39

Middletown Homes for Sale

Section Image Section Image
  • /2

    $325,000 Coming Soon

    • 4 Beds
    • 1 Bath
    • 1,248 Sq Ft

    206 W Main St, Middletown, NY 10940

    Welcome to 206 West Main Street, a charming and well-located home in the heart of Middletown, NY—offering the perfect blend of character, space, and convenience. Featuring 4 generously sized bedrooms and 1 full bathroom, this home showcases beautiful hardwood floors and an abundance of natural sunlight throughout, creating a warm and inviting atmosphere. The home offers excellent functionality

    Travis Thompson Keller Williams Hudson Valley

    206 W Main St, Middletown, NY 10940
  • /50

    $568,000 Coming Soon

    • 7 Beds
    • 4.5 Baths
    • 3,592 Sq Ft

    104-108 Highland Ave, Middletown, NY 10940

    Historic Elegance Meets Modern-Day Convenience in this circa 1860 home in the heart of Middletown, NY. Pristinely positioned back from the road, set on just shy of an acre, this historic gem offers 3500+ square feet of timeless character and space. From the moment you enter, soaring ceilings, rich hardwood floors, built-ins and detailed crown molding set the tone. The expansive dining room,

    Agent Photo

    JoAnn Maxwell

    Howard Hanna Rand Realty

    (329) 210-1132

    104-108 Highland Ave, Middletown, NY 10940
  • /33

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 2,211 Sq Ft

    60 Magnolia Park Rd, Middletown, NY 10940

    Beautifully cared-for 3 bedroom, 2.5-bath townhouse in the heart of Middletown! Spanning three levels, this home offers comfortable, versatile living with hardwood floors throughout both the main and second levels. The bright main floor features an open-concept living area featuring a fireplace, a dining area, along with a modern kitchen complete with granite countertops and ample cabinet space.

    Sandra Laramore Redfin Real Estate

    60 Magnolia Park Rd, Middletown, NY 10940
  • /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 Keller Williams Hudson Valley

    129 Concord Ln Unit 129, Middletown, NY 10940
  • /25

    $329,000

    • 2 Beds
    • 2 Baths
    • 1,730 Sq Ft

    42 Mayer Dr, Middletown, NY 10940

    Charming Townhouse in the Town of Wallkill!Welcome home to this well-maintained and move-in ready 2-bedroom, 2-bath townhouse offering the perfect blend of comfort, convenience, and value — all with NO HOA fees! Step inside to find a spacious and inviting living room, perfect for relaxing or entertaining guests. The home features an eat-in kitchen along with a formal dining room, providing

    Dominick Tufano RE/MAX Benchmark Realty Group

    42 Mayer Dr, Middletown, NY 10940
  • /39

    $249,999

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    18-20 Bedford Ave, Middletown, NY 10940

    Welcome to this charming 2 bedroom, 1 bath Cape Cod located in the heart of Middletown, NY. Perfect starter home, ideal for those looking to downsize, or a fantastic investment opportunity. Upon entering, you are welcomed by beautiful hardwood floors, warm character, and a cozy feel that makes this home instantly inviting. Offering approximately 864 square feet of living space, this home is

    Jennifer Lappe Keller Williams Realty

    18-20 Bedford Ave, Middletown, NY 10940
  • /21

    $329,000

    • 2 Beds
    • 2.5 Baths
    • 1,473 Sq Ft

    209 Deer Ct Dr, Middletown, NY 10940

    Welcome to Deer Run, this inviting condo in the heart of Middletown, NY, where convenience meets comfort. Perfectly situated for commuters, this home offers easy access to major highways, shopping, dining, and transportation, making daily travel a breeze. Enjoy the best of suburban living with a peaceful atmosphere, all while being close to everything you need. Whether you're starting out,

    Beverly Huaman Howard Hanna Rand Realty

    209 Deer Ct Dr, Middletown, NY 10940
  • /23

    $435,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    47 Liberty St, Middletown, NY 10940

    Updated 3BR/2BA Home on Quiet Dead-End Street – Middletown Updated 3-bedroom, 2 full-bath home located on a dead-end street in the City of Middletown. First floor features a spacious eat-in kitchen with stainless steel appliances, large living room, dining area, and updated full bath. Sliding door off kitchen leads to backyard deck. Second floor offers 3 bedrooms and an updated full bath, plus

    Jonathon Lee Keller Williams Hudson Valley

    47 Liberty St, Middletown, NY 10940
  • /10

    $379,900

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

    37 California Ave, Middletown, NY 10940

    MLS Listing Description: Charming 3-bedroom, 2-bath traditional two-story home featuring a spacious, enclosed backyard—perfect for outdoor enjoyment and entertaining. The first floor offers an oversized living room, an open dining area, and a functional kitchen layout ideal for everyday living. Upstairs, you’ll find three comfortable bedrooms and a full bath. A walk-up attic provides convenient

    Jonathon Lee Keller Williams Hudson Valley

    37 California Ave, Middletown, NY 10940
  • /58

    $575,000

    • 12 Beds
    • 10 Baths
    • 5,004 Sq Ft

    5 Wawayanda Place, Middletown, NY 10940

    CASH ONLY - Totally renovated large home with 12 bedrooms, 8 of them being suites with their own full bathroom. 10 full bathrooms total. Home also features game room, large dining area, living room, spacious eat in kitchen with stainless appliances & island, laundry off the kitchen, large fenced patio & inground pool. Conveniently located around Orange County Community College, tennis & skate and

    Jamie Sittner Find Advisors

    5 Wawayanda Place, Middletown, NY 10940
  • /2

    $480,000

    1 Royce Ave, Middletown, NY 10940

    Excellent investment opportunity in the heart of Middletown! This well-maintained, fully occupied two-family residence offers immediate cash flow with a total monthly income of $3,500. The first-floor unit features a comfortable 1-bedroom, 1-bathroom layout currently rented for $1,600, while the second-floor unit offers a spacious 2-bedroom, 1-bathroom configuration rented for $1,900.

    Joseph Baratta Joseph Baratta Company Realty

    1 Royce Ave, Middletown, NY 10940
  • /27

    $425,000

    • 4 Beds
    • 2 Baths
    • 1,666 Sq Ft

    39 Hanford St, Middletown, NY 10940

    Coming Soon - prewar colonial in the heart of the City of Middletown.

    Soleil Jackman Howard Hanna Rand Realty

    39 Hanford St, Middletown, NY 10940
  • /13

    $560,000

    • 5 Beds
    • 4 Baths
    • 1,911 Sq Ft

    35 Dogwood Dr, Middletown, NY 10940

    Just pack your bags and move in. Spacious, Comfortable and Cozy 5 bedroom 1 family house for sale. This house features 4 Bedrooms and 2 bathrooms on the upper level with a walk in closet and a bathroom in the master bedroom. The first features a 1/2 bath, renovated kitchen, separate living and dinning rooms and a walkout deck. The ground floor features a 2 car garage, finished basement with 1

    Lenworth Brisco Keller Williams Realty NYC Grp

    35 Dogwood Dr, Middletown, NY 10940
  • /2

    $175,000

    • 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.

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (329) 210-1290

    45 Knapp Ave, Middletown, NY 10940
  • /2

    $299,900

    • 3 Beds
    • 1 Bath
    • 1,620 Sq Ft

    46 Knapp Ave, Middletown, NY 10940

    This oldie but goodie is full of potential! With a little love, fresh paint, and imagination, this home can truly shine as a wonderful starter home. It also presents a great opportunity for investors looking to expand their rental portfolio, long-term tenants would love the option to stay. Features include some hardwood floors, a detached 2-car garage, and a recently paved blacktop driveway.

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (329) 209-9787

    46 Knapp Ave, Middletown, NY 10940
  • /17

    $599,900

    • 4 Beds
    • 3 Baths
    • 2,560 Sq Ft

    55 Eisenhower Dr, Middletown, NY 10940

    Stunning Ranch in a Highly Desired Neighborhood! Welcome to this beautifully renovated ranch-style home, perfectly situated on a spacious corner lot of over 1/3 of an acre. Offering 4 generously sized bedrooms, 3 full bathrooms and central air, this home is ideal for comfortable living and entertaining.Step inside to a huge sun-filled living room featuring oversized windows that flood the

    Jennifer Kubler eRealty Advisors, Inc

    55 Eisenhower Dr, Middletown, NY 10940
  • /13

    $455,000

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

    225 Monhagen Ave, Middletown, NY 10940

    Great location with mixed-use zoning potential! This nicely maintained property offers a comfortable and practical layout that is perfect for family living.The home features 4 bedrooms and 2 full bathrooms, providing generous and comfortable living space. A finished basement offers additional room that can be used for entertainment, a recreation area, home office, or extra living

