Homes with Pools for Sale in Highland, NY

10 homes

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Highland, NY:
Welcome to this beautifully updated 3-bedroom, 1.5 bath townhome in the heart of Highland, offering comfort, privacy, and a truly move-in-ready experience. Ideally situated at one of the most desirable locations within the complex, this home offers a warm and private setting while remaining conveniently close to everything Highland has to offer. The main level features a spacious living room, convenient half bath, and an inviting kitchen and dining area with expanded cabinetry, new appliances, pantry, and laundry tucked neatly away. Recent updates include new wood flooring and carpeting, fresh paint, and a beautifully updated upstairs bathroom vanity. Upstairs, you’ll find three brigh

$315,000

3 beds1.5 baths1,160 sq ft

7 Sunny Brook Cir, Highland, NY 12528

Expanded cabinetry • New appliances • Private fenced yard

Listing by Inspire Realty

ABOUT THIS HOME
Home with a Pool for sale in Highland, NY:
Your private Highland retreat is here, offering generous indoor and outdoor living space in a peaceful setting surrounded by mature trees and natural rock formations. Set back from the road, 124 Lily Lake Road features 4 bedrooms, 2 full baths, 2,592 square feet of flexible living space, extensive recent improvements, and an exceptional collection of spaces for relaxing, entertaining, working, and pursuing your favorite hobbies. Step inside to a bright, open interior enhanced by fresh paint, luxury vinyl plank flooring, recessed lighting, and oversized windows that bring in abundant natural light and views of the surrounding landscape. The spacious main living area provides plenty of room t

$635,000

4 beds2 baths2,592 sq ft

124 Lily Lake Rd, Highland, NY 12528

Large center island • New interior paint • 2.1 acre lot

Listing by Legacy Land & Homes LLC

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Highland, NY:
Relax into the comforts of home in this meticulously renovated and maintained mid-century ranch. Stone facing and a mix of painted brickwork and hardiboard in a neutral palette create a calming, natural exterior. Thoughtful landscaping accentuates the flow of the property, from the hydrangeas flanking the bluestone front porch to the pergola-covered pea stone patio, around the stone garden wall to the fire-pit on the back lawn, and finally up to the sunny, terraced pollinator gardens surrounding the heated in-ground pool. Steps from the pool, the three-season porch offers shade and a place to rest and relax, while close to the action. Through the dutch-door, bamboo floors and clean lines se

$625,000

3 beds2 baths2,000 sq ft

17 Amato Ln, Highland, NY 12528

Fire pit • Stone facing • 0.56 acre lot

Listing by Church Street Realty Services

ABOUT THIS HOME
Home with a Pool for sale in Highland, NY:
Tucked along a quiet dead-end street in Highland, this inviting three-bedroom, two-bath home offers nearly 1,600 square feet of thoughtfully updated living space, along with the kind of backyard that makes summer feel like a vacation at home. The bright main level has an easy, comfortable flow, with hardwood floors, a spacious living room and a beautifully renovated kitchen featuring generous cabinetry, granite countertops, stainless steel appliances and a patterned tile backsplash. Both full baths have also been renovated, allowing the next owner to settle in, making 7 Tina Dr. move in ready. The finished lower level expands the possibilities, offering a relaxed second living area anchored

$499,000

3 beds2 baths1,580 sq ft

7 Tina Dr, Highland, NY 12528

Brick fireplace • Renovated kitchen • Inground pool

Listing by Compass Greater NY, LLC

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Highland, NY:
Location , lifestyle, and effortless living come together in this beautifully reimagined two bedroom, one-and-a-half-bath townhouse. Thoughtfully remodeled with major updates completed within the last three years, this turnkey home features an updated eat-in kitchen with granite countertops and stainless steel appliances, an open dining area, a spacious primary bedroom with a walk-in closet, and a versatile second floor loft ideal for a home office, gym or sitting area. Enjoy the private back patio, community pool, and low maintenance living. Ideally located near the rail trail, town amenities, and approximately 4 miles from Poughkeepsie Metro-North station, offering convenient access to Ne

