# 1621 CHESTNUT Avenue, Winter Park, FL 32789 > **TL;DR:** 3bd/3ba single family, $879,000 ($435/sqft), built 1970, 2,022 sqft. > A/C, 2-car garage. Est. $4,701/mo. Listed 69 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $879,000 | | Price/sqft | $435 | | Bedrooms | 3 | | Bathrooms | 2 full, 1 half | | Square Feet | 2,022 | | Year Built | 1970 | | Lot Size | 7,405 sqft (0.17 acres) | | Stories | 1 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 69 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $4,445 | | Estimated Insurance | $256 | | **Total** | **$4,701** | ## Nearby Schools - **Elementary:** Lakemont Elem - **Middle:** Maitland Middle - **High:** Winter Park High ## Key Amenities - A/C - 2-car garage ## Property Highlights - Built in 1970 - 0.17 acre lot ## Description ### Agent Description Welcome to 1621 Chestnut Avenue, ideally situated in the heart of Winter Park's coveted "Tree Streets" neighborhood. Offered at $879,000, this single-story block home sits on a generous 50x150' lot and offers 2,022 square feet of living space with 3 bedrooms and 2.5 baths. Whether you envision a thoughtful remodel or a ground-up new build, this property presents outstanding potential in one of Winter Park's most desirable pockets, where similar transformations are already reshaping the streetscape. Inside, tile flooring flows through the main living areas, complementing a versatile layout that includes a formal living room, a combined kitchen and dining area, and a separate den with pocket doors perfect for a home office or media room. The oversized bedrooms offer generous space throughout, including a primary suite with a private en suite bath. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, ideal for family or guests. At the rear of the home, an enclosed sunroom provides a peaceful retreat overlooking the well-manicured backyard, a tranquil spot to relax and unwind. With its prime location, solid bones, and abundant possibilities, 1621 Chestnut Avenue is ready for its next owner to make it their own. ## Location - **Address:** 1621 CHESTNUT Avenue, Winter Park, FL 32789 - **County:** Orange - **Neighborhood:** LAKE KNOWLES TERRACE - **Coordinates:** 28.613892, -81.331749 - **Google Maps:** https://www.google.com/maps?q=28.613892,-81.331749 ## Virtual Tour & Media - **Video Tour:** https://www.youtube.com/watch?v=gbE-y9DtFW8 ## Listing Agent - **Name:** Kelly Price - **Brokerage:** Kelly Price & Company - **Broker Phone:** (407) 645-4321 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/1621-Chestnut-Ave_Winter-Park_FL_32789_M67451-68098?f=listhub&s=MFRMLSFL&m=O6435086&c=propsimple) ## Photos ![1621 CHESTNUT Avenue - Photo 1](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f1873851936r.jpg) ![1621 CHESTNUT Avenue - Photo 2](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f1488484465r.jpg) ![1621 CHESTNUT Avenue - Photo 3](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f4294186763r.jpg) ![1621 CHESTNUT Avenue - Photo 4](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f3824778619r.jpg) ![1621 CHESTNUT Avenue - Photo 5](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f119208030r.jpg) ![1621 CHESTNUT Avenue - Photo 6](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f1161529249r.jpg) ![1621 CHESTNUT Avenue - Photo 7](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f3444309151r.jpg) ![1621 CHESTNUT Avenue - Photo 8](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f2437458726r.jpg) ![1621 CHESTNUT Avenue - Photo 9](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f666530777r.jpg) ![1621 CHESTNUT Avenue - Photo 10](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f416789443r.jpg) ![1621 CHESTNUT Avenue - Photo 11](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f2505627465r.jpg) ![1621 CHESTNUT Avenue - Photo 12](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f871685229r.jpg) ![1621 CHESTNUT Avenue - Photo 13](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f4253949967r.jpg) ![1621 CHESTNUT Avenue - Photo 14](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f2412346805r.jpg) ![1621 CHESTNUT Avenue - Photo 15](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f518307051r.jpg) ![1621 CHESTNUT Avenue - Photo 16](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f1176041776r.jpg) ![1621 CHESTNUT Avenue - Photo 17](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f1119848157r.jpg) ![1621 CHESTNUT Avenue - Photo 18](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f4139780322r.jpg) ![1621 CHESTNUT Avenue - Photo 19](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f3888775263r.jpg) ![1621 CHESTNUT Avenue - Photo 20](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f2083389892r.jpg) ![1621 CHESTNUT Avenue - Photo 21](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f3257644667r.jpg) ![1621 CHESTNUT Avenue - Photo 22](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f1723649783r.jpg) ![1621 CHESTNUT Avenue - Photo 23](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f3033312254r.jpg) ![1621 CHESTNUT Avenue - Photo 24](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f3199356221r.jpg) ![1621 CHESTNUT Avenue - Photo 25](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f3736000879r.jpg) ![1621 CHESTNUT Avenue - Photo 26](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f1913314354r.jpg) ![1621 CHESTNUT Avenue - Photo 27](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f270167108r.jpg) ![1621 CHESTNUT Avenue - Photo 28](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f1131016081r.jpg) ![1621 CHESTNUT Avenue - Photo 29](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f1683391921r.jpg) ![1621 CHESTNUT Avenue - Photo 30](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f1482812506r.jpg) ![1621 CHESTNUT Avenue - Photo 31](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f4272369103r.jpg) ![1621 CHESTNUT Avenue - Photo 32](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f1410055230r.jpg) ![1621 CHESTNUT Avenue - Photo 33](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f313868569r.jpg) ![1621 CHESTNUT Avenue - Photo 34](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f3640869881r.jpg) ![1621 CHESTNUT Avenue - Photo 35](http://lh.rdcpix.com/fa70e2ee9db3837b63fe5aae06e1a189l-f1201100696r.jpg) --- **MLS#:** O6435086 | **Updated:** 2026-10-27 **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/1621-chestnut-avenue-winter-park-fl-32789-aba8639e01d44a13bd1b49fec4a5fa60) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/1621-chestnut-avenue-winter-park-fl-32789-aba8639e01d44a13bd1b49fec4a5fa60#listing", "url": "https://staging.propertysimple.ai/listing/1621-chestnut-avenue-winter-park-fl-32789-aba8639e01d44a13bd1b49fec4a5fa60", "name": "1621 CHESTNUT Avenue, Winter Park, FL 32789", "description": "Welcome to 1621 Chestnut Avenue, ideally situated in the heart of Winter Park's coveted \"Tree Streets\" neighborhood. 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