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Property for sale at 101 S NEW YORK AVENUE UNIT 311, WINTER PARK, FL, 32789
Property for sale at 101 S NEW YORK AVENUE UNIT 311, WINTER PARK, FL, 32789
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101 S New York Avenue Unit 311Winter Park, FL, 32789

3beds
4baths
3,112sqft
Condominium
Built in 2008
$1,303 Monthly HOA Fee
$1,775,000
For sale
$1,849,900−$74,900 (4%)Reduced Sep 9, 2026
Price per sqft
$570
Days on market
113
Listed Jun 17, 2026
MLS #O6416927Updated Oct 3, 2026

About this property

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).

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Property details

Property type
Condominium
Street address
101 S New York Avenue Unit 311
City
Winter Park
State
FL
ZIP code
32789
Year built
2008
New construction
No
Faces
East
Rooms
7
Building stories
5
Living area
3,112 sqft
Total building area
3,112 sqft
Levels
Two

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 8, 2026 at 4:01 AM EDT

Price & sale history

Asking price reduced by $74,900 (4%) since first listed.

EventPrice
Price reducedMLS #O6416927$1,775,000Change: −4%−$74,900
Listed for saleMLS #O6416927$1,849,900
SoldMLS #O5225043$875,000
Listed for saleMLS #O5225043$900,000
History may be incomplete.
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Property for sale at 101 S NEW YORK AVENUE UNIT 311, WINTER PARK, FL, 32789
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