Recently Sold Middletown Homes

• 

  $375,000 Sold Sep 12, 2025

  • 1,440 Sq Ft
  • $260/SF
  • 80 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1920

  22 Maryland Ave, Middletown, NY 10940

  If you’ve been dreaming of a home that feels like a true retreat but keeps you close to everything you need — welcome to your perfect match.In a tranquil setting, this charming 3-bedroom home has been lovingly and meticulously cared for, sitting proudly on almost a half-acre of beautiful land. From the moment you pull into the paved driveway, you'll feel it — that special sense of

  Patricia Lucey Picture It Sold, LLC

  22 Maryland Ave, Middletown, NY 10940
• 

  Explore Middletown

• 

  $415,000 Sold Sep 10, 2025

  • 1,848 Sq Ft
  • $225/SF
  • 23 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1975

  21 Maple Dr, Middletown, NY 10940

  Move right into this charming cape cod style home. 4 oversized bedroom’s and 2 full bathrooms. Step out onto a second story oversized deck from one of the two massive upstair bedrooms. The home is packed with updates, including new flooring throughout, a cozy kitchen and a large bay window in the living room that maximizes natural lighting. A detached garage with plenty of storage in the loft

  David Ferstand Daf Realty

  21 Maple Dr, Middletown, NY 10940
• 

  $206,000 Sold Sep 10, 2025

  • 924 Sq Ft
  • $223/SF
  • 208 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 2023

  354 Concord Ln, Middletown, NY 10940

  Welcome to 354 Concord Lane! Renovated 2 bedroom 2 full bath condo in Buttonwood Hills with a great floor plan! This is a first floor condo and a great price! Why rent when you can own?? This condo is waiting for your special touches to make it your own! Some features include a Living Rm, Dining Rm, Renovated Kitchen 2018 with Stainless Steel appliances, Private Laundry, nice closet space, Master

  Zhiheng Tang Keller Williams Hudson Valley

  354 Concord Ln, Middletown, NY 10940
• 

  $315,000 Sold Sep 09, 2025

  • 920 Sq Ft
  • $342/SF
  • 75 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1923

  109 Lake Ave, Middletown, NY 10940

  Numerous updates and niceties abound in this move in ready 1920's ranch that's just a short walk from Davidge Park and a short ride to everything else that Middletown/Wallkill have to offer. New floors, Paint, updated bathrooms, updated kitchen and updated basement and more means you wont spend your spare time making renovations or improvements and can spend that precious time pursuing your

  Thomas Grazier I Realty LLC

  109 Lake Ave, Middletown, NY 10940
• 

  $403,000 Sold Sep 05, 2025

  • 1,056 Sq Ft
  • $382/SF
  • 38 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  12 Brewster Dr, Middletown, NY 10940

  Welcome to 12 Brewster Drive, a charming single-family home nestled in a peaceful neighborhood in Middletown. This delightful residence offers 3 bedrooms and 2 bathrooms within a comfortable amount of living space The home's inviting exterior features include NEWER Roofing & Siding along with a well-maintained lawn and mature landscaping, creating a warm and welcoming curb appeal. Inside,

  Philip Barnao eXp Realty

  12 Brewster Dr, Middletown, NY 10940
• 

  $374,300 Sold Sep 05, 2025

  • 1,788 Sq Ft
  • $209/SF
  • 57 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1935

  14 W Prospect Ave, Middletown, NY 10940

  Cape cod tudor, 3 beds, 1.5 baths

  Sharon Reynolds Keller Williams Hudson Valley

  14 W Prospect Ave, Middletown, NY 10940
• 

  $235,000 Sold Sep 04, 2025

  • 880 Sq Ft
  • $267/SF
  • 18 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2006

  181 Ruth Ct, Middletown, NY 10940

  Welcome to Eastview Condominium, offering a two-bed, two full bath ground-level condo! Conveniently located near the front door, with ample visitor parking. Ideally situated near Highways 84/17 and NJ Transit, enjoy easy access to Garnett Medical Center, Orange County Community College, as well as the growing list of amenities in and around Middletown, NY, all just 75 minutes from NYC. Call today

  Nicholas Cuomo Keller Williams Realty

  181 Ruth Ct, Middletown, NY 10940
• 

  $520,000 Sold Sep 04, 2025

  • 1,892 Sq Ft
  • $275/SF
  • 54 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1970

  21 Standish Ave, Middletown, NY 10940

  Fully renovated raised ranch in Middletown, NY! Features include a modern kitchen with quartz countertops, stainless steel appliances, and hardwood floors throughout. Spacious rooms offer comfort and versatility. Conveniently located in a great commuter spot—close to major highways, shopping, and more. Move-in ready and full of style!

