Middletown, NY Homes for Sale

• 

  

  

  /41

  $399,000 Open Sun 1PM - 3PM

  • 2 Beds
  • 1.5 Baths
  • 1,036 Sq Ft

  15 Clark St, Middletown, NY 10940

  Charming cape with water views on quiet street with boat launch! A total dream! House was recently renovated both inside and out. The recently painted rich, navy blue siding pops as you pull up alongside the newly built stone wall to welcome family and friends. The interior has been updated with new paint and flooring. Neutral colors and touches of shiplap throughout make the whole home very

  Hilary Ryan Goldman Howard Hanna Rand Realty

  15 Clark St, Middletown, NY 10940
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /38

  $998,000

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  255 Howells Rd, Middletown, NY 10940

  Enter the gates of this grand estate, where you'll find a stunning 5-bedroom, 5-bathroom home spanning 4,200 square feet, complete with a large barn and a natural pond, all set on 36.8 acres. This private estate is located in Middletown, NY, nestled among rolling pastures, tranquil woods, and your very own pond. The expansive property also features a two-story post-and-beam barn with horse

  Jonathon Lee Keller Williams Hudson Valley

  255 Howells Rd, Middletown, NY 10940
• 

  

  

  /26

  $349,900

  • 2 Beds
  • 2.5 Baths
  • 1,241 Sq Ft

  24 Kent Ct, Middletown, NY 10940

  Elegant 2-Bedroom, 3-Bath End Unit in Sought-After Waters Edge CommunityWelcome to this beautifully maintained 2-bedroom, 2.5-bath end-unit condo in the desirable Waters Edge community—where comfort meets convenience in a peaceful, lakefront setting. Designed for easy living, this home offers a bright, open layout filled with natural light and modern charm.The first floor features

  Jonathon Lee Keller Williams Hudson Valley

  24 Kent Ct, Middletown, NY 10940
• 

  

  

  /48

  $399,999

  • 3 Beds
  • 3 Baths
  • 2,236 Sq Ft

  19-21 Wilson St, Middletown, NY 10940

  Check out this spacious 3 bedroom, 3 full bathroom Ranch-style home nestled in the heart of the City of Middletown within the Middletown School District. Designed with comfort and functionality in mind, this home offers plenty of room for everyday living, entertaining, and multi-generational needs. Step inside to a warm and inviting layout featuring a large eat-in kitchen with abundant oak

  JOHN SCARANO Keller Williams Realty

  19-21 Wilson St, Middletown, NY 10940
• 

  

  

  /43

  $419,900

  • 3 Beds
  • 3 Baths
  • 2,214 Sq Ft

  242 Derby Rd, Middletown, NY 10940

  Some homes simply check the boxes. Others feel like they were built with care from the ground up. 242 Derby Road is one of those rare finds, offering the peace of mind that comes with knowing every detail is brand new.From the curb, you’ll notice the fresh siding, new roof, and paved driveway. Inside, over 2,094 square feet of modern comfort welcome you with natural light, clean finishes,

  Isaiah Lopez Keller Williams Hudson Valley

  242 Derby Rd, Middletown, NY 10940
• 

  

  /41

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,256 Sq Ft

  138 Camp Orange Rd, Middletown, NY 10941

  Welcome to this 3-bedroom, 1-bath ranch nestled on 1.4 peaceful acres, offering both privacy and opportunity. With its single-level living, this home is a great fit for first-time buyers, downsizers, or anyone ready to put their personal touch on a property with solid bones. Inside, you’ll find an inviting layout ready for updates—walls, ceilings, and flooring await your vision to transform this

  Annmarie Kovacs Howard Hanna Rand Realty

  138 Camp Orange Rd, Middletown, NY 10941
• 

  /2

  $60,000

  • Land
  • 0.11 Acre
  • $522,648 per Acre

  14 W Conkling Ave, Middletown, NY 10940

  Welcome to 14 W Conklin Ave! This rare opportunity allows you to build your dream home on a vacant lot in the heart of Middletown. Nestled on a quiet street, the lot offers a serene atmosphere while being within walking distance to Orange County Community College. The surrounding area boasts numerous parks and playgrounds, providing a great outdoor experience. The property is conveniently located

