5 Old Houses that are Ideal for Entertaining

39 Old Snake Hill Road, Pound Ridge, NY

I love my apartment, and it’s in a really lovely historic building. When guests come over, though, I’m reminded that it is definitely only outfitted for two people. Especially if eating is involved. That leads to dreaming about wet bars, dining rooms that can fit 8 people comfortably, pools, guest cottages… that kind of thing. Do you also wish you had a compound to house all of your friends like a wacky, adult summer camp? Dream over these.

1. 1076 59th Street, Oakland, CA  – $2,800,000

7 beds/5 baths 
5,356 sqft, 0.34 acres

The DeRome House mansion is a perfect place to get started because it is practically a fun house made for entertaining large groups. It also majorly delivers on architectural detail – the exterior facade will have your guests frothing before they’re even in the driveway. The main house has tons of space and a billiard room, there are outdoor seating options aplenty, and there are two updated studio/guest cottages for housing everyone comfortably. Everyone can crash in style at this compound.

Visit the full listing here.


2. 308 Titicus Road, North Salem, NY  – $999,000

4 beds/3.1 baths
3,669 sqft, 5.5 acres

This updated 1840s farmhouse has been really thoughtfully restored. It’s newly painted and fresh but the wide plank flooring, three working fireplaces, exposed beams and appropriate color scheme keep the colonial warmth in-tact. The open space created between the kitchen and living area is definitely the most modern update, but it sure facilitates entertaining! There’s also a spacious dining room, separate wet bar, and a pool! The property backs up to a 1200 acre property that’s perfect for hiking, too.

Visit the full listing here.


3. 39 Old Snake Hill Road, Pound Ridge, NY – $1,250,000

4 beds/3.1 baths
3,049 sqft, 5.78 acres

Known as the Rock House, this Arts & Crafts stone home offers stunning views of the Blue Ridge Mountains, along with this bright reading space.

Visit the full listing here.


4. 40 Otter Rock Drive, Greenwich, CT – $7,950,000

8 beds/5.3 baths
7,362 sqft, 1.59 acres

The Lawson Cottage is a sprawling estate with multiple porches, fabulous pool, and impeccable details. There are so many luxury details here, including mahogany paneling, coffered ceilings, parquet floors and stained glass. The landscaping is also remarkable! Host a pool party and have space to house all of your guests.

Visit the full listing here.



The Perfect Gifts for the Old House Lover in Your Life.

“I Love Old Houses”
Book Tote


Wool Felt Pennant


Mini Brownstone
Enamel Pin


There’s More!

Alix is CIRCA’s Properties Manager. She relishes working directly with homeowners and real estate agents to track down new stewards for homes with secrets to keep and stories to tell! On a lifetime mission to visit every great flea market in the world, she’s probably going to need a bigger old house soon.

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