Middletown, NY Homes for Sale under $600,000

• 

  

  

  /22

  $399,000

  $26K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,337 Sq Ft

  19 Putters Way Unit 9, Middletown, NY 10940

  Welcome to a move-ready condo in the desirable Walkill community. This splendid duplex has been upgraded with modern paint tones and the latest finishes. Bright and sunny rooms with updated lighting throughout. The kitchen boasts sleek, brand-new appliances and classic wood cabinetry. The bathrooms have been meticulously maintained. Cathedral ceilings in both bedrooms lend a dramatic vibe for a

  Abraham Lefkowitz Access Realty Team Inc

  19 Putters Way Unit 9, Middletown, NY 10940
• 

  

  

  /23

  $399,999

  • 5 Beds
  • 2 Baths
  • 1,664 Sq Ft

  341 Highland Ave Extension, Middletown, NY 10940

  Welcome to 341 Highland Ave Ext, a bright and airy 4-bedroom, 2-bath split-level home conveniently situated in the heart of town. An inviting open floor plan creates effortless flow throughout the main living spaces, offering comfort, style, and plenty of natural light. Enjoy a level, fenced-in backyard—ideal for outdoor gatherings or peaceful relaxation. With local eateries, shopping, and daily

  Valerie Jewis Keller Williams Realty

  341 Highland Ave Extension, Middletown, NY 10940
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /22

  $318,000

  • 3 Beds
  • 2.5 Baths
  • 1,345 Sq Ft

  9 Jordan Ln, Middletown, NY 10940

  Welcome to easy townhouse living in Mountainside Hills, Middletown! This lovely 3 bedroom, 2.5 bath home offers comfort, space, and convenience. The main level features a spacious living room, formal dining area with hardwood floors, powder room and laundry room. The spacious eat-in kitchen is equipped with stainless steel appliances, along with elegant granite countertops. Upstairs, you'll find

  Bonnie Natt Realty Promotions Inc

  9 Jordan Ln, Middletown, NY 10940
• 

  

  /58

  $575,000

  • 12 Beds
  • 10 Baths
  • 5,004 Sq Ft

  5 Wawayanda Place, Middletown, NY 10940

  CASH ONLY - Totally renovated large home with 12 bedrooms, 8 of them being suites with their own full bathroom. 10 full bathrooms total. Home also features game room, large dining area, living room, spacious eat in kitchen with stainless appliances & island, laundry off the kitchen, large fenced patio & inground pool. Conveniently located around Orange County Community College, tennis & skate and

  Jamie Sittner Find Advisors

  5 Wawayanda Place, Middletown, NY 10940
• 

  

  /29

  $550,000

  • 4 Beds
  • 3 Baths
  • 2,018 Sq Ft

  13 Avenue B, Middletown, NY 10940

  THIS BI LEVEL FEATURES 2018 SQUARE FEET, WITH AN OPEN CONCEPT, VAULTED CEILINGS, MASTER SUITE, THREE ADDITIONAL BEDROOMS WITH TWO MORE FULL BATHS, HARD WOOD FLOORING ON THE SECOND LEVEL, KITCHEN WITH ISLAND, GRANITE COUNTER TOP, STAINLESS STEEL APPLIANCES, TWO CAR ATTACHED GARAGE WITH AN EXTENDED DRIVEWAY TO ACCOMODATE MANY MORE CARS

  Christopher Hosten Charles Rutenberg Realty, Inc.

  13 Avenue B, Middletown, NY 10940
• 

  

  /23

  $309,000

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft

  181 Deer Ct Dr, Middletown, NY 10940

  Discover easy living in this spacious Deer Run condo, offering room and the added convenience of a dedicated parking space. Nestled in one of Middletown's most desirable communities, this home combines comfort, practicality, and an unbeatable location. Enjoy being just minutes from major highways, shopping centers, restaurants, public transportation, and everyday essentials, making commuting and

  Beverly Huaman Howard Hanna Rand Realty

  181 Deer Ct Dr, Middletown, NY 10940
• 

  

  /44

  $355,000

  • 3 Beds
  • 1 Bath
  • 1,830 Sq Ft

  122 Castle High Rd, Middletown, NY 10940

  Step into the timeless charm of this character-filled home, originally built in the 1920s and offering a unique multi-level layout with inviting living spaces throughout. Upon entering, you'll find the kitchen conveniently located on the lower level, featuring a new butcher block countertop and newer appliances. Just beyond the kitchen is a versatile finished bonus room—perfect as a dining room,

  Denise Clancy Curasi Realty, Inc.

