Recently Sold Homes in Middletown, NY

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SOLD OCT 30, 2025

ABOUT THIS HOME
Recently Sold Home in Middletown, NY:
Set behind a beautiful wall of stone and down a winding driveway, this spacious cedar sided ranch, on 2 level acres of a picture book lawn flanked by specimen trees and mature landscaping. Gleaming hardwood flooring throughout, neutral colors, abundant sunlight and well apportioned rooms. 3 possible 4 bedrooms 3 baths and ample closet space. Huge eat in kitchen with stainless appliances. A full finishable basement running the entire footprint of the home. A huge entertainment sized deck, split ductless high efficiency air conditioning has been recently installed. A detached two car garage. Valley Central Schools, minutes to route 211 shopping and dining and NYC bus and rail transportation a

$600,000 Last sold price

3 beds2.5 baths2,340 sq ft

322 Union School Rd, Middletown, NY 10941

Listing by Howard Hanna Rand Realty

SOLD SEP 3, 2025

ABOUT THIS HOME
Recently Sold Home in Middletown, NY:
Welcome to 45 Birch Drive, a beautifully renovated and move-in-ready 3-bedroom, 1.5-bath townhouse offering modern updates, spacious living, and everyday comfort. Step inside to a bright and inviting layout updated lighting, and a flowing main level perfect for both relaxing and entertaining. The kitchen has been refreshed with modern appliances and custom cabinetry, offering style and functionality. Upstairs, you’ll find three generously sized bedrooms and a beautifully renovated full bathroom, along with a convenient updated half bath on the main floor. The private backyard patio creates a perfect outdoor retreat for morning coffee or evening gatherings. Additional features include

$341,000 Last sold price

3 beds1.5 baths1,540 sq ft

45 Birch Dr, Middletown, NY 10940

Listing by RE/MAX Benchmark Realty Group

SOLD SEP 5, 2025

ABOUT THIS HOME
Recently Sold Home in Middletown, NY:
Welcome to this fully renovated townhouse in Inwood Hills Condominiums. This Home is a first floor unit that has been completely renovated with two spacious bedrooms and one full bath. This is a one level home with an open family room and an open dining room with brand new flooring and lighting. The kitchen features new appliances and cabinets done less than a year ago. Masterbedrom has new flooring just put in with lighting as well. The bathroom was fully renovated with brand new vanity, toilet, and tub. Hookups installed for Washer and dryer. Right around the corner from Rt 17 and I-84, with shopping and restaurants close by. Additional Information: ParkingFeatures:2 Car Detached,

$199,000 Last sold price

2 beds1 bath940 sq ft

90 Inwood Rd, Middletown, NY 10941

Listing by BHHS Hudson Valley Properties

SOLD NOV 18, 2025

ABOUT THIS HOME
Recently Sold Home in Middletown, NY:
Come see this awesome completely udated unit , new kitchen with great looking cabinets and new flooring. Great view from the patio and a awning to keep out the sun. washer and dryer in the unit. No showings before 12 Noon

$220,000 Last sold price

1 bed1 bath830 sq ft

65 Sycamore Dr, Middletown, NY 10940

Listing by Howard Hanna Rand Realty

SOLD NOV 13, 2025

ABOUT THIS HOME
Recently Sold Home in Middletown, NY:
One-Level Living at It's Finest – First Floor Condo in Middletown, NY Welcome to effortless living in this beautifully maintained first-floor condo, located in the heart of Middletown, NY. This spacious unit features brand new hardwood floors throughout, offering a warm and modern feel from the moment you step inside. The primary bedroom features a generous walk-in closet and a private en-suite bath, creating a true owner’s retreat. The spacious second bedroom offers flexibility for guests, a home office, or additional living space. The home is equipped with a high-pressure toilet, central air, and a recently serviced boiler for comfort and efficiency. Additional highlights incl

