Homes for Sale near Middletown High School

• 

  

  

  /50

  $489,000

  • 3 Beds
  • 2.5 Baths
  • 1,827 Sq Ft

  37 Lindentree Ln, Mechanicstown, NY 10940

  Welcome home to this lovely 3-bedroom townhouse in the heart of Middletown. The main level features an open, airy floor plan that flows seamlessly from the kitchen into the living room, dining room, and breakfast area — perfect for everyday living and entertaining alike.The primary suite is your private retreat, complete with an en-suite bath featuring a double sink and a relaxing soaking

  

  Donna Reese

  KW Hudson Valley United

  37 Lindentree Ln, Mechanicstown, NY 10940
• 

  Explore Middletown High School

• 

  

  

  /44

  $599,000

  $70K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,225 Sq Ft

  23 Orange Terrace, Middletown, NY 10940

  Experience a one-of-a-kind custom-built A-Frame that blends rustic charm with modern luxury. Nestled on a quiet street in the city, this stunning home commands attention with its reflective tinted windows, dramatic architecture, and incredible curb appeal.Designed for both entertaining and everyday living, the expansive wraparound deck features a built-in wired speaker system, creative

  

  Joao Rodrigues

  Preferred Properties Real Esta

  23 Orange Terrace, Middletown, NY 10940
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  /25

  $160,000

  $5K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft

  226 Concord Ln, Middletown, NY 10940

  Renovated in 2021 is this first floor 1 bedroom condo in Buttonwood conveniently located close to Rte 17 and 84 for those of you commuting a distance to work. Just turn the key and move in, no work is needed. Kitchen has newer cabinets with crown molding and stainless LG appliances with a convection/air fry oven that can be controlled by your phone along with granite counters. Kitchen counter has

  

  Lynelle Alessi

  KW Hudson Valley United

  226 Concord Ln, Middletown, NY 10940
• 

  

  

  /31

  $299,900

  • 3 Beds
  • 1 Bath
  • 860 Sq Ft

  256 Cottage St Unit 258, Middletown, NY 10940

  The first thing you will do here is walk out into that lawn and start deciding where everything goes, the garden along the sunny side, the fire pit set well back, the patch under the old shade tree that stays empty because that is the coolest spot on the property and you are going to want it for yourself. The lot is 0.28 acres, flat and open, and every bit of it comes with the keys. Not many city

  

  Brian Caplicki

  KW Hudson Valley United

  256 Cottage St Unit 258, Middletown, NY 10940
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  /50

  $799,000

  $96K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,296 Sq Ft

  411 Mt Joy Rd, Middletown, NY 10941

  Space, privacy, and thoughtful design come together at this well-maintained 4-bedroom, 2.5-bath Colonial, built in 2005, offers 3,296 sq ft of living space on 11.7 private acres—giving you room to breathe while staying conveniently close to everything Middletown has to offer.Step inside and you'll immediately notice the 9-foot ceilings that elevate every room with an airy, open feel. The main

  

  Donna Reese

  KW Hudson Valley United

  411 Mt Joy Rd, Middletown, NY 10941
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  /33

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,328 Sq Ft

  3 Allerton Ave, Middletown, NY 10940

  Welcome to 3 Allerton Ave, a charming and well-maintained Ranch-style home nestled in one of Middletown’s sought-after neighborhoods. Set on a private 0.20-acre lot, this inviting property offers a peaceful suburban setting with shopping, dining, public transportation, and commuter routes just minutes away. A welcoming front porch leads into a bright foyer and semi-open living space connecting

  

  Erin Connolly-Frontino

  Artisan Realty

  3 Allerton Ave, Middletown, NY 10940
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  /43

  $399,900

  $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,919 Sq Ft

  83 Deer Ct Dr, Middletown, NY 10940

  Beautifully renovated 3-bedroom, 2.5-bathroom, 1-car garage, two-story townhouse located in the highly desirable Deer Run complex. This move-in-ready home features laminate flooring throughout, with tile flooring in the kitchen and bathrooms. The kitchen was tastefully updated in 2020, along with the heating and cooling system, which is electronically controlled and offers a high-efficiency SEER

