fireplaces, creating warm and inviting focal points across multiple living

  Dominick Tufano RE/MAX Benchmark Realty Group

  3 Truman Ct, Middletown, NY 10940
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  /34

  $539,900

  • 4 Beds
  • 2.5 Baths
  • 2,176 Sq Ft

  31 Denman Rd, Middletown, NY 10940

  Welcome to this beautifully maintained Center Hall Colonial offering the perfect blend of classic design and comfortable everyday living. The heart of the home is the spacious kitchen, which opens seamlessly to the inviting family room, creating an ideal space for gathering with family and friends. The family room is highlighted by custom built-in shelving and a cozy wood-burning fireplace,

  Kenyatta Jones-Arietta R2M Realty Inc

  31 Denman Rd, Middletown, NY 10940
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  /34

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  158 Cottage St, Middletown, NY 10940

  Step inside this classic 3-bedroom, 2-bath Colonial and imagine the possibilities. Offering approximately 1,610 square feet, the home features a traditional layout with a living room, formal dining room, spacious kitchen, and a flexible first-floor bonus room that can serve as a den, home office, or recreation space. A dedicated laundry area adds everyday convenience, while the covered front

  Derek Greene Greene Realty Group

  158 Cottage St, Middletown, NY 10940
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  /36

  $585,000

  $15K PRICE DROP

  • 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 lifeA grand foyer opens to a bright, airy layout with high ceilings, large windows,

  Michelle Gruberger Real Estate Circuit Inc

  669 Mountain Rd, Middletown, NY 10940
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  /6

  $799,000

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

  Lot 2 Winters Ln, Middletown, NY 10940

  Welcome to your dream home! This stunning new construction craftsman-style home is now being built on Lot 2 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

  Lot 2 Winters Ln, Middletown, NY 10940
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  $379,000

  • 4 Beds
  • 2 Baths
  • 1,770 Sq Ft

  26 1/2 Ridge St, Middletown, NY 10940

  Beautifully renovated single-family home offering a clean, comfortable layout with thoughtful updates throughout. This residence features 4 spacious bedrooms filled with natural light and a brand-new kitchen equipped with appliances and ample cabinetry. Fresh finishes throughout the home create a bright, move-in-ready feel. Enjoy additional storage space in both the attic and basement, providing

  Cheskel Werzberger Mount Realty

  26 1/2 Ridge St, Middletown, NY 10940
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  /38

  $899,000

  • 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 KW Hudson Valley United

  255 Howells Rd, Middletown, NY 10940
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  $635,000

  $40K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,481 Sq Ft

  5 Decker Dr, Middletown, NY 10940

  Charming Farmhouse Retreat on 2.9 Acres! Nestled on a quiet country road in the Town of Greenville and located within the desirable Minisink Valley Central School District. This beautiful farmhouse-style home offers the perfect blend of comfort, charm, and country living. Inviting home features 3 bedrooms and 2.5 baths with attractive Pergo wood flooring throughout the downstairs, while upstairs

  Dominick Tufano RE/MAX Benchmark Realty Group

  5 Decker Dr, Middletown, NY 10940
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  /32

  $740,000

  • 4 Beds
  • 2.5 Baths
  • 2,733 Sq Ft

  210 Howells Turnpike, Middletown, NY 10940

  Nestled on 2.5 peaceful acres, this colonial-style home has been lovingly cared for by the same owner since it was built in 2006. The dramatic cathedral ceiling foyer welcomes you with a sense of grandeur, opening to a spacious interior filled with natural light. Hardwood floors flow throughout, enhanced by a refreshed staircase with updated balusters and designer lighting. The custom kitchen is

  Cecilia Lewis Century 21 Elite Realty

  210 Howells Turnpike, Middletown, NY 10940
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  /17

  $629,000

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft

  744 Mt Hope Rd, Middletown, NY 10940

  Welcome to this stunning new Colonial home, currently under construction and set on approximately 3 beautiful acres in the desirable Town of Wallkill. Offering approximately 2,600 square feet of finished living space, including a finished basement, this spacious home features 4 bedrooms, 3 full bathrooms, and a one-car garage. The inviting open-concept design showcases gleaming hardwood floors

