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4-Bedroom Homes for Sale in Middletown, NY

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  • /41

    $575,000

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

    1583 Mountain Rd, Middletown, NY 10940

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

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (329) 208-3559

    1583 Mountain Rd, Middletown, NY 10940
  • /50

    $879,000

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

    3 Kings Dr, Middletown, NY 10941

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

    Agent Photo

    Christina Rowan

    Howard Hanna Rand Realty

    (845) 393-3879

    3 Kings Dr, Middletown, NY 10941
  • /26

    $410,000

    • 4 Beds
    • 2 Baths
    • 1,668 Sq Ft

    31 Beattie Ave, Middletown, NY 10940

    Great 2 family home in the city of Middletown. Each apartment features 2 bedrooms, 1 bathroom. This property is located in a zoning that requires one of the apartments is occupied by the owner. House is well maintained and cared for. Large lot offers plenty of yard and parking. Walk-up attic offers plenty of storage. Each tenant has their own washer and dryer hook-up. Detached 2 car garage ideal

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (845) 286-4605

    31 Beattie Ave, Middletown, NY 10940
  • /21

    $599,000

    • 4 Beds
    • 3 Baths
    • 2,552 Sq Ft

    125 Whipple Rd, Middletown, NY 10940

    Discover the perfect blend of serenity and comfort in this stunning 4-bedroom, 3-bathroom raised ranch nestled on a sprawling 1.5-acre lot in the heart of Middletown, NY. As you step inside, the heart of the residence, a spacious and sunlit living area, invites family gatherings and effortless entertaining. Culinary enthusiasts will delight in the modern kitchen, boasting sleek appliances and

    Eboni Navas Julia B Fee Sothebys Int. Rlty

    125 Whipple Rd, Middletown, NY 10940
  • /36

    $625,000

    • 4 Beds
    • 3.5 Baths
    • 2,760 Sq Ft

    214 Phillips St, Middletown, NY 10940

    Welcome to this beautiful newly built 4-bedroom, 3.5-bath home featuring a spacious 2,760 sqft layout across three levels of living space. The gourmet kitchen features an island with a breakfast bar and flows seamlessly into a large dining area. The luxurious primary suite includes a full ensuite bath with dual vanities, a shower, and a separate soaking tub, all highlighted by expansive windows.

    Donna Gray Redfin Real Estate

    214 Phillips St, Middletown, NY 10940
  • /33

    $615,000

    • 4 Beds
    • 3 Baths
    • 3,350 Sq Ft

    9 Crane Rd, Middletown, NY 10941

    Welcome to 9 Crane Road, in Middletown, New York where comfort meets charm, and every day feels like home.Step into this beautifully well maintained residence, nestled on a quiet, tree-lined block. This move-in-ready home is designed for those who crave warmth, flexibility, and room to grow.From the moment you enter, natural light pours through every corner, highlighting elegant crown

    Shanese Williams Real Broker NY LLC

    9 Crane Rd, Middletown, NY 10941
  • /29

    $569,000

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

    88 James Clark Dr, Middletown, NY 10940

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

    Debbie Goldstein Howard Hanna Rand Realty

    88 James Clark Dr, Middletown, NY 10940
  • /45

    $550,000

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

    116 Lewis Landing Rd, Middletown, NY 10940

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

    Thomas Smith Cronin & Company Real Estate

    116 Lewis Landing Rd, Middletown, NY 10940
  • /48

    $599,000

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

    31 Highland View Place, Middletown, NY 10940

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

    Abbe Distelburger Keller Williams Realty

    31 Highland View Place, Middletown, NY 10940
  • /35

    $589,000

    • 4 Beds
    • 3 Baths
    • 2,732 Sq Ft

    24 3rd St, Middletown, NY 10940

    BETTER THAN NEW! SPACIOUS 4-Bedroom, 3-Full Bath Bi-Level ColonialWelcome to this meticulously maintained home offering over 2,700 sq ft of beautifully finished living space that blends modern style with timeless charm.Step into the gorgeous eat-in kitchen, thoughtfully designed with:A large center island with ample seatingGleaming hardwood floorsVaulted

