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Colonial Homes for Sale in Middletown, NY

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  • /32

    $1,700,000

    $188K PRICE DROP
    • 5 Beds
    • 9 Baths
    • 7,794 Sq Ft

    3 Bristol Dr, Middletown, NY 10941

    PRICE REDUCTION FOR FASTER SALE...OWNER RELOCATING.....HURRY UP....WILL NOT LAST.............................Welcome to 3 Bristol Road, 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, 8.55-bathroom residence features

    Agent Photo

    Mohamed Elgoarany

    All American Realty Management

    (329) 215-0309

    3 Bristol Dr, Middletown, NY 10941
  • /44

    $450,000

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,074 Sq Ft

    57 Boorman Rd, Middletown, NY 10940

    Renovated Dutch Colonial on 5+ private acres in the Minisink school district, just minutes from Middletown!Updated kitchen features quartz countertops, ceramic tile flooring, subway tile backsplash, new cabinetry, and stainless steel appliances. First floor offers a full bath, spacious living room, dining room, and a cozy wood stove for supplemental heat. Upstairs includes 3 bedrooms and a

    Agent Photo

    Lynelle Alessi

    Keller Williams Hudson Valley

    (329) 212-0455

    57 Boorman Rd, Middletown, NY 10940
  • /50

    $599,900

    $20K 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

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (329) 207-0914

    179 Reservoir Rd, Middletown, NY 10940
  • /2

    $599,900

    • 6 Beds
    • 2 Baths
    • 3,190 Sq Ft

    215 Linden Ave, Middletown, NY 10940

    Excellent investment opportunity in the City of Middletown! This well-maintained duplex features two spacious 3-bedroom, 1-bath units, each offering generous living space and separate utilities. Both units include an oven and refrigerator, with tenants responsible for utilities, providing strong income potential for investors or owner-occupants alike. Finished walk-up attics also provide

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (329) 213-1735

    215 Linden Ave, Middletown, NY 10940
  • /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

    Agent Photo

    Chris Ogden

    Realty Promotions Inc

    (329) 209-9962

    TBD Kirbytown Rd, Middletown, NY 10940
  • /17

    $399,900

    • 3 Beds
    • 2.5 Baths
    • 1,792 Sq Ft

    8 Walnut Ln, Middletown, NY 10940

    Opportunity knocks in one of Middletown's most convenient and desirable locations! This spacious 3 bedroom, 2.5-bath Colonial with a 2-car garage offers the perfect blend of size, location and potential. Featuring hardwood floors, a functional layout, and a kitchen equipped with stainless steel appliances and granite countertops, this home provides an excellent foundation for creating your own

    Bonnie Natt Realty Promotions Inc

    8 Walnut Ln, Middletown, NY 10940
  • /48

    $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
  • /50

    $2,695,000

    • 5 Beds
    • 4.5 Baths
    • 20,730 Sq Ft

    285 Hill Rd, Middletown, NY 10940

    For your consideration is 285 Hill Road, a premier equine boarding, training and showing facility formerly known as Hilltop Equestrian Center and Seven Meadows Farm. Designed for function and beauty, it's a welcoming destination for both clients and guests. Numerous shows and clinics have been successfully hosted here over the years. The property includes a professional indoor arena complex, 2

    Michelle Genatempo Howard Hanna Rand Realty

    285 Hill Rd, Middletown, NY 10940
  • /49

    $799,000

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

    3 Truman Ct, Middletown, NY 10940

    Step into refined living with this beautifully maintained 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

    Dominick Tufano RE/MAX Benchmark Realty Group

    3 Truman Ct, Middletown, NY 10940
  • /28

    $434,999

    • 3 Beds
    • 2 Baths
    • 1,614 Sq Ft

    9 Chestnut St, Middletown, NY 10940

    Move in ready Colonial that perfectly balances classic charm with tasteful updates. This home has been meticulously maintained and features a bright, inviting interior. The kitchen serves as the heart of the home, updated with white shaker cabinets, granite countertops, an oversized island, and a full suite of stainless steel appliances. For added convenience, the first floor includes a dedicated