  Anita S. Cristiano HomeSmart Homes & Estates

  744 Mt Hope Rd, Middletown, NY 10940
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  /35

  $415,000

  • 3 Beds
  • 1 Bath
  • 1,032 Sq Ft

  80 Beattie Ave, Middletown, NY 10940

  Welcome Home to Comfort, Style & Convenience in the Heart of Middletown! This beautifully renovated two-story Colonial blends timeless charm with modern updates, offering the perfect place to call home. Featuring 3 bedrooms, 1 full bathroom, and thoughtfully designed living spaces throughout, this move-in-ready property has been updated to maximize both functionality and style. From the moment

  Sheyla Falesto Howard Hanna Rand Realty

  80 Beattie Ave, Middletown, NY 10940
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  /50

  $310,000

  • 3 Beds
  • 1.5 Baths
  • 1,398 Sq Ft

  4 Lincoln St, Middletown, NY 10940

  This 3-bedroom, 2-bath Colonial offers 1,398 square feet of comfortable living space on a 0.11-acre lot. Built in 1890, the home blends timeless style with thoughtful upgrades while keeping its original charm. Enjoy bright mornings with natural light, cozy evenings at home, and a neighborhood close to shopping, restaurants, parks, schools, and local services. All utilities are available, making

  Matthew Gibbs KW Hudson Valley United

  4 Lincoln St, Middletown, NY 10940
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  /19

  $333,000

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  23 Harrison St Unit 25, Middletown, NY 10940

  Come see this well maintained 2 story colonial style home. Centrally located in the City of Middletown which allows you to be minutes away to all the great eateries and to all major shopping and public transportation. The home has taken a few updates over the years. Home has a spacious living room that leads into a formal dining room. Kitchen has plenty of cabinet space as well. The central a.c

  Pedro Garcia Curasi Realty, Inc.

  23 Harrison St Unit 25, Middletown, NY 10940
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  /39

  $325,000

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  10 Forest Ave, Middletown, NY 10940

  AFFORDABLE COLONIAL HOME with low taxes, two bedrooms, one bathroom, and flexible extra space. This 1,080 sq. ft. home features vinyl siding, municipal services, and natural gas for heat, hot water, and cooking. Enjoy private off-street parking for up to three cars, with curb-cut access from two streets. The home offers classic charm and character, a covered front porch, concrete walkways, and

  George Koudounas RE/MAX Benchmark Realty Group

  10 Forest Ave, Middletown, NY 10940
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  /38

  $675,000

  $54K PRICE DROP

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

  168 Pine Grove Rd, Middletown, NY 10940

  Update - priced to sell! Imagine waking up surrounded by three private acres while still being just minutes from shopping and major commuter routes. This newly built colonial offers the peace of country living without sacrificing convenience. The open-concept kitchen, oversized island, fireplace, spacious primary suite and unfinished basement provide room to grow while giving buyers the

  Leeshai Lemish Panorama Realty

  168 Pine Grove Rd, Middletown, NY 10940
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  /49

  $499,999

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft

  81 Silver Lake Scotchtown Rd Unit 4, Middletown, NY 10940

  Experience modern living in this newly built 3-bedroom, 2.5-bath home designed with comfort and style in mind. Featuring an open floor plan with soaring 10-foot ceilings, this home offers spacious living and entertaining areas filled with natural light. The gourmet kitchen boasts granite countertops, stainless steel appliances, and ample cabinetry, all flowing seamlessly into the main living

  Antoinette Gundersen HomeSmart Homes & Estates

  81 Silver Lake Scotchtown Rd Unit 4, Middletown, NY 10940
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  $799,999

  $50K PRICE DROP

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

  TBD Brook Rd, Middletown, NY 10941

  New Construction LUXURY HOME in Valley Central Schools outside of SCOTCHTOWN! "Choose Your Finishes" on this Stunning 3,000 sq. ft. modern Colonial privately set atop a scenic 5-acre wooded lot offering privacy and natural beauty. Conveniently located 5-10 minutes to Middletown, Pine Bush, and Montgomery. The main level features a spacious open-concept floor plan with 9-foot ceilings, hardwood

  Philip Barnao eXp Realty

  TBD Brook Rd, Middletown, NY 10941
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  /41

