Homes with Pools for Sale in Middlesex County, MA

647 homes + 8 early access

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, MA:
Introducing 54 Squire Road, an exceptional newer Colonial privately sited within one of Winchester’s most desirable enclaves. Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades. Highlights include 9’ ceilings, elegant millwork, a designer chef’s kitchen with premium appliances, an impressive family room with custom built-ins and entertaining bar, formal dining with butler’s pantry, private office, and luxurious primary suite with vaulted ceilings, walk-in closets, and spa bath. Expanded outdoor living features a custom outdoor kitchen, fire pit, and multiple patios designed for

$2,499,000

4 beds4.5 baths4,450 sq ft

54 Squire Rd, Winchester, MA 01890

Multiple patios • Fire pit • Home gym

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, MA:
Spacious, warm, and inviting L-shaped ranch nestled in North Framingham's most desirable area, right on the Sudbury and Wayland line! Set in a quiet cul-de-sac neighborhood, this bright and expanded 3–4 bedroom, 2.5-bath home offers over 1,800 sq ft of living space and a 1-car attached garage. Features an open floor plan designed for today's lifestyle, including a large eat-in kitchen leading to the backyard, a fireplaced living room, and a formal dining room. The versatile 24x20 addition with cathedral ceilings, sliding glass door, full bath, and walk-in closet can serve as a primary suite or oversized family room. Enjoy many major upgrades completed since 2020! Situated on a large,

$669,000

4 beds2.5 baths1,816 sq ft

59 Eaton Rd, Framingham, MA 01701

Open floor plan • Large eat in kitchen • L shaped ranch

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, MA:
Exceptional craftsmanship defines this majestic home in The Flats, where beautifully-preserved architectural details blend seamlessly w/ modern livability. A showstopping foyer welcomes you w/ a sweeping staircase, exquisite millwork, graceful arched openings & leaded glass windows. You’ll find quarter-sawn oak floors, rich woodwork, generously scaled windows & impressive ceiling height throughout. The expanded eat-in kitchen includes granite, SS appliances, island, office area & steps to a custom mudroom. The main level also includes elegant living, dining & family rooms, a butler's pantry, & ½ bath. The 2nd floor showcases a dramatic landing w/ co

$2,299,000

7 beds4.5 baths4,930 sq ft

42 Wildwood St, Winchester, MA 01890

Custom mudroom • Showstopping foyer • Sweeping staircase

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, MA:
Welcome to this charming and beautifully maintained 3 bedroom, 2.5 bath Colonial, where comfortable living meets a truly special outdoor retreat. The first floor features a spacious living room, dining room, and inviting kitchen with center island, plus a family room overlooking the stunning backyard. Step outside to the deck and discover a private oasis with an in ground heated pool, creating the perfect setting for entertaining, relaxing, and making memories. Upstairs are three spacious bedrooms, a full bath, and a walk up attic for more storage. The finished basement provides additional flexible space with a finished room and a walk-in full bath, ideal for a home office, guest space, or

$975,000

3 beds2.5 baths2,080 sq ft

166 Waverly Ave, Melrose, MA 02176

Flexible space • Walk up attic • Finished basement

ABOUT THIS HOME
Home with a Pool for sale in Middlesex County, MA:
Located in one of Wayland's most sought-after neighborhoods, Daymon Farms, this completely renovated residence blends timeless design with exceptional craftsmanship. Every detail has been thoughtfully curated, from the designer lighting and custom millwork to the premium finishes and fixtures, creating a home that is both sophisticated and inviting. The sun-filled open floor plan offers seamless flow between the kitchen, dining, and living spaces, making it ideal for everyday living and effortless entertaining. Set on a beautifully landscaped lot with an expansive backyard, the property offers endless opportunities for outdoor enjoyment. The existing in-ground pool presents exciting potenti

