101 S NEW YORK AVENUE UNIT 311, WINTER PARK, FL, 32789
Active56 days on marketListed Jun 17, 2026MLS #O6416927
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Upcoming open house
Sun, Aug 16
2:00 PM – 4:00 PM
About this home
101 S NEW YORK AVENUE UNIT 311
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).
Facts & features
The home at a glance
3
Bedrooms
3.5
Bathrooms
3,112
Sqft
2
Garage
2008
Year built
Two
Levels
$594
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$13,809 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$13,809/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
$/sqft vs Winter Park actives
$594 vs $343
Days on market
56 vs 46 typical
Where $594/sqft sits among the 315 Winter Park actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Farmers' Market
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Farmers' Market — neighborhood snapshot
Population
370
Median age
28
Median income
$70,870
Median home value
$613,700
Avg household
2
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Park market
$470K → $512K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
144 of 315
Winter Park actives have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 123% above the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 101 S NEW YORK AVENUE UNIT 311
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’25$1,640,000
101 S NEW YORK AVENUE UNIT 313 · same community
3 bd · 3.5 ba · 3,147 sqft · $521/sqft · 3 DOM
Sold · May ’26$1,000,000
101 S NEW YORK AVENUE UNIT 302 · same community
3 bd · 3.5 ba · 3,174 sqft · $315/sqft · 36 DOM
Sold · Sep ’25$1,079,000
100 S VIRGINIA AVENUE UNIT 319 · same community
3 bd · 3 ba · 2,649 sqft · $407/sqft · 2 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 101 S NEW YORK AVENUE UNIT 311 — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 101 S NEW YORK AVENUE UNIT 311 — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
101 S NEW YORK AVENUE UNIT 311 FAQs
What would the monthly payment be for 101 S NEW YORK AVENUE UNIT 311?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $13,809/mo — principal and interest, the actual property-tax bill, the $1,303/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 101 S NEW YORK AVENUE UNIT 311?+
The association fee works out to $1,303 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 101 S NEW YORK AVENUE UNIT 311?+
The most recent tax bill on record (2025) was $20,039. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 101 S NEW YORK AVENUE UNIT 311?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Park?+
At $1,849,900, this home is listed about 209% above the Winter Park median of $599,000. The market section on this page shows how the area is trending.
Which schools are assigned to 101 S NEW YORK AVENUE UNIT 311?+
Audubon Park School (elementary), Winter Park High (high) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$1,849,900 runs 123% above the WINTER PARK 32789 median — but at 3,112 sqft it's also 74% larger than the typical Winter Park listing.
02City & Park/Greenbelt views
The city and park/greenbelt view is part of what you're buying — views hold value independently of the structure.
03Know the monthly fee
The association fee is $1,303/mo. That usually buys real services — verify what's covered before comparing this home against fee-free alternatives.
04Strong assigned schools
Audubon Park School, Winter Park High — Audubon Park School rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of KELLY PRICE & COMPANY LLC · Tiffany Grindstaff. MLS #O6416927.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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