  122 Castle High Rd, Middletown, NY 10940
• 

  

  /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
• 

  

  /32

  $449,000

  $19K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  13 Forest Ave, Middletown, NY 10940

  Fresh updates. New improvements. New opportunity. 13 Forest Avenue is officially back on the market after completing repairs and updates, and it's ready for its next owner. This spacious home offers comfortable living, updated features, and a convenient location near schools, shopping, restaurants, and commuter routes. The recent improvements provide added value and confidence for buyers looking

  Pete Wolven Hudson Valley Home Connection

  13 Forest Ave, Middletown, NY 10940
• 

  

  /3

  $350,000

  • Land
  • 1.42 Acres
  • $245,752 per Acre

  65 James P Kelly Way, Middletown, NY 10940

  Great location for a business. C-3 Zoning allows for any business, commercial or residential mix use. 262 feet frontage. Annual Average Daily Traffic (AADT) for 2023 is 10,569. There was a pre-approved building plan for a doctor's office building. The land is in the city of Middletown. The city will provide water and sewer. C-3 allow for 6 story mix-use business and residential building with the

  Jonathon Lee KW Hudson Valley United

  65 James P Kelly Way, Middletown, NY 10940
• 

  

  /46

  $515,000

  Open Fri 4PM - 6PM

  • 4 Beds
  • 1.5 Baths
  • 1,732 Sq Ft

  23 Marcy Ln, Middletown, NY 10941

  Welcome to this beautifully renovated raised ranch in the desirable Scotchtown neighborhood. Offering over 1,700 square feet of living space, this move-in-ready home features 4 spacious bedrooms and 2 updated bathrooms. The bright main level offers a spacious L-shaped living and dining room filled with natural light, along with a beautifully renovated kitchen featuring brand-new stainless steel

  Dennis Aboagye Keller Williams Realty Group

  23 Marcy Ln, Middletown, NY 10941
• 

  

  /19

  $575,000

  • 3 Beds
  • 3 Baths
  • 5,157 Sq Ft

  20 John St, Middletown, NY 10940

  For Sale: Income-Producing Mixed-Use Building in Prime Downtown Middletown Take advantage of this exceptional opportunity to own a versatile, income-generating property in the heart of Downtown Middletown—an up-and-coming city with a pro-business government and strong growth potential. Property Overview: First Floor:Spacious 2,000 sq. ft. commercial space, currently used as a retail store,

  Jonathon Lee KW Hudson Valley United

  20 John St, Middletown, NY 10940
• 

  

  /32

  $389,999

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  44 Orchard Hill, Middletown, NY 10941

  Welcome to 44 Orchard Hill Road, a classic ranch set on a tree-lined lot in the Pine Bush School District, with mature trees and a wide flat backyard. Inside, the kitchen has been refreshed with stainless appliances and a gas range, opening into a bright family room with a reclaimed wood accent wall. Down the hall, three bedrooms and a full bath keep things simple and comfortable. The walkout

  JOHN SCARANO Keller Williams Realty

  44 Orchard Hill, Middletown, NY 10941
• 

  

  /36

  $349,000

  $50K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  4 Lorelei Dr, Middletown, NY 10940

  This 3 bedroom home is being offered by the original owners. Three spacious bedrooms. Family room with custom fireplace. Oversized garage with laundry. Elementary and middle schools just down the road. Middletown High School offers many college courses. Beautiful sunroom with pellet stove. Two 275 gal oil tanks. Beautiful spacious back yard with shed. Extra black topped parking for RV, boat

  Sue Laden ARC Realty 1 in Sales

  4 Lorelei Dr, Middletown, NY 10940
• 

  

