Homes with Pools for Sale in Middlesex County, CT

324 homes

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ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, CT:
* * A Unique Opportunity at 30 Chestnut Hill Road, Killingworth * * Step into a piece of history with this charming antique home, circa 1820-now available from a seasoned preservationist and architect with decades of experience restoring historic homes and barns. This property has already undergone critical structural repairs and has a watertight roof, setting the stage for the next phase of transformation. Exterior work-including masonry, roof detailing, windows, and finish-is underway. Current renovation plans envision a spacious 3-bedroom, 2.5-bath layout featuring a dedicated office, library, and over 3,000 square feet of living space. When completed, the home-along with a barn/gar

$340,000

4 beds1 bath1,756 sq ft

30 Chestnut Hill Rd, Killingworth, CT 06419

Masonry work • Watertight roof • Roof detailing

3D & VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, CT:
Experience the grandeur of this private estate, where the tranquil Eight Mile River flows beside a beautifully restored home. Thoughtfully remodeled, this residence blends timeless character with premium finishes and exceptional craftsmanship. Enter through an elegant main entrance or mudroom with bluestone flooring, leading to a gourmet country kitchen featuring a Z-Line double oven, gas cooktop, soapstone counters, and a Salamander wood stove-all with serene pond and patio views. Host gatherings in the formal dining room or relax in the living room with a fireplace, built-in bookshelves, and a wall of new Anderson windows. The dedicated office offers custom built-ins and peaceful river vi

$2,395,000

4 beds5 baths4,516 sq ft

38 Three Bridges Rd, East Haddam, CT 06423

Gas cooktop • Soapstone counters • Formal dining room

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, CT:
Every home tells a story and the often admired c. 1704 Black Horse Tavern in historic North Cove is no exception. Located at the waters edge and offering expansive water views, this stunning private residence is rich in both local history and architectural detail. Meticulously curated to perfection, quality of craftsmanship is evident throughout. A warm and welcoming entry leads to elegant well-proportioned rooms, ideal for entertaining. The formal living room and dining room, each with their own fireplace, offers the perfect balance of relaxed & refined. The Chef's kitchen with a casual dining area centered around the fireplace is perfect everyday gatherings and the sunroom, with flo

$3,750,000

4 beds4.5 baths3,518 sq ft

175 N Cove Rd, Old Saybrook, CT 06475

In-ground pool • Sunroom • Formal living room

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, CT:
Welcome to your perfect family retreat in Haddam/Higganum! This beautifully updated three-bedroom, two-bath home combines historic charm with modern upgrades, offering a spacious layout, renovated kitchen and bathrooms, and a large yard for outdoor living. Located just a mile from the Higganum Center, it features an open floor plan that is ideal for entertaining. The bright living room, featuring a gas fireplace, flows seamlessly into the dining area and updated kitchen, complete with stainless steel appliances, custom cabinetry, and elegant countertops, perfect for family gatherings. There are three bedrooms and two spa-inspired bathrooms. The lower-level great room features high ceilings

$525,000

3 beds2 baths2,113 sq ft

16 Walkley Hill Rd, Haddam, CT 06438

0.83 acre lot • 3 garage spots • Built 1935

NEW CONSTRUCTIONVIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, CT:
Welcome to Sterling Sand Village - Coastal Living in Clinton Township. Discover the charm of Sterling Sand Village, a community under development, perfectly situated along the shoreline of Clinton Beach and Marina. Nestled in tranquil Clinton Township, this new development combines modern comfort with coastal beauty, offering an exceptional lifestyle just minutes from Clinton Premium Outlets, Clinton Town Beach, and Hammonasset Beach State Park. This COMING SOON enclave features 28 thoughtfully designed duplex townhomes with 2,200 square feet of living space. Each Wisteria & Birchwood model unit offers an option for 3 bedrooms (OR) two with a loft/study, 2.5 baths, one car garage and

