
855 BENCHWOOD DRIVE, WINTER SPRINGS, FL, 32708
Active11 days on marketListed Sep 29, 2026MLS #O6445288
About this home
855 BENCHWOOD DRIVE
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 855 Benchwood Drive in Winter Springs, a spacious 4-bedroom, 3-bathroom home situated in the established Oak Forest community. Offering approximately 2,268 square feet of living space, the home features an open floor plan designed to bring the main gathering areas together while providing flexibility for everyday living and entertaining. One of the four bedrooms is currently used as a home office, creating a dedicated workspace that can easily adapt to other needs. The interior offers generous living areas filled with natural light, along with a functional connection between the kitchen, dining, and main living spaces. The bedrooms provide plenty of room for family and guests, while three full bathrooms add convenience throughout the home. The flexible office can also serve as a guest room, hobby space, or additional bedroom as needed. Outside, the backyard is designed for enjoying the Florida lifestyle with a private in-ground pool and spa, surrounded by an expansive pool deck with plenty of space for lounging and entertaining. A covered patio provides a shaded area for outdoor dining and relaxing, while mature landscaping adds character to the outdoor setting. Public listing records also note the property sits on approximately 0.37 acre, providing additional yard space around the outdoor living areas. Located in Oak Forest, the home is close to neighborhood recreation, including Trotwood Park, as well as shopping, dining, and everyday conveniences throughout Winter Springs. The location also provides convenient access to Tuskawilla Road, SR 434, SR 417, and I-4, making surrounding Seminole County and Greater Orlando destinations easily accessible.
Facts & features
The home at a glance
4
Bedrooms
3
Bathrooms
2,268
Sqft
0.37 ac
Lot size
1984
Year built
One
Levels
$220
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 and the real association fee — not generic estimates.
$3,482 /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
$3,482/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
−10.6%
$/sqft vs Winter Springs actives
$220 vs $240
Days on market
11 vs 49 typical
Where $220/sqft sits among the 123 Winter Springs actives
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 Oak Forest
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Springs. See the full Winter Springs guide →
Oak Forest — neighborhood snapshot
Population
2,216
Median age
42
Median income
$122,576
Median home value
$426,653
Avg household
3
Households w/ children
260
For the school run
Seminole County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Springs market
$433K → $440K
Winter Springs median sold, yr/yr
97.8%
Sale-to-list ratio (12 mo)
71 of 123
Winter Springs actives have cut their price
Median sold price, Winter Springs, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 43% above the WINTER SPRINGS 32708 median. See the full Winter Springs market guide →
Paper trail
This home's history
Reality check
What actually sold near 855 BENCHWOOD DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’25$495,000
855 BENCHWOOD DRIVE · same community
4 bd · 3 ba · 2,268 sqft · $218/sqft · 48 DOM
Sold · Sep ’26$505,000
809 BIG BUCK CIRCLE · same community
4 bd · 2 ba · 2,250 sqft · $224/sqft · 51 DOM
Sold · Nov ’25$425,000
861 BIG BUCK CIRCLE · same community
3 bd · 2 ba · 1,831 sqft · $232/sqft · 46 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
Gianfranco Di Flumeri
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 855 BENCHWOOD DRIVE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 855 BENCHWOOD DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Gianfranco's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
855 BENCHWOOD DRIVE FAQs
What would the monthly payment be for 855 BENCHWOOD DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,482/mo — principal and interest, the actual property-tax bill, the $3/mo association fee 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.
How much are the HOA fees at 855 BENCHWOOD DRIVE?+
The association fee works out to $3 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 855 BENCHWOOD DRIVE?+
The most recent tax bill on record (2025) was $1,924. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 855 BENCHWOOD DRIVE?+
The listing reports pets: Breed Restrictions, Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Springs?+
At $499,000, this home is listed about 27% above the Winter Springs median of $392,400. The market section on this page shows how the area is trending.
Which schools are assigned to 855 BENCHWOOD DRIVE?+
Indian Trails Middle School (middle), Keeth Elementary School (elementary), Winter Springs High School (high) — Seminole County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$499,000 runs 43% above the WINTER SPRINGS 32708 median — but at 2,268 sqft it's also 35% larger than the typical Winter Springs listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Strong assigned schools
Indian Trails Middle School, Keeth Elementary School, Winter Springs High School — Indian Trails Middle School rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS REALTY AT THE PARKS · Thomas Nickley, Jr. MLS #O6445288.
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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