Winona Real Estate

Winona Real Estate

Welcome to Winona, a hidden gem nestled within the vibrant city of Hamilton, Ontario. This charming neighborhood seamlessly blends suburban tranquility with easy access to urban amenities, making it an ideal spot for families, retirees, and young professionals alike.

Winona is renowned for its picturesque streets lined with beautiful homes, many of which boast stunning gardens and mature trees. The community exudes a warm and inviting atmosphere, where neighbors greet one another and children can safely play outside. The area is also home to several parks, including the popular Winona Park, which offers ample green space, walking trails, and playgrounds for family outings.

For those who appreciate a touch of nature, Winona is conveniently located near the stunning Niagara Escarpment, providing opportunities for hiking, biking, and exploring the great outdoors. Additionally, the nearby Lake Ontario waterfront offers scenic views and recreational activities, perfect for a relaxing weekend getaway.

Shopping and dining options abound in Winona, with a variety of local boutiques, cafes, and restaurants just a stone's throw away. Residents can enjoy the convenience of nearby grocery stores and essential services, ensuring that everything you need is within reach.

Education is a priority in Winona, with several reputable schools serving the area, making it an attractive choice for families looking to settle down. The neighborhood's close-knit community and excellent amenities create a perfect blend of comfort and convenience, making Winona a wonderful place to call home in Hamilton, Ontario. Come explore the charm of Winona, where community spirit meets the beauty of nature!

Newest Listings in Winona

119 Pinot Crescent Unit 16, Hamilton
$449,900
2 Beds ⋅ 1 Baths ⋅ X14114550 MLS
The final release at Foothills of Winona by DiCenzo Homes, your last chance to own in this established Winona community! These three-storey, back-to-back urban townes deliver comfort and functionality. Soaring 9' ceilings onthe main and second floors create a bright, well-planned layout for everyday living and entertaining, while the third floor offers two bedrooms, each with its own walk-in closet, along with a full bath and convenient upper level laundry.Through DiCenzo's Pick Your Plan program, buyers can further tailor their home with a variety of optional floor plan upgrades that are available. Life in Winona means close proximity to schools, parks, shopping, the Bruce Trail, Fifty Point Conservation Area's beach and the world-class wineries of the Niagara Bench, with downtown Hamiltonabout 20 minutes away. This is the final chapter of the Foothills. Secure your place before these last homes are gone. Some photos are virtually staged and from builders inventory

119 Pinot Crescent Unit 16, Hamilton
119 Pinot Crescent Unit 35, Hamilton
$599,900
3 Beds ⋅ 3 Baths ⋅ X14114422 MLS
The final release at Foothills of Winona by DiCenzo Homes, your last chance to own in this established Winona community! These all brick, two-storey, 3 bedroom homes deliver a thoughtful blend of comfort, space and function. The main floor offers a bright, well-planned layout for everyday living and entertaining, while upstairs the primary retreat features a walk-in closet and private ensuite. Through DiCenzo's Pick Your Plan program, buyers can further tailor their home with a variety of optional floor plan upgrades that are available. Life in Winona means close proximity to schools, parks, shopping, the Bruce Trail, Fifty Point Conservation Area's beach and the world-class wineries of the Niagara Bench, with downtown Hamilton about 20 minutes away. This is the final chapter of the Foothills. Secure your place before these last homes are gone. Some photos are virtually staged and from builders inventory.

119 Pinot Crescent Unit 35, Hamilton
1181 Highway No. 8 N/A, Hamilton
$624,900
4 Beds ⋅ 2 Baths ⋅ X14111340 MLS
Welcome to this 3+1 bedroom bungalow set on an impressive 75 x 194 ft lot in an excellent location! Offering plenty of space, parking and versatility, this property features a detached 21 x 23 ft garage/workshop with its own electrical panel, a large 12 x 8 ft storage shed, and an additional three-season building. The basement offers a large recreation room along with a rough-in for a kitchen and bathroom, providing excellent potential for additional living space or in-law suite. The expansive driveway provides ample parking for multiple vehicles. Recent updates include a new furnace and owned hot water tank in 2025, along with a new stove, fridge and main bathroom in 2026. Connected to city water and conveniently located close to Costco, shopping, schools and easy QEW access, this property offers a fantastic combination of space, functionality and convenience. An excellent opportunity for families, hobbyists or anyone looking for additional storage and workshop space in a desirable location!

