1723 CHESTNUT AVENUE Winter Park, FL $ 1,125,000
1723 CHESTNUT AVENUE
$ 1,125,000
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1723 CHESTNUT AVENUE

Winter Park, FL, 32789
$ 1,125,000
Bedrooms3 Baths2.1 Sq 2,608

Monthly Estimate*

$ 6,927

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Single Family Home for sale in Winter Park, FL

for $1,125,000 with 3 bedrooms and 2 full baths, 1 half bath. This 2,608 square foot home was built in 1962 on a lot size of 0.27.

Welcome to this thoughtfully expanded one-story home in Winter Park’s coveted “Tree Streets” neighborhood. A paved double drive and circular driveway create a gracious arrival with ample guest parking. Originally built in 1962 and expanded over time, this home offers a flexible floor plan designed for comfortable everyday living and effortless entertaining. Spacious living areas and the primary suite open to a stunning garden-like backyard, seamlessly connected by a full-length covered portico perfect for enjoying Florida’s indoor-outdoor lifestyle. The main hallway leads to the primary and guest bedrooms, along with a quiet sitting room overlooking the charming front porch. Expanded in the early 2000s, the private primary suite includes a generous bath with an oversized whirlpool tub, dual vanities, separate shower, dressing table, private water closet, and a spacious walk-in closet. At the heart of the home, the kitchen features solid wood cabinetry and solid-surface countertops, opening to the central family room with a traditional fireplace and casual dining area, all adjacent to the formal dining room. Just off the kitchen, a large flex space offers extensive built-ins, a desk area, dry bar, wine refrigerator, and integrated washer and dryer ideal for a home office, hobby room, or additional entertaining space. Located just minutes from Park Avenue, enjoy easy access to fine dining, boutique shopping, cafés, museums, and year-round community events. This one-story home offers abundant living space, exceptional entertaining areas, and a beautifully landscaped backyard complete with pool and outdoor living spaces all situated on a generous 77 x 150 lot.

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Single Family Pending

Price

$ 1,125,000

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 4,879

Style

Traditional

Lot Size

0.27

Year Built

1962

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6402563

Features
General
Sewer Public Sewer
Heating Central Heat Pump
Cooling Central Air
Utilities Cable Connected Electricity Connected Propane Sewer Connected
Possession Close Of Escrow
Roof Shingle
Appliances Bar Fridge Dishwasher Disposal Gas Water Heater Microwave Range Refrigerator Tankless Water Heater
Zoning R-1A
Garage Spaces 2
Patio/Porch Features Covered Front Porch Patio Rear Porch
Architectural Style Traditional
Pool Features Gunite In Ground Tile
Construction Materials Block Stucco
Year Built 1962
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name CONWILL ESTATES
Facing Direction South
Garage Y/N true
Total Rooms 9
Full Baths 2
Status Pending
Directions From North Park Avenue drive East on Palmer turn left on Phelps then right on Chestnut. From N Lakemont Drive continue straight to Arbor Park Drive then left on Chestnut
High School Winter Park High
City WINTER PARK
Senior Community Y/N false
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 11551
Carport Y/N false
Listing Terms Cash Conventional
Spa Features In Ground
Elementary School Lakemont Elem
Land Lease Y/N false
Tax Annual Amount 4879.56
Middle/Junior High School Maitland Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6402563
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Pending
Occupancy Type Owner
Tax Lot 6
Legal Description CONWILL ESTATES S/13 LOT 6 BLK A
Minimum Lease 7 Months
Water Access Y/N false
Additional Rooms Den/Library/Office Family Room Formal Dining Room Separate Inside Utility
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Crown Molding Open Floorplan Primary Bedroom Main Floor Solid Surface Counters Solid Wood Cabinets Walk-In Closet(s)
Flooring Hardwood
Furnished Y/N Unfurnished
Fireplace Features Family Room
Total Stories 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 1
Laundry Features Inside Laundry Room
Total Bedrooms 3
Total Baths 3
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Exterior
Exterior Amenities French Doors Irrigation System Rain Gutters
Vegetation Mature Landscaping
Fencing Fenced Vinyl
Parking Features Circular Driveway Driveway Garage Door Opener Guest
Lot Features Landscaped
Water Source None
Lot Size Area 11551
Foundation Details Slab
Spa true
Building Area Total 3882
Lot Dimensions 77 x 150
Lot Size Acres 0.27
Road Surface Type Asphalt
Private Pool true
Waterfront Y/N false
Covered Spaces 2
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* Excluded Features
List By
Anne Rogers Realty Group Inc

Broker

annerogersrealty@gmail.com

Email

Affordability Calculator

$7,333
Per Month
94%
6%
0%
Monthly Principal & Interest
$6,927
Monthly Property Taxes
$407
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
Pricing History
DatePricePrice ChangeDescription
5/7/2026$1,125,000 Listed Price

Map


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1723 CHESTNUT AVENUE, Winter Park, FL, 32789 is a Single Family Home for sale at $1,125,000 with 2,608 sqft and a lot size of 0.27. 1723 CHESTNUT AVENUE has 3 bedrooms, 2.1 baths, and was built in 1962. The property's zip code is 32789 which is in Winter Park, FL