Middletown, NY Homes for Sale

• 

  

  

  /12

  $65,000

  $10K PRICE INCREASE

  • Land
  • 7,875 Sq Ft
  • $359,513 per Acre

  538 E Main St, Middletown, NY 10940

  Residential land avaiable on East Main Street, close to the Crystal Medical center, close to NYS HWY 17, close to the Galleria Mall, close to the new Resorts and Casino about 30 milles away, close to the Poconos, come built you new home here.Attached to this listing are documents from the building dept to help you, Make sure to see the documents attached.

  Frank Rivera Hudson Valley Home Connection

  538 E Main St, Middletown, NY 10940
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  /50

  $299,000

  $11K PRICE DROP

  • 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
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  /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
• 

  

  

  /19

  $333,000

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  23 Harrison St Unit 25, Middletown, NY 10940

  Come see this well maintained 2 story colonial style home. Centrally located in the City of Middletown which allows you to be minutes away to all the great eateries and to all major shopping and public transportation. The home has taken a few updates over the years. Home has a spacious living room that leads into a formal dining room. Kitchen has plenty of cabinet space as well. The central a.c

  Pedro Garcia Curasi Realty, Inc.

  23 Harrison St Unit 25, Middletown, NY 10940
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  /49

  $465,000

  • 3 Beds
  • 2 Baths
  • 1,545 Sq Ft

  168 Shawangunk Rd, Middletown, NY 10940

  Discover the perfect blend of historic charm, modern comfort, and peaceful country living in this utterly delightful home, beautifully situated on 2.2 wooded acres. Rich in character, the residence showcases timeless architectural details while benefiting from a comprehensive renovation. Prior to renovation, the home was thoroughly gutted and fully foam insulated, with all-new plumbing and

  Jason Kerwar William Raveis Real Estate

  168 Shawangunk Rd, Middletown, NY 10940
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  /3

  $179,900

  • Land
  • 3.15 Acres
  • $57,111 per Acre

  182 Pocatello Rd, Middletown, NY 10940

  Build your dream home on this fully engineered and Town of Wallkill-approved 3+ acre parcel, located within the desirable Middletown School District. This ready-to-build lot offers the perfect combination of privacy and convenience, with a peaceful setting while remaining just minutes from major highways, shopping, dining, and everyday amenities. A rare opportunity to own a fully approved

  Jonathon Lee KW Hudson Valley United

  182 Pocatello Rd, Middletown, NY 10940
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  /49

  $370,000

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

  15 Old Anvil Ln, Middletown, NY 10940

  Welcome to 15 Old Anvil Ln, Middletown, a lovingly cared for end unit townhouse in the sought after "The Meadows" community. This unit has been lived in and cared for by the same owners for approximately 40 years. The owner is a builder so he has not skipped on his own improvements and care. The unit offers 3 bedrooms and 2.5 bathrooms, a kitchen and formal dining room with a slider to a

  Valeria Rios KW Hudson Valley United

  15 Old Anvil Ln, Middletown, NY 10940
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  /13

  $85,000

  • Land
  • 5.1 Acres
  • $16,667 per Acre

  Lot 11 Meadowbrook Dr, Middletown, NY 12455

  Just a short drive from down town Margaretville, tucked away in the pastoral rolling hills, sits this very special 5 acre parcel with lovely open views. What this parcel has to offer is sure to check many boxes on your wish list. A peaceful and serene setting with beautiful scenic views, rolling open meadows backed by magical woods to explore, surrounded by the sounds of nature. With several

  Rosalie Glauser Frank Lumia Real Estate Plus

  Lot 11 Meadowbrook Dr, Middletown, NY 12455
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  /49

  $475,000

  • 4 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  8 Comfort Rd, Middletown, NY 10941

  Comfort is more than just the address at 8 Comfort Rd. This beautifully maintained 4-bedroom, 2½-bath home offers inviting spaces designed for comfortable everyday living and entertaining. The main level features hardwood flooring throughout the living room, dining room, and bedrooms, along with an updated kitchen complete with a center island, granite countertops, abundant cabinetry, and plenty

  Jo-Ann Campagiorni Houlihan Lawrence Inc.

