Vintage homes for sale & real estate in Windsor, CT

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ABOUT THIS HOME
Vintage Home for sale in Windsor, CT:
Welcome to this charming Colonial style home with 3 beds 2.1 bath in historical Windsor. Complete with Hardwood floors throughout. Open concept floor plan, from the oversized Dining room to the fireplaced Living room. A Sitting room/Sunroom/Office with french doors to the living room. Freshly painted. Granite countertop with tile backdrop. While on the 2nd floor you will notice a private outside sitting area near the master bedroom. This home has a 2 car garage just waiting to protect your vehicles from the northeast elements. A level landscaped yard is great for family activities. Nice area for walking, as both sides have sidewalks. Great location-close to shopping, churches, great schools

$340,000

3 beds1.5 baths1,788 sq ft

24 Giddings Ave, Windsor, CT 06095

Colonial style home • Sunroom • Sitting room

OPEN TODAY, 1PM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Windsor, CT:
This classic 3-bedroom, 2-bath Cape offers a versatile floor plan, plenty of potential, and several major improvements already completed! The main level features a combined kitchen and dining area with white cabinetry and hardwood flooring in the dining area. The living room offers hardwood floors and a fireplace, while a convenient first-floor bedroom provides access to the enclosed porch. A full bathroom completes the main level. Upstairs, you'll find a spacious primary bedroom, guest bedroom and second full bathroom. The partially finished basement offers a family room, separate office, laundry area and additional storage. Outside, enjoy a private backyard with mature trees, rear deck, e

$323,500

3 beds2 baths1,613 sq ft

26 Scarborough Rd, Windsor, CT 06095

Hardwood flooring • Separate office • First-floor bedroom

OPEN TODAY, 11AM TO 1PM

ABOUT THIS HOME
Vintage Home for sale in Windsor, CT:
This charming 3-bedroom, 1-bath Old Style home offers classic character, some interior upgrades, and so much potential! The fenced-in yard provides a great space for outdoor entertaining, gardening, or simply relaxing. A detached two-car garage adds convenience and extra storage. With a blend of traditional charm and thoughtful improvements, this home offers endless possibilities to add your personal touches and make it truly your own. Whether you're looking for your first home or your next project, this property is full of opportunity. Bring your vision and imagine the possibilities! All outbuildings EXCEPT for the Log Cabin will be removed prior to closing.

$320,000

3 beds1 bath1,504 sq ft

794 Matianuck Ave, Windsor, CT 06095

Interior upgrades • Outdoor entertaining • Fenced-in yard

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Windsor, CT:
SPACIOUS COLONIAL WITH EXCEPTIONAL FLEXIBILITY & IN-LAW POTENTIAL! Set on a generously sized lot in convenient location, this expansive 2,812sf home offers a rare combination of size, versatility, & opportunity. Originally designed as a ranch & thoughtfully expanded w/ substantial addition (1990's), the home features 5 bedrooms, 4.5 bathrooms, providing an abundance of living space easily accommodating multigenerational living, extended family, guests, home office needs, or potential in-law arrangement. Welcoming front entry opens to living room highlighted by hardwood floors & classic wood burning fireplace. Spacious kitchen w/ large center island, ample cabinet &am

$385,000

5 beds4.5 baths2,812 sq ft

521 W Wolcott Ave, Windsor, CT 06095

Brand new roof • In law potential • New solar system

ABOUT THIS HOME
Vintage Home for sale in Windsor, CT:
CLASSIC COLONIAL LIVING W/ THOUGHTFUL UPDATES & EXCEPTIONAL SETTING! Set against the open fields of Clover Street School & positioned on a level . 26 acre lot, this 3 bedroom home offers approximately 2,130sf of comfortable living space. Inside, the home unfolds w/ gracious living spaces that make a traditional colonial so enduring. The front-to-back living room features hardwood flooring & an abundance of natural light, while the dining room is distinguished by crown & wall molding. The kitchen has been refreshed w/ new stainless steel range & refrigerator, & a charming sunroom provides a delightful transition to the outdoors, opening to the rear patio &

