NOMADEReal Estate
$1M+ Properties

Luxury Homes in Middlesex County, CT

138 active listings on the market right now

Browse current luxury homes in Middlesex County, CT. Middlesex County is one of Connecticut's hidden gems, centered on the Connecticut River as it winds toward Long Island Sound. The county seat of Middletown, home to Wesleyan University, is a lively small city with a thriving Main Street, diverse dining options, and a creative ene Median home prices in Middlesex County run around $350,000, with significant variation by town. Use the listings below to see what's actually available right now and click through for full details.

Active Listings

Available Luxury Homes in Middlesex County

9 Bellstone AvenueActiveSingle Family For Sale
$1,000,000

9 Bellstone Avenue

Westbrook, Connecticut 06498

3 bd
3 ba
2,182 sqft
104 Knollwood DriveActiveSingle Family For Sale
$1,495,000

104 Knollwood Drive

Old Saybrook, Connecticut 06475

3 bd
2 ba
1,809 sqft
96 Ayers Point RoadActiveSingle Family For Sale
$1,099,000

96 Ayers Point Road

Old Saybrook, Connecticut 06475

4 bd
3 ba
4,109 sqft
24 Shore DriveActiveSingle Family For Sale
$1,245,000

24 Shore Drive

Old Saybrook, Connecticut 06475

3 bd
1 ba
884 sqft
26 Willard AvenueActiveSingle Family For Sale
$1,175,000

26 Willard Avenue

Old Saybrook, Connecticut 06475

3 bd
2 ba
2,904 sqft
288 Middlesex AvenueActiveSingle Family For Sale
$2,995,000

288 Middlesex Avenue

Chester, Connecticut 06412

4 bd
6 ba
4,926 sqft
145 Monarca DriveActiveSingle Family For Sale
$1,200,000

145 Monarca Drive

Middletown, Connecticut 06457

3 bd
4 ba
3,456 sqft
2 Captains LaneActiveSingle Family For Sale
$2,899,900

2 Captains Lane

Old Saybrook, Connecticut 06475

5 bd
5 ba
5,062 sqft
11 Fencove CourtActiveSingle Family For Sale
$1,699,000

11 Fencove Court

Old Saybrook, Connecticut 06475

4 bd
3 ba
3,515 sqft
17 College StreetActiveSingle Family For Sale
$1,099,000

17 College Street

Old Saybrook, Connecticut 06475

3 bd
3 ba
1,960 sqft
323 River RoadActiveSingle Family For Sale
$3,950,000

323 River Road

Deep River, Connecticut 06417

5 bd
6 ba
5,557 sqft
575 Main Street 3ActiveCommercial For Sale
$1,350,000

575 Main Street 3

Middletown, Connecticut 06457

0 bd
2 ba
7,814 sqft
25 Silver Springs DriveActiveSingle Family For Sale
$1,250,000

25 Silver Springs Drive

Haddam, Connecticut 06441

5 bd
4 ba
3,689 sqft
880 Boston Post RoadActiveCommercial For Sale
$1,500,000

880 Boston Post Road

Old Saybrook, Connecticut 06475

0 bd
1 ba
13,836 sqft
1270 Saybrook RoadActiveSingle Family For Sale
$1,400,000

1270 Saybrook Road

Haddam, Connecticut 06438

3 bd
3 ba
3,375 sqft
47 Kings HighwayActiveSingle Family For Sale
$2,200,000

47 Kings Highway

Chester, Connecticut 06412

4 bd
4 ba
3,957 sqft
88 Main StreetActiveSingle Family For Sale
$2,200,000

88 Main Street

Essex, Connecticut 06442

5 bd
6 ba
5,234 sqft
180 Green Hill RoadActiveSingle Family For Sale
$1,299,900

180 Green Hill Road

Killingworth, Connecticut 06419

4 bd
4 ba
4,154 sqft
18 Birch Mill RoadActiveSingle Family For Sale
$2,195,000

18 Birch Mill Road

Killingworth, Connecticut 06419

4 bd
3 ba
3,700 sqft
21 Clarkson LaneActiveSingle Family For Sale
$2,250,000

21 Clarkson Lane

Killingworth, Connecticut 06419

5 bd
6 ba
4,190 sqft
8 Route 80ActiveCommercial For Sale
$1,799,000

8 Route 80

Killingworth, Connecticut 06419

0 bd
0 ba
18,500 sqft
28 River RoadActiveSingle Family For Sale
$1,650,000

28 River Road

Essex, Connecticut 06426

3 bd
3 ba
2,359 sqft
46 West AvenueActiveSingle Family For Sale
$1,595,000

46 West Avenue

Essex, Connecticut 06426

3 bd
3 ba
2,708 sqft
37 Woodland DriveActiveSingle Family For Sale
$1,025,000

37 Woodland Drive

Old Saybrook, Connecticut 06475

3 bd
2 ba
1,426 sqft
FAQ

Frequently asked questions

How many luxury homes are currently for sale in Middlesex County, CT?

Active inventory in Middlesex County, CT changes daily as listings come on and go off market. The grid above shows the most recently updated listings — refresh for the latest count.

What is the median home price in Middlesex County, CT?

The median home price in Middlesex County, CT is approximately $350,000. Actual sale prices depend on location, condition, lot size, and timing of the listing.

What are property taxes like in Middlesex County, CT?

Connecticut property taxes are levied by individual municipalities via a mill rate × 70% of assessed value. Mill rates vary widely — from around 11 in low-tax shoreline towns to 70+ in some cities.

Can Nomade Real Estate help me buy a home in Middlesex County, CT?

Yes. Nomade represents buyers across all eight Connecticut counties with on-the-ground knowledge of Middlesex County, CT pricing, schools, commute, and what makes each neighborhood different. Reach out via the contact form on any property page to start a search.

Looking in Middlesex County?

Talk to a Nomade agent who actually knows Middlesex County— pricing, schools, taxes, and what's not on the MLS yet.