About This Home

This 3-bedroom, 4-bathroom condo at 101 S NEW YORK Avenue #311 in Winter Park, FL is listed for $1,775,000 ($570 per sqft). Built in 2008, the home offers 3,112 sqft of living space on a N/A lot.

Key Features

  • Built in 2008
  • 2 stories

Property Details

2 stories
3 full, 1 half
2-car garage
#311
2008

Amenities

ViewA/CRV Parking
Listing Description

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 sui

te 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).

Monthly Cost Estimate

$9,493/mo

20% down · 6.5% · 30 years

Principal$1,284
Interest$7,692
Insurance$518

Estimates only. Actual payments may vary.

Location

101 S NEW YORK Avenue #311

Winter Park, FL 32789

WINTER PARK RESIDENTIAL

Features & Amenities

Interior Features

Ceiling Fans(s)Crown MoldingEat-in KitchenLiving Room/Dining Room ComboPrimaryBedroom UpstairsSolid Wood CabinetsStone CountersThermostatWalk-In Closet(s)

Exterior Features

BalconyCourtyard

Property Details

Flooring

Wood

Construction

Block Brick Stucco

Views

CityPark

Outdoor Features

Patio

Parking

GuestRVAssigned

Heating

Central

Cooling

Central Air

Appliances

Built-In OvenCooktopDishwasherMicrowaveRangeRefrigerator

Questions & Answers

This 3-bedroom, 4-bathroom condo at 101 S NEW YORK Avenue is listed at $1,775,000 ($570/sqft). The estimated monthly payment is $9,493 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 2008, 2 stories. Interior Features: Ceiling Fans(s), Crown Molding, Eat-in Kitchen. Exterior Features: Balcony, Courtyard.

This property is listed by Tiffany Grindstaff.

TG

Tiffany Grindstaff

Agent at Kelly Price & Company

Listed by Kelly Price & Company · Broker phone: (407) 645-4321 · View on Broker Site · Broker website

MLS# O6416927· Source: Stellar MLS· 132 days on PropertySimple

Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

101 S NEW YORK Avenue #311, Winter Park, FL 32789

Open this listing in: