David Ramirez
$780,000$800,0005 bd3 ba2,194 sqft$356 /sqft$5,176 /mo all-in ↓

739 ROUGHBEARD ROAD, WINTER PARK, FL, 32792

Active77 days on marketListed May 4, 2026MLS #O6404545

Reduced $20KPrivate poolSingle Family ResidenceWINTER PARK PINES

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

Private poolFireplacePets allowed

Inside

FlooringTile
AppliancesDishwasher · Dryer · Microwave · Range · Refrigerator · Washer
InteriorBuilt-in Features · Ceiling Fan(s) · Crown Molding · Kitchen/Family Room Combo · Living Room/Dining Room Combo · Primary Bedroom Main Floor · Thermostat · Walk-In Closet(s)
LaundryInside · Laundry Room
CoolingCentral Air
HeatingCentral

Outside & construction

RoofShingle
ConstructionBlock · Concrete
FoundationSlab
FacesEast
ParkingDriveway · Garage Door Opener · On Street · Oversized · Workshop in Garage
ExteriorFrench Doors · Lighting · Sidewalk

Community & fees

Taxes (2025)$6,179/yr
PetsYes
CommunityGolf Carts OK · Golf · Sidewalks

Utilities & systems

UtilitiesCable Available · Electricity Connected · Natural Gas Connected · Sewer Connected · Water Connected
WaterPublic

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%

Principal & interest$4,209
PMI (est., until 20% equity)$293
Property tax — 2025 actual bill$515
Insurance (FL estimate)$160

The assumptions

Loan typeConventionalDown payment10% · $78,000Loan30-yr fixed at 6%Mortgage insuranceIncludedTaxesActual bill on recordInsuranceFlorida estimate

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

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Run your own numbers

Loan type

FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.

Down payment10% · $78,000
Interest rate6.00%
Loan term

Estimated payment

$5,176/mo

Principal & interest$4,209
PMI (est., until 20% equity)$293
Property taxes (actual bill)$515
Est. insurance$160

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.

List $780K
$508KedgeAI estimate $557,801 · range $530K$569K$811K

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

2
1
1
1 · this home
0
3
$298–315$315–331$331–348$348–364$364–381$381+

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

Map of 739 ROUGHBEARD ROAD inside its neighborhood boundary

Drive times from this address

Downtown Orlando17 min
Universal Orlando30 min
Orlando Int’l Airport (MCO)31 min
Walt Disney World50 min

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

ElementaryAloma Elementary★★★★★
HighWinter Park High★★★★
MiddleGlenridge Middle★★★★★

School assignments and ratings via edgeAI — always verify with the district.

The numbers that matter

The Winter Park market

Seller’s marketLeans seller4.9 months of inventoryBuyer’s 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

CurrentPrice reduced to $780,000 $20K
May 4, 2026Listed at $800,000 · 77 days on market since
1968Built · WINTER PARK PINES

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.

630 SAINT DUNSTAN WAYSold · Apr ’26

$710,000

630 SAINT DUNSTAN WAY · same community

5 bd · 2 ba · 2,240 sqft · $317/sqft · 5 DOM

715 ROUGHBEARD ROADSold · Aug ’25

$505,000

715 ROUGHBEARD ROAD · same community

4 bd · 2 ba · 2,250 sqft · $224/sqft · 56 DOM

2758 SANDWELL DRIVESold · 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.

David Ramirez

Your agent

David Ramirez

Real Estate Agent · CENTURY 21 Edge

Tours, negotiation, and every question about 739 ROUGHBEARD ROAD — start here.

Andrew Acosta

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.

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.

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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