  /5

  $300,000

  • Land
  • 6 Acres
  • $50,000 per Acre

  0 Mount Hope Rd, Middletown, NY

  Looking to build? Land available in prime location. Situated directly between Middletown and Town of Mount Hope with easy access to all major roadways. Zoned for residential and agriculture. Buyer/builder to subdivide 5-6 acres from this 37+ acre parcel as agreeable to seller and proposed in contract. Flat, open, cleared land may be suitable for 1-3 building lots. Land to purchase provides

  Amanda Ferrantello Hudson Valley Griffith

  0 Mount Hope Rd, Middletown, NY
• 

  

  /22

  $479,000

  • 3 Beds
  • 1.5 Baths
  • 1,592 Sq Ft

  3 Sharon Dr, Middletown, NY 10941

  Welcome Home to 3 Sharon Drive! Sitting on just under half an acre in a tranquil, quiet neighborhood, this beautiful split-level home offers 3 bedrooms, 1.5 baths, and over 1,500 square feet — you'll feel right at home the moment you walk in the door! As you enter, you're greeted by tall ceilings that complement the spacious, open layout throughout. Just off the living room you have a spacious

  Ryan Barrett Keller Williams Realty

  3 Sharon Dr, Middletown, NY 10941
• 

  

  /20

  $305,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 689 Sq Ft

  15 Anthony St, Middletown, NY 10940

  *Welcome Home!* This exceptional *fully furnished and professionally designed* single-family residence is a rare turnkey opportunity, offering the perfect combination of style, comfort, convenience, and value. Beautifully updated and thoughtfully appointed, this approximately *690+/- sq. ft.* home is ready for immediate enjoyment—simply bring your personal belongings and move right in. The

  Eliezer Salcer Preferred Properties Real Esta

  15 Anthony St, Middletown, NY 10940
• 

  

  /48

  $435,000

  $14K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,041 Sq Ft

  60 Peach Place, Middletown, NY 10940

  Welcome to Swan Village Estates conveniently located just minutes from Highways, stores and shopping. If space is what you need, this three-level , corner lot townhome offers that and more inside and out! The main level features a bright living room with plenty of natural window light followed by a dining area and a spacious eat-in kitchen with stainless steel appliances with plenty of cabinet

  Sandra Arnez KW Hudson Valley United

  60 Peach Place, Middletown, NY 10940
• 

  

  /15

  $399,999

  • 3 Beds
  • 2.5 Baths
  • 1,496 Sq Ft

  21 Evan Ct, Middletown, NY 10940

  Welcome to 21 Evan Court, a beautifully maintained 3-bedroom, 2.5-bath home offering approximately 1,500 square feet of comfortable living space, plus additional finished basement space and a one-car garage. Situated on a quiet cul-de-sac in a desirable Middletown neighborhood, this home delivers the perfect blend of space, functionality, and convenience.Step inside to discover bright and

  Marquise Fulmore HomeSmart Homes & Estates

  21 Evan Ct, Middletown, NY 10940
• 

  

  /43

  $333,000

  $2K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,473 Sq Ft

  51 Deer Ct Dr, Middletown, NY 10940

  Welcome to this townhouse-style condo in Middletown, offering 2 bedrooms and 2.5 bathrooms. The first floor features a functional layout with a kitchen that opens to a dining area, a spacious living room, and a half bath. The kitchen offers a practical galley-style layout with ample cabinetry and counter space for everyday living. The open-concept living area provides a flexible layout for

  Jie Liu KW Hudson Valley United

  51 Deer Ct Dr, Middletown, NY 10940
• 

  

  /40

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,136 Sq Ft

  37 California Dr, Middletown, NY 10940

  GORGEOUS turn-key home located in the outskirts of Middletown with Minisink schools. Do NOT let the outside fool you as this home is much larger than expected... Step inside this Raised Ranch that is in mint condition with the upgrades it offers. Open floor layout from Living room to dining area & kitchen. New hardwood floors in upper level, vinyl floors in lower level and recessed lighting

  Sandra Arnez KW Hudson Valley United

  37 California Dr, Middletown, NY 10940
• 

  

