101 S New York Ave #311, photo 1
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Overview

3 bd4 ba3,112 sqft2 car garageCondominium
TypeCondominium
HOA$1,302.65/mo
Built2008
Living area3,112 sqft
Price / sqft$570
Garage2 car

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About this home

Ceiling Fans(s)Crown MoldingEat-in KitchenLiving Room/Dining Room ComboPrimarybedroom UpstairsSolid Wood CabinetsStone CountersThermostat

101 S New York Ave #311 is a 2008-built home in Winter Park Residential, Winter Park. Inside you'll find 3 bedrooms, 4 bathrooms, and 3,112 square feet of living space. Listed at $1,775,000 (about $570/sqft), 115 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $1,302.65 monthly.

From the listing

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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The essentials

Built
2008
Price / sqft
$570
On market
115 days
Annual tax
$20,039
HOA
$1,302.65/mo
Flood zone
X · Low risk
Type
Condominium

At a glance

Condo
5 stories · 2008
2 car garage
Assigned
Private balcony
Outdoor space
3,112 sqft
Living area

Payment

Est. monthly payment
$13,117/mo
Down payment (20%)
$355,000
Property taxes
$1,670/mo
HOA
$1,302.65/mo
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Condominium
Year Built
2008
Lot
-
Cooling
Central Air
Heating
Central
Parking
Assigned, Guest, Reserved
Days on Market
115
Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
Living Room/Dining Room Combo
Primarybedroom Upstairs
Solid Wood Cabinets
Stone Counters
Thermostat
Walk-in Closet(s)
Balcony
Courtyard
Sidewalks
Built-in Oven
Cooktop
Dishwasher
Microwave
Range
Refrigerator
Elementary
Audubon Park K8
Middle
Audubon Park K-8
High
Winter Park High

Districts can re-zone, so verify directly with the district before relying on these.

Flood Zone X
Annual Tax (2025)
$20,039
Parcel #
06-22-30-9670-00-311

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Winter Park Residential
County
Orange
MLS Area
32789 - Winter Park
HOA
$1,302.65/mo
Dominion Mgmt Solutions/Fernando

Price history

Date
Event
Price
9/9/2026
Price change
Source: Stellar MLS #O6416927
$1,775,000-4.0%
$570/sqft
6/17/2026
Listed for sale
Source: Stellar MLS #O6416927
$1,849,900
$594/sqft

Neighborhood

101 S New York Ave #311
Winter Park, FL, 32789 · 32789 - Winter Park

Market insights

Offer Insights

Choose an offer strength

List price: $1,775,000
$1.72M – $1.77M
96.9% – 100% of listTops out right at the list price
80% of listList price
26 of the last 51 condo closings in 32789 landed at this number or higher (51%). The median one sat 60 days before it went under contract, and this one is on day 115 after a $74,900 cut.

Sample: 51 closed condo sales in 32789 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

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Calculator

Est. monthly payment
$13,117/mo
Principal & interest$9,257
Property taxes$1,670
Insurance$888
HOA$1,303
Down payment20% · $355,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA is the fee reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$1,775,000

$570 per sq ft

Beds and baths

3 beds, 4 baths

Size

3,112 sq ft

Time on market

115 days

Year built

2008

Monthly payment

About $13,117/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $20,039 annual tax bill, insurance, and the $1,302.65/mo HOA fee.

HOA fee

$1,302.65/mo

Managed by Dominion Mgmt Solutions/Fernando.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

Have another question?

Brokered byKELLY PRICE & COMPANY LLCListing agent: Tiffany GrindstaffListing data from Stellar MLS, MLS# O6416927.

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