27255 Hickory Hill Rd

Brooksville, FL 34602

$3,999,900
Price
6
Beds
6,032 Sq. Ft.
$663 / Sq. Ft.
6,032
Sq. Ft.
$663
per Sq. Ft.
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Description

A rare opportunity to own a truly exceptional 24-acre Brooksville estate offering an unmatched combination of luxury residential living, equestrian potential, industrial capability, and future development flexibility. Designed for both grand-scale entertaining and everyday comfort, the custom 6,700 sq ft main residence features 5 bedrooms, including 3 suite-style bedrooms, 5.5 bathrooms, large executive office, and expansive living spaces including a living, sitting and great room complete with a...A rare opportunity to own a truly exceptional 24-acre Brooksville estate offering an unmatched combination of luxury residential living, equestrian potential, industrial capability, and future development flexibility. Designed for both grand-scale entertaining and everyday comfort, the custom 6,700 sq ft main residence features 5 bedrooms, including 3 suite-style bedrooms, 5.5 bathrooms, large executive office, and expansive living spaces including a living, sitting and great room complete with a full bar. The home is enhanced by 3 fireplaces and an impressive 2,500 sq ft two-story wraparound deck spanning three sides of the residence, along with a pool deck and hot tub designed for outdoor relaxation and entertaining. The home captures panoramic natural surroundings, privacy, and exceptional airflow. For the automotive enthusiast or serious collector, the estate offers extraordinary, fully scalable vehicle capacity exceeding 100 cars in total across multiple structures. The eight-car garage with integrated paint booth provides space for approx. 9 vehicles while also including dedicated storage and a professional-grade paint stall. The 4,800 sq ft high-bay building with 20-foot ceilings and oversized doors can accommodate approximately 18–22 vehicles, RVs, or heavy equipment. The crown jewel is the 24,500 sq ft commercial-grade building, which can house approximately 65–80 vehicles, offering exceptional clear-span interior space ideal for collectors, storage operations, or automotive business use. Additional structures include a 4,800 sq ft high-bay building and a 24,500 sq ft wind-rated commercial-grade facility constructed approximately 12 years ago, featuring 16-foot eaves, a 140 MPH wind rating, and flexible interior layout suitable for industrial, logistics, storage, or event use—making it one of the largest privately owned structures of its kind in the region. Equestrian amenities include a small horse stable and ample acreage suitable for paddocks, riding areas, or expansion. Extensive environmental due diligence has been completed, including a Wetlands Jurisdictional Delineation, Protected Wildlife Species Survey, and full property survey, significantly reducing development risk and streamlining future permitting or subdivision opportunities. The property also features a highly flexible subdivision plan allowing for up to five total parcels, including a primary estate parcel with the main residence and supporting structures, a dedicated commercial/industrial parcel featuring the 24,500 sq ft building, and three additional residential lots ideal for custom homes, guest estates, or resale potential. Offering nearly 36,000 sq ft of enclosed structures across the estate and unmatched vehicle storage capacity exceeding 100 cars, this property is ideally suited for private estate ownership, multi-generational compound living, agricultural or equestrian operations, or a high-value investment and redevelopment strategy. A truly one-of-a-kind!
  1. Listed by Char Seuffert • Re/Max Sunshine • char@remaxsunshine.com

Property Details for 27255 Hickory Hill Road

Development
SPRING LAKES
Building Design
Single Family
Community Type
Non-Gated
Waterfront
No
Waterfront Desc
None
Waterfront Desc
None
View
Wooded Area
Garage Spaces
100.00
LISTING UPDATED: 06/24/2026 08:15 PM

Property Details for 27255 Hickory Hill Road

StatusActive
MLS #2026026698
Days on Market11
Taxes$23,097 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1988
Lot Size24.80 AC / 1,080,288 SF
CountyHernando County
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Location

Listing Courtesy of Re/Max Sunshine, Char Seuffert
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Building Information for 27255 Hickory Hill Road

