1585 Chestnut Ave Winter Park, FL 32789
4
Beds
2.5
Baths
2,220
Sq Ft
7,492
Sq Ft Lot
Highlights
- In Ground Pool
- Open Floorplan
- Whirlpool Bathtub
- Winter Park High Rated A+
- Outdoor Kitchen
- Sun or Florida Room
About This Home
As of June 2025Charming 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!
Last Agent to Sell the Property
KELLER WILLIAMS WINTER PARK Brokerage Phone: 407-545-6430 License #3442841 Listed on: 02/13/2025
Co-Listed By
KELLER WILLIAMS WINTER PARK Brokerage Phone: 407-545-6430 License #3443936
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $13,769
Year Built
- Built in 1959
Lot Details
- 7,492 Sq Ft Lot
- South Facing Home
- Wood Fence
- Irrigation Equipment
- Street paved with bricks
- Garden
- Property is zoned R-1A
Parking
- 1 Car Attached Garage
Home Design
- Slab Foundation
- Tile Roof
- Membrane Roofing
- Block Exterior
- Stucco
Interior Spaces
- 2,220 Sq Ft Home
- 1-Story Property
- Open Floorplan
- Ceiling Fan
- Family Room
- Living Room
- Dining Room
- Sun or Florida Room
- Laundry in Garage
Kitchen
- Dishwasher
- Disposal
Flooring
- Brick
- Carpet
- Ceramic Tile
Bedrooms and Bathrooms
- 4 Bedrooms
- En-Suite Bathroom
- Walk-In Closet
- Sunken Shower or Bathtub
- Private Water Closet
- Whirlpool Bathtub
Pool
- In Ground Pool
- In Ground Spa
Outdoor Features
- Outdoor Kitchen
- Exterior Lighting
- Rain Gutters
- Private Mailbox
Schools
- Lakemont Elementary School
- Maitland Middle School
- Winter Park High School
Utilities
- Central Heating and Cooling System
- Electric Water Heater
Community Details
- No Home Owners Association
- Lake Knowles Terrace Subdivision
Listing and Financial Details
- Visit Down Payment Resource Website
- Legal Lot and Block 12 / 1
- Assessor Parcel Number 32-21-30-4536-01-120
Ownership History
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Feb 13, 2025
Closed on
Jun 10, 2025
Sold by
Ppre Llc
Bought by
Swetmon David W and Swetmon Lori Shawn
Seller's Agent
Ashley Landers
KELLER WILLIAMS WINTER PARK
Buyer's Agent
Olivia Maxwell
FANNIE HILLMAN & ASSOCIATES
List Price
$1,250,000
Sold Price
$987,500
Premium/Discount to List
-$262,500
-21%
Views
174
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
180.31%
Purchase Details
Listed on
Apr 13, 2023
Closed on
Jun 5, 2023
Sold by
Goulder Janice
Bought by
Ppre Llc
Seller's Agent
Janny Goulder
KELLER WILLIAMS WINTER PARK
Buyer's Agent
Janny Goulder
KELLER WILLIAMS WINTER PARK
List Price
$989,000
Sold Price
$989,000
Views
38
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
-0.08%
Purchase Details
Listed on
Nov 8, 2019
Closed on
Dec 9, 2019
Sold by
Hawkins Bruce F and Hawkins Wendy W
Bought by
Goulder Samuel and Goulder Janice
Seller's Agent
Maria Van Warner
FANNIE HILLMAN & ASSOCIATES
Buyer's Agent
Janny Goulder
KELLER WILLIAMS WINTER PARK
List Price
$579,000
Sold Price
$572,000
Premium/Discount to List
-$7,000
-1.21%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
16.99%
Original Mortgage
$457,600
Interest Rate
3.7%
Mortgage Type
New Conventional
Purchase Details
Closed on
Aug 31, 2009
Sold by
Martin Daniel M and Martin Sheila C
Bought by
Hawkins Bruce F
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$396,000
Interest Rate
4.62%
Mortgage Type
New Conventional
Purchase Details
Closed on
Dec 6, 2002
Sold by
Swanson James T and Swanson Nicole D
Bought by
Martin Daniel M and Martin Sheila C
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$272,000
Interest Rate
6.16%
Purchase Details
Closed on
Nov 1, 2000
Sold by
Biron Michael D and Kelly Christian E
Bought by
Swanson James T and Swanson Nicole D
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$193,500
