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:
Two hours from New York City. Two hours from Boston. A world away from both. Privacy is the ultimate luxury. This masterfully re-imagined 5,234 sq. ft. compound located in historic Ivoryton, a village within the town of Essex, sits behind newly established hedges on nearly two flat, manicured acres - completely turn-key, completely private. The grounds are designed for outdoor living. A 20 X 40 gunite pool flows into a hydrangea-framed landscape. Three bluestone patios for entertaining, dining, and quiet retreat. A newly built two-car garage, wired with new electrical and EV charger-ready. Inside, the transformation is total. A chef's kitchen built around a custom black cherry island with S

$2,200,000

5 beds5.5 baths5,234 sq ft

88 Main St, Ivoryton, CT 06442

20 x 40 gunite pool • Manicured acres • Bluestone patios

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Perched over the CT River on one of the largest lots on Main, the David Watrous House offers water views from each room. This 1850 architectural treasure offers over 4,000 square feet of living space, plus an additional 1,500+ square foot walkout lower level. A detached oversized 3-bay post-and-beam carriage house offers exceptional workshop/studio space, stained glass windows and crowned by a copper cupola with antique weathervane. A side porch entry leads to chef's kitchen with handcrafted Vermont solid cherry cabinetry, granite countertops, stainless appliances, a tin ceiling and dramatic 10-foot island. Formal dining with antique chandelier and fireplace make for elevated home entertain

$1,550,000

4 beds4 baths4,070 sq ft

77 Main St, East Haddam, CT 06423

River-facing kitchen • Granite countertops • Copper cupola

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ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
1/2 mile walk to Essex Village, the marina, shops, and restaurants, this historic residence is nestled within one of Essex's most desirable neighborhoods. Thoughtfully reimagined by an established interior designer, the home masterfully blends modern luxury with the timeless charm quintessential to Essex. Original architectural details including hand-carved doors, staircase banister, fireplace mantels, and crown molding have been carefully preserved and elevated, honoring the home's history while seamlessly integrating refined contemporary finishes. Rare for a home of its era, the property offers an open floor plan, soaring 8 foot ceilings, and oversized windows that flood every room with n

$1,595,000

3 beds2.5 baths2,708 sq ft

46 West Ave, Essex, CT 06426

Open floor plan • Historic residence • Soaking tub

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want to walk away from; there's also sliders to the deck and a full bath. On the second floor there are three spacious bedrooms along with a second full bath. The whole house underwent full renovations between 2012-2013 including new kitchen, baths, gleaming oak flooring, foam insulation, new HVAC, new e

$499,000

3 beds2 baths1,188 sq ft

135 Middlesex Ave, Chester, CT 06412

Open floor plan • Waterfront home • Abundant windows

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ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Nestled on more than 1.4 private acres, this sprawling ranch offers 3 bedrooms, 2 full bathrooms, an oversized two-car garage, two storage sheds, and so much more. The spacious eat-in kitchen features a propane gas stove, stainless steel appliances, and ample space for everyday living and entertaining. The light filled living room is highlighted by a stunning three unit picture window and a beautiful oversized stone fireplace, creating a warm and inviting atmosphere. The heated basement offers endless possibilities for additional living space, a recreation room, home office, or workshop. Conveniently located just minutes from Chamard Vineyards, award-winning beaches, shopping, dining, and a

$469,900

3 beds1.5 baths1,496 sq ft

234 Airline Rd, Clinton, CT 06413

Private acres • Heated basement • Propane gas stove

Property at 8 Meeting House Rd, Haddam, CT 06438, 5 beds, 2.5 baths

$1,055,000

5 beds2.5 baths3,741 sq ft

8 Meeting House Rd, Haddam, CT 06438

Property at 32 Sunset Ter, Essex, CT 06426, 3 beds, 3 baths

$599,000

3 beds3 baths1,846 sq ft

32 Sunset Ter, Essex, CT 06426

Property at 128 Little Meadow Rd, Haddam, CT 06438, 2 beds, 2 baths

$450,000

2 beds2 baths448 sq ft

128 Little Meadow Rd, Haddam, CT 06438

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

$199,900

2 beds1 bath448 sq ft

2 Hay Field Rd, East Haddam, CT 06415

Property at 82 Old Post Rd, Clinton, CT 06413, 3 beds, 2.5 baths

$629,000

3 beds2.5 baths1,765 sq ft

82 Old Post Rd, Clinton, CT 06413

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 452 Essex Rd, Westbrook, CT 06498, 3 beds, 2 baths

