Middletown, NY Homes for Sale under $400,000

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  /29

  $359,900

  Open Sat 11AM - 1PM

  • 2 Beds
  • 1.5 Baths
  • 1,322 Sq Ft

  7 Rowan St, Middletown, NY 10940

  Here is the rare first home that costs almost nothing to worry about. It has been remodeled through and through, so the bills that scare new owners are already behind you. The kitchen is brand new. The bathroom is brand new. The roof is only 8 years young, the siding is new, the windows are new, and even the water service line has been replaced. Natural gas heat keeps the coldest stretch of

  

  Brian Caplicki

  KW Hudson Valley United

  7 Rowan St, Middletown, NY 10940
• Explore Middletown

• 

  

  

  /30

  $329,900

  • 2 Beds
  • 1.5 Baths
  • 1,008 Sq Ft

  89 Prince St, Middletown, NY 10940

  There is a particular kind of quiet that arrives when a place becomes yours. The last box is finally down, the door clicks shut behind you, and it lands softly that this is the address you give people now. This is the home where that feeling begins, and where it stays. It is ready for you from the first day. Everything lives on one easy level, open and unhurried, morning light moving through the

  

  Brian Caplicki

  KW Hudson Valley United

  89 Prince St, Middletown, NY 10940
• 

  

  

  /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
• 

  

  

  /9

  $399,900

  Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,799 Sq Ft

  12 Todd Dr, Middletown, NY 10941

  Conveniently located in Pine Bush schools and close to ammenities is the 3 bedroom two bath split level on a cul-de-sac

  

  Lynelle Alessi

  KW Hudson Valley United

  12 Todd Dr, Middletown, NY 10941
• 

  

  /2

  $155,000

  $20K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 784 Sq Ft

  45 Knapp Ave, Middletown, NY 10940

  Attention investors! This is a true “what you see is what you get” opportunity. Bring your tools and imagination and transform this property into a valuable addition to your rental portfolio. Perfect for investors seeking potential and long-term returns. Cash buyer or rehab loan needed.

  

  Dulce M Ferrera

  KW Hudson Valley United

  45 Knapp Ave, Middletown, NY 10940
• 

  

  /33

  $395,000

  • 4 Beds
  • 2 Baths
  • 1,428 Sq Ft

  24 Mountain Ave, Middletown, NY 10940

  Cape Cod with 4 bedrooms, 2 baths, garage and large deck overlooking peaceful and private backyard. Deck less than 2 years old, beautiful stainless steel appliances only 2 years old. 2nd floor is not like your typical cape cod. Very spacious with a great bonus area. Conveniently located in Middletown School District just 3 miles from the train station and just minutes from park, walking trails,

  

  Sharon Reynolds

  KW Hudson Valley United

  24 Mountain Ave, Middletown, NY 10940
• 

  

  /13

  $239,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  16 Woodland Rd, Middletown, NY 10940

  Welcome home to this very nice three bedroom seasonal ranch located in the Minisink Valley School District in a quiet neighborhood! This private property is surrounded by nature with a large open yard to play and have fun in the sun. The large deck overlooks the private back yard and surrounding woods. The roof has been recently replaced. Sale includes an additional lot of 0.11 acres to bring the

  

  Joseph Paoli

  Howard Hanna Rand Realty

  16 Woodland Rd, Middletown, NY 10940
• 

  

  /20

  $245,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  100 Hillside Dr Unit C6, Middletown, NY 10941

  Prime Location in Sought-After Hillside Village in the Goshen School District!Welcome to this first-floor, end-unit, 2-bedroom condo located in the desirable gated community of Hillside Village. This home offers one-level accessible living layout featuring a galley kitchen and a spacious living room with sliding glass doors leading to a private patio. The former dining area has been

  

  Kathy White

  Exit Realty Connections

  100 Hillside Dr Unit C6, Middletown, NY 10941
• 

  