1181 Highway No. 8 N/A, Hamilton
222 Bel Air Avenue, Hamilton
$630,000
3 Beds ⋅ 2 Baths ⋅ X13867582 MLS
Solid brick bungalow on a spacious 60' x 142' lot in Stoney Creek's established Winona neighborhood. This 3-bedroom, 1-bathroom home offers well-laid-out main floor living, anchored by a brand new kitchen and appliances - white cabinetry, stainless steel finishes, and wood-look flooring that flows into bright living and dining spaces. The main level also features built-in cabinetry, a renovated 3-piece bath, and in-law suite potential. Downstairs, the full basement is partially finished with a generous recreation room plus a separate laundry and utility area - ready for your vision. Outside, a private driveway parks 3 vehicles, and the fully fenced, mature-treed backyard includes a concrete patio pad and two storage sheds for extra space. Forced-air heat and central air keep it comfortable year-round. Set in a quiet, established pocket close to schools, parks, shopping, and highway access, this is a solid opportunity for first-time buyers, downsizers, or investors. Don't miss it!

222 Bel Air Avenue, Hamilton
40 Zinfandel Drive Unit 35, Hamilton
$550,000
2 Beds ⋅ 2 Baths ⋅ X14034392 MLS
Welcome to this beautiful, nearly new 2023-built executive common-element townhouse in desirable Stoney Creek, District 51. Thoughtfully designed across three levels, this stylish 2-bedroom, 2-bathroom home combines contemporary finishes, functional living space and an exceptional location near the Niagara Escarpment and Lake Ontario. Enter at ground level into the foyer featuring a convenient 2-piece bath, inside entry from the garage and access to the utility room. Follow the staircase to the bright, open-concept main level where the living room, dining area and kitchen flow seamlessly together-ideal for both everyday living and entertaining. The kitchen is anchored by an approximately 10-ft island, complemented by stainless steel appliances, an over-the-range microwave, pendant lighting and a generous 7'8" x 4'7" walk-in pantry. The living area features an electric fireplace and a cozy alcove perfectly suited for a love seat or reading area. Step outside to the covered balcony with glass railings and enjoy southwest views toward the Escarpment-a wonderful extension of the living space. Upstairs, you'll find two well-proportioned bedrooms with exceptional storage. The primary bedroom features an approximately 5'x6' walk-in closet, while the second bedroom offers an approximate 6'8"x7'10" walk-in closet. A 4-piece bathroom and convenient upper-level laundry complete this floor. Finished in an attractive stone and brick exterior, this executive townhome offer slow-maintenance living in one of Stoney Creek's growing communities. Ideally positioned between Fifty Road/QEW and Winona Road, with convenient access to Fifty Point Conservation Area &Marina, Winona Park, shopping, restaurants, highway access and the popular Winona Peach Festival. Modern. Spacious. Low maintenance. A wonderful place to call home

40 Zinfandel Drive Unit 35, Hamilton
27 Pettit Street, Hamilton
$499,900
3 Beds ⋅ 3 Baths ⋅ X14032888 MLS
Welcome to this spacious and inviting end-unit townhome in the heart of Winona! Offering a bright and functional layout with plenty of room for everyday living and entertaining. Main level features an open-concept kitchen, living, and dining area complete with warm wood flooring, a centre island, granite countertops, and a distinctive feature wall that adds character to the space. Large windows provide plenty of natural light. Upper level offers 3 generous bedrooms with warm wood flooring, a 3-piece primary ensuite bath, and a 4-piece main bath with updated fixtures. Partially finished lower level provides valuable additional living space and endless possibilities for a recreation room, playroom, gym, or work-from-home setup. Step outside to a private, fully fenced backyard with a deck and patio area perfect for relaxing and enjoying the warmer months. Additional highlights include an attached garage with inside entry, parking for 3 cars, and central air. Conveniently located near schools, parks, shopping, and quick QEW access, this home is perfect for families and commuters alike.

