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

137 homes

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ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Tucked away on 4.5 beautiful acres in Killingworth, 79 Chestnut Hill Road offers exceptional privacy, peaceful pond views, and a welcoming sense of home from the moment you arrive. This distinctive 3-bedroom, 3-bath antique residence is filled with warmth and character, thoughtfully updated to provide the comfort and convenience of modern living. Extensive improvements completed between 2008 and 2026 include fresh interior paint, beautifully refinished natural hardwood floors, and a new elevated bluestone patio. Additional updates include the roof, windows, exterior paint, gutters, and water heater, along with updated electrical and plumbing, three-zone heating, central air, and a whole-hou

$749,900

3 beds3 baths2,069 sq ft

79 Chestnut Hill Rd, Killingworth, CT 06419

4.5 beautiful acres • Expansive property • 4.5 acre lot

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Spacious and versatile 4-bedroom, 2-bath home offering approximately 1,842 square feet of living space with a flexible layout and plenty of possibilities. Currently used as a single-family home, the upper and lower levels provide separate living spaces, (multi generational living) offering added privacy and flexibility. The property features two oil tanks and two electrical panels and may offer potential for a two-family setup, subject to town approval and buyer due diligence. Situated on approximately one acre with a private well and septic, this home offers plenty of room and opportunity for its next owner to make it their own.

$410,000

4 beds2 baths1,842 sq ft

601 Town St, Moodus, CT 06469

Private well • Septic • Two family setup

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Born in 1835. Reimagined for life today. Expanded to over 2,950 sq. feet, the new floor plan emphasizes light, proportion, and seamless flow from one room to the next. At its center, a beautifully composed chef's kitchen pairs a waterfall island with white cabinetry and an oversized walk-in pantry, making entertaining feel wonderfully uncomplicated. The adjoining vaulted great room is the home's defining gesture: window-lined and grounded by dramatic millwork. Three en-suite bedrooms invite family and friends to settle in with privacy. The primary suite offers two walk-in closets, while a generous upstairs lounge can easily serve as a library, office, or media room. A second-floor laundry a

$908,000

3 beds3.5 baths2,950 sq ft

60 Bushy Hill Rd, Ivoryton, CT 06442

Vaulted great room • Dramatic millwork • En-suite bedrooms

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Tucked along Trolley Road in downtown Westbrook, CT, this year-round cottage offers shoreline living with walk-to-town convenience and access to the town beach. Just steps from Christie's, Julie's Cup of Joe, The Turtle Cafe, shops, restaurants, and the Westbrook train station, you can enjoy coffee, dining, and outings close to home. South of Route 1 and within walking distance of Westbrook's sandy beaches, the location puts the best of this coastal town within easy reach. The home needs love and is ready for a new owner's vision, updates, and care. Set on a generous, level lot, this property offers an opportunity to refresh the existing single-family cottage or explore new construction, su

$275,000

2 beds1 bath573 sq ft

41 Trolley Rd, Westbrook, CT 06498

Generous level lot • Great size lot • Access to town beach

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Essex Village waterfront enjoys one-level living and truly incredible sunrise colors and direct views of spectacular sunsets over water creating reflective and ever-changing scenery. This three bedroom, modern home is nestled between Middle Cove and the Connecticut River with 190ft of direct waterfront and a completely private outdoor setting you will covet. Set on 3/4 of an acre this home comes with its own bulkhead with dockage for fast boat trips from the river to Long Island Sound and beyond. The stone patio stretches the entire length of the house and will quickly become your favorite spot. The handsome, newly renovated kitchen has extensive built-in cabinets, polished quartz counterto

$2,499,000

3 beds2.5 baths2,384 sq ft

15 Novelty Ln, Essex, CT 06426

Direct views • Stone patio • Waterfront

Property at 95 Hunting Hill Ave, Middletown, CT 06457, 3 beds, 1.5 baths

$349,000

3 beds1.5 baths1,794 sq ft

95 Hunting Hill Ave, Middletown, CT 06457

Property at 37 Colchester Ave, East Hampton, CT 06424, 2 beds, 1 bath

$319,900

2 beds1 bath1,048 sq ft

37 Colchester Ave, East Hampton, CT 06424

Property at 38 S Main St, Westbrook, CT 06498, 3 beds, 2 baths

$605,000

3 beds2 baths2,514 sq ft

38 S Main St, Westbrook, CT 06498

Property at 46 Briarcliffe Rd, East Haddam, CT 06415, 2 beds, 2 baths

$329,900

2 beds2 baths872 sq ft

46 Briarcliffe Rd, East Haddam, CT 06415

Property at 1010 Boston Post Rd, Westbrook, CT 06498, 3 beds, 2 baths

$499,000

3 beds2 baths1,486 sq ft

1010 Boston Post Rd, Westbrook, CT 06498

Property at 118 Camp St, Middletown, CT 06457, 3 beds, 2.5 baths

$425,000

3 beds2.5 baths1,740 sq ft

118 Camp St, Middletown, CT 06457

Property at 9 Ingham Hill Rd, Essex, CT 06426, 3 beds, 4.5 baths

$1,150,000

3 beds4.5 baths3,308 sq ft

9 Ingham Hill Rd, Essex, CT 06426

Property at 131 Killingworth Rd, Higganum, CT 06441, 2 beds, 2 baths

$549,900

2 beds2 baths1,351 sq ft

131 Killingworth Rd, Higganum, CT 06441

Property at 142 Crystal Lake Rd, Middletown, CT 06457, 2 beds, 1 bath

$369,900

2 beds1 bath1,188 sq ft

142 Crystal Lake Rd, Middletown, CT 06457

Property at 74 Pine Rd, East Haddam, CT 06423, 3 beds, 1 bath

$299,000

3 beds1 bath840 sq ft

74 Pine Rd, East Haddam, CT 06423

Property at 137 Parmelee Hill Rd, Durham, CT 06422, 4 beds, 2 baths

$344,900

4 beds2 baths2,479 sq ft

137 Parmelee Hill Rd, Durham, CT 06422

Property at 25 River Rd, Essex, CT 06426, 4 beds, 2.5 baths

$2,250,000

4 beds2.5 baths3,232 sq ft

25 River Rd, Essex, CT 06426

Property at 74 Boston Rd, Middletown, CT 06457, 4 beds, 2 baths

$379,000

4 beds2 baths2,196 sq ft

74 Boston Rd, Middletown, CT 06457

Property at 90 Water St, Chester, CT 06412, 1 bed, 1 bath

$237,500

1 bed1 bath1,034 sq ft

90 Water St, Chester, CT 06412

Property at 100 N Tower Hill Rd, Killingworth, CT 06419, 5 beds, 2 baths

$575,000

5 beds2 baths2,090 sq ft

100 N Tower Hill Rd, Killingworth, CT 06419

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

$599,000

3 beds2.5 baths1,765 sq ft

82 Old Post Rd, Clinton, CT 06413

Property at 18 Brook Trl, East Hampton, CT 06424, 3 beds, 1.5 baths

$347,000

3 beds1.5 baths1,224 sq ft

18 Brook Trl, East Hampton, CT 06424

Property at 42 Saybrook Rd, Middletown, CT 06457, 4 beds, 2 baths

$339,900

4 beds2 baths1,704 sq ft

42 Saybrook Rd, Middletown, CT 06457

Property at 21 River Rd, Essex, CT 06426, 5 beds, 4.5 baths

$2,850,000

5 beds4.5 baths3,502 sq ft

21 River Rd, Essex, CT 06426

Property at 10 Beach Park Rd, Clinton, CT 06413, 4 beds, 2 baths

$405,000

4 beds2 baths1,284 sq ft

10 Beach Park Rd, Clinton, CT 06413

Property at 144 Shore Rd, Clinton, CT 06413, 4 beds, 2 baths

$899,000

4 beds2 baths1,722 sq ft

144 Shore Rd, Clinton, CT 06413

Property at 105 Shore Rd, Clinton, CT 06413, 4 beds, 0.5 baths

$899,000

4 beds0.5 baths925 sq ft

105 Shore Rd, Clinton, CT 06413

Property at 188 Main St, Durham, CT 06422, 5 beds, 2 baths

$665,000

5 beds2 baths2,980 sq ft

188 Main St, Durham, CT 06422

Property at 28 River Rd, Essex, CT 06426, 3 beds, 2.5 baths

$1,595,000

3 beds2.5 baths2,359 sq ft

28 River Rd, Essex, CT 06426

Property at 50 Pond Meadow Rd, Ivoryton, CT 06442, 2 beds, 1 bath

$421,900

2 beds1 bath944 sq ft

50 Pond Meadow Rd, Ivoryton, CT 06442

Property at 64 Summer St, Portland, CT 06480, 4 beds, 2 baths

$319,900

4 beds2 baths2,478 sq ft

64 Summer St, Portland, CT 06480

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

$252,500

3 beds1 bath1,217 sq ft

92 Water St, Chester, CT 06412

Property at 43 Quarry St, Old Saybrook, CT 06475, 3 beds, 1 bath

$285,000

3 beds1 bath941 sq ft

43 Quarry St, Old Saybrook, CT 06475

Property at 18-A Lake Shore Dr, Middlefield, CT 06455, 2 beds, 1 bath

$595,000

2 beds1 bath961 sq ft

18-A Lake Shore Dr, Middlefield, CT 06455

Property at 149 Spring St, Middletown, CT 06457, 4 beds, 4 baths

$524,900

4 beds4 baths3,401 sq ft

149 Spring St, Middletown, CT 06457

Property at 64 Haddam Quarter Rd, Durham, CT 06422, 4 beds, 2.5 baths

$899,900

4 beds2.5 baths3,306 sq ft

64 Haddam Quarter Rd, Durham, CT 06422

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 29 Shadow Ln, Cromwell, CT 06416, 3 beds, 1 bath

$315,000

3 beds1 bath1,230 sq ft

29 Shadow Ln, Cromwell, CT 06416

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

$415,000

4 beds2 baths1,352 sq ft

104 Bell St, Middletown, CT 06457

Property at 26 Old Wallingford Rd, Durham, CT 06422, 5 beds, 3 baths

$859,000

5 beds3 baths6,384 sq ft

26 Old Wallingford Rd, Durham, CT 06422

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

$615,000

3 beds2.5 baths2,577 sq ft

128 Killingworth Rd, Higganum, CT 06441

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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.

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