Homes with Pools for Sale in Litchfield County, CT

154 homes

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OPEN SUN, 11AM TO 1PM

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
Step into the timeless charm of this classic 1950s Cape Cod, ideally located just minutes from the historic Litchfield Green, local restaurants, and beautifully curated shops. Lovingly maintained by the same well loved Litchfield family for decades, this special home is ready to begin its next chapter. Featuring four bedrooms and two full baths, the home offers a wonderful opportunity to bring your own decorating vision to life. Rich wood paneling, warm wood floors, and built-in bookcases surround the traditional brick fireplace in the living room, creating a cozy and welcoming gathering space. The dining room opens through sliders to the back deck, overlooking the private in-ground pool pe

$425,000

4 beds2 baths2,110 sq ft

290 Torrington Rd, Litchfield, CT 06759

Rich wood paneling • Built-in bookcases • 0.6 acre lot

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
A PRIVATE BACKYARD OASIS AWAITS AT 49 DEERWOOD DRIVE. Set on a level, beautifully landscaped property, this inviting home offers an exceptional blend of classic character, comfortable living, and resort-like outdoor enjoyment. Mature gardens and landscaping surround the patio, charming gazebo, and in-ground pool, creating a truly special setting for summer gatherings, quiet mornings, and effortless entertaining. Inside, warm oak floors and thoughtful details add timeless appeal. The living room features a gas fireplace, while the family room is anchored by a wood-burning fireplace surrounded by built-ins and bookshelves, with sliders opening directly to the rear yard. Pocket doors add an el

$725,000

4 beds3 baths2,890 sq ft

49 Deerwood Dr, Bethlehem, CT 06751

Mature gardens • In-ground pool • Charming gazebo

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
Tired of cookie cutter homes? Super unique Contemporary with open layout/soaring ceilings and lots of custom features. 3 car attached garage and 1 bay built for RV with high ceilings and septic cleanout connection below. Vaulted/2 story livng room and gameroom with dry bar and foyer. Family room with fireplace. Light and bright kitchen with island. Main level bedroom/den with access to full bath. Impressive primary suite with balcony for mornng coffee and long winter mountain views plus huge bath and walk in closet. Lots of storage. Hardwood floors. Central air. Newly finished lower level has huge media room, plus execise room and office with bathroom. Lots of deck space for entertaining. A

$765,000

4 beds4.5 baths4,794 sq ft

41 McNulty Dr, New Milford, CT 06776

Custom features • Rv bay • Attached garage

OPEN SUN, 2PM TO 3:30PMFLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
Charming Country Home with Exceptional Barn-Inspired Great Room Located on a quiet dead end road in central Roxbury, this charming home is enhanced by a spectacular great room addition crafted by master barn builder Ed Cady, creating a warm & distinctive gathering space with extraordinary character. The great room features an enormous walk-in stone fireplace w/ propane starter, soaring ceilings w/ hand-hewn beams, & beautiful wide-board floors. The inviting kitchen opens to a cozy sitting room & addl dining area, creating an easy flow for everyday living & entertaining. Upstairs, the spacious primary suite is a private retreat, complete with vaulted ceilings, a genero

$1,895,000

4 beds4 baths5,232 sq ft

51 Rocky Mountain Rd, Roxbury, CT 06783

Wide board floors • Juliet walkway • Cozy sitting room

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
At the heart of this property is a beautifully preserved antique farmhouse offering 5 bedrooms and 3.5 baths, where historic character meets thoughtful modern updates. Wide-board floors and 5 fireplaces create a warm and inviting atmosphere. The spacious chef's kitchen features a large center island, breakfast nook, and dedicated coffee station. Open dining and living rooms are anchored by large hearth fireplaces, while a private office/study provides a quiet workspace. A spectacular 1,500-square-foot primary suite addition offers a luxurious private retreat, complete with a generous walk-in closet, soaking tub with views, double vanities, and heated floors. 3 laundry rooms (each equipped w