  

  Dulce M Ferrera

  KW Hudson Valley United

  83 Deer Ct Dr, Middletown, NY 10940
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  /26

  $339,900

  $20K PRICE DROP

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

  101 N Beacon St, Middletown, NY 10940

  Move in ready 3 bedrooms, 2 bathroom home. Clean and freshly painted. Updated kitchen and bathrooms. Located on a dead end street. Private Fenced-in yard. Conveniently located minutes from local shops, restaurants, Galleria Mall, Garnet Health and close proximity to I86 and I84. Very easy to show. Call today for your own private viewing.

  

  Dulce M Ferrera

  KW Hudson Valley United

  101 N Beacon St, Middletown, NY 10940
• 

  

  /35

  $980,000

  New Construction

  • 6 Beds
  • 6 Baths
  • 4,480 Sq Ft

  5-7 Blanchard St, Middletown, NY 10940

  Brand new construction duplex in heart of Middletown. Each spacious unit features 3 bedrooms, 2.5 baths, garage, central A/C and a bright, sun-filled open floor plan thoughtfully designed for today's lifestyle. Beautiful kitchens with expansive windows create an abundance of natural light, with one unit showcasing elegant dove white cabinetry while the other offers rich espresso cabinetry, both

  

  JoAnn Maxwell

  Howard Hanna Rand Realty

  5-7 Blanchard St, Middletown, NY 10940
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  /3

  $285,000

  • 2 Beds
  • 1 Bath
  • 1,019 Sq Ft

  16 Earle St Unit 14 1/2, Middletown, NY 10940

  Prime opportunity for investors, renovators, or savvy buyers looking to build instant sweat equity. With some TLC and modern updates, you can bring your vision to life and transform this house into a standout primary residence or high-yield rental investment.Unbeatable Location & Convenience:Walkable: Walking distance to SUNY Orange campus, downtown amenities, and local

  

  Joao Rodrigues

  Preferred Properties Real Esta

  16 Earle St Unit 14 1/2, Middletown, NY 10940
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  /33

  $475,000

  • 4 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  8 Pine St, Middletown, NY 10940

  Come view this beautifully appointed Raised Ranch in a commuter-friendly area of Middletown . This 4 bedroom two bath home boasts an open kitchen concept with 4 generous sized bedrooms upstairs an open downstairs area that can become anything you desire. It comes fully equipped with all appliances. You will also enjoy the spacious canopied deck and pool. Act now and you can bein this wonderful

  Robin White KW Hudson Valley United

  8 Pine St, Middletown, NY 10940
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  /28

  $399,000

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

  19 Putters Way Unit 6, Middletown, NY 10940

  Beautiful Townhouse in Fairways at Wallkill! Enjoy maintenance-free living in this desirable Fairways community townhouse. Conveniently located near major highways, shopping, and Orange Regional Medical Center, this home features 2 bedrooms, 2.5 bathrooms, a spacious living room, and a bright private balcony overlooking the pool.Residents have access to outstanding amenities including a

  Xiaohui Cui KW Hudson Valley United

  19 Putters Way Unit 6, Middletown, NY 10940
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  /31

  $359,000

  • 3 Beds
  • 1.5 Baths
  • 1,388 Sq Ft

  21 Black Stallion Ct, Middletown, NY 10940

  Welcome to inviting, freshly painted, updated 3-bedroom, 1.5-bathroom home in The Meadows community~Main floor offers kitchen-with brand new cabinets, new stainless steel appliances, granite countertops, roomy dining area, bright and expansive living room with large bay window and half bathroom~Door from the kitchen leads to the large deck perfect for relaxing and entertaining your guests

  Liene Kasparsons Keller Williams Realty

  21 Black Stallion Ct, Middletown, NY 10940
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  /23

  $349,000

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

  15 Kendal Ln, Middletown, NY 10940

  Beautifully maintained end-unit townhouse in the highly desirable Water's Edge community! This move-in-ready 2-bedroom, 2.5-bath home offers a bright, open layout with a spacious foyer, updated kitchen featuring newer appliances, a large living room with new sliding glass doors leading to a private patio, and a convenient first-floor powder room. Upstairs, the primary suite features cathedral