  Haakim Byrd HomeSmart Homes & Estates

  21 Standish Ave, Middletown, NY 10940
• 

  $341,000 Sold Sep 03, 2025

  • 1,540 Sq Ft
  • $221/SF
  • 29 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1989

  45 Birch Dr, Middletown, NY 10940

  Welcome to 45 Birch Drive, a beautifully renovated and move-in-ready 3-bedroom, 1.5-bath townhouse offering modern updates, spacious living, and everyday comfort.Step inside to a bright and inviting layout updated lighting, and a flowing main level perfect for both relaxing and entertaining. The kitchen has been refreshed with modern appliances and custom cabinetry, offering style and

  Christopher Baum RE/MAX Benchmark Realty Group

  45 Birch Dr, Middletown, NY 10940
• 

  $440,000 Sold Sep 02, 2025

  • 2,748 Sq Ft
  • $160/SF
  • 101 Days On Market

  • 6 Beds
  • 2 Baths
  • Built 1910

  225 Highland Ave, Middletown, NY 10940

  Great Opportunity For Future Owner Occupant Or An Investor Who Is Looking To Collect $4,450 Of Current Rental Income With Tenants In Place.Fully Renovated In 2020. The Property Was Originally A 2 Family And Has Two Levels, Basement And A Full Attic. 2 Forced Hot Air Systems With Separate Gas And Electric Services. Both Sides Are Set With First Floor Kitchen With Door To Deck On Rear. Living Room

  Mark Karten Karten Real Estate Svcs LLC

  225 Highland Ave, Middletown, NY 10940
• 

  $400,000 Sold Aug 31, 2025

  • 1,406 Sq Ft
  • $284/SF
  • 103 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1926

  21 Wilkin Ave, Middletown, NY 10940

  Welcome to this charming 3-bedroom, 2-bathroom home nestled in the heart of Middletown, NY! This beautifully maintained property is in excellent condition, featuring a blend of classic charm and modern convenience. The spacious layout offers comfortable living with a formal dining room, perfect for family meals and entertaining guests.As you step inside, you'll immediately notice the

  Ben Schubert Richmont Realty

  21 Wilkin Ave, Middletown, NY 10940
• 

  $268,000 Sold Aug 29, 2025

  • 1,131 Sq Ft
  • $237/SF
  • 29 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1910

  197 Highland Ave, Middletown, NY 10940

  **Multiple offer situation. Seller requesting highest, best and final offers 12pm noon, 7/7/2025.** 3 Bedroom, 1.5 Bathroom Old Style Two Story home in Middletown! Close to shopping, schools and amenities. Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for

  Desiree Beecham River Realty Services, Inc.

  197 Highland Ave, Middletown, NY 10940
• 

  $235,000 Sold Aug 29, 2025

  • 1,000 Sq Ft
  • $235/SF
  • 29 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1989

  256 Concord Ln, Middletown, NY 10940

  This fully renovated two-bedroom, two-bath condo offers modern upgrades and stylish finishes throughout. The kitchen features brand-new appliances and elegant quartz countertops, while the bathrooms boast sleek porcelain countertops. Enjoy the comfort of brand-new vinyl flooring, plush carpeting, and a new boiler, along with the convenience of an in-unit washer and dryer. Two air conditioning

  Carol Cruz Keller Williams Hudson Valley

  256 Concord Ln, Middletown, NY 10940
• 

  $395,000 Sold Aug 28, 2025

  • 1,164 Sq Ft
  • $339/SF
  • 53 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1953

  7 Randall Terrace, Middletown, NY 10940

  Welcome to this beautifully renovated Cape-style home. This 3-bedroom, 1.5-bath residence also features a versatile den, perfect for a home office, guest room, or playroom. Recent renovations include new siding, flooring throughout, and a fully remodeled bathroom. The layout provides a warm and inviting atmosphere. Step outside to enjoy the large backyard, ideal for outdoor activities, gardening,

  Desiree Beecham River Realty Services, Inc.

