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:
Group showing Sunday, 10/18, 12 noon! Fantastic investment opportunity just minutes from Downtown Middletown! This beautifully maintained three-family property offers a great combination of location, condition, and long-term investment potential. All three units offer two large bedrooms. Each unit also enjoys its own private porch or balcony, giving tenants valuable outdoor space. This property has been well cared for with significant updates throughout, including impeccably updated mechanicals, helping take some of the worry out of owning a multifamily property. A three-car detached garage in the rear adds even more value, along with additional off-street parking. Located on a quiet, desir

$579,900

6 beds3 baths2,991 sq ft

225 Pearl St, Middletown, CT 06457

Private porch • Private balcony • Updated mechanicals

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Opportunity awaits at this 2-family residential property in a convenient Middletown location. The existing structure has sustained fire damage and is being offered strictly as-is. Ideal for investors, contractors, or buyers seeking a renovation or redevelopment project. Situated on a level lot with access to public water and public sewer. Close to shopping, dining, parks, and commuter routes. A unique chance to restore, reimagine, or rebuild subject to municipal approvals.

$75,000

5 beds3 baths1,558 sq ft

18 Portland St, Middletown, CT 06457

Public sewer • Level lot • Close to shopping

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Rare opportunity to own a hard to find multifamily in the beautiful town of Chester! This unique 2 unit property offers space, character and flexibility in a wonderful location, just a short drive to Cedar Lake and approximately a 15 minute walk to charming downtown Chester with its shops, restaurants and small town New England appeal. Unit 1 spans 3 levels and features 3 bedrooms, with 2 upstairs and 1 on the main level, 1.5 baths, hardwood floors, exposed beams in the living room and mini splits for heat and A/C. The half bath is ready to be completed, with the seller leaving the toilet, vanity and lighting for the next owner. Some windows have been replaced and the porch features new dec

$579,900

4 beds2.5 baths3,506 sq ft

84-86 Spring St, Chester, CT 06412

New decking on porch • 0.38 acre lot • Built 1800

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Welcome to 3 Anchorage Ln, a spacious colonial designed with the flexibility, comfort, and space to grow into for years to come. This 4-bedroom, 3-full-bath home offers 2,496 sqft with a thoughtful layout that works for everyday family life, entertaining, and working from home. The beautifully remodeled kitchen is the heart of the house, opening to the living and dining rooms and creating an inviting space for gatherings. The first floor offers a versatile den/family room, dedicated office space, full bath, and laundry room, providing plenty of options as your needs evolve. The office could easily serve as a first-floor bedroom, with the convenience of a full bathroom nearby. Upstairs, the

$749,000

4 beds3 baths2,496 sq ft

3 Anchorage Ln, Old Saybrook, CT 06475

Versatile den • Remodeled kitchen • Deeded access

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Welcome to 147 Ridge Rd, a stunning, completely remodeled home located in the highly desirable South Farms district of Middletown! This beautifully updated property has been renovated from top to bottom and is truly move-in ready. The heart of the home is the spectacular open-concept kitchen, featuring beautiful quartz countertops and seamless flow into a bright, light-filled living room with a decorative stone fireplace. Throughout the home, you'll find beautifully refinished hardwood floors and two beautifully updated bathrooms, each featuring elegant inlaid tile showers. The dining room features a slider to an impressive 16-foot deck, creating the perfect setting for indoor and outdoor e

