Windsor Homes under $500,000

Welcome to Windsor, Connecticut—a charming town that perfectly blends rich history with modern convenience. Nestled in Hartford County, Windsor boasts a vibrant community, picturesque landscapes, and a strong sense of pride among its residents. With its close proximity to the Connecticut River, outdoor enthusiasts will love exploring the scenic parks and trails, while history buffs can delve into the town's fascinating past, which dates back to 1633.

Windsor is not just about its beautiful surroundings; it’s also a place where families can thrive. The town is home to top-rated schools, making it an ideal location for families looking to settle down. With a range of community events and local festivals, there’s always something happening here, fostering a tight-knit atmosphere that welcomes newcomers with open arms.

For those looking to buy a home, Windsor offers an impressive selection of properties under $500,000. Whether you’re a first-time buyer or seeking to downsize, you’ll find a variety of charming single-family homes, townhouses, and condominiums that cater to diverse tastes and lifestyles. Many of these homes feature spacious yards, modern amenities, and easy access to local shops and restaurants, ensuring that you’ll have everything you need right at your fingertips.

In Windsor, you’re not just buying a home; you’re investing in a lifestyle filled with community spirit, natural beauty, and a wealth of opportunities. Come discover what makes Windsor, CT, the perfect place to call home!

Newest Windsor Homes under $500,000

$439,900

4 Beds ⋅ 3 Baths ⋅ 24214027 MLS ⋅ Walden Woods BLDG.

Welcome to Walden Woods, one of Windsor's most desirable communities! This beautiful 4-bedroom Colonial-style PUD is tucked away on a quiet cul-de-sac, offering the perfect blend of elegance, comfort, and tranquility. Step inside to a dramatic two-story foyer that sets the tone for this inviting home. The beautifully remodeled designer kitchen, updated approximately 8 years ago, features exquisite granite countertops, a center island, generous cabinet space, and an eat-in dining area that opens seamlessly to the den with a cozy gas fireplace. The open floor plan is perfect for everyday living and entertaining! Newer wood flooring adds a touch of sophistication throughout. A formal living room and dining room provide additional space for hosting gatherings and holiday celebrations, just in time for Thanksgiving! Upstairs, retreat to the spacious primary bedroom suite featuring a private bath and a versatile adjoining sitting room, ideal for a dressing room, reading retreat, or home office. Three additional bedrooms offer plenty of space and flexibility. The expansive basement provides an abundance of storage space or wonderful possibilities to finish at your leisure and create additional living space to suit your needs. Enjoy peace of mind with several significant improvements, including a roof approximately 6 years old and newer heating and central air , 7-8 years old.

412 Pond Bridge Rd Unit 412, Windsor

$439,900

4 Beds ⋅ 3 Baths ⋅ 24213810 MLS

412 Pond Bridge Rd Unit 412, Windsor

$399,900

3 Beds ⋅ 3 Baths ⋅ 24212983 MLS ⋅ Riverside Village,The Villages At Poquonock BLDG.

Beautiful, move-in-ready townhome at The Villages at Poquonock! This rarely available home offers approximately 1,800 square feet of inviting living space, an open floor plan, gleaming hardwood floors, and custom window shades throughout. The main level features a bright, spacious living room, dining area, half bath, and a primary bedroom with a bathroom featuring a walk-in shower. Access to the backyard patio makes outdoor relaxation easy. The stunning kitchen showcases a vaulted ceiling, abundant cabinetry, quartz countertops, a center island, and fingerprint-resistant stainless steel appliances. A washer and dryer are included, along with a Pure Wash Pro X2 system that enhances cold-water washing with oxygen. Upstairs, two generously sized bedrooms offer ample closet space and share a full bathroom. Additional conveniences include an attached one-car garage, central air, a high-efficiency A. O. Smith gas tankless water heater, and public water and sewer. Enjoy the amenities of this sought-after, 64-acre community, including walking trails, a private park with a pond, an in-ground pool, and a playscape. The clubhouse offers a fitness room, kitchen, dining area, and covered outdoor picnic space. Conveniently located near shopping, restaurants, schools, and Northwest Park's 473 acres of trails and outdoor recreation, this lovely home offers comfort, convenience, and a welcoming community.

