Luxury homes for sale & real estate in Middletown, NY

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ABOUT THIS HOME
Luxury Home for sale in Middletown, NY:
Discover the allure of 89 sprawling acres in Orange County, New York, featuring a charming farm house and a tranquil pond. The farmhouse, with its rustic charm and scenic surroundings, holds immense potential as a delightful Airbnb destination or a mini vacation retreat. Its spacious interior, cozy ambiance, and proximity to nature make it an idea I spot for relaxation and rejuvenation.

$1,550,000

5 beds5.5 baths4,365 sq ft

79 Bisch Rd, Middletown, NY 10940

89 sprawling acres • Tranquil pond • Spacious interior

Listing by P R O Links Realty Inc

ABOUT THIS HOME
Luxury Home for sale in Middletown, NY:
Looking to Enjoy Life? Experience 535 Ct Rt 22 in the Minisink School District. Unique Handcrafted Home that is surrounded by Nature and Privacy. This Amazing property is backed up to a NYS Protected Conservation in addition to the existing 21 1/2 Acres of Privacy. Gorgeous Breath-taking views can be seen from almost every window of the home. Enjoy the Dramatic, Sundrenched, Eye Popping Open Floor Plan starting in the Great Room that offers stunning views of the Mountains, beautifully handcrafted beams, Recessed Lighting, Hand cut Stone wood burning fireplace. Dining Room large enough to entertain any dinner party. Designer Chef's Kitchen that any Chef would love cooking in. This very conve

$999,999

3 beds2.5 baths3,315 sq ft

535 County Route 22, Middletown, NY 10940

21.5 acre lot • Garage • Built 2022

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Luxury Home for sale in Middletown, NY:
Welcome to 346 Mullock Road – A Private Pondside Mini-Estate in the Heart of the Hudson Valley Tucked away down a long, tree-lined drive in the sought after Minisink Valley School District, this 3-bedroom, 3-bathroom contemporary sanctuary unfolds across 3300+ sqft of architecturally distinctive living space, set on 5.4 private, park-like acres with not one, but two spring-fed ponds teeming with bass, perch, catfish, and sunfish. The back pond is a hidden treasure—clay-lined and 15 feet deep with its own dock and sitting area, perfect for swimming, fishing, or ice-skating in the winter months. As you approach, the serenity begins. A teardrop circle driveway welcomes you to the o

$969,999

3 beds3 baths3,282 sq ft

346 Mullock Rd, Middletown, NY 10940

5.4 acre lot • 2 garage spots • Built 1999

Listing by Keller Williams Hudson Valley

ABOUT THIS HOME
Luxury Home for sale in Middletown, NY:
Enter the gates of this grand estate, where you'll find a stunning 5-bedroom, 5-bathroom home spanning 4,200 square feet, complete with a large barn and a natural pond, all set on 36.8 acres. This private estate is located in Middletown, NY, nestled among rolling pastures, tranquil woods, and your very own pond. The expansive property also features a two-story post-and-beam barn with horse stalls, wells, and an additional hay barn for storage. The original Colonial estate, built in 1821, serves as the main house. Enjoy horseback riding on your own property, or take advantage of the many recreational activities available, such as farming, hunting, snowmobiling, four-wheeling, and fishing. Wi

$975,000

5 beds4.5 baths4,200 sq ft

255 Howells Rd, Middletown, NY 10940

Two story barn • Tranquil woods • Natural pond

Listing by Keller Williams Hudson Valley

ABOUT THIS HOME
Luxury Home for sale in Middletown, NY:
Colonial Masterpiece - This one-of-a-kind Hudson Valley residence artfully combines authentic, historic character with flawless contemporary design set on a bucolic, level parcel. The c. 1790’s antique colonial portion of the home features a timeless natural stone facade, standing seam roof, and welcoming red front door evoking true period charm. An architecturally inspired contemporary wing clad in cedar was added in the 1980s, creating a spacious, chic, light-filled interior, and a seamless blend of old and new. The property is punctuated outside with towering pines and mature, perennial plantings. The antique portion of the home maintains beamed ceilings and crafted wood details in

$1,100,000

4 beds3 baths2,787 sq ft

441 Scotchtown Collabar Rd, Middletown, NY 10941

0.8 acre lot • 2 garage spots • Pool

Listing by Ellis Sotheby's Intl Realty

Property at 3 Bristol Dr, Middletown, NY 10941, 5 beds, 8 baths

$1,799,000

5 beds8 baths7,794 sq ft

3 Bristol Dr, Middletown, NY 10941

Listing by All American Realty Management

Property at 285 Hill Rd, Middletown, NY 10940, 5 beds, 4.5 baths

$2,999,999

5 beds4.5 baths6,460 sq ft

285 Hill Rd, Middletown, NY 10940

Listing by Reliable Realty Group

Property at 565 Prosperous Valley Rd, Middletown, NY 10940, 4 beds, 2.5 baths

$1,600,000

4 beds2.5 baths4,000 sq ft

565 Prosperous Valley Rd, Middletown, NY 10940

Listing by Real Estate Circuit Inc

Property at Shawangunk Rd, Wallkill, NY 10941

$1,499,000

— beds— baths— sq ft

Shawangunk Rd, Wallkill, NY 10941

Listing by McGrath Realty Inc

$8,900,000

— beds— baths— sq ft

Maples Rd, Middletown, NY

Listing by First Hampton Int'l Realty LLC

Property at 422 M And M Rd, Middletown, NY 10940

$1,200,000

— beds— baths— sq ft

422 M And M Rd, Middletown, NY 10940

Listing by eXp Realty

Property at Hill Rd, Scotchtown, NY 10941

$1,100,000

— beds— baths— sq ft

Hill Rd, Scotchtown, NY 10941

Listing by All American Realty Management

Property at Shawangunk Rd, Wallkill, NY 10940

$2,300,000

— beds— baths— sq ft

Shawangunk Rd, Wallkill, NY 10940

Listing by Howard Hanna Rand Realty

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ABOUT THIS HOME
Luxury Home for sale in Middletown, NY:
Welcome home to a hidden Hudson Valley gem: a stunning 8,100+ sq. ft. estate set on 5 private acres, just minutes from the Village of Goshen and only 55 minutes from NYC. This gorgeous home boasts 10 bedrooms and 6 bathrooms, all which have been beautifully updated. This meticulously restored 1907 estate blends historic craftsmanship with modern luxury. Featuring geothermal heating & central air, new plumbing and baths, updated insulation, a newer roof with 50-year warranty, and restored masonry and woodwork throughout. The home offers multiple grand living spaces including a sunroom, game room, library, and an elegant formal dining room. The chef’s kitchen boasts a quartz islan

$2,495,000

10 beds5.5 baths6,090 sq ft

157 Arcadia Rd, Goshen, NY 10924

New plumbing • Restored masonry • Newer roof

Listing by Iron Valley RE Tri-State

ABOUT THIS HOME
Luxury Home for sale in Middletown, NY:
Your Hudson Valley haven—an escape that feels like home. Just 2.6 miles from the Campbell Hall Metro-North train station to NYC, exclusive enclave living awaits in the sought-after neighborhood of Dorian Farms Estates, where every day is perfectly framed by sweeping Shawangunk Mountain vistas, rolling pastures, picturesque equestrian farmland, and fiery Hudson Valley sunsets in the coveted Town of Hamptonburgh. This breathtaking Contemporary residence on 2.1 acres spans an impressive 5,276 square feet of thoughtfully designed living space and exquisite architectural detail throughout. From the moment you arrive, the home makes a lasting impression. A grand two-story foyer with soaring

$1,299,000

4 beds3.5 baths3,776 sq ft

11 Dorian Way, Campbell Hall, NY 10916

Hudson valley views • Gourmet kitchen • Custom mahogany bar

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Luxury Home for sale in Middletown, NY:
Bloomingburg Farmhouse set on 42.8 Acres - RAG 1 Zoning Ideal for Residential Development - Home is Approx. 2535 Square foot with 3 Bedrooms and 3 1/2 baths - Full basement with finished rec room. There are 3 Old barns (1900's era) on property and an older machine shed in fair condition. Solar panels installed in 2016. Buildings are close to road and the land has nice fields and woods. Adjacent to Village of Bloomingburg. Ideal for possible housing development. Well pump and pressure tank replaced this year. On deemand hot water (gas). Buyers to do their own due dilligence regarding zoning and development in the Town of Mamakating.

$5,000,000

3 beds3.5 baths2,535 sq ft

171 Winterton Rd, Bloomingburg, NY 12721

Finished rec room • Older machine shed • 3 old barns

Listing by Rieber Realty Inc

ABOUT THIS HOME
Luxury Home for sale in Middletown, NY:
COLONIAL HOME BUILT 1860 WITH UPDATES OVER THE YEARS, ALSO PICTURE-PERFECT SETTING OF 96 ACRES OF CONSERVATION RESTRICTED LAND, WITH COMMERICAL TYPE KITCHEN SET UP IN ADDITIONAL BUILDING, ALSO INCLUDED IS A TENANT HOUSE FOR RENTAL, OLD DAIRY BARN AND OTHER SMALL BUILDING, PROPERTY GREAT FOR GENTLEMAN FARM OR WEEKEND HOME, GREAT FEILDS FOR CROPS OR HORSES, DEED RESCIRTIONS SCENIC VEIW BEAUTIFUL SETTING GREAT LOCATION NEAR ROUTE 17 & I 84 WALKING DISTANCE TO COUNTY HERTIGE TRAIL, CHAMING HOME WITH MANY OLD TIMES ORGINALS, FEATURE 4.5 BATHS, WALK UP PART ATTIC, CENTER HALL

$1,750,000

7 beds4.5 baths3,000 sq ft

212 Cheechunk Rd, Goshen, NY 10924

Old dairy barn • 96 acre lot • Built 1860

Listing by RE/MAX Benchmark Realty Group

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Middletown, NY:
Beautiful new construction being built in Ridgebury Estates, a new community of carefully crafted colonials perched high on a hill with tree-lined streets, stone walls and lots of open space. Situated in the heart of Orange County, NY and in the highly sought-after Minisink Valley School District. Discover the perfect blend of elegance and function in The Caraway II, a thoughtfully designed home featuring four spacious bedrooms, 2.5 bathrooms, and a layout ideal for today’s lifestyle. Step inside to find rich red hardwood floors throughout the main level, along with central A/C and a cozy fireplace that anchors the family room—perfect for relaxing evenings. The open-concept kitc

$862,900

4 beds2.5 baths3,422 sq ft

Lot #26 Azalea Ln, Slate Hill, NY 10973

Open space • New construction • Central a/c

Listing by Realty Promotions Inc

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Middletown, NY:
Beautiful new construction being built in Ridgebury Estates, a new community of carefully crafted colonials perched high on a hill with tree-lined streets, stone walls and lots of open space. Situated in the heart of Orange County, NY and in the highly sought-after Minisink Valley School District. The Winston, a beautifully crafted home offering four bedrooms, 2.5 bathrooms, and a layout designed for both everyday comfort and effortless entertaining. The first floor features an inviting open-concept living room, dining room, and kitchen, creating a seamless flow filled with natural light. Sliding glass doors lead to a back deck, perfect for outdoor dining or relaxing. The gourmet kitchen is

$868,900

4 beds2.5 baths3,438 sq ft

Lot #18 Bee Blossom Ct, Slate Hill, NY 10973

Quartz countertops • New construction • Tiled backsplash

Listing by Realty Promotions Inc

Property at Lot #17 Bee Blossum Ct, Slate Hill, NY 10973, 4 beds, 2.5 baths

$862,900

4 beds2.5 baths3,422 sq ft

Lot #17 Bee Blossum Ct, Slate Hill, NY 10973

Listing by Realty Promotions Inc

Property at Lot #9 Azalea Ln, Slate Hill, NY 10973, 4 beds, 2.5 baths

$868,900

4 beds2.5 baths3,438 sq ft

Lot #9 Azalea Ln, Slate Hill, NY 10973

Listing by Realty Promotions Inc

Property at 7 Angelas Way, Goshen, NY 10924, 4 beds, 2.5 baths

$850,000

4 beds2.5 baths3,309 sq ft

7 Angelas Way, Goshen, NY 10924

Listing by RE/MAX Town & Country

Property at 14 Robalene Dr, Goshen, NY 10924, 6 beds, 4 baths

$979,900

6 beds4 baths2,600 sq ft

14 Robalene Dr, Goshen, NY 10924

Listing by Owner Entry.com

Property at 37-39 Main St, Chester, NY 10918, 4 beds, 4 baths

$1,498,888

4 beds4 baths7,308 sq ft

37-39 Main St, Chester, NY 10918

Listing by eXp Realty

Property at 158 Brown Rd, Westtown, NY 10998, 4 beds, 3.5 baths

$2,999,999

4 beds3.5 baths5,919 sq ft

158 Brown Rd, Westtown, NY 10998

Listing by K. Fortuna Realty, Inc.

Property at 53 Odyssey Dr, Chester, NY 10918, 4 beds, 3.5 baths

$1,100,000

4 beds3.5 baths4,467 sq ft

53 Odyssey Dr, Chester, NY 10918

Listing by Howard Hanna Rand Realty

Property at 247 Sarah Wells Trl, Campbell Hall, NY 10916, 6 beds, 3.5 baths

$3,370,000

6 beds3.5 baths3,618 sq ft

247 Sarah Wells Trl, Campbell Hall, NY 10916

Listing by Werner Realty of New York

Property at 395 Sarah Wells Trl, Goshen, NY 10924, 6 beds, 5.5 baths

$1,925,000

6 beds5.5 baths5,450 sq ft

395 Sarah Wells Trl, Goshen, NY 10924

Listing by Howard Hanna Rand Realty

Property at 294 Comfort Trl, Montgomery, NY 12549, 3 beds, 2 baths

$974,999

3 beds2 baths1,796 sq ft

294 Comfort Trl, Montgomery, NY 12549

Listing by Keller Williams Realty

Property at 4 Distribution Dr, Bloomingburg, NY 12721

$1,600,000

— beds— baths— sq ft

4 Distribution Dr, Bloomingburg, NY 12721

Listing by MK Realty Inc

Property at Chandler Ln, Montgomery, NY 12549

$1,999,999

— beds— baths— sq ft

Chandler Ln, Montgomery, NY 12549

Listing by MS Realty Group USA, Inc

Property at 117 Hamptonburgh Rd, Campbell Hall, NY 10916

$1,100,000

— beds— baths— sq ft

117 Hamptonburgh Rd, Campbell Hall, NY 10916

Listing by Howard Hanna Rand Realty

Property at South Rd, Wurtsboro, NY 12790

$900,000

— beds— baths— sq ft

South Rd, Wurtsboro, NY 12790

Listing by eXp Realty

Based on information submitted to the MLS GRID as of Sun Nov 30 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.

Luxury Homes for Sale in Middletown

There are currently 13 luxury 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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