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Middletown, NY Homes for Sale with Basement

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  • /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
  • /47

    $489,998

    • 3 Beds
    • 2.5 Baths
    • 1,781 Sq Ft

    131 Meadow View Dr, Middletown, NY 10940

    Welcome to this beautifully maintained 3-bedroom, 2.5-bath end-unit three-level townhouse in the highly desirable Maple Fields community! Step inside to find gleaming hardwood floors throughout the main level, creating a warm and inviting space perfect for everyday living and entertaining. The lower level and second floor feature easy-to-care-for luxury vinyl plank flooring, offering both

    Karleen Jedziniak Howard Hanna Rand Realty

    131 Meadow View Dr, Middletown, NY 10940
  • /17

    $259,999

    • 4 Beds
    • 1 Bath
    • 1,140 Sq Ft

    29 Parsons Ln, Middletown, NY 10940

    Fantastic opportunity at 29 Parsons! This property is being offered as a cornerstone of a 3-parcel investment package. While individually the 4 bedroom home on 6+ acres of land the complete 3-property bundle—including an additional 5+ acres of land—is available for a package. The home is a 4 bedroom & lives as a 2 large bedrooms and a laundry room. Perfect for developers or those looking for a

    Camelia Pena-Rivera RE/MAX Distinguished Hms.&Prop

    29 Parsons Ln, Middletown, NY 10940
  • /44

    $575,000

    • 3 Beds
    • 2.5 Baths
    • 2,809 Sq Ft

    7 Starhaven Ave, Middletown, NY 10940

    This well-maintained home offers strong structural integrity, reliable mechanicals, and a flexible layout—ideal for buyers seeking a move-in-ready foundation with the opportunity to personalize cosmetic finishes over time. The main level features comfortable living and dining areas, an efficient kitchen layout, and generous natural light throughout. All bedrooms and the hallway include existing

    Michelle Gruberger Real Estate Circuit Inc

    7 Starhaven Ave, Middletown, NY 10940
  • /23

    $344,900

    • 4 Beds
    • 1.5 Baths
    • 1,598 Sq Ft

    16 Mountain Ave, Middletown, NY 10940

    Welcome to 16 Mountain Ave — a well-loved home with tons of potential in the heart of town! This spacious 4-bedroom, 1.5-bath Colonial offers the perfect blend of solid maintenance and room to make it your own. An estate property that’s been cared for throughout the years, it features original hardwood floors waiting to shine beneath the carpet, central air, and a layout that truly works for

    Valerie Jewis Keller Williams Realty

    16 Mountain Ave, Middletown, NY 10940
  • /23

    $429,000

    • 3 Beds
    • 2 Baths
    • 1,663 Sq Ft

    17 Last Rd, Middletown, NY 10941

    Welcome to 17 Last Rd, a unique retreat nestled on a sprawling 3.9-acre lot in the heart of Middletown. The upper level features 2 bedrooms and 1 full bathroom, while the lower level offers ground-level access with its own separate entrance, an additional bedroom, and a full bathroom. This versatile 2-bedroom, 2-full-bathroom home is designed to maximize natural light, creating a bright and airy

    Bryant Moran YourHomeSold Guaranteed Realty

    17 Last Rd, Middletown, NY 10941
  • /46

    $674,900

    • 4 Beds
    • 2.5 Baths
    • 2,360 Sq Ft

    320 Highland Avenue Extension, Middletown, NY 10940

    Rare Gem – Like-New Home with Park-Like Setting; StunningDesign. Welcome to a truly special property—an exceptional home thatcombines style, comfort, and an unbeatable location. Homes Like thisrarely come to market. Meticulously maintained and showing Like new,this residence offers the perfect blend of elegance and convenience with a tastefully designed interior with modern

    Matthew Gibbs Keller Williams Hudson Valley

    320 Highland Avenue Extension, Middletown, NY 10940
  • /24

    $439,900 Open Sun 12PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 1,905 Sq Ft

