Active Under Contract

Residential

221 KILEY Drive

Monticello, FL 32344

Beds

5

Baths

5

Square Ft.

5,476

$1,325,000

Welcome to a rare North Florida estate just minutes from Tallahassee—where luxury, land, and lifestyle come together. 221 Kiley Road is situated on expansive acreage in Monticello, and this private retreat offers the perfect blend of seclusion and convenience, located just a short drive from the heart of Tallahassee.… Read More For buyers seeking space, privacy, and versatility without sacrificing proximity to town, this property delivers. 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, this Tallahassee luxury home alternative 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. Read Less

Listing Snapshot

Days Online

182

Last Updated

Aug 7, 2026

Property Type

Single Family Residence

Beds

5

Full Baths

4

Partial Baths

1

Square Ft.

5,476

Lot Size

5 Acres

Year Built

2009

MLS Number

395876

Additional Details

Property Access

Road responsibility: PrivateMaintainedRoad, Road surface type: Paved

Appliances & Equipment

Dryer, Dishwasher, IceMaker, Microwave, Oven, Range, Refrigerator, Washer, Generator

Building

Built in 2009, Architectural style: TwoStory, SplitLevel, Traditional, Construction materials: Brick, Levels: MultiSplit, Toal building area: 5476

Cooling

CentralAir, CeilingFans, Electric

Exterior Features

SprinklerIrrigation

Fireplaces

Gas

Floors

Bamboo, Tile

Garage

3 garage spaces

Heating

Central, Fireplaces

Home Owner's Association

Association fee: $150

Interior Features

WetBar, TrayCeilings, GardenTubRomanTub, HighCeilings, StallShower, VaultedCeilings, CentralVacuum, EntranceFoyer, PrimaryDownstairs, Pantry, SplitBedrooms, SunRoom, WalkInClosets

Lot

5 acres

Parking

ThreeCarGarage, ThreeOrMoreSpaces, Gated

Pets Policy

Horse amenities: HorsesAllowed

Pool

Concrete, InGround, PoolEquipment

Property

Patio and porch features: Covered, Patio, Porch, Screened, ParkGreenbelt

Security Features

SecuritySystemOwned

Sewer

SepticTank

Courtesy of Keller Williams Town & Country 850-201-4663

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