Middletown, NY Homes

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  /13

  $275,000

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  16 Woodland Rd, Middletown, NY 10940

  Welcome home to this nice three bedroom 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 total

  Joseph Paoli Howard Hanna Rand Realty

  16 Woodland Rd, Middletown, NY 10940
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  /2

  Call for Price

  Apartment for Rent

  2 Beds

  140 Highland Ave, Middletown, NY 10940

  140 Highland Ave, Middletown, NY 10940
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  $660,000 Sold Oct 29, 2025

  • 2,378 Sq Ft
  • $278/SF
  • 4 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2025

  12 Beyers Rd, Middletown, NY 10941

  New construction colonial on a 2.5 acre lot. The Reese model colonial offers 4 bedrooms and 2.5 baths. First floor bedroom along with the living room with hardwood floors and cozy fireplace, dining room with sliders leading out to deck, custom kitchen w/center island, quartz countertops and oversized pantry. The laundry room is conveniently located on the expansive 2nd level along with 3 bedrooms

  Chris Ogden Realty Promotions Inc

  12 Beyers Rd, Middletown, NY 10941
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  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 888 Sq Ft

  923 Tower Ridge Cir, Middletown, NY 10941

  923 Tower Ridge Cir, Middletown, NY 10941
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  /20

  $249,900

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  193 Schutt Rd, Middletown, NY 10940

  Why rent when you can purchase this updated, move-in-ready 3-bedroom home? This property presents an excellent opportunity for first-time homebuyers, especially with its low taxes. The kitchen features granite countertops, ample cabinet space, stainless steel appliances, and a breakfast bar open to the living room. The spacious living room is filled with natural light, making it a welcoming

  Jeanmarie Valentin HomeSmart Homes & Estates

  193 Schutt Rd, Middletown, NY 10940
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  /11

  $2,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft
  • Townhouse for Rent

  14 Columbine Ct, Middletown, NY 10940

  Spacious 3 bedroom 2.5 bath townhouse available for rent. 1st floor living room, kitchen, dining room and half bath. Upstairs 3 bedrooms and 2 full baths. One being part of the primary bedroom. Large backyard and plenty of parking. Utilities are NOT included.

  Walter Welsh HomeSmart Homes & Estates

  14 Columbine Ct, Middletown, NY 10940
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  $620,000 Sold Oct 27, 2025

  • 3,328 Sq Ft
  • $186/SF
  • 21 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1992

  58 White Bridge Rd, Middletown, NY 10940

  Welcome to your own Alpine retreat in the heart of the Hudson Valley and in the Minisink school district! Inspired by traditional German design, this warm and inviting home offers a harmonious blend of rustic charm and modern functionality. Nestled on 1.2 acres of beautifully manicured grounds, the property exudes pride of ownership and has been meticulously maintained by its current owners. Step

  Patricia Sassi RE/MAX Benchmark Realty Group

  58 White Bridge Rd, Middletown, NY 10940
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  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 888 Sq Ft

  943 Tower Ridge Cir, Middletown, NY 10941

  943 Tower Ridge Cir, Middletown, NY 10941
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  /6

  $1,550,000

  • 5 Beds
  • 5.5 Baths
  • 4,365 Sq Ft

  79 Bisch Rd, Middletown, NY 10940

  Discover the allure of 89 sprawling acres in Orange County, New York, featuring a charming farm house and a tranquil pond. The farmhouse, with its rustic charm and scenic surroundings, holds immense potential as a delightful Airbnb destination or a mini vacation retreat. Its spacious interior, cozy ambiance, and proximity to nature make it an idea I spot for relaxation and rejuvenation.

