Homes for Sale near Middletown High School

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  /24

  $563,000

  $36K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,392 Sq Ft

  5 Oak Ridge Rd, Middletown, NY 10940

  Built in 2020, this spacious 2,392 sq ft home offers 4 bedrooms, 3 full bathrooms, and a 2-car garage. The upper level boasts an open-concept layout with vaulted ceilings, a modern kitchen featuring granite countertops and stainless steel appliances, a bright living room, and three bedrooms, including the primary suite, and two full baths. The finished lower level adds even more living space with

  Luke Joachim Redfin Real Estate

  5 Oak Ridge Rd, 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
• 

  

  

  /37

  $289,900

  • 2 Beds
  • 2 Baths
  • 1,049 Sq Ft

  141 Ruth Ct, Middletown, NY 10940

  Welcome to 141 Ruth Court! This move-in-ready two-bedroom, two-full-bath home has been freshly painted and features new carpeting throughout, offering a clean and inviting space that’s ready for you to make your own. With a comfortable layout, two bedrooms, and two full baths, this home is a wonderful opportunity for easy, turnkey living. Cathedral ceilings, 2 floors, open floor plan offering

  Dawn Gregg Curasi Realty, Inc.

  141 Ruth Ct, Middletown, NY 10940
• 

  

  

  /31

  $339,000

  • 2 Beds
  • 1 Bath
  • 992 Sq Ft

  26 Gardner Ave, Middletown, NY 10940

  A cozy and beautifully maintained home in a convenient location, this charming 2-bedroom, 1-bath property offers comfort, character, and thoughtful updates throughout. The updated kitchen and bathroom complement the warm hardwood floors on the main level, while raised dormers upstairs create a more spacious feel.The home features numerous important updates, including the roof, heating and

  Julie Kim Howard Hanna Rand Realty

  26 Gardner Ave, Middletown, NY 10940
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  /46

  $489,999

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

  93 Meadow View Dr, Middletown, NY 10940

  This beautiful 3 bed 3 1/2 bath townhome is nestled in the heart of Middletown with so much to offer and just minutes to transportation to and from NYC. Upon entering you'll find beautiful hardwood floors throughout the first floor. An open floor plan including a sun drenched living room with a fireplace, full glass door leading to a very spacious deck for outdoor grilling or relaxation. Just

  Kevin Grier KW Hudson Valley United

  93 Meadow View Dr, Middletown, NY 10940
• 

  

  /11

  $349,000

  $40K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,416 Sq Ft

  4 Harding St, Middletown, NY 10940

  Middletown Central Gem - Space, Character & Low Taxes!Minutes from Downtown Middletown, this solid 4-bedroom, 2-bath home offers the generous room proportions and practical layout characteristic of an older home, along with a large attic and full basement providing exceptional storage and future potential. A brand-new high-efficiency Navien tankless combination boiler adds modern

  Hai Li KW Hudson Valley United

  4 Harding St, Middletown, NY 10940
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  /50

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 2,548 Sq Ft

  8 Green Ct, Middletown, NY 10940

  Welcome to this well-maintained 3-level townhome in The Fairways, a gated community conveniently located next to a golf course and just minutes from major highways, Garnet Health Medical Center, shopping, restaurants, and everyday conveniences. This home offers a 2-car garage, a finished lower level with direct garage access, and a functional floor plan designed for comfortable everyday living.

  Jie Liu KW Hudson Valley United

  8 Green Ct, Middletown, NY 10940
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  /9

  $275,000

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

  18 Black Stallion Ct, Middletown, NY 10940

  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. New carpeting

  Jennifer Kubler eRealty Advisors, Inc

  18 Black Stallion Ct, Middletown, NY 10940
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  /21

  $455,000

  • 4 Beds
  • 2 Baths
  • 1,466 Sq Ft

  225 Monhagen Ave, Middletown, NY 10940

  Great Location with C-2 Mixed-Use Zoning Potential! Located at 225 Monhagen Avenue in Middletown, this nicely maintained property offers a comfortable and practical layout along with exceptional flexibility for homeowners, investors, and business-minded buyers. The home features 4 bedrooms and 2 full bathrooms, providing generous space for comfortable family living. A finished basement adds

  Jin Pang Panorama Realty

  225 Monhagen Ave, Middletown, NY 10940
• 

  

