Homes with Pools for Sale in Lewisboro, NY

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ABOUT THIS HOME
Home with a Pool for sale in Lewisboro, NY:
A truly special country estate awaits its next chapter. Set back on a circular driveway and nestled on more than 8 level acres, this Georgian Colonial offers an opportunity to make a remarkable property your very own. An elegant two-story entry features a curved staircase, transom and clerestory windows. The 4-bedroom, 4 1/2-bath home lives like a 5-bedroom, features oversized rooms, high ceilings and beautiful proportions. Three fireplaces, a paneled library, French doors, wide-plank floors, handsome millwork and pocket doors with brass hardware reflect the home's timeless character. A country eat-in kitchen with terracotta floors, exposed beams and a cozy lounging area anchored by a firep

$1,899,000

4 beds4.5 baths5,666 sq ft

292 Smith Ridge Rd, South Salem, NY 10590

Two-story entry • Curved staircase • Paneled library

Listing by William Raveis-New York LLC

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Lewisboro, NY:
Imagine coming home to a beautifully updated studio loft in Oakridge Condos. From the moment you enter, soaring cathedral ceilings, rich hardwood floors, and abundant natural light create an inviting sense of space. The stunning living room is anchored by a Carrara marble fireplace with a custom mantel, complemented by elegant chair rail and picture frame moldings. Just beyond, a private balcony offers a peaceful retreat. The spacious kitchen is designed to impress, featuring stainless steel appliances, diamond quartz countertops, and pendant lighting above a welcoming peninsula dining area. Above the main living space, an expansive loft with picturesque lake/pond views offers endless possi

$349,000

Studio1 bath986 sq ft

225 Lakeside Dr, South Salem, NY 10590

Updated studio loft • Lake views • Private balcony

Listing by Redfin Real Estate

ABOUT THIS HOME
Home with a Pool for sale in Lewisboro, NY:
Set high on 2.94 landscaped acres in South Salem, This home is a distinctive Yates Colonial that feels equally suited to everyday life as it does to a weekend country getaway. Freshly painted inside and out, the home retains the unique architectural character that makes it memorable. A cedar shingle multidimensional roofline, custom copper-topped turret, shaker shingle siding and a welcoming covered front porch. The dramatic two-story foyer sets the tone with a guest closet & half bath. A graceful staircase with newly installed runner & landing carpeting ascends within the turret with large windows leading to a large open second-floor landing overlooking the entry. This space c

$1,495,000

5 beds4 baths3,266 sq ft

195 Kitchawan Rd, South Salem, NY 10590

Covered front porch • Landscaped acres • Two-story foyer

Listing by Houlihan Lawrence Inc.

OPEN SAT, 1PM TO 4PMFLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Lewisboro, NY:
Welcome to this exceptional end-unit home, where thoughtful design, beautiful surroundings, and effortless indoor-outdoor living come together. From the moment you step onto the covered front porch, you’ll appreciate the privacy and tranquility of the surrounding woodland. Inside, the inviting entry opens to gleaming hardwood floors, elegant architectural details, and soaring ceilings that create a bright and spacious atmosphere. At the heart of the home, the well-appointed kitchen offers abundant cabinetry, generous counter space, and a functional layout ideal for everyday cooking and entertaining. The kitchen flows seamlessly into the living room, with both spaces offering direct ac

$767,000

2 beds2.5 baths2,200 sq ft

15 Guilford Cir, Goldens Bridge, NY 10526

Covered front porch • End-unit home • 2,943 sq ft lot

Listing by William Raveis-New York LLC

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Lewisboro, NY:
Gorgeous, updated, two bedroom townhome that lives like a three bedroom! The light-filled, living area features a wood-burning fireplace and flows seamlessly into the recently renovated large eat-in kitchen. Perfect for entertaining, the kitchen boasts stainless steel appliances, an oversized center island, and sliders to the deck. The main level also includes a spacious primary suite with an en-suite bath, a second bedroom, a full hall bath, and laundry. A newly installed main staircase leads to the upper level, where you'll find a versatile loft/den space and a skylit office with a door and a closet, providing flexible space for work or guests. Updates completed within the past few years

