Six years after the pandemic, the world looks different. Remote work is here to stay. Delivery services keep getting faster and sharper. Families are finding new rhythms, splitting time between offices, kitchens, and living rooms. But the biggest shift? People have rediscovered the joy of being together—craving connection after all those isolated days.

That pull for community is colliding with something else entirely: a great wealth transfer already in motion—the “Silver Tsunami.” As we detailed in our 2026 Red Paper Mid-Year Report, an estimated $124 trillion will be transferred down through 2048, with Boomers passing assets to millennials and Gen X. In real estate, this translates to a surge in multi-generational living—properties that balance privacy and space with shared experiences, whether with family, friends, or both. As The Agency Hamptons Managing Partner Dana Trotter puts it, “families are increasingly seeking flexibility and shared experiences over simple square footage.”

Here, we’re featuring eight distinctive estates across The Agency’s portfolio that offer just that—expansive properties intentionally designed with flexible living arrangements through guest homes, detached ADUs, acreage, and more. Let’s take a look around.

Bath Springs, Tennessee
900 Ed Renfroe Circle Listed by Amy Doyle & Scott Coggins

This 661-acre organic farm reimagines the family compound, combining a private luxury residence with a working Wagyu cattle operation, protected wetlands, certified Great Blue Heron rookery, and abundant open space that creates opportunities for generations to live, gather, and build a lasting legacy. The home, which has never been on the market, was built four years ago, and the land is the highest priced in the county, with soil samples showing it is more fertile than 65% of the county. In addition to mature timber, the entire farm is organic, and all of the animals are free of hormones and antibiotics. This is a property ripe with possibility, just waiting for its next steward.

Hickory Creek, Texas
121 Harbor Lane Listed by Lynda Villarreal

This grand 50-acre legacy estate just outside Dallas features multiple living spaces, guest suites, caretaker apartments, resort-style outdoor amenities, and extensive grounds designed for entertaining, recreation and generations of family living. The main home, a modern farmhouse, features impeccable craftsmanship and spectacular interiors by Kirsten Kelli Interior Design.

San Juan Island, Washington Halftide Farms Listed by Jen Cameron and Jonathan Ruiz 

Curated over three decades and built by Schultz Miller, the estate spans approximately 19,000 square feet across six structures, including three primary residences (each around 4,000 square feet), called The Beach House, The Farm House, and The Field House. All three also have their own guest cottage, and additional structures include a bunkhouse, game house, and caretaker’s residence. The secluded 90-acre waterfront property enjoys beautiful beach frontage, breathtaking mountain views, and offers an exceptional setting for generations to gather while enjoying complete privacy.

Bend, Oregon
61465 White Peaks Court Listed by Matt Robinson

Designed specifically for multi-generational living, this custom estate features a seamlessly integrated secondary residence complete with its own kitchen, living room, bedroom, and garage, offering privacy and independence while keeping family close. Completed in 2019, this luxuriously appointed home on 2.61 private acres boasts a central open great room with massive vaulted ceilings, custom wood beam accents, and sweeping views of the surrounding plains and distant mountains.

Gallatin Gateway, Montana
1021 Gateway South Road Listed by Joy Vance

Blending Montana ranch living with luxury entertaining, A River’s Ranch encompasses a 6,612-square-foot main log home, a guest house, extensive equestrian facilities, private Gallatin River frontage, and expansive gathering spaces designed for family and friends. Spanning over 55 usable acres across both banks of the West Gallatin River, the property is a once-in-a-generation ranch—minutes from Bozeman, Yellowstone, and Big Sky, yet a world entirely its own.

Zionsville, Indiana
9825 Windy Hills Drive Listed by Traci Garontakos

Perched atop nearly five lakefront acres, this 25,000-square-foot estate invites families of all sizes to enjoy the best of waterfront living. The home features three kitchens, six generous ensuite bedrooms, and various exceptional entertainment spaces including a two-lane bowling alley—all geared towards bringing family and friends together on an extraordinary scale. Imagined by renowned designer Gary Nance, the home overlooks a 35-acre lake and the vast lands beyond, with 2.5-acre building sites on either side of the home.

Steamboat Springs, Colorado
Meadow House at Storm Mountain Ranch Listed by Chris Paoli

Set within the exclusive Storm Mountain Ranch community and designed by Aspen-based architect Michael Ernemann, Meadow House sits where open ranch meadows meet aspen groves. The residence pairs dual primary suites, a private guest suite, and gathering spaces with stunning valley views. The 70-acre parcel provides a setting for all four seasons, connecting directly to the Storm Mountain Ranch trail system— 793 acres of protected land under three permanent easements, including stocked fishing ponds, Orvis-approved streams, a private lodge, dedicated ranch staff, and five private cabins, including one at the base of a waterfall, which is reserved solely for owners and their guests.

Rancho Santa Fe, California
5758 Las Palomas Listed by Craig Lotzof

Set beyond gates in Rancho Santa Fe, find approximately 6,109 square feet of impeccably curated living space with soaring ceilings, clean architectural lines, and walls of glass that bathe the interiors in natural light. This newly constructed modern Santa Barbara estate pairs five ensuite bedrooms with a detached guest house, creating a flexible retreat that balances privacy and togetherness for multigenerational families in one of Southern California’s most prestigious communities.