    Jane Panico Realty Promotions Inc

    24 3rd St, Middletown, NY 10940
  • /38

    $575,000

    • 4 Beds
    • 2.5 Baths
    • 2,144 Sq Ft

    10 Frederick St, Middletown, NY 10941

    Move in ready 4 bedroom/2.1 Bath with so many updates. Elegant entrance with rod iron spindles, Modern chandelier, Picture Window, Slate stone landing. Gourmet Kitchen offers Custom designed Kraftmaid collection cabinets with Chef grade range hood, Porcelain backsplash, Pot Filler, Large Island/Waterfall with built in space for microwave, Quartz countertops, Samsung Stainless steel appliances,

    Angelo Acierno Keller Williams Realty

    10 Frederick St, Middletown, NY 10941
  • /16

    $649,900

    • 4 Beds
    • 3 Baths
    • 2,444 Sq Ft

    744 Mount Hope Rd, Middletown, NY 10940

    A beautiful colonial home sitting on 10.80 acres with open layout is being built in the town of Wallkill. Offering about 2400 SQFT living space including the finished basement with 4 bedrooms, 3 full bathroom and a one car garage. From the living room to a dining area and it's open to a beautiful kitchen with Quartz countertops, an island and stainless appliances. This gorgeous home will have 1

    Anita S. Cristiano HomeSmart Homes & Estates

    744 Mount Hope Rd, Middletown, NY 10940
  • /42

    $749,900

    • 4 Beds
    • 3.5 Baths
    • 2,823 Sq Ft

    264 Lybolt Rd, Middletown, NY 10941

    Located on a quite country road in the town of Wallkill sits this move in ready new construction colonial on 2.12 wooded private acres in the sought after Pine Bush School district. The Mable offers an open floor plan design on the first level with hardwood floors throughout the oversized living room with a gas fireplace, formal dining room and custom kitchen with breakfast bar, quartz

    Chris Ogden Realty Promotions Inc

    264 Lybolt Rd, Middletown, NY 10941
  • /50

    $875,000

    • 4 Beds
    • 4 Baths
    • 3,699 Sq Ft

    21 Lincoln Terrace Unit 19, Middletown, NY 10940

    Step into a rare and iconic mid-century modern residence, masterfully designed and once inhabited by renowned local architect Dennis Jurow. Tucked away on a private and mature one-acre lot in Middletown, this 4,000+ square foot home is a true celebration of 1970s contemporary design—thoughtfully preserved with original details throughout. This one-of-a-kind home features ten sliding glass doors

    Patricia Sassi RE/MAX Benchmark Realty Group

    21 Lincoln Terrace Unit 19, Middletown, NY 10940
  • /50

    $829,000

    • 4 Beds
    • 2.5 Baths
    • 2,828 Sq Ft

    482 Scotchtown Ave, Middletown, NY 10941

    Mint condition, classic, fully-restored 1863 farmhouse. This 4-bedroom, 2 1/2-bathroom home sits on 10 serene acres with stunning horse farm views and features including original hardwood floors, a brick fireplace, and formal dining with exquisite molding. Also noted is the updated plumbing. Enjoy a wraparound porch, a pond with fish, and river access for kayaking. Completely inspiring with a

    Pamela Henning Keller Williams Hudson Valley

    482 Scotchtown Ave, Middletown, NY 10941
  • /36

    $599,000

    • 4 Beds
    • 2.5 Baths
    • 1,825 Sq Ft

    708 Kirbytown Rd, Middletown, NY 10940

    Such a peaceful setting for this immaculate 4 BR, 2.5 bath Colonial in the heart of The Minisink School District. This home is a dream for pet owners! The fenced backyard keeps your pets safe and secure while they play, and the underground dog fence lets them roam worry-free. There is a woodstove that is perfect for chilly evenings that will help with your heating costs during the cold winter