$649,000

3 beds2.5 baths2,200 sq ft

151 - 153 East Main St #9, Clinton, CT 06413

$500 HOA • Garage • Built 2025

Property at 77 Main St, East Haddam, CT 06423, 4 beds, 4 baths

$1,600,000

4 beds4 baths4,070 sq ft

77 Main St, East Haddam, CT 06423

Property at 204 Old Blue Hills Rd, Durham, CT 06422, 4 beds, 2 baths

$699,900

4 beds2 baths2,400 sq ft

204 Old Blue Hills Rd, Durham, CT 06422

Property at 26 Old Wallingford Rd, Durham, CT 06422, 5 beds, 3 baths

$899,000

5 beds3 baths5,664 sq ft

26 Old Wallingford Rd, Durham, CT 06422

Property at 52 Rising Trail Dr #52, Middletown, CT 06457, 2 beds, 1.5 baths

$210,000

2 beds1.5 baths1,120 sq ft

52 Rising Trail Dr #52, Middletown, CT 06457

Property at 118 Sandy Point Rd #118, Old Saybrook, CT 06475, 2 beds, 1.5 baths

$519,000

2 beds1.5 baths1,557 sq ft

118 Sandy Point Rd #118, Old Saybrook, CT 06475

Property at 85 Salem Rd, Colchester, CT 06415, 4 beds, 4 baths

$1,224,000

4 beds4 baths3,628 sq ft

85 Salem Rd, Colchester, CT 06415

Property at 17 Lookout Hl, Essex, CT 06426, 5 beds, 5 baths

$1,349,000

5 beds5 baths5,364 sq ft

17 Lookout Hl, Essex, CT 06426

Property at 153 Wallingford Rd, Durham, CT 06422, 15 beds, 7.5 baths

$2,800,000

15 beds7.5 baths10,623 sq ft

153 Wallingford Rd, Durham, CT 06422

Property at 148 Wallingford Rd, Durham, CT 06422, 7 beds, 2.5 baths

$1,999,000

7 beds2.5 baths3,308 sq ft

148 Wallingford Rd, Durham, CT 06422

Property at 48A Ironworks Rd, Clinton, CT 06413, 3 beds, 3.5 baths

$899,900

3 beds3.5 baths2,164 sq ft

48A Ironworks Rd, Clinton, CT 06413

Property at 10 Mulberry St, Old Saybrook, CT 06475

$575,000

— beds— baths— sq ft

10 Mulberry St, Old Saybrook, CT 06475

Property at 64 W Main St, Clinton, CT 06413

$225,000

— beds— baths— sq ft

64 W Main St, Clinton, CT 06413

Property at Country Club Rd and Massa Tom Rd Rd E, Middletown, CT 06457

$1,200,000

— beds— baths— sq ft

Country Club Rd and Massa Tom Rd Rd E, Middletown, CT 06457

Property at Fairview St, Essex, CT 06426

$125,000

— beds— baths— sq ft

Fairview St, Essex, CT 06426

Property at 0 Lakeside Dr, East Haddam, CT 06423

$75,000

— beds— baths— sq ft

0 Lakeside Dr, East Haddam, CT 06423

Property at 1333A Boston Post Rd, Old Saybrook, CT 06475

$995,000

— beds— baths— sq ft

1333A Boston Post Rd, Old Saybrook, CT 06475

Property at 708 Fox Hopyard Rd, East Haddam, CT 06423

$169,900

— beds— baths— sq ft

708 Fox Hopyard Rd, East Haddam, CT 06423

Property at 709 Fox Hopyard Rd, East Haddam, CT 06423

$159,900

— beds— baths— sq ft

709 Fox Hopyard Rd, East Haddam, CT 06423

$725,000

— beds— baths— sq ft

4 Bank Ln, Essex, CT 06426

Property at Lot 2 Coleman Rd, Middletown, CT 06457

$159,000

— beds— baths— sq ft

Lot 2 Coleman Rd, Middletown, CT 06457

Property at 253 Clark Hill Rd, East Haddam, CT 06423

$375,000

— beds— baths— sq ft

253 Clark Hill Rd, East Haddam, CT 06423

Property at 215 Chamberlain Hill Rd, Higganum, CT 06441

$625,000

— beds— baths— sq ft

215 Chamberlain Hill Rd, Higganum, CT 06441

Property at 4 Laurel Ln, Clinton, CT 06413

$299,000

— beds— baths— sq ft

4 Laurel Ln, Clinton, CT 06413

Property at Mountain Laurel Dr, Middletown, CT 06457

$129,000

— beds— baths— sq ft

Mountain Laurel Dr, Middletown, CT 06457

Property at 428 Plains Rd, Haddam, CT 06438

$125,000

— beds— baths— sq ft

428 Plains Rd, Haddam, CT 06438

Property at 18 west street Ter, Cromwell, CT 06416

$199,900

— beds— baths— sq ft

18 west street Ter, Cromwell, CT 06416

Property at 192 E Main St, Clinton, CT 06413

$799,500

— beds— baths— sq ft

192 E Main St, Clinton, CT 06413

Property at 41 Bushy Hill Rd, Ivoryton, CT 06442

$375,000

— beds— baths— sq ft

41 Bushy Hill Rd, Ivoryton, CT 06442

Property at Baileyville Rd, Middlefield, CT 06455

$399,000

— beds— baths— sq ft

Baileyville Rd, Middlefield, CT 06455

Property at 28 & 33 River Rd, Cromwell, CT 06416

$138,000

— beds— baths— sq ft

28 & 33 River Rd, Cromwell, CT 06416

Property at 21 Olmstead Rd, East Haddam, CT 06423

$100,000

— beds— baths— sq ft

21 Olmstead Rd, East Haddam, CT 06423

Property at 43 Bokum Rd, Chester, CT 06412

$200,000

— beds— baths— sq ft

43 Bokum Rd, Chester, CT 06412

Property at Kikapoo Rd, Middlefield, CT 06481

$125,000

— beds— baths— sq ft

Kikapoo Rd, Middlefield, CT 06481

Property at 10 Cherry Swamp Rd, Moodus, CT 06469

$115,000

— beds— baths— sq ft

10 Cherry Swamp Rd, Moodus, CT 06469

Property at 0 Gadpouch Rd, Portland, CT 06480

$60,000

— beds— baths— sq ft

0 Gadpouch Rd, Portland, CT 06480

Property at 86 Bushy Hill Rd, Ivoryton, CT 06442

$175,000

— beds— baths— sq ft

86 Bushy Hill Rd, Ivoryton, CT 06442

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Homes with Pools for Sale in Middlesex County

There are currently 324 homes with pools for sale in Middlesex County at a median listing price of $499K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Middlesex County stay on the market for 45 days and receive 1 offers. This map is refreshed with the newest listings in Middlesex County every 15 minutes.

In the past month, 193 homes have been sold in Middlesex County. In addition to houses in Middlesex County, there were also 97 condos, 0 townhouses, and 21 multi-family units for sale in Middlesex County last month. Find your dream home in Middlesex 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 Middlesex County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Middlesex County. If you're looking to sell your home in the Middlesex County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Middlesex 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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