$310,000

2 beds1.5 baths1,120 sq ft

107 Vista Dr, Highland, NY 12528

Community pool • Private back patio • Quiet neighborhood

Listing by Hudson Dwellings Realty

Property at 188 Sterling Pl, Highland, NY 12528, 2 beds, 2.5 baths

$359,900

2 beds2.5 baths1,396 sq ft

188 Sterling Pl, Highland, NY 12528

Listing by Realty Center Hudson Valley

Property at 142 Hawleys Corners Rd, Highland, NY 12528, 5 beds, 3.5 baths

$799,000

5 beds3.5 baths3,824 sq ft

142 Hawleys Corners Rd, Highland, NY 12528

Listing by eXp Realty

Property at 76 Sunny Brook Cir, Highland, NY 12528, 2 beds, 1 bath

$279,000

2 beds1 bath1,056 sq ft

76 Sunny Brook Cir, Highland, NY 12528

Listing by BHHS Hudson Valley Properties

Property at 10 Eisgruber Park Ln, Highland, NY 12528, 3 beds, 2.5 baths

$674,900

3 beds2.5 baths2,144 sq ft

10 Eisgruber Park Ln, Highland, NY 12528

Listing by KW MidHudson

Property at 239-241 Fosler Rd, Highland, NY 12528, 5 beds, 5 baths

$799,000

5 beds5 baths— sq ft

239-241 Fosler Rd, Highland, NY 12528

Listing by Neighborhood Assistance Corp

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

OPEN SAT, 1PM TO 4PMFLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Highland, NY:
Don’t miss out on this beautifully refreshed, move-in-ready Colonial in the heart of Wappingers Falls! This sun-drenched home features 4 spacious bedrooms and 4 bathrooms (2 full, 2 half), all perfectly updated with fresh, neutral paint throughout. The primary suite serves as your own private retreat, complete with a beautifully renovated bathroom. For extra space, look no further than the fully finished basement, perfect for a gym, playroom, or home theater. Step outside to discover a true backyard oasis, featuring a pristine heated pool designed for ultimate relaxation. Ideally located just minutes from top schools and local shopping, this property is a rare find. Exclusive Buyer B

$595,000

4 beds3 baths1,960 sq ft

1 Merrywood Rd, Wappingers Falls, NY 12590

Renovated bathroom • Top schools • Backyard oasis

Listing by Keller Williams Hudson Valley

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Highland, NY:
Welcome to easy one-level living at Beechwood South Condominiums! This beautifully renovated 2-bedroom, 1-bath Garden style condo is bright and spacious for comfortable everyday living. All freshly painted, new bath, kitchen/stainless steel appliances & quality vinyl flooring. Both bedrooms are generously sized, and with no steps into the unit, everything is conveniently accessible on one level. During the warmer months, enjoy the community in-ground pool. The monthly HOA includes heat, hot water, water/sewer, garbage, grounds maintenance, pool service, mowing and snow removal. This pet-friendly complex is conveniently located just off Route 9, minutes from shopping, restaurants, hosp

$199,000

2 beds1 bath840 sq ft

2710 South Rd Unit A5, Poughkeepsie, NY 12601

Pet friendly complex • One level living • In ground pool

Listing by BHHS Hudson Valley Properties

ABOUT THIS HOME
Home with a Pool for sale in Highland, NY:
Welcome to Executive Towers, one of Poughkeepsie's distinctive high-rise cooperative communities, where comfortable low maintenance living meets convenience and Hudson Valley charm. This well-positioned residence offers an opportunity to enjoy the ease of co-op living in a full-service building just minutes from shopping, dining, colleges, hospitals, transportation, the Hudson River waterfront, and all that downtown Poughkeepsie has to offer.

$148,000

1 bed1 bath900 sq ft

160 Academy St Unit 2J, Poughkeepsie, NY 12601

Parking • Community pool • Built 1970

Listing by Inspire Realty

ABOUT THIS HOME
Home with a Pool for sale in Highland, NY:
Super Location and Maintenance free living is here! Spacious 1 bedroom, 1 and a half bathroom Co-Op unit. Ample large closets. Beautiful hardwood floors through-out. One level, ranch style. A one of a kind high rise Co-Op Building, well maintained units, grounds and building. Beautiful main entrance and foyer with front desk concierge and front door man service. Building has multiple elevators and emergency staircases. HOA fee is monthly. Private secure gated parking lot on premises. Pool with Patios and Life Guard. Laundry rooms and trash rooms on every floor, super convenient. There is an on-site superintendent lives in building. First Floor has Club Roo and Full mail room. Private back

$179,000

1 bed1.5 baths700 sq ft

160 Academy St Unit 3L, Poughkeepsie, NY 12601

Ample large closets • Community pool • Built 1974

Listing by K. Fortuna Realty, Inc.

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Highland, NY:
So much private and authentic space with this towering contemporary set back on over 7 elegant acres, an in-ground pool enhanced with generous decking and a lovely, electrified pool cabana for relaxing and escaping the sun. This is vintage single level living at its best with over 2000 square feet of living space but there is a fun library loft above the living room as well. As you enter the hidden driveway, you will feel like you are entering a refined modern estate. The approach is so elegant and the neighborhood is pastoral bliss. If you are looking for a late Mid-Century Modern home to make your own, this is an amazing opportunity for you. Very little cosmetic updating has been done sin

$499,000

3 beds1.5 baths2,112 sq ft

33 Reservoir Rd, Marlboro, NY 12542

3 season room • Hidden driveway • In ground pool

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Highland, NY:
Some houses have a presence you feel immediately. This one has a little modern-day Brady Bunch energy, nostalgic in all the right ways, but sleeker, more sophisticated, and undeniably cool. Set in one of the established neighborhoods originally developed during Poughkeepsie's IBM era, the custom brick exterior, strong architectural lines, vaulted interiors, and incredible backyard give this home a personality all its own. Inside, the scale is immediately apparent. Three bedrooms, two living rooms, a dedicated office, and a finished lower level create a house with room to actually live. The open kitchen connects directly to the most dramatic room in the house, where vaulted, beamed ceilings

