1585 Chestnut Ave, Winter Park, FL 32789
$1,250,000
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Home Description
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!
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Private Pool: True
- Pool Features: In Ground
- Spa Features: In Ground
- Interior Features: Ceiling Fans(s),Open Floorplan,Primary Bedroom Main Floor,Walk-In Closet(s)
- Appliances: Dishwasher,Disposal,Electric Water Heater
- Floor Covering: Brick,Carpet,Ceramic Tile
- Exterior Features: Garden,Irrigation System,Lighting,Outdoor Kitchen,Private Mailbox,Rain Gutters,Sidewalk
- Exterior Contruction: Block,Stucco
- Foundation: Slab
- Front Exposure: South
- Roof: Membrane,Tile
- Building Sqft: 2631
Available now at $1,250,000
Approximate Room Sizes / Descriptions
| Family Room | 19x13 | First | Ceramic Tile |
| Florida Room | 12x8 | First | Ceramic Tile |
| Family Room | 19x13 | First | Ceramic Tile |
| Kitchen | 7x14 | First | Ceramic Tile |
| Dining Room | 22x14 | First | Ceramic Tile |
| Living Room | 11x12 | First | Ceramic Tile |
| Balcony/Porch/Lanai | 13x13 | First | Brick/Stone |
| Bedroom 2 | 13x11 | First | Carpet |
| Bedroom 3 | 13x9 | First | Carpet |
| Primary Bedroom | | First | Ceramic Tile |
- Attached Garage: True
- Garage: True
- Garage Spaces: 1
- Carport: False
- Carport Spaces: 0
- Air Conditioning: Central Air
- Heating: Central
- Utilities: Electricity Connected,Sewer Connected,Water Connected
- Lot Sqft: 7492.00
- Lot Acres: 0.1700
- Total Acre: 0 to less than 1/4
- Lot Num: 12
- Style: Single Family Residence
- Building Num Floors: 1
- : 407-545-6430
Neighborhood
The average asking price of a 4 bedroom Winter Park home in this zip code is
$1,815,598 (45.2% more than this home).
This home is priced at $563/sqft,
which is 2.1% less than similar homes
in the 32789 zip code.
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Financial
- Approx Payment:$6,081*
- Taxes:$13,769
Area Stats
These statistics are updated daily from the My Florida Regional MLS. For further analysis or
to obtain statistics not shown below please call EasyStreet Realty at
(386) 801-5417 and speak with one of our real estate consultants.
Popular Homes
$530,222
$440,250
124
0.8%
53.2%
97
$529,790
$469,997
578
1.2%
47.1%
86
$920,991
$712,450
22
0.0%
45.5%
78
$441,715
$420,000
87
2.3%
57.5%
83
$1,329,045
$1,064,495
46
0.0%
50.0%
136
$712,868
$700,000
19
0.0%
52.6%
255
$632,356
$585,000
16
0.0%
62.5%
60
$562,060
$489,700
626
0.6%
51.6%
91
$1,266,914
$1,230,000
12
0.0%
25.0%
73
$491,602
$422,500
238
0.8%
47.1%
88
$436,075
$411,200
64
0.0%
34.4%
97
$520,730
$444,900
2264
1.5%
46.5%
105
$748,028
$550,000
167
1.2%
58.1%
92
$735,093
$575,000
73
0.0%
47.9%
93
$564,587
$539,445
130
0.8%
34.6%
96
$1,583,601
$1,112,124
49
0.0%
51.0%
144
$521,171
$469,000
181
1.1%
47.0%
80
$679,795
$484,900
2644
1.8%
47.7%
84
$705,851
$590,500
188
2.1%
45.2%
81
$332,649
$319,945
272
0.7%
61.4%
141
$1,759,920
$1,280,000
86
1.2%
48.8%
174
$546,262
$465,430
711
0.8%
66.5%
135
$529,253
$415,000
399
1.3%
53.1%
96
$566,519
$442,998
112
1.8%
59.8%
83
$2,159,018
$1,292,461
250
0.4%
44.8%
119
$827,322
$675,000
557
0.4%
46.3%
89
$559,324
$465,000
115
1.7%
51.3%
80
Listing Courtesy of KELLER WILLIAMS WINTER PARK.
For information or to schedule a viewing of this property (MLS# O6280166), call: 386 801 5417
1585 Chestnut Ave, Winter Park FL is a single family home of 2220 sqft and
is currently priced at $1,250,000
.
This single family home has 4 bedrooms.
A comparable home for sale at 1875 Staunton Ave in Winter Park is listed at $599,900.
In addition to single family homes, EasyStreet also makes it easy to find Homes, Condos, New Homes and Foreclosures
in Winter Park, FL.
Osceola Court, Lugano Terrace and Winter Park Heights are nearby neighborhoods.
MLS O6280166 has been posted on this site since 2/13/2025 (today).