    Jin Pang Panorama Realty

    225 Monhagen Ave, Middletown, NY 10940
  • /2

    $90,000

    • 1 Bath
    • 480 Sq Ft

    109 Concord Ln, Middletown, NY 10940

    Studio apartment

    Malik Subhani Weichert Realtors

    109 Concord Ln, Middletown, NY 10940
  • /8

    $490,000

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

    19 Magnolia Park Rd, Middletown, NY 10940

    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 with granite

    Daniel Amodeo AMO Realty

    19 Magnolia Park Rd, Middletown, NY 10940
  • /30

    $515,000

    • 3 Beds
    • 2.5 Baths
    • 2,763 Sq Ft

    17 Woodrose Ct, Middletown, NY 10940

    Discover the perfect blend of classic charm and modern comfort in this beautiful Colonial-style home. Filled with warmth and character, this cozy yet spacious residence features soaring high ceilings that create an open, airy feel throughout. Each room is thoughtfully designed to offer both elegance and comfort, making the home feel inviting from the moment you step inside. With its timeless

    Ermelinda Mclaughlin eXp Realty

    17 Woodrose Ct, Middletown, NY 10940
  • /31

    $399,998

    • 4 Beds
    • 1 Bath
    • 1,296 Sq Ft

    10 Wisner Ave Unit 12, Middletown, NY 10940

    Welcome to 10 Wisner Avenue, a beautifully updated ranch that seamlessly blends style, comfort, and modern convenience. Renovated in 2023, this home features a new roof, life-proof flooring throughout, a stunning kitchen with butcher block countertops, subway tile backsplash, and stainless steel appliances, a Navien tankless heater, and a new washer and dryer. Enjoy the ease of single-level

    Sean Israelski Howard Hanna Rand Realty

    10 Wisner Ave Unit 12, Middletown, NY 10940
  • /43

    $430,000

    • 3 Beds
    • 1.5 Baths
    • 1,363 Sq Ft

    24 Rockwell Ave, Middletown, NY 10940

    Welcome home to 24 Rockwell Avenue, a beautifully updated residence that seamlessly blends comfort with modern convenience. Completely renovated in 2023, this move-in ready home features a new roof, life-proof flooring throughout, a stylish kitchen with stainless steel appliances and butcher block countertops, as well as a new washer and dryer. The functional center hall colonial layout offers

    Sean Israelski Howard Hanna Rand Realty

    24 Rockwell Ave, Middletown, NY 10940
  • /12

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,340 Sq Ft

    70 Linden Ave, Middletown, NY 10940

    Wonderful Colonial Home located in a very convenient location in the heart ofMiddletown. Walk to all the wonderful Restaurants and Shops. Enjoy the spaciousness of the home that features a Large Living Room, Formal Dining Room,Working Kitchen and Full Bathroom. Second level offers a Primary Bedroom and two additional Bedrooms and Full Bathroom. Huge walk up Attic. Full Basement. Nice

    John Biasi Howard Hanna Rand Realty

    70 Linden Ave, Middletown, NY 10940
  • /45

    $564,900

    • 4 Beds
    • 2.5 Baths
    • 2,344 Sq Ft

    1 Hulse St, Middletown, NY 10940

    "NEW CONSTRUCTION!" Stunning corner-lot home in a calm suburban setting with beautiful mountain views — offering space, upgrades, and thoughtful design throughout. This impressive property offers approximately 2,344 sq ft of living space and features 9-ft ceilings on the main level and 8-ft ceilings upstairs, enhancing the open and airy layout. The upgraded 400+ sq ft kitchen is a true highlight,

    Chaim Friedman MS Realty Group USA, Inc

    1 Hulse St, Middletown, NY 10940
  • /3

    $350,000

    • Land
    • 1.42 Acres
    • $245,752 per Acre

    65 James P Kelly Way, Middletown, NY 10940

    Great location for a business. C-3 Zoning allows for any business, commercial or residential mix use. 262 feet frontage. Annual Average Daily Traffic (AADT) for 2023 is 10,569. There was a pre-approved building plan for a doctor's office building. The land is in the city of Middletown. The city will provide water and sewer. C-3 allow for 6 story mix-use business and residential building with the

