Vintage homes for sale & real estate in Cheshire, CT

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COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Cheshire, CT:
Welcome to 781 Cook Hill Road, where classic charm meets modern updates on a private, nearly 2-acre level lot. This inviting Cape features a convenient breezeway and mudroom; an oversized two-car garage; a large eat-in kitchen with elegant cabinetry - complete with a built-in coffee station and wine bar; and three generously sized bedrooms, including a primary suite with a beautifully bright arched window and a half bath. Delight in cozy evenings by the wood-burning fireplace in the living room, or gather around the gas fireplace in the family/dining room, enjoying the large bay window. You'll find hardwood floors and exquisite woodwork throughout, adding warmth and character to every room.

$575,000

3 beds2.5 baths2,593 sq ft

781 Cook Hill Rd, Cheshire, CT 06410

1.9 acre lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
Vintage Home for sale in Cheshire, CT:
Beautifully Renovated Gem in Cheshire. This stunningly renovated two-bedroom, one-bath home in Cheshire showcases exceptional craftsmanship and attention to detail at every turn. Step inside to an open-concept floor plan that feels bright and inviting, featuring a modern eat-in kitchen with beautiful stainless steel appliances, custom tile work, and high-end finishes that truly elevate the space. Every inch of the home reflects thoughtful design and quality - from the stylish flooring to the trim work and lighting choices. Outside, you'll find a spacious, lightly wooded lot with a fantastic yard (over 1 acre) perfect for entertaining, relaxing, or family gatherings. The inviting covered fro

$339,900

2 beds1 bath765 sq ft

278 Wiese Rd, Cheshire, CT 06410

High-end finishes • Custom tile work • 1.1 acre lot

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Cheshire, CT:
Fabulous Colonial on a quiet street in the heart of southern Cheshire! The oversized rooms, flexible floorplan, and many updates make this the perfect home for you! A welcoming formal Living Room leads to a spacious Dining Area with terrific flow for entertaining and everyday living. The open-concept Kitchen has stainless steel appliances, a breakfast bar, and ample storage. An enormous first-floor Family Room is the heart of the home, with vaulted ceilings, raised-hearth wood-burning fireplace with bluestone mantle, and access to patio & yard. An oversized Primary Bedroom, second Bedroom, and Full Bathroom complete the first floor. Upstairs, you'll find two additional spacious Bedroo

$485,000

4 beds2 baths2,312 sq ft

1213 Avon Blvd, Cheshire, CT 06410

0.41 acre lot • 2 garage spots • Car-dependent

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Cheshire, CT:
Welcome to your new home in Cheshire! This bright and beautifully maintained 4-bedroom, 3-bath Cape Cod is nestled in a private, serene setting while still close to all that Cheshire has to offer. Step inside to find a warm and inviting floor plan filled with natural light, featuring spacious living areas, hardwood floors, and a modern, well-appointed kitchen perfect for entertaining. The primary suite offers comfort and privacy, while the additional bedrooms provide plenty of space for family, guests, or a home office. Enjoy peaceful mornings or summer gatherings on the expansive back deck overlooking the quiet, wooded yard. With its classic charm and move-in-ready condition, this home is

$459,900

4 beds3 baths1,456 sq ft

634 Cornwall Ave, Cheshire, CT 06410

0.44 acre lot • Garage • Car-dependent

ABOUT THIS HOME
Vintage Home for sale in Cheshire, CT:
In the very heart of Cheshire, this 4-bedroom, 4-bath historic beauty (built in 1840) offers over 3,200 sq ft of character, charm, and modern updates. Sitting on a rare 3/4-acre lot with city water and sewer, you'll be just steps from shops, restaurants, the linear trail, parks-literally everything! Inside, a soaring cathedral-ceiling great room sets the stage for unforgettable gatherings. A flexible layout includes a potential in-law suite with private entrance. Outside, enjoy multiple entertaining spaces, a sparkling above-ground pool, and a huge driveway with generous parking. Recent upgrades include a two-car garage, new hot water heater, freshly painted exterior, brand-new driveway, an