Interest Rate
7.94%
Mortgage Type
New Conventional
Purchase Details
Closed on
Mar 31, 1999
Sold by
Vanderspool Thomas O and Vanderspool Mary C
Bought by
Biorn Michael D and Biorn Christian E
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$202,918
Interest Rate
6.82%
Mortgage Type
VA
Similar Homes in Winter Park, FL
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area
Home Values in the Area
Average Home Value in this Area
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $987,500 | None Listed On Document | |
| Warranty Deed | $989,000 | Champion Title & Closing | |
| Warranty Deed | $572,000 | First American Title Ins Co | |
| Warranty Deed | $440,000 | Aloma Title Company | |
| Warranty Deed | $340,000 | Magic Title Inc | |
| Warranty Deed | $215,000 | -- | |
| Warranty Deed | $199,000 | -- |
Source: Public Records
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $457,600 | New Conventional | |
| Previous Owner | $374,000 | New Conventional | |
| Previous Owner | $396,000 | New Conventional | |
| Previous Owner | $272,000 | No Value Available | |
| Previous Owner | $50,000 | Credit Line Revolving | |
| Previous Owner | $220,000 | New Conventional | |
| Previous Owner | $193,500 | New Conventional | |
| Previous Owner | $202,918 | VA |
Source: Public Records
Property History
| Date | Event | Price | Change | Sq Ft Price |
|---|---|---|---|---|
| 06/10/2025 06/10/25 | Sold | $987,500 | -10.2% | $445 / Sq Ft |
| 05/25/2025 05/25/25 | Pending | -- | -- | -- |
| 04/21/2025 04/21/25 | Price Changed | $1,100,000 | -10.2% | $495 / Sq Ft |
| 03/20/2025 03/20/25 | Price Changed | $1,225,000 | -2.0% | $552 / Sq Ft |
| 02/16/2025 02/16/25 | For Sale | $1,250,000 | 0.0% | $563 / Sq Ft |
| 02/14/2025 02/14/25 | Pending | -- | -- | -- |
| 02/13/2025 02/13/25 | For Sale | $1,250,000 | +26.4% | $563 / Sq Ft |
| 06/05/2023 06/05/23 | Sold | $989,000 | 0.0% | $409 / Sq Ft |
| 04/19/2023 04/19/23 | Pending | -- | -- | -- |
| 04/13/2023 04/13/23 | For Sale | $989,000 | +72.9% | $409 / Sq Ft |
| 12/10/2019 12/10/19 | Sold | $572,000 | -1.2% | $236 / Sq Ft |
| 11/11/2019 11/11/19 | Pending | -- | -- | -- |
| 11/08/2019 11/08/19 | For Sale | $579,000 | -- | $239 / Sq Ft |
Source: Stellar MLS
Tax History Compared to Growth
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $13,769 | $891,820 | $400,000 | $491,820 |
| 2024 | $8,635 | $870,200 | $400,000 | $470,200 |
| 2023 | $8,635 | $587,537 | $0 | $0 |
| 2022 | $8,203 | $570,424 | $0 | $0 |
| 2021 | $8,115 | $553,810 | $0 | $0 |
| 2020 | $7,805 | $546,164 | $300,000 | $246,164 |
| 2019 | $4,788 | $332,563 | $0 | $0 |
| 2018 | $4,758 | $326,362 | $0 | $0 |
| 2017 | $4,712 | $459,423 | $230,720 | $228,703 |
| 2016 | $4,614 | $447,339 | $224,000 | $223,339 |
| 2015 | $4,725 | $406,902 | $196,000 | $210,902 |
| 2014 | $4,764 | $339,022 | $149,000 | $190,022 |
Source: Public Records
Agents Affiliated with this Home
-
A
Seller's Agent in 2025
Ashley Landers
KELLER WILLIAMS WINTER PARK
(407) 429-8559
5 in this area
42 Total Sales
-
Seller Co-Listing Agent in 2025
Janny Goulder
KELLER WILLIAMS WINTER PARK
(407) 453-0687
4 in this area
27 Total Sales
-
Buyer's Agent in 2025
Olivia Maxwell
FANNIE HILLMAN & ASSOCIATES
(407) 222-4440
28 in this area
52 Total Sales
-
Seller's Agent in 2019
Maria Van Warner
FANNIE HILLMAN & ASSOCIATES
(407) 644-1234
63 in this area
183 Total Sales
Map
Source: Stellar MLS
MLS Number: O6280166
APN: 32-2130-4536-01-120
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Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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