The 5 Most Tightly Held Streets in Caulfield North — And Why Locals Never Leave

In Caulfield North, prestige isn’t just about postcode — it’s about permanence.

While some streets see homes turn over every few years, others are different. On these streets, families settle in for decades. Homes are passed down. Listings are rare. And when they do hit the market, they often spark bidding wars.

These are Caulfield North’s most tightly held streets — where owners rarely sell, and when they do, it’s seen as a generational opportunity.

Here are the top five.

1. Manor Grove

Location: Off Orrong Road, near Balaclava Road Google Maps: View Manor Grove

• Just seven freestanding homes

• Backs onto the historic Labassa Mansion

• Not visible from any major road — most locals don’t even know it exists

• Fewer than five sales in recent memory

Manor Grove is arguably the most discreet and tightly held street in Caulfield North. The lack of through traffic, the prestige of the neighbouring mansion, and the sheer rarity of its homes make it a street buyers watch for years — often without ever seeing a “For Sale” sign.

2. Malvern Grove

Location: Between Park Crescent and Inkerman Road Google Maps: View Malvern Grove

• Borders Caulfield Park

• Long stretches of period homes and villas

• Known for 50+ year ownerships and limited turnover

• Frequently described by agents as “tightly held”

Malvern Grove has broad appeal: parkside access, leafy charm, and a long-standing reputation. It’s a classic Caulfield North street where prestige meets patience — homeowners here rarely leave.

3. Rosemont Avenue

Location: Off Balaclava Road, near Halstead Street Google Maps: View Rosemont Avenue 

• Wide, elegant street with generous blocks

• Known for grand homes and quiet presence

• Properties often stay in the same family for multiple generations

Rosemont Avenue is one of Caulfield North’s most celebrated streets — and one of the hardest to buy into. Real estate agents frequently describe it as a rare opportunity whenever a listing surfaces — because those listings are few and far between.

4. Ontario Street

Location: Near Balaclava Road and Halstead Street Google Maps: View Ontario Street 

• Located in the heart of the Golden Mile

• Most properties held since the 1970s or earlier

• Listings are considered high-prestige and attract significant interest

Ontario Street’s large blocks and well-maintained period homes are hallmarks of this prestige pocket. Many of its homes have never been publicly listed — changing hands only once every few decades.

5. Octavius Avenue

Location: Off Inkerman Road, between Howitt and Aroona Roads Google Maps: View Octavius Avenue 

• A true cul-de-sac with no through traffic

• Known for long-term residents and family-friendly privacy

• Example: One recent sale marked the first change of hands in 18 years

Octavius Avenue is a small but powerful example of why cul-de-sacs dominate this list. Tightly held by design and by community, it embodies the type of location where people move in and simply stay.

Why Do People Stay So Long?

Each of these streets offers something beyond just location: a feeling of stability, heritage, and community. They’re not just addresses — they’re legacies.

If you’re lucky enough to live on one of them, you already know why.

And if you're not — you may be waiting a while.