  7 Randall Terrace, Middletown, NY 10940
• 

  $325,000 Sold Aug 25, 2025

  • 1,680 Sq Ft
  • $193/SF
  • 36 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1958

  25 Euclid Ave, Middletown, NY 10940

  Welcome home to 25 Euclid Ave located in the heart of Middletown, NY! This charming 3-bedroom, 1.5-bath ranch offers a welcoming and comfortable living space. The main level features gleaming hardwood floors that enhance the natural light flowing throughout. The eat-in kitchen provides ample cabinet space, perfect for all your culinary needs. The full basement is a versatile area, waiting for

  Maria Sairrino Cronin & Company Real Estate

  25 Euclid Ave, Middletown, NY 10940
• 

  $325,000 Sold Aug 24, 2025

  • 1,460 Sq Ft
  • $223/SF
  • 32 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1989

  23 Woodlake Dr, Middletown, NY 10940

  Welcome to the Spring Hollow Community. One of the few complexes that checks off all the boxes! This community offers a private pool, clubhouse and a pond and YES, it's an end unit! The location is centrally located to all shopping and major commuter highways. This home offers laminate flooring and updated kitchen with tiled back splash, eat in kitchen area as well as a formal dining area with

  Pedro Garcia Curasi Realty, Inc.

  23 Woodlake Dr, Middletown, NY 10940
• 

  $310,000 Sold Aug 22, 2025

  • 1,132 Sq Ft
  • $274/SF
  • 27 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1928

  29 Lafayette Ave, Middletown, NY 10940

  Perfect Starter Home or Investment Opportunity!Welcome to this charming 3-bedroom, 1-bath home—ideal for first-time homebuyers, savvy investors, or anyone looking for a fixer-upper with great potential. Step inside to find a spacious living room perfect for relaxing or entertaining, a dedicated dining room for family meals, and a bright kitchen ready for your personal

  Waldina Almazan RE/MAX Benchmark Realty Group

  29 Lafayette Ave, Middletown, NY 10940
• 

  $218,700 Sold Aug 22, 2025

  • 924 Sq Ft
  • $237/SF
  • 111 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1989

  374 Concord Ln, Middletown, NY 10940

  Experience the perfect blend of style and comfort in this newly renovated 2-bedroom, 2-bathroom condo. Freshly painted and thoughtfully upgraded, this stunning unit features newly upgraded bathrooms, kitchen with modern appliances and a private balcony overlooking a serene, peaceful view—ideal for relaxation. Situated in the most sought-after location within the community, this home offers

  Heather Martin United RE Hudson Valley Edge

  374 Concord Ln, Middletown, NY 10940
• 

  $475,000 Sold Aug 21, 2025

  • 2,890 Sq Ft
  • $164/SF
  • 31 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2020

  19 Woodrose Ct, Middletown, NY 10940

  Welcome to Highrose Ridge! This home offers 2890 sq ft of efficient space. Barely broken in at five years young, the home is Turn-key & Move-In Ready. This end unit is inviting from the moment you walk through the entrance, where you are greeted with an open floor plan with Formal Living Rm, Dining Area, Powder Rm, Oak Hardwood Floors and steps out to a semi private rear yard. The EIK is open

  Debbie Goldstein Howard Hanna Rand Realty

  19 Woodrose Ct, Middletown, NY 10940
• 

  $295,000 Sold Aug 21, 2025

  • 1,342 Sq Ft
  • $220/SF
  • 64 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1977

  87 Sycamore Dr, Middletown, NY 10940

  Welcome to this lovely 2-bedroom, 2 full bathrooms, well-kept condo located in the sought-after Clemson Park complex! This 2nd floor unit, one-level floor plan is beautifully maintained and boasts 1342 sq. ft of living space with a master suite with its own full bathroom, an additional bedroom and full bath, laundry room, eat-in kitchen, formal dining area, living room, built-in cabinets in the