$599,000

2 beds2 baths1,468 sq ft

230 Lakeside Dr, South Salem, NY 10590

Skylit office • Open loft • Eat in kitchen

Listing by Coldwell Banker Realty

Property at 2 Tommys Ln, South Salem, NY 10590, 4 beds, 4 baths

$1,398,000

4 beds4 baths3,326 sq ft

2 Tommys Ln, South Salem, NY 10590

Listing by Compass Greater NY, LLC

Property at 137 Boway Rd, South Salem, NY 10590, 3 beds, 4.5 baths

$1,999,000

3 beds4.5 baths2,812 sq ft

137 Boway Rd, South Salem, NY 10590

Listing by Ginnel Real Estate

Property at 127 Boutonville Rd, Pound Ridge, NY 10576, 4 beds, 4.5 baths

$2,500,000

4 beds4.5 baths5,575 sq ft

127 Boutonville Rd, Pound Ridge, NY 10576

Listing by Serhant LLC

Property at 23 Briar Ct, Cross River, NY 10518, 1 bed, 1.5 baths

$575,000

1 bed1.5 baths1,451 sq ft

23 Briar Ct, Cross River, NY 10518

Listing by William Raveis-New York LLC

Property at 157 Jay Ct, Cross River, NY 10518, 1 bed, 1.5 baths

$529,000

1 bed1.5 baths1,451 sq ft

157 Jay Ct, Cross River, NY 10518

Listing by William Raveis-New York LLC

Property at 45 Pine Hill Dr, South Salem, NY 10590, 4 beds, 4.5 baths

$4,395,000

4 beds4.5 baths6,161 sq ft

45 Pine Hill Dr, South Salem, NY 10590

Listing by Compass Greater NY, LLC

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OPEN SAT, 1PM TO 3PMFLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Lewisboro, CT:
Enjoy the feel of a private country estate on more than three acres in western Ridgefield. Beautifully remodeled and enhanced by extensive additions by Heritage Homes in 2004, this distinctive home offers abundant sunlight throughout, generous living spaces, exceptional indoor and outdoor entertaining areas, and versatile outbuildings. The designer kitchen welcomes with beautiful finishes and thoughtful appointments, complemented by a flexible bonus room just beyond. A spacious sunken dining room features French doors leading to a stone terrace, while the inviting octagonal sunroom offers a bright retreat overlooking the grounds. The expansive primary suite addition is beautifully appointed

$1,779,000

4 beds4 baths5,373 sq ft

218 Old West Mountain Rd, Ridgefield, CT 06877

Designer kitchen • Flexible bonus room • Stone terrace

OPEN SAT, 1PM TO 3PM

ABOUT THIS HOME
Home with a Pool for sale in Lewisboro, CT:
Enjoy the best of Ridgefield living at Casagmo! Just a short stroll to historic Main Street, with its charming shops, diverse dining options, and popular concerts in the park, this desirable condominium community offers an exceptional combination of convenience and amenities, including a clubhouse, swimming pool, and tennis courts. This spacious upper-level freshly painted end unit features soaring vaulted ceilings, an abundance of natural light, and a flexible floor plan offering three bedrooms or two bedrooms plus a den or home office with two full baths. Step outside onto the private 5' x 14' deck and enjoy a peaceful setting overlooking a picturesque waterfall and lush greenery. Adding

$435,000

3 beds2 baths1,435 sq ft

33 Olcott Way #33, Ridgefield, CT 06877

Private deck • Swimming pool • Tennis courts

NEW 13 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Lewisboro, NY:
CALLING ALL CONTRACTORS AND INVESTORS – this is a complete renovation opportunity. This well-maintained complex offers fantastic amenities, including an outdoor pool, picnic area and playground, making it ideal for relaxation and recreation. This unit includes one assigned outdoor parking space and access to laundry facilities within the building. CALLING ALL CONTRACTORS AND INVESTORS – this is a complete renovation project and is priced accordingly. Three-bedroom units are very rare to come to market in these buildings, so rather than renovate an existing unit, you can design and construct this exactly as you choose! It is conveniently located close to train to NYC, shops, and

$249,000

3 beds2 baths1,200 sq ft

60 Barker St #617, Mount Kisco, NY 10549

Outdoor pool • Close to restaurants • Close to shops

Listing by Coldwell Banker Realty

NEW 21 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Lewisboro, NY:
Rarely available terrace unit that has been renovated! This amazing 4th floor unit is ready for you to just move in with an updated Kitchen and Bathroom and a balcony in the highly desirable Bedford Plaza complex. Located in the trendy town of Mount Kisco that boasts great restaurants, shopping, parks and a Metro North Train Station, 60 Barker is just a short stroll to all. A large community pool, BBQ area, playground and fitness center are some of the amenities that make this home truly special.

$170,000

1 bed1 bath800 sq ft

60 Barker St #420, Mount Kisco, NY 10549

Fitness center • Community pool • Balcony

Listing by Houlihan Lawrence Inc.

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Lewisboro, NY:
Welcome to the Willows! Spacious 2 Bedroom, 2.5 Bath End Unit with a 1 car garage. Features include an inviting Living Room with a fireplace, recessed lights and a sliding glass door to the patio, bright Eat-in Kitchen with a bay window and pass thru to the Dining Area, Primary Bedroom with a Full Bath and 2 closets, Basement Rec Room includes laundry, mechanicals and storage, stand up attic with storage shelves, central air, covered front porch and more! Willows Townhouse Community offers a pool, tennis courts, playground and a picturesque pond just a short walk away! Convenient location - minutes to schools, shopping, Reis Park, Metro North train and highways. Taxes do not include STAR ex

$559,000

2 beds2.5 baths1,397 sq ft

7 Krystal Dr, Somers, NY 10589

Covered front porch • Basement rec room • Eat-in kitchen

Listing by Land & Homes Realty Corp.