$329,900

3 beds1.5 baths2,130 sq ft

37 Clover St, Windsor, CT 06095

Built-in cabinetry • Recreation room • Dry bar

Property at 1476 Poquonock Ave, Windsor, CT 06095, 4 beds, 2 baths

$349,900

4 beds2 baths1,804 sq ft

1476 Poquonock Ave, Windsor, CT 06095

Property at 28 Nod Rd, Windsor, CT 06095, 3 beds, 1.5 baths

$279,000

3 beds1.5 baths1,176 sq ft

28 Nod Rd, Windsor, CT 06095

Property at 110 Matianuck Ave, Windsor, CT 06095, 3 beds, 2 baths

$275,000

3 beds2 baths1,229 sq ft

110 Matianuck Ave, Windsor, CT 06095

Property at 930 Delilah Dr, Windsor, CT 06095, 3 beds, 1.5 baths

$279,900

3 beds1.5 baths1,440 sq ft

930 Delilah Dr, Windsor, CT 06095

Property at 1128 Poqunock Ave, Windsor, CT 06095, 3 beds, 1.5 baths

$359,900

3 beds1.5 baths2,064 sq ft

1128 Poqunock Ave, Windsor, CT 06095

Property at 140 Matianuck Ave, Windsor, CT 06095, 3 beds, 2 baths

$325,000

3 beds2 baths1,114 sq ft

140 Matianuck Ave, Windsor, CT 06095

Property at 36 Woodybrook Rd, Windsor, CT 06095, 3 beds, 2 baths

$274,995

3 beds2 baths1,229 sq ft

36 Woodybrook Rd, Windsor, CT 06095

Property at 342 Mountain Rd, Windsor, CT 06095, 2 beds, 1 bath

$270,000

2 beds1 bath1,343 sq ft

342 Mountain Rd, Windsor, CT 06095

Property at 1178 Poquonock Ave, Windsor, CT 06095, 4 beds, 3 baths

$389,000

4 beds3 baths2,167 sq ft

1178 Poquonock Ave, Windsor, CT 06095

Property at 193 Rood Ave, Windsor, CT 06095, 3 beds, 1.5 baths

$365,000

3 beds1.5 baths1,204 sq ft

193 Rood Ave, Windsor, CT 06095

Property at 284 Deerfield Rd, Windsor, CT 06095, 3 beds, 2 baths

$325,000

3 beds2 baths1,511 sq ft

284 Deerfield Rd, Windsor, CT 06095

Property at 19 Portman St, Windsor, CT 06095, 2 beds, 1 bath

$299,900

2 beds1 bath1,133 sq ft

19 Portman St, Windsor, CT 06095

Property at 37 Irving St, Windsor, CT 06095, 3 beds, 2 baths

$399,900

3 beds2 baths1,383 sq ft

37 Irving St, Windsor, CT 06095

Property at 15 Barber St, Windsor, CT 06095, 3 beds, 1.5 baths

$409,900

3 beds1.5 baths1,722 sq ft

15 Barber St, Windsor, CT 06095

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OPEN TODAY, 12:30PM TO 2PMFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Windsor, CT:
Welcome to 67 Longlane Road! This charming 3-bedroom Colonial offers a wonderful combination of classic character, thoughtful updates, and comfortable living in a convenient West Hartford location. The inviting living room features hardwood floors, crown molding, a cozy pellet stove, and plenty of natural light, creating a warm and welcoming space to relax or entertain. The beautifully updated kitchen features new white cabinetry, quartz countertops, elegant white subway tile backsplash, stainless steel appliances, a sleek stainless steel vent hood, and luxury vinyl plank flooring. Just off the kitchen, a spacious mudroom and laundry area offers additional built-in storage and convenient ac

$499,900

3 beds1.5 baths1,560 sq ft

67 Longlane Rd, West Hartford, CT 06117

Pellet stove • Updated kitchen • Granite countertops

COMING SOONFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Windsor, CT:
INVESTOR & CONTRACTOR SPECIAL - REHAB OPPORTUNITY Bring your vision and tools to this value-add opportunity in Bloomfield! 6 Livingstone Rd offers investors, contractors, and experienced buyers the chance to acquire a property with renovation and potential equity-building possibilities. The property is being offered as an "as-is" sale and is ideal for a buyer looking for a project to renovate, improve, and potentially resell, rent, or hold as a long-term investment. Highlights: Investor and contractor special Excellent renovation opportunity Potential to add value through improvements Opportunity for a fix-and-flip or rental investment Bring your contractor, plans, and idea

$299,000

4 beds1.5 baths1,999 sq ft

6 Livingstone Rd, Bloomfield, CT 06002

0.38 acre lot • 2 garage spots • Built 1952

NEW 15 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Windsor, CT:
Inviting and full of possibilities, this Hartford property is a great opportunity for buyers looking to create a home that reflects their own style! Offering 2 bedrooms, 1 full bathroom, and approximately 1,080 square feet of living space, this home provides a comfortable layout with plenty of potential to personalize and make it your own. Built in 1943, the property offers classic character and exciting possibilities for homeowners or investors alike. Conveniently located in Hartford's North End, with easy access to local shopping, dining, everyday amenities, and major routes, this property is ready for its next chapter. Come explore the possibilities and envision the potential this home h

$359,000

2 beds1 bath1,080 sq ft

66 Branford St, Hartford, CT 06112

Classic character • 6,098 sq ft lot • Built 1943

OPEN TODAY, 1PM TO 3PMFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Windsor, CT:
Welcome home to this charming and recently refreshed 3-bedroom, 1.5 bath ranch, nestled in Bloomfield! Offering the ease and comfort of one-level living, this inviting home is ready for its next owners to move right in and make it their own. Step inside and enjoy a warm, welcoming atmosphere with comfortable living spaces perfect for everyday living. The partially finished lower level offers additional versatile space, ideal for a cozy family room, home office, recreational area, or simply a place to unwind. Outside, enjoy a spacious, fenced-in backyard offering room for summer gatherings, gardening, pets, or peaceful afternoons outdoors. A detached one-car garage adds convenience and extra

