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Homes for Sale near Middletown High School

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  • /30

    $410,000

    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft

    25 Fairways Dr Unit 1, Middletown, NY 10940

    Step into this fully updated, move-in ready luxury condo located in one of the area’s most sought-after gated communities. This stunning first-floor residence has been meticulously upgraded from top to bottom—featuring designer finishes, fresh modern paint tones, and premium luxury flooring throughout. The custom kitchen is outfitted with elegant cabinetry, granite countertops, and stylish

    Agent Photo

    Randolph Rogers

    eXp Realty

    (845) 299-8068

    25 Fairways Dr Unit 1, Middletown, NY 10940
  • /25

    $420,000 Open Sat 2PM - 4PM

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    71 Commonwealth Ave, Middletown, NY 10940

    Welcome to the perfect blend of comfort, character, and location. Nestled in the vibrant heart of Middletown, NY—just 70 miles from NYC—this beautifully updated home offers a peaceful retreat without sacrificing proximity. Whether you’re commuting for work or play, nearby transportation options, including the Metro-North train and major highways, make travel to the city a breeze. And when you're

    Agent Photo

    Brian Caplicki

    Keller Williams Hudson Valley

    (845) 436-3953

    71 Commonwealth Ave, Middletown, NY 10940
  • /42

    $475,000

    • 3 Beds
    • 3 Baths
    • 2,542 Sq Ft

    138 Reinhardt Rd, Middletown, NY 10940

    Nestled on 1.5 park like acres with lots of privacy in the back, built in 1969 and lovingly cared for by the same family for over 56 years is this unique front back split level with four levels in the home. Step through the front door to find a half bath, home office with lots of shelving already in place, and second room used as a craft room, play room,or additional home office conveniently

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    Lynelle Alessi

    Keller Williams Hudson Valley

    (845) 447-9473

    138 Reinhardt Rd, Middletown, NY 10940
  • /2

    $250,000

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    13 Smith St, Middletown, NY 10940

    Looking to add a rental property to your porfolio? This 3 bedroom, 1 bathroom home might be the one. Long term tenant looking to stay. Located in the heart of the city of Middletown. Walking distance to local shops, restaurants, supermarket, park and much more. Located on a one way street with low local traffic. Call today for appoiintment.

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    Dulce M Ferrera

    Keller Williams Hudson Valley

    (845) 299-0839

    13 Smith St, Middletown, NY 10940
  • /26

    $410,000

    • 4 Beds
    • 2 Baths
    • 1,668 Sq Ft

    31 Beattie Ave, Middletown, NY 10940

    Great 2 family home in the city of Middletown. Each apartment features 2 bedrooms, 1 bathroom. This property is located in a zoning that requires one of the apartments is occupied by the owner. House is well maintained and cared for. Large lot offers plenty of yard and parking. Walk-up attic offers plenty of storage. Each tenant has their own washer and dryer hook-up. Detached 2 car garage ideal

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    Dulce M Ferrera

    Keller Williams Hudson Valley

    (845) 286-4605

    31 Beattie Ave, Middletown, NY 10940
  • /2

    $380,000

    • 5 Beds
    • 2 Baths
    • 2,440 Sq Ft

    44 Houston Ave, Middletown, NY 10940

    Excellent opportunity to own a 2 family house whether you are an investor or want to live in one of the units and rent the second one. Spacious apartments. First floor apartment has 3 bedrooms and 1 bathroom, second floor apartment has 2 bedrooms and 1 bath. Conveniently located, walking distance to Touro College where students are always looking for close by rentals. Minutes to I86 and I84,

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (845) 497-6793

    44 Houston Ave, Middletown, NY 10940
  • /21

    $640,000

    • 4 Beds
    • 3 Baths
    • 2,552 Sq Ft

    125 Whipple Rd, Middletown, NY 10940

    Discover the perfect blend of serenity and comfort in this stunning 4-bedroom, 3-bathroom raised ranch nestled on a sprawling 1.5-acre lot in the heart of Middletown, NY. As you step inside, the heart of the residence, a spacious and sunlit living area, invites family gatherings and effortless entertaining. Culinary enthusiasts will delight in the modern kitchen, boasting sleek appliances and