  Jonathon Lee KW Hudson Valley United

  15 Kendal Ln, Middletown, NY 10940
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  /20

  $420,000

  • 3 Beds
  • 2.5 Baths
  • 2,097 Sq Ft

  4 Kless Ct, Middletown, NY 10940

  Welcome to Maple Fields! This well-maintained 3-bedroom, 2.5-bath townhouse with a versatile finished loft offers a functional layout designed for today's lifestyle.The main level features an open-concept living area, a dedicated dining space, and a bright kitchen with stainless steel appliances, a pantry, tile backsplash, and ample counter space. Sliding glass doors open to a private

  Bryant Moran YourHomeSold Guaranteed Realty

  4 Kless Ct, Middletown, NY 10940
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  /40

  $775,000

  $125K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,991 Sq Ft

  121 Coutant Rd, Circleville, NY 10919

  A beautifully maintained country home surrounded by gardens, lawn and towering trees.Welcome to Chestnut Ridge Farm.Approached by a winding drive and nestled among mature shade trees, this beautifully maintained country home offers a rare combination of privacy, character, and timeless appeal.Set on meticulously landscaped grounds, the property welcomes you with expansive lawns,

  Donna Brooks Compass Greater New York, LLC

  121 Coutant Rd, Circleville, NY 10919
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  /45

  $224,900

  $64K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,131 Sq Ft

  32 Tarbell Rd, Bloomingburg, NY 12721

  Charming Cape Cod situated on a private setting surrounded by mature trees and established landscaping. This 2-bedroom, 1-bath home offers a flexible layout with generously sized rooms, abundant natural light, and multiple living spaces to accommodate a variety of needs.The eat-in kitchen features ample cabinetry and workspace, while the additional interior spaces provide opportunities for a

  Chaim Friedman KW Hudson Valley United

  32 Tarbell Rd, Bloomingburg, NY 12721
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  /42

  $215,000

  • 1 Bed
  • 1 Bath
  • 879 Sq Ft

  11 Brittany Dr, Middletown, NY 10940

  Welcome to a low-maintenance lifestyle, minimal utilities, included heat and hot water, generous storage, and a commuter-friendly setting. This condominium is an excellent opportunity for buyers looking for comfort and convenience . Located in a quiet, peaceful neighborhood, this second-floor condo offers a welcome retreat while still being close to varied amenities and transportation options

  Amanda Ferrantello Hudson Valley Griffith

  11 Brittany Dr, Middletown, NY 10940
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  /13

  $530,000

  $30K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 1,911 Sq Ft

  35 Dogwood Dr, Middletown, NY 10940

  Just pack your bags and move in. Spacious, Comfortable and Cozy 5 bedroom 1 family house for sale. This house features 4 Bedrooms and 2 bathrooms on the upper level with a walk in closet and a bathroom in the master bedroom. The first features a 1/2 bath, renovated kitchen, separate living and dinning rooms and a walkout deck. The ground floor features a 2 car garage, finished basement with 1

  Lenworth Brisco Keller Williams Realty NYC Grp

  35 Dogwood Dr, Middletown, NY 10940
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  /44

  $370,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,413 Sq Ft

  6 Charlotte Mews, Middletown, NY 10940

  New renovation, New split air conditioner,New floor ,NEW painting, New toilet on the first floor,New refrigerator, new washing machine, new dryer, garage renovationBeautifully maintained detached townhome in Canterbury Knolls is very convenient to highway, train station and major shopping. Homeowner fee covers lawn maintenance, snow removal, garbage pickup and use of clubhouse. This home

  Zhiheng Tang KW Hudson Valley United

  6 Charlotte Mews, Middletown, NY 10940
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  /50

  $599,000

  Pre-Foreclosure

  • 4 Beds
  • 2.5 Baths
  • 2,428 Sq Ft

  977 Mt Hope Rd, Middletown, NY 10940

  3.8 acres + privacy + a substantial 4-bedroom Colonial.Your own private retreat in Middletown — with the space you've been looking for. This beautiful property offers plenty of privacy and room to enjoy both indoor and outdoor living.Step inside and you'll immediately appreciate the beautiful hardwood floors, high ceilings, and abundance of natural light throughout. The spacious center

  Georgina T. Maynard Charles Rutenberg Realty, Inc.

