Love Life
Contact Dennis Dial
Contacting Dennis Dial
  • All fields are required.
Schedule A Showing
Schedule a Showing.
  • All fields are required.
Check this box to Register with us:
Submit an Offer Now!
Submit an Offer Now!
All fields are required.
Print Flyer
1521 Chestnut Avenue, Winter Park, FL 32789
  1. Image 1 For 1521 Chestnut Avenue
  2. Image 2 For 1521 Chestnut Avenue
  3. Image 3 For 1521 Chestnut Avenue
  4. Image 4 For 1521 Chestnut Avenue
  5. Image 5 For 1521 Chestnut Avenue
  6. Image 6 For 1521 Chestnut Avenue
  7. Image 7 For 1521 Chestnut Avenue
  8. Image 8 For 1521 Chestnut Avenue
  9. Image 9 For 1521 Chestnut Avenue
  10. Image 10 For 1521 Chestnut Avenue
  11. Image 11 For 1521 Chestnut Avenue
  12. Image 12 For 1521 Chestnut Avenue
  13. Image 13 For 1521 Chestnut Avenue
  14. Image 14 For 1521 Chestnut Avenue
  15. Image 15 For 1521 Chestnut Avenue
  16. Image 16 For 1521 Chestnut Avenue
  17. Image 17 For 1521 Chestnut Avenue
  18. Image 18 For 1521 Chestnut Avenue
  19. Image 19 For 1521 Chestnut Avenue
  20. Image 20 For 1521 Chestnut Avenue
  21. Image 21 For 1521 Chestnut Avenue
  22. Image 22 For 1521 Chestnut Avenue
  23. Image 23 For 1521 Chestnut Avenue
  24. Image 24 For 1521 Chestnut Avenue
  25. Image 25 For 1521 Chestnut Avenue
  26. Image 26 For 1521 Chestnut Avenue
  27. Image 27 For 1521 Chestnut Avenue
  28. Image 28 For 1521 Chestnut Avenue
  29. Image 29 For 1521 Chestnut Avenue
  30. Image 30 For 1521 Chestnut Avenue
  31. Image 31 For 1521 Chestnut Avenue
  32. Image 32 For 1521 Chestnut Avenue
  33. Image 33 For 1521 Chestnut Avenue
  34. Image 34 For 1521 Chestnut Avenue
  35. Image 35 For 1521 Chestnut Avenue
  36. Image 36 For 1521 Chestnut Avenue
  37. Image 37 For 1521 Chestnut Avenue
  38. Image 38 For 1521 Chestnut Avenue
  39. Image 39 For 1521 Chestnut Avenue
  40. Image 40 For 1521 Chestnut Avenue
  41. Image 41 For 1521 Chestnut Avenue
  42. Image 42 For 1521 Chestnut Avenue
  43. Image 43 For 1521 Chestnut Avenue
  44. Image 44 For 1521 Chestnut Avenue
  45. Image 45 For 1521 Chestnut Avenue
  46. Image 46 For 1521 Chestnut Avenue
  47. Image 47 For 1521 Chestnut Avenue
  48. Image 48 For 1521 Chestnut Avenue
  49. Image 49 For 1521 Chestnut Avenue
  50. Image 50 For 1521 Chestnut Avenue
  51. Image 51 For 1521 Chestnut Avenue
  52. Image 52 For 1521 Chestnut Avenue
  53. Image 53 For 1521 Chestnut Avenue
  54. Image 54 For 1521 Chestnut Avenue
  55. Image 55 For 1521 Chestnut Avenue
Property Photos
1521 Chestnut Avenue
Image Gallery
Would you like to sell your home before you purchase this one?
Priced at Only: $1,999,900
For more Information Call:
Address: 1521 Chestnut Avenue, Winter Park, FL 32789
Property Location and Similar Properties
All
Similar
  1. Image 1 For 1521 Chestnut Avenue
  2. Image 2 For 1521 Chestnut Avenue
  3. Image 3 For 1521 Chestnut Avenue
  4. Image 4 For 1521 Chestnut Avenue
  5. Image 5 For 1521 Chestnut Avenue
  6. Image 6 For 1521 Chestnut Avenue
  7. Image 7 For 1521 Chestnut Avenue
  8. Image 8 For 1521 Chestnut Avenue
  9. Image 9 For 1521 Chestnut Avenue
  10. Image 10 For 1521 Chestnut Avenue