  /41

  $375,000

  $20K PRICE INCREASE

  • 3 Beds
  • 1.5 Baths
  • 1,470 Sq Ft

  4 Eaton Ct, Middletown, NY 10940

  Welcome to Canterbury Knolls! This beautifully maintained 3-bedroom, 1.5-bathroom home is move-in ready and filled with charm. Updates include a brand new roof. Some rooms and garage have been freshly painted. Step inside to find gleaming hardwood floors throughout, complemented by porcelain tiles in the entryway and kitchen. The Homeowner's Association makes life easier by handling all exterior

  

  Dulce M Ferrera

  KW Hudson Valley United

  4 Eaton Ct, Middletown, NY 10940
• 

  

  /21

  $119,000

  • Land
  • 4.27 Acres
  • $27,869 per Acre

  0 Hog Mountain Cir, Middletown, NY 12430

  This is the property with a view you have been looking for. 4.27 acres of cleared, ready to build land in the Catskill Mountains just two hours from the George Washington Bridge. Whether it is a weekend retreat you have in mind or a forever home, the view is unmatched and will bring you the peace and serenity the Catskills have to offer. This property is only 10 minutes from Belleayre Ski

  

  Terence Lynch

  Century 21 New West Properties

  0 Hog Mountain Cir, Middletown, NY 12430
• 

  

  /28

  $299,900

  • 2 Beds
  • 1 Bath
  • 1,010 Sq Ft

  32 W Conkling Ave, Middletown, NY 10940

  Some houses greet you at the door. This one wraps around you the moment you walk in. Step through the light-filled sunroom, all glass and morning sun, and into a main floor paneled in warm honey pine that has been cared for across a hundred years and wears every one of them beautifully. You notice the beamed ceilings, the way the afternoon light pools on the wood, the rooms that flow one into the

  

  Brian Caplicki

  KW Hudson Valley United

  32 W Conkling Ave, Middletown, NY 10940
• 

  

  /43

  $399,900

  Open Sat 1PM - 3PM $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
• 

  

  /30

  $399,900

  • 3 Beds
  • 2.5 Baths
  • 1,593 Sq Ft

  568 County Route 49 Unit 2C, Middletown, NY 10940

  Privately set in a quiet and intimate four-unit HOA community, this bright and welcoming home offers comfort, space, and convenience throughout. An open foyer leads into the updated kitchen featuring Quartz/Quartzite countertops, crisp white cabinetry, and ample storage. Natural light pours into the spacious dining and living areas, highlighted by beautiful flooring and a large closet ideal for

  

  Hazel Cello

  KW Hudson Valley United

  568 County Route 49 Unit 2C, 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
• 

  

  /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
• 

  

  /19

  $315,000

  $10K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  66 Patio Rd, Middletown, NY 10941

  This beautifully maintained 3-bedroom, 1.5-bath townhouse-style single-family home is move-in ready and available for immediate occupancy. The home features stainless steel appliances and a combination of ceramic tile, laminate, and hardwood flooring throughout, creating an attractive, low-maintenance, and allergy-friendly living environment. Both bathrooms have been tastefully updated, and a

  Jill Wilkins KW Hudson Valley United

  66 Patio Rd, Middletown, NY 10941
• 

  

  /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
• 

  

  /44

  $384,999

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

  1 Lake Ridge Dr, Middletown, NY 10940

  Seller will pay $5,000 of your closing costs! Set within the highly desirable Lake Ridge at Water’s Edge community in Middletown, this beautifully cared-for end-unit townhouse combines comfort, style, and low-maintenance living. Offering 2 bedrooms and 1.5 baths, the home features tasteful upgrades throughout, including luxury vinyl flooring, recessed LED lighting, and a warm, inviting gas

  Colin Seitz RE/MAX Benchmark Realty Group

  1 Lake Ridge Dr, Middletown, NY 10940
• 

  

  /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 has

  Zhiheng Tang KW Hudson Valley United

  6 Charlotte Mews, Middletown, NY 10940
• 

  

  /17

  $333,000

  $4K PRICE DROP

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

  5 Kendal Ln, Middletown, NY 10940

  Modern Comfort & Lake Access – The Best of Waters Edge! Welcome to this beautifully maintained 2-bedroom, 2.5-bath condo in the highly desirable Waters Edge community. Offering the perfect blend of peaceful lakeside living and modern convenience, this home features a bright, open floor plan designed for easy living. Most of the windows have been replaced, enhancing energy efficiency and bringing