ABOUT THIS HOME
Home with a Pool for sale in Lewisboro, NY:
Move-in ready this refreshed one-level one-bedroom offers some of the easiest living Foxwood has to offer. No steps, abundant parking in front, private deck and no upstairs neighbor! All new kitchen appliances, including a five-burner gas range, dishwasher and refrigerator, fresh paint throughout, new carpeting, young A/C, and a new ceiling fan mean the work is already done. In-unit laundry adds daily convenience, and a storage unit downstairs provides extra room to spread out. With heat, hot water, and sewer included in the common charges, the numbers make as much sense as the lifestyle. Enjoy Foxwood’s in-ground pool, clubhouse, and picnic grounds close to home, plus quick ac

$386,000

1 bed1 bath768 sq ft

10 Foxwood Cir, Mount Kisco, NY 10549

Private deck • Clubhouse • In unit laundry

Listing by Houlihan Lawrence Inc.

Property at 126 Mclain St, Bedford Corners, NY 10549, 5 beds, 5.5 baths

$3,595,000

5 beds5.5 baths5,516 sq ft

126 Mclain St, Bedford Corners, NY 10549

Listing by eXp Realty

Property at 6 Theal Ct, Somers, NY 10589, 4 beds, 3.5 baths

$1,375,000

4 beds3.5 baths5,002 sq ft

6 Theal Ct, Somers, NY 10589

Listing by Coldwell Banker Realty

Property at 100 Woodcrest Ln #130, Mount Kisco, NY 10549, 2 beds, 2 baths

$575,000

2 beds2 baths1,445 sq ft

100 Woodcrest Ln #130, Mount Kisco, NY 10549

Listing by Coldwell Banker Realty

Property at 311 S Bald Hill Rd, New Canaan, CT 06840, 6 beds, 7.5 baths

$4,295,000

6 beds7.5 baths6,529 sq ft

311 S Bald Hill Rd, New Canaan, CT 06840

Property at 60 Krystal Dr, Somers, NY 10589, 2 beds, 1.5 baths

$549,000

2 beds1.5 baths1,995 sq ft

60 Krystal Dr, Somers, NY 10589

Listing by Berkshire Hathaway HS NY Prop

Property at 80 Krystal Dr, Somers, NY 10589, 2 beds, 2 baths

$499,000

2 beds2 baths1,144 sq ft

80 Krystal Dr, Somers, NY 10589

Listing by RE/MAX Prestige Properties

Property at 9 Lawson Ln #9, Ridgefield, CT 06877, 2 beds, 2.5 baths

$489,000

2 beds2.5 baths1,400 sq ft

9 Lawson Ln #9, Ridgefield, CT 06877

Property at 351 Wilton Rd W, Ridgefield, CT 06877, 5 beds, 6 baths

$2,295,000

5 beds6 baths5,410 sq ft

351 Wilton Rd W, Ridgefield, CT 06877

Property at 422 Mt Holly Rd, Katonah, NY 10536, 6 beds, 3.5 baths

$7,900,000

6 beds3.5 baths5,053 sq ft

422 Mt Holly Rd, Katonah, NY 10536

Listing by Houlihan Lawrence Inc.

Property at 140 Vista Rd, Wilton, CT 06897, 1 bed, 2 baths

$1,050,000

1 bed2 baths2,560 sq ft

140 Vista Rd, Wilton, CT 06897

Property at 496 Haines Rd, Bedford Corners, NY 10549, 5 beds, 6.5 baths

$4,900,000

5 beds6.5 baths7,213 sq ft

496 Haines Rd, Bedford Corners, NY 10549

Listing by Compass Greater NY, LLC

Property at 593 Heritage Hills Dr Unit C, Somers, NY 10589, 1 bed, 1.5 baths

$497,000

1 bed1.5 baths967 sq ft

593 Heritage Hills Dr Unit C, Somers, NY 10589

Listing by Houlihan Lawrence Inc.

Property at 116 Davids Way, Bedford Hills, NY 10507, 5 beds, 4.5 baths

$2,750,000

5 beds4.5 baths5,660 sq ft

116 Davids Way, Bedford Hills, NY 10507

Listing by Coldwell Banker Realty

Property at 121 Cedar Ln, Ridgefield, CT 06877, 4 beds, 6.5 baths

$1,998,500

4 beds6.5 baths5,207 sq ft

121 Cedar Ln, Ridgefield, CT 06877

Based on information submitted to the MLS GRID as of Fri Oct 23 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 Lewisboro

There are currently 11 homes with pools for sale in Lewisboro at a median listing price of $899K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Lewisboro stay on the market for 34 days and receive 1 offers. Popular neighborhoods include Bedford, and The Meadows at Cross River Condominiums. This map is refreshed with the newest listings in Lewisboro every 15 minutes.

In the past month, 20 homes have been sold in Lewisboro. In addition to houses in Lewisboro, there were also 7 condos, 1 townhouse, and 1 multi-family unit for sale in Lewisboro last month. Find your dream home in Lewisboro 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 Lewisboro are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Lewisboro. Our Lewisboro real estate stats and trends will give you more information about home buying and selling trends in Lewisboro. If you're looking to sell your home in the Lewisboro area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Lewisboro with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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