WINTER PARK, FL 32789 1585 CHESTNUT AVENUE

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Presented By: KELLER WILLIAMS WINTER PARK with 407-545-6430. - 407-545-6430
  • MLS# O6280166
  • 02/13/2025
  • Request Tour
  • Request Info
  • Beds • 4
  • Full/Half Baths • 2 / 1
  • SQFT • 2,220
  • Garage • 1

Home Details

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!
Presented By: KELLER WILLIAMS WINTER PARK with 407-545-6430. - 407-545-6430

Interior Features for 1585 CHESTNUT AVENUE

Bedrooms

Total Bedrooms4

Bathrooms

Half Baths1
Total Baths3

Other Interior Features

LivingAreaSourcepublic records
Air Conditioning Y/NYes
Fireplace Y/NNo
Flooringbrick/stone, carpet, ceramic tile
Heating Y/NYes
Interior Amenitiesceiling fan(s), open floorplan, primary bedroom main floor, walk-in closet(s)
Laundry Featuresin garage
Total Stories1

General for 1585 CHESTNUT AVENUE

Additional Parcels Y/NNo
Appliancesdishwasher, disposal, electric water heater
Attached Garage Yes
Building Area Unitssquare feet
Carport Y/NNo
Citywinter park
Community Featuressidewalks
Construction Materialsblock, stucco
Coolingcentral air
Countyorange
Directionsfrom park ave head north to palmer, then east to temple drive, right on chestnut, home sweet home on left
DockY/NNo
Elementary Schoollakemont elem
Facing Directionsouth
Flood Zone Codex
Flood Zone Code XY
Full Baths2
Garage Spaces1
Garage Y/NYes
HOANo
Heatingcentral
High Schoolwinter park high
Land Lease Y/NNo
Lease Considered Y/NYes
Legal Descriptionlake knowles terrace k/4 lot 12 blk 1
Levelsone
Listing Termscash, conventional, fha, va loan
Living Area Unitssquare feet
Lot Size Square Feet7492
Lot Size Unitssquare feet
MLS Area32789 - winter park
Middle/Junior High Schoolmaitland middle
Minimum Lease1 month
ModificationTimestamp2025-04-23t22:05:04.397z
New ConstructionNo
Occupancy Typevacant
Other Structuresoutdoor kitchen
Ownershipfee simple
Pool Featuresin ground
Property Subtypesingle family residence
Property Typeresidential
Roofmembrane, tile
STELLAR_InLawSuiteYNNo
Senior Community Y/NNo
Sewerpublic sewer
Spa Featuresin ground
Standard Statusactive
Statusactive
Subdivision Namelake knowles terrace
Tax Annual Amount13769.08
Tax Lot12
Tax Year2024
Total Rooms10
Utilitieselectricity connected, sewer connected, water connected
Virtual TourClick here
Virtual TourClick here
Water Access Y/NNo
Water View Y/NNo
Waterfront Y/NNo
Year Built1959
Zoningr-1a

Exterior for 1585 CHESTNUT AVENUE

Building Area Total2631
Covered Spaces1
Exterior Amenitiesgarden, irrigation system, lighting, outdoor kitchen, private mailbox, rain gutters, sidewalk
Fencingwood
Foundation Detailsslab
Lot Size Acres0.17
Lot Size Area7492
Private PoolYes
Road Surface Typebrick
SpaYes
Water Sourcepublic

Additional Details

Price History

Schools

Elementary School Lakemont Elem
Middle School Maitland Middle
High School Winter Park High

Jonathan Alsaka

Price $1,100,000
MLS#O6280166
List Date 02/13/2025
Property Type Single Family
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