  Travis Thompson Keller Williams Hudson Valley

  14 W Conkling Ave, Middletown, NY 10940
• 

  

  /38

  $325,500

  • 4 Beds
  • 1.5 Baths
  • 1,496 Sq Ft

  8 Park Row, Middletown, NY 10941

  Welcome to this beautifully renovated, well-maintained, and completely move-in ready 4-bedroom, 1.5-bath townhouse in Middletown, NY. Offering a bright and inviting layout, this home features modern updates throughout and plenty of space for comfortable living. The main level features a spacious eat-in kitchen with a generous pantry and a thoughtfully designed and efficient kitchen complete with

  Vanessa Wight BHG Real Estate Green Team

  8 Park Row, Middletown, NY 10941
• 

  

  /27

  $289,900

  • 2 Beds
  • 2 Baths
  • 1,291 Sq Ft

  78 Deer Ct Dr, Middletown, NY 10940

  This bright and spacious third-floor corner condo in the sought-after Deer Run community offers two bedrooms and two full baths with an open floor plan ideal for both everyday living and entertaining. Sunlight streams through a wall of windows into the combined living and dining area, while the kitchen provides abundant cabinetry and a generous pantry. The primary suite features a large walk-in

  Eva Kusmierek eXp Realty

  78 Deer Ct Dr, Middletown, NY 10940
• 

  

  /40

  $355,000

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft

  29 Red Barn Ln, Middletown, NY 10940

  Welcome to 29 Red Barn Lane, a beautiful home tucked away in one of Middletown’s most desirable neighborhoods. This property combines comfort, style, and convenience—perfect for today’s lifestyle.Step inside and you’ll be greeted by a warm, open layout designed for both everyday living and entertaining. The spacious living room flows seamlessly into a bright dining area and a modern

  Kevin Grier Keller Williams Hudson Valley

  29 Red Barn Ln, Middletown, NY 10940
• 

  

  /3

  $60,000

  • Land
  • 0.11 Acre
  • $522,648 per Acre

  43 Clinton St, Middletown, NY 10940

  Welcome to 43 Clinton St! This rare opportunity allows you to build your dream home on a vacant lot in the heart of Middletown. Nestled on a quiet street, the lot offers a serene atmosphere while being within walking distance to Orange County Community College. The surrounding area boasts numerous parks and playgrounds, providing a great outdoor experience.The property is conveniently located

  Travis Thompson Keller Williams Hudson Valley

  43 Clinton St, Middletown, NY 10940
• 

  

  /33

  $399,900

  • 1 Bed
  • 1 Bath
  • 1,088 Sq Ft

  727 Route 17m, Middletown, NY 10940

  A Truly Unique Opportunity – Live, Work, or Both!Welcome to a property that perfectly blends charm, function, and versatility. This special offering is not only a wonderful place to call home but also provides incredible potential to operate your own business—all in a convenient, easily accessible location.Currently configured as a single-family residence with mixed-use potential, this

  Frank Muccari Cronin & Company Real Estate

  727 Route 17m, 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 architect-owner later added a striking

  Jacob Matthews Ellis Sotheby's Intl Realty

  441 Scotchtown Collabar Rd, Middletown, NY 10941
• 

  

  /26

  $329,000

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  136 & 140 Gillen Rd, Middletown, NY 10940

  Welcome to your affordable new home just off Route 17M! This charming 3-bedroom ranch offers incredible value that beats the recent appraisal. Enjoy the comfort of central A/C and peace of mind with a durable metal roof. The best part? The assumable lease on the solar panels delivers dramatically low electric bills, putting more money back in your pocket every month!The sale includes two

  Karie Boniface Cronin & Company Real Estate

  136 & 140 Gillen Rd, Middletown, NY 10940
• 

  

  /35

  $175,000

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft

  238 Concord Ln, Middletown, NY 10940

  Welcome to this beautifully updated two-bedroom, two-bathroom condominium in the heart of Middletown! This move-in-ready home features brand-new flooring throughout, a fully remodeled kitchen with modern appliances and finishes, and an updated furnace for optimal comfort and efficiency. Ideally situated in a prime location, this property offers easy access to shopping, dining, entertainment, and

  Andi Berisha BHHS Hudson Valley Properties

  238 Concord Ln, Middletown, NY 10940
• 

  