$905,000

3 beds3 baths3,360 sq ft

3 Gus Siko Rd, Poughkeepsie, NY 12601

Beamed ceilings • Incredible backyard • Vaulted interiors

Listing by Compass Greater NY, LLC

Property at 6 Hope Ln, Milton, NY 12547, 4 beds, 2.5 baths

$499,900

4 beds2.5 baths1,876 sq ft

6 Hope Ln, Milton, NY 12547

Listing by KW Hudson Valley North

Property at 2 Enderkill Dr, Staatsburg, NY 12580, 3 beds, 3 baths

$450,000

3 beds3 baths1,514 sq ft

2 Enderkill Dr, Staatsburg, NY 12580

Listing by eXp Realty

Property at 105 Orchard St, Tillson, NY 12486, 4 beds, 2 baths

$525,000

4 beds2 baths2,010 sq ft

105 Orchard St, Tillson, NY 12486

Listing by Howard Hanna Rand Realty

Property at 38 Hurlihe St Unit 38B, Poughkeepsie, NY 12601, 1 bed, 1 bath

$325,000

1 bed1 bath833 sq ft

38 Hurlihe St Unit 38B, Poughkeepsie, NY 12601

Listing by Houlihan Lawrence Inc.

Property at 24 Robyn Dr, Marlboro, NY 12542, 3 beds, 2.5 baths

$645,500

3 beds2.5 baths2,232 sq ft

24 Robyn Dr, Marlboro, NY 12542

Listing by BHHS Hudson Valley Properties

Property at 36 Greentree Ln, Milton, NY 12547, 4 beds, 3.5 baths

$949,000

4 beds3.5 baths2,782 sq ft

36 Greentree Ln, Milton, NY 12547

Listing by Cornerstone Realty Group LLC

Property at 308 Bridgeview Dr, Poughkeepsie, NY 12601, 2 beds, 2.5 baths

$489,000

2 beds2.5 baths2,163 sq ft

308 Bridgeview Dr, Poughkeepsie, NY 12601

Listing by HomeSmart Homes & Estates

Property at 5 Anna Pl, Marlboro, NY 12542, 3 beds, 2.5 baths

$648,000

3 beds2.5 baths2,167 sq ft

5 Anna Pl, Marlboro, NY 12542

Listing by RE/MAX Benchmark Realty Group

Property at 18 Flower Hill Rd, Poughkeepsie, NY 12603, 3 beds, 2 baths

$525,000

3 beds2 baths1,821 sq ft

18 Flower Hill Rd, Poughkeepsie, NY 12603

Listing by BHHS Hudson Valley Properties

Property at 160 Academy St Unit 3P, Poughkeepsie, NY 12601, 1 bed, 1 bath

$100,000

1 bed1 bath650 sq ft

160 Academy St Unit 3P, Poughkeepsie, NY 12601

Listing by Epique Realty

Property at 506 Southview Dr, Poughkeepsie, NY 12601, 2 beds, 2.5 baths

$495,000

2 beds2.5 baths1,955 sq ft

506 Southview Dr, Poughkeepsie, NY 12601

Listing by United RE Hudson Valley Edge

Property at 5012 Albany Post, Staatsburg, NY 12580, 3 beds, 2 baths

$949,000

3 beds2 baths2,100 sq ft

5012 Albany Post, Staatsburg, NY 12580

Listing by Owner Entry.com

Property at 2740 South Rd Unit A2, Poughkeepsie, NY 12601, 2 beds, 1.5 baths

$240,000

2 beds1.5 baths1,000 sq ft

2740 South Rd Unit A2, Poughkeepsie, NY 12601

Listing by K. Fortuna Realty, Inc.

Property at 67 Academy St, Poughkeepsie, NY 12601, 6 beds, 6 baths

$675,000

6 beds6 baths3,744 sq ft

67 Academy St, Poughkeepsie, NY 12601

Listing by Century 21 Hudson Valley Rlty.

Based on information submitted to the MLS GRID as of Tue Oct 13 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 Highland

There are currently 10 homes with pools for sale in Highland at a median listing price of $429K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Highland stay on the market for 89 days and receive 3 offers. Popular neighborhoods include Waterfront, Waterfront District, and Mount Carmel Historic District. This map is refreshed with the newest listings in Highland every 15 minutes.

In the past month, 4 homes have been sold in Highland. In addition to houses in Highland, there were also 6 condos, 1 townhouse, and 4 multi-family units for sale in Highland last month. Find your dream home in Highland 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 Highland are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Highland. Our Highland real estate stats and trends will give you more information about home buying and selling trends in Highland. If you're looking to sell your home in the Highland area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Highland with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Highland, NY

Nearby Cities

Zip Codes

Neighborhoods

Nearby Cities with Homes with Pools

Nearby Neighborhoods with Homes with Pools

More to explore in Highland, NY

How to buy a house in Highland, NY

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Buy the right home at the right price near Highland with a local Redfin real estate agent.

Popular Markets in New York

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.