  Jacqueline Henry-Thompson Jackie Henry Realty LLC

  87 Sycamore Dr, Middletown, NY 10940
• 

  $290,000 Sold Aug 20, 2025

  • 1,232 Sq Ft
  • $235/SF
  • 3 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1920

  20 Columbia Ave, Middletown, NY 10940

  Step across the sun-warmed front walk, swing open the original door, and feel possibility bloom.Beneath time-worn rugs, early-century hardwood floors wait for their first gleam of daylight. Sunshine pours through tall windows, skimming vintage trim and setting off the solid brass door hardware that clicks shut with reassuring certainty. A welcoming living room flows into a private dining

  Brian Caplicki Keller Williams Hudson Valley

  20 Columbia Ave, Middletown, NY 10940
• 

  $371,000 Sold Aug 19, 2025

  • 1,404 Sq Ft
  • $264/SF
  • 19 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1955

  16 Robertson Dr, Middletown, NY 10940

  Welcome to this charming ranch-style home, tucked away in the heart of Middletown, NY. This well-maintained home features 1,404 square feet of inviting space—perfect for first-time buyers, downsizers, or anyone looking for a cozy place to call home.Step inside and you’ll immediately notice the bright, open layout. The spacious living and dining areas flow together beautifully, creating

  Virginia Corbett eXp Realty

  16 Robertson Dr, Middletown, NY 10940
• 

  $302,500 Sold Aug 08, 2025

  • 1,560 Sq Ft
  • $194/SF
  • 12 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1957

  6 Randall Terrace, Middletown, NY 10940

  Welcome to one of Middletown’s most sought-after neighborhoods — Randall Terrace. With its solid structure and brand new plumbing and heating system, this home is ready for someone with vision to make it truly shine. A commuter’s dream — just minutes from major highways. Walking distance to SUNY Orange, restaurants, and shopping. Located in a quiet, well-established neighborhood. Exterior photos

  Rachel Hunt Realty Promotions Inc

  6 Randall Terrace, Middletown, NY 10940
• 

  $315,000 Sold Aug 08, 2025

  • 1,650 Sq Ft
  • $191/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1870

  57 Prince St, Middletown, NY 10940

  Beautiful oversized single-family with a three season porch. Three bed two bath with plenty of room. Close to schools, shopping and pharmacy within walking distance, large over sized back patio porch. Hardwood floors and high ceilings. Won’t last long. A/O !!!no more showings

  David Ferstand Daf Realty

  57 Prince St, Middletown, NY 10940
• 

  $400,000 Sold Aug 08, 2025

  • 1,044 Sq Ft
  • $383/SF
  • 39 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1951

  14 Mercer St, Middletown, NY 10940

  It Doesn't Get Better Than This!! Fully renovated and meticulously cared for Cape Cod with a first floor bedroom and full bathroom in one of the most sought after areas. If you know Mercer St you know it is a small cul de sac of well kept homes within walking distance to Maple Hill Park which offers a playgound, picnic area and a dog park! Step into the vestibule before entering the well

  Karen Taphorn Howard Hanna Rand Realty

  14 Mercer St, Middletown, NY 10940
• 

  $560,000 Sold Aug 08, 2025

  • 2,059 Sq Ft
  • $272/SF
  • 56 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1970

  11 Kennedy Terrace, Middletown, NY 10940

  Now available, a rare and immaculate colonial in Middletown’s highly sought after Presidential Heights neighborhood! This freshly updated house is loaded with amenities and features, including fully paid for 8+kW solar panel system and EV fast-charge battery 50amp outlet. It is situated on a quiet, peaceful street on top of a small hill with open views for miles. Featuring four large bedrooms

  Leeshai Lemish Panorama Realty

  11 Kennedy Terrace, Middletown, NY 10940
• 

  $430,000 Sold Aug 07, 2025

  • 1,338 Sq Ft
  • $321/SF
  • 37 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  11 Dogwood Dr, Middletown, NY 10940

  Well maintained 3 bedroom, 2 bath Bilevel in an established residential neighborhood. This attractive home features Stainless Steel appliances, a Master Bedroom suite and a 1 car garage. Sq. Footage does not include an additional 774 sq. Ft. unfinished lower level, which could be a Family Room, Bedroom, .5 bath, or use your imagination. All window treatments will stay. Conveniently located

  Gloria Allan John J Lease REALTORS Inc

  11 Dogwood Dr, Middletown, NY 10940
• 

  $372,690 Sold Aug 04, 2025

  • 1,560 Sq Ft
  • $239/SF
  • 45 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1875

  13 Wallkill Ave, Middletown, NY 10940

  Nestled in the heart of Middletown, New York, 13 Wallkill Avenue is a charming single-family home offering a blend of historic character and modern convenience. Built in 1875, this residence boasts 1,560 square feet of living space, featuring 3 bedrooms and 1.5 bathrooms. The property is situated on a 0.14-acre lot, providing a cozy outdoor space for relaxation and activities. Its prime location

  Elizabeth Muniz Howard Hanna Rand Realty

  13 Wallkill Ave, Middletown, NY 10940
• 

  $525,000 Sold Aug 01, 2025

  • 2,784 Sq Ft
  • $189/SF
  • 48 Days On Market

  • 6 Beds
  • 2 Baths
  • Built 1900

  26 Linden Ave Unit 24, Middletown, NY 10940

  For Sale: Spacious Side-by-Side Duplex in Prime Downtown Middletown LocationDon't miss this rare opportunity to own a true side-by-side duplex designed as a two-family home from the ground up. Each mirror-image unit offers 3 bedrooms and 1 full bath, making this the perfect investment property or live-in-and-rent option.Property Highlights:Identical units with private

  Jonathon Lee Keller Williams Hudson Valley

  26 Linden Ave Unit 24, Middletown, NY 10940
• 

  $515,000 Sold Jul 31, 2025

  • 2,242 Sq Ft
  • $230/SF
  • 65 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1985

  26 Davidge Rd, Middletown, NY 10940

  Spectacular Contemporary Home Located in Prestigious Presidential Heights in the City of Middletown. This Magnificent Home Features a Bright Airy, Sundrenched Floor plan. Gorgeous Marble Flooring, Large Sunken Living Room, Beautiful Sunken Family Room Custom 2 Sided Fireplace. Gourmet Kitchen with a designer Kitchen cabinetry, Stainless Steel Appliances, Subway tiled Backsplash , Recessed

  John Biasi Howard Hanna Rand Realty

  26 Davidge Rd, Middletown, NY 10940
• 

  $261,000 Sold Jul 29, 2025

  • 1,146 Sq Ft
  • $228/SF
  • 30 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2002

  67 Deer Court Dr, Middletown, NY 10940

  Bright, Beautiful & Move-In Ready – Second Floor 2BR/2BA Condo in Sought-After Deer Run!Welcome to the only one-level unit currently available in the highly desirable Deer Run community in Middletown! This spacious 2-bedroom, 2-bath condo is located on the second floor, offering privacy and peaceful living in a well-maintained complex. With large front-facing windows, the home is flooded

  Gail Rachlin Keller Williams Hudson Valley

  67 Deer Court Dr, Middletown, NY 10940
• 

  $159,900 Sold Jul 29, 2025

  • 735 Sq Ft
  • $218/SF
  • 181 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1989

  250 Concord Ln, Middletown, NY 10940

  Great location! Newly renovated

  Zhiheng Tang Keller Williams Hudson Valley

  250 Concord Ln, Middletown, NY 10940
• 

  

  /16

  $330,000 Sold Jul 28, 2025

  • 2,026 Sq Ft
  • $163/SF
  • 25 Days On Market

  • 7 Beds
  • 2.5 Baths
  • Built 1880

  31-33 Linden Ave, Middletown, NY 10940

  This property has so much to offer , 3 separate levels to customize . This unique property consists of : bonus rooms , in-law suites and main living quarters. The potential is endless the back yard has a court yard area ready to be re built . Ground floor basement . For owner occupants the option to apply for permits for tenant occupancy is available , which allows for a multi family benefit .