    Jonathon Lee Keller Williams Hudson Valley

    65 James P Kelly Way, Middletown, NY 10940
  • /44

    $575,000

    • 3 Beds
    • 2.5 Baths
    • 2,809 Sq Ft

    7 Starhaven Ave, Middletown, NY 10940

    This well-maintained home offers strong structural integrity, reliable mechanicals, and a flexible layout—ideal for buyers seeking a move-in-ready foundation with the opportunity to personalize cosmetic finishes over time. The main level features comfortable living and dining areas, an efficient kitchen layout, and generous natural light throughout. All bedrooms and the hallway include existing

    Michelle Gruberger Real Estate Circuit Inc

    7 Starhaven Ave, Middletown, NY 10940
  • /19

    $479,999

    • 6 Beds
    • 2 Baths
    • 2,424 Sq Ft

    80 Prospect Ave, Middletown, NY 10940

    Welcome to 80 Prospect Ave, a well-maintained six-bedroom, two-bathroom home situated in the peaceful suburban setting of Middletown, NY. Built in 1918, this 2,424 square foot residence combines traditional architectural charm with modern updates, offering nearly 6,800 square feet of usable lot space ideal for both living and outdoor enjoyment. The property features a classic two-story design

    Jonathan Paredes Locqube New York, Inc.

    80 Prospect Ave, Middletown, NY 10940
  • /12

    $410,000

    • 5 Beds
    • 4 Baths

    41 Monhagen Ave Unit 39, Middletown, NY 10940

    Sold as is?This versatile property offers the perfect blend of comfortable living and passive income generation. Whether you are a first-time homebuyer looking to offset your mortgage or a seasoned investor seeking a high-yield asset, this legal two-family home is a standout choice. The Strategy: Live for Less, Earn MoreThe property is ideally configured for an owner-occupant strategy: Main

    Zhiheng Tang Keller Williams Hudson Valley

    41 Monhagen Ave Unit 39, Middletown, NY 10940
  • /2

    $26,000

    • Land
    • 0.03 Acre
    • $812,500 per Acre

    138-1/2 Linden Ave, Middletown, NY 10940

    Lot is vacant and directly between 138 & 140 Linden Ave

    Olivia Cappelli Donna Ruffino Realty Corp

    138-1/2 Linden Ave, Middletown, NY 10940
  • /31

    $318,000

    • 2 Beds
    • 1.5 Baths
    • 1,460 Sq Ft

    47 Brick Pond Rd Unit 47, Middletown, NY 10940

    Welcome to this charming 2-story townhouse-style condo located in the Spring Hollow community. This home offers 2 bedrooms and 1.5 bathrooms. The main level features a spacious living room, a cozy eat-in kitchen, and a convenient half bath. The kitchen includes cream-colored cabinets, granite countertops, a tile backsplash, stainless steel appliances, a center island for additional workspace, and

    Jie Liu Keller Williams Hudson Valley

    47 Brick Pond Rd Unit 47, Middletown, NY 10940
  • /20

    $225,000

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    366 Concord Ln, Middletown, NY 10940

    NEW JUST RENOVATED in August 2024. Spacious 2 bedroom. 2 full bath condo. INVESTOR? THIS CAN BE RENTED IMMEDIATELY AFTER CLOSING. 1st FLOOR Private entrance, all new appliances in 2024, all new floors throughout, new washer/ dryer in unit! Spacious unit with en suite primary bedroom and additional full bath . Large second bedroom. Walk in closet. Lovely breakfast bar. Plenty of parking. Lovely

    Yolanda Hoey More and More Real Estate

    366 Concord Ln, Middletown, NY 10940
  • /22

    $350,000

    • 3 Beds
    • 1 Bath
    • 892 Sq Ft

    91 Mountain Ave, Middletown, NY 10940

    Looking for one-story living in a private dead end street, look no further as you have found it! Beautiful hardwood floors welcome you into a living room with plenty of window light followed by an eat-in kitchen that has been fully equipped with gorgeous stainless steel appliances, new counters and plenty of cabinet space. Three spacious bedrooms with plenty of closet space and a beautiful tiled

    Sandra Arnez Keller Williams Hudson Valley

    91 Mountain Ave, Middletown, NY 10940
  • /3

    $69,000

    • Land
    • 6.5 Acres
    • $10,615 per Acre

    0 County Road 49, Middletown, NY 10940

    6 Acres of Raw Land! Prime Middletown parcel with potential for residential development or investment. Quiet lot with easy access to main roads and nearby amenities. Drive-by 409 County Route 49Middletown, NY 10940 to see property. this address if the neighboring lot