    Christian Lugo Howard Hanna Rand Realty

    9 Chestnut St, Middletown, NY 10940
  • /41

    $479,000

    • 3 Beds
    • 2.5 Baths
    • 2,228 Sq Ft

    217-219 Highland Ave, Middletown, NY 10940

    Spacious and charming 3-bedroom, 2.5-bath home featuring a welcoming wraparound porch and an abundance of living space throughout. The main level offers an entry foyer, living room, formal dining room, kitchen, family room, den, powder room, and laundry room. Upstairs features a primary bedroom with private bath, two additional bedrooms, and a full hall bathroom. The walk-up third level offers

    Wenpeng Guan Keller Williams Hudson Valley

    217-219 Highland Ave, Middletown, NY 10940
  • /47

    $349,999

    • 3 Beds
    • 4 Baths
    • 1,854 Sq Ft

    36 Prospect St, Middletown, NY 10940

    This beautiful colonial-style home is in need of some TLC! Due to its status as a Short Sale, the property is being sold “As-Is” with subject approval from a third party. This charming property boasts four bedrooms, two full baths, a well-equipped kitchen, a formal dining and living room, an unfinished basement and attic, a private driveway, and a spacious lot. Whether you’re an investor or a

    Vladimir Charles-Pierre Our Community Realty Ltd

    36 Prospect St, Middletown, NY 10940
  • /25

    $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
  • /48

    $949,500

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

    411 Mt Joy Rd, Middletown, NY 10941

    Privacy, space, and convenience come together beautifully in this 3,296 sq ft Colonial set on 11.7 acres. This spacious home features 4 bedrooms plus a private office/possible 5th bedroom with French doors, 2.5 baths, central air, hardwood floors, and a 2-car garage. The inviting family room offers a wood-burning fireplace, while the kitchen includes stainless steel appliances and a double oven.

    Patricia Lucey Picture It Sold, LLC

    411 Mt Joy Rd, Middletown, NY 10941
  • /36

    $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
  • /50

    $529,999

    • 4 Beds
    • 2.5 Baths
    • 2,486 Sq Ft

    8 Wayne Ct, Middletown, NY 10941

    Welcome to this beautifully maintained Colonial conveniently located in the sought-after Town of Wallkill community just 1.5 hours north of NYC! Offering over 2,400 square feet of living space, this original owner property provides the blend of comfort and convenience fit for everyday living. Its open entryway invites you into the home with high ceilings and hardwood floors throughout. The

    Tehillah Deslandes Howard Hanna Rand Realty

    8 Wayne Ct, Middletown, NY 10941
  • /33

    $649,000

    $26K 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
  • /49

    $589,900

    • 3 Beds
    • 2.5 Baths
    • 2,192 Sq Ft

    311 New Vernon Rd, Middletown, NY 10940

    Nestled well off the road amid mature landscaping and expansive lawn, this custom Colonial offers a rare combination of privacy, space, and pride of ownership. Built and meticulously maintained by its original owners, the home reflects years of thoughtful updates and careful stewardship. Inside, hardwood floors extend throughout the home, creating warmth and continuity from room to room. Custom

    Patricia Sassi RE/MAX Benchmark Realty Group

    311 New Vernon Rd, Middletown, NY 10940
  • /35

    $415,000

    Open Wed 6PM - 8PM
    • 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
  • /12

    $210,000

    Pre-Foreclosure
    • 3 Beds
    • 1.5 Baths
    • 1,320 Sq Ft

    8 Grant St, Middletown, NY 10940

    Here's the opportunity investors have been waiting for. This two-story colonial offers the right buyer a full-renovation canvas with real upside. Generous room sizes, hardwood floors on the upper level, a covered front porch, and an oversized barn/garage outbuilding in the rear — features that support strong ARV whether you're flipping or holding for rental income. The home needs a complete

