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101 S NEW YORK AVENUE #311, WINTER PARK, FL - photo 1

$1,775,000

101 S NEW YORK AVENUE #311

WINTER PARK, FL 32789

Estimated payment $10,650/month

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3Beds
4Baths
3,112Sq Ft
$570Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

HOA $1302/mo
Garage
Built in 2008

About This Home

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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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:3
  • •Bathrooms:4
  • •Full bathrooms:0

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:3,112 sqft
  • •Total interior livable area:3,112 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:N/A

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Condominium
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:2008

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Price history

DateEventPrice
2026-06-17T00:00:00.000ZListed for sale$1,775,000$570/sqft

Listing Agent

Tiffany Grindstaff

KELLY PRICE & COMPANY LLC

Brokerage Phone: 407-645-4321

Source: Stellar MLS · MLS #O6416927

Data Powered by Home Junction, Inc.

Nearby

Schools

ROLLINS COLLEGE

0.4 mi

VALENCIA COLLEGE - WINTER PARK CAMPUS

0.4 mi

LA AMISTAD

Elementary · 1.3 mi

Supermarkets

Quantum

0.0 mi

Healthfocus

0.3 mi

Publix

0.6 mi

Dining

extact

0.2 mi

Briarpatch Restaurant

0.2 mi

Orchid

0.2 mi

Parks

Central Park

0.1 mi

Shady Park

0.3 mi

Alfred J. Hanna Mini Park

0.4 mi

Beaches

Lake Baldwin Park Beach

2.2 mi

Conrad Beach

16.8 mi

West Beach

16.9 mi

Nearby amenity locations include data © OpenStreetMap contributors.