$1,995,000

5 beds2.5 baths3,971 sq ft

83 Thomson Rd, Bethlehem, CT 06751

Breakfast nook • Large center island • Antique farmhouse

Property at 107 Clark Rd, Litchfield, CT 06759, 6 beds, 4.5 baths

$1,673,000

6 beds4.5 baths3,034 sq ft

107 Clark Rd, Litchfield, CT 06759

Property at 10 Prospect Mountain Rd, Salisbury, CT 06068, 4 beds, 2.5 baths

$1,050,000

4 beds2.5 baths2,538 sq ft

10 Prospect Mountain Rd, Salisbury, CT 06068

Property at 336 South St, Roxbury, CT 06783, 4 beds, 2.5 baths

$998,000

4 beds2.5 baths2,556 sq ft

336 South St, Roxbury, CT 06783

Property at 27 Danvers Rd, New Milford, CT 06776, 4 beds, 2.5 baths

$590,000

4 beds2.5 baths2,755 sq ft

27 Danvers Rd, New Milford, CT 06776

Property at 2 Pomperaug Rd, Woodbury, CT 06798, 3 beds, 2.5 baths

$875,000

3 beds2.5 baths2,480 sq ft

2 Pomperaug Rd, Woodbury, CT 06798

Property at 48 Preston Ln, Salisbury, CT 06068, 2 beds, 2.5 baths

$699,000

2 beds2.5 baths1,508 sq ft

48 Preston Ln, Salisbury, CT 06068

Property at 15 Cobble Rd, Falls Village, CT 06031, 4 beds, 3 baths

$1,947,000

4 beds3 baths3,421 sq ft

15 Cobble Rd, Falls Village, CT 06031

Property at 391 Kent Cornwall Rd, Kent, CT 06757, 4 beds, 4 baths

$1,200,000

4 beds4 baths4,200 sq ft

391 Kent Cornwall Rd, Kent, CT 06757

Property at 27 Kearney St, Terryville, CT 06786, 4 beds, 1.5 baths

$394,900

4 beds1.5 baths2,211 sq ft

27 Kearney St, Terryville, CT 06786

Property at 22 Woodlawn Dr, Torrington, CT 06790, 3 beds, 1.5 baths

$389,900

3 beds1.5 baths1,859 sq ft

22 Woodlawn Dr, Torrington, CT 06790

Property at 24 Roxbury Rd, Woodbury, CT 06798, 3 beds, 2.5 baths

$1,149,000

3 beds2.5 baths4,012 sq ft

24 Roxbury Rd, Woodbury, CT 06798

Property at 58 Pumping Station Rd, Torrington, CT 06790, 3 beds, 2.5 baths

$799,000

3 beds2.5 baths3,322 sq ft

58 Pumping Station Rd, Torrington, CT 06790

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

$215,000

3 beds2 baths1,410 sq ft

373 Trailsend Dr #373, Torrington, CT 06790

Property at 33 Nodine Pasture Rd, Kent, CT 06757, 6 beds, 6.5 baths

$7,400,000

6 beds6.5 baths10,549 sq ft

33 Nodine Pasture Rd, Kent, CT 06757

Property at 130 Riverton Rd, Winsted, CT 06098, 3 beds, 2 baths

$420,000

3 beds2 baths1,430 sq ft

130 Riverton Rd, Winsted, CT 06098

Property at 478 Evergreen Rd, Torrington, CT 06790, 2 beds, 2 baths

$199,000

2 beds2 baths1,612 sq ft

478 Evergreen Rd, Torrington, CT 06790

Property at 348 Weekeepeemee Rd, Woodbury, CT 06798, 5 beds, 4.5 baths

$2,149,900

5 beds4.5 baths5,973 sq ft

348 Weekeepeemee Rd, Woodbury, CT 06798

Property at 250 Belgo Rd, Lakeville, CT 06039, 5 beds, 5.5 baths

$6,500,000

5 beds5.5 baths6,944 sq ft

250 Belgo Rd, Lakeville, CT 06039

Property at 229 Bacon Pond Rd #312, Woodbury, CT 06798, 2 beds, 1 bath

$199,900

2 beds1 bath913 sq ft

229 Bacon Pond Rd #312, Woodbury, CT 06798

Property at 11 Day Rd Unit A/B, Cornwall Bridge, CT 06754, 5 beds, 3.5 baths

$1,590,000

5 beds3.5 baths2,062 sq ft

11 Day Rd Unit A/B, Cornwall Bridge, CT 06754