  $749,900

  • 4 Beds
  • 2.5 Baths
  • 2,906 Sq Ft

  512 County Route 49, Middletown, NY 10940

  Welcome to this stunning, meticulously maintained Chesterfield Colonial offering breathtaking views, exceptional updates, and true move-in-ready condition. From the moment you enter the impressive two-story foyer, you'll appreciate the bright, open-concept design and abundance of natural light streaming through every window. The spacious main living areas are perfect for both everyday living and

  Jonathon Lee KW Hudson Valley United

  512 County Route 49, Middletown, NY 10940
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  /49

  $529,000

  • 3 Beds
  • 2.5 Baths
  • 2,504 Sq Ft

  37-39 Wisner Ave, Middletown, NY 10940

  Welcome to this beautifully remodeled 3-4 bedroom, 3-bath Colonial situated on a rare double lot at 37-39 Wisner Avenue in Middletown. Move-in ready and thoughtfully updated, this spacious home offers modern comforts, flexible living space, and exceptional outdoor parking and yard areas rarely found within the city. The main level features a generously sized living room, formal dining room, and a

  Jonathon Lee KW Hudson Valley United

  37-39 Wisner Ave, Middletown, NY 10940
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  /2

  $469,000

  Coming Soon

  • 5 Beds
  • 3 Baths
  • 2,448 Sq Ft

  495 Guymard Turnpike, Middletown, NY 10940

  Welcome home to this breathtaking Farmhouse-style retreat, perfectly set back from the main road amidst mature hydrangeas and Rose of Sharon. Step onto the sprawling, large rocking chair front porch—part of an expansive covered porch that wraps around three sides of the home—and experience true rustic charm before you even step inside. Upon entry, you’ll be in awe of the soaring vaulted ceilings,

  Maureen Cronin Cronin & Company Real Estate

  495 Guymard Turnpike, Middletown, NY 10940
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  /41

  $699,000

  $130K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,340 Sq Ft

  571 Route 17m, Middletown, NY 10940

  Steeped in character and timeless appeal, this 1930 Colonial invites you in with its striking stone facade and a graceful partial wrap-around porch—an ideal spot to enjoy quiet mornings or unwind at the end of the day. Inside, the home blends classic craftsmanship with modern comfort, featuring rich wooden floors that flow seamlessly throughout the main level.The first floor offers a warm and

  Angela Murphy BHG Real Estate Green Team

  571 Route 17m, Middletown, NY 10940
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  $478,000

  • 4 Beds
  • 2 Baths
  • 1,770 Sq Ft

  25 Independence Ave, Middletown, NY 10940

  It is located in one of Middletown's most desirable neighborhoods, where strong demand and steadily increasing home values make this an exceptional opportunity!This beautifully renovated, move-in-ready 4-bedroom home has been thoughtfully updated from top to bottom. The brand-new kitchen features modern cabinetry, a new stove, and an added pantry/storage closet, creating a stylish and

  Jin Pang Panorama Realty

  25 Independence Ave, Middletown, NY 10940
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  /50

  $489,900

  Open Sat 11:30AM - 1PM $6K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,899 Sq Ft

  6 Avoncroft Ln, Middletown, NY 10940

  Beautiful and well maintained single family townhouse located in the desirable community of Woodside Knolls This modern and spacious residence offers comfortable and spacious living across three floors & 2500 sq.ft! The 3 Bedroom, 2.5 Bathroom floor plan includes a luxurious primary bedroom with oversized walk in closets , en suite bathroom with full stand up shower and soaker tub. An additional

  Darnell Williams R New York

  6 Avoncroft Ln, Middletown, NY 10940
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  /6

  $799,000

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

  76 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

  76 Winters Ln, Middletown, NY 10940
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  /33

  $499,999

  Open House 8/15

  • 4 Beds
  • 2 Baths
  • 1,861 Sq Ft

  678 Prosperous Valley Rd, Middletown, NY 10940

  Welcome to 678 Prosperous Valley Road, a beautifully renovated Colonial nestled on 0.80 acres in the desirable Town of Middletown. Combining timeless character with modern upgrades, this move-in-ready home offers 4 spacious bedrooms, 2 full bathrooms, and approximately 1,861 square feet of thoughtfully updated living space. Recent improvements include a stunning remodeled kitchen, fully renovated

