65 Olive Street, Brooksville, FL 34601

• 3 beds |
• 3 baths |
• 1,961 sqft

Property Description

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 the 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!!

Listing Status:

Active

Date Added:

June 27, 2026

Data Last Updated:

July 5, 2026 at 11:40PM

Listing Office:

Home-Land Real Estate Inc : 352-556-0909

MLS ID:

2259962

Interior

• General: Ceiling Fan(s)Kitchen IslandPantryPrimary DownstairsPrimary Bathroom - Shower No Tub
• Appliances: DishwasherElectric RangeMicrowaveRefrigerator
• Laundry: Lower LevelIn Unit
• Flooring: TileWood
• A/C: Central Air
• Heating: CentralElectric
• Fireplace: Wood BurningFireplaceFireplaces: 1

Exterior

• General: GazeboShed(s)
• Style: Historic
• Other Structures: GazeboShed(s)Front PorchRear PorchCovered
• Parking: Circular Driveway

Construction

• Roofing: Shingle
• General: Wood Siding1

Location

• Road/Access: AsphaltPaved
• Originating MLS: Hernando County Association of REALTORS®
• County: Hernando

Lot

• Zoning: CityMicklers Addn To Brooksville Blk 1 Lot 1 Orb 1240 Pg 1390 ** Continued **R22 222 19 2710 0010 0010
• View: Trees/Woods
• Current Use: RecreationalSingle Family

Utilities

• Utilities: Cable ConnectedElectricity ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Hernando County Association of REALTORS®