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For sale
    • $1,849,900

    101 S NEW YORK AVENUE #311, WINTER PARK, FL 32789

    3beds
    3,112sqft
    : 
    $13,420/mo
    Get pre-qualified
    Condominium
    Built in 2008
    -- sqft lot
    $-- Zestimate®
    $594/sqft
    $1,525/mo HOA

    What's special

    Exquisitely renovated two-story condominiumSpacious breakfast bar islandHigh ceilingsCharming breakfast nookLight-filled open floor planDetailed crown moldingSpacious storage closet
    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).
    68 days
    |
    602
    |
    19
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Tiffany Grindstaff 407-252-0927,

    KELLY PRICE & COMPANY LLC 407-645-4321

    Source: Stellar MLS,MLS#: O6416927MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Utility Room
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: Second
      • Area: 325 Square Feet
      • Dimensions: 25x13
      Bedroom 1
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 168 Square Feet
      • Dimensions: 12x14
      Bedroom 2
      • Features: Walk-In Closet(s)
      • Level: Second
      • Area: 130 Square Feet
      • Dimensions: 10x13
      Dinette
      • Level: First
      • Area: 90 Square Feet
      • Dimensions: 10x9
      Dining room
      • Level: First
      • Area: 208 Square Feet
      • Dimensions: 13x16
      Kitchen
      • Features: Breakfast Bar, Built-in Features, Stone Counters
      • Level: First
      • Area: 165 Square Feet
      • Dimensions: 15x11
      Living room
      • Level: First
      • Area: 273 Square Feet
      • Dimensions: 21x13
      Heating
      • Central
      Cooling
      • Central Air
      Appliances
      • Included: Oven, Cooktop, Dishwasher, Microwave, Range, Refrigerator
      • Laundry: Inside, Laundry Room, Upper Level
      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)
      • Flooring: Hardwood
      • Doors: French Doors
      • Has fireplace: No
      Interior area
      • Total structure area: 3,112
      • Total interior livable area: 3,112 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Assigned, Guest, Reserved
      • Garage spaces: 2
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Covered, Enclosed, Patio
      • Exterior features: Balcony, Courtyard
      • Has view: Yes
      • View description: City, Park/Greenbelt
      Details
      • Parcel number: 062230967000311
      • Zoning: C-2
      • Special conditions: None

      Construction

      Type & style
      • Home type: Condo
      • Property subtype: Condominium
      Materials
      • Block, Brick, Stucco
      • Foundation: Slab
      • Roof: Built-Up,Tile
      Condition
      • New construction: No
      • Year built: 2008

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Available, Electricity Available

      Community & HOA

      Community
      • Features: Sidewalks
      • Security: Key Card Entry
      • Pet fee: $0 monthly
      • Subdivision: WINTER PARK RESIDENTIAL
      HOA
      • Has HOA: Yes
      • Amenities included: Elevator(s), Lobby Key Required, Maintenance
      • Services included: Maintenance Structure, Maintenance Grounds, Manager, Trash
      • HOA fee: $1,525 monthly
      • HOA name: Dominion Mgmt Solutions/Fernando
      • HOA phone: 407-930-4673
      Location
      • Region: Winter Park

      Financial & listing details

      • Price per square foot: $594/sqft
      • Tax assessed value: $1,135,900
      • Annual tax amount: $20,038
      • Date on market: 6/17/2026
      • Cumulative days on market: 69 days
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Brick

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        6/17/2026Listed for sale$1,849,900+12.1%$594/sqft
        Source: Stellar MLS #O6416927 Report a problem
        10/8/2025Listing removed$1,650,000$530/sqft
        Source: Stellar MLS #O6302823 Report a problem
        8/3/2025Price change$1,650,000-5.7%$530/sqft
        Source: Stellar MLS #O6302823 Report a problem
        4/25/2025Listed for sale$1,749,000+99.9%$562/sqft
        Source: Stellar MLS #O6302823 Report a problem
        9/29/2014Sold$875,000-2.8%$281/sqft
        Source: Public Record Report a problem
        6/10/2014Listing removed$900,000$289/sqft
        Source: Homevest Realty #O5225043 Report a problem
        5/22/2014Pending sale$900,000$289/sqft
        Source: Homevest Realty #O5225043 Report a problem
        5/22/2014Price change$900,000+899900%$289/sqft
        Source: Homevest Realty #O5225043 Report a problem
        5/10/2014Price change$100-100%
        Source: Auction.com Report a problem
        5/2/2014Price change$900,000-26.5%$289/sqft
        Source: Homevest Realty #O5225043 Report a problem
        3/9/2014Price change$1,225,000-1.5%$394/sqft
        Source: Coldwell Banker Residential Real Estate - Winter Park #O5204327 Report a problem
        2/27/2014Price change$1,244,000-0.4%$400/sqft
        Source: Coldwell Banker Residential Real Estate - Winter Park #O5204327 Report a problem
        1/17/2014Listed for sale$1,249,000+13.5%$401/sqft
        Source: Coldwell Banker Residential Real Estate - Winter Park #O5204327 Report a problem
        3/4/2008Sold$1,100,000$353/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$17,570 +2.4%$1,135,900 +3.7%
        2023$17,166 +11.6%$1,095,380 +10%
        2022$15,386 -2%$995,800
        2021$15,706 -1.7%$995,800
        2020$15,974 -1.7%$995,800
        2019$16,247 -9.1%$995,800 -7.2%
        2018$17,882 $1,072,786 -1.5%
        2017$17,882 +3.9%$1,089,200
        2016$17,219 +4.5%$1,089,200 +35.1%
        2015$16,476 -2.2%$806,000 -26.1%
        2014$16,839 +13.4%$1,090,400 +15%
        2013$14,854 +1.4%$948,173 -3.7%
        2012$14,653 +32.4%$984,127 +57.6%
        2011$11,071 -13.9%$624,492 -16.6%
        2010$12,863 $748,792 -12%
        2009-- $850,900 +286.8%
        2008$3,605 $220,000
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 32789

        Getting around

        95 / 100
        Walker's Paradise
        41 / 100
        Some Transit
        66 / 100
        Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Audubon Park K8
        • Middle: Audubon Park K-8
        • High: Winter Park High

        Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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