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

139 homes

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COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
A private New England retreat where character, craftsmanship and nature come together. 2-3 bedroom, 1861 sq. ft. country cape set on 3.75 beautifully landscaped acres in Deep River's Winthrop area, 41 Glen Grove is a truly special property surrounded by stone walls, mature plantings and its own private pond. Inside, wide-board floors, exposed beams, built-ins, a slate entry and two fireplaces-one wood-burning and one gas-give the home warmth and authenticity, while the granite and stainless chef's kitchen brings modern function to its historic-inspired character. Currently two bedrooms, the floor plan offers excellent flexibility with a main-level den and a charming parlor/study adjoining t

$579,900

2 beds1.5 baths1,861 sq ft

41 Glen Grove Rd, Deep River, CT 06417

Private pond • Mature plantings • Stone walls

NEW 7 HRS AGO

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 den could easily serve as a first-floor bedroom (or another office), with the convenience of a full bathroom nearb

$799,900

4 beds3 baths2,496 sq ft

3 Anchorage Ln, Old Saybrook, CT 06475

Versatile den • Remodeled kitchen • Deeded access

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
INCREDIBLE!!! Gorgeous 3 bedroom, 2.5 bath colonial in Cromwell that has it all! Originally built in 1948, taken down and rebuilt in 2017! Everything was rebuilt and redone! Gorgeous chef's kitchen with granite, subway tile, high end appliances. .. island and double sink. First floor laundry room. Wide open floor plan with double sized living room with vaulted ceiling and fireplace. So many windows! Hardwood floors throughout. .. Spectacular primary suite with vaulted tray ceiling and primary bath with extra large step in shower. .. All mechanicals were replaced in 2017.. Gas heat and central air. Public utilities. Recently installed paver patio. Fully fenced yard. Gorgeous plantings and a

$499,900

3 beds2.5 baths1,680 sq ft

56 Timber Hill Rd, Cromwell, CT 06416

Vaulted ceiling • Primary suite • Chef's kitchen

NEW 19 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Welcome to 882 Killingworth Road, a beautifully updated 4-bedroom, 3-bath Colonial set on two private acres in the heart of Haddam. Offering over 2,200 sq ft of living space, this home blends classic New England charm with modern updates, including refinished hardwood floors and a bright, open layout ideal for everyday living and entertaining. The well appointed kitchen flows seamlessly into the dining and living areas, with sliding glass doors leading to a newly installed stone patio overlooking the in-ground pool and expansive yard. A standout main level primary suite features a walk in shower, tile flooring, in-suite laundry, and a spacious walk in closet. Upstairs, three additional bedr

$620,000

4 beds3 baths2,286 sq ft

882 Killingworth Rd, Higganum, CT 06441

In-ground pool • Open layout • Updated colonial

NEW 20 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Middlesex County, CT:
Welcome to this well-cared-for Cape-style home in a convenient Portland location! This inviting 3-bedroom, 1.5-bath home offers charm, comfort, and many updates. The main level features a spacious living room with fireplace, a first-floor bedroom currently being used as an office, a beautifully remodeled eat-in kitchen with plenty of cabinetry, and a formal dining room perfect for family meals or entertaining. Upstairs are two additional bedrooms. The finished lower level provides additional living space for a family room, recreation area, or hobbies. Outside, enjoy a nice lot with a private pool, offering a wonderful space to relax and entertain. Meticulously maintained and exceptionally c

