Recently Sold Homes in Middlesex County, CT

572 homes

Sort:

Recommended

SOLD OCT 22, 2026

ABOUT THIS HOME
Recently Sold Home in Middlesex County, CT:
Contemporary coastal elegance meets remarkable privacy along South Cove in Old Saybrook. Set well back from the road on 1.8 acres, this distinctive 3,188-square-foot cedar-sided residence captures sweeping water views from nearly every room. Originally built in 1965 and completely rebuilt in 1991, the home was thoughtfully designed to embrace its spectacular setting, with vaulted ceilings, expansive windows, and seamless connections to the outdoors. The living room features custom built-ins, a gas fireplace, wet bar, and sliders to a spacious deck overlooking the cove. The kitchen flows into a vaulted family room and opens to a 300-square-foot enclosed porch-an inviting space for entertaini

$1,200,000 Last sold price

4 beds3 baths3,188 sq ft

108 Maple Ave, Old Saybrook, CT 06475

SOLD OCT 9, 2026

ABOUT THIS HOME
Recently Sold Home in Middlesex County, CT:
Welcome to the desirable Indiantown Beach community, where endless possibilities await. This well-loved home offers a spacious floor plan featuring a bright sunroom, generous family room with a floor-to-ceiling gas fireplace and built-ins, and a large primary suite with its full bath and own private deck. Ready for cosmetic updates, this home presents an excellent opportunity to create your dream beach retreat in one of Old Saybrook's most sought-after shoreline neighborhoods. Enjoy outdoor living with a spacious deck, large patio, fenced yard and storage shed-perfect for entertaining, gardening, or relaxing after a day at the beach. As a resident of Indiantown Beach, you'll enjoy access to

$685,000 Last sold price

2 beds2 baths1,760 sq ft

25 Uncas Trl, Old Saybrook, CT 06475

SOLD SEP 22, 2026

ABOUT THIS HOME
Recently Sold Home in Middlesex County, CT:
No stone was left unturned at this turn key beach house in the Chalker Beach Association! Completely and professionally renovated from bottom to top, this 3 bedroom cottage is open, light and airy and ready for you to move in, just in time for summer! A spacious living room opens into the lovely eat-in kitchen with custom cabinets, stainless steel appliances and beautiful crown moulding. A bright sunroom off the kitchen will be a great place to spend the afternoon reading a book and relaxing or a fun little playroom. On the other side of the house 3 bedrooms and 1.5 baths with a flexible laundry/mudroom are all fresh with beautiful finishes. The house is heated and cooled with all new split

$700,000 Last sold price

3 beds1.5 baths1,120 sq ft

52 Chalker Beach Rd, Old Saybrook, CT 06475

SOLD SEP 4, 2026

ABOUT THIS HOME
Recently Sold Home in Middlesex County, CT:
For the first time in generations this loved 3-bedroom ranch is available. It rests on a gentle knoll in the heart of the Chalker Beach community. Home has a full dry basement offering additional space for storage. One floor living, public water, central air, gleaming hardwood flooring throughout, sun filled bay windows, garden shed, open sunny lot, and new high efficiency propane furnace. Enclosed sunroom with glass windows and sliding glass door provides additional respite space. Chalker Beach remains one of Connecticut's sought-after private waterfront communities on Long Island Sound in Old Saybrook, Connecticut. Neighbors dating back for generations have chosen Chalker Beach-not just f

$550,000 Last sold price

3 beds1 bath960 sq ft

53 Chalker Beach Rd, Old Saybrook, CT 06475

SOLD AUG 27, 2026

ABOUT THIS HOME
Recently Sold Home in Middlesex County, CT:
Charming Coastal Ranch in an incredible Old Saybrook location! This well-maintained ranch offers the perfect blend of comfort, convenience, and shoreline lifestyle. An easy flow layout which includes 3 bedrooms, living room, dining room, kitchen, full bath and a full unfinished basement for additional storage or workshop. Step outside to a spacious backyard designed for entertaining, relaxing, and enjoying warm summer evenings. This home invites morning walks and evening strolls to Harvey's Beach, Saybrook town beach, Trask Park with a splash pad, and the shops and restaurants along Main Street. Whether you're heading out for dinner, catching the train, or enjoying a beach day, everything y