  /41

  $699,000

  $130K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,340 Sq Ft

  571 Route 17m, Middletown, NY 10940

  Steeped in character and timeless appeal, this 1930 Colonial invites you in with its striking stone facade and a graceful partial wrap-around porch—an ideal spot to enjoy quiet mornings or unwind at the end of the day. Inside, the home blends classic craftsmanship with modern comfort, featuring rich wooden floors that flow seamlessly throughout the main level.The first floor offers a warm and

  Angela Murphy BHG Real Estate Green Team

  571 Route 17m, Middletown, NY 10940
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  /25

  $478,000

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

  25 Independence Ave, Middletown, NY 10940

  It is located in one of Middletown's most desirable neighborhoods, where strong demand and steadily increasing home values make this an exceptional opportunity!This beautifully renovated, move-in-ready 4-bedroom home has been thoughtfully updated from top to bottom. The brand-new kitchen features modern cabinetry, a new stove, and an added pantry/storage closet, creating a stylish and

  Jin Pang Panorama Realty

  25 Independence Ave, Middletown, NY 10940
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  /14

  $375,000

  $18K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  1 Chestnut St, Middletown, NY 10940

  Beautifully renovated 3 bedroom 1 bathroom, everything is brand new, electrical, plumbing and heating, plus with a big corner lot. Plenty of space, beautiful kitchen - come see it today.

  Safdar Mursalin eXp Realty

  1 Chestnut St, Middletown, NY 10940
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  /3

  $100,000

  • Land
  • 1.4 Acres
  • $71,429 per Acre

  0 Sunrise Park Rd Unit ONEH6269318, Wawayanda, NY 10958

  No engineering done on this lot. Quiet cul de sac near everything. Additional Information: SoilType:Unknown,

  Joe Distelburger Keller Williams Realty

  0 Sunrise Park Rd Unit ONEH6269318, Wawayanda, NY 10958
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  /22

  $395,000

  $55K PRICE DROP

  • 1,450 Sq Ft

  13 Benton Ave, Middletown, NY 10940

  Beautiful Brick Mixed Use Building located in a very desirable area of Middletown. This wonderful building features 3 Units. First unit is Office SpaceThat is great for an accountant, attorney,Real Estate office. Etc. Second Level offers a Spacious 1 Bedroom apartment 3 rd level offers another large 1 bedroom Apartment. Separate Electric and Hot water heaters. Large Parking Lot Second

  John Biasi Howard Hanna Rand Realty

  13 Benton Ave, Middletown, NY 10940
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  /24

  $299,999

  • 2 Beds
  • 1 Bath
  • 1,164 Sq Ft

  14 Airport Rd, Middletown, NY 10940

  14 Airport Road is ready for a little love and its next chapter. Located in the Town of Wallkill, this home offers a surprisingly spacious and flexible layout with plenty to work with for a buyer ready to roll up their sleeves and make it their own.The main level offers an open flow between the kitchen and living areas, with a brick fireplace adding character to the space. The kitchen is

  Cindy-Lee Dorcely KW Hudson Valley United

  14 Airport Rd, Middletown, NY 10940
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  /6

  $799,000

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

  76 Winters Ln, Middletown, NY 10940

  Welcome to your dream home! This stunning new construction craftsman-style home is now being built on Lot 1 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

  76 Winters Ln, Middletown, NY 10940
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  /24

  $555,000

  $24K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,202 Sq Ft

  29 Murray Rd, Middletown, NY 10940

  3 PRIVATE ACRES + ULTIMATE VERSATILITY + POSSIBLE INCOME POTENTIAL = A RARE MIDDLETOWN OPPORTUNITY Set on 3 serene, wooded acres, this beautifully maintained raised ranch offers an expansive 2,202 sq. ft. of living space designed with a unique, highly adaptable layout that can help with your financial goals or adapt to your lifestyle. The main level features a bright open-concept main floor with

  Regina Lombardo KW Hudson Valley United

  29 Murray Rd, Middletown, NY 10940
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  /16

  $329,000

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

  15 N Aspen Rd, Middletown, NY 10940

  NO HOA FEES! LOW TAXES!! Welcome to easy, effortless living in this turnkey, move-in ready 2-bedroom home, thoughtfully updated with modern finishes and designed for today’s lifestyle. From the moment you step inside, you’re greeted by a bright and inviting interior that feels both stylish and comfortable. The updated kitchen shines with sleek countertops, crisp cabinetry, and modern appliances,

