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1723 CHESTNUT AVENUE

House Active With Contract
$1,125,000

BTC: 18.20388350

ETH: 644.32989691

1 days
3 bds
2 ba
2,608 sqft

Overview

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.

Location

Details

Type:
Residential
Parking:
Circular Driveway / Driveway / Garage Door Opener / Guest
Year Built:
1962
Lot:
0.27 Acres
Heating:
Central / Heat Pump
Price/sqft:
$431
Cooling:
Central Air
HOA:
No Data

Valuation

Our model vs. what's actually selling nearby.
Estimate
$477,000
$417K – $632K
Confidence Low
List vs. estimate
$648K above estimate
List $1,125,000 · +135.8%
Our model says this listing is priced above recent comparable activity. Room to negotiate.
Price per sq ft
$431
-6.6% vs. city median $461
Based on
6 MLS comparables
Median of recent comparable listings. Sold comps use closing price, active listings use list price.

Highlights

Annual tax
$4,879
2025
Pool
Gunite
Garage
2 car garage
All facts and features
  • Flooring

    • Hardwood

    Heating

    • Central

    • Heat Pump

    Cooling

    • Central Air

    Appliances

    • Bar Fridge

    • Dishwasher

    • Disposal

    • Gas Water Heater

    • Microwave

    • Range

    • Refrigerator

    • Tankless Water Heater

    Other interior features

    • Crown Molding

    • Open Floorplan

    • Primary Bedroom Main Floor

    • Solid Surface Counters

    • Solid Wood Cabinets

    • Walk-In Closet(s)

    Bedrooms and bathrooms

    • Bedrooms: 3

    • Bathrooms: 1

    • Full bathrooms: 2

  • Parking

    • Circular Driveway

    • Driveway

    • Garage Door Opener

    • Guest

    Property

    • Levels: One

    • Pool Private: Yes

    • Exterior Features: French Doors / Irrigation System / Rain Gutters

    Lot

    • Lot: 0.27 Acres

    Other Property Information

    • Parcel Number: 322130170801060

    • Zoning: R-1A

  • Type and style

    • Property Type: Residential

    • Property Sub Type: Single Family Residence

  • Utility

    • Cable Connected

    • Electricity Connected

    • Propane

    • Sewer Connected

  • Other financial information

    • Annual tax amount: $4,880

  • Source details

    • MLS ID: O6402563

    Other facts

    • Construction Materials: Block / Stucco

    • Foundation Details: Slab

    • Fireplace Features: Family Room

    • Laundry Features: Inside / Laundry Room

    • Lot Features: Landscaped

    • Patio And Porch Features: Covered / Front Porch / Patio / Rear Porch

    • Pool Features: Gunite / In Ground / Tile

    • Direction Faces: South

    • Architectural Style: Traditional

    • Fireplace: Yes

    • Garage Spaces: 2

    • Attached Garage: Yes

    • Garage: Yes

    • Living Area: 2608

    • Water Source: None

    • Lot Size Dimensions: 77 x 150

    • Subdivision Name: CONWILL ESTATES

Private inquiry
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The multiple listing information is provided by the Stellar MLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are ©2026-present Stellar MLS. All Rights Reserved. The information provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Listing courtesy of: ANNE ROGERS REALTY GROUP INC