Single Family Residence at 65 OLIVE ST, BROOKSVILLE
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71 photos

$599,000

65 OLIVE ST
BROOKSVILLE, FL 34601
Listed by Kimberly Pye, PA · HOME LAND REAL ESTATE INC
Bedrooms
3
Bathrooms
3
Living area
1,961 sqft
Year built
1910

About this home

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!!

Highlights

Fireplace

Property details

MLS
Stellar MLS
MLS #
MFRW7886886
Property type
Single Family Residence
Subdivision
MICKLERS ADD TO BRKSVL
Status
Active
Days on market
84
On market date
June 27, 2026
Stories
N/A
Total bathrooms
3
Garage spaces
N/A
Parking spaces
N/A
Lot size
0.48 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
BROOKSVILLE ELEMENTARY SCHOOL
0.56 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
659
Student:teacher ratio
16.1:1
District
HERNANDO
MiddleCharter
BROOKSVILLE ENGINEERING SCIENCE AND TECHNOLOGY (B.E.S.T.) A
1.08 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
72
Student:teacher ratio
12.0:1
District
HERNANDO
High
HERNANDO HIGH SCHOOL
0.42 mi away · Grades 6-12
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,189
Student:teacher ratio
19.8:1
District
HERNANDO

Walkability

Blended score for BROOKSVILLE's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

67
Walkable
out of 100
EPA National Walkability Index
13.0 / 20 -- Above average walkable
Google Places amenity density
70 / 100
Restaurants & cafes20
Grocery stores0
Parks4
Schools10
Transit stops8
Pharmacies0

Market position

How this listing compares to current activity in BROOKSVILLE, from live MLS data.

On the market 84 days -- 30 fewer days than BROOKSVILLE's current average of 114 days.
For reference, the median list price across 926 active listings in BROOKSVILLE right now is $303,450.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Adjust tax / insurance estimates
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/mo
Est. monthly payment
$3,757/mo
$119,800 down
$479,200 loan
Principal & interest$3,108
Property tax (est.)$499
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated September 19, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.