  Carmela Lopez Borrazas Serhant LLC

  15 N Aspen Rd, Middletown, NY 10940
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  /28

  $359,000

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  21 Keystone Park, Middletown, NY 10940

  What you've been waiting for! Adorable and affordable 3 BR ranch on a cul de sac with lovely, private back yard! Large LR! Kitchen opens to Dining area! New walk in shower in bath! Full basement and 1 car garage. C/A! HW floors! Newer windows! Municipal services! Convenient to shopping and Route 17 for commuter!

  Linda Clark Hudson Valley Griffith

  21 Keystone Park, Middletown, NY 10940
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  /40

  $354,900

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  41 Roosevelt Ave Unit 39, Middletown, NY 10940

  Welcome home to this beautifully maintained 3-bedroom, 1-bath Colonial in the City of Middletown. Conveniently located near shopping, restaurants, parks, schools, and major commuter routes, this home blends classic charm with practical everyday living. From the moment you arrive, you'll be drawn to the expansive wraparound front porch—the perfect place to enjoy your morning coffee or unwind at

  Patricia Sassi RE/MAX Benchmark Realty Group

  41 Roosevelt Ave Unit 39, Middletown, NY 10940
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  /29

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  30 Chestnut Ave, Middletown, NY 10940

  Tucked into one of Middletown's established neighborhoods, 30 Chestnut Avenue is a home that effortlessly blends comfort, style, and convenience. From the moment you step inside, you'll appreciate the bright, open floor plan where natural light pours through the windows, creating inviting spaces designed for both everyday living and memorable gatherings.The heart of the home is the

  Lauren Iacono Corcoran Baer & McIntosh

  30 Chestnut Ave, Middletown, NY 10940
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  /28

  $549,900

  82 Montgomery St Unit 84, Middletown, NY 10940

  Turn-of-the-century solid brick two-family home situated on a desirable corner lot comprising two lots. This owner-occupied property offers a spacious yard with established grapevines and mature fruit trees, creating a wonderful setting for outdoor enjoyment.An excellent opportunity for an owner-occupant looking for a home with rental income potential. The main-floor unit features 2

  Jonathon Lee KW Hudson Valley United

  82 Montgomery St Unit 84, Middletown, NY 10940
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  /42

  $430,000

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  11 Columbia Ave, Middletown, NY 10940

  BEAUTIFULLY maintain old style home in the heart of Middletown with low PROPERTY taxes. A must-see home to appreciate it quality and charm. Located near Davidge Park. Commuter Friendly location easy access to Route 17 and interstate highway 84 to Penn and Conn. NJ Transit and a 15 min walk to the Shortline Bus to Midtown Manhattan with Plenty of Parking should you choose to drive to the bus

  Norberto Tirado N Tirado Realty LLC

  11 Columbia Ave, Middletown, NY 10940
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  /28

  $399,999

  Pre-Foreclosure

  • 3 Beds
  • 2.5 Baths
  • 1,540 Sq Ft

  70 Peach Place, Middletown, NY 10940

  Welcome to 70 Peach Place, a beautifully maintained townhouse nestled in the desirable Peach Hills subdivision. This spacious home offers the perfect blend of comfort, convenience, and value with no HOA fees and low taxes.Step inside to discover newly updated bathrooms, new appliances, and a brand-new hot water heater, providing peace of mind for years to come. The generous primary suite

  Virginia Corbett eXp Realty

  70 Peach Place, Middletown, NY 10940
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  /20

  $146,900

  $5K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft

  394 Concord Ln, Middletown, NY 10940

  A fantastic opportunity for first time home buyers, downsizers or investors. Step into this freshly painted, well maintained 1 bedroom condo and experience easy living, low maintenance and community perks including pool and clubhouse. Stainless steel stove and dishwasher are only 3 years old, heating unit 7-8 years old. This complex is conveniently located near major highways and shopping. Enjoy

  Carol Scully Keller Williams Realty

  394 Concord Ln, Middletown, NY 10940
• 

  /2

  $283,000

  $70K PRICE DROP

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

  187 Watkins Ave, Middletown, NY 10940

  Opportunity knocks in New York. Located near Sprucegate Farm, Swim King, and Magnanini Winery. This home has approx. 1,545 sq. ft. and a lot of approx. 7,750 sq. ft. A great investment opportunity. Buyers check with City, County, Zoning, Tax, and other records to their satisfaction. AS-IS SALE property.