    Eboni Navas Julia B Fee Sothebys Int. Rlty

    125 Whipple Rd, Middletown, NY 10940
  • /36

    $625,000

    • 4 Beds
    • 3.5 Baths
    • 2,760 Sq Ft

    214 Phillips St, Middletown, NY 10940

    Welcome to this beautiful newly built 4-bedroom, 3.5-bath home featuring a spacious 2,760 sqft layout across three levels of living space. The gourmet kitchen features an island with a breakfast bar and flows seamlessly into a large dining area. The luxurious primary suite includes a full ensuite bath with dual vanities, a shower, and a separate soaking tub, all highlighted by expansive windows.

    Donna Gray Redfin Real Estate

    214 Phillips St, Middletown, NY 10940
  • /38

    $499,999 Coming Soon

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

    7 Avoncroft Ln, Middletown, NY 10940

    Discover the perfect balance of modern design and everyday comfort in this beautifully updated 3-bedroom, 3-bath corner townhouse, ideally located in one of Middletown’s most sought-after neighborhoods. Step inside and be welcomed by a bright, open-concept living space that feels both chic and inviting. The stylishly renovated kitchen is a true standout and it is complete with sleek countertops,

    Kewin Garabito eXp Realty

    7 Avoncroft Ln, Middletown, NY 10940
  • /27

    $429,000

    • 3 Beds
    • 2.5 Baths
    • 2,223 Sq Ft

    104 Monhagen Ave, Middletown, NY 10940

    Step into timeless charm with this beautifully renovated Victorian-style home! This bright and sunny 3-bedroom, 2.5-bath residence has been thoughtfully updated while maintaining its classic character. Gleaming hardwood floors flow throughout, and the inviting wrap-around porch offers the perfect spot for morning coffee or evening relaxation. Inside, you’ll find an open and airy layout with

    Jeffrey Hozias Howard Hanna Rand Realty

    104 Monhagen Ave, Middletown, NY 10940
  • /34

    $339,900

    • 3 Beds
    • 2.5 Baths
    • 1,919 Sq Ft

    110 Deer Ct Dr, Middletown, NY 10940

    Welcome to 110 Deer Court Drive, a bright and well maintained 3-bedroom, 2.5-bath unit in the highly sought-after Deer Run community in Middletown, NY. This inviting home features a spacious open floor plan filled with natural light, perfect for both everyday living and entertaining. The living room offers a cozy wood-burning fireplace while the separate dining area flows seamlessly into the

    Patricia Sassi RE/MAX Benchmark Realty Group

    110 Deer Ct Dr, Middletown, NY 10940
  • /39

    $415,789

    • 5 Beds
    • 2 Baths
    • 1,920 Sq Ft

    15 Rowan St Unit 13, Middletown, NY 10940

    Discover the perfect blend of comfort and charm in this beautifully updated home, nestled on a coveted double corner lot. Surrounded by lush hedges and offering ample parking, this residence welcomes you with curb appeal and room to spare. Inside, you'll find five spacious bedrooms, including a convenient first-floor bedroom, ideal for guests or flexible living needs. The home boasts two full

    Juan Bautista Keller Williams Realty

    15 Rowan St Unit 13, Middletown, NY 10940
  • /35

    $489,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,823 Sq Ft

    30 Wilson St, Middletown, NY 10940

    MAGAZINE READY!!!! HGTV CALLED, YOUR DREAM HOME JUST HIT THE MARKET! Absolutely Stunning Newly Renovated Raised Ranch in Middletown! Prepare to be impressed by this incredible, newly renovated raised ranch, ideally situated in a quiet and peaceful Middletown neighborhood. Thoughtfully redesigned with impeccable taste and high end, on-trend finishes, this home offers both style and substance in

