Homes with Pools for Sale in Middlesex County, CT

323 homes

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, CT:
Most beach homes ask you to choose: location or amenities, space or style, primary home or vacation retreat. This one says "why not both?" Perfectly positioned just 50 steps from Knollwood Beach, this spacious 3-bedroom 3-bath sanctuary delivers the rare combination of prime beach access and every amenity you'd expect from a year-round residence. A stress free move-in is possible here, as this residence is offered fully furnished. * Start your morning with coffee in the primary suite, with a balcony overlooking the ocean. Work from your spacious private home office with inspiring views. Prepare dinner in a gourmet kitchen designed for serious cooking. End your evening soaking in

$2,795,000

3 beds3 baths3,389 sq ft

372 Maple Ave, Old Saybrook, CT 06475

Home theater • Hot tub • Private sauna

NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, CT:
Final Chance in Lake Overlook Estates. A rare offering in this fully sold-out community - this new colonial will be custom built on a premium elevated . 75 acre lot with stately curb appeal, a 3 car garage, and a floor plan curated for both function + luxury. This 3 bedroom colonial (with the option to convert to a 4 bedroom) features a custom-designed layout, oversized kitchen with large center island, high-end finishes, walk-in pantry, and grand windows framing serene woodland views. The second floor includes a spacious primary suite with full bath + walk-in closet, additional storage, and well-appointed guest bedrooms. Mudroom entry, expansive great room, and beautiful millwork throughou

$649,000

3 beds2.5 baths2,510 sq ft

Lot 14 Lakewood Rd, East Hampton, CT 06424

Premium elevated lot • Oversized kitchen • Grand windows

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, CT:
Back on market! Inspection will show there is some termite damage in one of beams in basement. Charming 4-season cottage with views of Cedar Lake! Corner lot with deck, outdoor shower, and parking. Features an eat-in kitchen, open living area, 3 bedrooms, and hardwood floors.

$229,000

3 beds1 bath748 sq ft

15 Hazen St, Chester, CT 06412

Open living area • Cedar lake views • Outdoor shower

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, CT:
Tucked away at the end of a cul-de-sac, this inviting home offers the perfect blend of comfort, charm, and potential. Enjoy true one-floor living with the flexibility to expand into the unfinished attic. Step inside through the enclosed porch, a versatile space that's perfect for storing coats and winter gear or transforming into a cozy indoor retreat filled with plants and natural light. The main level features an eat-in kitchen, a formal dining room, a spacious living room, two comfortable bedrooms, and a full bath - all exuding warmth and character. The lower level adds even more usable space, complete with two finished rooms (one featuring a bar for entertaining), a half bath, and a con

$330,000

2 beds1.5 baths1,177 sq ft

40 Coe Ave, Portland, CT 06480

Formal dining room • One-floor living • Enclosed porch

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, CT:
A rare opportunity to own a spacious, tranquil retreat in Moodus. This 5-bedroom, 3-bathroom home is set on just over seven private acres and offers a unique blend of open land, wooded trails, and peaceful water views. Set back from the road, the property includes a large front yard, a small pond with a dock, and a huge wraparound deck overlooking both - ideal for quiet mornings or gatherings. A crushed stone fire pit area adds to the outdoor appeal and is perfect for relaxing evenings. Inside, the home features an open floor plan with vaulted ceilings and tongue-and-groove woodwork throughout, all built around a massive stone fireplace that brings warmth and character to the main living ar