    Debbie Walsh SHAHAR Management LLC

    708 Kirbytown Rd, Middletown, NY 10940
  • /18

    $600,000

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

    77 Upper Rd, Middletown, NY 10940

    Beautiful Ranch Style Home, with 4 spacious bedrooms, 3 upgraded Bathrooms, beautiful Hardwood floor recently painted, lots of Entertainment space, Full finish basement with lots of space that fits laundry, gym, and more entertainment space. Property has a huge tennis court, above ground pool, hot tub and extra yard space. A new septic tank was installed, brand new water system. Perfect Home for

    Yajaira Silva Madison Allied LLC

    77 Upper Rd, Middletown, NY 10940
  • /34

    $599,999

    • 4 Beds
    • 3.5 Baths
    • 2,188 Sq Ft

    26 Kyleigh Way, Middletown, NY 10940

    Welcome to this stunning, 5-year-young home located in the desirable Sunrise Hills development.This beautifully maintained residence offers 4 spacious bedrooms, 3 full bathrooms, and 1 half bathroom. The grand cathedral entryway features an elegant chandelier that can be admired from both inside and out, highlighting the top landing of the staircase.The large fourth bedroom is

    Delroy Smith List 4 Less Realty

    26 Kyleigh Way, Middletown, NY 10940
  • /11

    $849,900

    • 4 Beds
    • 3.5 Baths
    • 3,407 Sq Ft

    29 Hubbard Rd, Middletown, NY 10940

    New construction colonial on a beautiful 9+ acre lot with views of the Shawangunk Mountain Ridge, a spring fed pond and open fields and woods located on a private dead end road in the Pine Bush S/D. and close to major highways. The Sienna model features include 4 bedrooms, 3.5 baths, gorgeous red oak hardwood floors and spacious rooms. Relax in the cozy living room by the warm inviting fireplace

    Chris Ogden Realty Promotions Inc

    29 Hubbard Rd, Middletown, NY 10940
  • /16

    $599,900

    • 4 Beds
    • 3 Baths
    • 2,445 Sq Ft

    718 Mount Hope Rd, Middletown, NY 10940

    Let's welcome the Summer of 2025 with this beautiful and spacious contemporary home. It is nestled up on the hill with great views in the town of Wallkill. This gorgeous home is going to be ready in less than 6 to 8 weeks. The upper level is featuring an open layout with gleaming oak hardwood floors throughout a massive living room with a very high ceiling & built in electric fireplace to a

    Anita S. Cristiano HomeSmart Homes & Estates

    718 Mount Hope Rd, Middletown, NY 10940
  • /23

    $629,900

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

    11 Vista View Terrace, Middletown, NY 10941

    Welcome to Vista View Terrace - This stunning colonial home is being built and nestled on the cul-de-sac of a beautiful neighborhood in Scotchtown area in the town of Wallkill. Offering about 2400 SQFT living space including the finished basement with 4 bedrooms, 3 full bathroom and a one car garage. From the living room to a dining area and it's open to a beautiful kitchen with granite

    Anita S. Cristiano HomeSmart Homes & Estates

    11 Vista View Terrace, Middletown, NY 10941
  • /45

    $599,900

    • 4 Beds
    • 3 Baths
    • 2,434 Sq Ft

    94 Fair Oaks Rd, Middletown, NY 10940

    *AVAILABLE* NEW CONSTRUCTION BILONIAL BEAUTY ON 10+ ACRES! Welcome to your dream home – a stunning, newly built bilonial-style residence that redefines upscale living with modern aesthetic and thoughtful design in every inch. 4 Spacious Bedrooms | 3 Full Designer Bathrooms. Featuring cathedral ceilings in the living room, this open-concept home is flooded with natural light from the

    Valeria Rios HomeSmart Homes & Estates

    94 Fair Oaks Rd, Middletown, NY 10940
  • /6

    $94,000

    • 4 Beds
    • 2 Baths
    • 1,248 Sq Ft

    3 Birch St, Middletown, NY 10940

    Single Family Seasonal Cottage in Middletown!Here's the opportunity to create your perfect getaway at this cozy 2 story cabin set on a 50 x 100 ft lot in the heart of Middletown. Currently, the attic portion is being converted to living space. This cabin holds endless potential and offers buyers a chance to design a custom retreat or full-time residence. Property features:- 4