    Frank Muccari Cronin & Company Real Estate

    30 Wilson St, Middletown, NY 10940
  • /17

    $309,900

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

    71 Jordan Ln, Middletown, NY 10940

    Welcome to this sought-after 2-bedroom, 2.5-bath townhouse in Mountainside Hills Condominium. The main level has hardwood floors, a kitchen dining area, a spacious living room with access to your private deck, a powder room, and an in-unit laundry room. Upstairs, you'll find the primary bedroom with an ensuite bathroom and walk-in closet, plus an additional bedroom and a full bath. The home also

    Jonathon Lee Keller Williams Hudson Valley

    71 Jordan Ln, Middletown, NY 10940
  • /31

    $589,900

    • 4 Beds
    • 2.5 Baths
    • 2,628 Sq Ft

    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
  • /26

    $265,000

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

    162 Deer Ct Dr, Middletown, NY 10940

    Beautiful Condo in a Prime Location!Experience the perfect blend of comfort and convenience in this ideally located condo, perfect for commuters and those who love being close to the action. Just minutes from major highways, this home offers easy access to shopping centers, restaurants, and daily essentials.For city bound travelers, transportation is a breeze with nearby access to the

    Beverly Huaman Howard Hanna Rand Realty

    162 Deer Ct Dr, Middletown, NY 10940
  • /20

    $269,900

    • 2 Beds
    • 2.5 Baths
    • 880 Sq Ft

    147 Ruth Ct, Middletown, NY 10940

    Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in Middletown! Featuring a spacious and inviting layout, this condo boasts a generously sized primary bedroom with a walk-in closet. Conveniently located close to shops, restaurants, and entertainment, you'll love the ease of access to everything you need. Whether you're relaxing at home or exploring the vibrant local area, this

    Matthew Gibbs Keller Williams Hudson Valley

    147 Ruth Ct, Middletown, NY 10940
  • /16

    $429,999

    • 6 Beds
    • 2 Baths
    • 1,878 Sq Ft

    19 Wawayanda Ave, Middletown, NY 10940

    Price reduced....... A Must see... Fully available opportunity knocks to own this colonial home, located in the heart of the Hudson Valley. Entering this home with a long foyer that leads into a living room, spacious dining room with plenty of natural light, eat in kitchen, Kitchen is updated with lots of cabinet space front deck, back porch, new flooring for the entire house. New roof,

    Samar Tarazi Keller Williams Realty

    19 Wawayanda Ave, Middletown, NY 10940
  • /30

    $449,900

    • 3 Beds
    • 2.5 Baths
    • 1,987 Sq Ft

    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
  • /26

    $430,000

    • 4 Beds
    • 2.5 Baths
    • 1,620 Sq Ft

    47 Prince St, Middletown, NY 10940

    Welcome to this lovely, renovated. Formerly a 3 bedroom/2-bathroom house, this home has been renovated in 2023 into a 4 bed/2.5 bath adding a 1st Floor Master Bedroom Suite, increasing the square footage of living space. This house has plenty of character and is better than new construction. Open Concept Layout, Enclosed Porch, Luxury Vinyl Flooring, Stainless Steel Appliances, Butcher Block

    D'Wana Haynesworth YourHomeSold Guaranteed Realty

    47 Prince St, Middletown, NY 10940
  • /2

    $419,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,245 Sq Ft

    77 Prince St, Middletown, NY 10940

    Welcome to this beautiful well maintained contemporary two story home nestled in the heart of Middletown. Offering you a bright and spacious living room to a formal dining room, a beautiful kitchen, 3 great size bedrooms, 2.5 bathrooms with a full size basement and a car garage. Plus plenty of closets with its laundry room. With its level backyard and great size deck, you will enjoy your