$649,900

5 beds3 baths3,000 sq ft

67 Moodus Leesville Rd, Moodus, CT 06469

Private acres • Water views • Dock

Property at 9 Hickory Hill Dr, Chester, CT 06412, 3 beds, 2.5 baths

$799,000

3 beds2.5 baths2,888 sq ft

9 Hickory Hill Dr, Chester, CT 06412

Property at 106 Glenwood Rd, Clinton, CT 06413, 3 beds, 2 baths

$385,000

3 beds2 baths1,402 sq ft

106 Glenwood Rd, Clinton, CT 06413

Property at 33 Whitewood Rd, Killingworth, CT 06419, 2 beds, 1 bath

$114,999

2 beds1 bath732 sq ft

33 Whitewood Rd, Killingworth, CT 06419

Property at 62 River St, Deep River, CT 06417, 4 beds, 2 baths

$749,000

4 beds2 baths1,970 sq ft

62 River St, Deep River, CT 06417

Property at 50 Garfield Ave, Middletown, CT 06457, 3 beds, 2 baths

$389,900

3 beds2 baths1,366 sq ft

50 Garfield Ave, Middletown, CT 06457

Property at 18 Quarry St, Old Saybrook, CT 06475, 4 beds, 2 baths

$605,000

4 beds2 baths1,760 sq ft

18 Quarry St, Old Saybrook, CT 06475

Property at 4 Van Dyke Ln, Clinton, CT 06413, 3 beds, 2 baths

$474,900

3 beds2 baths1,104 sq ft

4 Van Dyke Ln, Clinton, CT 06413

Property at 63 Burr Rd, Higganum, CT 06441, 3 beds, 1.5 baths

$525,000

3 beds1.5 baths2,380 sq ft

63 Burr Rd, Higganum, CT 06441

Property at Lot 13 Lakewood St, East Hampton, CT 06424, 4 beds, 2.5 baths

$689,500

4 beds2.5 baths2,900 sq ft

Lot 13 Lakewood St, East Hampton, CT 06424

Property at 7 Pheasant Run #7, Cromwell, CT 06416, 2 beds, 1.5 baths

$289,900

2 beds1.5 baths1,303 sq ft

7 Pheasant Run #7, Cromwell, CT 06416

Property at 20 Keighley Pond Rd, East Hampton, CT 06456, 3 beds, 3.5 baths

$574,900

3 beds3.5 baths2,505 sq ft

20 Keighley Pond Rd, East Hampton, CT 06456

Property at 18 Lake Blvd, East Hampton, CT 06424, 3 beds, 1 bath

$295,000

3 beds1 bath888 sq ft

18 Lake Blvd, East Hampton, CT 06424

Property at 125 Main St, Old Saybrook, CT 06475, 1 bed, 1.5 baths

$2,195,000

1 bed1.5 baths7,985 sq ft

125 Main St, Old Saybrook, CT 06475

Property at 42 Dogwood Rd, Moodus, CT 06469, 3 beds, 2 baths

$799,900

3 beds2 baths1,944 sq ft

42 Dogwood Rd, Moodus, CT 06469

Property at 34 Woodsboro Cir #34, Cromwell, CT 06416, 2 beds, 2 baths

$519,900

2 beds2 baths1,758 sq ft

34 Woodsboro Cir #34, Cromwell, CT 06416

Property at 8 Tom Rd, East Haddam, CT 06423, 3 beds, 2 baths

$675,000

3 beds2 baths2,560 sq ft

8 Tom Rd, East Haddam, CT 06423

Property at 10 Silver St, Middletown, CT 06457, 4 beds, 1.5 baths

$279,999

4 beds1.5 baths1,415 sq ft

10 Silver St, Middletown, CT 06457

Property at 114 Walkley Hill Rd, Haddam, CT 06438, 5 beds, 6 baths

$2,500,000

5 beds6 baths5,768 sq ft

114 Walkley Hill Rd, Haddam, CT 06438

Property at 22 Linda Ct #22, Cromwell, CT 06416, 1 bed, 1 bath

$174,900

1 bed1 bath804 sq ft

22 Linda Ct #22, Cromwell, CT 06416

Property at 9 Sunset Dr, Rockfall, CT 06481, 3 beds, 1.5 baths

$379,000

3 beds1.5 baths1,760 sq ft

9 Sunset Dr, Rockfall, CT 06481

Property at 85 River Rd Apt B7, Essex, CT 06426, 3 beds, 1.5 baths