    566 County Route 49, Middletown, NY 10940

    For Sale – 566 County Route 46, Middletown, NY 10940 Welcome to this spacious 3-bedroom, 4-bath colonial-style condo located in a quiet country setting in Middletown. This home is the largest unit in the 4-unit condo complex, offering generous living space and a comfortable layout. The first floor features a bright and inviting large living room with sliding doors leading to a rear deck, perfect

    Jonathon Lee Keller Williams Hudson Valley

    566 County Route 49, Middletown, NY 10940
  • /29

    $650,000

    • 3 Beds
    • 4 Baths
    • 2,320 Sq Ft

    33 O Brian Rd, Middletown, NY 10940

    Seeking privacy and tranquility without complete seclusion? This charming log home sits on 15 acres surrounded by natural beauty (partially wetlands) and peaceful views of a neighboring lake. The expansive deck is ideal for entertaining and summer barbecues, while the three-season porch provides a cozy retreat in any weather. Inside, the great room impresses with vaulted ceilings, exposed beams,

    Kokoshen Li Corcoran Country Living

    33 O Brian Rd, Middletown, NY 10940
  • /19

    $479,999

    • 6 Beds
    • 2 Baths
    • 2,424 Sq Ft

    80 Prospect Ave, Middletown, NY 10940

    Welcome to 80 Prospect Ave, a well-maintained six-bedroom, two-bathroom home situated in the peaceful suburban setting of Middletown, NY. Built in 1918, this 2,424 square foot residence combines traditional architectural charm with modern updates, offering nearly 6,800 square feet of usable lot space ideal for both living and outdoor enjoyment. The property features a classic two-story design

    Jonathan Paredes Locqube New York, Inc.

    80 Prospect Ave, Middletown, NY 10940
  • /12

    $410,000

    • 5 Beds
    • 4 Baths

    41 Monhagen Ave Unit 39, Middletown, NY 10940

    Sold as is?This versatile property offers the perfect blend of comfortable living and passive income generation. Whether you are a first-time homebuyer looking to offset your mortgage or a seasoned investor seeking a high-yield asset, this legal two-family home is a standout choice. The Strategy: Live for Less, Earn MoreThe property is ideally configured for an owner-occupant strategy: Main

    Zhiheng Tang Keller Williams Hudson Valley

    41 Monhagen Ave Unit 39, Middletown, NY 10940
  • /26

    $335,000

    • 3 Beds
    • 1 Bath
    • 914 Sq Ft

    55 Hulse Ave, Middletown, NY 10940

    Cute as a Button! Town of Wallkill now offers this starter home that can turn into that turn-key investment property that you’ve been searching for. Look no further as you have found it! An enclosed porch leads you into a living room followed by an eat-in kitchen that has been fully remodeled and equipped with fresh out the box stainless steel appliances, granite counters and backsplash. New

    Sandra Arnez Keller Williams Hudson Valley

    55 Hulse Ave, Middletown, NY 10940
  • /26

    $599,990

    • 3 Beds
    • 3 Baths
    • 1,332 Sq Ft

    2078 Route 6, Middletown, NY 10940

    Unique bi-level house with spectacular 9-foot ceilings , from the moment you step inside , the grand entryway and soaring ceilings set the tone , complemented by abundant natural light and stunning views, just off entry the heart of the home awaits- beautiful granite countertop in kitchen with stainless appliances , hardwood floors flows seamlessly through the cozy living room anchored by a

    Steve Ruiz-Esparza eRealty Advisors, Inc

    2078 Route 6, Middletown, NY 10940
  • /50

    $499,999

    • 4 Beds
    • 2.5 Baths
    • 1,960 Sq Ft

    63 Blumel Rd, Middletown, NY 10941

    Charming turn-of-the-century farmhouse offering 4 bedrooms, 2.5 bathrooms, and 1,960 square feet of living space, set on just over half acre in the Pine Bush school district. This warm and inviting home features an abundance of original character, including beautiful wide-plank floors, built-in storage, and timeless architectural details, all complemented perfectly with thoughtful modern updates

