St. Andrew-Windfields Real Estate Report · Week of May 25 | $4.4M Median

The week in numbers

St. Andrew-Windfields recorded three sales in the week ending May 25, with a median sold price of $4.4 million. Sales ranged from $2.1 million to $5.1 million, reflecting the neighborhood’s positioning at the luxury end of the Toronto market. All three properties sold below asking, a pattern consistent with the broader premium segment’s pricing reality.

Local home values: see what homes are selling for in Toronto with our free Toronto home value calculator.

The 6.4% average discount from list price reflects realistic pricing expectations in this segment. With only three sales, week-to-week volatility is expected; these numbers should be read as a snapshot rather than a definitive trend.

What sold

All three properties that moved this week were detached homes at the high end of the market. Two exceeded $4 million; the third, on Tullamore Drive, sold for $2.13 million after listing at $2.19 million. The $5.1 million sale on Truman Road represents the week’s peak transaction. Properties ranged from approximately 3,000 to over 5,000 square feet, typical of the estate-scale homes that define the neighborhood.

Price-per-square-foot metrics are difficult to calculate precisely given the range bands provided in the data, but the three sales suggest a broad valuation spread reflecting lot size, condition, and location variation within the neighborhood.

• Truman Road: $5,100,000, Detached, 5,000+ sqft
• Foursome Crescent: $4,400,000, Detached, 3,500-5,000 sqft
• Tullamore Drive: $2,128,880, Detached, 3,000-3,500 sqft

What’s listed right now

Eight properties are currently listed in St. Andrew-Windfields, ranging from $2.49 million to $5.5 million. The median list price across active inventory is approximately $4.07 million, slightly below the week’s median sold price. This suggests a modestly balanced supply-and-demand picture, with enough choices for serious buyers but not saturation.

• Legacy Court: $5,500,000
• Cotswold Crescent: $5,125,000
• Yorkminster Road: $4,850,000
• Owen Boulevard: $4,288,000
• Yorkminster Road: $3,650,000 (note: separate listing on same street)
• Vernham Court: $3,380,000
• Beaverhall Drive: $2,799,999
• Montressor Drive: $2,488,000

Market call

With only three sales in a week, any directional call is preliminary. That said, the 6.4% average markdown from list suggests sellers are pricing realistically and buyers have negotiating room at the top of the market. The sale-to-list ratio of 0.936 sits comfortably in a balanced range; neither desperation nor runaway demand is evident.

Days-on-market data was not available for this week’s sales, so we cannot assess velocity. Given the sample size, treat this week as a data point rather than a trend. Interested sellers should consult the seller net sheet calculator to model their expected proceeds; interested buyers should consider booking time with a licensed representative to understand the nuances of the segment.

How this compares to the broader North York

St. Andrew-Windfields sits at the premium end of North York’s residential market. The $4.4 million median this week is substantially above the broader Ontario median, which typically hovers around $1 million to $1.2 million depending on mix and timing. The neighborhood commands a luxury premium reflective of its proximity to established neighborhoods, lot sizes, and school proximity. The broader North York market sees more inventory and transaction volume; St. Andrew-Windfields is a select subset with correspondingly selective buyer pools.

What this means if you’re thinking of selling

If you own in St. Andrew-Windfields, the current market offers realistic exit opportunities with modest discounting baked in. The presence of eight active listings suggests competition for buyer attention; pricing and presentation matter. We recommend starting with the pre-listing checklist to ensure your property is positioned for the luxury buyer segment, then using the net sheet calculator to model various price scenarios and holding costs. Professional staging and photography are not optional at this price point. If you are considering a move, a brief consultation can clarify timeline and strategy.

What this means if you’re thinking of buying

Buyers in this segment should recognize that eight active listings at these price points offer choice. The 6.4% average discount suggests room for negotiation, particularly on properties that have been listed longer. However, estate homes in St. Andrew-Windfields attract international and institutional buyers; the market can shift quickly. Alex is licensed to represent buyers and can facilitate a detailed walkthrough tailored to your priorities. Book a 20-minute walkthrough to explore current options or to discuss the neighborhood’s nuances and your timeline.

Sources & method

Data for this report was drawn from MLS records via Repliers, covering the seven-day period ending May 25, 2026. The report reflects three completed sales and eight active listings as of the reporting date. For broader market context and recent Ontario MLS data, see City of Toronto Open Data. You can also view St. Andrew-Windfields home value estimates or return to InstantCalculator.ca for additional tools and reports.