
739 ROUGHBEARD ROAD, WINTER PARK, FL, 32792
Active77 days on marketListed May 4, 2026MLS #O6404545
About this home
739 ROUGHBEARD ROAD
Welcome to Winter Park Pines, one of Winter Park’s most desirable neighborhoods. This updated 5 bed, 3 bath pool home features a split floor plan, generous room sizes, and wood-plank tile flooring throughout most of the home. Inside, the formal living and dining rooms flow together and overlook the pool through French doors, while the large primary suite offers an en-suite bath, walk-in closet, and its own French doors to the huge covered, insulated patio. The light and bright kitchen includes a large breakfast bar, built-in pantry, and white cabinetry and appliances, and opens to the family room with a wood-burning fireplace and built-in desk. A separate bedroom wing provides four generous guest bedrooms and two full baths, including a Jack-and-Jill setup with walk-in closet, plus a true pool bath with access to the backyard and an inside utility/laundry room. Outdoor living is a highlight, with a fenced backyard, kidney-shaped pool, plenty of deck space, and ample yard beyond the pool so you’re not sacrificing green space. The large covered, insulated patio is ideal for year-round use. Major updates include a new roof (2022), new electric panel and updated outlets (2022), water lines re-piped to CPVC by a previous owner, new fence (2023), new dishwasher (2024), new water heater (2025), newer stove, washer, and dryer, new light fixtures throughout, and bathrooms updated with modern colors and fixtures. The exterior, garage, patio, and pool deck have all been freshly painted, giving the home a clean, move-in ready feel. This is a rare opportunity to own a well-maintained pool home in a prime Winter Park location—just steps from Cady Way Park and Trail and moments from Winter Park Pines Golf Course, with Winter Park High School and the nearby hospital campus within short distance and quick access to downtown Orlando, major highways, both airports, Disney, and Universal.
Facts & features
The home at a glance
5
Bedrooms
3
Bathrooms
2,194
Sqft
0.25 ac
Lot size
2
Garage
1968
Year built
One
Levels
$356
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.
$5,176 /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
$5,176/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
+39.8%
$/sqft vs WINTER PARK PINES
$356 vs $349
Days on market
77 vs 34 typical
Where $356/sqft sits among the 8 homes for sale in WINTER PARK PINES
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 Pines
Drive times from this address
Get to know Winter Park. See the full Winter Park guide →
Winter Park Pines — neighborhood snapshot
Population
2,446
Median age
38
Median income
$65,221
Median home value
$443,587
Avg household
2
Households w/ children
153
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)
3 of 8
WINTER PARK PINES have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 146% 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 739 ROUGHBEARD ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Apr ’26$710,000
630 SAINT DUNSTAN WAY · same community
5 bd · 2 ba · 2,240 sqft · $317/sqft · 5 DOM
Sold · Aug ’25$505,000
715 ROUGHBEARD ROAD · same community
4 bd · 2 ba · 2,250 sqft · $224/sqft · 56 DOM
Sold · Jan ’26$500,000
2758 SANDWELL DRIVE · same community
4 bd · 2 ba · 2,303 sqft · $217/sqft · 63 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 739 ROUGHBEARD ROAD — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 739 ROUGHBEARD ROAD — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
739 ROUGHBEARD ROAD FAQs
What would the monthly payment be for 739 ROUGHBEARD ROAD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $5,176/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 739 ROUGHBEARD ROAD?+
The most recent tax bill on record (2025) was $6,179. 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 739 ROUGHBEARD 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 $780,000, this home is listed about 24% 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 739 ROUGHBEARD ROAD?+
Aloma Elementary (elementary), Winter Park High (high), Glenridge 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
$780,000 runs 146% above the WINTER PARK 32792 median — but at 2,194 sqft it's also 20% larger than the typical Winter Park listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Time on market is leverage
77 days on market against a Winter Park median of 34 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Aloma Elementary, Winter Park High, Glenridge Middle — Winter Park High rates 4 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $800,000, now $780,000 — a $20K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of SERHANT · John Harbuck. MLS #O6404545.
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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