    Anita S. Cristiano HomeSmart Homes & Estates

    77 Prince St, Middletown, NY 10940
  • /27

    $295,000

    • 3 Beds
    • 1.5 Baths
    • 1,400 Sq Ft

    105 Sheffield Dr, Middletown, NY 10940

    Town of Wallkill Townhouse - Low Taxes - Great InvestmentThis charming 3-bedroom, 1.5-bath home is your perfect mix of space, location, and value. Nestled on a generous lot with a large yard, there's plenty of room for play, gardening, or entertaining under the stars. Step out from your primary bedroom onto a balcony—the ideal spot for morning coffee or winding down with a book while

    Cindy-Lee Dorcely Keller Williams Hudson Valley

    105 Sheffield Dr, Middletown, NY 10940
  • /19

    $519,000

    • 2 Beds
    • 2 Baths
    • 3,090 Sq Ft

    6 Broad St, Middletown, NY 10940

    Great two family duplex located in the City of Middletown. It's conveniently located walking distance to Touro College , I84 and I86, and also close to local shops and restaurants . Located approximately 70 miles North of New York City this property has a strong income potential with long term upside . At one time this was a triplex and is now a legal duplex. The 2nd floor apartment has 2

    Neal Kolze Curasi Realty, Inc.

    6 Broad St, Middletown, NY 10940
  • /21

    $280,000

    • 5 Beds
    • 2 Baths
    • 1,941 Sq Ft

    30 East Ave, Middletown, NY 10940

    CALLING ALL INVESTORS! Turn of the century charmer located right in the heart of Middletown! This home offers a spacious kitchen, large formal dining area, mudroom/laundry room, 2 full bathrooms, and 5 bedrooms! Unfinished basement and attic offer even more space and potential. Many original features such as tin ceiling, built-ins, and gorgeous moulding and woodwork. Large, level, fenced-in

    Jennifer Lappe Keller Williams Realty

    30 East Ave, Middletown, NY 10940
  • /15

    $465,000 Open Sun 1PM - 3PM

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

    30 Avoncroft Ln, Middletown, NY 10940

    **Welcome to 30 Avoncroft Lane, Middletown, NY!**This beautifully maintained 3-bedroom, 2.5-bath townhouse is nestled in the desirable Woodside Knolls community. Step inside to discover updated flooring throughout and a bright, versatile layout perfect for modern living. The spacious finished basement offers endless possibilities—use it as a home gym, playroom, family room, or your own

    Cindy-Lee Dorcely Keller Williams Hudson Valley

    30 Avoncroft Ln, Middletown, NY 10940
  • /15

    $125,000

    • Land
    • 2.40 Acres
    • $52,083 per Acre

    0 Kirbytown Rd Unit KEY891815, Wawayanda, NY 10940

    Build your dream home on a 2.4-acre parcel with a perfect balance of country charm and convenience. Welcome to a rare and exciting opportunity: a pristine parcel of land, perfectly situated within the esteemed Minisink Valley School District. This property presents the ideal canvas for those seeking to design and build their dream home in an idyllic country setting, without sacrificing

    Annie Hansen Howard Hanna Rand Realty

    0 Kirbytown Rd Unit KEY891815, Wawayanda, NY 10940
  • /45

    $450,000

    • 5 Beds
    • 2 Baths

    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
  • /16

    $649,900

    • 4 Beds
    • 3 Baths
    • 2,444 Sq Ft

    744 Mount Hope Rd, Middletown, NY 10940

    A beautiful colonial home sitting on 10.80 acres with open layout is being built in the town of Wallkill. Offering about 2400 SQFT living space including the finished basement with 4 bedrooms, 3 full bathroom and a one car garage. From the living room to a dining area and it's open to a beautiful kitchen with Quartz countertops, an island and stainless appliances. This gorgeous home will have 1