Stories3Year Built1988Building Size-Lot Size24.80 AC / 1,080,288 SF

Payment Calculator

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$21,857 per month

30 year fixed, 6.36% Interest

Principal and Interest

$19,932

Property Taxes

$1,925

HOA Dues

$0

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Property Information for 27255 Hickory Hill Road

Summary
Location and General Information
  • City: Brooksville
  • Directions: Spectacular offering and the ultimate for car collectors!
  • Human Modified: No
  • Latitude: 28.48
  • Longitude: -82.29
  • MLS Area Major: OA01 - Out of Area
  • Pets: No Approval Needed
  • Postal Code: 34602
  • Street Name: HICKORY HILL
  • Street Number: 27255
  • Street Suffix: RD
  • Block: 0010
  • Full Address: 27255 HICKORY HILL RD
Parking
  • Attached Garage: No
  • Carport Spaces: .00
  • Carport: No
  • Covered Spaces: 100.00
  • Garage: Yes
  • Parking Features: Detached, Garage, Rv Access Parking, Garage Door Opener
Taxes and HOA Information
  • Amenity Rec Fee: $.00
  • Application Fee: $.00
  • Association Fee Total: $.00
  • Association Fee Total Frequency: Annually
  • Association Fee 2: $.00
  • Maintenance: None
  • Mandatory HOA: No
  • Tax Annual Amount: $23,097.00
  • Tax Year: 2025
  • Transfer Fee: $.00
  • Association Fee 3: $.00
Property
Lot Information
  • Source of Measure Total Area: Appraiser
  • Development Name: SPRING LAKES
  • Parcel Number: R15 423 20 0000 0010 0050
  • Property Type: Residential
  • Section: 15
  • Lot Unit: 0050
  • Source of Measure Living Area: Appraiser
  • Source of Measure Lot Dimensions: Appraiser
  • Lot Desc: Multiple Lots, Oversized Lot
  • Acres: 24.8
  • Lot Size Area: 24.8
  • Lot Size Dimensions: 675 x 1650 x 1560 x 1550
  • Source of Measurements: Appraiser
  • Lot Size Units: Acres
  • Legal Desc: 24.8 ACRES MOL IN S1/2 OF SE1/4 DES IN ORB 579 PG 527 & ORB 724 PG 658 LESS 4.9 AC MOLDES IN ORB 725 PG 90 & SUBJ TO DESC IN ORB 1282 PG 150 & SUBJ
Property and Assessments
  • Total Area: 6700.0
  • Rear Exposure: E
  • Approx Living Area: 6032.0
  • Possession: Close Of Escrow
  • Property Condition: Resale
  • Property Sub Type: Single Family Residence
  • Township: 23
  • Senior Community: false
  • Range: 20
  • Special Assessment: 0.00
  • Sub Condo Name: SPRING LAKES
  • Year Built Numeric: 1988
  • Property Sub Type Additional: Single Family Residence
  • Restrictions: No Restrictions
Lease Information
  • Land Lease Fee: $.00
  • One Time Land Lease Fee: $.00
  • One Time Mandatory Club Fee: $.00
  • One Time Othe Fee: $.00
  • One Time Special Assessment Fee: $.00
Utilities
  • Sewer: Private
  • Utilities: Cable Available
  • Water Source: Public
  • Water: Central
Multi Family
Multi-Family Information
  • Num Unit Floor: 0
  • Annual Food And Beverage Minimum: 0.00
  • Units in Complex: 0
  • Stories: 2.0
  • Total Floors: 3
  • Total One Time Fees: $.00
  • Units in Building: 0
  • Unit Location: 0
Interior and Exterior Features
Exterior Features
  • Architectural Style: Other, Two Story, Split Level, See Remarks
  • Canal Width: None
  • Community Features: Non Gated
  • Construction: Poured Concrete, Concrete Block
  • Exterior Features: Deck, Other, Patio
  • Exterior Features: Deck, Patio, Barn Stall
  • Irrigation Source: Other
  • Other Structures: Barns
  • Patio And Porch Features: Deck, Lanai, Open, Patio, Porch, Screened
  • Pool Features: Electric Heat, Heated, In Ground, Screen Enclosure
  • Private Pool: Yes
  • Roof: Shingle
  • Security Features: Smoke Detectors
  • Gulf Access: No
  • Spa: Yes
Interior Features
  • Appliances: Dishwasher, Microwave, Range, Refrigerator
  • Baths Full: 5
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 6.0
  • Beds Total: 6
  • Bedrooms: 6 or More
  • Cooling: Central Air, Electric, Other
  • Cooling: Yes
  • Elevator Text Details: None
  • Flooring: Carpet, Tile
  • Furnished Desc: Unfurnished
  • Heating: Central, Electric
  • Heating: Yes
  • Interior Features: Breakfast Bar, Closet Cabinetry, Separate Formal Dining Room, Dual Sinks, Kitchen Island, Vaulted Ceilings, Bar, Walk In Closets, Split Bedrooms
  • Interior Features: Closet Cabinets, Vaulted Ceiling, Bar, Walk-In Closet, Smoke Detectors
  • Laundry Features: Washer Hookup, Dryer Hookup, Inside
  • Levels: Two, Multi Split
  • Rooms Total: 0
  • Spa Features: Electric Heat, In Ground, Screened
  • Window Features: Double Hung, Sliding
Rental
Rental Information
  • Horse Amenities: Horses Allowed, Stables
  • HorseYN: Yes
  • One Time Rec Lease Fee: $.00

