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4-Bedroom Homes for Sale in Middletown, NY

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  • /50

    $849,000

    • 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
  • /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
  • /26

    $599,000

    • 4 Beds
    • 3 Baths
    • 2,392 Sq Ft

    5 Oak Ridge Rd, Middletown, NY 10940

    Built in 2020, this spacious 2,392 sq ft home offers 4 bedrooms, 3 full bathrooms, and a 2-car garage. The upper level boasts an open-concept layout with vaulted ceilings, a modern kitchen featuring granite countertops and stainless steel appliances, a bright living room, and three bedrooms, including the primary suite, and two full baths. The finished lower level adds even more living space with

    Sandra Laramore Redfin Real Estate

    5 Oak Ridge Rd, Middletown, NY 10940
  • /39

    $789,000

    • 4 Beds
    • 2.5 Baths
    • 3,129 Sq Ft

    273 Pine Grove Rd, Middletown, NY 10940

    COMPLETELY TURN KEY !!!!! -----------RETIRED CUSTOM BUILDERS (husband and wife) - poured their hearts into their family home.--------------GENTLY USED and IMPECCABLY maintained, ----------- It is a WHOLE LOTTA HOUSE and has MANY UPGRADES INCLUDING : ---------- BRAND NEW 30 year ROOF ------------ NEWLY REFINISHED OAK HARDWOOD floors throughout ------------------------- ALL NEW stainless steel

    Douglas McVicker Suburban Investment Realty

    273 Pine Grove Rd, Middletown, NY 10940
  • /15

    $649,999

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

    217 Schoolhouse Rd, Middletown, NY 10940

    Experience the perfect blend of modern luxury and peaceful country living with this like-new colonial, built in 2022 and set on a spacious 2-acre lot in the desirable Minisink School District. Step inside to discover a thoughtfully designed, open-concept main level, where gleaming hardwood floors guide you through a bright and airy layout. A cozy fireplace anchors the living area, creating an

    Nerette Lewis RE/MAX Town & Country

    217 Schoolhouse Rd, Middletown, NY 10940
  • /22

    $740,900

    • 4 Beds
    • 3.5 Baths
    • 2,987 Sq Ft

    326 Ingrassia Rd, Middletown, NY 10940

    Welcome to this nearly new four-bedroom, three-bath ranch-style home, nestled on a picturesque two-acre, tree-lined lot that offers both privacy and natural beauty. With stucco siding and a thoughtfully designed layout, this home combines modern comfort with timeless appeal.Step inside to find a spacious, open-concept floor plan with abundant natural light. The main living areas flow

    Catherine Eichner Eichner Realty Group Inc.

    326 Ingrassia Rd, Middletown, NY 10940
  • /34

    $619,000

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

    458 County Route 50, Middletown, NY 10940

    Welcome to 458 County Route 50!Discover the perfect blend of elegance and functionality in this stunning colonial residence nestled in the highly sought-after Goshen School District. This expansive 2,200 sq. ft. home boasts 4 spacious bedrooms, 2.5 bathrooms, and a finished basement, complete with a one-car garage.Upon entering, you'll be greeted by an open floor plan featuring rich oak

    Travis Thompson Keller Williams Hudson Valley

    458 County Route 50, Middletown, NY 10940
  • /44

    $630,000

    • 4 Beds
    • 3 Baths
    • 2,132 Sq Ft

    125 White Bridge Rd, Middletown, NY 10940

    Enjoy 2,132 square feet of comfortable living space on 2.6 beautiful acres in a serene country setting—just 10 minutes from shopping, restaurants, and more.Located at 125 White Bridge Road in the town of Mount Hope, NY, this raised ranch offers far more than just a place to live. It’s a retreat, a gathering space, and a canvas for everyday joy.Step inside through a spacious foyer and

    Anthony Spadaro RE/MAX Benchmark Realty Group

    125 White Bridge Rd, Middletown, NY 10940
  • /49

    $779,900

    • 4 Beds
    • 3 Baths
    • 3,900 Sq Ft

    225 van Duzer Rd, Middletown, NY 10940

    Welcome to a stunning brand new Colonial Home nestled in the heart of the town of Wallkill . The 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 spacious living room with built-in electric fireplace to a family room to a dining dining area open to a beautiful kitchen

    Anita S. Cristiano HomeSmart Homes & Estates

    225 van Duzer Rd, Middletown, NY 10940
  • /26

    $759,900

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

    195 Mulford Rd, Middletown, NY 10940

    Stunning New Construction colonial on a dead end street. Welcome to your dream home set on 3 picturesque acres in the Town of Greenville, within the highly sought-after Minisink Valley School District. The Oakwood model is nestled on a private, partially wooded lot at the end of a quiet cul-de-sac, offering the perfect blend of style, comfort, and functionality. Step inside to find 4 spacious

    Chris Ogden Realty Promotions Inc

    195 Mulford Rd, 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
  • /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

    $749,899

    • 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
  • /16

    $599,900 Open Sat 1PM - 3PM

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

    718 Mount Hope Rd, Middletown, NY 10940

    Let's welcome the Fall 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 formal

    Anita S. Cristiano HomeSmart Homes & Estates

    718 Mount Hope Rd, Middletown, NY 10940
  • /43

    $339,900

    • 4 Beds
    • 2 Baths
    • 1,696 Sq Ft

    28 Spring St, Middletown, NY 10940

    BACK ON MARKET: Your Dream Home Awaits at 28 Spring St, Middletown.Don't let this second chance slip away. This beautiful, 4 bedroom, 2 bathroom home is back on the market. Previous buyer's financing fell through. This is an incredible opportunity for you to step right in and secure a truly remarkable property. The seller has invested in significant updates to make this home move-in ready.

    Leidy Placido Howard Hanna Rand Realty

    28 Spring St, 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

    Patricia Sassi RE/MAX Benchmark Realty Group

    56 Mulberry St Unit 54, Middletown, NY 10940
  • /33

    $400,000

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

    29 Little Ave, Middletown, NY 10940

    Discover this renovated colonial home nestled in the charming city of Middletown. This spacious single-family residence offers a perfect blend of classic charm and tasteful updates. The main level features a dedicated home office, an inviting living room, and an open-concept kitchen with stunning granite countertops and a center island. A formal dining room and a convenient half bath complete

    Michael LaMorte Christie's Int. Real Estate

    29 Little Ave, Middletown, NY 10940
  • /24

    $378,000

    • 4 Beds
    • 3 Baths
    • 1,505 Sq Ft

    8 Ebury Mews, Middletown, NY 10940

    Beautiful 4-Bedroom Home in Canterbury Knolls – Town of Wallkill Welcome to this spacious and beautifully maintained 4-bedroom, 3-bath detached home in the highly sought-after Canterbury Knolls community.This rare property is one of the largest models in the neighborhood, offering the perfect blend of comfort, privacy, and convenience. Tucked away at the end of a quiet cul-de-sac and bordered

    Jonathon Lee Keller Williams Hudson Valley

    8 Ebury Mews, Middletown, NY 10940
  • /32

    $425,000

    • 4 Beds
    • 3 Baths
    • 1,728 Sq Ft

    42 Genung St, Middletown, NY 10940

    BEAUTIFUL turn-key home located in MIDDLETOWN! Do NOT let the ouside fool you as this home is bigger than expected... Step inside this Ranch that is in mint condition with the upgrades it offers. Open floor layout from Living room to kitchen. New vinyl floors and recessed lighting throughout. Modern eat-in kitchen with new white cabinets, granite countertops, backsplash & gorgeous fresh out the

    Sandra Arnez Keller Williams Hudson Valley

    42 Genung St, Middletown, NY 10940
  • /48

    $1,100,000

    • 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
  • /34

    $529,999

    • 4 Beds
    • 2.5 Baths
    • 2,132 Sq Ft

    22 Sharon Dr, Middletown, NY 10941

    Price Improved! Come home to this lovely 4 bedroom 2.5 bath home, situated on .37 acres. This home features an updated kitchen and bath with granite counter top and attractive cabinetry. Beautiful hardwood flooring and wall to wall carpeting can be found throughout. The large deck overlooks a luscious fruit filled peach tree and a backyard that makes the perfect spot for entertaining. This

    Tonya Finn Keller Williams Hudson Valley

    22 Sharon Dr, Middletown, NY 10941
  • /30

    $549,000

    • 4 Beds
    • 3.5 Baths
    • 2,307 Sq Ft

    73 Watkins Ave, Middletown, NY 10940

    Exquisite Updated Colonial Residence in a Prestigious Middletown LocationDiscover timeless elegance combined with modern sophistication in this beautifully updated 4-bedroom, 3-bath Colonial home. Perfectly situated on a quiet, tree-lined street, this residence offers a seamless blend of classic architectural details and contemporary upgrades, creating a truly refined living

    Jonathon Lee Keller Williams Hudson Valley

    73 Watkins Ave, Middletown, NY 10940
  • /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
  • /44

    $385,000

    • 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
  • /38

    $549,999

    • 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
  • /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, which 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

    Mark Tierney Howard Hanna Rand Realty

    25 Mill St, Middletown, NY 10940
  • /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
  • /18

    $565,000

    • 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
  • /43

    $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
  • /46

    $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

    $440,000

    • 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 ideal

    Soleil Jackman Howard Hanna Rand Realty

    4 Thistle Ln, Middletown, NY 10940
  • /17

    $360,000

    • 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
$383,500
Median 2 Bedroom Sale Price
$275,000
Median 1 Bedroom Sale Price
$175,000
Average Price Per Sq Ft
$246
Number of Homes for Sale
111
Last 12 months Home Sales
487
Months of Supply
2.70
Median List Price
$399,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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