    Gary MacEntee Keller Williams Realty

    63 Blumel Rd, Middletown, NY 10941
  • /38

    $493,000

    • 3 Beds
    • 2.5 Baths
    • 2,521 Sq Ft

    43 Woodside Knolls Dr, Middletown, NY 10940

    ?? FHA & VA Approved | Move-In Ready 3BR/2.5BA Townhouse | Woodside KnollsWelcome to this beautifully maintained 3-bedroom, 2.5-bath townhouse in the sought-after Woodside Knolls community — one of the rare condo developments in the area to hold both FHA and VA approval. That means eligible buyers can purchase with as little as 3.5% down (FHA) or $0 down (VA) — an exceptional and uncommon

    Ramanjit Dhanoa eXp Realty

    43 Woodside Knolls Dr, Middletown, NY 10940
  • /28

    $849,000

    • 5 Beds
    • 2.5 Baths
    • 3,764 Sq Ft

    238 S Centerville Rd, Middletown, NY 10940

    Spacious Country Retreat on 22.6 Acres in Minisink Valley School District This exceptional property offers privacy, comfort, and extensive amenities set on 22.6 picturesque acres. The master bedroom and bathroom were updated in 2016, complemented by a wet bar in the family room—perfect for entertaining. The home features three fireplaces and a wood stove, creating warmth and character throughout.

    Linda VanDeWeert BHG Real Estate Green Team

    238 S Centerville Rd, Middletown, NY 10940
  • /16

    $199,000

    • 1 Bed
    • 1 Bath
    • 748 Sq Ft

    488 Tally Ho Rd, Middletown, NY 10940

    A charming 1940 bungalow located in the highly desirable Minisink Valley School District, this home sits on a quiet 0.23-acre lot and makes an excellent starter home with low taxes. The front door opens into a spacious living area filled with natural light. The main level offers one bedroom plus an office that can serve as a second bedroom if needed. The full basement—not included in the listed

    Jason Schobert eXp Realty

    488 Tally Ho Rd, Middletown, NY 10940
  • /22

    $350,000

    • 3 Beds
    • 1 Bath
    • 892 Sq Ft

    91 Mountain Ave, Middletown, NY 10940

    Looking for one-story living in a private dead end street, look no further as you have found it! Beautiful hardwood floors welcome you into a living room with plenty of window light followed by an eat-in kitchen that has been fully equipped with gorgeous stainless steel appliances, new counters and plenty of cabinet space. Three spacious bedrooms with plenty of closet space and a beautiful tiled

    Sandra Arnez Keller Williams Hudson Valley

    91 Mountain Ave, Middletown, NY 10940
  • /35

    $999,999

    • 3 Beds
    • 2.5 Baths
    • 3,315 Sq Ft

    535 County Route 22, Middletown, NY 10940

    Looking to Enjoy Life? Experience 535 Ct Rt 22 in the Minisink School District. Unique Handcrafted Home that is surrounded by Nature and Privacy. This Amazing property is backed up to a NYS Protected Conservation in addition to the existing 21 1/2 Acres of Privacy. Gorgeous Breath-taking views can be seen from almost every window of the home. Enjoy the Dramatic, Sundrenched, Eye Popping Open

    John Biasi Howard Hanna Rand Realty

    535 County Route 22, Middletown, NY 10940
  • /15

    $264,999

    • 2 Beds
    • 2.5 Baths
    • 1,348 Sq Ft

    11 Jordan Ln, Middletown, NY 10940

    Great opportunity for investors for fix and flip.Minimal work needed to make it presentable.Town house located in a beautiful neighborhood.