  /20

  $360,000

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  14 Jackson Ave, Middletown, NY 10940

  Welcome home to this beautifully maintained 3-bedroom, 1-bath residence nestled on a picturesque street in a desirable location. From the moment you arrive, you’ll appreciate the inviting front porch, manicured grounds, and exceptional curb appeal that showcase years of meticulous care and maintenance. Inside, you’ll find a spacious living room, a formal dining room and a lovely eat-in kitchen

  Jennifer Kubler eRealty Advisors, Inc

  14 Jackson Ave, Middletown, NY 10940
• 

  

  /50

  $499,900

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

  37 Meadow View Dr, Middletown, NY 10940

  Welcome to this beautifully updated end-unit townhouse with numerous upgrades completed in 2023! The bright and open main level features hardwood flooring, a spacious kitchen with granite countertops, a complementary tile backsplash, stainless steel appliances, abundant cabinetry, a large center island, pendant lighting, and recessed lighting. The kitchen flows seamlessly into the dining area and

  Jie Liu KW Hudson Valley United

  37 Meadow View Dr, Middletown, NY 10940
• 

  

  /6

  $599,000

  $31K PRICE DROP

  • 10 Beds
  • 4 Baths

  309-317 E Main St Unit 309, Middletown, NY 10940

  Welcome to this beautiful two-family home located on E Main Street! Perfect for owner-occupants, investors, or extended family living, this spacious property offers incredible flexibility and charm. One unit features 6 bedrooms, while the second unit offers 4 bedrooms, providing plenty of spac. Both units have separate front and side entrances for added privacy and convenience. The property sits

  Betzaida Vericain Q Home Sales

  309-317 E Main St Unit 309, Middletown, NY 10940
• 

  

  /16

  $389,000

  • 4 Beds
  • 2 Baths
  • 1,416 Sq Ft

  4 Harding St, Middletown, NY 10940

  Middletown Central Gem with Lots of Space and Super Low Taxes!Located just minutes from Downtown Middletown, this solid house has a very practical layout with 4 spacious bedrooms and 2 full bathrooms, making it perfect for a growing family or an investor. On top of the great living space, you get a huge attic and a full basement that give you tons of extra room for storage or a workshop. The

  Hai Li KW Hudson Valley United

  4 Harding St, Middletown, NY 10940
• 

  

  /50

  $325,000

  • 2 Beds
  • 1 Bath
  • 1,117 Sq Ft

  68 Ridgewood Ave, Middletown, NY 10940

  Beautifully renovated ranch-style home offering modern updates and exceptional outdoor space in the heart of Middletown. This move-in ready home features brand-new flooring, fresh paint throughout, and an updated kitchen with quartz countertops and stainless steel appliances. Sliding glass doors lead to a spacious patio overlooking a huge level backyard, perfect for entertaining, relaxing, or

  Bryan Dale eXp Realty

  68 Ridgewood Ave, Middletown, NY 10940
• 

  

  /16

  $499,000

  $196K PRICE DROP

  • Land
  • 5.07 Acres
  • $98,422 per Acre

  0 Route 28 Unit 20261954, Middletown, NY 12455

  Rare opportunity: PRIME waterfront commercial lot in the heart of Margaretville on State Highway 28 -- unmatched visibility on the busy corridor. Zoned commercial with municipal sewer and water available. The East Branch of the Delaware River parallels the full length of the parcel, providing exceptional waterfront exposure and strong development potential. Seller has detailed plans available

  Katherine Keys The Catskill Dream Team

  0 Route 28 Unit 20261954, Middletown, NY 12455
• 

  

  /49

  $529,900

  • 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
• 

  

  /25

  $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
• 

  

  /37

  $549,000

  • 4 Beds
  • 2.5 Baths
  • 2,680 Sq Ft

  25 Georges Rd, Middletown, NY 10941

  Looking for a spacious Colonial in Middletown, NY, with room to grow and an easy NYC commute? Welcome to 25 Georges Road, a 4-bedroom, 2 full baths, and a half bath home offering 2,680 square feet of living space on a quiet residential street. Built in 1985, this home features a classic center hall layout, generous living areas, a brick fireplace, a large eat-in kitchen with abundant cabinetry, a

  Matthew Gibbs KW Hudson Valley United

  25 Georges Rd, Middletown, NY 10941
• 

  

  /14

  $393,000

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  1 Chestnut St, Middletown, NY 10940

  Beautifully renovated 3 bedroom 1 bathroom, everything is brand new, electrical, plumbing and heating, plus with a big corner lot. Plenty of space, beautiful kitchen - come see it today.

