2040 RANDALL CIRCLE, Winter Park, FL 32789

• 5 beds |
• 6 baths |
• 4,636 sqft

Property Description

Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park Avenue. Inside, rich hardwood floors run throughout the living spaces, complemented by Restoration Hardware lighting that brings a refined, cohesive feel to every room. The welcoming foyer opens to a gracious formal living room with a gas fireplace and custom built-ins, an elegant yet comfortable space for entertaining or relaxing. Just beyond, the formal dining room is well proportioned for hosting holiday gatherings and dinner parties with ease. The heart of the home is the expansive chef’s kitchen, thoughtfully designed for everyday living and effortless entertaining. An oversized island anchors the space, topped with Carrara marble counters and offering generous seating. A dual Wolf oven with six-burner range plus French cooktop, custom cabinetry, walk-in pantry, and a butler’s pantry complete with under-counter wine refrigerator provide beauty and functionality. A spacious breakfast room filled with natural light overlooks the backyard and flows seamlessly into the family room. Here, a gas fireplace, custom built-ins and three sets of French doors create a warm focal point while inviting in the outdoors. The first-floor primary suite serves as a private retreat, featuring large windows with tranquil views of the pool and direct access to the covered lanai. Dual walk-in closets provide ample storage, and the spa-like primary bath is finished in Carrara marble, offering a large soaking tub and an expansive glass-enclosed shower with dual shower heads. Two powder baths, one thoughtfully designed as a pool bath, along with one of two laundry rooms complete the main level. Upstairs, four additional bedrooms and a dedicated office provide generous space for family and guests. Two of the bedrooms feature private en-suite baths, while the remaining two share a well-appointed Jack & Jill bath. One of these rooms is arranged as a bonus lounge, offering flexibility to serve as a fifth bedroom, media room or additional gathering space if desired. The thoughtful second-floor layout easily adapts to a variety of lifestyle needs, whether accommodating guests, growing families or multi-generational living. A secondary laundry room upstairs adds an added layer of everyday convenience. Outdoor living is equally impressive. The spacious covered lanai with summer kitchen overlooks the saltwater, heated pool and spa, creating an extension of the interior living space. Brick paver flooring continues from the lanai to the open patio, offering multiple areas for lounging, dining and entertaining beneath the Florida sky. Ideally in a desirable location and zoned for sought-after Audubon Park K-8, 2040 Randall Circle offers timeless style, thoughtful design and seamless indoor-outdoor living in one of the area’s charming neighborhoods.

Listing Status:

Active

Date Added:

March 5, 2026

Data Last Updated:

March 27, 2026 at 7:23PM

Listing Office:

PREMIER SOTHEBY'S INTL. REALTY : 407-644-3295

Listing Agent:

Mick Night : 407-629-4446

MLS ID:

O6386920

Interior

• General: Built-in FeaturesCoffered Ceiling(s)Crown MoldingEat-in KitchenHigh CeilingsKitchen/Family Room ComboPrimary Bedroom Main FloorSolid Wood CabinetsStone CountersWalk-In Closet(s)Window Treatments
• Rooms: Breakfast Room SeparateDen/Library/OfficeFamily RoomFormal Dining Room SeparateFormal Living Room SeparateInside Utility
• Appliances: Bar FridgeDishwasherDisposalMicrowaveRangeRange HoodRefrigeratorTankless Water Heater
• Laundry: InsideLaundry Room
• Flooring: TileWood
• A/C: Central AirZoned
• Heating: CentralZoned
• Fireplace: Family RoomGasLiving RoomOutsideFireplace

Exterior

• General: French DoorsLightingOutdoor KitchenRain GuttersSidewalkHeatedIn Ground
• Other Structures: Rear PorchCovered
• Pool: GuniteHeatedIn GroundLightingPool SweepSalt Water
• Parking: Garage Faces Side

Construction

• Roofing: Shingle
• General: BlockStuccoTwoSlab

Location

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

Lot

• Zoning: R-1AACHARMONT L/93 LOT 11 BLK C SEE 3059/389391 39307-22-30-1252-03-110
• Fencing: Fenced

Utilities

• Utilities: BB/HS Internet AvailableNatural Gas ConnectedPublicUnderground Utilities
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple