Homes with Pools for Sale in Montgomery, NY

17 homes

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ABOUT THIS HOME
Home with a Pool for sale in Montgomery, NY:
Set back on a commanding ridgeline along Route 52, this extraordinary 2007 custom estate seamlessly marries Hudson Valley scenic beauty with artistic, Southwestern-inspired elegance. Set across 5+ private acres with sweeping panoramic views of the Shawangunk Mountains, this home offers an architectural statement and a true lifestyle retreat. Step inside the striking foyer to discover warm organic textures, soaring ceiling heights, rich hardwood floors, and a floor-to-ceiling stone fireplace that anchors the main living area. Sunlight pours through expansive glass walls framing distant valley vistas, while custom barn doors, ironwork accents, and curated finishes add a distinct artistic flai

$974,000

5 beds3.5 baths4,730 sq ft

In-ground pool • Splash pool • Custom bar

1576 Route 52, Walden, NY 12586

Listing by Davis R Chant Real Estate Inc.

OPEN SUN, 11AM TO 1PM

ABOUT THIS HOME
Home with a Pool for sale in Montgomery, NY:
Welcome to a home designed for comfortable everyday living, memorable celebrations and making the most of every season. Built in 2017, this spacious four-bedroom residence offers room to gather, relax, work and entertain. The main level features warm hardwood floors, inviting formal living and dining rooms, and a beautifully appointed kitchen where everyone can come together. Granite countertops, a large center island, stainless-steel appliances, abundant cabinetry, a butler’s pantry and an additional pantry closet make meals and entertaining effortless. Upstairs, four generously sized bedrooms with impressive walk-in closets provide comfortable private retreats. The spacious primary

$729,999

4 beds2.5 baths2,454 sq ft

Firepit • Granite countertops • Butler pantry

392 Bailey Rd, Montgomery, NY 12549

Listing by Curasi Realty, Inc.

ABOUT THIS HOME
Home with a Pool for sale in Montgomery, NY:
Do you know what you can do with over 27 acres? Create the homestead you’ve always dreamed about! Spend weekends riding ATVs through your own private trail system. Grow your own food in the established 40’ x 40’ garden. Raise chickens in the 12’ x 12’ chicken coop with an expansive 12’ x 40’ run. Follow the trails approximately 10 acres into the property and disappear into the woods at your own developed campsite. Swim all summer in the 33-foot above-ground pool, sit beside a crackling fire all winter, and enjoy the kind of privacy that’s becoming harder and harder to find in Orange County. At 960 County Route 17, you don’t have to choos

$850,000

4 beds3 baths2,592 sq ft

Private trail system • Generous storage • Established garden

960 County Route 17, Montgomery, NY 12549

Listing by HVG Realty, Inc.

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Montgomery, NY:
Welcome to 3 Edmunds Lane in Walden! This spacious 4-bedroom raised ranch offers a flexible layout, plenty of living space and an outdoor setup made for enjoying the warmer months. The main level features comfortable living and dining areas, along with four bedrooms and plenty of opportunity to make the space your own. The lower level adds valuable additional finished space, perfect for a family room, home office, gym, playroom or entertaining area. Step outside and the backyard becomes the real showstopper. The in-ground pool creates your own private summer retreat, whether you’re hosting friends, relaxing by the water or just enjoying a quiet afternoon at home. Located on a neighbor

$439,000

4 beds1.5 baths1,582 sq ft

In-ground pool • Finished space • Flexible layout

3 Edmunds Ln, Walden, NY 12586

Listing by Hudson Valley Home Connection

ABOUT THIS HOME
Home with a Pool for sale in Montgomery, NY:
Full of classic character and versatility, this spacious home at 77 Union Street offers a fantastic opportunity in the Valley Central School District. The property features a spacious 3-bedroom main living area alongside a comfortable 1-bedroom secondary living space, ideal for a home office, guest suite, or additional flexible living arrangements. Classic architectural details include a charming gabled roofline, original wood siding, Victorian-style finishes, and a welcoming screened front porch, perfect for relaxing or entertaining. Inside, the home is filled with natural light and features built-in shelving throughout for added charm and storage. The main living area offers spacious room