  Neven Spralja Realhome Services and Solutions Inc

  187 Watkins Ave, Middletown, NY 10940
• 

  

  /23

  $490,000

  • 3 Beds
  • 2.5 Baths
  • 2,191 Sq Ft

  19 Magnolia Park Rd, Middletown, NY 10940

  BACK ON MARKET: Welcome to this beautifully maintained newer-construction home in the sought-after Magnolia Park section of the Maple Fields community in Middletown. Built in 2019–2020, this spacious residence offers approximately 2,100 square feet of modern living with an open-concept layout designed for today’s lifestyle. The main level features a bright and airy living space, a stylish kitchen

  Daniel Amodeo AMO Realty

  19 Magnolia Park Rd, Middletown, NY 10940
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  /33

  $730,000

  • 4 Beds
  • 3 Baths
  • 2,646 Sq Ft

  130 Apple Lane Dr, Middletown, NY 10940

  Mid-century modern haven: Shapes inspired by Frank Lloyd Wright and his organic architectural style. Enjoy one level living with an indoor–outdoor flow that connects the home seamlessly to nature. Clean lines and expansive windows throughout. Sprawling across 8 acres, this property offers endless possibilities for a lively household — space for a swimming pool, tennis court, or other recreational

  Kichka Pascaru Douglas Elliman Real Estate

  130 Apple Lane Dr, Middletown, NY 10940
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  /15

  $329,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  195 Commonwealth Ave, Middletown, NY 10940

  Welcome to 195 Commonwealth Ave, where small-town charm meets everyday convenience. Nestled in the heart of Middletown, this 3-bedroom, 1-bath Cape Cod puts you minutes from the Metro-North train, shops, dining, and everything the Hudson Valley has to offer — with a backyard that feels like your own private retreat.Inside, gleaming hardwood floors flow throughout, anchored by a kitchen

  Loretta Wolff NexLvl Real Estate Inc.

  195 Commonwealth Ave, Middletown, NY 10940
• 

  

  /19

  $379,999

  • 2 Beds
  • 2 Baths
  • 1,252 Sq Ft

  8 Forest Ave Unit 6, Middletown, NY 10940

  Welcome to 8 Forest Ave, Middletown, NY 10940—a charming corner-lot home offering comfort, flexibility, and plenty of outdoor space.This well-maintained property features 2 spacious bedrooms plus a bright sunroom that can easily be converted into a third bedroom, home office, or guest room. The home also offers 2 full bathrooms, a generously sized kitchen, and a separate dining room,

  Mariama Balde Reliable Realty Group

  8 Forest Ave Unit 6, Middletown, NY 10940
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  /11

  $449,000

  • 4 Beds
  • 1,805 Sq Ft

  94 Linden Ave, Middletown, NY 10940

  Incredible opportunity to live in 1 unit and enjoy the additional income! Or an Investor. Both units features a Brand New Kitchen. Stainless Steal Appliances, Quartz countertops, eat-In-kitchen vinyl plank floors. 4 Bedrooms & 2 full bathrooms in total. Walk-out basement, laundry and storage. Separate utilities. HVAC, Siding and Roof 2023. Fenced in yard. The home is in close proximity to parks,

  Kevin Grier KW Hudson Valley United

  94 Linden Ave, Middletown, NY 10940
• 

  

  /25

  $289,000

  • 2 Beds
  • 2 Baths
  • 1,110 Sq Ft

  63 Sycamore Dr, Middletown, NY 10940

  Welcome to the beautifully maintained Clemson Park complex. Upon entry you'll walk into the spacious, well-lit Living Room. This home also features a Formal Dining Room and Eat In Kitchen. You'll be able to access the balcony through the sliding glass doors in the living room to kick-back and relax on the deck. The Primary Bedroom offers his/her closets as well as a Primary Bathroom with an

  Kyle Pierce Patricia Schiller Real Est Co.

