2572 FIFESHIRE DRIVE, WINTER PARK, FL, 32792
Active2 days on marketListed Sep 18, 2026MLS #O6442325
Come see it
Upcoming open house
Sun, Sep 20
1:00 PM – 3:00 PM
About this home
2572 FIFESHIRE DRIVE
Welcome to this warm and inviting home in the desirable Brookshire Heights neighborhood, ideally positioned on a corner lot along a beautiful street in a sought-after community. Offering more than 2,500 square feet of living space, this spacious residence features four bedrooms and two-and-a-half baths, with an open, comfortable layout designed for both everyday living and entertaining. The home has been thoughtfully updated and maintained over the years, blending timeless character with modern conveniences. The kitchen was beautifully remodeled in 2021 with new cabinetry, appliances, flooring, and countertops, while the family room was enhanced with additional air-conditioning ducts and vents for added comfort. The second full bath was also remodeled in 2021, and the downstairs powder room received a stylish update in 2025.Significant improvements include new wood flooring downstairs and refinished and stained upstairs floors in 2019, a new HVAC system with an additional upstairs unit and complete ductwork replacement in 2020, and a customized primary closet in 2022. The primary suite continues to impress with a new porch door and a private balcony railing added in 2026. A new water heater was installed in 2023, while the main sewer line exiting the home was replaced in 2024.Outdoor living has been equally well considered, with a screened porch enclosure, a covered side patio, new fencing, and refreshed landscaping creating inviting spaces to relax and entertain. Beyond the home itself, the location is exceptional—conveniently situated in a wonderful community with Cady Way pool and Cady Way trail which spans 7.2 miles and connects to the Seminole trail for bike riding, running and walking. Highly regarded schools and easy access to the area’s everyday amenities. With its generous living spaces, extensive updates, inviting outdoor areas, and prime corner-lot setting, this Brookshire Heights home offers an exceptional opportunity to enjoy a beautifully cared-for residence in a highly desirable location.
Facts & features
The home at a glance
4
Bedrooms
2.5
Bathrooms
2,578
Sqft
0.21 ac
Lot size
2
Garage
1962
Year built
Two
Levels
$359
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.
$5,944 /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
$5,944/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
−13.7%
$/sqft vs Winter Park actives
$359 vs $349
Days on market
2 vs 43 typical
Where $359/sqft sits among the 350 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 Brookshire Heights
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Brookshire Heights — neighborhood snapshot
Population
784
Median age
42
Median income
$131,420
Median home value
$478,000
Avg household
3
Households w/ children
119
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)
158 of 350
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 208% 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 2572 FIFESHIRE DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’26$630,000
2504 FORFARSHIRE DRIVE · same community
3 bd · 2 ba · 1,915 sqft · $329/sqft · 5 DOM
Sold · Sep ’25$1,396,500
2781 STANFIELD AVENUE
3 bd · 2.5 ba · 2,550 sqft · $548/sqft · 52 DOM
Sold · May ’26$1,225,000
3923 HAWS LANE
4 bd · 2.5 ba · 2,549 sqft · $481/sqft · 0 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
Anealya Hammad
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 2572 FIFESHIRE DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2572 FIFESHIRE DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Anealya's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
2572 FIFESHIRE DRIVE FAQs
What would the monthly payment be for 2572 FIFESHIRE DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $5,944/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 2572 FIFESHIRE DRIVE?+
The most recent tax bill on record (2025) was $5,351. 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 $925,000, this home is listed about 61% above the Winter Park median of $575,000. The market section on this page shows how the area is trending.
Which schools are assigned to 2572 FIFESHIRE DRIVE?+
Brookshire 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
Three things that matter here
01Positioned at the premium end
$925,000 runs 208% above the WINTER PARK 32792 median — but at 2,578 sqft it's also 47% larger than the typical Winter Park listing.
02Fresh on the market
Only 2 days on market in a Winter Park market that averages 43 — if it fits, move quickly.
03Strong assigned schools
Brookshire Elementary, Winter Park High, Glenridge Middle — 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 · MaryAnne Branner. MLS #O6442325.
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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