$500,000 Last sold price

3 beds1 bath1,038 sq ft

9 Farview Ave, Old Saybrook, CT 06475

Property at 100 Sheffield St Unit A2, Old Saybrook, CT 06475, 2 beds, 2.5 baths

$625,000 Last sold price

2 beds2.5 baths2,002 sq ft

100 Sheffield St Unit A2, Old Saybrook, CT 06475

Property at 61 Ingham Hill Rd, Old Saybrook, CT 06475, 1 bed, 1.5 baths

$365,000 Last sold price

1 bed1.5 baths1,205 sq ft

61 Ingham Hill Rd, Old Saybrook, CT 06475

Property at 2 Pheasant Hill Ln, Old Saybrook, CT 06475, 4 beds, 3 baths

$746,000 Last sold price

4 beds3 baths2,474 sq ft

2 Pheasant Hill Ln, Old Saybrook, CT 06475

Property at 22 Beaver Dam Trl, Old Saybrook, CT 06475, 4 beds, 2.5 baths

$625,000 Last sold price

4 beds2.5 baths1,934 sq ft

22 Beaver Dam Trl, Old Saybrook, CT 06475

Property at 92 Bokum Rd, Old Saybrook, CT 06475, 2 beds, 1.5 baths

$525,000 Last sold price

2 beds1.5 baths1,376 sq ft

92 Bokum Rd, Old Saybrook, CT 06475

Property at 34 Briarcliffe Trl, Old Saybrook, CT 06475, 4 beds, 3 baths

$875,000 Last sold price

4 beds3 baths3,720 sq ft

34 Briarcliffe Trl, Old Saybrook, CT 06475

Property at 41 Watrous Point Rd, Old Saybrook, CT 06475, 6 beds, 4.5 baths

$3,750,000 Last sold price

6 beds4.5 baths5,536 sq ft

41 Watrous Point Rd, Old Saybrook, CT 06475

Property at 37 Woodland Dr, Old Saybrook, CT 06475, 3 beds, 2 baths

$999,000 Last sold price

3 beds2 baths1,426 sq ft

37 Woodland Dr, Old Saybrook, CT 06475

Property at 11 Fencove Ct, Old Saybrook, CT 06475, 4 beds, 2.5 baths

$1,692,034 Last sold price

4 beds2.5 baths3,515 sq ft

11 Fencove Ct, Old Saybrook, CT 06475

Property at 9 Barley Hill Rd, Old Saybrook, CT 06475, 4 beds, 3.5 baths

$700,000 Last sold price

4 beds3.5 baths3,544 sq ft

9 Barley Hill Rd, Old Saybrook, CT 06475

Property at 25 Sheffield St #7, Old Saybrook, CT 06475, 2 beds, 3 baths

$960,000 Last sold price

2 beds3 baths2,151 sq ft

25 Sheffield St #7, Old Saybrook, CT 06475

Property at 2 Iris Ct, Cromwell, CT 06416, 3 beds, 3 baths

$885,000 Last sold price

3 beds3 baths2,727 sq ft

2 Iris Ct, Cromwell, CT 06416

Property at 8 Grove Ter, Westbrook, CT 06498, 2 beds, 1.5 baths

$184,000 Last sold price

2 beds1.5 baths780 sq ft

8 Grove Ter, Westbrook, CT 06498

Property at 170 Rising Trail Dr #170, Middletown, CT 06457, 3 beds, 1.5 baths

$165,000 Last sold price

3 beds1.5 baths1,120 sq ft

170 Rising Trail Dr #170, Middletown, CT 06457

Property at 15 Willow Ct #15, Cromwell, CT 06416, 2 beds, 1.5 baths

$260,000 Last sold price

2 beds1.5 baths1,368 sq ft

15 Willow Ct #15, Cromwell, CT 06416

Redfin Corporation

Property at 2324 Cromwell Hills Dr #2324, Cromwell, CT 06416, 2 beds, 1.5 baths

$178,000 Last sold price

2 beds1.5 baths1,057 sq ft

2324 Cromwell Hills Dr #2324, Cromwell, CT 06416

Property at 84 Founders Vlg #84, Clinton, CT 06413, 2 beds, 1 bath

$269,000 Last sold price

2 beds1 bath1,024 sq ft

84 Founders Vlg #84, Clinton, CT 06413

Property at 1 Avon Dale Rd #1, Cromwell, CT 06416, 1 bed, 1 bath

$260,000 Last sold price

1 bed1 bath908 sq ft

1 Avon Dale Rd #1, Cromwell, CT 06416

Property at 88 Woodland Dr #88, Cromwell, CT 06416, 2 beds, 2 baths

$200,000 Last sold price

2 beds2 baths979 sq ft

88 Woodland Dr #88, Cromwell, CT 06416

Property at 10 Valley Run Dr #10, Cromwell, CT 06416, 3 beds, 1.5 baths

$325,000 Last sold price

3 beds1.5 baths1,708 sq ft

10 Valley Run Dr #10, Cromwell, CT 06416

Property at 93 Carriage Crossing Ln #93, Middletown, CT 06457, 2 beds, 2 baths

$195,000 Last sold price

2 beds2 baths866 sq ft

93 Carriage Crossing Ln #93, Middletown, CT 06457

