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

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ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Calling all INVESTORS and BOATERS, as well as anyone else willing to give this cozy nest some TLC! Situated walking distance to the NEW River Bend Landing, a short distance to Birdon Marina and a hop, skip and a jump to the Members-Only Meriden Motor Boat Club, all this home needs, is a vision to bring this Cape to life! Brand new furnace and all new pipes; half bathroom has started a transformation to a full 2nd bathroom; the primary bedroom has potential for a walk-in closet/office/additional space and the full bathroom, on the upper level by the main bedrooms, has been updated!

$250,000

3 beds1.5 baths1,326 sq ft

Brand new furnace • All new pipes • 0.34 acre lot

164 Airline Ave, Portland, CT 06480

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Super cute and ready for new owners, this home has been lovingly renovated and updated. Great location south of RTE 1; walk to shops and restaurants and a short drive to the wonderful Clinton Town Beach! Recent updates include new roof, gutters, windows, carpeting. Stunning new kitchen with beautiful tile floor and backsplash accents; stainless appliances, new slider to brand new back deck and lovely fenced yard. The living room has hardwood floors, new front door and pretty picture window ~ this home is loaded with light! There are two bedrooms on the first floor along with a full bath, and two bedrooms on the second floor plus full bath. There is a drive under garage with electric garage

$424,900

4 beds2 baths1,284 sq ft

Renovated • New kitchen • Updated

10 Beach Park Rd, Clinton, CT 06413

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
There's something special about an antique Colonial, and 137 Parmelee Road in Durham is a wonderful example of timeless character paired with the updates you want today. This charming home offers 3 bedrooms in the main residence plus a legal 1 bedroom accessory apartment, creating incredible flexibility for extended family, guests, rental income, or a private space of your own. The main house has a kitchen with washer & dryer in it, dining room and spacious livingroom on the 1st floor and upstairs there are 3 BRs and a Full bath and a walk up to the floored attic for storage. The apartment has an eatin kitchen with washer and dryer hookups, livingroom and BR on the 1st floor and 2 add

$424,900

4 beds2 baths2,479 sq ft

Eatin kitchen • Washer dryer hookups • Antique colonial

137 Parmelee Hill Rd, Durham, CT 06422

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Rare opportunity to own directly on the water in the heart of Chester. This 1950-built ranch offers 1,034 sq ft with a flexible layout - currently set up as a 1-bedroom, the spacious family room (10'3" x 20'10") could easily convert to a second bedroom or home office. The oversized living room (13'6" x 20'10") anchors the home, while the combined kitchen/dining area (10'5" x 16'2") and comfortable primary bedroom round out the interior. Step outside to direct river frontage with sweeping water views and endless potential for outdoor living on the riverbank. All of this just a short stroll from downtown Chester's boutiques, galleries, and acclaimed restaurants.

$269,900

1 bed1 bath1,034 sq ft

Flexible layout • Outdoor living • Sweeping water views

90 Water St, Chester, CT 06412

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
* * Multiple Offers, Highest and Best Due EOD Wednesday, 9/9/26 * * Opportunity knocks in the heart of Middletown! This two-family home sits just minutes from Route 9, public transportation, and the Main Street corridor with its restaurants, shops, and year-round events. Live in one unit and have a tenant help pay your mortgage, or add a solid two-family to the portfolio - a great fit for owner-occupants and investors alike. Unit 1 has been freshly updated with new flooring, fresh paint, an updated kitchen and bath, and ceiling fans. Unit 2 offers a functional layout with an enclosed sun porch and its own private entry. Separate utilities, including two electrical panels and two heating