  977 Mt Hope Rd, Middletown, NY 10940
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  /47

  $420,500

  • 3 Beds
  • 1.5 Baths
  • 1,656 Sq Ft

  34 Adams Ave, Middletown, NY 10940

  Welcome to this charming 3-bedroom, 1.5-bath Colonial nestled on a level, fenced lot in the heart of Middletown. Built in 1941, this well-maintained home beautifully blends timeless character with everyday functionality, showcasing original hardwood floors, classic woodwork, detailed moldings, and elegant arched doorways throughout.The inviting first floor features a spacious living room,

  Linda Potyak Iron Valley RE Tri-State

  34 Adams Ave, Middletown, NY 10940
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  /49

  $579,000

  • 4 Beds
  • 3 Baths
  • 2,368 Sq Ft

  34 Hawthorne Dr, Middletown, NY 10940

  Welcome to Wildflower at Wallkill, Orange County's premier 55+ community! Something Special! This 4 BR, 3 bath beauty is open and sun filled with vaulted ceilings and lovely detailed chair railings! 10 ft. ceilings and new wood floors throughout 1 st floor! Large LR opens to DR! Kitchen with island and undercounter lighting opens to vaulted family room with gas fireplace! Primary suite is on

  Linda Clark Hudson Valley Griffith

  34 Hawthorne Dr, Middletown, NY 10940
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  /49

  $394,000

  $25K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,928 Sq Ft

  48-50 Mountain Ave, Middletown, NY 10940

  Welcome to 48-50 Mountain Avenue, where timeless Cape Cod charm meets modern comfort in one of Middletown's most convenient locations. Beautifully updated and meticulously maintained, this inviting 3-bedroom, 1.5-bath home offers approximately 1,928 square feet of warm, light-filled living space on a beautifully landscaped 0.36-acre lot tucked away on a quiet cul-de-sac. From the moment you

  Amanda Brehm KW Hudson Valley United

  48-50 Mountain Ave, Middletown, NY 10940
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  /47

  $739,000

  $60K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,085 Sq Ft

  3 Truman Ct, Middletown, NY 10940

  Step into 5-bedroom Colonial-style home, where classic charm meets upscale upgrades. From the moment you enter, you’re welcomed by exquisite craftsmanship, including detailed crown molding and rich hardwood floors that flow seamlessly throughout the main living spaces.This spacious residence features three elegant fireplaces, creating warm and inviting focal points across multiple living

  Dominick Tufano RE/MAX Benchmark Realty Group

  3 Truman Ct, Middletown, NY 10940
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  /34

  $539,900

  • 4 Beds
  • 2.5 Baths
  • 2,176 Sq Ft

  31 Denman Rd, Middletown, NY 10940

  Welcome to this beautifully maintained Center Hall Colonial offering the perfect blend of classic design and comfortable everyday living. The heart of the home is the spacious kitchen, which opens seamlessly to the inviting family room, creating an ideal space for gathering with family and friends. The family room is highlighted by custom built-in shelving and a cozy wood-burning fireplace,

  Kenyatta Jones-Arietta R2M Realty Inc

  31 Denman Rd, Middletown, NY 10940
• 

  

  /18

  $179,000

  New Construction $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  412 4th Ave, Middletown, NY 10940

  This beautiful high end home is located in the desirable Valley View Community. The home is brand new and offers a modern contemporary feel and it is ready to be yours! Ideal commuter friendly location just minutes to the train to NYC. Bright and airy 2 bedroom, 2 bath home with close to 1,000 square feet of space! Gorgeous gourmet kitchen with upgraded cabinets featuring an abundance of