Property at 33 Woodbridge Ln #33, Cromwell, CT 06416, 2 beds, 2.5 baths

$340,000 Last sold price

2 beds2.5 baths1,744 sq ft

33 Woodbridge Ln #33, Cromwell, CT 06416

Property at 341 Lake Shore Dr, East Haddam, CT 06423, 3 beds, 2.5 baths

$479,000 Last sold price

3 beds2.5 baths1,666 sq ft

341 Lake Shore Dr, East Haddam, CT 06423

Property at 34-R Goldfinch Rd, Durham, CT 06422, 4 beds, 2.5 baths

$662,500 Last sold price

4 beds2.5 baths3,526 sq ft

34-R Goldfinch Rd, Durham, CT 06422

Property at 16 Glen Grove Rd, Deep River, CT 06417, 4 beds, 2.5 baths

$850,000 Last sold price

4 beds2.5 baths2,782 sq ft

16 Glen Grove Rd, Deep River, CT 06417

Property at 13-A Cove St, Old Saybrook, CT 06475, 2 beds, 1 bath

$717,500 Last sold price

2 beds1 bath960 sq ft

13-A Cove St, Old Saybrook, CT 06475

Property at 26 Mystique Ln #26, Cromwell, CT 06416, 2 beds, 2.5 baths

$592,500 Last sold price

2 beds2.5 baths1,512 sq ft

26 Mystique Ln #26, Cromwell, CT 06416

Property at 9 Sandy Brook Rd #2, Clinton, CT 06413, 3 beds, 2.5 baths

$300,000 Last sold price

3 beds2.5 baths1,235 sq ft

9 Sandy Brook Rd #2, Clinton, CT 06413

Property at 5 Carriage Crossing Ln #5, Middletown, CT 06457, 2 beds, 2 baths

$227,000 Last sold price

2 beds2 baths840 sq ft

5 Carriage Crossing Ln #5, Middletown, CT 06457

Property at 9 Freya Ln, East Hampton, CT 06424, 4 beds, 2.5 baths

$687,137 Last sold price

4 beds2.5 baths2,200 sq ft

9 Freya Ln, East Hampton, CT 06424

Property at 2 Old South Cove Rd, Old Saybrook, CT 06475, 3 beds, 3.5 baths

$1,475,000 Last sold price

3 beds3.5 baths2,472 sq ft

2 Old South Cove Rd, Old Saybrook, CT 06475

Property at 151 E Main St #9, Clinton, CT 06413, 3 beds, 2.5 baths

$709,000 Last sold price

3 beds2.5 baths2,200 sq ft

151 E Main St #9, Clinton, CT 06413

Property at 3 Essex Sq, Essex, CT 06426, 1.5 baths

$832,500 Last sold price

— beds1.5 baths4,544 sq ft

3 Essex Sq, Essex, CT 06426

Property at 11a/11b Pond Circle Rd, Westbrook, CT 06498, 4 beds, 3 baths

$655,000 Last sold price

4 beds3 baths2,761 sq ft

11a/11b Pond Circle Rd, Westbrook, CT 06498

Property at 37 Arkona Dr, Higganum, CT 06441, 4 beds, 2.5 baths

$780,000 Last sold price

4 beds2.5 baths2,500 sq ft

37 Arkona Dr, Higganum, CT 06441

Property at 11 Priorwood Gdns #11, Cromwell, CT 06416, 3 beds, 3 baths

$865,000 Last sold price

3 beds3 baths3,734 sq ft

11 Priorwood Gdns #11, Cromwell, CT 06416

Viewing page 14 of 14

Recently Sold Homes in Middlesex County

There are currently 572 recently sold homes for sale in Middlesex 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 Middlesex County stay on the market for 47 days and receive 4 offers. This map is refreshed with the newest listings in Middlesex County every 15 minutes.

In the past month, 196 homes have been sold in Middlesex County. In addition to houses in Middlesex County, there were also 115 condos, 0 townhouses, and 32 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

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

Buy the right home at the right price near Middlesex County with a local Redfin real estate agent.

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

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.

Recently Sold Homes in Middlesex County, CT

Recently Sold Homes in Middlesex County

More real estate resources for Middlesex County, CT

Nearby Counties

Cities

Nearby Counties with Recently Sold Homes

More to explore in Middlesex County, CT

How to buy a house in Middlesex County, CT

Popular Markets in Connecticut