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1585 Chestnut Avenue

Winter Park, FL 32789

Name: Open House: 11am-1pm
Start: 2025-02-22T11:00:00
End: 2025-02-22T13:00:00
Location: 1585 Chestnut Avenue

4 beds
3 baths
2,220 sqft
7,492 sqft lot
$563 per sqft
1959 build
– on site

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!

Listing courtesy of STELLAR_MLS / KELLER WILLIAMS WINTER PARK

Last checked: Checking… • Last updated Feb 19, 2025 •

MLS# O6280166 —

Upcoming Open Houses

Saturday, 2/22
11am-1pm

View more open houses in Winter Park, FL

The Building

Year Built:

1959
New Construction:

false
Construction Materials:

Block
Levels:

One
Stories Total:

1
Roof:

Membrane
Foundation Details:

Slab
Building Area Total:

2631
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Ceiling Fan(s)
Flooring:

Brick/Stone
Fireplace:

false

Room Dimensions

Living Area:

2220
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

From Park Ave head North to Palmer, then East to Temple Drive, Right on Chestnut, Home sweet home on Left
Latitude:

28.613886
Longitude:

-81.332217
Coordinates:

-81.332217, 28.613886

The Property

Parcel Number:

322130453601120
Property Type:

Residential
Property Subtype:

Single Family Residence
Lot Size Acres:

0.17
Lot Size Area:

7492
Lot Size SqFt:

7492
Lot Size Units:

Square Feet
Total Acres:

0 to less than 1/4
Zoning:

R-1A
Direction Faces:

South
View:

false
Exterior Features:

Garden
Fencing:

Wood
Water Source:

Public
Road Surface Type:

Brick
Flood Zone Code:

x
Additional Parcels:

false
Homestead:

false
Lease Restrictions:

true
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

12
Tax Block:

1
Tax Legal Description:

LAKE KNOWLES TERRACE K/4 LOT 12 BLK 1
Tax Book Number:

K-4
Tax Annual Amount:

13769.08

Beds

Bedrooms Total:

4

Baths

Total Baths:

2.5
Total Baths:

3
Full Baths:

2
Half Baths:

1

The Listing

Virtual Tour URL Branded:

www.tourdrop.com/dtour/389694/Zillow-3D
Virtual Tour URL Branded 2:

https://www.tourdrop.com/dtour/389694
Virtual Tour URL Unbranded:

https://www.propertypanorama.com/instaview/stellar/O6280166
Virtual Tour URL Unbranded 2:

https://player.vimeo.com/video/1055593840?autoplay=1
Special Listing Conditions:

None

Heating & Cooling

Heating:

Central
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

Electricity Connected
Sewer:

Public Sewer

Appliances

Appliances:

Dishwasher
Laundry Features:

In Garage

Schools

Elementary School:

Lakemont Elem
Middle Or Junior School:

Maitland Middle
High School:

Winter Park High

The Community

Subdivision Name:

LAKE KNOWLES TERRACE
Senior Community:

false
Community Features:

Sidewalks
Waterview:

false
Water Access:

false
Waterfront:

false
Spa:

true
Spa Features:

In Ground
Pool Private:

true
Pool Features:

In Ground
Association:

false
Ownership:

Fee Simple

Parking

Garage:

true
Attached Garage:

true
Garage Spaces:

1
Carport:

false
Covered Spaces:

1

Extra Units

Other Structures:

Outdoor Kitchen

Monthly cost estimate

Asking price

$1,250,000

Expense	Monthly cost
Mortgage	$6,693
Taxes	$1,147
Insurance	$343
Utilities	$219 See report
Total	$8,402/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Transit Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
2/16/25 Feb 16, 2025	Relisted	STELLAR_MLS	$1,250,000
2/14/25 Feb 14, 2025	Pending	STELLAR_MLS	$1,250,000
2/13/25 Feb 13, 2025	Listed / Active	STELLAR_MLS	$1,250,000	26.4% (15.6% / YR)

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This house located in Lake Knowles Terrace, Winter Park, FL 32789 is currently for sale for $1,250,000. 1585 Chestnut Avenue is a 2,220 square foot house with 4 beds and 3 baths that has been on Estately for 8 days. 1585 Chestnut Avenue is in the Lake Knowles Terrace neighborhood of Winter Park and has a WalkScore® of 19, making it car-dependent. This house is in the attendance area of Cornerstone Charter Academy K-8, Winter Park High School, Maitland Middle School, Cornerstone Charter Academy High School, and Lakemont Elementary School.

Listing Courtesy of: STELLAR_MLS and KELLER WILLIAMS WINTER PARK.

Based on information from the My Florida Regional MLS DBA Stellar MLS 2025.

All information provided is deemed reliable but is not guaranteed and should be independently verified. Stellar MLS, Estately and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing 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. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. Stellar MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. For any questions please call (407) 499-8911.

1585 Chestnut Avenue

Winter Park, FL 32789