    Thomas Horodecki Capri Jet Realty Corp

    3 Birch St, Middletown, NY 10940
  • /21

    $479,900

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

    93 Rolling Meadows Rd, Middletown, NY 10940

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

    Suzanne Bongiorno Century 21 E & M Williams Rlty

    93 Rolling Meadows Rd, Middletown, NY 10940
  • /40

    $415,000

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

    167 Rockwell Ave, Middletown, NY 10940

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

    Ermelinda Mclaughlin eXp Realty

    167 Rockwell Ave, Middletown, NY 10940
  • /44

    $449,000

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

    100 Academy Ave, Middletown, NY 10940

    WELCOME HOME!!! A lovely and spacious single family property, with an extra large backyard, located in the center of Middletown is looking for its new owners, ready to move in!!!The house features a total of 4 bedrooms, 2 full baths, plus a office room, with a semi finished basement for laundry and storage. New SS washer dryer included! The 1st floor consists of a nice kitchen with

    Mordy Abelesz eXp Realty

    100 Academy Ave, Middletown, NY 10940
  • /20

    $334,900

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

    12 Columbine Ct, Middletown, NY 10940

    Don’t miss this beautifully updated end-unit 4-bedroom, 1.5-bath townhouse in the heart of Middletown, NY! This spacious home features a long list of recent upgrades including brand-new siding, boiler, driveway, concrete patio, flooring, carpeting upstairs in the bedrooms, Kitchen cabinets, counter tops and appliances. As an end unit, it offers extra privacy and natural light, along with a fully

    Christina Gilligan HomeSmart Homes & Estates

    12 Columbine Ct, Middletown, NY 10940
  • /37

    $369,000

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

    51 Howard Dr, Middletown, NY 10941

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

    Adrienne Volpe Keller Williams Hudson Valley

    51 Howard Dr, Middletown, NY 10941
  • /19

    $369,000

    • 4 Beds
    • 1.5 Baths
    • 1,272 Sq Ft

    35 Woods Place, Middletown, NY 10940

    This charming four-bedroom, one-bathroom home offers comfortable living space with a versatile layout. The layout provides plenty of room with flexible living spaces. Located in a welcoming Middletown neighborhood, you'll enjoy easy access to quality schools, convenient public transportation, and shopping options just minutes away. Whether you're starting fresh or looking to upgrade, this

    Kevin Sanabria eRealty Advisors, Inc

    35 Woods Place, Middletown, NY 10940
  • /29

    $359,000

    • 4 Beds
    • 2 Baths
    • 2,460 Sq Ft

    9 Albert St, Middletown, NY 10940

    WELCOME, HOME OWNERS AND INVESTORS, 3 FINISHED FLOORS! Welcome to this exceptional income generating multi-residential property! Ideally situated near Middletown’s restaurants, shopping malls, public transportation to NYC, major highways, and hospital facilities. This property offers unmatched convenience. Each apartment boasts two spacious bedrooms, an over-sized living room perfect for your

    Robert 'Bob' & Frances 'Fran' Murray Howard Hanna Rand Realty

    9 Albert St, Middletown, NY 10940
  • /5

    $280,000

    • 4 Beds
    • 3 Baths
    • 1,374 Sq Ft

    22 Bonnell St, Middletown, NY 10940

    Welcome to 22 Bonnell St, a charming 4-bedroom, 3-bathroom home situated on a desirable corner lot on a quiet street in the heart of Middletown, NY. This spacious residence is brimming with potential, offering a unique opportunity to customize and create your dream home exactly the way you envision it. While the home could benefit from some updating, its solid foundation and prime location make

    Emmett McDowell Keller Williams Rlty Integrity

    22 Bonnell St, Middletown, NY 10940
  • /50

    $599,900

    • 4 Beds
    • 3 Baths
    • 2,800 Sq Ft

    2213 Mount Hope Rd, Middletown, NY 10940

    Fantastic investment opportunity in this growing Mount Hope area. Imagine operating your business on the ground level and collecting rent from 3 residential apartments on the second floor. All the apartments have been updated and delivered vacant. Your chance to collect market rents. There is the option to convert the ground level space to another residential apartment, or utilize it as it

    Chris Scibelli Keller Williams Realty

    2213 Mount Hope Rd, Middletown, NY 10940
  • /9

    $395,000

    • 4 Beds
    • 2 Baths

    25 Mill St, Middletown, NY 10940

    Beautifully recently renovated 2 story, with 2 br apartment on second for at $2000./month, has 2 yr lease, vacant first floor unit with matching new renovation, includes washer and dryer. New kitchen with granite counters, new full tile bath. High efficiency furnaces. First floor is a commercial space, ready to occupy. Tenant pay utilities. Seller says present all offers. Come and see!!!!