  Safdar Mursalin eXp Realty

  1 Chestnut St, Middletown, NY 10940
• 

  

  /22

  $395,000

  $55K PRICE DROP

  • 1,450 Sq Ft

  13 Benton Ave, Middletown, NY 10940

  Beautiful Brick Mixed Use Building located in a very desirable area of Middletown. This wonderful building features 3 Units. First unit is Office SpaceThat is great for an accountant, attorney,Real Estate office. Etc. Second Level offers a Spacious 1 Bedroom apartment 3 rd level offers another large 1 bedroom Apartment. Separate Electric and Hot water heaters. Large Parking Lot Second

  John Biasi Howard Hanna Rand Realty

  13 Benton Ave, Middletown, NY 10940
• 

  

  /21

  $560,000

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

  77 Upper Rd, Middletown, NY 10940

  This beautiful ranch-style property is ready to move in. Amazing upgrades were made to this home with beautiful hardwood floors, 4 bedrooms, 3 bathrooms, a huge finished basement with 3 additional rooms for storage or home office, and it also has space for a personal gym with access to an amazing backyard that features a beautiful above-ground pool, a tennis court, volleyball court, or basketball

  Yajaira Silva Madison Allied LLC

  77 Upper Rd, Middletown, NY 10940
• 

  

  /42

  $575,000

  $15K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,053 Sq Ft

  45 Randall Heights, Middletown, NY 10940

  PRESIDENTIAL HEIGHTS welcomes you to make this LUXURY CONTEMPORARY home yours today! Set in the highly desirable Presidential Heights neighborhood, known for its beautiful homes, peaceful atmosphere, and close proximity to everyday essentials. A large wrap around blacktopped driveway along with paver stone walkway leads you inside this newly remodeled gem. Discover an incredible blend of space,

  Sandra Arnez KW Hudson Valley United

  45 Randall Heights, Middletown, NY 10940
• 

  

  /33

  $499,999

  Open Sat 1PM - 3PM

  • 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
• 

  

  /24

  $555,000

  $24K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,202 Sq Ft

  29 Murray Rd, Middletown, NY 10940

  3 PRIVATE ACRES + ULTIMATE VERSATILITY + POSSIBLE INCOME POTENTIAL = A RARE MIDDLETOWN OPPORTUNITY Set on 3 serene, wooded acres, this beautifully maintained raised ranch offers an expansive 2,202 sq. ft. of living space designed with a unique, highly adaptable layout that can help with your financial goals or adapt to your lifestyle. The main level features a bright open-concept main floor with

  Regina Lombardo KW Hudson Valley United

  29 Murray Rd, Middletown, NY 10940
• 

  

  /16

  $329,000

  • 2 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  15 N Aspen Rd, Middletown, NY 10940

  NO HOA FEES! LOW TAXES!! Welcome to easy, effortless living in this turnkey, move-in ready 2-bedroom home, thoughtfully updated with modern finishes and designed for today’s lifestyle. From the moment you step inside, you’re greeted by a bright and inviting interior that feels both stylish and comfortable. The updated kitchen shines with sleek countertops, crisp cabinetry, and modern appliances,

  Carmela Lopez Borrazas Serhant LLC

  15 N Aspen Rd, Middletown, NY 10940
• 

  

  /4

  $470,000

  • 3 Beds
  • 2.5 Baths
  • 1,723 Sq Ft

  22 Atwood Dr, Middletown, NY 10940

  Coming Soon! Beautiful 3 BR, 2.5 baths.

  Kelly Roebuck Curasi Realty, Inc.

  22 Atwood Dr, Middletown, NY 10940

Showing Results 41 - 80, Page 2 of 3