  /21

  $899,990

  • 6 Beds
  • 3 Baths

  30 Royce Ave, Middletown, NY 10940

  Welcome to 30 Royce Ave, a rare opportunity in the heart of Middletown! This spacious duplex offers incredible versatility, perfect for owner-occupants looking to offset their mortgage with rental income, or savvy investors seeking a property with strong cash-flow potential.Each unit features generous living space with 3 bedrooms and 1 bath, offering comfort and functionality for families

  Anthony Rivas Keller Williams Hudson Valley

  30 Royce Ave, Middletown, NY 10940
• 

  

  /35

  $350,000

  • 2 Beds
  • 1.5 Baths
  • 1,584 Sq Ft

  1 Lake Ridge Dr, Middletown, NY 10940

  Nestled in the sought-after Lake Ridge at Water’s Edge community in Middletown, NY, this beautifully maintained end-unit townhouse offers a perfect blend of comfort, style, and convenience. Featuring 2 bedrooms and 1.5 baths, the home boasts modern touches throughout, including luxury vinyl flooring, recessed LED lighting, and a cozy gas fireplace. The kitchen is equipped with stainless steel

  Colin Seitz RE/MAX Benchmark Realty Group

  1 Lake Ridge Dr, Middletown, NY 10940
• 

  

  /44

  $630,000 Open Sun 12PM - 2PM

  • 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
• 

  

  /43

  $544,900

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

  841 Howells Turnpike, Middletown, NY 10940

  Welcome to 841 Howells Turnpike – Your Private Retreat in the Pine Bush School District Set on 1.3 park-like acres, 3-bedroom, 2.5-bath contemporary colonial offers a blend of timeless charm, spacious living, and total privacy all nestled in the heart of the Hudson Valley and just 5 miles from the train station to NYC. As you arrive, a long paved driveway winds through a wooded approach, passing

  Alyse Toffel Keller Williams Hudson Valley

  841 Howells Turnpike, Middletown, NY 10940
• 

  

  /10

  $299,999

  • Land
  • 27.2 Acres
  • $11,029 per Acre

  328 Bloomingburg Rd, Middletown, NY 10940

  Vacant Property directly across from Fair Oaks Drive in Movie theater and a gas station with plenty of road frontage!! Minutes to RT17. 27.2 ACRES!!! Electric on road at the front of the property! Possible small farm, Big enough for horses, growing crops, family compound. R2 Zoning.The owner is currently using the property to grow crops and has an Agricultural tax exemption. NO engineering

  Jeffrey Lyons Curasi Realty, Inc.

  328 Bloomingburg Rd, Middletown, NY 10940
• 

  

  /24

  $349,999

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft

  53 Richmond Place, Middletown, NY 10940

  Beautifully renovated two-story home in Orange County! Featuring a brand-new kitchen with granite countertops and modern appliances, stunning flooring throughout, a first-floor laundry area, and a cozy covered wrap-around porch! Upstairs, you'll find three bedrooms, a full bath, and a walk-up attic for convenient storage. The yard is mostly fenced, offering safety for kids and pets, with an

  Kelly Roebuck Curasi Realty, Inc.

  53 Richmond Place, Middletown, NY 10940
• 

  /2

  $350,000

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft

  8 Hill Rd, Middletown, NY 10941

  Looking for a home you can make your own without breaking the bank? This 924 sq ft ranch style home on 4 private acres with direct Wallkill River access is a rare opportunity! This home needs some cleanup and finishing touches inside. You could move right in and update as you go! New Roof & New Septic, the big updates are already done. The Detached Garage needs a new roof and renovations.