27 Pettit Street, Hamilton
1260 HIGHWAY 8 N/A, Hamilton
$1,089,900
X13883250 MLS
Rare mixed-use commercial opportunity in the heart of Winona! Situated on an impressive 79.99 ft x 201.47 ft lot with excellent Highway 8 exposure and plenty of parking for any business, this C2-zoned property offers a commercial storefront, residential living space, additional finished areas, on-site parking potential, and multiple paths for future value. The main commercial area is currently being used for business/retail purposes and offers an excellent opportunity for an owner-user, investor, or business operator looking for visibility in a growing Stoney Creek corridor. The property also includes residential living space, separate kitchen/bathroom areas, and additional finished vacant spaces, creating a compelling live/work-style opportunity for the right buyer. The current business is moving, and the property is to be sold with vacant possession, giving the next owner flexibility to operate, lease, reconfigure, or reposition the property. For buyers with a longer-term vision, the generous lot size, Highway 8 frontage, C2 zoning, and surrounding growth may also present a potential redevelopment opportunity to demolish the existing structure and explore a new purpose-built commercial, residential, or mixed-use building, subject to zoning, planning, servicing, parking, building permits, and all required approvals. A unique offering for buyers seeking exposure, flexibility, and long-term upside in the Winona/Stoney Creek market. RSA.

1260 HIGHWAY 8 N/A, Hamilton
1260 HIGHWAY 8 N/A, Hamilton
$1,089,900
4 Beds ⋅ 3 Baths ⋅ X13883234 MLS
Unique live/work-style opportunity in desirable Winona! Set on a generous 79.99 ft x 201.47 ft lot along Highway 8, this spacious mixed-use property with plenty of parking offers a rare combination of residential living space, commercial storefront potential, additional finished areas, and future upside for buyers looking for more than a traditional home. The property is currently being used as a combination residential/commercial property, with a storefront/business area, an owner-occupied residential living area, and additional vacant finished spaces with kitchen/bathroom configurations. The current business is moving, and the property is to be sold with vacant possession, giving the next owner flexibility to occupy, renovate, lease, or reimagine the property. This could be an excellent fit for a small business owner looking to live and work from the same property, a buyer needing space for extended family or private work areas, or an investor looking to add value by maximizing the property's potential through additional rental income, reconfiguration, or future unit creation, subject to buyer's review and satisfaction and all required approvals. The C2 zoning may allow for a variety of commercial uses in conjunction with residential use, making this an especially unique opportunity in the growing Winona corridor. Conveniently located with access to Highway 8, Fifty Road, Barton Street, the QEW, local shops, services, schools, and surrounding residential communities. A rare property with space, exposure, flexibility, and live/work potential. RSA

1260 HIGHWAY 8 N/A, Hamilton
1242 Highway 8 N/A, Hamilton
$799,900
X13859038 MLS
Bring your commercial vision to one of Winona's established and expanding corridors. This vacant Highway 8 parcel offers approximately 98 ft of frontage and 175 ft of depth, creating a substantial site for a future commercial or mixed-use project. The LC-3 zoning with site-specific permissions offers flexibility for a variety of business concepts, from retail and professional services to restaurants, bakeries, offices, and other neighbourhood-oriented uses. An added opportunity exists for residential units above ground-floor commercial space, providing the potential to combine residential and commercial components in one development. Conveniently situated among existing homes, businesses, and ongoing development, this property offers the space, exposure, and zoning flexibility to support a range of future plans.