    Igor Krasnoperov Rising Star Realty

    8 Grant St, Middletown, NY 10940
  • /47

    $1,249,000

    • 3 Beds
    • 2.5 Baths
    • 4,225 Sq Ft

    2 White Horse Rd, Middletown, NY 10940

    Offered for sale for the very first time by its original owners, this custom-designed and thoughtfully upgraded 3-bedroom, 2.5-bath private luxury estate is nestled on 12.7 level acres in the Town of Greenville. Built in 2014 with quality craftsmanship and comfort in mind, this expansive home offers the perfect blend of space, functionality, and modern efficiency. The chef’s kitchen outfitted

    Vanessa Wight BHG Real Estate Green Team

    2 White Horse Rd, Middletown, NY 10940
  • /25

    $390,000

    • 4 Beds
    • 2 Baths
    • 1,652 Sq Ft

    21 Albert St, Middletown, NY 10940

    Charming 4-bedroom, 2-bath home in the heart of Middletown offering space, character, and endless potential! Nestled on a sidewalk-lined street, this property features a welcoming wraparound porch — the perfect spot to relax. Step inside the inviting foyer and into a spacious living room adjacent to the dining room and kitchen featuring a center island, with bathroom conveniently located on the

    Christina Wilger RE/MAX Benchmark Realty Group

    21 Albert St, Middletown, NY 10940
  • /46

    $550,000

    • 4 Beds
    • 2.5 Baths
    • 2,069 Sq Ft

    16 Houston Ext Ave, Middletown, NY 10940

    Welcome to this beautiful, young Colonial, built in 2016 and ideally situated on a quiet street of newer homes in Middletown. Offering 4 spacious bedrooms and 2.5 bathrooms, this move-in-ready property seamlessly combines modern convenience with timeless style. The main level features gleaming hardwood floors, complemented by durable tile in the kitchen, half bath, and garage entry. Designed for

    Karleen Jedziniak Howard Hanna Rand Realty

    16 Houston Ext Ave, Middletown, NY 10940
  • /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
  • /37

    $699,999

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft

    11 Oak Ridge Rd, Middletown, NY 10940

    Welcome to 11 Oak Ridge Road — a stunning contemporary Colonial in the highly sought-after Presidential Heights community. Known for its scenic mountain views and prime Hudson Valley location, this upscale neighborhood offers the perfect balance of tranquility, convenience, and lifestyle. Meticulously maintained and thoughtfully updated, this exceptional home offers approximately 3,200 square

    Jacqueline Henry-Thompson Jackie Henry Realty LLC

    11 Oak Ridge Rd, Middletown, NY 10940
  • /43

    $729,000

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

    168 Pine Grove Rd, Middletown, NY 10940

    Move right into this nearly new home upgraded with premium finishings in Pine Grove Estates, where peaceful country living meets modern convenience in the desirable Minisink Valley School District. Set along a quiet road surrounded by sweeping views of green rolling hills, this home offers a rare sense of space, privacy, and peace. Enjoy miles of scenic vistas from the deck, the sprawling lawn,

    Leeshai Lemish Panorama Realty

    168 Pine Grove Rd, Middletown, NY 10940
  • /44

    $839,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    TBD Brook Rd, Middletown, NY 10941

    Brand New Luxury Home in the Valley Central School District! Stunning 3,000 sq. ft. modern Colonial privately set atop a scenic 5-acre wooded lot offering exceptional privacy and natural beauty. Conveniently located just 10 minutes to Middletown, Pine Bush, and Montgomery. The main level features a spacious open-concept floor plan with 9-foot ceilings, hardwood floors, formal living and family

    Philip Barnao eXp Realty

    TBD Brook Rd, Middletown, NY 10941
  • /34

    $299,000

    • 3 Beds
    • 1 Bath
    • 1,196 Sq Ft

    24 Crescent Place, Middletown, NY 10940

    Welcome to 24 Crescent Place, Middletown, NY. Affordable, move-in-ready homes with a detached garage, private driveway, and recent updates are becoming increasingly difficult to find, making this an exceptional opportunity for both homeowners and investors. This charming Colonial features 3 bedrooms, 1 full bathroom, comfortable living spaces, ample storage, and a functional layout designed for