$465,000

3 beds1.5 baths1,375 sq ft

85 River Rd Apt B7, Essex, CT 06426

Property at 15 Oxford Ln, Cromwell, CT 06416, 4 beds, 2.5 baths

$585,000

4 beds2.5 baths2,740 sq ft

15 Oxford Ln, Cromwell, CT 06416

Property at Lot 4 Nathan Hale Rd, Middletown, CT 06457, 3 beds, 2.5 baths

$574,900

3 beds2.5 baths1,761 sq ft

Lot 4 Nathan Hale Rd, Middletown, CT 06457

Property at 233 Oak Ridge Dr, Middletown, CT 06457, 3 beds, 2 baths

$350,000

3 beds2 baths1,053 sq ft

233 Oak Ridge Dr, Middletown, CT 06457

Property at 209 Main St, Deep River, CT 06417, 9 beds, 9 baths

$1,199,999

9 beds9 baths4,982 sq ft

209 Main St, Deep River, CT 06417

Property at 821 Essex Rd, Westbrook, CT 06498, 4 beds, 3.5 baths

$699,900

4 beds3.5 baths3,308 sq ft

821 Essex Rd, Westbrook, CT 06498

Property at 229 Killingworth Tpke #28, Clinton, CT 06413, 2 beds, 2 baths

$76,300

2 beds2 baths1,056 sq ft

229 Killingworth Tpke #28, Clinton, CT 06413

Listing provided by Zillow

Property at Green Acres Park Dr #27, Westbrook, CT 06498, 2 beds, 1 bath

$66,500

2 beds1 bath720 sq ft

Green Acres Park Dr #27, Westbrook, CT 06498

Listing provided by Zillow

Property at 229 Killingworth Tpke #14, Clinton, CT 06413, 2 beds, 2 baths

$76,300

2 beds2 baths1,056 sq ft

229 Killingworth Tpke #14, Clinton, CT 06413

Listing provided by Zillow

Property at 229 Killingworth Tpke #27, Clinton, CT 06413, 2 beds, 2 baths

$76,300

2 beds2 baths1,056 sq ft

229 Killingworth Tpke #27, Clinton, CT 06413

Listing provided by Zillow

Property at 133 W Main St Unit A13, Clinton, CT 06413, 2 beds, 1 bath

$69,999

2 beds1 bath624 sq ft

133 W Main St Unit A13, Clinton, CT 06413

Listing provided by Zillow

Property at 133 W Main St Unit C3, Clinton, CT 06413, 2 beds, 1 bath

$71,099

2 beds1 bath720 sq ft

133 W Main St Unit C3, Clinton, CT 06413

Listing provided by Zillow

Property at 347 Farm Hill Rd, Middletown, CT 06457, 3 beds, 1 bath

$314,900

3 beds1 bath1,974 sq ft

347 Farm Hill Rd, Middletown, CT 06457

Property at 548 Main St, Portland, CT 06480, 5 beds, 2 baths

$439,999

5 beds2 baths2,615 sq ft

548 Main St, Portland, CT 06480

Property at 92 Main St Apt 101, Deep River, CT 06417, 1 bath

$199,000

— beds1 bath484 sq ft

92 Main St Apt 101, Deep River, CT 06417

Property at Lot 3 Nathan Hale Rd, Middletown, CT 06457, 3 beds, 2.5 baths

$574,900

3 beds2.5 baths1,761 sq ft

Lot 3 Nathan Hale Rd, Middletown, CT 06457

Viewing page 3 of 8

Homes with Pools for Sale in Middlesex County

There are currently 323 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.

More real estate resources for Middlesex County, CT

Cities

Nearby Counties

Nearby Counties with Homes with Pools

Nearby Cities with Homes with Pools

More to explore in Middlesex County, CT

How to buy a house in Middlesex County, CT

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Connecticut

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.