$499,999

4 beds3 baths2,509 sq ft

Screened front porch • Built in shelving • Washer dryer hookup

77 Union St, Montgomery, NY 12549

Listing by Keller Williams Realty

Property at 35 Highland Ave, Walden, NY 12586, 2 beds, 1 bath

$399,999

2 beds1 bath1,180 sq ft

35 Highland Ave, Walden, NY 12586

Listing by Keller Williams Realty

Property at 342 Coldenham Rd, Walden, NY 12586, 3 beds, 1.5 baths

$429,900

3 beds1.5 baths1,276 sq ft

342 Coldenham Rd, Walden, NY 12586

Listing by Century 21 E & M Williams Rlty

Property at 171 Decker Dr, Walden, NY 12586, 4 beds, 2.5 baths

$549,000

4 beds2.5 baths2,095 sq ft

171 Decker Dr, Walden, NY 12586

Listing by Picture It Sold, LLC

Property at 165 Benedict Rd, Montgomery, NY 12549, 3 beds, 2.5 baths

$749,999

3 beds2.5 baths2,030 sq ft

165 Benedict Rd, Montgomery, NY 12549

Listing by Keller Williams Realty

Property at 102 W Wiley St, Maybrook, NY 12543, 4 beds, 3.5 baths

$350,000

4 beds3.5 baths3,658 sq ft

102 W Wiley St, Maybrook, NY 12543

Listing by eRealty Advisors, Inc

Property at 123 Collabar Rd, Montgomery, NY 12549, 3 beds, 3 baths

$2,700,000

3 beds3 baths2,669 sq ft

123 Collabar Rd, Montgomery, NY 12549

Listing by Ellis Sotheby's Intl Realty

Property at 45 Sunset Dr, Walden, NY 12586, 3 beds, 1 bath

$389,900

3 beds1 bath1,210 sq ft

45 Sunset Dr, Walden, NY 12586

Listing by Magic Of Great Neck Realty Inc

Property at 27 Grosso Ct, Montgomery, NY 12549, 4 beds, 3 baths

$724,000

4 beds3 baths3,300 sq ft

27 Grosso Ct, Montgomery, NY 12549

Listing by RE/MAX Distinguished Hms.&Prop

Property at 95 Judson Rd, Montgomery, NY 12549, 3 beds, 3 baths

$2,499,900

3 beds3 baths3,448 sq ft

95 Judson Rd, Montgomery, NY 12549

Listing by Howard Hanna Rand Realty

Property at 46 Pond Hill Ln, Walden, NY 12586, 2 beds, 2.5 baths

$390,000

2 beds2.5 baths1,576 sq ft

46 Pond Hill Ln, Walden, NY 12586

Listing by RPM Westchester

Property at 42 Philip Dr, Montgomery, NY 12549, 3 beds, 2.5 baths

$739,000

3 beds2.5 baths3,400 sq ft

42 Philip Dr, Montgomery, NY 12549

Listing by Houlihan Lawrence Inc.

Property at 198 Corbett Rd, Montgomery, NY 12549, 6 beds, 7.5 baths

$2,895,000

6 beds7.5 baths6,415 sq ft

198 Corbett Rd, Montgomery, NY 12549

Listing by Keller Williams Realty Liberty

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ABOUT THIS HOME
Home with a Pool for sale in Montgomery, NY:
This immaculate Ranch home in desirable Colden Park offers easy access to shopping, Route 84, the New York State Thruway, and Valley Central Schools. A major 1998 renovation added a beautiful Primary Bedroom with a walk-in shower and a stunning Family/Sunroom. Both spaces are warm and bright, featuring skylights and vaulted glass ceilings. The home provides an eat-in kitchen with stainless steel appliances, a large Dining Room, two additional bedrooms, and a Study/Den with a closet. The basement has paneled walls and includes a laundry room with side-by-side washer/dryers. There is an open patio at the rear of the home and an above ground 16’ new swimming pool with sun decking adjacen

$410,000

3 beds2 baths1,560 sq ft

Open patio • Eat-in kitchen • Primary bedroom

23 Windwood Dr, Newburgh, NY 12550

Listing by Alliance Realty

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Montgomery, NY:
Set on nearly an acre along a private road, this spacious Cape Cod offers a flexible layout, generous living space, and a completely private backyard. The main level features two large bedrooms and a full bathroom, making the floor plan convenient for a variety of living arrangements. The large kitchen offers granite countertops, an island with seating, and plenty of space for everyday meals and entertaining. A bright sunroom provides additional living space and overlooks the backyard and above-ground pool. Off the attached two-car garage, a spacious mudroom adds everyday functionality with a washer and dryer, abundant storage, and direct walk-out access to the backyard. Upstairs are two ad

$550,000

4 beds2.5 baths2,146 sq ft

Private road • Private backyard • Large kitchen

5 Libra Ln, Wallkill, NY 12589

Listing by Keller Williams Realty

ABOUT THIS HOME
Home with a Pool for sale in Montgomery, NY:
Nestled in the scenic countryside of Pine Bush, this inviting home at 135 Pirog Rd offers the perfect blend of privacy, comfort, and rural charm. Set on a peaceful property, this residence features spacious living areas, abundant natural light, and a warm, welcoming atmosphere throughout. The home offers a functional layout ideal for both everyday living and entertaining, with generously sized rooms and plenty of potential to make it your own. Enjoy the beauty of the surrounding landscape while still being conveniently located near local shops, schools, parks, and commuter routes. Whether you're seeking a full-time residence or a tranquil retreat, this property presents a wonderful opportun

$679,000

4 beds2.5 baths2,640 sq ft

Scenic countryside • Peaceful property • Parks

135 Pirog Rd, Pine Bush, NY 12566

Listing by Real Estate Circuit Inc

ABOUT THIS HOME
Home with a Pool for sale in Montgomery, NY:
Come to the connivence of a home that you can enjoy with all you can dream of and the Beautiful views and privacy of a back yard and the many seasons . There are no homes behind your home and a deck to come outside and sit on The luxury is it is close to the end of a call a sac. .This home is very tastefully decorated . Rooms are a very nice size for family and entertainment on the main level and a half bath . The upper leel features the bedrooms and two full bathrooms . there is plenty more to offer it is a must come and see.

$485,000

3 beds2.5 baths1,613 sq ft

Deck • No homes behind • End of a cul de sac

246 Orleans Rd Unit 10-2, Newburgh, NY 12550

Listing by Real Estate Connection Corp

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Montgomery, NY:
Beautiful, private, and tranquil Custom-Built Colonial in Mamakating, set on over eight acres and located in the Pine Bush School District. Meticulously maintained with attention to every single detail, this home is approached by a serene country road and surrounded by nature. The exterior features stone pavers and custom mahogany details, including columns, entrance ceiling, window trim, and front door. The main level offers a spacious living room with wood-burning stove, formal dining room, and adjacent den with sliders to the backyard patio. The kitchen features custom white oak and cherry cabinetry, abundant storage, granite countertops, stainless steel appliances, and a separate wine b

$669,000

3 beds2.5 baths2,006 sq ft

Wood-burning stove • Stone pavers • 8.41 acre lot

315 Walker Valley Rd, Pine Bush, NY 12566

Listing by Christie's Int. Real Estate

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Montgomery, NY:
Welcome to your new home in The Grove — a highly sought-after Condo Community in New Windsor, NY. This beautifully updated and maintained Townhouse provides an expansive floorplan covering 3 levels with 1,910 sq ft of living space including a Finished Basement. The Entryway opens right up to the open concept living area in the level above and down to the finished Basement below . Take in the gorgeous main floor with high ceilings and oversized windows that brightens the entire living room with natural lighting. The gorgeous hardwood floors continue into the formal Dining Area just off both the Living Room and the Kitchen creating a natural flow. The Kitchen features a waterfall Quartz

