Video tour
$10,000 Closing Credit¹
#O6270191, Kim Wood, Listing Office: COLDWELL BANKER RESIDENTIAL RE
$1,250,000 List price
1585 Chestnut Ave Winter Park, FL 32789
$10,000
Closing credit¹
4 beds
2 full, 1 partial
2,220 sqft
0.2 acres
$563 / sqft
House
Property details
About 1585 Chestnut Ave
Charming Spanish-Style Bungalow with Private Oasis in the Heart of Winter Park. Step into the elegance of Old Florida with this exquisite Spanish-style bungalow, nestled in Winter Park. Offering the perfect blend of historic charm and modern luxury, this 4-bedroom, 2.5-bath retreat is a hidden gem surrounded by lush, mature landscaping, creating a private sanctuary just minutes from the best Winter Park has to offer. From the moment you arrive, you’ll be captivated by the stunning curb appeal, featured on the front cover of Home & Garden magazine. The beautifully maintained exterior, with its 2023 terracotta-styled flat roof sets the stage for what lies within. Inside, timeless character meets contemporary upgrades. French terracotta flooring, antique hardware, and neutral warm tones create an inviting atmosphere, while thoughtful renovations ensure every modern convenience is at your fingertips. The kitchen is a chef’s dream, boasting vanilla quartz countertops with gold flecks, beautifully complementing the bronze accents and upgraded appliances. The open-concept design seamlessly connects the kitchen, dining, and living area ideal for entertaining. For more intimate gatherings, unwind in the spacious family room or soak in the natural light from the attached sunroom, which overlooks the lush backyard retreat. Step outside to a tranquil space perfect for morning coffee or evening cocktails, all while enjoying the peaceful sounds of nature. The pool and jacuzzi (new heater installed in 2021) add a touch of resort-style living, surrounded by meticulously curated landscaping with extensive landscape lighting (2022) that enhances the homes enchanting ambiance. Situated in a vibrant, walkable neighborhood known for its tree-lined streets and friendly atmosphere, this home is just a short stroll to Lake Knowles, the YMCA, and Phelps Park. Bring your golf cart and enjoy easy access to Interlachen Golf & Country Club or the Winter Park Racquet Club. Plus, you’re less than a mile from the newly renovated Winter Park Hospital and just minutes from Park Ave world-class dining and shopping. Top-rated schools: Zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. This rare, character-filled home offers a perfect blend of privacy, luxury, and location. Don’t miss your chance to own a piece of Winter Parks most desirable neighborhood!
Highlights
Home typeSingle Family Residence
HeatingCentral
StatusActive
CoolingCentral Air
Size2,220 sqft
Lot size0.17 Acres
Year built1959
MLS #O6280166
Attached garage1 space
Private poolYes
Virtual tour
Summary
- MLS Number: O6280166
- MLS Name: MFRMLS
- Office Name: KELLER WILLIAMS WINTER PARK
- Office Phone: (407) 545-6430
- Listing Agent: Ashley Landers
Listings courtesy of Stellar MLS as distributed by MLS GRID.
All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS.
Copyright 2025 My Florida Regional Multiple Listing Service DBA Stellar MLS. The real estate listing data marked with this icon comes from the IDX program of the Stellar MLS system. All information provided is deemed reliable but is not guaranteed and should be independently verified. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided exclusively for consumers’ personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Properties displayed may be listed or sold by various participants in the MLS.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 2/22/2025, 11:19:53 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
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$1,250,000
1585 Chestnut Ave
$10,000
closing credit¹
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Seller rebate
0.5% sale price²
Price information
Property sales
| Date | Event | Price |
|---|---|---|
| Jun 22, 2023 | Home Sold | $989,000 |
| Dec 12, 2019 | Home Sold | $572,000 |
| Sep 04, 2009 | Home Sold | $440,000 |
| Jan 21, 2003 | Home Sold | $340,000 |
| Nov 01, 2000 | Home Sold | $215,000 |
| Mar 31, 1999 | Home Sold | $199,000 |
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2023 | $587,537 | $8,635 |
| 2022 | $570,424 | $8,202 |
| 2021 | $553,810 | $8,202 |
| 2020 | $546,164 | $8,114 |
| 2018 | $326,362 | $4,758 |
| 2017 | $319,649 | $4,712 |
History based on county public records data.
Nearby schools
6
Lakemont Elementary School
Public District KG-5
0.5 mi
•901 N Lakemont Ave
9
Dommerich Elementary School
Public District KG-5
1.5 mi
•601 N Thistle Ln
7
Brookshire Elementary School
Public District PK-5
1.7 mi
•2500 Cady Way
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $75,154. Typical income of Winter Park, FL residents is between $35k-100k annually. Typical family type is single, no kids. Residents of this area typically have post secondary degree education.
How much money do the neighbors make?
22%
<35k
40%
35k-100k
25%
100k-200k
13%
200k+
What level of education do the neighbors have?
No High School
High School Diploma
Post Secondary Degree
Masters Degree
Doctorate
What types of families live nearby?
35%
Single, No Kids
8%
Single, with Kids
34%
Married, No Kids
23%
Married, with Kids
Are the neighbors home owners or renters?
Home Owners
Renters
How old are people in this area?
17%
<11 yrs old
7%
12-17 yrs old
16%
18-34 yrs old
48%
35-64 yrs old
12%
65+ yrs old
What do the neighbors do for fun?
Hiking/backpacking
Skiing/snowboarding
PGA/LPGA
Where do the neighbors shop?
Nordstrom Rack
Nordstrom
Chico's
Where do the neighbors go to eat?
Chipotle
California Pizza Kitchen
Bonefish Grill
What do the neighbors drive?
Mazda
BMW
Cadillac
What do the neighbors listen to?
Rock
Talk/Personality
Classical
All data provided by Home Junction and Claritas
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Frequently asked questions
About 1585 Chestnut Ave
This home is located at 1585 Chestnut Ave in Winter Park, FL and zip code 32789. This 2,220 square foot home, which was built in 1959, sits on a 0.17 acre lot. Features: 4 bedrooms, 3 bathrooms. It has been listed on Rocket Homes since February 13, 2025 and is currently priced at $1,250,000.
While more than 14 listings in Winter Park, FL in January 2025 were sold above asking price, there were more than 12 listings sold at asking price, and more than 43 were sold below. The inventory of homes for sale in Winter Park, FL between December and January 2025 increased by 0.2%. While the average time on the market in January 2025 was 63 days, the median list price was $471,465.
From Rocket Homes Real Estate and based on county public records data.