Property at 17 E Bucks Rock Rd, New Milford, CT 06776, 5 beds, 5 baths

$699,900

5 beds5 baths3,322 sq ft

17 E Bucks Rock Rd, New Milford, CT 06776

Property at 67 Woodside Cir #67, Torrington, CT 06790, 2 beds, 2 baths

$199,000

2 beds2 baths1,612 sq ft

67 Woodside Cir #67, Torrington, CT 06790

Property at 63 W Mountain Rd, Washington Depot, CT 06793, 4 beds, 4.5 baths

$2,495,000

4 beds4.5 baths3,699 sq ft

63 W Mountain Rd, Washington Depot, CT 06793

Property at 144 Salmon Kill Rd, Unknown City, CT 06068, 4 beds, 3.5 baths

$3,175,000

4 beds3.5 baths3,072 sq ft

144 Salmon Kill Rd, Unknown City, CT 06068

Property at 55-57 Brinton Hill Rd, Salisbury, CT 06031, 4 beds, 3 baths

$5,375,000

4 beds3 baths4,504 sq ft

55-57 Brinton Hill Rd, Salisbury, CT 06031

Property at 25 Highmeadow Ln, Roxbury, CT 06783, 4 beds, 3 baths

$1,595,000

4 beds3 baths4,310 sq ft

25 Highmeadow Ln, Roxbury, CT 06783

Property at 96 Woodside Cir #96, Torrington, CT 06790, 2 beds, 2 baths

$269,000

2 beds2 baths1,612 sq ft

96 Woodside Cir #96, Torrington, CT 06790

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

$8,250,000

6 beds8 baths8,457 sq ft

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

Property at 9 Birch Rd, New Milford, CT 06776, 4 beds, 2 baths

$699,900

4 beds2 baths2,466 sq ft

9 Birch Rd, New Milford, CT 06776

Property at 4 Sunrise Ln, Bridgewater, CT 06752, 4 beds, 5 baths

$2,395,000

4 beds5 baths5,927 sq ft

4 Sunrise Ln, Bridgewater, CT 06752

Property at 59 Painter Ridge Rd, Washington, CT 06793, 5 beds, 3.5 baths

$2,895,000

5 beds3.5 baths3,844 sq ft

59 Painter Ridge Rd, Washington, CT 06793

Property at 35 Nettleton Hollow Rd, Bethlehem, CT 06751, 4 beds, 3 baths

$775,000

4 beds3 baths3,020 sq ft

35 Nettleton Hollow Rd, Bethlehem, CT 06751

Property at 69 Nonnewaug Rd, Woodbury, CT 06798, 4 beds, 2.5 baths

$850,000

4 beds2.5 baths2,568 sq ft

69 Nonnewaug Rd, Woodbury, CT 06798

Property at 21 Walker Brook Dr, New Milford, CT 06776, 5 beds, 3.5 baths

$769,000

5 beds3.5 baths2,682 sq ft

21 Walker Brook Dr, New Milford, CT 06776

Property at 11 Gaffney Rd, New Milford, CT 06776, 4 beds, 3.5 baths

$1,375,000

4 beds3.5 baths3,162 sq ft

11 Gaffney Rd, New Milford, CT 06776

Property at 212 Ledge Dr, Torrington, CT 06790, 3 beds, 2 baths

$229,000

3 beds2 baths1,612 sq ft

212 Ledge Dr, Torrington, CT 06790

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Based on information submitted to the MLS GRID as of Sat Oct 10 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 154 homes with pools for sale in Litchfield County at a median listing price of $500K. 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 56 days and receive 1 offers. This map is refreshed with the newest listings in Litchfield County every 15 minutes.

In the past month, 210 homes have been sold in Litchfield County. In addition to houses in Litchfield County, there were also 148 condos, 0 townhouses, and 57 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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