  Siang Liu P R O Links Realty Inc

  79 Bisch Rd, Middletown, NY 10940
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  /2

  Call for Price

  Cambridge Manor

  1 Bed

  28-38 Stoneridge Rd, Middletown, NY 10941

  28-38 Stoneridge Rd, Middletown, NY 10941
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  $950,000 Sold Oct 27, 2025

  • 2,000 Sq Ft
  • $475/SF
  • 24 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2000

  190 Crans Rd, Middletown, NY 10941

  Location, Location, Location! This private 55 acre Orange County, New York horse friendly property is located 75 miles north of Manhattan and features: a brand new roof (July 2025), an open floor plan house tucked at the end of a long driveway, a 4 stall center aisle horse barn with water and electric and two large horse paddocks, each with their own Nelson brand automatic waterer and 2 run-in

  Deb Cor Exclusively Equine Prop LLC

  190 Crans Rd, Middletown, NY 10941
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  Est $482,926 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,521 Sq Ft

  43 Woodside Knolls Dr, Middletown, NY 10940

  43 Woodside Knolls Dr, Middletown, NY 10940
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  /20

  $131,250

  • 1 Bed
  • 1 Bath
  • 654 Sq Ft

  440 Mt Orange Rd, Middletown, NY 10940

  VALUE IS IN THE LAND! Prime 1+ acre lot - attention builders/investors! Home has no heating system - CASH or RENOVATION LOANS only. Seller shall respond to all offers on or about 12 DAYS AFTER LIST DATE (11/24/1025).

  Patrick Lynch Prime Partner Realty

  440 Mt Orange Rd, Middletown, NY 10940
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  /32

  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,249 Sq Ft
  • Condo for Rent

  934 Tower Ridge Cir, Middletown, NY 10941

  Come home to Tower Ridge Grande! Step inside and you'll be struck by the spaciousness of the condo and recognize as well how the brilliant open floor plan offers privacy for each bedroom. Set apart from the living spaces, the entire primary suite (approx 12' x 15' bedroom) and two-sink en suite bath offer refuge and can be made completely private from the rest of the living space. The second

  Edward Sattler BHG Real Estate Green Team

  934 Tower Ridge Cir, Middletown, NY 10941
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  $442,900 Sold Oct 27, 2025

  • 1,987 Sq Ft
  • $223/SF
  • 112 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1950

  7 Roosevelt Ave, Middletown, NY 10940

  Welcome to this charming ranch-style home located on a desirable corner lot in the city of Middletown. Spanning just under 2,000 square feet, this inviting residence features spacious rooms throughout. As you enter, you'll be greeted by custom woodwork and elegant wainscoting that add a touch of sophistication throughout this home. The layout is accentuated by tile flooring that flows seamlessly

  Patricia Sassi RE/MAX Benchmark Realty Group

  7 Roosevelt Ave, Middletown, NY 10940
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  Est $484,577 Not Listed For Sale

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

  81 Woodside Knolls Dr, Middletown, NY 10940

  81 Woodside Knolls Dr, Middletown, NY 10940
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  /17

  $109,888

  • Land
  • 3 Acres
  • $36,629 per Acre

  125 Dimmick Mountain Rd, Middletown, NY 12430

  2.75 ACRE SCENIC LOT WITH NYC DEP APPROVALS – DIMMICK MOUNTAIN RD, MIDDLETOWN, NY ADDRESS: DIMMICK MOUNTAIN ROAD, MIDDLETOWN, NY 12455............... LOT SIZE: 2.75 ACRES TYPE: VACANT LAND – RESIDENTIAL ZONING UTILITIES: ELECTRIC ON-SITE, EXISTING DUG WELL PROPERTY OVERVIEW WELCOME TO YOUR PERFECT CATSKILLS RETREAT OPPORTUNITY.............A SPACIOUS AND SCENIC 2.75-ACRE VACANT LOT ON DIMMICK

  Joseph Lombardo Listing by Lombardo Homes & Estates

  

  125 Dimmick Mountain Rd, Middletown, NY 12430
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  /25

  $1,695 - $2,600 per month

  Kensington Manor

  1 - 3 Beds

  1 Kensington Manor, Middletown, NY 10941

  Kensington Manor sets a new standard of quality, beauty and sophistication in a country setting. These contemporary, spacious apartment homes are conveniently located near New York City, minutes from I-84, Route 17 and The Catskills. Relax in our swimming pool or on your private balcony. Excellent school system, convenience and location...you'll be glad to call Kensington Manor home!