$365,000

3 beds1.5 baths1,572 sq ft

43 High St, Portland, CT 06480

Newer oil tank • Private pool • Newer furnace

Property at 5 Tudor Ct E, Old Saybrook, CT 06475, 3 beds, 1 bath

$795,000

3 beds1 bath2,002 sq ft

5 Tudor Ct E, Old Saybrook, CT 06475

Property at 30 Neptune Dr, Old Saybrook, CT 06475, 4 beds, 1.5 baths

$899,000

4 beds1.5 baths1,706 sq ft

30 Neptune Dr, Old Saybrook, CT 06475

Property at 138 N Cove Rd, Old Saybrook, CT 06475, 4 beds, 3.5 baths

$2,200,000

4 beds3.5 baths2,734 sq ft

138 N Cove Rd, Old Saybrook, CT 06475

Property at 156 Little Stannard Beach Rd, Westbrook, CT 06498, 4 beds, 2 baths

$1,575,000

4 beds2 baths1,677 sq ft

156 Little Stannard Beach Rd, Westbrook, CT 06498

Property at 30 Carter Hill Rd, Clinton, CT 06413, 2 beds, 1 bath

$349,900

2 beds1 bath782 sq ft

30 Carter Hill Rd, Clinton, CT 06413

Property at 581 Main St, Cromwell, CT 06416, 3 beds, 3 baths

$425,000

3 beds3 baths2,070 sq ft

581 Main St, Cromwell, CT 06416

Property at 36 Waterside Ln, Clinton, CT 06413, 4 beds, 1.5 baths

$850,000

4 beds1.5 baths2,608 sq ft

36 Waterside Ln, Clinton, CT 06413

Property at 1 Day Point Rd #6, East Hampton, CT 06424, 1 bed, 1 bath

$219,000

1 bed1 bath430 sq ft

1 Day Point Rd #6, East Hampton, CT 06424

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 12 Ross Rd, Rockfall, CT 06481, 3 beds, 2.5 baths

$520,000

3 beds2.5 baths2,300 sq ft

12 Ross Rd, Rockfall, CT 06481

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 4 Ellis Rd, East Hampton, CT 06424, 3 beds, 1.5 baths

$275,000

3 beds1.5 baths1,370 sq ft

4 Ellis Rd, East Hampton, CT 06424

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

$599,000

5 beds2 baths2,090 sq ft

100 N Tower Hill Rd, Killingworth, CT 06419

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 120-A Shore Rd, Clinton, CT 06413, 2 beds, 1 bath

$515,000

2 beds1 bath628 sq ft

120-A Shore Rd, Clinton, CT 06413

Property at 44-46 Beach Park Rd, Clinton, CT 06413, 4 beds, 2 baths

$474,900

4 beds2 baths1,417 sq ft

44-46 Beach Park Rd, Clinton, CT 06413

Property at 16 Hawthorne Rd, East Hampton, CT 06424, 3 beds, 2 baths

$625,000

3 beds2 baths1,683 sq ft

16 Hawthorne Rd, East Hampton, CT 06424

Property at 148 Old Marlborough Tpke, Portland, CT 06480, 2 beds, 1 bath

$339,900

2 beds1 bath902 sq ft

148 Old Marlborough Tpke, Portland, CT 06480

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

$949,000

4 beds2 baths2,820 sq ft

26 Chittenden Hill Rd, Westbrook, CT 06498

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 34 Fowler Development, Middlefield, CT 06455, 2 beds, 1 bath

$647,500

2 beds1 bath1,008 sq ft

34 Fowler Development, Middlefield, CT 06455

Property at 46 Farview Ave, Old Saybrook, CT 06475, 3 beds, 2 baths

$599,000

3 beds2 baths1,552 sq ft

46 Farview Ave, Old Saybrook, CT 06475

Property at 123 Fisher Rd, Middletown, CT 06457, 3 beds, 2 baths

$369,999

3 beds2 baths1,537 sq ft

123 Fisher Rd, Middletown, CT 06457

Property at 24 Sunrise Rdg, Rockfall, CT 06481, 4 beds, 2 baths

$420,000

4 beds2 baths1,896 sq ft

24 Sunrise Rdg, Rockfall, CT 06481

Property at 436 Main St, Portland, CT 06480, 3 beds, 2 baths

$275,000

3 beds2 baths1,155 sq ft

436 Main St, 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 35 School House Rd, Old Saybrook, CT 06475, 3 beds, 1 bath

$499,999

3 beds1 bath2,718 sq ft

35 School House Rd, Old Saybrook, CT 06475

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

$1,650,000

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

$429,900

2 beds1 bath944 sq ft

50 Pond Meadow Rd, Ivoryton, CT 06442

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 46 Meech Rd, Middletown, CT 06457, 3 beds, 2 baths

$255,000

3 beds2 baths1,267 sq ft

46 Meech Rd, Middletown, CT 06457

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

$639,000

3 beds2 baths2,508 sq ft

11 Autumn Ln, Clinton, CT 06413

Property at 17 Miller St, Middletown, CT 06457, 3 beds, 1 bath

$110,000

3 beds1 bath1,302 sq ft

17 Miller St, Middletown, CT 06457

Property at 38 Little City Rd, Killingworth, CT 06419, 3 beds, 1 bath

$359,000

3 beds1 bath1,082 sq ft

38 Little City Rd, Killingworth, CT 06419

Property at 147 Old Mill Rd, Middletown, CT 06457, 3 beds, 1.5 baths

$454,900

3 beds1.5 baths1,774 sq ft

147 Old Mill Rd, Middletown, CT 06457

Property at 20 Hicksville Rd, Cromwell, CT 06416, 3 beds, 1.5 baths

$365,000

3 beds1.5 baths1,170 sq ft

20 Hicksville Rd, Cromwell, CT 06416

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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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