  8 Comfort Rd, Middletown, NY 10941
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  /33

  $400,000

  • 4 Beds
  • 2 Baths
  • 2,241 Sq Ft

  34 Spring St, Middletown, NY 10940

  Welcome to 34 Spring Street, a spacious multi-family property offering a total of 4 bedrooms and 2 full bathrooms. This versatile home presents an excellent opportunity for investors, owner-occupants, or buyers seeking a flexible living arrangement for extended family. Live in one unit while renting the other, or add both residences to your investment portfolio for potential rental income. Each

  Kerri Stretch Howard Hanna Rand Realty

  34 Spring St, Middletown, NY 10940
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  /32

  $479,000

  • 3 Beds
  • 2.5 Baths
  • 2,198 Sq Ft

  32 Woodstock Ln, Middletown, NY 10941

  Charming 3 bedroom, 2.5 bath home close to everything with Pine Bush Schools! Perfectly positioned just 2 minutes off of 211 in the heart of Middletown, you're just moments away from everything! Shopping, dining, transit and the areas most convenient commuter routes are all within 2 miles of this warm and inviting home. Step from the impressive entry foyer into a spacious open concept living and

  Anne Mahoney Hudson Valley Home Connection

  32 Woodstock Ln, Middletown, NY 10941
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  /44

  $324,000

  Open Sun 1PM - 3PM $31K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,830 Sq Ft

  122 Castle High Rd, Middletown, NY 10940

  Set on approximately 2 acres, this 1920’s unique multi-level home provides plenty of room to enjoy the outdoors. A standout feature is the property's unique location, offering road frontage on two separate roads, Castle High Road and Eatontown Road and both Agricultural and Residential zoning. Whether you've dreamed of creating your own homestead, raising chickens or other livestock, planting

  Denise Clancy Curasi Realty, Inc.

  122 Castle High Rd, Middletown, NY 10940
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  /12

  $135,000

  • Land
  • 5,000 Sq Ft
  • $1,175,958 per Acre

  43 Clinton St, Middletown, NY 10940

  The parcel is shovel-ready with ALL Approvals and ready for you to build. Included in the land sale are the Building Plans, the Survey, the Building Department Approvals for the Building Plan, and the Permit to start building. You are welcome to use your own building plans. Buy "AS-IS". Current Property Owner/Builders can build this house plan for you... OR... your plans. This sale is NOT

  Lena Silk National Veterans Realty Group

  43 Clinton St, Middletown, NY 10940
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  /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
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  /10

  $415,000

  Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 1,625 Sq Ft

  23 W Conkling Ave, Middletown, NY 10940

  BEAUTIFUL turn-key home located in a quiet neighborhood behind Orange County Community College of 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

  Sandra Arnez KW Hudson Valley United

  23 W Conkling Ave, Middletown, NY 10940
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  /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
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  /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
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  /20

  $339,000

  • 2 Beds
  • 1 Bath
  • 894 Sq Ft

  17 State St, Middletown, NY 10940

  Welcome to 17 State St, a fully updated, energy-efficient detached home offering modern smart-home features and exceptional flexibility. The bright main level features central air, smart climate control, a beautifully tiled bathroom, custom window blinds with a transferable lifetime warranty, and an updated kitchen with premium stainless-steel appliances, including a brand-new smart refrigerator.

  Olivia Torres eXp Realty

  17 State St, Middletown, NY 10940
• 

  

  /15

  $85,000

  • Land
  • 5.1 Acres
  • $16,667 per Acre

  Lot 11 Meadow Brook Dr, Middletown, NY 12455

  Just a short drive from down town Margaretville, tucked away in the pastoral rolling hills, sits this very special 5 acre parcel with lovely open views. What this parcel has to offer is sure to check many boxes on your wish list. A peaceful and serene setting with beautiful scenic views, rolling open meadows backed by magical woods to explore, surrounded by the sounds of nature. With several

  Rosalie Glauser Listing by Frank Lumia Real Estate Plus!, LLC

  

  Lot 11 Meadow Brook Dr, Middletown, NY 12455
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  /35

  $200,000

  • Land
  • 51.7 Acres
  • $3,868 per Acre

  Tbd Hall Rd, Middletown, NY 12455

  Hike up to see this spectacular 51.7 acres of prime Real Estate. This property has everything except a road which will have to be built. A previous right of way was moved years ago due to flooding. The walk in does require waterproof boots and a lot of good energy. The parcel has every kind of topography you could imagine. Mouch of it is a large lightly wooded plateau. The southeastern boundary