  1 Kensington Manor, Middletown, NY 10941
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  $199,000 Sold Oct 27, 2025

  • 830 Sq Ft
  • $240/SF
  • 135 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1976

  27 Sycamore Dr Unit Bldg 2 A, Middletown, NY 10940

  EASY LIVING IN THIS WELL KEPT, 1 BEDROOM, 1 BATH CONDO IN THE DESIRABLE CLEMSON PARK COMMUNITY!! GREAT FOR A STARTER OR RETIREMENT HOME, THIS COMMUNITY OFFERS A COMMUNITY CLUBHOUSE FOR EVENTS AND A BEAUTIFUL OUTDOOR POOL AMONGST A WOODED VIEW! Sit back and relax and enjoy your home, as outdoor maintenance and snow removal is included in your low monthly dues. Condo interior needs a fresh coat of

  Dawn Moglia Stepping Stone Realty

  27 Sycamore Dr Unit Bldg 2 A, Middletown, NY 10940
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  Est $458,741 Not Listed For Sale

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

  24 Arden Ct, Middletown, NY 10940

  24 Arden Ct, Middletown, NY 10940
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  /12

  $268,000

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

  17 N Aspen Rd, Middletown, NY 10940

  This renovated 2-bedroom, 1.5-bath townhouse in Middletown offers a perfect blend of comfort and convenience! The inviting living room, filled with natural light, leads into a modern kitchen with brand-new stainless steel appliances and an adjacent washer/dryer setup. The dining room features a sliding door that opens up to a private fenced-in backyard—ideal for outdoor relaxation or

  Jonathon Lee Keller Williams Hudson Valley

  17 N Aspen Rd, Middletown, NY 10940
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  /25

  $2,200 per month

  • 2 Beds
  • 2.5 Baths
  • 1,460 Sq Ft
  • Townhouse for Rent

  25 Woodlake Dr, Middletown, NY 10940

  Don’t miss this beautifully maintained end-unit townhouse located in the desirable Spring Hollow community of Middletown. This home features 2 bedrooms and 2.5 bathrooms, including a spacious primary suite with a walk-in closet and private bath.Enjoy a serene backyard that overlooks a gorgeous pond, offering the perfect setting for relaxation or entertaining.The Spring Hollow community

  Megan Krusen eXp Realty

  25 Woodlake Dr, Middletown, NY 10940
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  $475,000 Sold Oct 24, 2025

  • 41 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1962

  16-18 Claremont Ct, Middletown, NY 10940

  Charming Renovated Duplex in Prime Middletown Location! Located just a short walk from Fancher-Daviage Park and pool, this beautifully updated duplex offers exceptional value and flexibility for owner-occupants or investors alike.The main unit features three spacious bedrooms and one stylishly updated bathroom, showcasing gleaming hardwood floors, a sun-filled lanai-style room, and a modern

  Shari Felder Keller Williams Realty

  16-18 Claremont Ct, Middletown, NY 10940
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  Est $477,786 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,521 Sq Ft

  20 Arden Ct, Middletown, NY 10940

  20 Arden Ct, Middletown, NY 10940
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  /20

  $158,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  529 5th Ave, Middletown, NY 10941

  Fantastic opportunity for a well loved 3 bedroom, 2 bathroom mobile home. Many upgrades AND a Generac Generator as well!!! Granite counters in the kitchen. Windows have all been replaced. Pex plumbing upgrades throughout. Central a/c. Ceiling fans all around the home and many windows for natural light. Primary bedroom has walk in closet and upgraded en-suite bathroom with big closet. Huge closets

  John Nahass Century 21 Full Service Realty

  529 5th Ave, Middletown, NY 10941
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  /10