  Jonathon Lee KW Hudson Valley United

  5 Kendal Ln, Middletown, NY 10940
• 

  

  /15

  $259,999

  • 4 Beds
  • 1 Bath
  • 1,140 Sq Ft

  29 Parsons Ln, Middletown, NY 10940

  Endless Potential - Discover the possibilities at 29 Parsons Lane — a private country property offering space, privacy, and opportunity on approximately 6.4 acres. Offering an additional 4.6 acres for a total of 11 acres. This single-family ranch-style home features 4 bedrooms (currently lives as a 2 bedroom & a laundry room), 1 full bathroom, and approximately 1,140 square feet of living space.

  Camelia Pena-Rivera RE/MAX Distinguished Hms.&Prop

  29 Parsons Ln, Middletown, NY 10940
• 

  

  /19

  $159,900

  $12K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  509 5th Ave, Middletown, NY 10941

  Want to buy an almost new home for $169900? That’s right, ONLY THREE YEARS OLD!! This home needs to be seen to be believed. Two large bedrooms with large closets. Huge open floorplan living room and dining room with lots of windows for natural light. Large deck for relaxing and entertaining. So many cabinets and a ton of counter space with stainless steel appliances. Full main bathroom with a tub

  John Nahass Century 21 Full Service Realty

  509 5th Ave, Middletown, NY 10941
• 

  

  /33

  $259,000

  • 2 Beds
  • 1.5 Baths
  • 1,230 Sq Ft

  129 Concord Ln Unit 129, Middletown, NY 10940

  An exceptional opportunity for homeowners and savvy investors, this sun-drenched, southeast-facing condo is located in one of Middletown’s rare communities with NO rental restrictions. Experience the comfort of two-level living with a thoughtful layout featuring a spacious living room on the main floor and private bedrooms upstairs. This home offers ultimate peace of mind with a Boiler and Water

  Hai Li KW Hudson Valley United

  129 Concord Ln Unit 129, Middletown, NY 10940
• 

  

  /18

  $189,000

  New Construction

  • 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
• 

  

  /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
• 

  

  /23

  $134,999

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  79 Stern Scenic Dr, Middletown, NY 10940

  Welcome to this updated 3-bedroom, 2-bath double-wide mobile home offering comfort, space, and convenience in Middletown. Recent updates enhance both style and functionality, while the open and spacious layout provides plenty of room to relax or entertain. The primary bedroom features a private bath, and the additional bedrooms are generously sized. Conveniently located near local shopping,

  Ivan Carvalho Exit Realty Connections

  79 Stern Scenic Dr, Middletown, NY 10940
• 

  

  /36

  $379,000

  • 4 Beds
  • 2 Baths
  • 1,770 Sq Ft

  26 1/2 Ridge St, Middletown, NY 10940

  Beautifully renovated single-family home offering a clean, comfortable layout with thoughtful updates throughout. This residence features 4 spacious bedrooms filled with natural light and a brand-new kitchen equipped with appliances and ample cabinetry. Fresh finishes throughout the home create a bright, move-in-ready feel. Enjoy additional storage space in both the attic and basement, providing

  Cheskel Werzberger Mount Realty

  26 1/2 Ridge St, Middletown, NY 10940
• 

  

  /9

  $399,900

  • 4 Beds
  • 2 Baths
  • 1,472 Sq Ft

  25 Mill St, Middletown, NY 10940

  Completely renovated two-unit property with Residential/CMU zoning. Ideal opportunity for an owner-user or investor — operate your business on the first floor while generating rental income from the occupied second-floor unit. Property includes 2 car parking/off-street parking, with potential for expansion subject to city approvals.

