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$599,000

65 Olive St

Brooksville, FL
Active
3
Bedrooms
3
Bathrooms
2,271
Square Feet
0.48
Lot Size (acres)
1910
Year Built
99
Days On Market

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!!

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Listing Information

Listing Updated
15 days ago
Listed By
Kimberly Pye, PA, 3522791150 · HOME LAND REAL ESTATE INC, 3525560909
MLS#
W7886886
Source
Stellar MLS
Status
Active

Facts & Features

Location

Community Information

Address
65 Olive St, Brooksville, FL 34601
City
Brooksville
County
Hernando
Neighborhood
MICKLERS ADD TO BRKSVL
Zip Code
34601

Architecture

Bedrooms
3
Bathrooms
3
Stories
2
Year Built
1910
Construction Materials
Frame
Building Area
2,271 sq. ft.
Foundation
Pillar/Post/Pier, Concrete Perimeter
Roof
Shingle
Levels
One
Garage Spaces
0
Parking Features
Circular Driveway

Features & Amenities

Interior Features
Crown Molding
Appliances
Dishwasher, Microwave, Refrigerator, Range
Flooring
Ceramic Tile, Wood
Exterior Features
Lighting, Rain Gutters
Patio and Porch
Patio, Deck, Front Porch, Rear Porch
Cooling
Central Air
Heating
Electric, Central

Property Features

Lot Size
0.48 Acres
Lot Features
Corner Lot
View
Trees/Woods
Water
Public
Sewer
Public Sewer
Utilities
Cable Available, Cable Connected, Electricity Connected, Water Connected

Square Footage

Total
1,961 sq. ft.

Tax & Financial Information

List Price
$599,000
Annual Taxes
$4,448

Schools

53/100
Brooksville Elementary School
Elementary · Grades PK–05 · 0.6 mi
Assigned school for this home
City
Brooksville
Students
660
Parent reviews
2.0★ avg · 2 reviews
Student body
70% White · 13% Black · 10% Hispanic / Latino
Free/reduced lunch
78%
Phone
(352) 797-7014
54/100
Hernando High School
High · Grades 06–12 · 0.4 mi
Assigned school for this home
City
Brooksville
Students
1,299
Student body
61% White · 19% Hispanic / Latino · 14% Black
Free/reduced lunch
52%
Phone
(352) 797-7015
100/100
Brooksville Engineering Science And Technology (B.E.S.T.)
Middle · Grades 06–08 · 1.1 mi
City
Brooksville
Students
125
Student body
56% White · 25% Black · 14% Hispanic / Latino
Free/reduced lunch
57%
Phone
(352) 544-2373
55/100
Hernando Eschool Virtual Franchise
7th & Above · Grades 01–12 · 0.8 mi
City
Brooksville
Students
53
Student body
72% White · 21% Hispanic / Latino · 8% Two or More Races
Free/reduced lunch
6%
Phone
(352) 797-7013
54/100
Hernando Virtual Instruction
7th & Above · Grades KG–12 · 0.8 mi
City
Brooksville
Students
9
Student body
56% White · 22% Hispanic / Latino · 22% Two or More Races
Free/reduced lunch
33%
Phone
(352) 797-7072
54/100
D. S. Parrott Middle School
Middle · Grades 06–08 · 2.9 mi
City
Brooksville
Students
729
Student body
61% White · 19% Hispanic / Latino · 13% Black
Free/reduced lunch
66%
Phone
(352) 797-7075
52/100
Hernando Virtual Instruction (Course Offerings)
7th & Above · Grades KG–12 · 0.8 mi
City
Brooksville
Students
21
Student body
71% White · 14% Black · 10% Hispanic / Latino
Free/reduced lunch
48%
Phone
(352) 797-7013
51/100
Hernando High School/Adult Education
Grades AE–AE · 0.4 mi
City
Brooksville
Phone
(352) 797-7019

School ratings are provided for informational purposes only and are subject to change. Attendance boundaries are for reference only — contact the school or district directly to verify enrollment eligibility.

Historical Data

Price History

DateEventPrice
09/17/2026Price change$599,000
06/27/2026Listed for sale$619,000

Listed by Kimberly Pye, PA · HOME LAND REAL ESTATE INC · 3525560909

Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, Stellar MLS. All rights reserved.

Last Updated: September 19, 2026 at 6:07 PM | Source: Stellar MLS | MLS#: W7886886

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