    Siju John Kerala Realty, LLC

    11 Jordan Ln, Middletown, NY 10940
  • /26

    $225,000

    • 1 Bed
    • 1 Bath
    • 360 Sq Ft

    51 S Shore Dr, Middletown, NY 10940

    Welcome to 51 S Shore Drive, a charming and thoughtfully updated bungalow retreat nestled on a private, wooded 9,374 sq ft lot with sparkling lake views in scenic Middletown, NY. This beautifully curated 1-bedroom, 1-bath lakefront getaway offers 360 square feet of smart, stylish living space perfect for a weekend escape, vacation rental, or year-round peaceful living. Step inside to a crisp,

    Arya Rabinovits eRealty Advisors, Inc

    51 S Shore Dr, 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
  • /36

    $615,000

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

    9 Crane Rd, Middletown, NY 10941

    Back on the market, come see what over 3,000 square feet has to offer! Welcome to 9 Crane Road, in Middletown, New York where comfort meets charm, and every day feels like home, all you have to do is move in.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

    Shanese Williams Real Broker NY LLC

    9 Crane Rd, Middletown, NY 10941
  • /49

    $749,000

    • 5 Beds
    • 3 Baths
    • 2,828 Sq Ft

    482 Scotchtown Ave, Middletown, NY 10941

    Classic 1863 Farmhouse in Mint Condition – Riverfront Property in Goshen School District. Step into timeless elegance with this beautifully restored 1863 farmhouse, set on 10 picturesque acres in the highly desirable Goshen School District. This 5-bedroom, 3-bath home offers the perfect blend of historic charm and modern convenience, featuring original hardwood floors, a brick fireplace,

    Pamela Henning Keller Williams Hudson Valley

    482 Scotchtown Ave, Middletown, NY 10941
  • /2

    $480,000

    1 Royce Ave, Middletown, NY 10940

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

    Joseph Baratta Joseph Baratta Company Realty

    1 Royce Ave, Middletown, NY 10940
  • /43

    $765,000

    • 4 Beds
    • 2 Baths
    • 1,395 Sq Ft

    903 Rd, Middletown, NY 12421

    Unlock the door to your newly furnished & thoughtfully renovated 4 bedroom, 2 full bath Catskill Mountain Ski Retreat! The property delivers both Upstate sanctuary & investment making it a remarkably special experience. Overlooking breathtaking Denver Vega Valley, this 5 acre property captures sweeping mountain vistas, glowing sunsets, and a peaceful seasonal stream. Private wooded acreage

    Ashley O'Malley Listing by Jewett and Jewett LLC

    903 Rd, Middletown, NY 12421
  • /18

    $695,000

    • 8 Beds
    • 3 Baths
    • 3,000 Sq Ft

    21-23 Highland Ave, Middletown, NY 10940

    Kathleen Christopherson EXCLUSIVE SALES AND RENTALS

    21-23 Highland Ave, Middletown, NY 10940
  • /34

    $640,000 Pre-Foreclosure

    • 4 Beds
    • 2.5 Baths
    • 2,424 Sq Ft

    235 Maples Rd, Middletown, NY 10940

    This well-maintained spacious Colonial Home is ideally situated on a 2 Acre Lot in the Town of Wallkill Countryside. Lovely Kitchen W/Breakfast nook overlooks a Large Level Backyard & Private Rear Entertainment Deck. An entry foyer greets you when you arrive at this home, that features a Formal Dining Room, Living Room, Family Room, Powder Room, & mud Room/Laundry to complete the 1st Floor. The

    Shernette Hall VYLLA Home

    235 Maples Rd, Middletown, NY 10940
  • /2

    $525,000 Coming Soon

    • 5 Beds
    • 2 Baths
    • 1,965 Sq Ft

    171 Wawayanda Ave, Middletown, NY 10940

    Spacious and versatile split-level home offering 5 bedrooms and 2 full bathrooms with a home office, perfect for extended living or flexible space needs. This well-maintained property features a bright and inviting layout with two large family rooms, generously sized bedrooms, and an updated kitchen with Silestone countertops, wooden cabinets, and energy-efficient stainless steel appliances.

    Tiasha Coakley Keller Williams Hudson Valley

    171 Wawayanda Ave, Middletown, NY 10940
  • /13

    $290,000

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

    3 Top Notch Rd, Middletown, NY 10940

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

    Andrea Rose Keller Williams Hudson Valley

    3 Top Notch Rd, Middletown, NY 10940
  • /2

    $288,000

    • 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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