844 OAKLAND PARK BOULEVARD, WINTER GARDEN, FL, 34787
Active35 days on marketListed Jul 1, 2026MLS #O6419976
About this home
844 OAKLAND PARK BOULEVARD
Virtually Staged. More than a home, this is a lifestyle. Perfectly positioned in the highly sought-after Oakland Park community, this exceptional residence combines timeless design, generous living spaces, and effortless indoor-outdoor living just a golf cart ride from the heart of downtown Winter Garden. With 5 large bedrooms plus a den spread across over 3,500 square feet, the home provides ample space for everyday living and entertaining. Upon arrival, a welcoming front porch sets the tone, offering the perfect place to enjoy a quiet morning coffee or unwind with a glass of wine at sunset. Inside, elegant French doors open to a private home office, while engineered hardwood flooring flows throughout the main living areas. The open-concept floor plan is filled with natural light, creating an inviting space for both everyday living and entertaining. At the heart of the home, the spacious kitchen overlooks the living area and seamlessly connects to the expansive screened lanai through double French doors. The first-floor primary suite is a private retreat, highlighted by a tray ceiling and a spa-inspired bath featuring dual vanities, a soaking tub, a separate walk-in shower, and an oversized walk-in closet. A secondary bedroom and full bath on the main level provide ideal accommodations for guests or multigenerational living. Upstairs, a spacious loft offers endless possibilities as a media room, game room, or additional gathering space. Three generously sized secondary bedrooms—each with its own walk-in closet—along with two full bathrooms provide comfort and privacy for family and guests alike. Step outside to one of the home's most impressive features: an expansive screened lanai overlooking a fully fenced backyard with ample room to design the pool of your dreams. Completing the property is a coveted three-car garage, offering abundant space for vehicles, storage, and recreation. Residents of Oakland Park enjoy a picturesque, tree-lined community known for its welcoming atmosphere, resort-style amenities, seasonal community events and unmatched location. Just minutes from the award-winning shops, restaurants, farmers market, and West Orange Trail in historic downtown Winter Garden, this home offers the perfect balance of luxury, convenience, and the quintessential Central Florida lifestyle.
Facts & features
The home at a glance
5
Bedrooms
4
Bathrooms
3,525
Sqft
0.21 ac
Lot size
3
Garage
2012
Year built
Two
Levels
$339
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.
$8,438 /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
$8,438/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
−2.9%
$/sqft vs Winter Garden actives
$339 vs $261
Days on market
35 vs 37 typical
Where $339/sqft sits among the 400 Winter Garden 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 Garden
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
WINTER GARDEN 34787 — neighborhood snapshot
Population
93,064
Median age
37.4
Median income
$114,988
Median home value
$475,000
Avg household
3.02
Households w/ children
13,499
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 Garden market
$585K → $611K
Winter Garden median sold, yr/yr
97.6%
Sale-to-list ratio (12 mo)
171 of 400
Winter Garden actives have cut their price
Median sold price, Winter Garden, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 125% above the WINTER GARDEN 34787 median. See the full Winter Garden market guide →
Paper trail
This home's history
Reality check
What actually sold near 844 OAKLAND PARK BOULEVARD
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$1,335,000
15326 JOHNS LAKE POINTE BOULEVARD
4 bd · 3.5 ba · 3,495 sqft · $382/sqft · 6 DOM
Sold · May ’26$950,000
15226 SUNSET OVERLOOK CIRCLE
5 bd · 4 ba · 3,556 sqft · $267/sqft · 35 DOM
Sold · Apr ’26$850,000
501 E OAKLAND AVENUE
4 bd · 3.5 ba · 3,448 sqft · $247/sqft · 89 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 844 OAKLAND PARK BOULEVARD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 844 OAKLAND PARK BOULEVARD — 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
844 OAKLAND PARK BOULEVARD FAQs
What would the monthly payment be for 844 OAKLAND PARK BOULEVARD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $8,438/mo — principal and interest, the actual property-tax bill, the $208/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 844 OAKLAND PARK BOULEVARD?+
The association fee works out to $208 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 844 OAKLAND PARK BOULEVARD?+
The most recent tax bill on record (2025) was $14,087. 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 844 OAKLAND PARK BOULEVARD?+
The listing reports pets: Cats OK, Dogs OK. 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 Garden?+
At $1,195,000, this home is listed about 104% above the Winter Garden median of $587,000. The market section on this page shows how the area is trending.
Which schools are assigned to 844 OAKLAND PARK BOULEVARD?+
Sunridge Elementary (elementary), Sunridge Middle (middle), West Orange High (high) — Orange 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
$1,195,000 runs 125% above the WINTER GARDEN 34787 median — but at 3,525 sqft it's also 64% larger than the typical Winter Garden listing.
02Strong assigned schools
Sunridge Elementary, Sunridge Middle, West Orange High — Sunridge Middle rates 4 of 5. Always verify assignments with the district.
03The price has already moved
Listed at $1,225,000, now $1,195,000 — a $30K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of COLDWELL BANKER REALTY · Sophia Gordon. MLS #O6419976.
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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