$485,000

3 beds2.5 baths1,910 sq ft

Quartz corner island • Glass sliding doors • Finished basement

806 Hawthorn Way, New Windsor, NY 12553

Listing by Howard Hanna Rand Realty

Property at 1113 Balsam Dr, New Windsor, NY 12553, 2 beds, 2.5 baths

$425,000

2 beds2.5 baths1,722 sq ft

1113 Balsam Dr, New Windsor, NY 12553

Listing by Hudson Premium Realty

Property at 34 Hawthorne Dr, Middletown, NY 10940, 4 beds, 3 baths

$579,000

4 beds3 baths2,368 sq ft

34 Hawthorne Dr, Middletown, NY 10940

Listing by Hudson Valley Griffith

Property at 10 Bainbridge Pl #704, Newburgh, NY 12550, 3 beds, 2.5 baths

$449,000

3 beds2.5 baths1,748 sq ft

10 Bainbridge Pl #704, Newburgh, NY 12550

Listing by Real Broker NY LLC

Property at 12 Brighton Dr #1404, Newburgh, NY 12550, 3 beds, 2.5 baths

$485,000

3 beds2.5 baths1,748 sq ft

12 Brighton Dr #1404, Newburgh, NY 12550

Listing by HomeSmart Homes & Estates

Property at 13 James Wilkinson Rd, Rock Tavern, NY 12575, 5 beds, 3.5 baths

$689,000

5 beds3.5 baths2,776 sq ft

13 James Wilkinson Rd, Rock Tavern, NY 12575

Listing by eXp Realty

Property at 80 Susan Ln, Circleville, NY 10919, 5 beds, 3.5 baths

$729,900

5 beds3.5 baths3,214 sq ft

80 Susan Ln, Circleville, NY 10919

Listing by Howard Hanna Rand Realty

Property at 26 Delaware Rd, Newburgh, NY 12550, 3 beds, 2 baths

$437,500

3 beds2 baths1,316 sq ft

26 Delaware Rd, Newburgh, NY 12550

Listing by RE/MAX Benchmark Realty Group

Property at 111 Jasmine Dr, Middletown, NY 10940, 2 beds, 2 baths

$505,000

2 beds2 baths1,473 sq ft

111 Jasmine Dr, Middletown, NY 10940

Listing by Coldwell Banker Choice Prop.

Property at 30 Banbury Way #1204, Newburgh, NY 12550, 3 beds, 2.5 baths

$459,000

3 beds2.5 baths1,830 sq ft

30 Banbury Way #1204, Newburgh, NY 12550

Listing by Keller Williams Realty

Property at 232 Maybrook Rd, Campbell Hall, NY 10916, 5 beds, 3.5 baths

$1,099,000

5 beds3.5 baths3,264 sq ft

232 Maybrook Rd, Campbell Hall, NY 10916

Listing by Keller Williams Realty

Property at 24 Beth Dr, Middletown, NY 10941, 3 beds, 2.5 baths

$525,000

3 beds2.5 baths1,952 sq ft

24 Beth Dr, Middletown, NY 10941

Listing by Howard Hanna Rand Realty

Property at 19 Brighton Dr #1702, Newburgh, NY 12550, 3 beds, 2.5 baths

$473,000

3 beds2.5 baths1,830 sq ft

19 Brighton Dr #1702, Newburgh, NY 12550

Listing by Howard Hanna Rand Realty

Property at 302 Lakeside Rd, Newburgh, NY 12550, 3 beds, 2.5 baths

$599,000

3 beds2.5 baths2,721 sq ft

302 Lakeside Rd, Newburgh, NY 12550

Listing by RE/MAX Benchmark Realty Group

Property at 2 Summerset Dr, Wallkill, NY 12589, 4 beds, 2.5 baths

$525,000

4 beds2.5 baths2,016 sq ft

2 Summerset Dr, Wallkill, NY 12589

Listing by eXp Realty

Based on information submitted to the MLS GRID as of Mon Sep 07 2026. 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.

Homes with Pools for Sale in Montgomery

There are currently 17 homes with pools for sale in Montgomery at a median listing price of $409K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Montgomery stay on the market for 44 days and receive 1 offers. This map is refreshed with the newest listings in Montgomery every 15 minutes.

In the past month, 3 homes have been sold in Montgomery. In addition to houses in Montgomery, there was also 1 condo, 1 townhouse, and 1 multi-family unit for sale in Montgomery last month. Find your dream home in Montgomery 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 Montgomery are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Montgomery. Our Montgomery real estate stats and trends will give you more information about home buying and selling trends in Montgomery. If you're looking to sell your home in the Montgomery area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Montgomery with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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