Middletown, NY Homes

/3
$379,000 Pending
- 3 Beds
- 2 Baths
- 1,314 Sq Ft
21 Philcox Rd, Middletown, NY 10940

Rare opportunity to own two homes next door to each other in the Pine Bush School District. This one-owner 1986 ranch offers 3+ bedrooms and 2+ baths with a finished walk-out lower level. Main level features an eat-in kitchen, dining room, and spacious living room. Lower level includes a private primary bedroom and additional finished space suitable for extended living. Property includes a 3-car

Joseph Rubeo Keller Williams Hudson Valley

21 Philcox Rd, Middletown, NY 10940
/19
$2,000 Per Month
- 2 Beds
- 1 Bath
- 718 Sq Ft
- Apartment for Rent
31 Beattie Ave Unit 2, Middletown, NY 10940

Now available at 31 Beattie Ave, Apt #2 in Middletown, this well-maintained upstairs apartment offers a bright, comfortable layout in a residential neighborhood. The rent includes heat & hot water. Tenants would pay their own electricity, and includes off-street parking for added convenience. Located close to local shops, dining, and major roadways, this apartment provides easy access to everyday

Kason Fearon Serhant LLC

31 Beattie Ave Unit 2, Middletown, NY 10940
$139,999 Sold Mar 27, 2026

5 Sayer Ln, Middletown, NY 10940
- 3 Beds
- 2 Baths
- 1,080 Sq Ft
- Built 2017
Last Sold Summary
- 8% Above List Price
- $130/SF
- 42 Days On Market
Last Listing Agent Pete Wolven Hudson Valley Home Connection

5 Sayer Ln, Middletown, NY 10940

Est $484,680 Not Listed For Sale

74 Upper Rd, Middletown, NY 10940
- 4 Beds
- 2.5 Baths
- 2,170 Sq Ft
- Built 1966
74 Upper Rd, Middletown, NY 10940

Last Sold Summary
- 23% Above List Price
- $182/SF
- 178 Days On Market
- Last Sold Price $395,000
- Jul 19, 2023
Last Listing Agent Brenda Owens-Milner Keller Williams Hudson Valley

/31
$335,000
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
892 Winterton Rd, Middletown, NY 10940

Welcome home to this renovated 2 bed, 2 bath Cape on a private 1 acre lot in the Minisink School District. Enjoy a large stylish kitchen with quartz countertops, gorgeous tiled bathrooms, and a perfect blend of charm and modern comfort. First floor bedroom and bathroom, covered front porch and patio outside the kitchen. There is a barn/garage outside where you can park 2 cars. A great chance to

Valeria Rios Keller Williams Hudson Valley

892 Winterton Rd, Middletown, NY 10940
/10
$2,700 Per Month
- 3 Beds
- 1 Bath
- 1,466 Sq Ft
- House for Rent
225 Monhagen Ave, Middletown, NY 10940

Great Location on Route 211 – Spacious 3-Bedroom Upstairs Unit with Large Backyard. The well-maintained upstairs unit located on Route 211 in Middletown offers both convenience and comfortable living. This rental features 3 bedrooms, a bright and spacious living room, and a functional kitchen—perfect for everyday living. Enjoy access to a large backyard, ideal for kids’ activities, outdoor

Jin Pang Panorama Realty

225 Monhagen Ave, Middletown, NY 10940
$285,000 Sold Sep 10, 2025

234 Howells Rd, Middletown, NY 10940
- Land
- 41.6 Acres
- $6,851 per Acre
Last Sold Summary
- 24% Below List Price
- 40 Days On Market
Last Listing Agent Jonathon Lee Keller Williams Hudson Valley

234 Howells Rd, Middletown, NY 10940

Est $477,991 Not Listed For Sale

26 Maple Dr, Middletown, NY 10940
- 4 Beds
- 2 Baths
- 2,038 Sq Ft
- Built 1982
26 Maple Dr, Middletown, NY 10940

Last Sold Summary
- 9% Above List Price
- $216/SF
- 80 Days On Market
- Last Sold Price $440,000
- Jan 18, 2024
Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