707 Old Village Cir, Windsor

$279,000

3 Beds ⋅ 2 Baths ⋅ 24212833 MLS

Cozy three-bedroom ranch nestled on a quiet dead-end street in Windsor, offering added privacy and minimal through traffic. This inviting home features hardwood floors throughout, a private driveway with ample space for multiple vehicles, and a full basement with exterior access. The basement provides excellent potential for additional storage, a workshop, or future expansion. A comfortable and conveniently located home with plenty of opportunity to make it your own.

28 Nod Rd, Windsor

$429,900

4 Beds ⋅ 2 Baths ⋅ 24207370 MLS

**HIGHEST ABD BEST OFFERS DUE FRIDAY OCTOBER 16TH 5PM**Step back in time while enjoying the comforts & flexibility of today in this exceptional antique home,originally built in 1775, nestled in the historic Poquonock section of Windsor.Rich w/ vintage character & charm,this distinctive property gives the rare opportunity to own a piece of Windsor history while providing an incredibly versatile living arrangement.Currently being enjoyed as a single-family home,it is easily convertible back to its original 2 family configuration,making it ideal for multi-generational living,owner-occupied investment,or those seeking additional living space.With4 bedrooms,2 full baths,2 sets of utilities, and separate living areas, it provides tremendous flexibility for today's lifestyle.Outside,nearly 1 acre of beautifully manicured grounds creates a private,picturesque setting. A charming bridge crosses a meandering brook, adding an enchanting touch to the already spectacular landscape.2 decks provide wonderful spaces for relaxing,entertaining,& taking in the peaceful surroundings.A fabulous family room overlooks the gorgeous backyard; a perfect gathering space that brings the beauty of the property indoors. Additional features include ample parking, a 2 car garage, and gas heat.This is a truly special property where history, character, nature, and versatility come together. This Windsor treasure offers possibilities that are rarely found in todays market.

1355 Poquonock Ave, Windsor

$429,900

5 Beds ⋅ 2 Baths ⋅ 24207372 MLS

1355 Poquonock Ave, Windsor

$329,900

3 Beds ⋅ 2 Baths ⋅ 24212093 MLS

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 & a mature pear tree that produces fruit seasonally. A convenient half bath completes the main level. Upstairs, the primary bedroom offers a generous walk-in closet, accompanied by 2 additional bedrooms & a full bath. New luxury vinyl plank flooring enhances the stairs & upper level, w/original hardwood floors preserved beneath. The finished lower level adds remarkable flexibility, offering a recreation room w/dry bar, finished laundry area w/utility sink & built-in cabinetry, & extensive storage. Whether envisioned as a casual gathering space, home gym, office, or media room, it provides valuable additional living space. Outside, the paved driveway leads to a detached 1-car garage w/a generous carport overhang, providing covered parking or an inviting shaded setting for outdoor entertaining. ***CONTINUED***

37 Clover St, Windsor

$349,900

3 Beds ⋅ 2 Baths ⋅ 24212205 MLS

Welcome to 280 Deerfield Road, a beautifully updated 3-bedroom cottage offering 1,534 square feet of comfortable, move-in-ready living space. Thoughtfully renovated throughout, this inviting home blends classic character with modern finishes. Enter through the enclosed front porch and discover a bright, open main level featuring a spacious living room with a charming fireplace and an easy flow into the dining area perfect for everyday living and entertaining. The updated kitchen offers both style and functionality, while two bedrooms and a full bathroom on the first floor provide convenient single-level living. Upstairs, a generously sized third bedroom with a half bathroom creates a flexible space for a private retreat, guest room or home office. Outside, enjoy a level, fenced backyard with a large deck and storage shed. The full walk-out basement includes a laundry area and offers ample storage and additional possibilities. Conveniently located near shopping, dining and major highways, this completely updated Windsor home is ready for its new owner!