  Sammy Zambrano Keller Williams Realty

  25 Mill St, Middletown, NY 10940
• 

  

  /26

  $199,000

  $51K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 360 Sq Ft

  51 S Shore Dr, Middletown, NY 10940

  Welcome to 51 S Shore Drive, a charming and thoughtfully updated bungalow retreat nestled on a private, wooded 9,374 sq ft lot with sparkling lake views in scenic Middletown, NY. This beautifully curated 1-bedroom, 1-bath lakefront getaway offers 360 square feet of smart, stylish living space perfect for a weekend escape, vacation rental, or year-round peaceful living. Step inside to a crisp,

  Arya Rabinovits eRealty Advisors, Inc

  51 S Shore Dr, Middletown, NY 10940
• 

  

  /27

  $185,000

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  326 Concord Ln, Middletown, NY 10940

  PRICED TO SELL!!! Buttonwood Hills Condominiums now offers a 2 bedroom/2 bath unit for your purchase. Add your final touches and make it yours! A ground level end unit with open floor plan from living room to dining room with sliders that lead to a seating area where you can enjoy the outdoors. Beautiful kitchen with stainless steel appliances & plenty of cabinet space. Spacious bedrooms, one

  Sandra Arnez KW Hudson Valley United

  326 Concord Ln, Middletown, NY 10940
• 

  

  /9

  $285,000

  • 3 Beds
  • 1.5 Baths
  • 1,188 Sq Ft

  18 Black Stallion Ct, Middletown, NY 10940

  Welcome home! This inviting 3-bedroom, 1.5-bath townhome offers comfort, space and a welcoming layout. Owned by the same family for over 50 years, this home is now ready for its next chapter. Inside, you’ll find a large, comfortable living room that’s perfect for gathering and relaxing. The eat-in kitchen has been updated with new flooring and appliances, making it both functional and stylish.

  Jennifer Kubler eRealty Advisors, Inc

  18 Black Stallion Ct, Middletown, NY 10940
• 

  

  /13

  $275,000

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

  11 Jordan Ln, Middletown, NY 10940

  Welcome to 11 Jordan Lane, Middletown, NY. This 2-bedroom, 2-bathroom condo offers a practical floor plan and a convenient location close to shopping, dining, schools, healthcare facilities, and major commuter routes.With strong potential and a desirable location, the property presents an excellent opportunity for investors seeking immediate rental income or buyers looking to add value

  Richu Saj Kerala Realty, LLC

  11 Jordan Ln, Middletown, NY 10940
• 

  

  /22

  $399,000

  $26K PRICE DROP

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

  19 Putters Way Unit 9, Middletown, NY 10940

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

  Abraham Lefkowitz Access Realty Team Inc

  19 Putters Way Unit 9, Middletown, NY 10940
• 

  

  /23

  $399,999

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

  341 Highland Ave Extension, Middletown, NY 10940

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

  Valerie Jewis Keller Williams Realty

  341 Highland Ave Extension, Middletown, NY 10940
• 

  

  /50

  $310,000

  • 3 Beds
  • 1.5 Baths
  • 1,398 Sq Ft

  4 Lincoln St, Middletown, NY 10940

  This 3-bedroom, 2-bath Colonial offers 1,398 square feet of comfortable living space on a 0.11-acre lot. Built in 1890, the home blends timeless style with thoughtful upgrades while keeping its original charm. Enjoy bright mornings with natural light, cozy evenings at home, and a neighborhood close to shopping, restaurants, parks, schools, and local services. All utilities are available, making

  Matthew Gibbs KW Hudson Valley United

  4 Lincoln St, Middletown, NY 10940
• 

  

  /22

  $318,000

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

  9 Jordan Ln, Middletown, NY 10940

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

  Bonnie Natt Realty Promotions Inc

  9 Jordan Ln, Middletown, NY 10940
• 

  

  /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
• 

  

  /23

  $309,000

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

  181 Deer Ct Dr, Middletown, NY 10940

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

  Beverly Huaman Howard Hanna Rand Realty

  181 Deer Ct Dr, Middletown, NY 10940
• 

  

  /44

  $355,000

  • 3 Beds
  • 1 Bath
  • 1,830 Sq Ft

  122 Castle High Rd, Middletown, NY 10940

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

  Denise Clancy Curasi Realty, Inc.

  122 Castle High Rd, Middletown, NY 10940
• 

  

  /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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