$449,900

3 beds2 baths1,772 sq ft

147 Ridge Rd, Middletown, CT 06457

Open-concept kitchen • 16-foot deck • Inlaid tile showers

Property at 74 Grove St, Middletown, CT 06457, 4 beds, 2 baths

$365,000

4 beds2 baths2,035 sq ft

74 Grove St, Middletown, CT 06457

Property at 164 Airline Ave, Portland, CT 06480, 3 beds, 1.5 baths

$250,000

3 beds1.5 baths1,326 sq ft

164 Airline Ave, Portland, CT 06480

Property at 130 Spencer Dr, Middletown, CT 06457, 5 beds, 2 baths

$349,000

5 beds2 baths1,440 sq ft

130 Spencer Dr, Middletown, CT 06457

Property at 882 Killingworth Rd, Higganum, CT 06441, 4 beds, 3 baths

$620,000

4 beds3 baths2,286 sq ft

882 Killingworth Rd, Higganum, CT 06441

Property at 19 W Shore Dr, Clinton, CT 06413, 2 beds, 1.5 baths

$465,000

2 beds1.5 baths1,030 sq ft

19 W Shore Dr, Clinton, CT 06413

Property at 33 Little City Rd, Higganum, CT 06441, 2 beds, 2 baths

$799,000

2 beds2 baths2,454 sq ft

33 Little City Rd, Higganum, CT 06441

Property at 122 Newfield St Unit 3A, Middletown, CT 06457, 3 beds, 1.5 baths

$329,900

3 beds1.5 baths1,346 sq ft

122 Newfield St Unit 3A, Middletown, CT 06457

Property at 170 Old Post Rd, Old Saybrook, CT 06475, 3 beds, 2.5 baths

$900,000

3 beds2.5 baths2,128 sq ft

170 Old Post Rd, Old Saybrook, CT 06475

Property at 26 Chittenden Hill Rd, Westbrook, CT 06498, 4 beds, 2 baths

$825,000

4 beds2 baths2,820 sq ft

26 Chittenden Hill Rd, Westbrook, CT 06498

Property at 25 River Ave, Old Saybrook, CT 06475, 2 beds, 1 bath

$800,000

2 beds1 bath1,478 sq ft

25 River Ave, Old Saybrook, CT 06475

Property at 27 N Main St #8, Essex, CT 06426, 2 beds, 1 bath

$439,900

2 beds1 bath1,026 sq ft

27 N Main St #8, Essex, CT 06426

Property at 19 High St, Middlefield, CT 06455, 4 beds, 2.5 baths

$699,000

4 beds2.5 baths4,073 sq ft

19 High St, Middlefield, CT 06455

Property at 47 E Kings Hwy, Chester, CT 06412, 4 beds, 3.5 baths

$1,900,000

4 beds3.5 baths3,957 sq ft

47 E Kings Hwy, Chester, CT 06412

Property at 288 Middlesex Ave, Chester, CT 06412, 4 beds, 5 baths

$2,995,000

4 beds5 baths4,926 sq ft

288 Middlesex Ave, Chester, CT 06412

Property at 88 Main St, Ivoryton, CT 06442, 5 beds, 5.5 baths

$2,200,000

5 beds5.5 baths5,234 sq ft

88 Main St, Ivoryton, CT 06442

Property at 57 Grove St, Clinton, CT 06413, 2 beds, 1 bath

$444,900

2 beds1 bath957 sq ft

57 Grove St, Clinton, CT 06413

Property at 2 Hay Field Rd, East Haddam, CT 06415, 2 beds, 1 bath

$189,000

2 beds1 bath448 sq ft

2 Hay Field Rd, East Haddam, CT 06415

Property at 100 Pratt Rd, Clinton, CT 06413, 3 beds, 2 baths

$525,000

3 beds2 baths1,296 sq ft

100 Pratt Rd, Clinton, CT 06413

Property at 77 Main St, East Haddam, CT 06423, 4 beds, 4 baths

$1,550,000

4 beds4 baths4,070 sq ft

77 Main St, East Haddam, CT 06423

Property at 15 E Shore Dr, Colchester, CT 06415, 3 beds, 2 baths

$639,900

3 beds2 baths1,470 sq ft

15 E Shore Dr, Colchester, CT 06415

Property at 10 Scholes Ln, Essex, CT 06426, 5 beds, 4 baths

$3,595,000

5 beds4 baths3,769 sq ft

10 Scholes Ln, Essex, CT 06426

Property at 23 Plains Rd, Moodus, CT 06469, 9 beds, 7 baths

$895,000

9 beds7 baths5,444 sq ft

23 Plains Rd, Moodus, CT 06469

Property at 40 Beach Rd, Clinton, CT 06413, 2 beds, 1.5 baths

$220,000

2 beds1.5 baths1,056 sq ft

40 Beach Rd, Clinton, CT 06413

Property at 34 Fowler Ln, Middlefield, CT 06455, 2 beds, 1 bath

$634,900

2 beds1 bath1,008 sq ft

34 Fowler Ln, Middlefield, CT 06455

Property at 15 Mill Rock Rd W, Old Saybrook, CT 06475, 3 beds, 2 baths

$666,000

3 beds2 baths1,580 sq ft

15 Mill Rock Rd W, Old Saybrook, CT 06475

Property at 104 Higby Rd, Middletown, CT 06457, 3 beds, 1 bath

$399,999

3 beds1 bath1,112 sq ft

104 Higby Rd, Middletown, CT 06457

Property at 480 Main St, Middletown, CT 06457, 8 beds, 9 baths

$1,300,000

8 beds9 baths13,837 sq ft

480 Main St, Middletown, CT 06457

Property at 91 Sarah Baker Rd, East Haddam, CT 06423, 2 beds, 1.5 baths

$549,000

2 beds1.5 baths1,061 sq ft

91 Sarah Baker Rd, East Haddam, CT 06423

Property at 46 Main St, Centerbrook, CT 06409, 2 beds, 2 baths

$449,999

2 beds2 baths1,252 sq ft

46 Main St, Centerbrook, CT 06409

Property at 88 Powder Hill Rd, Middlefield, CT 06455, 4 beds, 2.5 baths

$749,900

4 beds2.5 baths2,458 sq ft

88 Powder Hill Rd, Middlefield, CT 06455

Property at 194 Liberty St, Middletown, CT 06457, 7 beds, 2 baths

$390,000

7 beds2 baths2,476 sq ft

194 Liberty St, Middletown, CT 06457

Property at 127 Shore Rd, Clinton, CT 06413, 8 beds, 3 baths

$2,400,000

8 beds3 baths2,709 sq ft

127 Shore Rd, Clinton, CT 06413

Property at 58 Middle Haddam Rd, Middle Haddam, CT 06456, 5 beds, 2 baths

$540,000

5 beds2 baths2,010 sq ft

58 Middle Haddam Rd, Middle Haddam, CT 06456

Property at 5 Joe Williams Rd, Moodus, CT 06469, 2 beds, 1 bath

$280,000

2 beds1 bath1,131 sq ft

5 Joe Williams Rd, Moodus, CT 06469

Property at 1445 Boston Post Rd, Old Saybrook, CT 06475, 4 beds, 1 bath

$12,000,000

4 beds1 bath2,059 sq ft

1445 Boston Post Rd, Old Saybrook, CT 06475

Property at 157 Evergreen Rd, Cromwell, CT 06416, 3 beds, 1.5 baths

$609,900

3 beds1.5 baths1,466 sq ft

157 Evergreen Rd, Cromwell, CT 06416

Viewing page 3 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.