  11. Image 11 For 1521 Chestnut Avenue
  12. Image 12 For 1521 Chestnut Avenue
  13. Image 13 For 1521 Chestnut Avenue
  14. Image 14 For 1521 Chestnut Avenue
  15. Image 15 For 1521 Chestnut Avenue
  16. Image 16 For 1521 Chestnut Avenue
  17. Image 17 For 1521 Chestnut Avenue
  18. Image 18 For 1521 Chestnut Avenue
  19. Image 19 For 1521 Chestnut Avenue
  20. Image 20 For 1521 Chestnut Avenue
  21. Image 21 For 1521 Chestnut Avenue
  22. Image 22 For 1521 Chestnut Avenue
  23. Image 23 For 1521 Chestnut Avenue
  24. Image 24 For 1521 Chestnut Avenue
  25. Image 25 For 1521 Chestnut Avenue
  26. Image 26 For 1521 Chestnut Avenue
  27. Image 27 For 1521 Chestnut Avenue
  28. Image 28 For 1521 Chestnut Avenue
  29. Image 29 For 1521 Chestnut Avenue
  30. Image 30 For 1521 Chestnut Avenue
  31. Image 31 For 1521 Chestnut Avenue
  32. Image 32 For 1521 Chestnut Avenue
  33. Image 33 For 1521 Chestnut Avenue
  34. Image 34 For 1521 Chestnut Avenue
  35. Image 35 For 1521 Chestnut Avenue
  36. Image 36 For 1521 Chestnut Avenue
  37. Image 37 For 1521 Chestnut Avenue
  38. Image 38 For 1521 Chestnut Avenue
  39. Image 39 For 1521 Chestnut Avenue
  40. Image 40 For 1521 Chestnut Avenue
  41. Image 41 For 1521 Chestnut Avenue
  42. Image 42 For 1521 Chestnut Avenue
  43. Image 43 For 1521 Chestnut Avenue
  44. Image 44 For 1521 Chestnut Avenue
  45. Image 45 For 1521 Chestnut Avenue
  46. Image 46 For 1521 Chestnut Avenue
  47. Image 47 For 1521 Chestnut Avenue
  48. Image 48 For 1521 Chestnut Avenue
  49. Image 49 For 1521 Chestnut Avenue
  50. Image 50 For 1521 Chestnut Avenue
  51. Image 51 For 1521 Chestnut Avenue
  52. Image 52 For 1521 Chestnut Avenue
  53. Image 53 For 1521 Chestnut Avenue
  54. Image 54 For 1521 Chestnut Avenue
  55. Image 55 For 1521 Chestnut Avenue
Request More Information
  • All fields are required.
Virtual Tour
More Like This
  • MLS#: A4651868 ( Residential )
  • Street Address: 1521 Chestnut Avenue
  • Viewed: 6
  • Price: $1,999,900
  • Price sqft: $540
  • Waterfront: No
  • Year Built: 2022
  • Bldg sqft: 3703
  • Bedrooms: 4
  • Total Baths: 3
  • Full Baths: 3
  • Days On Market: 15
  • Additional Information
  • Geolocation: 28.6139 / -81.3332
  • County: ORANGE
  • City: Winter Park
  • Zipcode: 32789
  • Subdivision: Lake Knowles Terrace
  • Elementary School: Lakemont Elem
  • Middle School: Maitland
  • High School: Winter Park
  • Provided by: COMPASS FLORIDA LLC
  • DMCA Notice
  • Description
    Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, built in 2023, located in one of Winter Parks most sought after neighborhoods. Designed with sleek sophistication and functional elegance, this fabulous home offers 4 bedrooms, 3 full baths, and a flexible layout perfect for todays lifestyle. The open concept main floor features a beautifully appointed kitchen, a spacious dining area, and a light filled living room complete with a designer fireplace and custom built in shelving. The stunning kitchen boasts quartz counters, spacious cabinetry, KitchenAid appliances, and designer lighting. A fourth bedroom (currently used as a study) is also located on the main level, along with an oversized bonus room. From the great room, expansive sliding glass doors lead out to the covered lanai, where you'll find an inground pool, a fully fenced yard, tongue in groove wood ceiling, and pre plumbing in place for your dream summer kitchenideal for entertaining year round. Upstairs, the luxurious primary suite provides a peaceful retreat with an oversized balcony overlooking the pool and rear yard. Two additional bedrooms are also featured on the second level, along with a second full bath. The first floor office doubles as a fourth bedroom, with an adjacent full bath for guests or multigenerational living. The original two car garage has been converted into a 425 sq ft air conditioned bonus roomperfect as a media room, home gym, or additional living space. This home boasts well thought out upgrades, including beautiful wood inlays in niches, open shelving, quartz countertops, slat wall features, and stunning light fixtures throughout. The work has been done for you in this like new home! Located just steps from Phelps Park, and minutes from the shops and dining of Park Avenue and the Winter Park Chain of Lakes, this home offers the perfect blend of modern design, comfort, and convenience. Don't miss your chance to own this exceptional home in the heart of Winter Park!
Payment Calculator
  •   Principal & Interest -
  •   Property Tax $
  •   Home Insurance $
  •   HOA Fees $
  •   Mortgage Insurance-
  •   Monthly -
For a Fast & FREE Mortgage Pre-ApprovalApply Now
Features
Building and Construction
  • Covered Spaces: 0.00
  • Exterior Features: Balcony, SprinklerIrrigation, Lighting
  • Fencing: Wood
  • Flooring: PorcelainTile
  • Living Area: 3117.00
  • Roof: Shingle
Land Information
  • Lot Features: Private
School Information
  • High School: Winter Park High
  • Middle School: Maitland Middle
  • School Elementary: Lakemont Elem
Garage and Parking
  • Garage Spaces: 0.00
  • Open Parking Spaces: 0.00
Eco-Communities
  • Pool Features: Gunite, InGround
  • Water Source: Public
Utilities
  • Carport Spaces: 0.00
  • Cooling: CentralAir, Ductless, Zoned, CeilingFans
  • Heating: Central, HeatPump, Zoned
  • Sewer: PublicSewer
  • Utilities: CableConnected, ElectricityConnected, HighSpeedInternetAvailable, Propane, SewerConnected, WaterConnected
Finance and Tax Information
  • Home Owners Association Fee: 0.00
  • Insurance Expense: 0.00
  • Net Operating Income: 0.00
  • Other Expense: 0.00
  • Pet Deposit: 0.00
  • Security Deposit: 0.00
  • Tax Year: 2024
  • Trash Expense: 0.00
Other Features
  • Appliances: BuiltInOven, Dishwasher, ExhaustFan, Microwave, Refrigerator, TanklessWaterHeater
  • Country: US
  • Interior Features: BuiltInFeatures, CeilingFans, HighCeilings, KitchenFamilyRoomCombo, OpenFloorplan, SolidSurfaceCounters, UpperLevelPrimary, WalkInClosets
  • Legal Description: LAKE KNOWLES TERRACE K/4 LOT 18 BLK 1
  • Levels: Two
  • Area Major: 32789 - Winter Park
  • Occupant Type: Owner
  • Parcel Number: 32-21-30-4536-01-180
  • Possession: CloseOfEscrow
  • Style: MidCenturyModern
  • The Range: 0.00
  • Zoning Code: R-1A
Similar Properties