  63 Sycamore Dr, Middletown, NY 10940
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  /50

  $519,000

  $1K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,567 Sq Ft

  29 Avoncroft Ln, Middletown, NY 10940

  Welcome to 29 Avon Croft Lane, One of a Kind Nestled among mature trees and natural surroundings, this property provides a peaceful and secluded setting. a beautifully maintained home offering privacy, comfort, and convenience in a desirable Middletown location. . This spacious home offers the comfort and freedom you’ve been looking for—about 70 miles from NYC, with easy access to major highways

  Gail Rachlin KW Hudson Valley United

  29 Avoncroft Ln, Middletown, NY 10940
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  /18

  $350,000

  $100K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,478 Sq Ft

  47 Wickham Ave Unit 45, Middletown, NY 10940

  Rare Opportunity to Live and Work under the same roof. Save money and time in buying this beautiful 1800’s Colonial Home in a very sought after area of Middletown. This Timeless Elegant home features Gorgeous wide Plank Flooring, beautiful Staircase and Rocking Chair Porches. This Charming home is Great for a professional I.E Accountant, Attorney, Real Estate Professional ETC This wonderful home

  John Biasi Howard Hanna Rand Realty

  47 Wickham Ave Unit 45, Middletown, NY 10940
• 

  

  /31

  $278,000

  $12K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,146 Sq Ft

  66 Deer Ct Dr, Middletown, NY 10940

  Well-maintained 2-bedroom, 2-bath condo in the Deer Run Community with an open layout and good natural light. Building entry with controlled access and interior access to the second-floor unit. The living and dining areas are combined and connect to a galley kitchen with a pass-through opening. The primary bedroom features a walk-in closet and a private full bathroom. New carpet was installed in

  Jie Liu KW Hudson Valley United

  66 Deer Ct Dr, Middletown, NY 10940
• 

  

  /34

  $225,000

  $5K PRICE INCREASE

  • 2 Beds
  • 1 Bath
  • 921 Sq Ft

  45 John St, Middletown, NY 10940

  Opportunity awaits! 2-bedroom, 1-bath one-family home with 2-car garage. Includes a large patio above the garage. Eat in kitchen with refrigerator and gas stove. The seller gutted and renovated the house in 1989. Property requires complete renovation and is being sold as-is. Ideal for investors, contractors, or buyers looking to build equity. Convenient location close to shopping, schools, and

  Jeffrey Lyons Curasi Realty, Inc.

  45 John St, Middletown, NY 10940
• 

  

  /24

  $399,999

  • 3 Beds
  • 3 Baths
  • 2,016 Sq Ft

  52 Linden Ave, Middletown, NY 10940

  This spacious 2,016 sq. ft. two-family home offers flexibility for both homeowners and investors. The first-floor unit features 1 bedroom, 1 full bathroom, and direct access to the basement. The second-floor unit offers 2 bedrooms and 2 full bathrooms, providing comfortable living space for occupants.Whether you're looking to live in one unit and generate rental income from the other, or

  Carina Villalona Hudson Premium Realty

  52 Linden Ave, Middletown, NY 10940
• 

  

  /46

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft

  1 Hulse St, Middletown, NY 10940

  Welcome home! This stunning newly constructed corner-lot residence offers the perfect blend of modern luxury, thoughtful design, and comfortable everyday living.Step inside to a bright, open main level featuring 9-foot ceilings, creating an inviting sense of space and sophistication. The heart of the home is the impressive upgraded kitchen, designed for both everyday living and entertaining.

  Anita S. Cristiano HomeSmart Homes & Estates

  1 Hulse St, Middletown, NY 10940
• 

  

  /8

  $159,000

  • Land
  • 18,600 Sq Ft
  • $372,365 per Acre

  47 Carpenter Ave, Middletown, NY 10940

  PRICE IMPROVED - Available for Sale is this Prime Vacant Lot with great visibility and traffic count. Zoned HC (Highway Commercial). Permitted uses include Financial institutions, office, religious, retail and service and repair shops. Uses by special permit include clubs and lodges, day care facilities, eating/drinking establishments, funeral parlors, hotel/motel, shopping centers, veterinary

  Jacqueline Henry-Thompson Jackie Henry Realty LLC

  47 Carpenter Ave, Middletown, NY 10940

Showing Results 81 - 120, Page 3 of 4