280 Deerfield Rd, Windsor

$459,000

3 Beds ⋅ 3 Baths ⋅ 24210850 MLS ⋅ Country Walk,Walden Woods BLDG.

Welcome to your new home in the Coveted Country Walk section of Walden Woods. This beautiful home features a fantastic layout, hardwood floors and a trex deck for the beautiful New England days. The first floor has everything you need - a den, formal dining and living rooms, a Primary suite, laundry room and an eat-in kitchen opening to a deck overlooking green space. The upstairs has a loft large enough to make into an office, reading area, crafting space or whatever you can dream up, adjacent to two spacious bedrooms with walk-in closets and a full bath. Electric car? There is a plug in the garage, which also has a poured epoxy floor. Need storage? In addition to TONS of closet space, there is a full unfinished basement. Seeking activities? There are walking trails, tennis courts, an in-ground pool, a clubhouse, a community garden and more - right in your backyard. This lovely home is aspirational living at its finest.

42 Marble Faun Ln Unit 42, Windsor

$275,000

3 Beds ⋅ 2 Baths ⋅ 24210521 MLS

Nestled in Windsor, this inviting 3-bedroom, 2-full-bath home offers a wonderful opportunity to create a space that is distinctly your own. The home's comfortable living spaces provide the perfect backdrop for everyday living, entertaining, or simply relaxing at the end of the day. Three bedrooms offer flexibility for family, guests, a home office, or creative space, while two full bathrooms provide added convenience. Step outside from a deck off the kitchen and a fenced in yard and envision summer gatherings, gardening, playtime, or quiet mornings enjoying your own outdoor space. With room to personalize and add your own style, this home offers an exciting opportunity for buyers looking to create a space that feels uniquely theirs. Conveniently located in Windsor with access to shopping, dining, major routes, and the many amenities the area has to offer

110 Matianuck Ave, Windsor

$52,000

1 Beds ⋅ 1 Baths ⋅ 24210573 MLS ⋅ Delamere Woods BLDG.

One bedroom now available on FIRST FLOOR at Delamere Woods - an independent retirement community (not assisted living) for active adults 62+, just past Windsor's Historic District. This unit has premium location on first floor just steps away from the main dining room. This unit with an open living/dining area with new premium laminate flooring, efficient & kitchen with new appliances and bath with walk-in shower/tub, king-size bedroom with ample closet space. The monthly HOA covers heat, electric, water, weekly housekeeping/linen service, and 24-hour security and emergency response. Full-time management and an activity coordinator handle shopping trips, doctor visits, and more. Community life and friendship is rich: fitness classes, guest speakers, card and game rooms, book clubs, woodworking, crafts, knitting, a movie room, and cozy reading nooks. The community dining room offers affordable meals with neighbors M-F. Outside: patios, walking paths, communal gardens, and a whole-facility generator for peace of mind. Lower level features heated storage, hair salon, convenience store, exercise room, and woodworking shop. Each floor has a laundry room. Residents enjoy full autonomy - work, travel and all. Ample parking plus a guest unit for out-of-town visitors. Ready for easier, low-maintenance living with an active community without the exorbitant cost of other living facilties. Come take a look!

625 Palisado Ave Unit 102, Windsor

$499,900

4 Beds ⋅ 3 Baths ⋅ 24210142 MLS

Absolutely the most VALUE yo will see under $500K. A truly exceptional property offering the space, versatility, privacy, and amenities that are becoming increasingly difficult to find. Pool 3 Car Detached Garage! Beautifully situated on a quiet cul de sac, this updated 4 bedroom, 2.5 bath home immediately stands apart with an impressive 3 car garage detached 1 car attached, an in ground swimming pool, dog pen/run. and a spacious, open lot that gives you room to live, entertain, and enjoy your property without feeling crowded by neighboring homes. Step inside and you will find a home designed for comfortable everyday living while still offering plenty of space for entertaining family and friends. The updated interior provides a welcoming atmosphere with generous living areas, four well sized bedrooms, and a layout that can easily adapt as your needs change. Outside is where this property becomes something special. Imagine summer afternoons around your own private in ground pool, weekend gatherings in the yard, and having the space to create your own outdoor retreat. Whether you envision gardens, recreation areas, additional entertaining spaces, or simply appreciate having room around you, this property delivers possibilities that many homes simply cannot offer. For the car enthusiast, hobbyist, contractor, collector, or anyone who values additional storage, the 4 car garage is an extraordinary feature. Instead of choosing between parking, storage,

23 Coach Cir, Windsor

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Windsor Homes under $500,000

Newest Windsor Homes under $500,000

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