
4469 OLD BEAR RUN, WINTER PARK, FL, 32792
Active164 days on marketListed Feb 9, 2026MLS #O6375415
About this home
4469 OLD BEAR RUN
Private, gated lakefront living on Bear Gully Lake one of Winter Park’s most desirable spring-fed ski lakes. Set on an expansive 137-acre body of water, this custom residence offers a rare combination of privacy, scale, and true Florida waterfront lifestyle. A circular driveway behind a private gate welcomes you to a thoughtfully renovated home designed to capture sweeping lake views. Bear Gully Lake is spring-fed and open to water vehicles, making it ideal for boating, water skiing, wakeboarding, tubing, fishing, and year-round enjoyment. The lakefront experience is exceptional, featuring a fully equipped dock with power, covered boat lift, and sun deck, perfectly positioned for enjoying stunning sunsets. Outdoor living is a highlight of the property. The expansive lanai and pool area overlook the lake and are ideal for entertaining, complete with a renovated summer kitchen featuring a grill, sink, mini refrigerator, and granite countertops. The oversized backyard provides ample space for gatherings, recreation, and pets. Inside, the home opens to a dramatic great room with vaulted ceilings, a striking stacked-stone feature wall with custom built-ins, and large sliding glass doors that fully retract to create seamless indoor-outdoor living. The space was reimagined during extensive renovations to maximize natural light and lake views. The chef’s kitchen, redesigned by award-winning designer Sandra Agurto of CCI, features all-wood cabinetry, quartz countertops, contemporary backsplash, oversized island with beverage and wine refrigerators, induction cooktop, convection ovens, and a separate full refrigerator and freezer, with abundant custom storage throughout. The primary suite is privately located in its own wing and offers serene lake views, high ceilings, and a spa-style en-suite bath renovated in 2022 with soaking tub, walk-in shower, expansive custom vanity, upgraded lighting, and private water closet with bidet. A large walk-in closet with custom built-ins completes the suite. All bedrooms feature their own bathrooms and walk-in closets, providing exceptional privacy and flexibility, with three full en-suite bedrooms ideal for guests or multigenerational living. Additional flexible spaces include a gym or bonus room suitable for formal living, dining, or a game room. Recent upgrades include a new roof (2018), new hot water heater (2024), fully fenced yard, Russound sound system, updated security system, new pool deck pavers, and a rebuilt dock with Trex decking and updated boat lift components. The home is part of a lake association with no mandatory dues, providing community updates and seasonal events such as the holiday boat parade. Conveniently located near SR-417, UCF, downtown Winter Park, and Trinity Prep, this is a rare opportunity to own a true spring-fed lakefront home on one of Winter Park’s most coveted lakes.
Facts & features
The home at a glance
5
Bedrooms
4.5
Bathrooms
4,288
Sqft
0.74 ac
Lot size
2
Garage
1978
Year built
One
Levels
$420
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.
$11,440 /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
$11,440/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
+78.2%
$/sqft vs Winter Park actives
$420 vs $345
Days on market
164 vs 34 typical
Where $420/sqft sits among the 313 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 Winter Park
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
WINTER PARK 32792 — neighborhood snapshot
Population
52,794
Median age
34.7
Median income
$66,176
Median home value
$343,500
Avg household
2.34
Households w/ children
5,372
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Park market
$473K → $500K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
143 of 313
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 467% 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 4469 OLD BEAR RUN
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’25$800,000
4702 SHORECREST DRIVE
4 bd · 3.5 ba · 4,202 sqft · $190/sqft · 26 DOM
Sold · Nov ’25$910,000
1319 HEAVENLY COVE
4 bd · 3.5 ba · 4,088 sqft · $223/sqft · 139 DOM
Sold · Jul ’25$1,180,000
4052 GILDER ROSE PLACE
4 bd · 4 ba · 4,015 sqft · $294/sqft · 37 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
Kat Bonelli
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 4469 OLD BEAR RUN — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 4469 OLD BEAR RUN — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Kat's phone and CRM.
Straight answers
4469 OLD BEAR RUN FAQs
What would the monthly payment be for 4469 OLD BEAR RUN?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $11,440/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 4469 OLD BEAR RUN?+
The most recent tax bill on record (2024) was $10,710. 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 Winter Park?+
At $1,799,999, this home is listed about 187% above the Winter Park median of $627,000. The market section on this page shows how the area is trending.
Which schools are assigned to 4469 OLD BEAR RUN?+
Lakemont Elementary (elementary), Winter Park High (high), Maitland Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Positioned at the premium end
$1,799,999 runs 467% above the WINTER PARK 32792 median — but at 4,288 sqft it's also nearly twice the size of the typical Winter Park listing.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Time on market is leverage
164 days on market against a Winter Park median of 34 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Lakemont Elementary, Winter Park High, Maitland Middle — Winter Park High rates 4 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $1,950,000, now $1,799,999 — a $150K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of LPT REALTY, LLC · Keigan Lewis. MLS #O6375415.
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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