$247,000 Last sold price

2 beds2 baths880 sq ft

215 Ruth Ct, Middletown, NY 10940

Listing by Keller Williams Realty

Property at 256 Concord Ln, Middletown, NY 10940, 2 beds, 2 baths

$235,000 Last sold price

2 beds2 baths1,000 sq ft

256 Concord Ln, Middletown, NY 10940

Listing by Keller Williams Hudson Valley

Property at 17 Old Anvil Ln, Middletown, NY 10940, 3 beds, 2.5 baths

$375,000 Last sold price

3 beds2.5 baths1,692 sq ft

17 Old Anvil Ln, Middletown, NY 10940

Listing by Keller Williams Hudson Valley

Property at 224 Concord Ln, Middletown, NY 10940, 2 beds, 1.5 baths

$190,000 Last sold price

2 beds1.5 baths924 sq ft

224 Concord Ln, Middletown, NY 10940

Listing by Keller Williams Hudson Valley

Property at 38 Brittany Dr, Middletown, NY 10940, 2 beds, 1 bath

$240,000 Last sold price

2 beds1 bath974 sq ft

38 Brittany Dr, Middletown, NY 10940

Listing by Keller Williams Realty

Property at 936 Tower Ridge Cir, Middletown, NY 10941, 2 beds, 2 baths

$314,900 Last sold price

2 beds2 baths1,216 sq ft

936 Tower Ridge Cir, Middletown, NY 10941

Listing by Keller Williams Realty

Property at 100 Hillside Dr Unit C15, Middletown, NY 10941, 2 beds, 2 baths

$274,000 Last sold price

2 beds2 baths1,012 sq ft

100 Hillside Dr Unit C15, Middletown, NY 10941

Listing by Howard Hanna Rand Realty

Property at 26 Sycamore Dr, Middletown, NY 10940, 2 beds, 1.5 baths

$335,000 Last sold price

2 beds1.5 baths1,340 sq ft

26 Sycamore Dr, Middletown, NY 10940

Listing by Keller Williams Hudson Valley

Property at 25 Jimal Dr, Middletown, NY 10940, 2 beds, 1 bath

$236,500 Last sold price

2 beds1 bath893 sq ft

25 Jimal Dr, Middletown, NY 10940

Listing by Real Estate Circuit Inc

Property at 122 W Main St, Middletown, NY 10940, 6 beds, 4 baths

$620,000 Last sold price

6 beds4 baths4,491 sq ft

122 W Main St, Middletown, NY 10940

Listing by Preferred Properties Real Esta

Property at 8 Badami Dr, Middletown, NY 10941, 5 beds, 1.5 baths

$515,000 Last sold price

5 beds1.5 baths2,526 sq ft

8 Badami Dr, Middletown, NY 10941

Listing by Howard Hanna Rand Realty

Property at 317 Wawayanda Ave, Middletown, NY 10940, 4 beds, 1 bath

$335,000 Last sold price

4 beds1 bath1,124 sq ft

317 Wawayanda Ave, Middletown, NY 10940

Listing by Hudson Valley Home Connection

Property at 268 Concord Ln, Middletown, NY 10940, 1 bed, 1 bath

$155,000 Last sold price

1 bed1 bath735 sq ft

268 Concord Ln, Middletown, NY 10940

Listing by Keller Williams Realty

Property at 23 Willow Pl, Middletown, NY 10940, 3 beds, 1 bath

$334,000 Last sold price

3 beds1 bath1,066 sq ft

23 Willow Pl, Middletown, NY 10940

Listing by Cronin & Company Real Estate

Property at 15 Rowan St #13, Middletown, NY 10940, 5 beds, 2 baths

$405,000 Last sold price

5 beds2 baths1,920 sq ft

15 Rowan St #13, Middletown, NY 10940

Listing by Keller Williams Realty

Property at 22 Maryland Ave, Middletown, NY 10940, 3 beds, 1 bath

$375,000 Last sold price

3 beds1 bath1,440 sq ft

22 Maryland Ave, Middletown, NY 10940

Listing by Picture It Sold, LLC

Property at 34 Jimal Dr, Middletown, NY 10940, 2 beds, 1.5 baths

$265,000 Last sold price

2 beds1.5 baths1,082 sq ft

34 Jimal Dr, Middletown, NY 10940

Listing by Keller Williams Hudson Valley

Property at 3 Kohler, Middletown, NY 10940, 3 beds, 1.5 baths

$425,000 Last sold price

3 beds1.5 baths1,920 sq ft

3 Kohler, Middletown, NY 10940

Listing by eXp Realty

Property at 55 Woodcrest Dr, Middletown, NY 10940, 1 bed, 1 bath

$110,000 Last sold price

1 bed1 bath585 sq ft

55 Woodcrest Dr, Middletown, NY 10940

Listing by Z Wisdom Realty Inc.

Property at 63 Pierson Hill Rd, Middletown, NY 10940, 2 beds, 1 bath

$270,000 Last sold price

2 beds1 bath896 sq ft

63 Pierson Hill Rd, Middletown, NY 10940

Listing by Absolute Real Estate of NY Inc

Property at 257 Tally Ho Rd, Middletown, NY 10940, 3 beds, 2 baths

$436,000 Last sold price

3 beds2 baths1,266 sq ft

257 Tally Ho Rd, Middletown, NY 10940

Listing by Eichner Realty Group Inc.

Property at 7 Ross Ln, Middletown, NY 10941, 4 beds, 2.5 baths

$496,000 Last sold price

4 beds2.5 baths2,000 sq ft

7 Ross Ln, Middletown, NY 10941

Listing by BHHS Hudson Valley Properties

Property at 14 Laddie Rd, Middletown, NY 10941, 3 beds, 2 baths

$440,001 Last sold price

3 beds2 baths1,702 sq ft

14 Laddie Rd, Middletown, NY 10941

Listing by Keller Williams Hudson Valley

Property at 129 Foster Rd, Middletown, NY 10941, 1 bed, 1 bath

$193,000 Last sold price

1 bed1 bath512 sq ft

129 Foster Rd, Middletown, NY 10941

Listing by Curasi Realty, Inc.

Property at 306 S Centerville Rd, Middletown, NY 10940, 4 beds, 2.5 baths

$580,000 Last sold price

4 beds2.5 baths2,633 sq ft

306 S Centerville Rd, Middletown, NY 10940

Listing by Keller Williams Realty Group

Property at 97 E Main St, Middletown, NY 10940, 2 beds

$180,000 Last sold price

2 beds— baths2,269 sq ft

97 E Main St, Middletown, NY 10940

Listing by Century 21 Alliance Rlty Group

Property at 21 Maple Dr, Middletown, NY 10940, 4 beds, 2 baths

$415,000 Last sold price

4 beds2 baths1,848 sq ft

21 Maple Dr, Middletown, NY 10940

Listing by Daf Realty

Property at 109 Lake Ave, Middletown, NY 10940, 2 beds, 2 baths

$315,000 Last sold price

2 beds2 baths920 sq ft

109 Lake Ave, Middletown, NY 10940

Listing by I Realty LLC

Property at 391 Scotchtown Collabar Rd, Middletown, NY 10941, 4 beds, 1.5 baths

$490,000 Last sold price

4 beds1.5 baths2,722 sq ft

391 Scotchtown Collabar Rd, Middletown, NY 10941

Listing by Howard Hanna Rand Realty

Property at 51 Howard Dr, Middletown, NY 10941, 4 beds, 2 baths

$400,000 Last sold price

4 beds2 baths1,408 sq ft

51 Howard Dr, Middletown, NY 10941

Listing by Keller Williams Hudson Valley

Property at 29 Beth Dr, Middletown, NY 10941, 4 beds, 2 baths

$330,000 Last sold price

4 beds2 baths1,716 sq ft

29 Beth Dr, Middletown, NY 10941

Listing by Keller Williams Hudson Valley

Property at 8 Red Oak Ct, Middletown, NY 10941, 4 beds, 3 baths

$575,000 Last sold price

4 beds3 baths2,916 sq ft

8 Red Oak Ct, Middletown, NY 10941

Listing by RE/MAX Benchmark Realty Group

Property at 193 Bert Crawford Rd, Middletown, NY 10940, 3 beds, 1 bath

$310,000 Last sold price

3 beds1 bath1,176 sq ft

193 Bert Crawford Rd, Middletown, NY 10940

Listing by Preferred Properties Real Esta

Property at 203 Highland Ave, Middletown, NY 10940, 8 beds, 4 baths

$650,000 Last sold price

8 beds4 baths5,533 sq ft

203 Highland Ave, Middletown, NY 10940

Listing by RE/MAX Benchmark Realty Group

Property at 55 Prince St, Middletown, NY 10940, 3 beds, 2 baths

$360,000 Last sold price

3 beds2 baths1,537 sq ft

55 Prince St, Middletown, NY 10940

Listing by BHHS Hudson Valley Properties

Property at 14 Briarwood Dr, Middletown, NY 10940, 3 beds, 2 baths

$440,000 Last sold price

3 beds2 baths2,558 sq ft

14 Briarwood Dr, Middletown, NY 10940

Listing by Cronin & Company Real Estate

Property at 138 Reinhardt Rd, Middletown, NY 10940, 3 beds, 2 baths

$478,500 Last sold price

3 beds2 baths2,542 sq ft

138 Reinhardt Rd, Middletown, NY 10940

Listing by Keller Williams Hudson Valley

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Based on information submitted to the MLS GRID as of Thu Nov 27 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Recently Sold Homes in Middletown

There are currently 191 recently sold homes for sale in Middletown at a median listing price of $374K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Middletown stay on the market for 57 days and receive 5 offers. Popular neighborhoods include Downtown, and Presidential Heights. This map is refreshed with the newest listings in Middletown every 15 minutes.

In the past month, 20 homes have been sold in Middletown. In addition to houses in Middletown, there were also 11 condos, 1 townhouse, and 11 multi-family units for sale in Middletown last month. Middletown is a moderately walkable city in New York with a Walk Score of 57. Middletown is home to approximately 27,394 people and 10,344 jobs. Find your dream home in Middletown using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Middletown are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Middletown. Our Middletown real estate stats and trends will give you more information about home buying and selling trends in Middletown. If you're looking to sell your home in the Middletown area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Middletown with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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