    Yisroel Weiss Team W Realty LLC

    24 Crescent Place, Middletown, NY 10940
  • /49

    $529,900

    Open House 6/25
    • 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 Keller Williams Hudson Valley

    37-39 Wisner Ave, Middletown, NY 10940
  • /47

    $829,000

    • 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
  • /6

    $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
  • /45

    $680,000

    • 4 Beds
    • 2.5 Baths
    • 2,410 Sq Ft

    217 Schoolhouse Rd, Middletown, NY 10940

    Discover your dream home in this immaculate 2022 Colonial on a spacious 2-acre lot in the coveted Minisink School District. This practically new residence delivers sophisticated style, designer finishes, and the perfect balance of scenic countryside living with modern convenience. Enter a sunlit open floor plan with rich hardwood flooring flowing through expansive living spaces. An elegant stone

    Nerette Lewis RE/MAX Town & Country

    217 Schoolhouse Rd, Middletown, NY 10940
  • /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
  • /35

    $425,000

    • 4 Beds
    • 2 Baths
    • 1,780 Sq Ft

    203 Wisner Ave, Middletown, NY 10940

    From the moment you step onto the charming screened front porch, you'll understand why this home has been treasured. It's the kind of place where mornings begin slowly with coffee and conversation, where summer evenings linger a little longer, and where life's everyday moments become lasting memories. This beautifully maintained Colonial showcases the craftsmanship of another era, with gleaming

    Patricia Sassi RE/MAX Benchmark Realty Group

    203 Wisner Ave, Middletown, NY 10940
  • /18

    $450,000

    • 3 Beds
    • 1 Bath
    • 1,478 Sq Ft

    47 Wickham Ave Unit 45, Middletown, NY 10940

    Rare Opportunity to Live and Work under the same roof. Save money and time in buying this beautiful Colonial Home in a very sought after area of Middletown. Great for a professional I.E Accountant, Attorney, Real Estate Professional ETC This wonderful home features a spacious Private office with a separate entranceto meet with your clients or guests. The open floor plan features a Living Rm,

    John Biasi Howard Hanna Rand Realty

    47 Wickham Ave Unit 45, Middletown, NY 10940
  • /35

    $498,000

    • 3 Beds
    • 3 Baths
    • 2,088 Sq Ft

    13 S Shore Dr, Middletown, NY 10940

    Escape to your own private lakeside retreat at 13 S Shore Drive in Middletown. This beautiful high-end modern renovation large home. home offers direct lake access and breathtaking waterfront views, creating the perfect setting for relaxation and recreation. Whether you're enjoying morning coffee overlooking the water, kayaking from your backyard, or entertaining family and friends, this property

    Eidel Moses Rodeo Realty Inc

    13 S Shore Dr, Middletown, NY 10940
  • /50

    $809,900

    $29K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 3,900 Sq Ft

    225 van Duzer Rd, Middletown, NY 10940

    Discover A stunning Brand New Colonial Home over 3900 SQFT. This gorgeous home is now offering a beautiful outdoor kitchen with a bar setup, spacious backyard with retaining walls and a paved driveway. Featuring a grand front entrance boasts with a two-story foyer with iron stair balusters and a gorgeous combination of iron and wood. The main floor with its gleaming hardwood floors offers a

    Anita S. Cristiano HomeSmart Homes & Estates

    225 van Duzer Rd, Middletown, NY 10940

Home Prices in Middletown, NY

Home Price Trends

Median Sale Price
$400,000
Median Single Family Sale Price
$425,000
Median Townhouse Sale Price
$441,250
Median 2 Bedroom Sale Price
$289,000
Median 1 Bedroom Sale Price
$167,000
Average Price Per Sq Ft
$249
Number of Homes for Sale
123
Last 12 months Home Sales
481
Months of Supply
3.10
Median List Price
$405,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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