Vintage homes for sale & real estate in Middlesex County, CT

137 homes

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Investors, take notice!! An incredible opportunity to get into a lake property on almost a full acre in East Haddam. Located on beautiful Lake Hayward with incredible lake views and lake rights. Great opportunity for an owner or investor to make it their own.

$199,000

3 beds1 bath950 sq ft

51 Hungerford Rd E, East Haddam, CT 06423

Lake views • Lake property • Lake rights

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Open house November 4th 5pm-6pm Welcome to 9 Burr Avenue! This charming Colonial offers 3 bedrooms, 1 full bathroom, and 1,344 square feet of living space per public records. The home features a recently remodeled kitchen, updated within the past year, along with a finished walk-up attic that provides versatile additional space, ideal for a home office, hobby room, or bonus area. Additional improvements include a newer hot water heater, approximately one year old. Outside, enjoy a fully fenced backyard offering privacy and plenty of room for entertaining, outdoor gathering, or simply relaxing. This home is ready for its new owners! Property is being sold AS-IS

$314,900

3 beds1 bath1,344 sq ft

9 Burr Ave, Middletown, CT 06457

Remodeled kitchen • 2,178 sq ft lot • Built 1900

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Antique 4 Bedroom colonial just steps to the CT River and a short walk to town. First floor bedroom and full bath. Small manageble yard. 1 Car Detached oversized garage. Distance from school. Great potential. Generator hook up. Needs work. Ready for your updating!

$299,900

4 beds1 bath1,274 sq ft

147 River St, Deep River, CT 06417

Full bath • Generator hook up • First floor bedroom

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Just a quick stroll from the heart of Chester Village, this absolutely charming three-bedroom, one-bath home offers a wonderful combination of classic character, recent improvements, and an exceptional location. From the moment you arrive, the inviting enclosed front porch welcomes you, providing additional living space and a wonderful spot to relax. Inside, the home retains much of its original charm, with beautiful hardwood floors, rich wood moldings throughout, and a lovely built-in corner hutch in the dining room. The kitchen has been updated from its original design, offering modern convenience while complementing the home's character. Recent improvements in 2026 include a freshly pain

$450,000

3 beds1 bath1,179 sq ft

6 School Ln, Chester, CT 06412

Updated kitchen • Walk-up attic • Hardwood floors

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
2 Plots sold together- 7 & 18 Toms Rd. Rare opportunity to own a slice of CT shoreline! Tucked away at the end of a private road, this charming seasonal waterfront cottage offers water on 2 sides, water views on 3, private beach, backyard dock & breathtaking sunsets. Cherished by the same family for generations, this special coastal retreat captures everything there is to love about beach living. Recently refreshed with new flooring, new granite counters, new hot water heater and electrical updates. The cottage features an inviting open floor plan, flexible sleeping accommodations with convenient convertible beds & a spectacular enclosed front porch where you can relax, en