/31
$425,000 Pending
- 3 Beds
- 1.5 Baths
- 1,788 Sq Ft
10 Renfrewshire Dr, Middletown, NY 10941

Welcome to 10 Renfrewshire Drive, a well-maintained 3-bedroom, 1 full and 1 half bath ranch in the Pine Bush School District, offering a comfortable layout, great outdoor space, and the everyday convenience you have been searching for.Inside, you’ll find hardwood floors and a bright, functional kitchen featuring cherry cabinetry and stainless steel appliances. The main level provides easy

Frank Muccari Cronin & Company Real Estate

10 Renfrewshire Dr, Middletown, NY 10941
/8
$2,000 Per Month
- 2 Beds
- 1 Bath
- 1,090 Sq Ft
- Apartment for Rent
31 Liberty St, Middletown, NY 10940

2 BEDROOM APARTMENT LOCATED ON SECOND LEVEL, CENTRALLY LOCATED IN CITY OF MIDDLETOWN, COMMONI HALLWAY TO ACCESS SECOND LEVEL APARTMENT. LANDLORD RESIDES ON THE FIRST FLOOR APARTMENT. 1090 SQUARE FOOT SPACE WITH FEATURES FULL SIZED WASHER AND DRYER, EAT IN KITCHEN, GREAT KITCHEN CABINET SPACE, HUGE STORAGE SPACE OFF KITCHEN. CONNECTING ROOM OFF LIVING ROOM CAN BE COMPUTER ROOM. MASTER BEDROOM HAS

Olga Krasinski Olga Krasinski Real Estate

31 Liberty St, Middletown, NY 10940
$490,000 Sold Mar 12, 2026

9 Randall Heights, Middletown, NY 10940
- 3 Beds
- 2 Baths
- 1,868 Sq Ft
- Built 1964
Last Sold Summary
- 7% Below List Price
- $262/SF
- 70 Days On Market
Current Estimated Value $496,235

Last Listing Agent Naomi Streicher Q Home Sales

9 Randall Heights, Middletown, NY 10940

Est $477,559 Not Listed For Sale

27 Cornfield Rd, Middletown, NY 10940
- 5 Beds
- 2 Baths
- 1,988 Sq Ft
- Built 1975
27 Cornfield Rd, Middletown, NY 10940

Last Sold Summary
- 7% Below List Price
- $259/SF
- 26 Days On Market
- Last Sold Price $515,000
- Jul 11, 2024
Last Listing Agent Donna Reese Keller Williams Hudson Valley

/36
$599,900 Open Thu 5PM - 7PM
- 6 Beds
- 3.5 Baths
- 2,948 Sq Ft
669 Mountain Rd, Middletown, NY 10940

Country Escape of 6 spacious bedrooms offers space, privacy, and a serene setting on 3.38 acres. Just about 75 miles from New York City, it’s close enough for convenient weekend escapes yet far enough to feel like a true retreat feels like a private estate—perfect for those seeking a refined escape from city life A grand foyer opens to a bright, airy layout with high ceilings, large windows, and

Michelle Gruberger Real Estate Circuit Inc

669 Mountain Rd, Middletown, NY 10940
/32
$4,900 Per Month
- 4 Beds
- 2.5 Baths
- 2,492 Sq Ft
- House for Rent
201 County Route 50, Middletown, NY 10940

GORGEOUS 4 bedroom/3 bath now available in the town of Wallkill. Discover your family's oasis on 4.1 acres next to West Hills Country Club! This stunning 4-bedroom home, complete with a grand master suite, will exceed your expectations. Enjoy the above-ground pool with smart monitoring, heated outdoor tub, and spacious deck with grill. Kids will love the playground, while adults appreciate the

Sandra Arnez Keller Williams Hudson Valley

201 County Route 50, Middletown, NY 10940
$330,000 Sold Sep 26, 2025

11 1/2 Dolson Ave, Middletown, NY 10940
- 3 Beds
- 1 Bath
- 1,263 Sq Ft
- Built 1900
Last Sold Summary
- $261/SF
- 35 Days On Market
Current Estimated Value $342,354

Last Listing Agent Robert Siracuse Absolute Real Estate of NY Inc

11 1/2 Dolson Ave, Middletown, NY 10940

Est $519,404 Not Listed For Sale

295 Spruce Rd, Middletown, NY 10940
- 3 Beds
- 2 Baths
- 1,881 Sq Ft
- Built 1922
295 Spruce Rd, Middletown, NY 10940

Last Sold Summary
- 7% Above List Price
- $257/SF
- 68 Days On Market
- Last Sold Price $484,000
- Apr 07, 2025
Last Listing Agent Nicola Friedman Windsor Realty Services Inc

/17
$565,000
- 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
/7
$1,675 Per Month
- 1 Bed
- 1 Bath
- 742 Sq Ft
- Apartment for Rent
77 Linden Ave Unit 79, Middletown, NY 10940

OPEN HOUSE APRIL 26, 2026 11;00 AM- 1:00 PM.Charming 1-bedroom rental offering 742 square feet of comfortable living space. This apartment features new hardwood floors, a spacious living room, 1 full bathroom, and a large eat-in kitchen with new kitchen cabinets and tile flooring. A bright and inviting space with great updates throughout.

Jean DiMatteo DiMatteo Realty LLC

77 Linden Ave Unit 79, Middletown, NY 10940
$360,000 Sold Jun 30, 2025

18 Woodland Ave, Middletown, NY 10940
- 3 Beds
- 1 Bath
- 960 Sq Ft
- Built 1955
Last Sold Summary
- 7% Above List Price
- $375/SF
- 46 Days On Market
Current Estimated Value $370,023

Last Listing Agent Kassandra Mott Keller Williams Hudson Valley

18 Woodland Ave, Middletown, NY 10940

Est $288,162 Not Listed For Sale

225 Upper Rd, Middletown, NY 10940
- 2 Beds
- 1.5 Baths
- 1,200 Sq Ft
- Built 1978
225 Upper Rd, Middletown, NY 10940

Last Sold Summary
- 11% Above List Price
- $217/SF
- 77 Days On Market
- Last Sold Price $260,000
- Feb 25, 2025
Last Listing Agent Keith Sumner John J Lease REALTORS Inc

/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
/15
$2,500 Per Month
- 3 Beds
- 1 Bath
- 1,278 Sq Ft
- House for Rent
39 Crescent Place, Middletown, NY 10940

Very Beautifully renovated home on a quiet street in Middletown. Perfect location close to schools, shopping, and playgrounds. Clean hardwood floors, updated kitchen, newly paved driveway, finished patio, and plenty of natural light. In addition, all windows were replaced in 2020Basement for personal use

Zhiheng Tang Keller Williams Hudson Valley

39 Crescent Place, Middletown, NY 10940
$425,000 Sold Jun 25, 2025

4 Deer Ct Dr, Middletown, NY 10940
- 3 Beds
- 2.5 Baths
- 1,919 Sq Ft
- Built 2002
Last Sold Summary
- 6% Above List Price
- $221/SF
- 39 Days On Market
Current Estimated Value $429,170

Last Listing Agent Dulce M Ferrera Keller Williams Hudson Valley

4 Deer Ct Dr, Middletown, NY 10940

Est $463,118 Not Listed For Sale

8 Jean Ridge Rd, Middletown, NY 10940
- 3 Beds
- 2 Baths
- 1,924 Sq Ft
- Built 1972
8 Jean Ridge Rd, Middletown, NY 10940

Last Sold Summary
- 12% Above List Price
- $216/SF
- 27 Days On Market
- Last Sold Price $415,000
- Sep 26, 2023
Last Listing Agent Adriane Werkema Easy Lifestyle Real Estate

/30
$849,000
- 5 Beds
- 2.5 Baths
- 3,764 Sq Ft
238 S Centerville Rd, Middletown, NY 10940

Spacious Country Retreat on 22.6 Acres in Minisink Valley School District This exceptional property offers privacy, comfort, and extensive amenities set on 22.6 picturesque acres. The master bedroom and bathroom were updated in 2016, complemented by a wet bar in the family room—perfect for entertaining. The home features three fireplaces and a wood stove, creating warmth and character throughout.

Linda VanDeWeert BHG Real Estate Green Team

238 S Centerville Rd, Middletown, NY 10940
/4
$1,700 Per Month
- 2 Beds
- 1 Bath
- 784 Sq Ft
- Apartment for Rent
203 W Main St Unit 2, Middletown, NY 10940

Cozy second-floor apartment located in a two-family home in the heart of Middletown. This unit offers 1 bedroom, 1 full bathroom, a kitchen, and an additional small bonus room that can be used as a home office, nursery, or storage space. The apartment features a functional layout with comfortable living space and natural light. Includes private driveway parking and access to a welcoming front

Yosseline Genao Keller Williams Hudson Valley

203 W Main St Unit 2, Middletown, NY 10940
$385,000 Sold Aug 15, 2025

11 Keats Rd, Middletown, NY 10941
- 3 Beds
- 1.5 Baths
- 1,900 Sq Ft
- Built 1986
Last Sold Summary
- 6% Below List Price
- $203/SF
- 35 Days On Market
Current Estimated Value $414,728

Last Listing Agent Christina Herschel-Huebner Herschel Realty Corp

11 Keats Rd, Middletown, NY 10941

Est $475,784 Not Listed For Sale

48 Karen Joy Dr, Middletown, NY 10940
- 3 Beds
- 2.5 Baths
- 2,030 Sq Ft
- Built 1998
48 Karen Joy Dr, Middletown, NY 10940

Last Sold Summary
- 9% Above List Price
- $214/SF
- 47 Days On Market
- Last Sold Price $435,000
- Jun 08, 2023
Last Listing Agent Jian Gonzalez RE/MAX Opulent

/26
$143,999
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
79 Stern Scenic Dr, Middletown, NY 10940

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

Ivan Carvalho Exit Realty Connections

79 Stern Scenic Dr, Middletown, NY 10940
/11
$2,600 Per Month
- 3 Beds
- 1 Bath
- 1,144 Sq Ft
- House for Rent
56 Wisner Ave, Middletown, NY 10940

OPEN HOUSE APRIL 26, 2026 11:00am -1:00 PM.This inviting two-story home offers 1,152 sq. ft. of comfortable living space. Featuring three bedrooms, one full bathroom, a bright living room, dining room, and a functional kitchen, this home combines practicality with classic charm. Enjoy the warmth and character of hardwood floors throughout and a closed-in front porch perfect for relaxing or

Jean DiMatteo DiMatteo Realty LLC

56 Wisner Ave, Middletown, NY 10940
$595,000 Sold Feb 04, 2026

26 Kyleigh Way, Middletown, NY 10940
- 4 Beds
- 3.5 Baths
- 2,188 Sq Ft
- Built 2020
Last Sold Summary
- 4% Below List Price
- $272/SF
- 182 Days On Market
Current Estimated Value $601,871

Last Listing Agent Delroy Smith List 4 Less Realty

26 Kyleigh Way, Middletown, NY 10940

Est $437,373 Not Listed For Sale

22 Nicole Place, Middletown, NY 10940
- 3 Beds
- 2 Baths
- 1,332 Sq Ft
- Built 1977
22 Nicole Place, Middletown, NY 10940

Last Sold Summary
- 11% Above List Price
- $297/SF
- 17 Days On Market
- Last Sold Price $395,000
- Aug 30, 2023
Last Listing Agent Alyse Toffel Keller Williams Hudson Valley

/15
$99,000
- Land
- 5.1 Acres
- $19,412 per Acre
Lot 11 Meadow Brook Dr, Middletown, NY 12455

Tucked away in the pastoral rolling hills, just a short drive from down town Margaretville, this very special 5 acre parcel is sure to check many boxes on your wish list. A peaceful and serene setting with beautiful scenic views and rolling open meadows backed by magical woods to explore. With several possible building sites this parcels offers what most are looking for. Easy access, and close to

Rosalie Glauser Listing by Frank Lumia Real Estate Plus!, LLC

Lot 11 Meadow Brook Dr, Middletown, NY 12455
/37
$4,500 Per Month
- 4 Beds
- 3 Baths
- 2,400 Sq Ft
- House for Rent
809 Highland Lake Rd, Middletown, NY 10940

Experience resort-style living in this exceptional luxury rental located in Middletown, NY and situated in the highly desirable Minisink Valley Central School District. This stunning home offers the perfect blend of upscale comfort, space, and incredible outdoor amenities. Inside, you’ll find 4 spacious bedrooms and 3 full bathrooms, along with high-end finishes and thoughtful upgrades

Victoria Wander Divine Realty NY, LLC

809 Highland Lake Rd, Middletown, NY 10940
$435,050 Sold May 30, 2025

26 Wilson St, Middletown, NY 10940
- 3 Beds
- 1.5 Baths
- 1,524 Sq Ft
- Built 1986
Last Sold Summary
- 1% Above List Price
- $285/SF
- 23 Days On Market
Current Estimated Value $446,801

Last Listing Agent Andrea Rose Keller Williams Hudson Valley

26 Wilson St, Middletown, NY 10940

Est $475,679 Not Listed For Sale

50 Nicole Place, Middletown, NY 10940
- 4 Beds
- 2 Baths
- 2,088 Sq Ft
- Built 1976
50 Nicole Place, Middletown, NY 10940

Last Sold Summary
- 19% Above List Price
- $192/SF
- 36 Days On Market
- Last Sold Price $400,000
- Dec 15, 2023
Last Listing Agent Rosalie Cook Weichert Realtors

/33
$419,000 Pending
- 3 Beds
- 1.5 Baths
- 1,984 Sq Ft
32 Dudley Ln, Middletown, NY 10940

All you need is a moving van! Move right into this beautifully renovated 3-bedroom Nantucket-style Colonial, ideally set on a quiet street. Features include a spacious, sun-filled kitchen with quartz countertops, tiled flooring, and oversized windows, a warm and inviting family room with a fireplace, and three generously sized bedrooms. Additional highlights include an attached garage and a

Naomi Streicher Q Home Sales

32 Dudley Ln, Middletown, NY 10940
/20
$1,750 Per Month
- 2 Beds
- 1 Bath
- 700 Sq Ft
- Apartment for Rent
19 Bloomingburg Rd, Middletown, NY 10940

Great Property for outdoor enjoyment. Freshly painted with new carpet. Private entrance on front of the building. Stairs to 2nd level, Spacious Kitchen & Living Room, Full bath with tub & shower, 1 Spacious & 1 Small Bedroom + stairs to storage above. Tenant pays electric, propane for heat and stove, and garbage removal. Additional Information: Amenities: Storage. Lease Term: Over 12 Months, 12

Margaret Williams Century 21 E & M Williams Rlty

19 Bloomingburg Rd, Middletown, NY 10940
$339,000 Sold Sep 17, 2025

847 Greenville Turnpike, Middletown, NY 10940
- 3 Beds
- 2 Baths
- 1,764 Sq Ft
- Built 1995
Last Sold Summary
- 46% Below List Price
- $192/SF
- 240 Days On Market
Current Estimated Value $396,662

Last Listing Agent Neven Spralja REALHome Services & Solutions

847 Greenville Turnpike, Middletown, NY 10940

Est $421,917 Not Listed For Sale

25 Karen Joy Dr, Middletown, NY 10940
- 3 Beds
- 2 Baths
- 2,080 Sq Ft
- Built 1978
25 Karen Joy Dr, Middletown, NY 10940

Last Sold Summary
- $202/SF
- 62 Days On Market
- Last Sold Price $420,000
- Nov 18, 2024
Last Listing Agent Yara Roussos Homes By Yara Realty Group LLC

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