221 Kiley Dr, Monticello, FL

House

For Sale

Listed price in listed location currency (USD).

$1,325,000

550

MLS® 395876

Key Facts
Description
Map

Key Facts

Type Single Family Residence

Levels Residential

Size 5476 sqft

Garage Yes

Taxes $8,073

Days Active 0

Lot Size 5 acres

Approx. Age 2009

Avg. Price Per Sqft $241

MLS® Number 395876

Property Address: 221 Kiley Dr, Monticello, FL, 32344-3983

Average square foot calculated using Size range provided by listing agent.

Description

Welcome to 221 Kiley Road in Monticello, Florida — a rare estate where vineyard charm, equestrian living, and exceptional space come together to create an unforgettable lifestyle. This 5-bedroom, 3.5-bathroom estate is a true masterpiece, gracefully set on 5 private acres and complemented by a beautiful pool house with an additional bathroom. An additional adjoining 5-acre parcel is also available, offering the rare opportunity to expand your privacy, create a multi-generational compound, or enhance the estate even further. Set on picturesque rolling land, this one-of-a-kind property features your own private vineyard, offering a breathtaking and romantic backdrop for everyday living and entertaining. Imagine sunset dinners overlooking the vines, peaceful morning walks through the rows, or simply enjoying the beauty and serenity that only a setting like this can provide. Equestrian enthusiasts will appreciate the well-appointed horse stable, open pasture, and room to ride, creating the perfect environment for both horses and riders to thrive. Thoughtfully designed for function and beauty, the grounds invite you to embrace true North Florida country living. At the heart of the property sits an impressive residence offering approximately 5, 500 square feet of living space, ideal for large households, multi-generational living, or those who love to entertain. The thoughtfully designed layout features expansive living areas filled with natural light, a spacious kitchen with abundant cabinetry and workspace, and oversized bedrooms that serve as peaceful private retreats. Multiple flex spaces provide endless possibilities for home offices, media rooms, fitness areas, hobby spaces, or additional guest accommodations — tailored to fit your lifestyle. Step outside to your private pool oasis, perfect for relaxing afternoons or hosting unforgettable gatherings. A separate guest house offers comfortable accommodations for visitors, extended family, or a private retreat, adding flexibility and value to this exceptional estate. From vineyard evenings and horseback mornings to poolside afternoons, 221 Kiley Road is more than a home — it’s a lifestyle. Offering space, versatility, natural beauty, and privacy while still convenient to downtown Monticello, schools, shopping, and dining, this is a truly rare opportunity to own a remarkable property where memories are made for generations.

MLS® Number395876

Laundry Level

Central VacNo

FireplaceNo

Acreage5

Exterior

GarageYes

Approx. Age2009

Basement

DrivewayThree Car Garage, Three Or More Spaces, Gated

Garage Spaces3

Heat

A/C

Heating Fuel

Extras

Price History

-End Date

Not Sold YetSold Price

For Sale

Feb 6, 2026List Date

$1,325,000List Price

Commute

Commute

Starting Address

Destination Address

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