    Anita S. Cristiano HomeSmart Homes & Estates

    744 Mount Hope Rd, Middletown, NY 10940
  • /40

    $489,000

    • 3 Beds
    • 2.5 Baths
    • 2,491 Sq Ft

    5 Cornwall Ln, Middletown, NY 10940

    Welcome to this ending unit townhouse nestled in the community of Woodside Knolls. This beautifully maintained home offers 3 spacious bedrooms, 2.5 bathrooms, and an attached 2-car garage. With over 2,400 square feet of living space, this residence seamlessly blends comfort, and functionality. Step inside to discover the Oak Hardwood Floors throughout the main level. The bright and airy living

    Wenpeng Guan Keller Williams Hudson Valley

    5 Cornwall Ln, Middletown, NY 10940
  • /22

    $249,900

    • 2 Beds
    • 1 Bath
    • 820 Sq Ft

    58 Wawayanda Ave, Middletown, NY 10940

    A Great Place to Call Home or perfect for those looking to expand your real estate investment portfolio, this charming Middletown home offers the perfect blend of comfort, convenience, and value. Cozy yet spacious, this home has been thoughtfully updated and is truly move-in ready! With 2 bedrooms, a home office which offers much potential for additional space and a full bath you will have all

    Frank Muccari Cronin & Company Real Estate

    58 Wawayanda Ave, Middletown, NY 10940
  • /17

    $315,000

    • 3 Beds
    • 1.5 Baths
    • 1,220 Sq Ft

    38 Sheffield Dr, Middletown, NY 10940

    Welcome to this beautiful 3-bedroom, 1.5-bath townhouse-style single-family home, ideally located on a spacious corner lot in the heart of Middletown, NY. This charming residence has been freshly painted throughout and features brand-new carpeting, offering a bright, clean, and move-in-ready atmosphere from the moment you step inside.The home’s thoughtful layout provides a comfortable and

    Malik Subhani Weichert Realtors

    38 Sheffield Dr, Middletown, NY 10940
  • /29

    $349,750 Open Sun 11AM - 1PM

    • 2 Beds
    • 1 Bath
    • 1,324 Sq Ft

    9 Grandview Ave, Middletown, NY 10940

    Step inside this Middletown ranch home and be pleasantly surprised by the spacious layout, updated features, and inviting vibe that make this home a true gem. With newer windows, kitchen appliances, and central air conditioning, comfort and convenience are already checked off your list. The cute breezeway connecting the garage to the house adds a fun bonus space—think sunny sitting area or

    Patricia Sassi RE/MAX Benchmark Realty Group

    9 Grandview Ave, Middletown, NY 10940
  • /9

    $395,000

    • 4 Beds
    • 2 Baths

    25 Mill St, Middletown, NY 10940

    Beautifully recently renovated 2 story, with 2 br apartment on second for at $2000./month, has 2 yr lease, vacant first floor unit with matching new renovation, includes washer and dryer. New kitchen with granite counters, new full tile bath. High efficiency furnaces. First floor is a commercial space, ready to occupy. Tenant pay utilities. Come and see!!!!

    Mark Tierney Howard Hanna Rand Realty

    25 Mill St, Middletown, NY 10940
  • /15

    $349,000

    • 2 Beds
    • 1 Bath
    • 1,152 Sq Ft

    112 Sunrise Park Rd, New Hampton, NY 10958

    Welcome to 112 Sunrise Park Road! Tucked away at the end of a quiet cul-de-sac, this 2-Bedroom, 1-Bath gem offers the perfect blend of privacy and convenience. Located just outside of town, you’ll enjoy peaceful living with quick access to all major highways and town amenities. The home features an oversized 2-car garage and a full unfinished basement brimming with potential—whether you envision

