4260 BEAR GULLY ROAD, WINTER PARK, FL, 32792
Active21 days on marketListed Sep 21, 2026MLS #O6443414
About this home
4260 BEAR GULLY ROAD
RENOVATED 4 BED / 3.5 BATH TWO-STORY | GOURMET KITCHEN | LUXURY VINYL FLOORING | ROOF 2018 | FENCED BACKYARD | CLOSE TO ALOMA AVE & SR 417 Welcome to 4260 Bear Gully Road, a beautifully updated, move-in-ready home for anyone who wants a truly nice place to live. The heart of the home is the gourmet kitchen, fully remodeled just two years ago with upscale cabinetry and modern appliances, perfect for everyday meals and entertaining. Luxury vinyl flooring gives the home a clean, modern look that is easy to maintain. With four bedrooms and four full bathrooms across two stories, everyone has room and privacy, whether for family, guests or a home office. Enjoy the screened lanai and the fenced backyard, ready for pets, play and weekend get-togethers. Added peace of mind: roof replaced in 2018, concrete block and stucco construction, and Flood Zone X. Location is a major plus. You're near the Publix-anchored shopping, dining and services along Aloma Avenue, AdventHealth Winter Park, and the Cross Seminole Trail, with easy access to SR 417 (Central Florida GreeneWay). Winter Park Village and the boutiques and restaurants of Park Avenue are a short drive away. Served by Seminole County Public Schools: Eastbrook Elementary, Tuskawilla Middle and Lake Howell High (buyer to verify). Schedule your showing today!
Facts & features
The home at a glance
4
Bedrooms
3.5
Bathrooms
2,322
Sqft
0.57 ac
Lot size
2
Garage
2005
Year built
Two
Levels
$258
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.
$3,944 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
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
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$3,944/mo
Includes estimated PMI — it drops off once you reach 20% equity. 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
+1.5%
$/sqft vs Winter Park actives
$258 vs $343
Days on market
21 vs 58 typical
Where $258/sqft sits among the 339 Winter Park 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 Bear Gully Forest
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Bear Gully Forest — neighborhood snapshot
Population
1,054
Median age
31
Median income
$56,733
Avg household
3
Households w/ children
201
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 Park market
$470K → $530K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
162 of 339
Winter Park actives have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 64% above the WINTER PARK 32792 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 4260 BEAR GULLY ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jul ’26$465,000
4190 BEAR GULLY ROAD · same community
4 bd · 2.5 ba · 2,058 sqft · $226/sqft · 166 DOM
Sold · Apr ’26$549,000
4033 YACHT COURT
3 bd · 2 ba · 2,268 sqft · $242/sqft · 13 DOM
Sold · Jul ’26$599,000
8617 AMBER OAK COURT
4 bd · 2 ba · 2,253 sqft · $266/sqft · 5 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
Anthony Richardson
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 4260 BEAR GULLY ROAD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 4260 BEAR GULLY ROAD — before you fall in love.
See it in person
Schedule a tour
Live availability from Anthony's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
4260 BEAR GULLY ROAD FAQs
What would the monthly payment be for 4260 BEAR GULLY ROAD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $3,944/mo — principal and interest, the actual property-tax bill, the $54/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 4260 BEAR GULLY ROAD?+
The association fee works out to $54 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 4260 BEAR GULLY ROAD?+
The most recent tax bill on record (2025) was $3,283. 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 4260 BEAR GULLY ROAD?+
The listing reports pets: 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 Park?+
At $599,000, this home is priced right at the Winter Park median.
Which schools are assigned to 4260 BEAR GULLY ROAD?+
Tuskawilla Middle School (middle), Lake Howell High School (high), Eastbrook Elementary School (elementary) — Seminole County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of WRA BUSINESS & REAL ESTATE · Alexandre Zapparoli LLC. MLS #O6443414.
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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