# 101 S NEW YORK Avenue #311, Winter Park, FL 32789 > **TL;DR:** 3bd/4ba condo, $1,775,000 ($570/sqft), built 2008, 3,112 sqft. > View, A/C, RV Parking, 2-car garage. Est. $9,493/mo. Listed 133 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,775,000 | | Price/sqft | $570 | | Bedrooms | 3 | | Bathrooms | 3 full, 1 half | | Square Feet | 3,112 | | Year Built | 2008 | | Stories | 2 | | Garage | 2-car | | Property Type | Condo (Condominium) | | Status | Active | | Days on Market | 133 | ## Why This Home Stands Out - **Views** - City, Park ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $8,975 | | Estimated Insurance | $518 | | **Total** | **$9,493** | ## Nearby Schools - **Elementary:** Audubon Park K8 - **Middle:** Audubon Park K-8 - **High:** Winter Park High ## Key Amenities - View - A/C - RV Parking - 2-car garage ## Property Highlights - Built in 2008 - 2 stories ## Description ### Agent 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 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 - **Address:** 101 S NEW YORK Avenue #311, Winter Park, FL 32789 - **County:** Orange - **Neighborhood:** WINTER PARK RESIDENTIAL - **Coordinates:** 28.597448, -81.3533 - **Google Maps:** https://www.google.com/maps?q=28.597448,-81.3533 ## Virtual Tour & Media - **Video Tour:** https://www.youtube.com/watch?v=LLZx5FML7gA ## Listing Agent - **Name:** Tiffany Grindstaff - **Brokerage:** Kelly Price & Company - **Broker Phone:** (407) 645-4321 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/101-S-New-York-Ave-Unit-311_Winter-Park_FL_32789_M50492-40147?f=listhub&s=MFRMLSFL&m=O6416927&c=propsimple) ## Photos ![101 S NEW YORK Avenue #311 - Photo 1](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f1719423077r.jpg) ![101 S NEW YORK Avenue #311 - Photo 2](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f2415179630r.jpg) ![101 S NEW YORK Avenue #311 - Photo 3](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f347564236r.jpg) ![101 S NEW YORK Avenue #311 - Photo 4](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f3347920524r.jpg) ![101 S NEW YORK Avenue #311 - Photo 5](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f2105948717r.jpg) ![101 S NEW YORK Avenue #311 - Photo 6](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f1115395589r.jpg) ![101 S NEW YORK Avenue #311 - Photo 7](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f2000296803r.jpg) ![101 S NEW YORK Avenue #311 - Photo 8](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f1300781536r.jpg) ![101 S NEW YORK Avenue #311 - Photo 9](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f269855634r.jpg) ![101 S NEW YORK Avenue #311 - Photo 10](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f1361844457r.jpg) ![101 S NEW YORK Avenue #311 - Photo 11](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f438191953r.jpg) ![101 S NEW YORK Avenue #311 - Photo 12](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f2046627207r.jpg) ![101 S NEW YORK Avenue #311 - Photo 13](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f38284168r.jpg) ![101 S NEW YORK Avenue #311 - Photo 14](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f2506593913r.jpg) ![101 S NEW YORK Avenue #311 - Photo 15](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f722141533r.jpg) ![101 S NEW YORK Avenue #311 - Photo 16](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f3866738128r.jpg) ![101 S NEW YORK Avenue #311 - Photo 17](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f513335489r.jpg) ![101 S NEW YORK Avenue #311 - Photo 18](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f2620650853r.jpg) ![101 S NEW YORK Avenue #311 - Photo 19](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f665706737r.jpg) ![101 S NEW YORK Avenue #311 - Photo 20](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f3334881199r.jpg) ![101 S NEW YORK Avenue #311 - Photo 21](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f23247451r.jpg) ![101 S NEW YORK Avenue #311 - Photo 22](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f2437182200r.jpg) ![101 S NEW YORK Avenue #311 - Photo 23](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f1815564060r.jpg) ![101 S NEW YORK Avenue #311 - Photo 24](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f3201640686r.jpg) ![101 S NEW YORK Avenue #311 - Photo 25](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f1844285056r.jpg) ![101 S NEW YORK Avenue #311 - Photo 26](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f864550456r.jpg) ![101 S NEW YORK Avenue #311 - Photo 27](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f1920386381r.jpg) ![101 S NEW YORK Avenue #311 - Photo 28](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f2259731298r.jpg) ![101 S NEW YORK Avenue #311 - Photo 29](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f2019442353r.jpg) ![101 S NEW YORK Avenue #311 - Photo 30](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f2013871687r.jpg) ![101 S NEW YORK Avenue #311 - Photo 31](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f3068661953r.jpg) ![101 S NEW YORK Avenue #311 - Photo 32](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f3437131460r.jpg) ![101 S NEW YORK Avenue #311 - Photo 33](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f4095216247r.jpg) ![101 S NEW YORK Avenue #311 - Photo 34](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f1950074264r.jpg) ![101 S NEW YORK Avenue #311 - Photo 35](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f843493564r.jpg) ![101 S NEW YORK Avenue #311 - Photo 36](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f124510248r.jpg) ![101 S NEW YORK Avenue #311 - Photo 37](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f3739814940r.jpg) ![101 S NEW YORK Avenue #311 - Photo 38](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f3777901753r.jpg) ![101 S NEW YORK Avenue #311 - Photo 39](http://lh.rdcpix.com/e73987905e65d1dffd1254b001cf3fc5l-f4148839256r.jpg) --- **MLS#:** O6416927 | **Updated:** 2026-10-25 **Source:** listhub *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.* [View on PropertySimple](https://staging.propertysimple.ai/listing/101-s-new-york-avenue-winter-park-fl-32789-c8ab041784bf488e9a1e2da19df69db4) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/101-s-new-york-avenue-winter-park-fl-32789-c8ab041784bf488e9a1e2da19df69db4#listing", "url": "https://staging.propertysimple.ai/listing/101-s-new-york-avenue-winter-park-fl-32789-c8ab041784bf488e9a1e2da19df69db4", "name": "101 S NEW YORK Avenue #311, Winter Park, FL 32789", "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 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. 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