Published March 30, 2026

$1M+ Homes Near Tallahassee: Featured Equestrian Property on Kiley Drive with pool house & vineyards

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Written by Meredith Carter

An equestrian-ready private retreat just minutes from Tallahassee

Luxury Estate Near Tallahassee with Acreage: 221 Kiley Drive in Monticello, FL

An equestrian-ready private retreat just minutes from Tallahassee


A Rare Opportunity Just Outside Tallahassee

If you’ve been searching for a luxury home near Tallahassee with land, you’ve likely noticed how rare it is to find a property that truly offers both privacy and proximity.

Located just a short drive from Tallahassee, 221 Kiley Drive in Monticello, FL presents a unique opportunity to own a private estate on acreage—without giving up access to the city’s dining, shopping, and everyday conveniences.

This is where buyers are starting to look when they want more space, more freedom, and more lifestyle.


Why Buyers Are Expanding Beyond Tallahassee

Luxury buyers are increasingly prioritizing:

  • Privacy and quiet surroundings
  • Usable land and long-term flexibility
  • Space for recreation, entertaining, or expansion

Properties like this offer something that’s becoming harder to find within Tallahassee city limits—room to live the lifestyle, not just own a home.


A Home Designed for Space, Comfort, and Entertaining

Inside, the home features a spacious, open-concept layout with abundant natural light and thoughtful design throughout.

Highlights include:

  • Expansive living areas ideal for hosting
  • Seamless flow between indoor and outdoor spaces
  • Timeless finishes that balance comfort and style

Whether you’re entertaining guests or enjoying a quiet evening, the layout is designed to make everyday living feel elevated.


Equestrian Potential & Endless Possibilities

For buyers searching for a horse property near Tallahassee, this estate offers incredible potential.

With generous acreage and open space, the property is well-suited for:

  • Horses and equestrian use
  • Building a barn, paddocks, or riding areas
  • Recreational use or future expansion

It’s rare to find a property this close to Tallahassee that offers this level of flexibility and land use potential.


The Lifestyle: Privacy, Nature, and Convenience

Step outside and you’ll immediately feel the difference.

This property offers:

  • Wide-open views and peaceful surroundings
  • Privacy from neighbors and city noise
  • Space to create your own vision—whether that’s a family retreat, equestrian setup, or legacy estate

And yet, you’re still just minutes from Tallahassee—making it the ideal balance of escape and accessibility.


Who This Property Is Perfect For

221 Kiley Drive is ideal for buyers who:

  • Want a luxury home near Tallahassee without being in the city
  • Are searching for acreage or a horse property
  • Value privacy, space, and long-term potential
  • Are looking for a lifestyle-driven purchase, not just a house

Schedule a Private Tour

Properties like this don’t come around often—especially with this combination of location, land, and opportunity.

If you’re searching for a Tallahassee-area luxury estate or equestrian property, this is one you’ll want to experience in person.

đź“© Reach out to schedule your private showing of 221 Kiley Drive and see what makes this property truly special.

Listed by Wilda Sigler, Realtor

850-888-5832

wildasigler@kw.com


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Neighborhood Spotlights, Purchasing

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