1723 CHESTNUT AVENUE, Winter Park, FL 32789

• 3 beds |
• 3 baths |
• 2,608 sqft

Property Description

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.

Listing Status:

Pending

Date Added:

May 7, 2026

Data Last Updated:

May 12, 2026 at 1:23AM

Listing Office:

ANNE ROGERS REALTY GROUP INC : 407-649-4141

Listing Agent:

Anne Rogers : 407-649-4141

MLS ID:

O6402563

Interior

• General: Crown MoldingOpen FloorplanPrimary Bedroom Main FloorSolid Surface CountersSolid Wood CabinetsWalk-In Closet(s)
• Rooms: Den/Library/OfficeFamily RoomFormal Dining Room SeparateInside Utility
• Appliances: Bar FridgeDishwasherDisposalGas Water HeaterMicrowaveRangeRefrigeratorTankless Water Heater
• Laundry: InsideLaundry Room
• Flooring: Wood
• A/C: Central Air
• Heating: CentralHeat Pump
• Fireplace: Family RoomFireplace

Exterior

• General: French DoorsRain GuttersIn Ground
• Style: Traditional
• Other Structures: Front PorchRear PorchPatioCovered
• Pool: GuniteIn GroundTile
• Parking: Circular DrivewayDrivewayGarage Door OpenerGuest

Construction

• Roofing: Shingle
• General: BlockStuccoOneSlab

Location

• Road/Access: Asphalt
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: R-1ACONWILL ESTATES S/13 LOT 6 BLK A32-21-30-1708-01-060
• Fencing: FencedVinyl

Utilities

• Utilities: Cable ConnectedElectricity ConnectedPropaneSewer Connected
• Water: None
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple