1421 CHESTNUT AVENUE, WINTER PARK, FL, 32789
Active2 days on marketListed Sep 18, 2026MLS #O6442995
About this home
1421 CHESTNUT AVENUE
Prime Winter Park builder and luxury custom home opportunity with rare dual access! Nestled in this Winter Park enclave just one block from the Via Streets, this location offers a massive competitive advantage and features a dedicated rear easement providing direct vehicle or construction access to the adjacent side street (Sunset). Whether you are an investor looking for a high-end project or designing your private sanctuary, this unique dual-access point is a designer’s dream—opening up incredible architectural flexibility, private rear-loading/garage options, or seamless construction staging. The property boasts an unobstructed view of the serene park setting at the intersection of Chestnut and Sunset, providing a picturesque backdrop for custom luxury home architecture. Surrounding properties are rapidly redeveloping into spectacular modern estates. Bring your custom builder and your vision to claim one of Winter Park's unique footprints. Property is being sold As-Is with value in the land. One car garage at rear of property with access thru deeded easement. Shed next to garage.
Facts & features
The home at a glance
0.17 ac
Lot size
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.
$4,645 /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
$4,645/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.
Where it sits
Inside Lake Knowles Terrace
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Lake Knowles Terrace — neighborhood snapshot
Population
1,017
Median age
49
Median income
$193,750
Median home value
$808,200
Avg household
3
Households w/ children
126
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)
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 8% below the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 1421 CHESTNUT 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$530,000
1409 SUNSET DRIVE · same community
2 bd · 1.5 ba · 1,107 sqft · $479/sqft · 4 DOM
Sold · Dec ’25$1,095,000
1450 CHESTNUT AVENUE · same community
3 bd · 3.5 ba · 1,942 sqft · $564/sqft · 49 DOM
Sold · Jul ’26$1,450,000
1660 WALNUT AVENUE · same community
4 bd · 3.5 ba · 2,249 sqft · $645/sqft · 43 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
Gianfranco Di Flumeri
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 1421 CHESTNUT AVENUE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1421 CHESTNUT AVENUE — before you fall in love.
See it in person
Schedule a tour
Live availability from Gianfranco's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
1421 CHESTNUT AVENUE FAQs
What would the monthly payment be for 1421 CHESTNUT AVENUE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,645/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 1421 CHESTNUT AVENUE?+
The most recent tax bill on record (2025) was $1,882. 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 $750,000, this home is listed about 30% 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 1421 CHESTNUT 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
01Under the WINTER PARK 32789 market on paper
$750,000 is 8% below the WINTER PARK 32789 median of $815,000.
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
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 CHARLES RUTENBERG REALTY ORLANDO · Barry Sanford PA. MLS #O6442995.
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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