1242 Highway 8 N/A, Hamilton
6 Fourseasons Drive, Hamilton
$1,450,000
4 Beds ⋅ 3 Baths ⋅ X13832394 MLS
Welcome to this impressive custom-built 4-bedroom home, tucked away on a quiet, family-friendly street in the heart of Winona - a wonderful place to raise a family and enjoy a peaceful neighbourhood lifestyle. Offering an exceptional combination of space, elegance and convenience, this beautiful home is designed for comfortable everyday living and memorable family gatherings. Striking exterior pillars and impressive curb appeal welcome you home, along with a 2-car garage and parking for up to 6 vehicles. Step inside to an elegant circular staircase, beautiful custom wood-engraved doors and soaring 18-ft ceilings in the foyer and family room, creating a bright, open and dramatic first impression. Generously sized principal rooms, 9-ft ceilings and a convenient 3-piece bathroom on the main floor make the layout especially well suited for growing or multi-generational families. The spacious basement adds incredible future potential with 8-ft ceilings, a separate entrance, rough-ins for a kitchen and bathroom, space for an additional bedroom, abundant storage and 2 cold rooms - ideal for creating an in-law suite, private space for extended family or potential future income. Outside your door, enjoy the comfort of a peaceful residential street surrounded by beautiful natural scenery, while still being close to everything your family needs. Roof replaced 2018, air condition July 2026. Winona Park, schools, Costco, LCBO, restaurants, shopping and everyday essentials at Winona Crossing are all nearby. Quick access to the QEW makes commuting to Burlington, Toronto and Niagara easy. A rare opportunity to enjoy a spacious custom home in a quiet neighbourhood where your family can settle in, grow and truly feel at home.

6 Fourseasons Drive, Hamilton
55 Chianti Crescent, Hamilton
$1,530,000
4 Beds ⋅ 4 Baths ⋅ X13786778 MLS
Welcome 55 Chianti Cres, a beautifully maintained executive family home in the heart of sought after Winona. Lovingly cared for by its original owners and thoughtfully updated throughout the years, the home offers an exceptional combination of space, comfort and functionality designed for modern family living. The main level is anchored by a dramatic vaulted great room, creating a bright and inviting gathering space at the heart of the home. Generous principal rooms provide plenty of space for both everyday living and entertaining, while four bedrooms and four bathrooms offer room for the entire family. The finished lower level adds another layer of versatility, complete with a full kitchen and bath, ideal for extended family, multi-generational living or guests. Outside, the property truly comes to life. Stunning professional landscaping surrounds the home, while the backyard has been transformed into a private summer retreat complete with an inground pool, pool shed and plenty of space to relax and entertain. Set in an established, family friendly neighbourhood, the location offers the best of Winona living - steps from the Winona Peach Festival and close to schools, parks, everyday amenities, nature and convenient highway access. A special opportunity to own a home that has been genuinely loved, carefully maintained and updated over the years, with the space and flexibility to serve a family for years to come.

55 Chianti Crescent, Hamilton
Unit C - 1247 Highway 8 N/A, Hamilton
$129,000
1 Baths ⋅ X13719534 MLS
Turnkey Quick-Service Restaurant and Ice Cream shop opportunity with exceptional rent in Stoney Creek! Here is your chance to acquire Winona's Eats and Treats, a well-established, thriving culinary destination situated along high visibility Highway 8 in the rapidly expanding Winona/Stoney Creek corridor. Boasting extraordinarily low rent of $1921/Month(inclusive of HST& TMI),this turn-key operation drastically cuts operating expenses to maximize your net profitability from day one. The business has built a loyal, year-round following as a premier local ice cream store, proudly serving guest-favorite Kawartha Dairy and Chapman's ice creams alongside milkshakes, sundaes and bubble tea. Complementing the sweet shop is a robust, savory quick-service menu featuring specialty pizzas, signature wings and gourmet appetizers, ensuring strong multi-stream revenue across all day-parts and seasons. A fully equipped commercial kitchen and inviting storefront offer a seamless transition for a new operator or an easy adaption to a new concept. The location enjoys fantastic street exposure, convenient on-site customer parking, strong online reviews and built-in delivery revenue via major platforms (UberEats, Skip the Dishes, DoorDash) and direct online ordering. Additional growth potential remains for the right buyer, or conversion to a new concept.

Unit C - 1247 Highway 8 N/A, Hamilton
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