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$1,775,000
3 Beds ⋅ 4 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code
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).

101 S New York Avenue Unit 311, Winter Park
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Orange County › Winter Park › Winter Park Residential

Winter Park Residential, Winter Park

Winter Park Residential is a 2000s neighborhood in Winter Park, in the 32789 zip code. Homes are block and brick. Most homes fall between about 2,600 and 3,200 square feet under air, the median lot is roughly half an acre, and a two car garage is standard.

Homes here carry an HOA, billed monthly, typically around $574. Confirm the figure on a specific parcel before relying on it.

What the homes are

  • Built Essentially all built in the 2000s.
  • Construction Block and brick. Built-Up roofs are near universal.
  • Size Most homes fall between about 2,600 and 3,200 square feet under air.
  • Bedrooms Three bedrooms is the most common plan.
  • Garage A two car garage is standard.
  • Lot The median lot is roughly half an acre.
  • HOA Billed monthly, typically around $574. Confirm on a specific parcel before relying on it.

Where Winter Park Residential is

Winter Park Residential, centered at 28.597448, -81.3533. Drag to explore.
Street level, inside the neighborhood. Drag to look around.

Drive times below are measured on the road network from the center of Winter Park Residential, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving toTimeMiles
Downtown Orlando18 min6.2
Walt Disney World33 min26.2
Orlando International Airport37 min15.6
Universal Orlando25 min14.3

Public schools nearby

  • Park Maitland School of Winter Park 7 min, 1.6 mi
  • Lakemont Elementary School 8 min, 2.4 mi
  • Killarney Elementary School 9 min, 2.3 mi
  • Hungerford Elementary School 10 min, 2.7 mi

Private schools nearby

  • St. Margaret Mary Catholic School 3 min, 0.5 mi

Parks and recreation

  • Central Park 1 min, 0.2 mi
  • Downtown Winter Park 1 min, 0.2 mi
  • Winter Park 2 min, 0.3 mi
  • Shady Park 3 min, 0.5 mi

Groceries and errands

  • Greater Lifestyle Foods 2 min, 0.3 mi
  • The Ancient Olive Gourmet of Winter Park 3 min, 0.3 mi
  • Publix Super Market at Winter Park Village 4 min, 0.9 mi
  • Trader Joe's 4 min, 0.9 mi

Nearest is not the same as zoned. The schools above are the closest ones to Winter Park Residential by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Winter Park Residential actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 3 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated September 2026.

Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.

What homes sold for in Winter Park Residential

$1,129,000Median sale price
$432Median per square foot
4 daysMedian days to contract
3Homes sold in 12 months

Sale prices ran from $1,000,000 to $1,640,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

Homes priced right sold far faster

Median days to go under contract. Shorter is better.

Never reduced 2 sales, closed at 98.4% of asking4 days
Reduced at least once 1 sales, closed at 69% of the reduced price36 days

Sellers who priced correctly and held their number went under contract in a median 4 days. Sellers who had to reduce took 36 days and still closed at 69% of their already reduced price, after a typical cut of $180,000. Opening high costs time and money, in that order.

How buyers paid

Conventional 2 sales50%
Cash 2 sales50%

Cash was 50% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.

Questions about a specific home in Winter Park Residential, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for Winter Park Residential in Winter Park, Orange County, covering closed sales from 25 September 2025 through 20 September 2026, refreshed monthly and current as of September 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.