922 N PENNSYLVANIA AVENUE, WINTER PARK, FL, 32789
Active26 days on marketListed Jul 14, 2026MLS #O6424685
About this home
922 N PENNSYLVANIA AVENUE
Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.
Facts & features
The home at a glance
4
Bedrooms
4
Bathrooms
3,440
Sqft
0.17 ac
Lot size
2
Garage
2001
Year built
Two
Levels
$580
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.
$12,563 /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
$12,563/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
+67.9%
$/sqft vs Winter Park actives
$580 vs $343
Days on market
26 vs 44 typical
Where $580/sqft sits among the 318 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 32789 — neighborhood snapshot
Population
26,884
Median age
44.4
Median income
$100,213
Median home value
$695,000
Avg household
2.13
Households w/ children
2,125
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
$470K → $512K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
145 of 318
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 157% above the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 922 N PENNSYLVANIA AVENUE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jan ’26$1,707,880
1417 MILLER AVENUE
5 bd · 4 ba · 3,312 sqft · $516/sqft · 183 DOM
Sold · Sep ’25$1,595,000
1733 HARMON AVENUE
5 bd · 4.5 ba · 3,267 sqft · $488/sqft · 27 DOM
Sold · Apr ’26$1,390,000
525 LAKEVIEW AVENUE
4 bd · 4.5 ba · 3,253 sqft · $427/sqft · 254 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 922 N PENNSYLVANIA AVENUE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 922 N PENNSYLVANIA AVENUE — 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
922 N PENNSYLVANIA AVENUE FAQs
What would the monthly payment be for 922 N PENNSYLVANIA AVENUE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $12,563/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 922 N PENNSYLVANIA AVENUE?+
The most recent tax bill on record (2025) was $10,684. 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 922 N PENNSYLVANIA AVENUE?+
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 $1,995,000, this home is listed about 233% above the Winter Park median of $599,000. The market section on this page shows how the area is trending.
Which schools are assigned to 922 N PENNSYLVANIA AVENUE?+
Lakemont Elementary (elementary), Maitland Middle (middle), Winter Park 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
$1,995,000 runs 157% above the WINTER PARK 32789 median — but at 3,440 sqft it's also nearly twice the size of the typical Winter Park listing.
02Golf Course views
The golf course view is part of what you're buying — views hold value independently of the structure.
03Strong assigned schools
Lakemont Elementary, Maitland Middle, Winter Park High — Winter Park High rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of PREMIER SOTHEBY'S INTL. REALTY · Mick Night. MLS #O6424685.
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.
Never miss a listing
New Winter Park homes, in your inbox
Like 922 N PENNSYLVANIA AVENUE but not quite? A daily digest of every new listing in Winter Park — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask David to ping you on any price or status change →