65 Olive Street
Brooksville, FL 34601

For Sale - Active

offered at $599,000

3

bedrooms

3

baths

1,961

sq ft

$305

price per sf

Single Family

property type

133 Days

time on site

1910

yr. built

0.48 acre

lot size

Rare Double Residential Property with two Century Homes in Historic Downtown Brooksville on a HUGE oversized corner lot at the corner of two of Brooksville's most desired roads...Olive Street and Bell Ave, both roads are made from historic bricks and are lined by century-old grandfather live oak majestic trees!! Just the location will take your breath away!! The main home, built in 1920, offers 1,961 sq feet of living space + 3 bedrooms (can be 4) + 3 bathrooms + gorgeous parlor rooms + a gorgeous brick front porch + built with all the character only a century old home can offer you! A brick wood burning fireplace takes you back in time when this home was one of t...he town's elite beauties!! NEW ROOF on both homes!! The second century home was built in 1910, and offers just under 1,000 sq feet of living space + 1 bedroom + 1 bathroom. It is 2-stories with a private balcony overlooking historic Bell Ave!! The two Century Homes are joined by a beautiful, private gazebo to enjoy your morning coffee or evening drinks to relax...and host your family gatherings and celebrations like they did over 100 years ago!! The rare property is surrounded by churches and majestic trees! The second home can be a guest home for your guests when they visit, or a rental-income property for a long term rental or turn it into an Airbnb's with short term rentals welcoming guests to Historic Downtown Brooksville as it is in walking distance to everything amazing Brooksville has to offer from local festivals, arts and crafts shows, music on the square, dining under the stars on Main Street, horse-drawn carriage rides at Christmas with the lighting of the Christmas Tree, the parades, and all the Hallmark Town experiences Brooksville offers!! All the character, all the charm, all the history, all the potential...this incredible property offers so much!! Come take a look...step back in time...and image a life as it was once lived in its glory of our town's history...and then make it your own! Honor its history, honor its location, and enjoy a life well-lived in a home built with care and love...not a track home built to look like every other home in the street. Take a stroll back in time and come view this amazing property!! Only 45 minutes north of Tampa!!

Stellar MLS, MLS#: W7886886

Listed By: HOME LAND REAL ESTATE INC, 352-556-0909

No upcoming open house dates. Check back later.

Bedrooms

Total Bedrooms: 3

Bathrooms

Full bathrooms: 3

Appliances

Dishwasher
Microwave
Range
Refrigerator

Construction Materials

Frame

Cooling

Central Air

Exterior Features

Lighting
Rain Gutters
Sidewalk

Fireplace Features

Wood Burning

Flooring

Ceramic Tile
Wood

Foundation Details

Concrete Perimeter
Pillar/Post/Pier

Heating

Central
Electric

Interior Features

Ceiling Fans(s)
Crown Molding

Laundry Features

Inside
Laundry Room

Levels

Lot Features

Corner Lot

Other Structures

Guest House

Parking Features

Circular Driveway

Patio and Porch Features

Deck
Front Porch
Patio
Rear Porch

Road Responsibility

Public Maintained Road

Road Surface Type

Asphalt
Paved

Roof

Shingle

Sewer

Public Sewer

Utilities

Cable Connected
Electricity Connected
Water Connected

Vegetation

Trees/Landscaped

View

Trees/Woods

WaterSource

Public

Rooms

Living Room
Kitchen
Dining Room
Bonus Room
Primary Bedroom
Primary Bathroom
Bedroom 2
Bedroom 3
Bathroom 2
Bathroom 3
Laundry
Balcony/Porch/Lanai

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Listed By:
HOME LAND REAL ESTATE INC
352-556-0909

Data Source: Stellar MLS

MLS#: W7886886

This property was listed on 6/27/2026 and last updated as of 9/19/2026 6:05:20 PM. OSI IDX updated the data from Stellar MLS on 11/7/2026 at 7:11 AM. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.