
1597 OAKHURST AVENUE, WINTER PARK, FL, 32789
Active2 days on marketListed Aug 26, 2026MLS #O6436291
About this home
1597 OAKHURST AVENUE
A DISTINCTIVE WINTER PARK RESIDENCE IN AN EXCEPTIONAL LOCATION. Set along a quiet brick street in one of Winter Park’s most established and desirable residential enclaves, this substantial custom home offers more than 4,400 square feet of living space in a setting surrounded by some of the area’s most architecturally notable residences. Originally built in 2015, the home has been thoughtfully and significantly enhanced by its current owners. The main living level was reconfigured to create a more open and functional flow, while the kitchen was completely renovated and wide-plank oak flooring was installed throughout both levels. The result is an interior that feels current and refined while remaining entirely appropriate to the home’s distinctive Winter Park character. Both HVAC systems have also been recently replaced. One of the residence’s most compelling qualities is the transition from its dramatic, old-world exterior presence through intimate courtyard and covered patio spaces into a beautifully updated interior. Soaring vaulted ceilings, exposed beams and generous room proportions create a sense of scale and architectural character rarely found in newer construction. The floor plan is equally impressive, with two bedroom suites on the main level, including a private primary retreat, while the second floor offers an oversized family-room loft, additional bedrooms and baths, and an abundance of storage. Indoor and outdoor living come together particularly well at the rear of the home, where the main living spaces open naturally to a large covered terrace and pool. The result is a true extension of the interior living environment and an ideal setting for year-round entertaining, relaxed gatherings and the Florida lifestyle Winter Park is known for. Rarely does a residence combine this degree of scale, architectural individuality, recent renovation and location so successfully. Zoned for top-rated public schools and near elite private schools, with easy access to Phelps Park, YMCA, ICC, WPRC and Park Avenue shops and restaurants!A sophisticated and highly livable custom home in one of Central Florida’s most coveted communities.
Facts & features
The home at a glance
5
Bedrooms
4.5
Bathrooms
4,410
Sqft
0.27 ac
Lot size
2
Garage
2015
Year built
Two
Levels
$612
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.
$17,435 /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
$17,435/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
+10.1%
$/sqft vs Winter Park actives
$612 vs $345
Days on market
2 vs 43 typical
Where $612/sqft sits among the 333 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 Comstock 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 →
Comstock Park — neighborhood snapshot
Population
551
Median age
53
Median income
$194,062
Median home value
$986,135
Avg household
2
Households w/ children
43%
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)
151 of 333
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 286% 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 1597 OAKHURST AVENUE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’25$3,200,000
1610 OAKHURST AVENUE · same community
5 bd · 6 ba · 4,255 sqft · $752/sqft · 3 DOM
Sold · Jul ’26$2,650,000
1630 LASBURY AVENUE · same community
5 bd · 4 ba · 4,917 sqft · $539/sqft · 49 DOM
Sold · May ’26$1,675,000
1560 WOODLAND AVENUE · same community
5 bd · 4.5 ba · 3,851 sqft · $435/sqft · 16 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
Julian Rivera
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 1597 OAKHURST AVENUE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1597 OAKHURST AVENUE — before you fall in love.
See it in person
Schedule a tour
Live availability from Julian's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
1597 OAKHURST AVENUE FAQs
What would the monthly payment be for 1597 OAKHURST AVENUE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $17,435/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 1597 OAKHURST AVENUE?+
The most recent tax bill on record (2025) was $20,385. 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 1597 OAKHURST 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 $2,699,000, this home is listed about 369% 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 1597 OAKHURST AVENUE?+
Lakemont Elementary (elementary), Winter Park High (high), Maitland Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$2,699,000 runs 286% above the WINTER PARK 32789 median — but at 4,410 sqft it's also nearly 3 times the size of 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.
03Fresh on the market
Only 2 days on market in a Winter Park market that averages 43 — if it fits, move quickly.
04Strong assigned schools
Lakemont Elementary, Winter Park High, Maitland Middle — Winter Park High rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS REALTY AT THE PARKS · Robert Kurzreiter PA. MLS #O6436291.
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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