  Karen Smith Anderson 1st Kander Realty Inc

  31-33 Linden Ave, Middletown, NY 10940
• 

  $294,000 Sold Jul 28, 2025

  • 1,464 Sq Ft
  • $201/SF
  • 102 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1951

  303 Wawayanda Ave, Middletown, NY 10940

  Enjoy Living at its Best in this beautiful Home in a desirable location of Middletown. This wonderful home features an Inviting Living room with a Bay window, Formal Dining rm, Kitchen with Breakfast Bar, updated tiled Bathroom, large First Floor Primary Bedroom, Family room with Vaulted ceilings, office/ Den could be a 4 th Bedroom. Second level features 2 Spacious Bedrooms. Full

  John Biasi Howard Hanna Rand Realty

  303 Wawayanda Ave, Middletown, NY 10940
• 

  $301,000 Sold Jul 25, 2025

  • 1,040 Sq Ft
  • $289/SF
  • 33 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1900

  56 Beattie Ave, Middletown, NY 10940

  Introducing a charming and recently renovated home, completed in 2023, offering modern comfort and style. This inviting residence features three spacious bedrooms and one and a half baths. The heart of the home is a stunning, modern kitchen equipped with sleek granite countertops, perfect for culinary enthusiasts. Adjacent to the kitchen is a formal dining area, ideal for hosting gatherings and

  Maria Sairrino Cronin & Company Real Estate

  56 Beattie Ave, Middletown, NY 10940
• 

  $425,000 Sold Jul 24, 2025

  • 1,316 Sq Ft
  • $323/SF
  • 27 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1956

  22 Willow Place, Middletown, NY 10940

  There’s something special about 22 Willow Place! This beautifully updated 3-bedroom split-level is turn-key and full of thoughtful upgrades that make living easy. With every major upgrade already complete, this home is truly turn-key and move-in ready. The heart of the home is the renovated kitchen, featuring upgraded appliances, modern finishes, and a stunning skylight that fills the space

  Patricia Sassi RE/MAX Benchmark Realty Group

  22 Willow Place, Middletown, NY 10940
• 

  $315,000 Sold Jul 23, 2025

  • 1,631 Sq Ft
  • $193/SF
  • 28 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  42 Wisner Ave, Middletown, NY 10940

  A charming 3-bedroom, 2-bathroom home situated on a spacious corner lot in the heart of Middletown. This well-maintained property offers solid bones and endless potential for your personal touch. The first floor features a flexible layout, including a cozy den that could easily serve as a 4th bedroom, home office, or guest space. Ample natural light, and a traditional floor plan create a warm and

  Kismet Johnson eXp Realty

  42 Wisner Ave, Middletown, NY 10940
• 

  $275,000 Sold Jul 23, 2025

  • 1,201 Sq Ft
  • $229/SF
  • 205 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  122 Cottage St, Middletown, NY 10940

  Your First Single-Family Home—Where Independence Begins | Middletown, NYThere’s a moment when you realize: it’s time to stop paying someone else’s mortgage and start building something of your own. This 2-bedroom, 1-bath single-family home in Middletown, NY is that moment in the making—a chance to own land, space, and freedom, with no shared walls or noisy neighbors above or below you.

  Brian Caplicki Keller Williams Hudson Valley

  122 Cottage St, Middletown, NY 10940
• 

  $385,000 Sold Jul 22, 2025

  • 41 Days On Market

  • 2 Baths
  • Built 1888

  289 North St, Middletown, NY 10940

  Discover this delightful colonial duplex situated in the city of Middletown! This well-maintained property features two spacious units, each offering two comfortable bedrooms, a full bathroom, and a versatile bonus room that can be utilized as a den or office space, perfect for today's remote working environment. Recently painted and updated baths, this 2-family home offers plenty of parking for

  Patricia Sassi RE/MAX Benchmark Realty Group

  289 North St, Middletown, NY 10940
• 

  

  /50

  $595,000 Sold Jul 21, 2025

  • 3,890 Sq Ft
  • $153/SF
  • 2 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1948

  1 Wawayanda Place, Middletown, NY 10940

  Discover this charming, recently renovated 5-bed, 3-bath home in Orange County, NY, boasting over 3,000 sq. ft. It offers resort-like amenities, perfect for short-term rentals. Explore nearby attractions like West Point, Storm King Art Center, Legoland New York, and Woodbury Common Premium Outlets. Showings by appointment only, Tuesdays to Thursdays, with pre-approval/proof of funds.

  Jamie Sittner Find Advisors

  1 Wawayanda Place, Middletown, NY 10940

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