$1,750,000

4 beds2.5 baths2,656 sq ft

30 Snake Brk, Wayland, MA 01778

Custom millwork • Premium finishes • Completely renovated

Property at 661 Lowell St #14, Lexington, MA 02420, 2 beds, 2.5 baths

$820,000

2 beds2.5 baths1,438 sq ft

661 Lowell St #14, Lexington, MA 02420

Property at 110 Thornberry Rd, Winchester, MA 01890, 3 beds, 2.5 baths

$1,399,000

3 beds2.5 baths2,459 sq ft

110 Thornberry Rd, Winchester, MA 01890

Property at 356 Burroughs Rd, Boxboro, MA 01719, 4 beds, 4.5 baths

$1,749,000

4 beds4.5 baths4,893 sq ft

356 Burroughs Rd, Boxboro, MA 01719

Property at 255 North Rd #187, Chelmsford, MA 01824, 2 beds, 2 baths

$399,900

2 beds2 baths1,300 sq ft

255 North Rd #187, Chelmsford, MA 01824

Property at 166-168 East Side Pkwy, Newton, MA 02458, 5 beds, 2 baths

$1,495,000

5 beds2 baths2,810 sq ft

166-168 East Side Pkwy, Newton, MA 02458

Property at 204 Great Rd, Maynard, MA 01754, 3 beds, 1.5 baths

$464,900

3 beds1.5 baths1,822 sq ft

204 Great Rd, Maynard, MA 01754

Property at 147 Main St, Reading, MA 01867, 2 beds, 1.5 baths

$599,900

2 beds1.5 baths1,006 sq ft

147 Main St, Reading, MA 01867

Property at 1 Town Way, Winchester, MA 01890, 3 beds, 3.5 baths

$1,794,000

3 beds3.5 baths3,010 sq ft

1 Town Way, Winchester, MA 01890

Property at 49 Clark St #49, Newton, MA 02459, 2 beds, 1.5 baths

$795,000

2 beds1.5 baths1,005 sq ft

49 Clark St #49, Newton, MA 02459

Property at 18 Henry St, Everett, MA 02149, 5 beds, 3 baths

$889,999

5 beds3 baths2,393 sq ft

18 Henry St, Everett, MA 02149

Property at 41 Maple St, Stoneham, MA 02180, 4 beds, 3 baths

$1,298,000

4 beds3 baths2,418 sq ft

41 Maple St, Stoneham, MA 02180

Property at 106 Concord Rd, Bedford, MA 01730, 5 beds, 2.5 baths

$1,262,000

5 beds2.5 baths3,224 sq ft

106 Concord Rd, Bedford, MA 01730

Property at 29 Bowman St, Malden, MA 02148, 4 beds, 3 baths

$775,000

4 beds3 baths2,211 sq ft

29 Bowman St, Malden, MA 02148

Property at 36 Regal St, Holliston, MA 01746, 3 beds, 1 bath

$599,900

3 beds1 bath1,128 sq ft

36 Regal St, Holliston, MA 01746

Property at 241 Ridge St, Winchester, MA 01890, 4 beds, 3 baths

$1,499,000

4 beds3 baths2,480 sq ft

241 Ridge St, Winchester, MA 01890

Property at 132 Central St, North Reading, MA 01864, 3 beds, 2.5 baths

$1,145,000

3 beds2.5 baths2,818 sq ft

132 Central St, North Reading, MA 01864

Property at 1174 Franklin St, Stoneham, MA 02180, 4 beds, 1 bath

$849,900

4 beds1 bath2,109 sq ft

1174 Franklin St, Stoneham, MA 02180

Property at 12 Trillium Way, Sudbury, MA 01776, 5 beds, 3.5 baths

$1,895,000

5 beds3.5 baths4,342 sq ft

12 Trillium Way, Sudbury, MA 01776

Property at 217 Main St, Groton, MA 01450, 4 beds, 3.5 baths

$925,000

4 beds3.5 baths3,280 sq ft

217 Main St, Groton, MA 01450

Property at 320 Western Ave, Sherborn, MA 01770, 4 beds, 2.5 baths

$1,450,000

4 beds2.5 baths3,076 sq ft

320 Western Ave, Sherborn, MA 01770

Property at 80 Dell Ave, Melrose, MA 02176, 5 beds, 3.5 baths

$1,249,900

5 beds3.5 baths2,130 sq ft

80 Dell Ave, Melrose, MA 02176

Property at 13 Park Ln, Wayland, MA 01778, 2 beds, 1 bath