    Mark Tierney Howard Hanna Rand Realty

    25 Mill St, Middletown, NY 10940
  • /37

    $499,999

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

    612 Shoddy Hollow Rd, Middletown, NY 10940

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

    Kewin Garabito eXp Realty

    612 Shoddy Hollow Rd, Middletown, NY 10940
  • /43

    $1,600,000

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

    565 Prosperous Valley Rd, Middletown, NY 10940

    Your dream countryside retreat located in Orange County NY. This custom-built 4,000 sq. ft. Contemporary Ranch is situated on an expansive 61-acre property. (two separate parcels) It includes a two-story 35'x60' barn with 7 horse stalls, a lean-to, a silo, and a tack room. Above the barn, you'll find a 20'x64' loft area with a separate well and 100-amp electric service. The 25'x50' concrete

    Michelle Gruberger Real Estate Circuit Inc

    565 Prosperous Valley Rd, Middletown, NY 10940
  • /41

    $480,000

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

    4 Thistle Ln, Middletown, NY 10940

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

    Soleil Jackman Howard Hanna Rand Realty

    4 Thistle Ln, Middletown, NY 10940
  • /26

    $399,000

    • 4 Beds
    • 2.5 Baths
    • 1,620 Sq Ft

    47 Prince St, Middletown, NY 10940

    Welcome to this lovely, renovated. Formerly a 3 bedroom/2-bathroom house, this home has been renovated in 2023 into a 4 bed/2.5 bath adding a 1st Floor Master Bedroom Suite, increasing the square footage of living space. This house has plenty of character and is better than new construction. Open Concept Layout, Enclosed Porch, Luxury Vinyl Flooring, Stainless Steel Appliances, Butcher Block

    D'Wana Haynesworth YourHomeSold Guaranteed Realty

    47 Prince St, Middletown, NY 10940
  • /35

    $699,000

    • 4 Beds
    • 3.5 Baths
    • 3,432 Sq Ft

    200 Mt Orange Rd, Middletown, NY 10940

    Welcome to this most charming 1870's farmhouse situated on idyllic 6.4 level pastoral acres with small pond. This property boasts wide moldings and other intricate detailing that showcase the exceptional craftmanship that went into its construction. Enjoy both gorgeous sunrises and sunsets from almost any room. This home has been well maintained, with some newer additions, such as the family

    Joe Distelburger Keller Williams Realty

    200 Mt Orange Rd, Middletown, NY 10940
  • /17

    $375,000

    • 4 Beds
    • 2 Baths
    • 1,796 Sq Ft

    24 Edinburgh Rd, Middletown, NY 10941

    Looking for something different? This spacious 4 bedroom 2 full bath contemporary raised ranch in the Town Of Wallkill just may be what you are looking for ! Open living room with cathedral ceilings & hardwood flooring. First floor primary bedroom & primary bath. Upper level has hardwood flooring through out with 3 bedrooms & a full bath. Family room on lower level. Rear deck overlooking your

    Ernie Acampora River Realty Services, Inc.

    24 Edinburgh Rd, Middletown, NY 10941

Home Trends in Middletown, NY

Housing Trends

Median Sale Price
$395,000
Median Single Family Sale Price
$415,000
Median Townhouse Sale Price
$400,000
Median 2 Bedroom Sale Price
$275,000
Median 1 Bedroom Sale Price
$169,000
Average Price Per Sq Ft
$243
Number of Homes for Sale
110
Last 12 months Home Sales
503
Months of Supply
2.60
Median List Price
$399,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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