$589,000

4 beds4 baths3,247 sq ft

167 Spring St, Cheshire, CT 06410

Recent upgrades • Huge driveway • Generous parking

Property at 975 Waterbury Rd, Cheshire, CT 06410, 4 beds, 3 baths

$415,000

4 beds3 baths2,544 sq ft

975 Waterbury Rd, Cheshire, CT 06410

Property at 2035 Scott Rd, Cheshire, CT 06410, 3 beds, 2.5 baths

$1,195,000

3 beds2.5 baths2,118 sq ft

2035 Scott Rd, Cheshire, CT 06410

Property at 1325 Avon Blvd, Cheshire, CT 06410, 3 beds, 1 bath

$399,900

3 beds1 bath1,316 sq ft

1325 Avon Blvd, Cheshire, CT 06410

Property at 264 Timber Ln, Cheshire, CT 06410, 3 beds, 2 baths

$420,000

3 beds2 baths1,350 sq ft

264 Timber Ln, Cheshire, CT 06410

Property at 1731 Marion Rd, Cheshire, CT 06410, 5 beds, 3 baths

$850,000

5 beds3 baths4,352 sq ft

1731 Marion Rd, Cheshire, CT 06410

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NEW 4 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Cheshire, CT:
Welcome to 55 Forest Lane, where modern comfort meets classic charm! This beautifully remodeled 3-bedroom, 2-full bath home is move-in ready and nestled in one of Wolcott's most desirable neighborhoods. Step inside to find a bright, open-concept living area featuring new flooring, recessed lighting, and a freshly updated kitchen with stainless steel appliances, quartz countertops, and custom cabinetry. Enjoy peace of mind with brand-new systems, updated electrical, plumbing, and energy-efficient windows throughout. The home also includes a one-car garage and a private backyard, perfect for relaxing or entertaining outdoors. Conveniently located near schools, shopping, dining, and parks, thi

$419,900

3 beds2 baths1,514 sq ft

55 Forest Ln, Wolcott, CT 06716

0.34 acre lot • Garage • Car-dependent

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Cheshire, CT:
Charming and spacious multi-level home with over 2,700 sq. ft. on 1.69 acres. Built in 1830 with two wings added in the past 55 years, blending classic charm and modern function. Main level offers a kitchen with center island, formal dining room with hardwood floors, large family room with propane stove and sliders out to patio, living room with wood burning stove and also has sliders to patio, plus one bedroom and an updated full bath. The split level features three bedrooms with a walk-in closet and plenty of storage. Upper level includes two additional bedrooms, a remodeled full bath, and a walk-in attic for extra storage. Oversized garage, fenced yard with stone walls, garden areas and

$449,900

6 beds2 baths2,740 sq ft

20 Hydelor Ave, Prospect, CT 06712

1.69 acre lot • Garage • Car-dependent

NEW 21 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Cheshire, CT:
Colonia with addition in the back, plus finished basement for extra living space; 2nd floor additional room could be used as 4th bedroom; Formal dining room, living room and an office on first floor. Newly renovated kitchen and bathrooms. This house will be ideal for a large family. Level and fenced-in back yard for entertainment. Two good sized storage rooms in the back yard for your tools and bikes. Roof and Septic system are about 5 years old. Public sewer in street. Priced to sell. Highest & best offer by November 5, at 7pm.

$375,000

3 beds3 baths2,301 sq ft

91 Marshall St, Wallingford, CT 06492

8,712 sq ft lot • Garage • Very walkable

ABOUT THIS HOME
Vintage Home for sale in Cheshire, CT:
This beautiful home has been renovated from top to bottom. Featuring a brand new roof, siding, walls, and gas boiler for the new owner's peace of mind. The main level offers gleaming hardwood floors and a spacious family room with its own cozy fireplace, perfect for relaxing or entertaining. Upstairs, you'll find three bright and comfortable bedrooms. With all major updates already completed, this move-in ready home combines modern comfort with lasting quality.

$349,900

3 beds1.5 baths1,992 sq ft

66 Evansville Ave, Meriden, CT 06451

0.25 acre lot • Car-dependent

ABOUT THIS HOME
Vintage Home for sale in Cheshire, CT:
This charming 3-bedroom, 1-bath home sits on a spacious and picturesque 0.6-acre lot in one of Southington's most desirable and friendly neighborhoods. Just down the street from Recreation Park and a minute from Southington Country Club, it offers a great mix of convenience and quiet living. Inside, you'll find hardwood floors throughout, central air, and bright open living spaces filled with natural light. A wall of glass doors in the living room opens to a deck overlooking the tree-filled backyard, creating an easy connection between indoor and outdoor living. The unfinished walk-out basement with large windows offers plenty of potential for additional living space, whether as a family ro