$549,000

2 beds1 bath1,039 sq ft

13 Park Ln, Wayland, MA 01778

Property at 124 Spruce St #124, Watertown, MA 02472, 4 beds, 2 baths

$839,000

4 beds2 baths1,773 sq ft

124 Spruce St #124, Watertown, MA 02472

Property at 9-9a Second St, Medford, MA 02155, 5 beds, 3.5 baths

$1,199,000

5 beds3.5 baths2,264 sq ft

9-9a Second St, Medford, MA 02155

Property at 52 Wyman St, Woburn, MA 01801, 4 beds, 2 baths

$785,000

4 beds2 baths1,901 sq ft

52 Wyman St, Woburn, MA 01801

Property at 164 Galen St #61, Watertown, MA 02472, 2 beds, 1 bath

$424,900

2 beds1 bath950 sq ft

164 Galen St #61, Watertown, MA 02472

Property at 17 Saint Denis Ave, Medford, MA 02155, 3 beds, 1.5 baths

$839,000

3 beds1.5 baths1,274 sq ft

17 Saint Denis Ave, Medford, MA 02155

Property at 601 Winter St, Framingham, MA 01702, 3 beds, 2.5 baths

$799,900

3 beds2.5 baths1,812 sq ft

601 Winter St, Framingham, MA 01702

Property at 25 Russett Hill Rd, Sherborn, MA 01770, 4 beds, 2.5 baths

$1,250,000

4 beds2.5 baths2,944 sq ft

25 Russett Hill Rd, Sherborn, MA 01770

Property at 112 Farm Rd, Sherborn, MA 01770, 5 beds, 4 baths

$4,995,000

5 beds4 baths4,400 sq ft

112 Farm Rd, Sherborn, MA 01770

Property at 30 Calvin St, Lexington, MA 02420, 5 beds, 4.5 baths

$2,300,000

5 beds4.5 baths4,113 sq ft

30 Calvin St, Lexington, MA 02420

Property at 10 Lowell Dr, Stow, MA 01775, 4 beds, 2.5 baths

$829,000

4 beds2.5 baths2,478 sq ft

10 Lowell Dr, Stow, MA 01775

Property at 303 Alewife Brook Pkwy, Somerville, MA 02144, 4 beds, 2 baths

$999,999

4 beds2 baths2,204 sq ft

303 Alewife Brook Pkwy, Somerville, MA 02144

Property at 46 Black Burnian Rd, Weston, MA 02493, 4 beds, 4 baths

$3,149,000

4 beds4 baths6,119 sq ft

46 Black Burnian Rd, Weston, MA 02493

Property at 254 Cambridge Rd, Woburn, MA 01801, 3 beds, 1.5 baths

$724,900

3 beds1.5 baths1,923 sq ft

254 Cambridge Rd, Woburn, MA 01801

Property at 2 Atherton Rd, Winchester, MA 01890, 6 beds, 6.5 baths

$3,295,000

6 beds6.5 baths6,100 sq ft

2 Atherton Rd, Winchester, MA 01890

Viewing page 3 of 16

Homes with Pools for Sale in Middlesex County

There are currently 655 homes with pools for sale in Middlesex County at a median listing price of $850K. 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 40 days and receive 3 offers. This map is refreshed with the newest listings in Middlesex County every 15 minutes.

In the past month, 1785 homes have been sold in Middlesex County. In addition to houses in Middlesex County, there were also 1154 condos, 555 townhouses, and 432 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, MA

Nearby Counties

Cities

Nearby Counties with Homes with Pools

Nearby Cities with Homes with Pools

More to explore in Middlesex County, MA

How to buy a house in Middlesex County, MA

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

43 Redfin agents serving Middlesex County

1045

Deals*

4.8

Satisfaction

8725

Homes closed*

* Data from the last year

Popular Markets in Massachusetts

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

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.