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$1,849,900 - 101 S New York Avenue 311, WINTER PARK

3
Bedrooms
4
Baths
3,112
SQ. Feet
2008
Year Built

Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

Essential Information

  • MLS® #:
    O6416927
  • Price:
    $1,849,900
  • Bedrooms:
    3
  • Bathrooms:
    4.00
  • Full Baths:
    3
  • Half Baths:
    1
  • Square Footage:
    3,112
  • Year Built:
    2008
  • Type:
    Residential
  • Sub-Type:
    Condominium
  • Status:
    Active

Community Information

  • Address:
    101 S New York Avenue 311
  • Area:
    Winter Park
  • Subdivision:
    WINTER PARK RESIDENTIAL
  • City:
    WINTER PARK
  • County:
    Orange
  • State:
    FL
  • Zip Code:
    32789-4291

Amenities

  • Amenities:
    Elevator(s), Lobby Key Required, Maintenance
  • Parking:
    Assigned, Guest, Reserved
  • # of Garages:
    2
  • View:
    City, Park/Greenbelt

Interior

  • Interior Features:
    Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Living Room/Dining Room Combo, PrimaryBedroom Upstairs, Solid Wood Cabinets, Stone Counters, Thermostat, Walk-In Closet(s)
  • Appliances:
    Built-In Oven, Cooktop, Dishwasher, Microwave, Range, Refrigerator
  • Heating:
    Central
  • Cooling:
    Central Air
  • # of Stories:
    5

Exterior

  • Exterior Features:
    Balcony, Courtyard, French Doors
  • Roof:
    Built-Up, Tile
  • Foundation:
    Slab

School Information

  • Elementary:
    Audubon Park K8
  • Middle:
    Audubon Park K-8
  • High:
    Winter Park High

Additional Information

  • Days on Market:
    48
  • Zoning:
    C-2

Listing Details

  • Listing Office:
    Kelly Price & Company Llc

Listing information courtesy of Kelly Price & Company Llc.

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Listing data comes from My Florida Regional MLS.

Listing information last updated on August 6th, 2026 at 1:37am EDT.