  William Chris St. John Win Morrison Realty

  Tbd Hall Rd, Middletown, NY 12455
• 

  

  /21

  $299,900

  Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,884 Sq Ft

  2 S Aspen Rd, Middletown, NY 10940

  Say hello to possibility! A Middletown townhouse with space, flexibility, and room to make it your own. With 3 bedrooms, and a main-level flex space w/ closet, 2.5 bathrooms, plus inviting outdoor space, this home is ready for your personal touch. Close to everything Middletown offers—shops, dining, parks, and commuter routes—this is a smart move with big potential. Make 2 S. Aspen Rd your next

  Derek Greene Greene Realty Group

  2 S Aspen Rd, Middletown, NY 10940
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  /38

  $399,900

  $20K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,204 Sq Ft

  39 California Ave, Middletown, NY 10940

  More space than meets the eye! This well-maintained 4-bedroom home features two first-floor bedrooms, a first-floor full bath, an enclosed sunroom, a full basement, a detached two-car garage, and a deep, level backyard. Notable improvements include a new roof, gutters, electrical panel, and exterior painting (2024); a new driveway (2023); whole-home updates in 2018 including new flooring

  Guoqing Ouyang Dalton Wade Inc.

  39 California Ave, Middletown, NY 10940
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  /46

  $450,000

  • 3 Beds
  • 1.5 Baths
  • 1,640 Sq Ft

  21 Manhattan Ave Unit 19, Middletown, NY 10940

  **Opportunities on Manhattan Avenue are few and far between. If you've been waiting for a home in this desirable neighborhood, your wait is over! ** Situated on a beautiful .25-acre lot, this inviting split-level offers the perfect combination of comfort, space, and style with **3 bedrooms, 1.5 baths, a one-car garage, and central air**.From the moment you walk through the door, you'll

  Rosalie Cook Weichert Realtors

  21 Manhattan Ave Unit 19, Middletown, NY 10940
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  /38

  $669,999

  $59K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,284 Sq Ft

  168 Pine Grove Rd, Middletown, NY 10940

  Update - priced to sell! Imagine waking up surrounded by three private acres while still being just minutes from shopping and major commuter routes. This newly built colonial offers the peace of country living without sacrificing convenience. The open-concept kitchen, oversized island, fireplace, spacious primary suite and unfinished basement provide room to grow while giving buyers the

  Leeshai Lemish Panorama Realty

  168 Pine Grove Rd, Middletown, NY 10940
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  /8

  $659,000

  $41K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 2,040 Sq Ft

  2467 Route 302, Middletown, NY 10941

  Excellent location and property seeking a savvy investor. Pine Bush schools, fully leased near Highway and less than 5 miles to train. Close to shopping too. Hurry to see before it is gone.

  Myrna Lattore eRealty Advisors, Inc

  2467 Route 302, Middletown, NY 10941
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  /11

  $1,475,000

  • Land
  • 92.31 Acres
  • $15,979 per Acre

  0 Red Kill Rd, Middletown, NY 12430

  92.30 acres for sale in the Catskill Mountains New York.This secluded and versatile property is now for sale for the first time since 1996. Set above the charming Village of Fleischmanns and just 0.6 miles from Main Street, this 92-acre parcel offers the privacy of a wilderness retreat with the convenience of a village doorstep.-Interior roadways.-A large man-made spring-fed pond and

  peter neumann Listing by Keller Williams Upstate NY Properties

  

  0 Red Kill Rd, Middletown, NY 12430
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  /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
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  /39

  $505,000

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

  111 Jasmine Dr, Middletown, NY 10940

  Welcome to Wildflower at Wallkill, one of the Hudson Valley's premier 55+ communities, where beautifully maintained grounds, outstanding amenities, and a true sense of community create an exceptional place to call home. Residents enjoy a beautiful clubhouse, fitness center, business center, indoor and outdoor swimming pools, tennis courts, recreation facilities, gated entry, and professionally

  Christina D'Altilio Coldwell Banker Choice Prop.

  111 Jasmine Dr, Middletown, NY 10940
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  /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
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  /49

  $499,999

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft

  81 Silver Lake Scotchtown Rd Unit 4, Middletown, NY 10940

  Experience modern living in this newly built 3-bedroom, 2.5-bath home designed with comfort and style in mind. Featuring an open floor plan with soaring 10-foot ceilings, this home offers spacious living and entertaining areas filled with natural light. The gourmet kitchen boasts granite countertops, stainless steel appliances, and ample cabinetry, all flowing seamlessly into the main living

  Antoinette Gundersen HomeSmart Homes & Estates

  81 Silver Lake Scotchtown Rd Unit 4, Middletown, NY 10940
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  /2

  $395,000

  • 3 Beds
  • 1 Bath

  23 Bonnell St, Middletown, NY 10940

  2 family home in low traffic setting. 1st floor is 3 bedroom @ $1350./month plus utilities 2nd floor is 2 bedroom @ $1100/mo plus utilities Ist floor lease is annual until July 2027. 2nd floor month to month.Old storage building out back. Taxes about $500/mo insurance about $150./mo water about $50./mo

  Mark Tierney Howard Hanna Rand Realty

  23 Bonnell St, Middletown, NY 10940
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  /44

  $799,999

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  TBD Brook Rd, Middletown, NY 10941

  New Construction LUXURY HOME in Valley Central Schools outside of SCOTCHTOWN! "Choose Your Finishes" on this Stunning 3,000 sq. ft. modern Colonial privately set atop a scenic 5-acre wooded lot offering privacy and natural beauty. Conveniently located 5-10 minutes to Middletown, Pine Bush, and Montgomery. The main level features a spacious open-concept floor plan with 9-foot ceilings, hardwood

  Philip Barnao eXp Realty

  TBD Brook Rd, Middletown, NY 10941
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  /41

  $749,900

  • 4 Beds
  • 2.5 Baths
  • 2,906 Sq Ft

  512 County Route 49, Middletown, NY 10940

  Welcome to this stunning, meticulously maintained Chesterfield Colonial offering breathtaking views, exceptional updates, and true move-in-ready condition. From the moment you enter the impressive two-story foyer, you'll appreciate the bright, open-concept design and abundance of natural light streaming through every window. The spacious main living areas are perfect for both everyday living and

  Jonathon Lee KW Hudson Valley United

  512 County Route 49, Middletown, NY 10940
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  /48

  $419,000

  $30K 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
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  /10

  $299,999

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

  328 Bloomingburg Rd, Middletown, NY 10940

  Fully Available!! 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.

  Jeffrey Lyons Curasi Realty, Inc.

  328 Bloomingburg Rd, Middletown, NY 10940
• 

  

  /15

  $394,999

  $5K PRICE DROP

  • 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
• 

  

  /39

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,688 Sq Ft

  276 Spruce Rd, Middletown, NY 10940

  If you've been searching for a home with space, privacy, and room to make it your own, this Colonial is ready to welcome you home. Nestled on 5 beautiful acres, where privacy, nature, and comfortable living come together, this 4-bedroom, 2.5 bath home offers approximately 2,688 square feet of living space with plenty of room to spread out. The traditional two-story layout provides generous living

  Christine Torres KW Hudson Valley United

  276 Spruce Rd, Middletown, NY 10940
• 

  /2

  $25,000

  $2K PRICE DROP

  • Land
  • 1,393 Sq Ft
  • $781,250 per Acre

  138-1/2 Linden Ave, Middletown, NY 10940

  Lot is vacant and directly between 138 & 140 Linden Ave

  Olivia Cappelli Donna Ruffino Realty Corp

  138-1/2 Linden Ave, Middletown, NY 10940
• 

  

  /18

  $695,000

  $55K PRICE DROP

  • 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
• 

  

  /29

  $289,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,181 Sq Ft

  21 Dolson Ave, Middletown, NY 10940

  The home offers 2 bedrooms plus an additional room that works well as an office or flex space, 1 full bathroom, and a functional kitchen. The backyard is a standout — generous in size with a large deck, great for warm weather. A walk-out basement adds useful storage. Washer/dryer hookup in unit. Currently tenant-occupied at $2,300/month, making this a ready-to-go investment from day one. Close to

  Jacob Fried Keller Williams Realty

  21 Dolson Ave, Middletown, NY 10940

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