  Nancy LaBarbera Keller Williams Hudson Valley

  8 Hill Rd, Middletown, NY 10941
• 

  

  /49

  $599,999

  • 5 Beds
  • 3.5 Baths
  • 2,504 Sq Ft

  166 Brown Rd, Middletown, NY 10941

  Charming 5-Bedroom, 3.5-Bathroom Home with In-ground Pool, Modern Updates & Historic AppealStep into this modernized historic home, where timeless charm meets contemporary luxury. This 5-bedroom, 3.5-bathroom beauty features two primary suites, including a first-floor primary with an ensuite bathroom, offering flexibility and privacy. The updated kitchen includes quartz countertops,

  Harmoni VanEtten eXp Realty

  166 Brown Rd, Middletown, NY 10941
• 

  

  /42

  $349,000

  • 4 Beds
  • 1 Bath
  • 1,790 Sq Ft

  38 Prospect St, Middletown, NY 10940

  Welcome to this charming well maintained 1900's Colonial centrally located to everything Middletown has to offer such as schools, walking distance to the Elk's Club, YMCA and Downtown Middletown finest eateries and breweries!, shopping and public transportation. When you arrive to the property the large porch will great you and once you step inside you will notice the old charm starting with

  Pedro Garcia Curasi Realty, Inc.

  38 Prospect St, Middletown, NY 10940
• 

  

  /16

  $169,900

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  985 Route 17m, Middletown, NY 10940

  Welcome to your brand-new home! This beautiful 2024-built 2-bedroom, 2-bathroom mobile home offers 900+ square feet of thoughtfully designed living space — perfectly blending comfort, style, and affordability. Features Include:Open-Concept Living Area: Spacious layout filled with natural light, featuring stylish wood-look flooring throughout.Modern Kitchen: Equipped with

  Steven Brown Hudson Valley Realty & Busines

  985 Route 17m, Middletown, NY 10940
• 

  

  /22

  $99,000

  • Land
  • 3 Acres
  • $33,000 per Acre

  OO Dimmick Mountain Rd, Middletown, NY 12430

  2.75 ACRE SCENIC LOT WITH NYC DEP APPROVALS - DIMMICK MOUNTAIN RD, MIDDLETOWN, NY ADDRESS: DIMMICK MOUNTAIN ROAD, MIDDLETOWN, NY 12455.................................... LOT SIZE: 2.75 ACRES TYPE: VACANT LAND - RESIDENTIAL ZONING UTILITIES: ELECTRIC ON-SITE, EXISTING DUG WELL PROPERTY OVERVIEW WELCOME TO YOUR PERFECT CATSKILLS RETREAT OPPORTUNITY...........................................A

  Joseph Lombardo LOMBARDO HOMES & ESTATES

  OO Dimmick Mountain Rd, Middletown, NY 12430
• 

  

  /50

  $969,999

  • 3 Beds
  • 3 Baths
  • 3,282 Sq Ft

  346 Mullock Rd, Middletown, NY 10940

  Welcome to 346 Mullock Road – A Private Pondside Mini-Estate in the Heart of the Hudson ValleyTucked away down a long, tree-lined drive in the sought after Minisink Valley School District, this 3-bedroom, 3-bathroom contemporary sanctuary unfolds across 3300+ sqft of architecturally distinctive living space, set on 5.4 private, park-like acres with not one, but two spring-fed ponds teeming

  Alyse Toffel Keller Williams Hudson Valley

  346 Mullock 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
• 

  

  /16

  $65,000

  • Land
  • 4.66 Acres
  • $13,948 per Acre

  Tbd Running Horse Rd, Middletown, NY 12455

  Tucked away on a private dead end road, this 4.66-acre parcel offers the perfect balance of seclusion and accessibility. The property features a generous, usable area at the front that's easily accessible from the road—ideal for siting your home, cabin, or weekend retreat. As the land stretches back, the terrain becomes steeper, adding character and natural privacy. The wooded setting provides a

  Teresa Falkowski Keller Williams Realty HV Nort

  Tbd Running Horse Rd, Middletown, NY 12455
• 

  

  /18

  $225,000

  • 2 Beds
  • 2 Baths
  • 995 Sq Ft

  302 Concord Ln, Middletown, NY 10940

  Welcome to Buttonwood Hill Condominiums! This first-floor 2-bedroom, 2-bath unit offers easy living with a private feel. The open layout features a spacious living and dining area that flows to a walk-out patio overlooking the woods — the perfect spot for morning coffee or evening relaxation. The kitchen provides ample storage and workspace, while the primary suite includes a full bath and

  Windy Rosengart R2M Realty Inc

  302 Concord Ln, Middletown, NY 10940
• 

  

  /44

  $324,999

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft

  20 Benton Ave, Middletown, NY 10940

  Discover the potential in this charming 3-bedroom, 2-full-bath two-story home with 1,504 sq ft of living space. Full of character and solid construction, this property offers a formal dining room and plenty of room to grow with a full unfinished attic and full, unfinished, walk-out basement featuring washer/dryer hookups.Featuring strong bones and charming original touches, this home is

  Vincent Reda Keller Williams Realty

  20 Benton Ave, Middletown, NY 10940
• 

  

  /24

  $349,999

  • 2 Beds
  • 1 Bath
  • 736 Sq Ft

  128 Kleis Road Spur, Middletown, NY 12430

  Welcome to Your Catskills Retreat at 128 Kleis Road SpurTucked away on a quiet spur road and surrounded by evergreens, this charming single-level cabin blends cozy comfort with outdoor living.Relax on the spacious deck, soak in the private hot tub, or gather by the fire pit under the stars. Inside, enjoy an open layout with large windows, a stone fireplace, and sliders to the deck—perfect

  Michelle Andzel Graziano Four Seasons Sotheby's International Realty

  128 Kleis Road Spur, Middletown, NY 12430
• 

  

  /14

  $349,000

  • 3 Beds
  • 1.5 Baths
  • 1,604 Sq Ft

  1 Chancery Mews, Middletown, NY 10940

  Welcome to this spacious and well-maintained contemporary-style home located in the sought-after Canterbury Knolls community. Featuring 3 bedrooms, 2 bathrooms, this home offers comfortable and functional living for today’s modern lifestyle. The inviting living room includes a cozy fireplace, while sliding glass doors lead to a private patio—perfect for entertaining or enjoying peaceful evenings

  Sean Walker Keller Williams Realty

  1 Chancery Mews, Middletown, NY 10940
• 

  

  /11

  $150,000

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  55 Glen Ave, Middletown, NY 10940

  Single faming home in the wonderful Middletown, NY up for grabs. Needs renovation. This is a fixer-upper on a large .34 acre lot. Don't miss out.

  Ishwar Rameshar YourHomeSold Guaranteed Realty

  55 Glen Ave, Middletown, NY 10940
• 

  

  /34

  $384,000

  • 2 Beds
  • 2.5 Baths
  • 1,677 Sq Ft

  28 Pinto Rd W, Middletown, NY 10941

  Welcome to this stunning, better-than-new townhome located in the highly sought-after community of Liberty Commons. Just one year young, this impeccably maintained residence offers the perfect blend of modern luxury, comfort, and convenience. Step inside to discover a light-filled open layout featuring gleaming hardwood floors on the main level and plush carpeting upstairs. The designer kitchen

  Juan Bautista Keller Williams Realty

  28 Pinto Rd W, Middletown, NY 10941
• 

  

  /12

  $269,900

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

  17 N Aspen Rd, Middletown, NY 10940

  This renovated 2-bedroom, 1.5-bath townhouse in Middletown offers a perfect blend of comfort and convenience! The inviting living room, filled with natural light, leads into a modern kitchen with brand-new stainless steel appliances and an adjacent washer/dryer setup. The dining room features a sliding door that opens up to a private fenced-in backyard—ideal for outdoor relaxation or

  Jonathon Lee Keller Williams Hudson Valley

  17 N Aspen Rd, Middletown, NY 10940
• 

  

  /28

  $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
• 

  

  /27

  $349,990

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft

  9 Genung St, Middletown, NY 10940

  Charming two-story home in the heart of Middletown! This spacious residence offers a welcoming front porch, perfect for relaxing evenings, and a practical layout filled with natural light. The home features multiple bedrooms, ample living space, and a generous yard with off-street parking. Located in a convenient neighborhood close to schools, shopping, dining, and major highways, this property

  Anthony Rivas Keller Williams Hudson Valley

  9 Genung St, Middletown, NY 10940
• 

  

  /22

  $425,000

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

  19 Putters Way Unit 9, Middletown, NY 10940

  Welcome to this fully updated, move-ready condo in the desirable Walkill community. This splendid duplex has been luxuriously 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

  Abraham Lefkowitz Access Realty Team Inc

  19 Putters Way Unit 9, Middletown, NY 10940
• 

  

  /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

Showing Results 41 - 80, Page 2 of 4