$749,900 - 1999 Main Street, Hamilton
Detached for Sale in Hamilton
Neighbourhood: Ainslie Wood
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- MLS Number
- X13780774
- Property Type
- Detached
- Status
- active
- Days on Site
- 23
- Bedrooms
- 2
- Bathrooms
- 1
- Square Feet
- 700 - 1,099 sqft
- Neighbourhood
- Hamilton
- Lot Size
- 13,465 sqft
- Taxes (2026)
- $5,529
- Listing Brokerage
- KELLER WILLIAMS EDGE REALTY
Charming & Cozy in a Storybook Setting! Nestled among mature trees on an impressive 50' x 288' lot, this enchanting 2-bedroom home offers exceptional privacy, timeless character and a Muskoka-inspired setting on the Hamilton-Ancaster border. Surrounded by conservation areas,parks and scenic walking/hiking trails, yet just minutes to the LINC, Hwy 403, Downtown Hamilton, Dundas, Ancaster Village, McMaster University and McMaster Children's Hospital. The inviting interior features a thoughtfully renovated kitchen with open shelving, deep pot-and-pan drawers, stainless steel appliances and engineered hardwood flooring. Rich hardwood floors flow through the living and dining rooms and both bedrooms, adding warmth and character throughout. The living room features a cozy wood-burning fireplace, creating an ideal space to relax or entertain. A bright sunroom offers peaceful views of the expansive backyard and provides the perfect spot for morning coffee, reading or unwinding at the end of the day. Recent updates include a beautifully renovated kitchen and bathroom plus a brand-new heat pump with cooling,combining modern comfort with the home's original charm. The basement, conveniently accessed from the sunroom, offers a dedicated laundry area and additional storage. Outside, the expansive backyard provides plenty of room to enjoy, while the detached 1.5-car garage offers additional parking and storage. The extended driveway accommodates up to six vehicles-ideal for family gatherings and entertaining. Lovingly maintained and decorated in timeless neutral tones, this warm and welcoming home delivers the rare combination of privacy, character, outdoor space and unbeatable convenience. Enjoy the feel of a country retreat with the city, highways, amenities and McMaster University just minutes away. A truly special property in an exceptional location!
Estimate your monthly payments for this property
Estimated Payment
$3,847.38/mo
Includes CMHC insurance ($20,922)
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 Ainslie Wood
Ainslie Wood 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 Ainslie Wood
- •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
Ainslie Wood 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.
1999 Main Street, Hamilton
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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
Fair Market Value
At $1071/sqft, this property is priced in line with current Hamilton market conditions. The pricing suggests the seller has done their homework. We may have modest room for negotiation, typically 2-4% in today's market.
Market Position
At 23 days on site, this property has had reasonable exposure. It hasn't sold immediately (which often indicates overpricing), but isn't languishing either. There's likely room for a 3-5% negotiation from asking price.
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.
Efficient Living
At 700 sqft, this is a more compact space. The upside: lower utility bills, less maintenance, and easier cleaning. Consider how you'll use the space - built-in storage, multi-functional furniture, and good organization become important. Great for singles, couples, or those who prefer a low-maintenance lifestyle.
About Ainslie Wood
I know Ainslie Wood 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 $3,125 (mortgage, taxes, insurance). Consider whether you're comfortable with this as both a home and a financial commitment.








