$309,900

5 beds2 baths1,576 sq ft

Separate utilities • Off street parking • Updated kitchen

105 Spring St, Middletown, CT 06457

Property at 46 Middlefield St, Middletown, CT 06457, 3 beds, 2 baths

$369,900

3 beds2 baths1,236 sq ft

46 Middlefield St, Middletown, CT 06457

Property at 157 Baileyville Rd, Middlefield, CT 06455, 4 beds, 4 baths

$699,900

4 beds4 baths1,871 sq ft

157 Baileyville Rd, Middlefield, CT 06455

Property at 100 Jacobs Ter, Middletown, CT 06457, 3 beds, 1 bath

$339,900

3 beds1 bath1,071 sq ft

100 Jacobs Ter, Middletown, CT 06457

Property at 394 Main St, Portland, CT 06480, 4 beds, 3 baths

$477,500

4 beds3 baths2,866 sq ft

394 Main St, Portland, CT 06480

Property at 98 Maple Rd, Portland, CT 06480, 4 beds, 2.5 baths

$450,000

4 beds2.5 baths2,916 sq ft

98 Maple Rd, Portland, CT 06480

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

$489,900

2 beds1 bath1,026 sq ft

27 N Main St #8, Essex, CT 06426

Property at 3 Edwards Rd, Portland, CT 06480, 3 beds, 1 bath

$375,000

3 beds1 bath1,602 sq ft

3 Edwards Rd, Portland, CT 06480

Property at 74 Grove St, Middletown, CT 06457, 6 beds, 2 baths

$385,000

6 beds2 baths2,035 sq ft

74 Grove 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 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

Property at 49 Essex St, Deep River, CT 06417, 3 beds, 1 bath

$399,900

3 beds1 bath1,104 sq ft

49 Essex St, Deep River, CT 06417

Property at 4 Pine Pl, Clinton, CT 06413, 4 beds, 2 baths

$699,900

4 beds2 baths1,833 sq ft

4 Pine Pl, Clinton, CT 06413

Property at 92 Water St, Chester, CT 06412, 3 beds, 1 bath

$284,900

3 beds1 bath1,217 sq ft

92 Water St, Chester, CT 06412

Property at 149 Liberty St, Clinton, CT 06413, 3 beds, 2 baths

$479,900

3 beds2 baths1,520 sq ft

149 Liberty St, Clinton, CT 06413

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 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 104 Bell St, Middletown, CT 06457, 4 beds, 2 baths

$425,000

4 beds2 baths1,352 sq ft

104 Bell St, Middletown, CT 06457

Property at 25 Uncas Trl, Old Saybrook, CT 06475, 2 beds, 2 baths

$750,000

2 beds2 baths1,760 sq ft

25 Uncas Trl, Old Saybrook, CT 06475

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

$999,000

3 beds2.5 baths2,128 sq ft

170 Old Post Rd, Old Saybrook, CT 06475

Property at 21 Hickory Ln, East Haddam, CT 06423, 3 beds, 1.5 baths

$799,000

3 beds1.5 baths1,649 sq ft

21 Hickory Ln, East Haddam, CT 06423

Property at 104 Knollwood Dr, Old Saybrook, CT 06475, 3 beds, 2 baths

$1,445,000

3 beds2 baths1,809 sq ft

104 Knollwood Dr, Old Saybrook, CT 06475

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

$190,000

3 beds1.5 baths1,238 sq ft

110 East Main St, Clinton, CT 06413

Property at 17&21 Winter Ave, Deep River, CT 06417, 2 beds, 1.5 baths

$289,900

2 beds1.5 baths1,061 sq ft

17&21 Winter Ave, Deep River, CT 06417

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

$840,000

2 beds2 baths2,454 sq ft

33 Little City Rd, Higganum, CT 06441

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

$450,000

2 beds2 baths3,319 sq ft

1511 Country Club Rd, Middletown, CT 06457

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

$749,000

4 beds2.5 baths4,073 sq ft

19 High St, Middlefield, CT 06455

Property at 27 Bevin Blvd, East Hampton, CT 06424, 3 beds, 1.5 baths

$389,900

3 beds1.5 baths1,305 sq ft

27 Bevin Blvd, East Hampton, CT 06424

Property at 128 Killingworth Rd, Higganum, CT 06441, 3 beds, 2.5 baths

$629,000

3 beds2.5 baths2,577 sq ft

128 Killingworth Rd, Higganum, CT 06441

Property at 45 Main St, Essex, CT 06442, 3 beds, 3 baths

$759,900

3 beds3 baths2,456 sq ft

45 Main St, Essex, CT 06442

Property at 126 Main St, East Hampton, CT 06424, 4 beds, 3 baths

$650,000

4 beds3 baths2,275 sq ft

126 Main St, East Hampton, CT 06424

Property at 11 Jobs Gate 1, Portland, CT 06480, 2 beds, 1 bath

$299,000

2 beds1 bath732 sq ft

11 Jobs Gate 1, Portland, CT 06480

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 93 Book Hill Rd, Essex, CT 06426, 3 beds, 2.5 baths

$374,999

3 beds2.5 baths1,572 sq ft

93 Book Hill Rd, Essex, CT 06426

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

$1,025,000

3 beds2 baths1,426 sq ft

37 Woodland Dr, Old Saybrook, CT 06475

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

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Vintage Homes for Sale in Middlesex County

There are currently 139 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, 185 homes have been sold in Middlesex County. In addition to houses in Middlesex County, there were also 100 condos, 0 townhouses, and 29 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.

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