Winona Real Estate

Winona Real Estate

Welcome to Winona, a hidden gem nestled within the vibrant city of Hamilton, Ontario. This charming neighborhood offers a perfect blend of suburban tranquility and urban accessibility, making it an ideal place for families, young professionals, and retirees alike.

Winona is renowned for its picturesque landscapes, characterized by lush greenery and scenic parks. Residents enjoy the beauty of nature at nearby sites such as the stunning Fifty Point Conservation Area, where outdoor enthusiasts can indulge in hiking, picnicking, and birdwatching. The neighborhood's proximity to Lake Ontario also provides ample opportunities for waterfront activities, including boating and fishing, ensuring that you can soak in the beauty of the great outdoors.

Community spirit thrives in Winona, with friendly neighbors and a welcoming atmosphere that makes everyone feel at home. The area boasts a variety of local shops, cozy cafes, and restaurants, allowing residents to support small businesses while enjoying delicious meals and unique finds. Families will appreciate the quality education options available, with several reputable schools in the vicinity.

Conveniently located near major highways and public transit, Winona offers easy access to downtown Hamilton and the surrounding areas. Whether you're commuting for work or exploring the diverse attractions of the region, you'll find that everything you need is just a short drive away.

In Winona, you’ll discover a delightful mix of community, convenience, and natural beauty. Come and experience the charm of this lovely neighborhood—your dream home awaits!

Newest Listings in Winona

119 Pinot Crescent Unit 58, Hamilton
$479,050
2 Beds ⋅ 3 Baths ⋅ X14155046 MLS
The final release at Foothills of Winona, your last chance to own in this established Winonacommunity! This three-storey, back-to-back urban town delivers comfort and functionality.Soaring 9' ceilings on the main and second floors create a bright, well-planned layout foreveryday living and entertaining, while the third floor offers two bedrooms, including Primarywith 3 piece ensuite, along with a full bath. Life in Winona means close proximity to schools,parks, shopping, the Bruce Trail, Fifty Point Conservation Area's beach and the world-classwineries of the Niagara Bench, with downtown Hamilton about 20 minutes away. This is the finalchapter of the Foothills. Secure your place before these last homes are gone. Some photos arevirtually staged and from builders inventory.

119 Pinot Crescent Unit 58, Hamilton
41 Edenrock Drive, Hamilton
$619,900
2 Beds ⋅ 2 Baths ⋅ X14129508 MLS
Excellent "freehold" Unit Located in the desirable neighborhood of Winona. Unit features lower level has access to single car garage w/storage, 3 piece bath, Recrm/den/Bedrm & a/walk out to fully fenced backyard. 2nd level w/ceramic and hdwd flrs, spacious & bright kitchen w/stainless steel appliances, granite/pantry & living rm and 3rd floor has 2 large bedrooms, linen, laundry and bath. Minutes to the power Winona Crossing Shopping Centre with Costco, parks, schools & easy QEW access, GO Bus and GO Train accessibility. Great opportunity to be a part of this friendly community.

41 Edenrock Drive, Hamilton
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
$589,900
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
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
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
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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