    Bryant Moran YourHomeSold Guaranteed Realty

    0 County Road 49, Middletown, NY 10940
  • /27

    $215,000

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    326 Concord Ln, Middletown, NY 10940

    Buttonwood Hills Condominiums now offers a 2 bedroom/2 bath unit for your purchase & to call home! A ground level end unit with open floor 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 with a Suite with double closets and a private full

    Sandra Arnez Keller Williams Hudson Valley

    326 Concord Ln, Middletown, NY 10940
  • /15

    $264,999

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

    11 Jordan Ln, Middletown, NY 10940

    Great opportunity for investors for fix and flip.Minimal work needed to make it presentable.Town house located in a beautiful neighborhood.

    Siju John Kerala Realty, LLC

    11 Jordan Ln, Middletown, NY 10940
  • /8

    $149,000

    • 1 Bed
    • 1 Bath
    • 735 Sq Ft

    234 Concord Ln, Middletown, NY 10940

    Welcome to this inviting 1-bedroom, 1-bath residence in the heart of Middletown. Featuring an open-living layout with abundant natural light, this unit offers a seamless flow from the living room to the kitchen and plenty of storage. The generously sized bedroom boasts a large closet and easy access to the full bath. Additional perks include in-unit laundry and assigned parking. Located in a

    Malik Subhani Weichert Realtors

    234 Concord Ln, Middletown, NY 10940
  • /2

    $99,900

    • Land
    • 0.3 Acre
    • $333,000 per Acre

    28 Genung St, Middletown, NY 10940

    **Great investment opportunity in desirable area in Middletown** Not many vacant properties on the market that offer the possibility to build a multi-family unit. This lot is set back from the main road, just behind 32 Genung Street, that is a legal 2-family property.Don't miss out!

    Evelyn Unger Tmimi Weichert Realtors

    28 Genung St, Middletown, NY 10940
  • /5

    $300,000

    • Land
    • 6 Acres
    • $50,000 per Acre

    0 Mount Hope Rd, Middletown, NY

    Looking to build? Land available in prime location. Situated directly between Middletown and Town of Mount Hope with easy access to all major roadways. Zoned for residential and agriculture. Buyer/builder to subdivide 5-6 acres from this 37+ acre parcel as agreeable to seller and proposed in contract. Flat, open, cleared land may be suitable for 1-3 building lots. Land to purchase provides

    Amanda Ferrantello Hudson Valley Griffith

    0 Mount Hope Rd, Middletown, NY
  • /18

    $695,000

    • 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

Frequently Asked Questions

Is Middletown a good place to live?
Middletown is a good place to live. Middletown is considered fairly walkable and somewhat bikeable with minimal transit options. Middletown has 6 parks for recreational activities. It has a median age of 37. The average household income is $85,458 which is below the national average. College graduates make up 19.1% of residents. A majority of residents in Middletown are renters, with 57% of residents renting and 43% of residents owning their home. A local real estate agent serving Middletown can help you decide if this neighborhood is the right one for you. Learn more on our Middletown neighborhood guide.
How much do you need to make to afford a house in Middletown?
The median home price in Middletown is $349,825. If you put a 20% down payment of $70,000 and had a 30-year fixed mortgage with an interest rate of 6.37%, your estimated principal and interest payment would be $1,740 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $75K a year to afford the median home price in Middletown. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Middletown is $85K.
What are the best private schools in Middletown?
The best private schools that serve Middletown are:
What are the most popular zip codes in Middletown, Middletown, NY?
The most popular zip codes in Middletown, Middletown, NY include 10940, 10958, 10941, 12737 and 10924.
What are the most popular neighborhoods near Middletown, Middletown, NY?
The most popular neighborhoods near Middletown, Middletown, NY are Mount Hope and Greenville Town.

Home Trends in Middletown, NY

Housing Trends

Median Sale Price
$340,750
Median Single Family Sale Price
$380,000
Median Townhouse Sale Price
$350,000
Median 2 Bedroom Sale Price
$260,500
Median 1 Bedroom Sale Price
$195,600
Average Price Per Sq Ft
$241
Number of Homes for Sale
31
Last 12 months Home Sales
196
Months of Supply
1.90
Median List Price
$349,825
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
How to Buy a Home How to Finance a Home How to Sell a Home