27440 WINCHESTER DRIVE, BROOKSVILLE, FL, 34602
Active87 days on marketListed May 16, 2026MLS #TB8507066
About this home
27440 WINCHESTER DRIVE
With over 1,800 square feet of living space this 4-bedroom, 2-bathroom sits on a cleared 1-acre lot. This property has so much potential, so bring your ideas—it's ready for a transformation, and land is becoming rare, so grab this opportunity while you can and enjoy peaceful, country living away from the hustle and bustle of city life.
Facts & features
The home at a glance
4
Bedrooms
2
Bathrooms
1,827
Sqft
1 ac
Lot size
1980
Year built
One
Levels
$93
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$1,448 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$1,448/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
−55.2%
$/sqft vs N/A
$93 vs $288
Days on market
87 vs 54 typical
Where $93/sqft sits among the 236 homes for sale in N/A
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Brooksville
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Brooksville. See the full Brooksville guide →
BROOKSVILLE 34602 — neighborhood snapshot
Population
10,391
Median age
44.8
Median income
$72,054
Median home value
$241,300
Avg household
2.85
Households w/ children
1,051
For the school run
Hernando County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Brooksville market
$300K → $305K
Brooksville median sold, yr/yr
96.9%
Sale-to-list ratio (12 mo)
108 of 236
N/A have cut their price
Median sold price, Brooksville, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 43% below the BROOKSVILLE 34602 median. See the full Brooksville market guide →
Paper trail
This home's history
Reality check
What actually sold near 27440 WINCHESTER DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Dec ’25$375,000
12112 CR 727 · same community
3 bd · 2 ba · 1,800 sqft · $208/sqft · 8 DOM
Sold · Dec ’25$485,000
29655 SE 152ND (RAVENSWOOD) PLACE · same community
3 bd · 2 ba · 1,800 sqft · $269/sqft · 10 DOM
Sold · Dec ’25$388,750
2103 NW 142ND AVENUE · same community
3 bd · 2 ba · 1,728 sqft · $225/sqft · 0 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Frantreshia Miller
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 27440 WINCHESTER DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 27440 WINCHESTER DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Frantreshia's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
27440 WINCHESTER DRIVE FAQs
What would the monthly payment be for 27440 WINCHESTER DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $1,448/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 27440 WINCHESTER DRIVE?+
The most recent tax bill on record (2025) was $2,549. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Brooksville?+
At $170,000, this home is listed about 49% below the Brooksville median of $336,170. The market section on this page shows how the area is trending.
Which schools are assigned to 27440 WINCHESTER DRIVE?+
Eastside Elementary School (elementary), D. S. Parrott Middle School (middle) — Hernando County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of LPT REALTY, LLC · Duskie Smith. MLS #TB8507066.
IDX information is 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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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