    Ryan Barrett Keller Williams Realty

    112 Sunrise Park Rd, New Hampton, NY 10958
  • /28

    $330,000

    • 3 Beds
    • 1 Bath
    • 1,263 Sq Ft

    11 1/2 Dolson Ave, Middletown, NY 10940

    Back on the Market — Buyer’s Opportunity!This move-in-ready and renovated 3-bedroom Cape Cod in the heart of Middletown combines classic charm with modern updates. Step into a bright, spacious layout featuring a sun-filled living room, formal dining area, and a beautifully updated kitchen — ideal for both daily living and entertaining.The walk-out basement offers generous storage, a

    Robert Siracuse Absolute Real Estate of NY Inc

    11 1/2 Dolson Ave, Middletown, NY 10940
  • /16

    $355,000

    • 4 Beds
    • 2 Baths
    • 1,486 Sq Ft

    184 Highland Ave, Middletown, NY 10940

    Here you have a beautiful Victorian style home, centrally located in Middletown NY. This home features a beautiful wrap around porch that presents a charming appeal to all visitors of the property. The property has been upgraded by the current owner, they have put in $55k of upgrades which include an updated kitchen, new central air system, new doors, and new windows! The home encompasses 4

    Jorge Lugo Real Broker NY LLC

    184 Highland Ave, Middletown, NY 10940
  • /2

    $40,000

    • 550 Sq Ft

    40 Ivory Ln, Middletown, NY 10940

    THIS SPACIOUS PARCEL OF LAND IN MIDDLETOWN, NY OFFERS AN EXCELLENT OPPORTUNITY FOR AFFORDABLE LIVING OR INVESTMENT. THIS PROPERTY OFFERS THE OPPORTUNITY TO REPLACE THE EXISTING STRUCTURE WITH CONVENIENT ACCESS TO UTILITIES THE LOT IS READY FOR REDEVELOPMENT. WHETHER YOUR'RE LOOKING TO BUILD EQUITY OR SEEKING RENTAL INCOME POTENTIAL THIS PROPERTY COMBINES AFFORDABILITY WITH FLEXIBILITY. LOCATED

    ALISON NIXON eXp Realty

    40 Ivory Ln, Middletown, NY 10940
  • /50

    $875,000

    • 4 Beds
    • 4 Baths
    • 3,699 Sq Ft

    21 Lincoln Terrace Unit 19, Middletown, NY 10940

    Step into a rare and iconic mid-century modern residence, masterfully designed and once inhabited by renowned local architect Dennis Jurow. Tucked away on a private and mature one-acre lot in Middletown, this 4,000+ square foot home is a true celebration of 1970s contemporary design—thoughtfully preserved with original details throughout. This one-of-a-kind home features ten sliding glass doors

    Patricia Sassi RE/MAX Benchmark Realty Group

    21 Lincoln Terrace Unit 19, Middletown, NY 10940
  • /6

    $7,500,000

    • Land
    • 215 Acres
    • $34,884 per Acre

    0 Maples Rd Unit KEY883753, Wallkill, NY 10940

    Incredible 273-Unit Development Opportunity – Over 215 Acres! Unlock the potential of this prime 215+ acre parcel, fully site plan approved for a thoughtfully designed 273-unit residential community. The approved plans include:155 three-bedroom townhomes103 two-bedroom rental units15 three-bedroom rental unitsSituated in a high-demand area with strong demographics and minimal

    Lawrence Citarelli First Hampton Int'l Realty LLC

    0 Maples Rd Unit KEY883753, Wallkill, NY 10940
  • /45

    $353,000

    • 3 Beds
    • 1.5 Baths
    • 1,564 Sq Ft

    38 Wilson St, Middletown, NY 10940

    Welcome to 38 Wilson where charm, space, and potential come together.This 3-bedroom, 1.5-bath split-level home offers a fresh start with newly painted interiors and a layout full of possibility. Step inside to soaring cathedral ceilings and a bright open-concept kitchen, perfect for both everyday living and entertaining. Upstairs features three generously sized bedrooms and a full bathroom.

    Pete Koutros Keller Williams Hudson Valley

    38 Wilson St, Middletown, NY 10940

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