$299,000

3 beds1.5 baths984 sq ft

52 Ellsworth Dr, Bloomfield, CT 06002

Fenced in backyard • New water heater • One level living

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Windsor, CT:
Welcome to 40 Wynding Hills Rd, a charming Cape Cod-style home nestled in the highly desirable Wynding Hills neighborhood of East Granby, CT. This inviting 4-bedroom, 2.5-bath residence offers the perfect blend of classic character and modern comfort. Step inside to discover an updated kitchen, a cozy wood-burning fireplace in the living room, updated bathrooms throughout featuring a luxurious large soaking tub in the upstairs primary suite, and a partially finished basement ready for additional living space or storage. Recent mechanical updates include a brand-new furnace and hot water heater, providing peace of mind for years to come. A renovated mudroom leads out to the private deck off

$409,900

4 beds2.5 baths1,800 sq ft

40 Wynding Hills Rd, East Granby, CT 06026

Large soaking tub • Hot water heater • Updated kitchen

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Windsor, CT:
Step back in time with this distinctive Colonial, built in 1833 and beautifully situated on 2.45 serene acres along historic Old Main Street in South Windsor. Located on the Connecticut River side of Main Street, this spacious home offers 3-5 possible bedrooms with an abundance of character throughout. Period details include four fireplaces, some beautiful wide-board flooring, high ceilings, mouldings and an impressive staircase that reflects the home's historic charm. There is plenty of space to put a Primary bedroom on the first floor. The eat-in kitchen features a convenient pantry, large double castiron sink and a wood stove. A separate entrance leads to flexible space ideal for an in-h

$465,000

3 beds1.5 baths3,316 sq ft

1225 Main St, South Windsor, CT 06074

Flexible space • Wood stove • Two barns

Property at 404 Woodland St, Windsor Locks, CT 06096, 3 beds, 2 baths

$399,900

3 beds2 baths1,400 sq ft

404 Woodland St, Windsor Locks, CT 06096

Property at 51 School St, Windsor Locks, CT 06096, 3 beds, 2 baths

$149,900

3 beds2 baths1,344 sq ft

51 School St, Windsor Locks, CT 06096

Property at 79 W Ridge Dr, West Hartford, CT 06117, 3 beds, 2.5 baths

$615,000

3 beds2.5 baths2,507 sq ft

79 W Ridge Dr, West Hartford, CT 06117

Property at 265 Green Manor Ter, Windsor Locks, CT 06096, 3 beds, 1.5 baths

$215,000

3 beds1.5 baths1,035 sq ft

265 Green Manor Ter, Windsor Locks, CT 06096

Property at 53 Laurel Rd, Windsor Locks, CT 06096, 2 beds, 1 bath

$279,000

2 beds1 bath1,075 sq ft

53 Laurel Rd, Windsor Locks, CT 06096

Property at 163 Manchester St, Hartford, CT 06112, 3 beds, 1.5 baths

$349,900

3 beds1.5 baths1,630 sq ft

163 Manchester St, Hartford, CT 06112

Property at 4 Northbrook Dr, West Hartford, CT 06117, 3 beds, 2 baths

$380,000

3 beds2 baths1,900 sq ft

4 Northbrook Dr, West Hartford, CT 06117

Property at 428 Litchfield Dr, Windsor Locks, CT 06096, 3 beds, 1 bath

$319,900

3 beds1 bath925 sq ft

428 Litchfield Dr, Windsor Locks, CT 06096

Property at 695 Tolland St, East Hartford, CT 06108, 3 beds, 1.5 baths

$295,000

3 beds1.5 baths2,050 sq ft

695 Tolland St, East Hartford, CT 06108

Property at 79 Bloomfield Ave, Hartford, CT 06107, 3 beds, 2.5 baths

$675,000

3 beds2.5 baths2,360 sq ft

79 Bloomfield Ave, Hartford, CT 06107

Property at 83 Haynes Rd, West Hartford, CT 06117, 4 beds, 2.5 baths

$515,000

4 beds2.5 baths2,420 sq ft

83 Haynes Rd, West Hartford, CT 06117

Property at 22 Branford St, Hartford, CT 06112, 4 beds, 2 baths

$269,000

4 beds2 baths1,008 sq ft

22 Branford St, Hartford, CT 06112

Property at 80 Strong Rd, South Windsor, CT 06074, 4 beds, 2 baths

$399,900

4 beds2 baths1,804 sq ft

80 Strong Rd, South Windsor, CT 06074

Property at 28 School St, Windsor Locks, CT 06096, 2 beds, 1.5 baths

$350,000

2 beds1.5 baths1,176 sq ft

28 School St, Windsor Locks, CT 06096

Vintage Homes for Sale in Windsor

There are currently 19 vintage homes for sale in Windsor at a median listing price of $360K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windsor stay on the market for 25 days and receive 1 offers. This map is refreshed with the newest listings in Windsor every 15 minutes.

In the past month, 27 homes have been sold in Windsor. In addition to houses in Windsor, there were also 15 condos, 0 townhouses, and 2 multi-family units for sale in Windsor last month. Find your dream home in Windsor 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 Windsor are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windsor. If you're looking to sell your home in the Windsor area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windsor with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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