  $2,116 per month

  • Studio
  • 1 Bath
  • Condo for Rent

  149 Wickham Ave Unit ID1056804P, Middletown, NY 10940

  This studio flat is designed for adventurous travelers who crave both comfort and exploration. Equipped with all the essentials, it provides a perfect base for your journeys while offering a cozy, homey atmosphere. Cleverly designed to maximize every inch, the space feels both spacious and intimate, making it an ideal retreat for those seeking a balance of adventure and relaxation.You'll be

  149 Wickham Ave Unit ID1056804P, Middletown, NY 10940
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  $350,000 Sold Oct 24, 2025

  • 2,460 Sq Ft
  • $142/SF
  • 37 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1904

  9 Albert St, Middletown, NY 10940

  WELCOME, HOME OWNERS AND INVESTORS, 3 FINISHED FLOORS! Welcome to this exceptional income generating multi-residential property! Ideally situated near Middletown’s restaurants, shopping malls, public transportation to NYC, major highways, and hospital facilities. This property offers unmatched convenience. Each apartment boasts two spacious bedrooms, an over-sized living room perfect for your

  Robert 'Bob' & Frances 'Fran' Murray Howard Hanna Rand Realty

  9 Albert St, Middletown, NY 10940
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  Est $518,039 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,427 Sq Ft

  6 Woodside Knolls Dr, Middletown, NY 10940

  6 Woodside Knolls Dr, Middletown, NY 10940
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  /32

  $330,000

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

  10 Royce Ave, Middletown, NY 10940

  MIDDLETOWN MAKES AN IDEAL PLACE TO CALL HOME, WITH IT'S VIBRANT DOWNTOWN AND EASY ACCESS TO MAJOR HIGHWAYS AND PUBLIC TRANSPORTATION TO NYC. SITUATED CLOSE TO LOCAL SHOPS, RESTAURANTS & NEARBY PARKS SITS THIS VERY WELL MAINTAINED 3 BEDROOM, 1.5 BATHROOMS, FINISHED ATTIC CHARMING COLONIAL HOME. LOCATED IN A HIGHLY DESIRABLE NEIGHBORHOOD THIS GEM FEATURES A SPACIOUS LAYOUT WITH CLASSIC

  ALISON NIXON eXp Realty

  10 Royce Ave, Middletown, NY 10940
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  /29

  $2,400 per month

  • 2 Beds
  • 1 Bath
  • 1,205 Sq Ft
  • Apartment for Rent

  33 Wickham Ave Unit 1, Middletown, NY 10940

  Beautifully Renovated 1st-Floor Apartment in Duplex HomeWelcome to this newly renovated first-floor apartment offering the perfect blend of modern comfort and classic charm. Step inside to find gleaming hardwood floors throughout, a spacious family room with bay window, and a formal dining room ideal for gatherings.The eat-in kitchen features granite countertops, brand-new stainless-steel

  Kismet Johnson eXp Realty

  33 Wickham Ave Unit 1, Middletown, NY 10940
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  $485,000 Sold Oct 23, 2025

  • 1,899 Sq Ft
  • $255/SF
  • 42 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2008

  38 Woodside Knolls Dr, Middletown, NY 10940

  Welcome to Woodside Knolls!Discover this stunning tri-level townhouse located in one of the area’s most desirable communities. This beautifully maintained home features 9' ceilings on the main level, a bright white kitchen with granite countertops and stainless steel appliances, and gleaming hardwood floors throughout the main level.Enjoy 3 spacious bedrooms and 3.5 bathrooms,

  Naomi Streicher Q Home Sales

  38 Woodside Knolls Dr, Middletown, NY 10940
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  Est $689,820 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,626 Sq Ft

