To schedule a showing of 65 Olive Street, Brooksville, Florida, Call David Shippey at 863-521-4517 TODAY!

65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601
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65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601 65 Olive Street Brooksville, FL 34601
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$619,000 | 3 beds | 3 full baths | N/A half baths | 1,961 sqft

$619,000 No Recent Price Change
65 Olive Street
Brooksville, FL 34601
  • 3Beds
  • 3.00Total Baths
  • 3 Full, 0 HalfBaths
  • 1,961SqFt
  • 1910Year Built
  • 0.48Acres
  • MLS# W7886886
  • Residential
  • SingleFamilyResidence
  • Active
Overview

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!!

Agriculture / Farm

Association Fees / Info

Community Features:  Sidewalks

Bathroom Info

Total Baths:  3.00

Fullbaths:  3

Building Info

Roof:  Shingle

Building Area Source:  PublicRecords

Buyer Compensation

Exterior Features

Patio:  RearPorch, Deck, FrontPorch, Patio

Exterior Features:  Lighting, RainGutters

Fees / Restrictions

Financial

Original Price:  $619,000

Garage / Parking

Parking Features:  CircularDriveway

Green / Env Info

Interior Features

Fireplace Desc:  WoodBurning

Fireplace:  Yes

Floors:  CeramicTile, Wood

Levels:  One

Laundry Features:  Inside, LaundryRoom

Interior Features:  CeilingFans, CrownMolding

Appliances:  Dishwasher, Microwave, Range, Refrigerator

Lot Info

Direction Remarks:  US 50 (Cortez Blvd) turns into W Jefferson St, left onto Ponce De Leon Blvd, right onto W Fort Dade Ave, left onto Howell Ave, right onto Olive St, house on left

Lot Size Units:  Acres

Lot Size Acres:  0.48

Lot Sqft:  20,978

Est Lotsize:  156x130

Vegetation:  PartiallyWooded

Lot Desc:  CornerLot, Landscaped

Misc

Other

Other Structures:  GuestHouse

Special Conditions:  None

Other Rooms Info

Property Info

Section:  22

Class Type:  SingleFamilyResidence

Property Sub Type:  SingleFamilyResidence

Construction Materials:  WoodFrame

Stories:  1

Total Stories:  2

Foundation:  ConcretePerimeter, PillarPostPier

Human Modified:  Yes

Room Info

Total Rooms:  12

Sqft Info

Sqft:  1,961

Bulding Area Sqft:  2,271

Living Area Units:  SquareFeet

Living Area Source:  PublicRecords

Tax Info

Tax Year:  2,025

Tax Lot:  1

Tax Legal Description:  MICKLERS ADDN TO BROOKSVILLE BLK 1 LOT 1 ORB 1240 PG 1390

Tax Block:  1

Tax Annual Amount:  4448.82

Tax Book Number:  3-1

Unit Info

Utilities / Hvac

Heating:  Central, Electric

Water Source:  Public

Sewer:  PublicSewer

Cool System:  CentralAir, CeilingFans

Cooling:  Yes

Heating:  Yes

Utilities:  CableConnected, ElectricityConnected, WaterConnected

Waterfront / Water

View:  Yes

View:  TreesWoods

Schools

Elem:  Brooksville Elementary

Middle:  D.s. Parrot Middle

High:  Hernando High

Directions

US 50 (Cortez Blvd) turns into W Jefferson St, left onto Ponce De Leon Blvd, right onto W Fort Dade Ave, left onto Howell Ave, right onto Olive St, house on left

This listing courtesy of Home Land Real Estate Inc 

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On davidshippey.com since Sat, Jun 27th 2026
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If you have any questions on 65 Olive Street, Brooksville, Florida, please call David Shippey at 863-521-4517.


MLS# W7886886 located at 65 Olive Street, Brooksville, Florida is brought to you by David Shippey REALTOR®

65 Olive Street, Brooksville, Florida has 3 Beds, 3 Full Bath, and 0 Half Bath.
The MLS Number for 65 Olive Street, Brooksville, Florida is W7886886.
The price for 65 Olive Street, Brooksville, Florida is $619,000.
The status of 65 Olive Street, Brooksville, Florida is Active.
The subdivision of 65 Olive Street, Brooksville, Florida is Micklers Add To Brksvl.
The home located at 65 Olive Street, Brooksville, Florida was built in 2026.