$574,900

3 beds2 baths2,028 sq ft

452 Essex Rd, Westbrook, CT 06498

Property at 9 Old Colony Rd, Old Saybrook, CT 06475, 4 beds, 2 baths

$675,000

4 beds2 baths1,344 sq ft

9 Old Colony Rd, Old Saybrook, CT 06475

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

$425,000

3 beds1 bath1,112 sq ft

104 Higby Rd, 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 18 Portland St, Middletown, CT 06457, 5 beds, 3 baths

$90,000

5 beds3 baths1,558 sq ft

18 Portland St, Middletown, CT 06457

Property at 163 Pearl St, Middletown, CT 06457, 6 beds, 2 baths

$410,000

6 beds2 baths2,982 sq ft

163 Pearl St, Middletown, CT 06457

Property at 79 Wesley Ave, Westbrook, CT 06498, 2 beds, 2 baths

$500,000

2 beds2 baths1,320 sq ft

79 Wesley Ave, Westbrook, CT 06498

Property at 19 Portland St, Middletown, CT 06457, 5 beds, 2 baths

$299,000

5 beds2 baths1,760 sq ft

19 Portland St, Middletown, CT 06457

Property at 52 Jobs Gate 2, Portland, CT 06480, 1 bed, 1 bath

$172,500

1 bed1 bath592 sq ft

52 Jobs Gate 2, Portland, CT 06480

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 81 Hartford Ave, Old Saybrook, CT 06475, 4 beds, 2 baths

$2,150,000

4 beds2 baths2,440 sq ft

81 Hartford Ave, Old Saybrook, CT 06475

Property at 110 Freeman Rd, Middletown, CT 06457, 4 beds, 1.5 baths

$599,900

4 beds1.5 baths2,070 sq ft

110 Freeman Rd, Middletown, CT 06457

Property at 21 E Shore Dr, Higganum, CT 06415, 2 beds, 1 bath

$559,900

2 beds1 bath1,153 sq ft

21 E Shore Dr, Higganum, CT 06415

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 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 18 Overlook Dr, East Haddam, CT 06423, 4 beds, 2 baths

$299,900

4 beds2 baths2,464 sq ft

18 Overlook Dr, East Haddam, CT 06423

Property at 7 Portland St, Middletown, CT 06457, 3 beds, 1 bath

$169,900

3 beds1 bath1,440 sq ft

7 Portland St, Middletown, CT 06457

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 52 Pond Meadow Rd, Ivoryton, CT 06442, 2 beds, 2 baths

$430,000

2 beds2 baths810 sq ft

52 Pond Meadow Rd, Ivoryton, CT 06442

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 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 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 96 Chalker Beach Rd, Old Saybrook, CT 06475, 3 beds, 1 bath

$649,900

3 beds1 bath968 sq ft

96 Chalker Beach Rd, Old Saybrook, CT 06475

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 87 Main St, Deep River, CT 06417, 8 beds, 6 baths

$1,150,000

8 beds6 baths7,300 sq ft

87 Main St, Deep River, CT 06417

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 5-7 Haddam Dock Rd, Haddam, CT 06438, 6 beds, 5.5 baths

$2,450,000

6 beds5.5 baths4,442 sq ft

5-7 Haddam Dock Rd, Haddam, CT 06438

Property at 18 Lake Blvd, East Hampton, CT 06424, 3 beds, 1 bath

$304,900

3 beds1 bath888 sq ft

18 Lake Blvd, East Hampton, CT 06424

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Vintage Homes for Sale in Middlesex County

There are currently 141 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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