  32 Stagecoach Dr, Middletown, NY 10940

  32 Stagecoach Dr, Middletown, NY 10940
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  /35

  $999,999

  • 3 Beds
  • 2.5 Baths
  • 3,315 Sq Ft

  535 County Route 22, Middletown, NY 10940

  Looking to Enjoy Life? Experience 535 Ct Rt 22 in the Minisink School District. Unique Handcrafted Home that is surrounded by Nature and Privacy. This Amazing property is backed up to a NYS Protected Conservation in addition to the existing 21 1/2 Acres of Privacy. Gorgeous Breath-taking views can be seen from almost every window of the home. Enjoy the Dramatic, Sundrenched, Eye Popping Open

  John Biasi Howard Hanna Rand Realty

  535 County Route 22, Middletown, NY 10940
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  /12

  $2,450 per month

  • 3 Beds
  • 2 Baths
  • Condo for Rent

  412 North St Unit 2, Middletown, NY 10940

  Property Id: 1050442This bi-level property is located at the boundary of Middletown and Wallkill town. The apartment has three bedrooms, two bathrooms, one living room and one eat-in kitchen. It also contains a bonus room next to the master bedroom, ideal to use as an office/study or activity room. Off street parking (up to two cars). Utilities not included. One year or longer term lease

  412 North St Unit 2, Middletown, NY 10940
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  $650,000 Sold Oct 23, 2025

  • 5,533 Sq Ft
  • $117/SF
  • 75 Days On Market

  • 8 Beds
  • 5 Baths
  • Built 1930

  203 Highland Ave, Middletown, NY 10940

  Welcome to this exceptional mother/daughter residence, where comfort seamlessly intertwines with practicality! This expansive colonial home is meticulously crafted to accommodate the diverse needs of everyone. This unique property offers two homes in one, that connect within the interior of the home— both equipped with their own front and side entrances! Yes, you read that right, this home offers

  Patricia Sassi RE/MAX Benchmark Realty Group

  203 Highland Ave, Middletown, NY 10940
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  Est $470,283 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,170 Sq Ft

  74 Upper Rd, Middletown, NY 10940

  74 Upper Rd, Middletown, NY 10940
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  /23

  $319,900

  • 2 Beds
  • 1 Bath
  • 836 Sq Ft

  36 Bert Crawford Rd, Middletown, NY 10940

  Cute and cozy and very affordable, pus close to everything. This is a great starter home or perfect for downsizing. All original hardwood floors, large bathroom and a large rear deck leading to a quiet back yard to play and relax. Brand new hot water heater and newer roof and windows. This home is close to public transportation and stores and restaurants. Original stone fireplace has not been

  Tom Pahucki Keller Williams Realty

  36 Bert Crawford Rd, Middletown, NY 10940
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  /14

  $1,900 per month

  • 3 Beds
  • 2 Baths
  • 750 Sq Ft
  • Apartment for Rent

  108 North St Unit 201, Middletown, NY 10940

  Downtown Middletown offers this updated 3 bedroom/2 bath apartment available for Nov 15th occupancy. Enter into a big kitchen with open floor layout to a dining area. Kitchen features newer stainless steel appliances, modern counters, floors & almond cabinets. A bedroom Suite with a private bath. 2 additional bedrooms with a 2nd full bathroom with newer fixtures & shower. A washer and dryer are

  Sandra Arnez Keller Williams Hudson Valley

  108 North St Unit 201, Middletown, NY 10940
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  $595,000 Sold Oct 22, 2025

  • 2,628 Sq Ft
  • $226/SF
  • 39 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1987

  658 Ingrassia Rd, Middletown, NY 10940

  Welcome to this beautifully maintained Cape Cod-style home offering 2,628 square feet of versatile living space set on a private and picturesque 2.3-acre lot. This charming residence blends classic design with modern comfort, featuring generous room sizes, abundant natural light, and timeless appeal. The main level boasts a thoughtfully designed floor plan, ideal for both daily living and

  Rebecca Matta-Candela Keller Williams Realty

  658 Ingrassia Rd, Middletown, NY 10940
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  Est $474,332 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,038 Sq Ft

  26 Maple Dr, Middletown, NY 10940

  26 Maple Dr, Middletown, NY 10940

Showing Results 201 - 240, Page 6 of 18