Property History for 27255 Hickory Hill Road

DateEvent & SourcePriceAppreciation
Jun 24, 2026

Listed (Active)

MiamiRE #A12039048

$3,999,900—
Jun 22, 2026

Listed (Active)

FORTMLS #2026026698

$3,999,900—
Feb 5, 2014

Sold

SASJMLS #HC2137704

$1,340,000—
DateEvent & SourcePrice
06/24/2026

Listed (Active)

MiamiRE #A12039048

$3,999,900
06/22/2026

Listed (Active)

FORTMLS #2026026698

$3,999,900
02/05/2014

Sold

SASJMLS #HC2137704

$1,340,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 27255 Hickory Hill Road

Taxable ValueLand-Additions-Total-
Tax Record2025$23,097 ($1,925 / month)
Home Facts
Beds6Total Finished SqFt25,500 SqFtAbove Grade Finished SqFt25,500 SqFtStories1Lot Size1,080,288 SqFtStyleSingle Family ResidenceYear Built1988Year Renovated1998CountyHERNANDOAPNR15-423-20-0000-0010-0050Fireplace TypeHas Fireplace

Schools near 27255 Hickory Hill Road

This home is within Hernando.
Rating
School
Type
Grades
Distance
Eastside Elementary School
Public - PK to 5
D. S. Parrott Middle School
Public - 6 to 8
Hernando High School
Public - 6 to 12
Center for Success and Independence Brooksville Academy
Public - 6 to 12
Rating
School
Distance
Eastside Elementary School
PublicPK to 5

D. S. Parrott Middle School
Public6 to 8

Hernando High School
Public6 to 12

Center for Success and Independence Brooksville Academy
Public6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 27255 Hickory Hill Road, Brooksville, FL 34602

27255 Hickory Hill Road is a single family home for sale in Brooksville, FL 34602. This property was listed for sale on June 22, 2026 by Re/Max Sunshine, it's currently listed at $3,999,900. It has been on the market for a total of 11 days and was last sold on February 5, 2014. This listing's school district is Hernando. Nearby schools include Eastside Elementary School, D. S. Parrott Middle School and Hernando High School. 27255 Hickory Hill Road is a 6-bed, 6-bath, 6,032 sqft single family home built in 1988.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Re/Max Sunshine, Char Seuffert

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 06/24/2026 08:15 PM