Welcome back to Pick Five! This week, we’re exploring Cliffcrest, a hidden gem in Toronto’s east end that’s quietly transforming. Known for its large lots, quiet streets, and proximity to the Scarborough Bluffs, this area is seeing a wave of redevelopment, with classic bungalows making way for modern luxury homes.

But is Cliffcrest still an undervalued opportunity, or has the market already caught on? Does its proximity to the lake and peaceful, suburban feel justify its growing price tags? And most importantly, is now the time to invest before it’s too late?

In this analysis, we’ll explore five unique properties that showcase Cliffcrest’s evolution, breaking down their value, potential, and how they stack up against Toronto’s more well-known neighborhoods.

Understanding the Cliffcrest Market

Not all up-and-coming neighborhoods follow the same trajectory. Buyers considering Cliffcrest should think about:

• Lot Sizes & Redevelopment – Many homes sit on 45-50 ft lots, rare in Toronto’s core and ideal for custom builds.
• The Bluffs & Waterfront Access – Being near Bluffers Park Beach is a unique draw but also adds seasonal congestion.
• Bungalows vs. New Builds – Is the best value in renovating existing homes or building from scratch?
• Affordability vs. Growth – Can Cliffcrest still offer better value than pricier neighborhoods like Leaside or Lawrence Park?

Property Rundown: Five Homes Defining Cliffcrest’s Future

1. Nealon Ave. – $1.099M | Classic Bungalow with Long-Term Potential

• A 45×133 ft lot priced just over $1M—land value or livable home?
• Built in the 1950s, with an interior that’s functional but dated.
• Purchased in 2022 for $1.455M—now listed at a loss.

2. Brooklawn Ave. – $1.389M | 50-ft Lot with Builder’s Plans

• Turnkey investment—includes architectural plans for redevelopment.
• At 50 ft wide, it meets the gold standard for high-end Toronto lots.
• Already being marketed as a future new build rather than a livable home.

3. Eastville Ave. – $2.75M | Newly Built Luxury Home

• Custom-built in 2022, blending modern and traditional aesthetics.
• Originally listed at $3.1M, now reduced—sign of market cooling?
• Comparable homes in Avenue & Lawrence would sell for $4M+.

4. Lime Regis Crescent – $3.1M | Former Toronto Athlete’s Private Retreat

• Backs onto parkland, offering an exclusive setting with no rear neighbors.
• Spacious 60×112 ft lot, rare in the city.
• Originally purchased for $3.115M—now listed at a loss.

Key Takeaways: What These Properties Reveal About Cliffcrest

1. Cliffcrest’s Evolution Is Happening Now

• The shift from original bungalows to multi-million-dollar new builds is already underway.
• Buyers looking for long-term appreciation could find value before prices climb further.

2. Lot Size Matters—And 50 ft Is the New Benchmark

• Wider lots allow for larger, custom-built homes, making them more desirable for high-end buyers.
• Some buyers will only consider 50-ft frontage, meaning these lots command a premium.

3. Pricing Is Still Attractive Compared to Toronto’s Core

• A similar new build in Leaside or Lawrence Park would cost over $4M.
• Cliffcrest offers larger homes, bigger lots, and proximity to the lake at a lower price point.

4. The Best Buy?

• For investors: Brooklawn Ave. ($1.389M) offers the most redevelopment upside.
• For end-users: Eastville Ave. ($2.75M) is a turnkey luxury home in an emerging neighborhood.

Final Thoughts: Is Cliffcrest Still an Undervalued Gem?

Cliffcrest is no longer just an underrated neighborhood—it’s becoming a hotspot for smart buyers looking for space, value, and long-term growth. With incredible lot sizes, a quiet suburban feel, and close access to the Bluffs, it offers something that downtown Toronto can’t.

Would you invest in Cliffcrest? Do you prefer a classic bungalow or a brand-new luxury home? Let us know in the comments!

Stay tuned for next week’s Pick Five!