Downtown, NY homes for sale & real estate

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ABOUT THIS HOME
Downtown, NY Homes for Sale
BACK ON MARKET: Your Dream Home Awaits at 28 Spring St, Middletown. Don't let this second chance slip away. This beautiful, 4 bedroom, 2 bathroom home is back on the market. Previous buyer's financing fell through. This is an incredible opportunity for you to step right in and secure a truly remarkable property. The seller has invested in significant updates to make this home move-in ready. The inviting, open-concept layout is perfect for gathering and entertaining, all while retaining that highly desirable, classic charm. You simply can't beat this location. Situated right in the heart of Middletown, you'll have easy access to all the amenities you could ever need—shopping, restauran

$329,000

4 beds2 baths1,696 sq ft

28 Spring St, Middletown, NY 10940

Spacious backyard • Open-concept layout • 7,854 sq ft lot

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Downtown, NY Homes for Sale
Discover this renovated colonial home nestled in the charming city of Middletown. This spacious single-family residence offers a perfect blend of classic charm and tasteful updates. The main level features a dedicated home office, an inviting living room, and an open-concept kitchen with stunning granite countertops and a center island. A formal dining room and a convenient half bath complete this level. Upstairs, you'll find four comfortable bedrooms and two full bathrooms, providing ample space for guests. The partially completed attic offers additional versatile space or storage. Recent upgrades (2021) includes a new roof, furnace, water heater, siding, and freshly paved blacktop drivewa

$375,000

4 beds2.5 baths1,668 sq ft

29 Little Ave, Middletown, NY 10940

Open-concept kitchen • Granite countertops • Center island

Listing by Christie's Int. Real Estate

ABOUT THIS HOME
Downtown, NY Homes for Sale
Discover the potential in this charming 3-bedroom, 2-full-bath two-story home with 1,504 sq ft of living space. Full of character and solid construction, this property offers a formal dining room and plenty of room to grow with a full unfinished attic and full, unfinished, walk-out basement featuring washer/dryer hookups. Featuring strong bones and charming original touches, this home is brimming with potential. Its versatile indoor and outdoor spaces provide the perfect canvas for someone to call it home.

$319,999

3 beds2 baths1,504 sq ft

20 Benton Ave, Middletown, NY 10940

6,750 sq ft lot • Built 1913 • Listed 92 days

Listing by Keller Williams Realty

ABOUT THIS HOME
Downtown, NY Homes for Sale
Vacant and sold as-is. Inspections for informational purposes only. Prior buyer could not perform—property is back on market. Great investment or owner-occupied opportunity! Two-family home in an R-2 zone, ideal for rental income or living in one unit while renting the other. Features spacious layouts with a 3BR/1BA first-floor unit and 2BR/1BA second-floor unit. High-demand rental location within walking distance to Touro College, minutes to I-86 & I-84, Galleria Mall, Garnet Medical Center, shops, and restaurants. Major recent updates (City of Middletown approved). New sewer drain line, updated plumbing & water heater (March 2025), new 2nd-floor deck, updated gutters, po

$369,900

5 beds2 baths2,440 sq ft

44 Houston Ave, Middletown, NY 10940

2 family house • R-2 zone • Galleria mall

Listing by Keller Williams Hudson Valley

ABOUT THIS HOME
Downtown, NY Homes for Sale
Well maintained 3 bedrooms, 2 bathrooms mobile home in the Valley View mobile home community. Simple one level living, short distance from major highways and shops. Located in the Valley Central School District. Very easy to see. Call today for your own private tour.

$150,000

3 beds2 baths1,344 sq ft

551 5th Ave, Middletown, NY 10941

One level living • 2 parking spots • Built 1997

Listing by Keller Williams Hudson Valley

Property at 458 County Route 50, Middletown, NY 10940, 4 beds, 2.5 baths

$599,900

4 beds2.5 baths2,200 sq ft

458 County Route 50, Middletown, NY 10940

Listing by Keller Williams Hudson Valley

Property at Pocatello Road Pocatello Rd, Middletown, NY 12566

$45,000

— beds— baths— sq ft

Pocatello Road Pocatello Rd, Middletown, NY 12566

Listing by Howard Hanna Rand Realty

Property at 64 Seaman Rd, Middletown, NY 10941

$399,000

— beds— baths— sq ft

64 Seaman Rd, Middletown, NY 10941

Listing by HomeSmart Homes & Estates

Property at County Hwy 76, Middletown, NY 10940

$400,000

— beds— baths— sq ft

County Hwy 76, Middletown, NY 10940

Listing by Villa Group Real Estate LLC

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Nearby homes that match your criteria

ABOUT THIS HOME
Downtown, NY Homes for Sale
LOCATION, LOCATION, LOCATION! Don’t miss this charming 3 Bedroom, 1.5 Bathroom Two-Story Home located in the heart of Middletown and within the Middletown School District. This home offers unbeatable convenience—just minutes from local restaurants, shopping centers, banks, healthcare facilities, and postal services. Situated close to elementary and secondary schools, and just blocks from Orange County Community College and Morrison Lab School. Also nearby is Touro College and several beautiful parks for outdoor enjoyment. Commuters will love the quick access to major highways, including I-84—only a 10 to 15-minute drive away. And the location is just the beginning—st

$359,999

3 beds1.5 baths1,160 sq ft

5 Mills Ave, Middletown, NY 10940

4,134 sq ft lot • Built 1883 • Listed 140 days

Listing by Keller Williams Realty

ABOUT THIS HOME
Downtown, NY Homes for Sale
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 full bath and a home office/ den you will have all the space you need. Enjoy peace of mind with numerous recent improvements including updated siding (2024), a freshly paved blacktop driveway (2025), and all new flooring (2025). The beautiful, fully updated kitchen features stainless appliances—refrigerator, stove, and dishwasher! Washer and dryer are also included, along with two window

$220,000

2 beds1 bath820 sq ft

58 Wawayanda Ave, Middletown, NY 10940

Updated siding • Private backyard • New flooring

Listing by Cronin & Company Real Estate

ABOUT THIS HOME
Downtown, NY Homes for Sale
Welcome to 221 E Main St—a standout investment opportunity offering flexibility, location, and long-term potential in one of Orange County’s most active and rapidly growing markets. This mixed-use property features two residential units and a commercial space on the ground floor, making it an ideal choice for investors, owner-occupants, or entrepreneurs looking to establish a business while generating rental income. The upstairs level includes two well-maintained residential units, each offering bright, comfortable living with strong appeal to long-term tenants. The ground-floor commercial space provides excellent visibility along a well-trafficked stretch of East Main Street, m

$429,999

2 beds— baths2,946 sq ft

221 E Main St, Middletown, NY 10940

Excellent visibility • Easy access to i-84 • Commercial space

Listing by Century 21 Alliance Rlty Group

ABOUT THIS HOME
Downtown, NY Homes for Sale
* * 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!

$99,900

— beds— baths— sq ft

28 Genung St, Middletown, NY 10940

Multi-family unit • 0.28 acre lot • Listed 67 days

Listing by Weichert Realtors

Based on information submitted to the MLS GRID as of Sun Dec 21 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.

Average home prices near Downtown, NY

Cities

Downtown, NY real estate trends

$463K

Sale price

+41.7%
since last year

$215

Sale $/sq ft

-11.5%
since last year

Under list price

2.4%

Days on market

Down payment

12.5%

Total homes sold

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