Sell Your Home
Get a free home valuation
Contact
Tell us about your needs

101 S NEW YORK AVENUE UNIT 311

Condo/Co-op For Sale
$1,849,900

BTC: 29.36349206

ETH: 1,051.07954545

1 days
3 bds
3 ba
3,112 sqft

Overview

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).

Location

Details

Type:
Residential
Parking:
Assigned / Guest / Reserved
Year Built:
2008
Lot:
No Data
Heating:
Central
Price/sqft:
$594
Cooling:
Central Air
HOA:
$1,303

Valuation

Our model vs. what's actually selling nearby.
Estimate
$1,450,000
$809K – $1.7M
Confidence Low
List vs. estimate
$399K above estimate
List $1,849,900 · +27.6%
Our model says this listing is priced above recent comparable activity. Room to negotiate.
Price per sq ft
$594
+178.9% vs. city median $213
Based on
7 MLS comparables
Median of recent comparable listings. Sold comps use closing price, active listings use list price.

Highlights

Annual tax
$20,038
2025
HOA
$1,302/mo
Maintenance Structure, Maintenance Grounds, Manager
View
City, Park/Greenbelt
Garage
2 car garage
Pets
Allowed
All facts and features
  • Flooring

    • Hardwood

    Heating

    • Central

    Cooling

    • Central Air

    Appliances

    • Built-In Oven

    • Cooktop

    • Dishwasher

    • Microwave

    • Range

    • Refrigerator

    Other 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)

    Bedrooms and bathrooms

    • Bedrooms: 3

    • Bathrooms: 1

    • Full bathrooms: 3

  • Parking

    • Assigned

    • Guest

    • Reserved

    Property

    • Levels: Two

    • Exterior Features: Balcony / Courtyard / French Doors

    Other Property Information

    • Parcel Number: 062230967000311

    • Zoning: C-2

  • Type and style

    • Property Type: Residential

    • Property Sub Type: Condominium

  • Utility

    • Cable Available

    • Electricity Available

  • Other financial information

    • HOA: $1,303

    • HOA Frequency: Monthly

    • Annual tax amount: $20,039

  • Source details

    • MLS ID: O6416927

    Other facts

    • Construction Materials: Block / Brick / Stucco

    • Foundation Details: Slab

    • Laundry Features: Inside / Laundry Room / Upper Level

    • Patio And Porch Features: Covered / Enclosed / Patio

    • Direction Faces: East

    • Garage Spaces: 2

    • Garage: Yes

    • Living Area: 3112

    • Water Source: Public

    • Subdivision Name: WINTER PARK RESIDENTIAL

Private inquiry
Talk to the advisor on this listing.
Floor plans, HOA docs, off-market comparables, scheduling a private showing — one message, direct to the local specialist.

More like this

For Sale
$1,399,000
Townhouse
3 bds · 2 ba · 2,585 sqft
VILASA TWNHMS, WINTER PARK
512 W SWOOPE AVENUE
New
For Sale
$2,350,000
Condo/Co-op
3 bds · 3 ba · 2,143 sqft
LANDMARK WINTER PARK CONDO, WINTER PARK
140 E MORSE BOULEVARD UNIT J
New
For Sale
$1,795,000
House
4 bds · 4 ba · 2,819 sqft
WINTER PARK VILLAGE, WINTER PARK
2501 LAFAYETTE AVENUE
New
For Sale
$1,499,000
House
5 bds · 4 ba · 4,814 sqft
REPLAT BLK B POORS ADD, MAITLAND
255 W GEORGE AVENUE
New
For Sale
$1,550,000
House
4 bds · 3 ba · 3,578 sqft
WINDSONG ELIZABETHS WALK 43/81, WINTER PARK
1421 CHAPMAN CIRCLE
New
For Sale
$1,595,000
Lots/Land
0.41 acres
TUSCANY TERRACE, WINTER PARK
1113 VIA DEL MAR
New
For Sale
$2,250,000
House
5 bds · 4 ba · 2,889 sqft
SYLVAN HEIGHTS, WINTER PARK
240 N PHELPS AVENUE
For Sale
$1,429,000
House
5 bds · 4 ba · 2,351 sqft
ORWIN MANOR WESTMINSTER SEC, WINTER PARK
1473 BERKSHIRE AVENUE

Market around this address

Live counts in the same area.
View all

The multiple listing information is provided by the Stellar MLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are ©2026-present Stellar MLS. All Rights Reserved. The information provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Listing courtesy of: KELLY PRICE & COMPANY LLC