Homes with Pools for Sale in Litchfield County, CT

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ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
A Reimagined Gem in the Heart of Sharon's Northwest Hills. Discover the perfect blend of classic charm and modern peace of mind at 50 Jewett Hill Rd. This delightful 3 bedroom, 1.5 bathroom Cape Cod has undergone a complete metamorphosis, a true labor of love that has transformed it into a turn-key sanctuary. Every inch of this home has been tastefully remodeled. You can move in worry-free thanks to comprehensive updates including a new roof, windows, vinyl siding, full insulation, updated plumbing, electrical, and central air. The interior features a sparkling new kitchen and modern bathrooms, while the exterior boasts two new pressure-treated decks perfect for morning coffee or evening en

$599,000

3 beds1.5 baths1,356 sq ft

50 Jewett Hill Rd, Sharon, CT 06069

0.66 acre lot • 4 parking spots • Built 1927

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
Move right into this 3 bedroom, 2 full bath Cape. Fully fenced in back yard is great for dogs or children with a gazebo and shed. Features 1st floor bedroom and bath with 1st floor laundry. 2nd floor offers 2 very large bedrooms and a full bath. Complete with mini-split system for central air as well as a pellet stove for cold winter nights. Updated mechanicals, baths and flooring. Granite counters in kitchen. New thermal paned windows. Full walkout basement for the handy man. Solar panels $113 monthly on 25 yr lease.

$315,000

3 beds2 baths1,075 sq ft

35 Calli St, Torrington, CT 06790

0.25 acre lot • 2 garage spots • Built 1980

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
"Where Luxury Meets the Landscape. " Welcome to a home where nature and craftsmanship converge in breathtaking harmony. Nestled on five professionally landscaped acres, this country manor is a sanctuary of serenity and sophistication. A statuesque quarry of stone lines one side of the property, perfectly balanced by a tranquil body of water-inviting you to kayak, canoe, or skate through the seasons or perhaps just enjoy the resident eagles or osprey who make the area their home during some of the year. As you enter, the grand open staircase is the centerpiece of a 2-story wrap-around Foyer that sets the stage for the comfortable elegance this home inspires. Step inside and experi

$1,267,500

4 beds4.5 baths4,676 sq ft

101 Old Grassy Hill Rd, Woodbury, CT 06798

5.17 acre lot • 5 garage spots • Built 2004

NEW 15 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
UNIQUE OPPORTUNITY WITH MULTIPLE POSSIBILITIES!!! Located in the classic New England town of Bethlehem on 8.5+ acres this is your opportunity for unlimited potential. Build your own Private Estate, Family Compound, Multi-Family Investment, Business Operations with Offices and Storage, Horse Property, Farm and Possible Residential Development. There are two Residential homes and additional structures that can be re-fit to meet your needs. Existing Structures: Primary Residence - 1,876sf with 3 Bedrooms, 2 Bathrooms; Second Home - 1,100sf with 2 Bedrooms and 1 Bathroom and a 3 Car Garage with a Half-Bathroom. Two additional buildings for storage, hobbies, cars, boats, and all the toys you can

$725,000

3 beds2 baths1,876 sq ft

202 Crane Hollow Rd, Bethlehem, CT 06751

Horse property • Farm • Private estate

ABOUT THIS HOME
Home with a Pool for sale in Litchfield County, CT:
Welcome to 360 Old Sherman Hill Road in Woodbury! This charming 3-bedroom, 2-bath single-family home offers an inviting blend of space, comfort, and natural light. Featuring multiple skylights and a cozy wood stove furnace, the home boasts a large living room perfect for gatherings and an spacious eat-in kitchen complete with stainless steel appliances. The partially finished full basement provides additional living or storage space and includes a dedicated laundry room. Powered by an oil-fueled boiler, the property also highlights an above-ground pool with a deck built around it-ideal for summer enjoyment-and a spacious 2-car detached garage. A wonderful opportunity to enjoy peaceful livin

$529,000

3 beds2 baths1,296 sq ft

360 Old Sherman Hill Rd, Woodbury, CT 06798

Multiple skylights • Large living room • 1.11 acre lot

Property at 154 Lincoln Ave, Torrington, CT 06790, 3 beds, 1.5 baths

$160,000

3 beds1.5 baths1,316 sq ft

154 Lincoln Ave, Torrington, CT 06790

Property at 6 Sarah Sanford Rd W, Bridgewater, CT 06752, 3 beds, 2 baths

$695,000

3 beds2 baths2,006 sq ft

6 Sarah Sanford Rd W, Bridgewater, CT 06752

Property at 115 Great Brook Rd, New Milford, CT 06776, 3 beds, 2 baths

$474,000

3 beds2 baths1,808 sq ft

115 Great Brook Rd, New Milford, CT 06776

Property at 15 Sharon Valley Rd, Sharon, CT 06069, 4 beds, 2 baths

$420,000

4 beds2 baths1,930 sq ft

15 Sharon Valley Rd, Sharon, CT 06069

DUTCHESS COUNTRY REALTY INC. M

Property at 1101 Hickory Hill Rd, Thomaston, CT 06787, 3 beds, 2 baths

$299,000

3 beds2 baths1,348 sq ft

1101 Hickory Hill Rd, Thomaston, CT 06787

Property at 29 Berry St, Torrington, CT 06790, 6 beds, 2 baths

$340,000

6 beds2 baths1,910 sq ft

29 Berry St, Torrington, CT 06790

Property at 18 Tumblebrook Rd, Terryville, CT 06786, 3 beds, 2 baths

$345,900

3 beds2 baths1,300 sq ft

18 Tumblebrook Rd, Terryville, CT 06786

Property at 7 Kearney St, Terryville, CT 06786, 5 beds, 2 baths

$315,000

5 beds2 baths2,198 sq ft

7 Kearney St, Terryville, CT 06786

Property at 238 Sylvan Lake Rd, Oakville, CT 06779, 3 beds, 1.5 baths

$400,000

3 beds1.5 baths1,080 sq ft

238 Sylvan Lake Rd, Oakville, CT 06779

Property at 9 Heather Ct #9, Woodbury, CT 06798, 2 beds, 2.5 baths

$294,900

2 beds2.5 baths1,723 sq ft

9 Heather Ct #9, Woodbury, CT 06798

Property at 18 Tarlton St, Torrington, CT 06790, 2 beds, 1 bath

$225,000

2 beds1 bath826 sq ft

18 Tarlton St, Torrington, CT 06790

Property at 9 John St, Winsted, CT 06098, 2 beds, 1.5 baths

$230,000

2 beds1.5 baths1,172 sq ft

9 John St, Winsted, CT 06098

Property at 65 Oak Meadow Ln #65, Torrington, CT 06791, 2 beds, 3.5 baths

$495,000

2 beds3.5 baths2,964 sq ft

65 Oak Meadow Ln #65, Torrington, CT 06791

Property at 107 Peck Rd, Winsted, CT 06098, 3 beds, 1 bath

$339,000

3 beds1 bath960 sq ft

107 Peck Rd, Winsted, CT 06098

Property at 175 Willow Spgs #175, New Milford, CT 06776, 2 beds, 1 bath

$290,000

2 beds1 bath1,025 sq ft

175 Willow Spgs #175, New Milford, CT 06776

Property at 9 Hill View Ln, Woodbury, CT 06798, 2 beds, 2.5 baths

$539,000

2 beds2.5 baths3,362 sq ft

9 Hill View Ln, Woodbury, CT 06798

Property at 80 Baron Ln, Torrington, CT 06790, 4 beds, 1 bath

$350,000

4 beds1 bath1,315 sq ft

80 Baron Ln, Torrington, CT 06790

Property at 208 Spencer Hill Rd, Winsted, CT 06098, 3 beds, 1.5 baths

$399,000

3 beds1.5 baths1,969 sq ft

208 Spencer Hill Rd, Winsted, CT 06098

Property at 157 Elm St, Winsted, CT 06098, 6 beds, 2.5 baths

$339,000

6 beds2.5 baths2,376 sq ft

157 Elm St, Winsted, CT 06098

Property at 160 Laurel Hill Rd, Torrington, CT 06790, 4 beds, 3 baths

$524,900

4 beds3 baths2,164 sq ft

160 Laurel Hill Rd, Torrington, CT 06790

Property at 21 Oak Meadow Ln #21, Torrington, CT 06791, 2 beds, 2.5 baths

$450,000

2 beds2.5 baths2,164 sq ft

21 Oak Meadow Ln #21, Torrington, CT 06791

Property at 8 Bancroft St, Torrington, CT 06790, 4 beds, 2 baths

$324,900

4 beds2 baths1,430 sq ft

8 Bancroft St, Torrington, CT 06790

Property at 57 Osage Cir, Watertown, CT 06795, 3 beds, 1 bath

$375,000

3 beds1 bath1,104 sq ft

57 Osage Cir, Watertown, CT 06795

Property at 7 Ford Ln, Torrington, CT 06790, 4 beds, 3 baths

$462,000

4 beds3 baths2,356 sq ft

7 Ford Ln, Torrington, CT 06790

Property at 77 New Milford Tpke, New Preston, CT 06777, 13 beds, 9.5 baths

$695,000

13 beds9.5 baths7,501 sq ft

77 New Milford Tpke, New Preston, CT 06777

Property at 124 North St, Litchfield, CT 06759, 6 beds, 6 baths

$1,350,000

6 beds6 baths4,910 sq ft

124 North St, Litchfield, CT 06759

Property at 95 Nalette Dr, Winsted, CT 06098, 3 beds, 2.5 baths

$365,000

3 beds2.5 baths2,356 sq ft

95 Nalette Dr, Winsted, CT 06098

Property at 31 Main St, Northfield, CT 06778, 4 beds, 3 baths

$470,000

4 beds3 baths1,873 sq ft

31 Main St, Northfield, CT 06778

Property at 2 Chapel Hill Rd, New Milford, CT 06776, 3 beds, 1.5 baths

$380,000

3 beds1.5 baths1,036 sq ft

2 Chapel Hill Rd, New Milford, CT 06776

Property at 41 Overlook Dr, New Milford, CT 06776, 3 beds, 2.5 baths

$565,000

3 beds2.5 baths2,274 sq ft

41 Overlook Dr, New Milford, CT 06776

Property at 11 W Chestnut Hill Rd, Litchfield, CT 06759, 5 beds, 3.5 baths

$765,000

5 beds3.5 baths3,328 sq ft

11 W Chestnut Hill Rd, Litchfield, CT 06759

Property at 262 Candlewood Lake Rd N, New Milford, CT 06776, 4 beds, 2.5 baths

$519,000

4 beds2.5 baths2,352 sq ft

262 Candlewood Lake Rd N, New Milford, CT 06776

Property at 308 Skiff Mountain Rd, Kent, CT 06757, 3 beds, 3 baths

$1,250,000

3 beds3 baths3,296 sq ft

308 Skiff Mountain Rd, Kent, CT 06757

Property at 117 Cherry Ave, Watertown, CT 06795, 3 beds, 2.5 baths

$360,000

3 beds2.5 baths1,552 sq ft

117 Cherry Ave, Watertown, CT 06795

Property at 432 Quassapaug Rd, Woodbury, CT 06798, 4 beds, 3 baths

$775,000

4 beds3 baths2,980 sq ft

432 Quassapaug Rd, Woodbury, CT 06798

Property at 187 Torringford St, Winsted, CT 06098, 4 beds, 1.5 baths

$429,000

4 beds1.5 baths2,365 sq ft

187 Torringford St, Winsted, CT 06098

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Based on information submitted to the MLS GRID as of Wed Dec 03 2025. 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 625 homes with pools for sale in Litchfield County at a median listing price of $485K. 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 63 days and receive 3 offers. This map is refreshed with the newest listings in Litchfield County every 15 minutes.

In the past month, 215 homes have been sold in Litchfield County. In addition to houses in Litchfield County, there were also 130 condos, 0 townhouses, and 49 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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