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Detached for Sale in Hamilton
Popular ListingNeighbourhood: Stipley
- MLS Number
- X13481424
- Property Type
- Detached
- Status
- active
- Days on Site
- 9
- Bedrooms
- 5
- Bathrooms
- 3
- Square Feet
- 1,500 - 1,999 sqft
- Neighbourhood
- Hamilton
- Listing Brokerage
- RE/MAX ESCARPMENT REALTY INC.
Welcome to 37 Connaught Avenue South, where timeless character meets one of Hamilton's most connected, neighbourly communities. Set on a quiet, tree-lined street in Gibson/Stipley South, this is more than a home, it's a place where neighbours know each other, kids play outside, and there's a true sense of community. This beautifully updated 2.5-storey home offers 4 spacious bedrooms and 2.5 bathrooms, blending historic charm with thoughtful modern upgrades. Freshly painted and move-in ready, every space feels warm and refined. At the heart of the home is a stunning renovated kitchen with soaring ceilings, custom cabinetry, stainless steel appliances, granite countertops, and a functional peninsula perfect for everyday living and entertaining. It flows into a welcoming dining area with hardwood floors and an original beam ceiling. The cozy family room features pocket French doors, hardwood flooring, a gas fireplace with natural stone surround, and custom built-ins, the perfect place to unwind. Original character shines throughout with coffered ceilings, walnut trim, solid wood doors, antique hardware, inlay floors, and beautiful stained glass details. Location is everything. Just minutes to Ottawa Street's vibrant shops, cafés, antique markets, and local dining, plus close to Gage Park where you can enjoy trails, the greenhouse, playgrounds, festivals, and year-round outdoor activities. 37 Connaught Avenue South isn't just a home, it's a lifestyle rooted in community, character, and convenience.
Estimate your monthly payments for this property
Estimated Payment
$3,334.32/mo
Includes CMHC insurance ($18,132)
5-yr fixed avg.
Rates shown are estimates based on typical Ontario 5-year fixed rates. Canadian mortgages use semi-annual compounding as required by law. CMHC insurance applies to purchases under $1.5M with less than 20% down. Estimated property tax uses an approximate 0.85% rate. Contact us for current rate options and pre-approval.
Discover Stipley
Stipley is a vibrant community in the Greater Toronto Area, offering excellent amenities, schools, and transportation options. This area is popular with families and professionals seeking a balanced lifestyle with access to urban conveniences and natural spaces.
Why Live in Stipley
- •Convenient location in Hamilton
- •Access to local shops and dining
- •Good public transit connections
- •Community parks and green spaces
- •Well-maintained neighbourhoods
Nearby Schools
Transit & Commuting
- •MiWay bus routes throughout the area
- •GO Transit stations within driving distance
- •Easy highway access to 401/403/QEW
- •Walking distance to local amenities
Parks & Amenities
- •Local parks and recreational facilities
- •Community centres
- •Shopping plazas nearby
- •Restaurants and cafes
Lifestyle & Community
Stipley offers a wonderful quality of life with a mix of residential charm and urban convenience. Residents enjoy easy access to schools, parks, and shopping, making it an ideal location for families and professionals alike.
37 Connaught Avenue, Hamilton
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Rental income estimator & ROI calculator
Monthly Cash Flow Breakdown
Note: These are estimates only. Actual figures may vary based on market conditions, property condition, and other factors. Consult with a financial advisor for personalized advice.

Joe's Thoughts
Honest perspective from 30+ years of GTA real estate experience
Competitive Pricing
At $433/sqft, this is priced below the area average. This could represent genuine value, but let's investigate why. In my experience, underpriced homes often have deferred maintenance, unfavourable layouts, or motivated sellers. I'll help you determine which it is.
Detached Home Advantages
Detached homes in Hamilton are increasingly scarce and valuable. You'll have no shared walls, full control over renovations, and typically stronger appreciation. Consider the lot size and potential for future additions or basement apartment income. Detached homes also offer the most flexibility for growing families.
Excellent Flexibility
With 5 bedrooms, you have genuine flexibility. Beyond the master and kids' rooms, you can have a dedicated home office, guest room, hobby space, or even rental income potential. In today's work-from-home era, extra bedrooms add significant value. Properties with 5+ bedrooms are relatively rare in Hamilton.
Bathroom Count Matters
With 3 bathrooms, morning routines are much smoother. Multiple bathrooms significantly improve daily livability and are a major selling point for resale. Buyers consistently pay more for adequate bathroom counts - this is a strong feature.
About Stipley
I know Stipley well from working with many buyers and sellers here. Each pocket has its own character - let me share what I've learned about this specific street and block. During our showing, I'll point out local amenities, school catchments, and what similar homes have sold for recently.
Investment Perspective
Looking at this as an investment: Hamilton properties have averaged 5-7% annual appreciation over the past decade. Your estimated monthly carrying costs would be around $2,708 (mortgage, taxes, insurance). Consider whether you're comfortable with this as both a home and a financial commitment.