  Yonauris Gonzalez Then eXp Realty

  678 Prosperous Valley Rd, Middletown, NY 10940
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  /49

  $765,000

  • 4 Beds
  • 3 Baths
  • 3,064 Sq Ft

  118 Ridge Dr, Middletown, NY 10940

  Timeless Character. Endless Possibilities.Nestled on over 12 private, wooded acres along a quiet country road, this stately brick Colonial offers the rare opportunity to own a home where history, craftsmanship, and natural beauty come together. Built circa 1900 and encompassing more than 3,000 square feet, this remarkable residence is filled with the warmth and architectural character that

  Patricia Sassi RE/MAX Benchmark Realty Group

  118 Ridge Dr, Middletown, NY 10940
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  /50

  $850,000

  • 4 Beds
  • 4.5 Baths
  • 4,522 Sq Ft

  232 Tally Ho Rd, Middletown, NY 10940

  A Rare Country Estate Rich in History, Character & Timeless Beauty. Nestled off the road and surrounded by approximately 17 private, wooded acres, this remarkable circa 1820 estate offers an extraordinary opportunity to own a piece of Hudson Valley history. Lovingly expanded over generations while preserving its original character, this one of a kind residence encompasses over 4,500 square feet

  Patricia Sassi RE/MAX Benchmark Realty Group

  232 Tally Ho Rd, Middletown, NY 10940
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  /40

  $354,900

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  41 Roosevelt Ave Unit 39, Middletown, NY 10940

  Welcome home to this beautifully maintained 3-bedroom, 1-bath Colonial in the City of Middletown. Conveniently located near shopping, restaurants, parks, schools, and major commuter routes, this home blends classic charm with practical everyday living. From the moment you arrive, you'll be drawn to the expansive wraparound front porch—the perfect place to enjoy your morning coffee or unwind at

  Patricia Sassi RE/MAX Benchmark Realty Group

  41 Roosevelt Ave Unit 39, Middletown, NY 10940
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  /50

  $599,900

  • 4 Beds
  • 1.5 Baths
  • 3,280 Sq Ft

  22 Camp Orange Rd, Middletown, NY 10941

  Cherished through generations and lovingly maintained by its owners, this remarkable circa home is ready for its next chapter. Set on 3.6 beautifully level acres in the Valley Central School District, the property offers the perfect blend of historic character, functional space, and country charm. As you approach, the care and pride of ownership are immediately evident. A welcoming front porch

  Rosalie Cook Weichert Realtors

  22 Camp Orange Rd, Middletown, NY 10941
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  /45

  $795,000

  $30K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,276 Sq Ft

  34 Stapleton Ct, Middletown, NY 10940

  Seller ready to go! This stunning four-bedroom Colonial is nestled on 1.3 acres at the end of a peaceful cul-de-sac, backing up to the scenic Hunter Nature Preserve. Solar panels owned, utility bills less than $25/month. Enjoy relaxing evenings on the spacious rocking chair front porch. The updated kitchen features beautiful granite countertops and a custom backsplash, perfect for culinary

  Annie Hansen Howard Hanna Rand Realty

  34 Stapleton Ct, Middletown, NY 10940
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  /2

  $283,000

  $70K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,545 Sq Ft

  187 Watkins Ave, Middletown, NY 10940

  Opportunity knocks in New York. Located near Sprucegate Farm, Swim King, and Magnanini Winery. This home has approx. 1,545 sq. ft. and a lot of approx. 7,750 sq. ft. A great investment opportunity. Buyers check with City, County, Zoning, Tax, and other records to their satisfaction. AS-IS SALE property.

  Neven Spralja Realhome Services & Solutions, Inc

  187 Watkins Ave, Middletown, NY 10940
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  /32

  $610,000

  • 4 Beds
  • 2.5 Baths
  • 2,561 Sq Ft

  320 White Bridge Rd, Middletown, NY 10940

  Discover the perfect blend of peaceful country living and modern comfort at this turnkey Colonial, privately nestled on 5.8 picturesque acres in the Town of Mount Hope within the highly sought after Minisink Valley School District. Welcome to 320 White Bridge Road, where privacy, natural beauty, and comfort come together to create an exceptional place to call home.A dramatic two story foyer

  Frank Muccari Cronin & Company Real Estate

  320 White Bridge Rd, Middletown, NY 10940

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