$1,200,000

2 beds0.5 baths624 sq ft

7 Toms Rd, Old Saybrook, CT 06475

Backyard dock • Water views • Private beach

Property at 206 W Elm St, Deep River, CT 06417, 2 beds, 1.5 baths

$358,900

2 beds1.5 baths1,134 sq ft

206 W Elm St, Deep River, CT 06417

Property at 50 Smith St, East Hampton, CT 06424, 3 beds, 2 baths

$479,000

3 beds2 baths2,992 sq ft

50 Smith St, East Hampton, CT 06424

Property at 26 Powerhouse Rd, Moodus, CT 06469, 3 beds, 1 bath

$299,000

3 beds1 bath1,504 sq ft

26 Powerhouse Rd, Moodus, CT 06469

Property at 360 Chauncey Rd, Middletown, CT 06457, 3 beds, 2 baths

$345,000

3 beds2 baths1,201 sq ft

360 Chauncey Rd, Middletown, CT 06457

Property at 1511 Country Club Rd, Middletown, CT 06457, 4 beds, 2 baths

$410,000

4 beds2 baths3,319 sq ft

1511 Country Club Rd, Middletown, CT 06457

Property at 511 Route 81, Killingworth, CT 06419, 2 beds, 2 baths

$699,000

2 beds2 baths1,386 sq ft

511 Route 81, Killingworth, CT 06419

Property at 368 Bow Ln, Middletown, CT 06457, 2 beds, 1 bath

$399,000

2 beds1 bath1,205 sq ft

368 Bow Ln, Middletown, CT 06457

Property at 3 Town Beach Rd, Old Saybrook, CT 06475, 4 beds, 2.5 baths

$839,000

4 beds2.5 baths3,472 sq ft

3 Town Beach Rd, Old Saybrook, CT 06475

Property at 39 Falls Rd, Moodus, CT 06469, 3 beds, 1.5 baths

$469,999

3 beds1.5 baths2,534 sq ft

39 Falls Rd, Moodus, CT 06469

Property at 9 Magnolia Ave, Middletown, CT 06457, 4 beds, 1 bath

$285,000

4 beds1 bath1,440 sq ft

9 Magnolia Ave, Middletown, CT 06457

Property at 28 Blake St, Ivoryton, CT 06442, 2 beds, 1.5 baths

$389,000

2 beds1.5 baths948 sq ft

28 Blake St, Ivoryton, CT 06442

Property at 8 Prospect St, Essex, CT 06426, 3 beds, 1.5 baths

$999,000

3 beds1.5 baths2,287 sq ft

8 Prospect St, Essex, CT 06426

Property at 33 N High St, Clinton, CT 06413, 3 beds, 2.5 baths

$475,000

3 beds2.5 baths3,032 sq ft

33 N High St, Clinton, CT 06413

Property at 25 Spring St, Portland, CT 06480, 3 beds, 1.5 baths

$270,000

3 beds1.5 baths1,536 sq ft

25 Spring St, Portland, CT 06480

Property at 52 Anthony Ln, Westbrook, CT 06498, 3 beds, 1.5 baths

$422,377

3 beds1.5 baths914 sq ft

52 Anthony Ln, Westbrook, CT 06498

Property at Undisclosed address, East Hampton, CT 06424, 3 beds, 1.5 baths

$239,900

3 beds1.5 baths1,454 sq ft

Undisclosed address, East Hampton, CT 06424

Property at 30 Smith St, East Hampton, CT 06424, 2 beds, 1.5 baths

$409,000

2 beds1.5 baths1,434 sq ft

30 Smith St, East Hampton, CT 06424

Property at 7 Oakum Dock Rd, East Hampton, CT 06414, 2 beds, 1 bath

$339,900

2 beds1 bath1,396 sq ft

7 Oakum Dock Rd, East Hampton, CT 06414

Property at 388 E Haddam Moodus Rd, Moodus, CT 06469, 4 beds, 2 baths

$399,000

4 beds2 baths1,848 sq ft

388 E Haddam Moodus Rd, Moodus, CT 06469

Property at 11 Autumn Ln, Clinton, CT 06413, 3 beds, 2 baths

$580,000

3 beds2 baths2,508 sq ft

11 Autumn Ln, Clinton, CT 06413

Property at 32 Bushy Hill Rd, Ivoryton, CT 06442, 3 beds, 1 bath

$449,000

3 beds1 bath992 sq ft

32 Bushy Hill Rd, Ivoryton, CT 06442

Property at 106 S Front St, Middletown, CT 06457, 3 beds, 2 baths

$319,999

3 beds2 baths1,109 sq ft

106 S Front St, Middletown, CT 06457

Property at 110 East Main St, Clinton, CT 06413, 3 beds, 1.5 baths

$170,000

3 beds1.5 baths1,238 sq ft

110 East Main St, Clinton, CT 06413

Property at 10 Main St, Essex, CT 06426, 3 beds, 1.5 baths

$379,900

3 beds1.5 baths1,456 sq ft

10 Main St, Essex, CT 06426

Property at 18 Lakewood Rd, East Hampton, CT 06424, 5 beds, 2.5 baths

$429,900

5 beds2.5 baths1,582 sq ft

18 Lakewood Rd, East Hampton, CT 06424

Property at 1040 Washington St, Middletown, CT 06457, 3 beds, 1 bath

$460,000

3 beds1 bath1,964 sq ft

1040 Washington St, Middletown, CT 06457

Property at 10 Walnut Ave, East Hampton, CT 06424, 2 beds, 1 bath

$269,900

2 beds1 bath1,206 sq ft

10 Walnut Ave, East Hampton, CT 06424

Property at 4 Gates Way, Haddam, CT 06438, 4 beds, 2 baths

$499,000

4 beds2 baths2,100 sq ft

4 Gates Way, Haddam, CT 06438

Property at 263 Seaside Ave, Westbrook, CT 06498, 4 beds, 4 baths

$2,275,000

4 beds4 baths2,065 sq ft

263 Seaside Ave, Westbrook, CT 06498

Property at 65 Highland Ave, Middletown, CT 06457, 3 beds, 2 baths

$399,000

3 beds2 baths1,793 sq ft

65 Highland Ave, Middletown, CT 06457

Property at 61 BAILEY Rd, East Haddam, CT 06423, 1 bed, 1 bath

$215,000

1 bed1 bath480 sq ft

61 BAILEY Rd, East Haddam, CT 06423

Property at 2 Nooks Hill Rd, Cromwell, CT 06416, 6 beds, 2 baths

$250,000

6 beds2 baths2,558 sq ft

2 Nooks Hill Rd, Cromwell, CT 06416

Property at 477 Hunting Hill Ave, Middletown, CT 06457, 4 beds, 2.5 baths

$349,900

4 beds2.5 baths2,572 sq ft

477 Hunting Hill Ave, Middletown, CT 06457

Property at 39 Grove Rd, Cromwell, CT 06416, 2 beds, 1 bath

$329,900

2 beds1 bath792 sq ft

39 Grove Rd, Cromwell, CT 06416

Property at 57 Shore Rd, East Haddam, CT 06423, 2 beds, 2 baths

$675,000

2 beds2 baths1,856 sq ft

57 Shore Rd, East Haddam, CT 06423

Property at 66 Durant St, Middletown, CT 06457, 3 beds, 2 baths

$379,999

3 beds2 baths1,848 sq ft

66 Durant St, Middletown, CT 06457

Viewing page 1 of 4

Vintage Homes for Sale in Middlesex County

There are currently 137 vintage 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

Nearby Counties

Cities

Nearby Counties with Vintage Homes

Nearby Cities with Vintage Homes

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.