  Sandra Spector Howard Hanna Rand Realty

  412 4th Ave, Middletown, NY 10940
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  /4

  $1,650,000

  • Land
  • 7.5 Acres
  • $220,000 per Acre

  32 Gibbs Ct, Middletown, NY 10940

  32 Gibbs Court | Wallkill, NYPrime 3.20 Acre Commercial Development PAD on 7.5-acre lot Opportunity in the Heart of WallkillUnlock the full potential of this premier 3.20 PAD on a 7.5-acre commercial parcel, ideally located in the thriving Town of Wallkill. Situated within the highly desirable Town Center District, 32 Gibbs Court offers a rare development opportunity with broad zoning

  Peter Janis Berkshire Hathaway HS NE Prop.

  32 Gibbs Ct, Middletown, NY 10940
• 

  

  /49

  $399,900

  • 3 Beds
  • 1.5 Baths
  • 2,210 Sq Ft

  10 Creeden Dr, Middletown, NY 10940

  Welcome to 10 Creeden Drive in Middletown! Set on 1.1 acres along a quiet road, this property offers a spacious, level yard, large driveway, two-car detached garage, and a brand-new deck—perfect for relaxing or entertaining. Paid-off solar panels provide added value and potential energy savings, while the full unfinished basement offers plenty of storage and possibilities for future use. The home

  Devon King HomeSmart Homes & Estates

  10 Creeden Dr, Middletown, NY 10940
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  /24

  $349,000

  • Land
  • 43.4 Acres
  • $8,041 per Acre

  64 Seaman Rd, Scotchtown, NY 10941

  Nestled in a serene and private setting, this 43+ acre property is a rare find, offering endless possibilities for those seeking a dream home or recreational retreat. Positioned on a desirable flag lot, the land ensures seclusion while still being accessible. A gated graveled driveway leads to a cleared homesite area, ready for construction. The level, wooded landscape is enhanced by a network of

  Antoinette Gundersen HomeSmart Homes & Estates

  64 Seaman Rd, Scotchtown, NY 10941
• 

  

  /35

  $424,999

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

  11 Sunnyside Ave, Middletown, NY 10940

  Calling all investors and future house hackers! This versatile duplex is the perfect opportunity to grow your rental portfolio or offset your mortgage by living in one unit while renting the other.Each apartment offers 2 bedrooms and 1 full bathroom, featuring spacious living areas, an open-concept layout, and generously sized bedrooms. One of the units also includes a dedicated office

  Valerie Jewis Keller Williams Realty

  11 Sunnyside Ave, Middletown, NY 10940
• 

  

  /18

  $499,000

  • 4 Beds
  • 2 Baths
  • 1,932 Sq Ft

  12 Walnut Ln, Middletown, NY 10940

  Beautifully maintained home in a desirable Middletown neighborhood featuring a bright, functional layout and a spacious backyard. One of the most valuable features of this property is its flexible bedroom layout. Four total bedrooms, including two conveniently located on the first floor, offering rare flexibility for multi-generational living, guests, a home office, or easy single-level living.

  Xiaohui Cui KW Hudson Valley United

  12 Walnut Ln, Middletown, NY 10940
• 

  

  /14

  $319,000

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

  35 Lexington Way, Middletown, NY 10940

  Prime Location & NeighborhoodCommuter Convenience: Minutes from Route 17 (Future I-86), Interstate 84, and the Middletown Metro-North train station, providing a straightforward commute toward NYC and Westchester.Proximity to Key Amenities: Close to Garnet Health Medical Center, SUNY Orange, and the Route 211 commercial corridor (major shopping centers, dining, and grocery

  Zhiheng Tang KW Hudson Valley United

  35 Lexington Way, Middletown, NY 10940
• 

  

  /35

  $474,995

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,084 Sq Ft

  1 High Ridge Ln, Middletown, NY 10940

  Welcome to refined, low maintenance living in one of Middletown’s most sought after gated communities. This beautifully maintained end unit townhouse offers the perfect balance of space, comfort, and convenience, with over 2,000 square feet of living space designed for today’slifestyle. Step inside to find a bright and inviting layout featuring spacious bedrooms each with generous closet

  Jason Madison eXp Realty

  1 High Ridge Ln, Middletown, NY 10940
• 

  

  /46

  $539,000

  • 3 Beds
  • 2.5 Baths
  • 2,225 Sq Ft

  18 Hickory Place, Middletown, NY 10941

  Welcome to this beautifully maintained 3-bedroom, 2.5-bath bi-level home, built in 2010 and offering 2,225 square feet of comfortable living space. Designed with an open-concept layout, this impressive residence features a well-appointed kitchen with granite countertops, abundant cabinetry, and a seamless flow into the dining and living areas—ideal for both everyday living and

  Anita S. Cristiano HomeSmart Homes & Estates

  18 Hickory Place, Middletown, NY 10941
• 

  

  /27

  $399,900

  $50K PRICE DROP

  • 5 Beds
  • 3 Baths

  37 Monhagen Ave, Middletown, NY 10940

  Welcome to an opportunity that is becoming harder and harder to find. This multi-family property sits on a nearly half-acre lot in the City of Middletown and offers investors, contractors, and ambitious buyers the chance to create significant value. With 2,151 square feet, five bedrooms, three full bathrooms, and income-producing potential, this is the type of property that rewards vision and

  Isaiah Lopez KW Hudson Valley United

  37 Monhagen Ave, Middletown, NY 10940
• 

  

  /32

  $559,000

  $40K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,929 Sq Ft

  1 Parkview Dr, Middletown, NY 10940

  Welcome to 1 Parkview Dr. in beautiful Presidential Park in Middletown, NY. Located on a corner lot, this expanded raised ranch shines. Gleaming hardwood floors and spacious room size are only some if it's great features. Eat in kitchen boasts an atrium that looks out to its lovely landscaped backyard. Spend time in this space and you'll feel like you're on vacation. Beautiful inground pool is

  Marie Altieri Howard Hanna Rand Realty

  1 Parkview Dr, Middletown, NY 10940
• 

  

  /5

  $169,900

  • Land
  • 4.2 Acres
  • $40,452 per Acre

  0 Dosen Rd Unit KEY1005907, Wallkill Town, NY 10940

  Tucked away with exceptional privacy, yet just minutes from everything you need — this lot places you within 15 minutes of Middletown's vibrant dining, grocery, and shopping destinations. The location is truly unmatched: Garnet Health Medical Center, Middletown Medical Center, and Orange County Community College are all within easy reach, making this an ideal home base for those who require both

  Patricia Sassi RE/MAX Benchmark Realty Group

  0 Dosen Rd Unit KEY1005907, Wallkill Town, NY 10940
• 

  

  /50

  $498,000

  • 4 Beds
  • 3 Baths
  • 1,716 Sq Ft

  9 Ashland Ave Unit 11, Middletown, NY 10940

  Welcome to this well-maintained 4-bedroom, 3-full-bath home offering a functional layout and comfortable living spaces. The welcoming entry features an elegant chandelier and a large arched window that fills the home with natural light. The main level offers hardwood floors, vaulted ceilings, recessed lighting, a comfortable living room, and a separate dining area overlooking the backyard. The

  Jie Liu KW Hudson Valley United

  9 Ashland Ave Unit 11, Middletown, NY 10940
• 

  

  /6

  $799,000

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

  Lot 2 Winters Ln, Middletown, NY 10940

  Welcome to your dream home! This stunning new construction craftsman-style home is now being built on Lot 2 of the coveted Lane Meadow Farm subdivision, located in the Town of Mamakating, Sullivan County, NY. Enjoy the serenity and natural beauty of one of Sullivan County's newest and most sought-after neighborhoods, where peaceful country living meets exceptional craftsmanship. Featuring

  Jacob Silberstein Parcel Realty LLC

  Lot 2 Winters Ln, Middletown, NY 10940

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