Homes with Pools for Sale in Litchfield County, CT

114 homes

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FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
CANAAN VALLEY HOME WITH POOL & STUDIO Indulge in Litchfield County luxury at this homestead, proudly situated in Canaan Valley, offering picturesque views of fields from both the front and back of this 4-Bedroom, 3-Bath residence, plus a Studio with its own Half Bath. This property features a spacious single-level living home, a separate studio, and an inground pool. The home has undergone comprehensive updates, presenting a modern and welcoming interior supported by robust system and structural enhancements, which include: well, septic, roof, siding, and heating and cooling systems, automatic generator. The inviting interior harmoniously blends indoor and outdoor spaces, ensuring a s

$1,135,000

4 beds3.5 baths2,460 sq ft

35 Emmons Ln, Canaan, CT 06018

Modern interior • Inground pool • Separate studio

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
Set on an extraordinary 12.81-acre parcel, this one-of-a-kind estate offers a rare blend of privacy, luxury, and architectural distinction. Fully renovated from top to bottom, the home showcases exceptional craftsmanship with high-end, custom finishes and a design unlike anything you've seen before. Step inside to the main level where soaring ceilings, exposed beams, and walls of glass fill the great room with natural light, anchored by a striking fireplace. The stunning custom kitchen is both functional and beautiful, seamlessly connecting to the dining area-perfect for everyday living or entertaining. A unique lofted office space overlooks the main living area, adding character and versat

$1,245,000

2 beds3 baths3,144 sq ft

142 Stilson Hill Rd, New Milford, CT 06776

Custom kitchen • Fully renovated • Built-in sauna

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
Nestled in the peaceful countryside of Goshen, this exceptional ranch-style estate offers the perfect blend of luxury, privacy, and functionality on more than 12 scenic acres. Featuring 3 spacious bedrooms and 3 full baths, the home is designed for comfortable single-level living with expansive views of the surrounding rural landscape. Step outside to your private resort-style retreat with a heated in-ground pool, relaxing hot tub, and dramatic waterfall feature, all set beneath a covered patio ideal for entertaining year-round. Whether hosting guests or enjoying quiet evenings outdoors, this space delivers a true vacation-at-home experience. Car enthusiasts, hobbyists, and business owners

$2,395,000

3 beds3 baths1,840 sq ft

80 Holmes Rd, Goshen, CT 06756

12.61 acre lot • 11 garage spots • Pool

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
Hidden Estate at High Street: A private Litchfield County retreat offering relaxed country living with exceptional versatility. This secluded country estate features fantastic outdoor spaces, 5 bedrooms, 6 baths, 12x24 salt water fountained pool, pool house and 2 studio apartments. Boasting 4,291 sq ft on 3.69 acres, this secluded oasis is the perfect hideaway to relax and refresh. The heart of the home is the oversized sunlit kitchen complete with granite breakfast bar, 6 burner stove, wall oven, dishwasher and double refrigerators. Kitchen is open to dining room and huge family room with sliders to pool area. There is also a formal living room w/ granite fireplace. Upstairs consists of 4

$800,000

4 beds4.5 baths5,729 sq ft

341 High St Ext, Thomaston, CT 06787

Pool house • Private retreat • 3.69 acre lot

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
Live Stress-Free in This Income-Producing Equestrian Retreat! Enjoy the best of country living while generating income from your property. Rental revenue from a separate 1 BR apartment and 4 of the 10 horse stalls offers a rare opportunity to offset ownership costs! Situated on 5.76 level acres of open pasture and riding space, this equestrian property is ideal for horse enthusiasts, trainers, or anyone seeking a peaceful rural lifestyle. The horse facilities include 4 barns with a total of 10 stalls, 2 wash stalls, and a 20 x 60-meter riding arena with premium stone dust and sand footing. The grounds offer ample space for turnout, training, recreation, and relaxation, creating the perfect

$819,000

3 beds2 baths2,448 sq ft

92 Minortown Rd, Woodbury, CT 06798

Horse facilities • 2 wash stalls • 5.76 level acres

Property at 380 Southbury Rd, CT 06783, 4 beds, 4.5 baths

$1,495,000

4 beds4.5 baths6,444 sq ft

380 Southbury Rd

BHHS Hudson Valley Properties

Property at 35 River Rd, Sharon, CT 06069, 7 beds, 6.5 baths

$1,950,000

7 beds6.5 baths3,141 sq ft

35 River Rd, Sharon, CT 06069

Property at 18 Tunnel Rd, Roxbury, CT 06783, 3 beds, 2.5 baths

$995,000

3 beds2.5 baths2,080 sq ft

18 Tunnel Rd, Roxbury, CT 06783

Property at 55 Good Hill Rd, Woodbury, CT 06798, 4 beds, 4.5 baths

$1,790,000

4 beds4.5 baths3,324 sq ft

55 Good Hill Rd, Woodbury, CT 06798

Property at 17 Woodbury Hl #17, Woodbury, CT 06798, 2 beds, 2.5 baths

$529,900

2 beds2.5 baths1,673 sq ft

17 Woodbury Hl #17, Woodbury, CT 06798

Property at 552 Twin Lakes Rd, Salisbury, CT 06068, 3 beds, 4 baths

$1,495,000

3 beds4 baths4,442 sq ft

552 Twin Lakes Rd, Salisbury, CT 06068

Property at 130 Sharon Mountain Rd, Sharon, CT 06069, 4 beds, 4 baths

$1,700,000

4 beds4 baths3,905 sq ft

130 Sharon Mountain Rd, Sharon, CT 06069

Property at 7 Cooper Hill Rd, Salisbury, CT 06068, 3 beds, 2.5 baths

$2,145,000

3 beds2.5 baths3,933 sq ft

7 Cooper Hill Rd, Salisbury, CT 06068

Property at 36 Deer Run Ln, Goshen, CT 06756, 3 beds, 4 baths

$1,250,000

3 beds4 baths4,009 sq ft

36 Deer Run Ln, Goshen, CT 06756

Property at 220 Painter Hill Rd, Roxbury, CT 06783, 4 beds, 4.5 baths

$2,750,000

4 beds4.5 baths4,570 sq ft

220 Painter Hill Rd, Roxbury, CT 06783

Property at 197 Skyline Ridge Rd, Bridgewater, CT 06752, 4 beds, 3.5 baths

$1,495,000

4 beds3.5 baths2,453 sq ft

197 Skyline Ridge Rd, Bridgewater, CT 06752

Property at 23 Mauwee Brook Rd, Kent, CT 06757, 4 beds, 5.5 baths

$5,500,000

4 beds5.5 baths5,400 sq ft

23 Mauwee Brook Rd, Kent, CT 06757

Property at 102 Melius Rd, Call Listing Agent, CT 06754-1503, 7 beds, 6 baths

$7,400,000

7 beds6 baths6,844 sq ft

102 Melius Rd, Call Listing Agent, CT 06754-1503

Houlihan Lawrence Inc.

Property at 62-64 Big Bear Hill Rd, New Milford, CT 06776, 6 beds, 8 baths

$8,200,000

6 beds8 baths8,457 sq ft

62-64 Big Bear Hill Rd, New Milford, CT 06776

Property at 87 Canaan Rd Unit 3F, Salisbury, CT 06068, 2 beds, 2.5 baths

$550,000

2 beds2.5 baths1,344 sq ft

87 Canaan Rd Unit 3F, Salisbury, CT 06068

Property at 394 Winchester Rd, Norfolk, CT 06058, 2 beds, 2.5 baths

$850,000

2 beds2.5 baths1,946 sq ft

394 Winchester Rd, Norfolk, CT 06058

Property at 476 Evergreen Rd, Torrington, CT 06790, 3 beds, 2.5 baths

$265,000

3 beds2.5 baths1,584 sq ft

476 Evergreen Rd, Torrington, CT 06790

Property at 19 Hemlock Ln, Salisbury, CT 06068, 3 beds, 2.5 baths

$1,950,000

3 beds2.5 baths3,777 sq ft

19 Hemlock Ln, Salisbury, CT 06068

Property at 207 Ledge Dr, Torrington, CT 06790, 2 beds, 2 baths

$205,000

2 beds2 baths1,154 sq ft

207 Ledge Dr, Torrington, CT 06790

Property at 406 Wells Hill Rd, Lakeville, CT 06039, 6 beds, 6.5 baths

$8,875,000

6 beds6.5 baths8,334 sq ft

406 Wells Hill Rd, Lakeville, CT 06039

Property at 197 A Tinker Hill Rd, New Preston Marble Dale, CT 06777, 6 beds, 7 baths

$7,950,000

6 beds7 baths8,650 sq ft

197 A Tinker Hill Rd, New Preston Marble Dale, CT 06777

Property at 47 Squire Rd, Roxbury, CT 06783, 5 beds, 5.5 baths

$3,995,000

5 beds5.5 baths7,121 sq ft

47 Squire Rd, Roxbury, CT 06783

Property at 394 Trailsend Dr, Torrington, CT 06790, 3 beds, 2 baths

$225,000

3 beds2 baths1,612 sq ft

394 Trailsend Dr, Torrington, CT 06790

Property at 184 Fern Ave, Litchfield, CT 06759, 8 beds, 9.5 baths

$3,950,000

8 beds9.5 baths10,516 sq ft

184 Fern Ave, Litchfield, CT 06759

Property at 373 Trailsend Dr, Torrington, CT 06790, 3 beds, 2 baths

$229,000

3 beds2 baths1,410 sq ft

373 Trailsend Dr, Torrington, CT 06790

Property at 305 Cliffside Dr, Torrington, CT 06790, 4 beds, 3.5 baths

$350,000

4 beds3.5 baths3,184 sq ft

305 Cliffside Dr, Torrington, CT 06790

Property at 389 Trailsend Dr, Torrington, CT 06790, 3 beds, 2.5 baths

$225,000

3 beds2.5 baths1,584 sq ft

389 Trailsend Dr, Torrington, CT 06790

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Based on information submitted to the MLS GRID as of Sat Aug 29 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 Litchfield County

There are currently 114 homes with pools for sale in Litchfield County at a median listing price of $490K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Litchfield County stay on the market for 51 days and receive 1 offers. This map is refreshed with the newest listings in Litchfield County every 15 minutes.

In the past month, 265 homes have been sold in Litchfield County. In addition to houses in Litchfield County, there were also 150 condos, 0 townhouses, and 62 multi-family units for sale in Litchfield County last month. Find your dream home in Litchfield County 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 Litchfield County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Litchfield County. If you're looking to sell your home in the Litchfield County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Litchfield County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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