$350,000

3 beds1 bath1,003 sq ft

7 Zwicks Farm Rd, Plantsville, CT 06479

0.65 acre lot • Car-dependent

ABOUT THIS HOME
Vintage Home for sale in Cheshire, CT:
Welcome Home to 23 Nancy Mae Ave! Step into this beautifully maintained and spacious 3-bedroom ranch, perfectly situated on a generous 1.06-acre lot. This stunning home offers modern updates and comfortable living, ready for you to move right in and make it your own. Enjoy the open-concept eat-in kitchen with a walkout to a large, open backyard-ideal for entertaining or simply relaxing in nature. The lower level boasts a beautifully finished rec/family room, perfect for gatherings or quiet evenings. A unique feature is the integrated stairwell added by the current owners, providing cozy access to the lower level and oversized 2-car garage. Recent updates include, new roof, new well pump, ne

$430,000

3 beds1.5 baths1,376 sq ft

23 Nancy Mae Ave, Prospect, CT 06712

1.06 acre lot • 2 garage spots • Pool

Property at 9 Whitlock Ave, Plantsville, CT 06479, 2 beds, 1.5 baths

$315,000

2 beds1.5 baths1,408 sq ft

9 Whitlock Ave, Plantsville, CT 06479

Property at 44 Douglas Dr, Meriden, CT 06451, 4 beds, 1 bath

$195,000

4 beds1 bath1,080 sq ft

44 Douglas Dr, Meriden, CT 06451

Property at 39A Waterbury Rd, Prospect, CT 06712, 3 beds, 1 bath

$499,900

3 beds1 bath1,260 sq ft

39A Waterbury Rd, Prospect, CT 06712

Property at 58 Spruce St, Meriden, CT 06451, 3 beds, 2.5 baths

$429,999

3 beds2.5 baths2,401 sq ft

58 Spruce St, Meriden, CT 06451

Property at 15 Marshall St, Wallingford, CT 06492, 3 beds, 2 baths

$349,900

3 beds2 baths1,106 sq ft

15 Marshall St, Wallingford, CT 06492

Property at 78 Cutlery Ave, Meriden, CT 06451, 4 beds, 2 baths

$419,000

4 beds2 baths1,718 sq ft

78 Cutlery Ave, Meriden, CT 06451

Property at 54 Brentwood Ave, Waterbury, CT 06705, 2 beds, 1 bath

$239,000

2 beds1 bath932 sq ft

54 Brentwood Ave, Waterbury, CT 06705

Property at 109 Clifton St, Wallingford, CT 06492, 3 beds, 2 baths

$359,900

3 beds2 baths1,368 sq ft

109 Clifton St, Wallingford, CT 06492

Property at 26 West St, Wallingford, CT 06492, 2 beds, 1 bath

$242,250

2 beds1 bath980 sq ft

26 West St, Wallingford, CT 06492

Property at 25 Forest Rd, Wallingford, CT 06492, 2 beds, 2 baths

$449,000

2 beds2 baths1,888 sq ft

25 Forest Rd, Wallingford, CT 06492

Property at 461 Meriden Waterbury Tpke, Southington, CT 06489, 3 beds, 2.5 baths

$399,000

3 beds2.5 baths2,624 sq ft

461 Meriden Waterbury Tpke, Southington, CT 06489

Property at 1190 Meriden Rd, Waterbury, CT 06705, 3 beds, 2 baths

$298,000

3 beds2 baths1,888 sq ft

1190 Meriden Rd, Waterbury, CT 06705

Property at 298 Wooding Hill Rd, Bethany, CT 06524, 1 bed, 1 bath

$199,900

1 bed1 bath783 sq ft

298 Wooding Hill Rd, Bethany, CT 06524

Property at 230 Benham Ave, Wallingford, CT 06492

$475,000

— beds— baths— sq ft

230 Benham Ave, Wallingford, CT 06492

Vintage Homes for Sale in Cheshire

There are currently 10 vintage homes for sale in Cheshire at a median listing price of $572K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Cheshire stay on the market for 53 days and receive 2 offers. This map is refreshed with the newest listings in Cheshire every 15 minutes.

In the past month, 25 homes have been sold in Cheshire. In addition to houses in Cheshire, there were also 29 condos, 1 townhouse, and 1 multi-family unit for sale in Cheshire last month. Find your dream home in Cheshire 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 Cheshire are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Cheshire. If you're looking to sell your home in the Cheshire area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Cheshire with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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