Details for 2260 Mulbry Drive, WINTER PARK, FL 32789
$2,000,000.00 ($502.51 / sqft )

2260 Mulbry Drive New Construction More Like This

Pre Construction. To be built. Your Dream Home Is Ready To Be Built! Pre Construction Opportunity! Build to Suit! Build your custom dream home with renowned Konkol Homes in one of Central Floridas mos

  1. Request Information
  1. Bedrooms: 5
  2. Baths: 4
  3. Approx. 3980 sqft
  1. MLSID: O6264761
  2. Provided by KELLER WILLIAMS WINTER PARK
  3. Contact Farah Bloom
  4. mfrmls
  5. DMCA Notice
4 Pictures and Information
Details for 785 Phelps Avenue, WINTER PARK, FL 32789
$2,119,000.00 ($537.68 / sqft )

785 Phelps Avenue Virtual Tour New Construction More Like This

Under Construction. Completion September 2025, Nestled in the heart of Winter Park, this luxurious custom built home seamlessly blends elegance, functionality, and thoughtful design. Boasting 5 bedroo

  1. Request Information
  1. Bedrooms: 5
  2. Baths: 5
  3. Approx. 3941 sqft
  1. MLSID: O6275847
  2. Provided by COMPASS FLORIDA LLC
  3. Contact Leighton Hope
  4. mfrmls
  5. DMCA Notice
10 Pictures and Information
Details for 2614 Parkland Drive, WINTER PARK, FL 32789
$2,249,999.00 ($488.07 / sqft )

2614 Parkland Drive Virtual Tour More Like This

Welcome to 2614 Parkland Drivean exquisite, fully renovated luxury residence nestled in the heart of Winter Park, Florida, one of the most coveted locations in all of Central Florida. Zoned for the hi

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 4
  3. Approx. 4610 sqft
  1. MLSID: O6301489
  2. Provided by JW GASTON LLC
  3. Contact Ryan Gaston
  4. mfrmls
  5. DMCA Notice
77 Pictures and Information
Details for 1840 Bryan Avenue, WINTER PARK, FL 32789
$1,999,500.00 ($428.62 / sqft )

1840 Bryan Avenue Virtual Tour Reduced More Like This

This custom 2014 built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all that Winter Park offers. A home with function and flexibility with a s

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 4
  3. Approx. 4665 sqft
  1. MLSID: O6304239
  2. Provided by PREMIER SOTHEBY'S INTL. REALTY
  3. Contact Alison Mosley
  4. mfrmls
  5. DMCA Notice
47 Pictures and Information
Details for 301 Rippling Lane, WINTER PARK, FL 32789
$2,349,900.00 ($462.76 / sqft )

301 Rippling Lane Virtual Tour More Like This

Nestled along the serene shores of Lake Killarney, one of Winter Park's best kept secrets Lake Killarney is one of Winter Park's largest freshwater spring fed lakes (240 acres) this stunning lakefront

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 6
  3. Approx. 5078 sqft
  1. MLSID: A4637563
  2. Provided by XCLUSIVE HOMES LLC
  3. Contact Cynthia Fernandez
  4. mfrmls
  5. DMCA Notice
43 Pictures and Information
Details for 2412 Chantilly Avenue, WINTER PARK, FL 32789
$2,389,000.00 ($459.78 / sqft )

2412 Chantilly Avenue New Construction More Like This

Step into a realm of refined livingan architectural tour de force in the heart of Winter Park. Designed by a premier boutique builder and meticulously crafted with no detail spared, this 5 bedroom, 6.

  1. Request Information
  1. Bedrooms: 5
  2. Baths: 7
  3. Approx. 5196 sqft
  1. MLSID: O6278049
  2. Provided by COMPASS FLORIDA LLC
  3. Contact Ahmad Hassan, PA
  4. mfrmls
  5. DMCA Notice
84 Pictures and Information
Details for 1560 Woodland Avenue, WINTER PARK, FL 32789
$2,150,000.00 ($414.66 / sqft )

1560 Woodland Avenue Virtual Tour More Like This

You have arrived to 1560 Woodland Avenue, a beautiful home in a prime location inside the Winter Park municipality, situated on a peaceful brick paved street. There are five bedrooms and four and a ha

  1. Request Information
  1. Bedrooms: 5
  2. Baths: 5
  3. Approx. 5185 sqft
  1. MLSID: O6293517
  2. Provided by LOKATION
  3. Contact Manny Alvarez
  4. mfrmls
  5. DMCA Notice
48 Pictures and Information
Details for 1299 Harding Street, WINTER PARK, FL 32789
$1,899,999.00 ($439.21 / sqft )

1299 Harding Street Virtual Tour Reduced More Like This

Welcome to your private slice of paradisea beautifully renovated home with a brand new 2024 pied terre guest retreat, nestled just steps from the iconic Kraft Azalea Garden on the shores of Lake Mait

  1. Request Information
  1. Bedrooms: 6
  2. Baths: 5
  3. Approx. 4326 sqft
  1. MLSID: O6298410
  2. Provided by FANNIE HILLMAN & ASSOCIATES
  3. Contact Nancy Bagby
  4. mfrmls
  5. DMCA Notice
53 Pictures and Information
Details for 1361 Palmer Ave., WINTER PARK, FL 32789
$2,349,000.00 ($545.27 / sqft )

1361 Palmer Ave. Virtual Tour More Like This

One or more photo(s) has been virtually staged. Welcome to 1361 Palmer Avenue, a beautifully updated five bedroom, 3.5 bath residence in the heart of Winter Park, Florida, 32789. This exceptional home

  1. Request Information
  1. Bedrooms: 5
  2. Baths: 4
  3. Approx. 4308 sqft
  1. MLSID: O6311013
  2. Provided by PREMIER SOTHEBY'S INTL. REALTY
  3. Contact Michelle Hochfelder
  4. mfrmls
  5. DMCA Notice
43 Pictures and Information
Details for 1665 Temple Drive, WINTER PARK, FL 32789
$1,899,000.00 ($391.63 / sqft )

1665 Temple Drive Virtual Tour More Like This

A rare gem in the heart of the Vias Nestled in one of Winter Parks most sought after neighborhoods, this beautifully designed home is the epitome of comfort, luxury, and convenience. Located just min

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 4
  3. Approx. 4849 sqft
  1. MLSID: O6300797
  2. Provided by COMPASS FLORIDA LLC
  3. Contact Brandon Geers
  4. mfrmls
  5. DMCA Notice
58 Pictures and Information
Nearby Subdivisions
Acreage   Albert Lee Ridge First Add   Banks Colonial Estates   Camwood Sub   Canton Ave Cottages 1   Carver Town First Add   Charmont   College Place Rep   Comstock Park   Conwill Estates   Cortland Park   Dixie Terrace   Dommerich Estates   Dommerich Hills   Dommerich Hills Fourth Add   Dubsdread Heights   Ellno Willo   Fairbanks Shores 4th Add   Fairbanks Shores 5th Add   Flamingo Shores   Flora Park First Add   Fontainebleau   Forest Hills   Galloway Place Rep   Glencoe Sub   Golfview   Golfview Heights   Henkel Add   Howell Forest   J Kronenberger   J Kronenberger Sub   Jenkins Add   Karolina On Killarney   Kenilworth Shores Sec 01   Kenilworth Shores Sec 02   Kenilworth Shores Sec 06   Killarney Estates   Lake Forest Park   Lake Killarney Shores   Lake Knowles Terrace   Lake Monte Sub   Lakeview Terrace   Lawndale   Lords Sub   Lugano Terrace   Maitland Shores First Add   Morseland Sub   Northwood Terrace   Olympia Heights   Orwin Manor Westminster Sec   Osceola Shores Sec 03   Park Grove   Park North   Parklando 03   Pennsylvania Place Rep   Robert Dhu Macdonald Park   Sevilla   Shores Lake Killarney Sec 02   South Lakemont Shores   Stansbury Estates   Stonehurst Estates   Sylvan Heights   Sylvan Lake Shores   Temple Heights   Timberlane   Timberlane Shores   Trotters Rep   Tuscania   Tuscany Terrace   V H Musselwhites Sub   Virginia Heights   Virginia Heights Rep   Waterbridge   Windsong   Windsong Lakeside Sec 01 4370   Windsong Preserve Point 43/76   Windsong Preserve Point 4376   Windsongpreserve Point   Winter Park   Winter Park Heights   Winter Park Oaks   Winter Park Village   Woodmere Terrace Rep  
Skip to Main Content
Headshot for Associate Dennis Dial
  1. The Dial Team
  2. Tropic Shores Realty
  3. Love Life
  4. Mobile: 561.201.4476
  5. dennisdialsells@gmail.com