MENU
Contact Trudi Geniale
Schedule A Showing
Submit an Offer Now!
Print Flyer
1585 Chestnut Avenue, WINTER PARK, FL 32789
  1. Image 1 of 45 For 1585 Chestnut Avenue
  2. Image 2 of 45 For 1585 Chestnut Avenue
  3. Image 3 of 45 For 1585 Chestnut Avenue
  4. Image 4 of 45 For 1585 Chestnut Avenue
  5. Image 5 of 45 For 1585 Chestnut Avenue
  6. Image 6 of 45 For 1585 Chestnut Avenue
  7. Image 7 of 45 For 1585 Chestnut Avenue
  8. Image 8 of 45 For 1585 Chestnut Avenue
  9. Image 9 of 45 For 1585 Chestnut Avenue
  10. Image 10 of 45 For 1585 Chestnut Avenue
  11. Image 11 of 45 For 1585 Chestnut Avenue
  12. Image 12 of 45 For 1585 Chestnut Avenue
  13. Image 13 of 45 For 1585 Chestnut Avenue
  14. Image 14 of 45 For 1585 Chestnut Avenue
  15. Image 15 of 45 For 1585 Chestnut Avenue
  16. Image 16 of 45 For 1585 Chestnut Avenue
  17. Image 17 of 45 For 1585 Chestnut Avenue
  18. Image 18 of 45 For 1585 Chestnut Avenue
  19. Image 19 of 45 For 1585 Chestnut Avenue
  20. Image 20 of 45 For 1585 Chestnut Avenue
  21. Image 21 of 45 For 1585 Chestnut Avenue
  22. Image 22 of 45 For 1585 Chestnut Avenue
  23. Image 23 of 45 For 1585 Chestnut Avenue
  24. Image 24 of 45 For 1585 Chestnut Avenue
  25. Image 25 of 45 For 1585 Chestnut Avenue
  26. Image 26 of 45 For 1585 Chestnut Avenue
  27. Image 27 of 45 For 1585 Chestnut Avenue
  28. Image 28 of 45 For 1585 Chestnut Avenue
  29. Image 29 of 45 For 1585 Chestnut Avenue
  30. Image 30 of 45 For 1585 Chestnut Avenue
  31. Image 31 of 45 For 1585 Chestnut Avenue
  32. Image 32 of 45 For 1585 Chestnut Avenue
  33. Image 33 of 45 For 1585 Chestnut Avenue
  34. Image 34 of 45 For 1585 Chestnut Avenue
  35. Image 35 of 45 For 1585 Chestnut Avenue
  36. Image 36 of 45 For 1585 Chestnut Avenue
  37. Image 37 of 45 For 1585 Chestnut Avenue
  38. Image 38 of 45 For 1585 Chestnut Avenue
  39. Image 39 of 45 For 1585 Chestnut Avenue
  40. Image 40 of 45 For 1585 Chestnut Avenue
  41. Image 41 of 45 For 1585 Chestnut Avenue
  42. Image 42 of 45 For 1585 Chestnut Avenue
  43. Image 43 of 45 For 1585 Chestnut Avenue
  44. Image 44 of 45 For 1585 Chestnut Avenue
  45. Image 45 of 45 For 1585 Chestnut Avenue
Property Photos
1585 Chestnut Avenue
Image Gallery
Would you like to sell your home before you purchase this one?
Priced at Only: $1,225,000
For more Information Call:
Address: 1585 Chestnut Avenue, WINTER PARK, FL 32789
Property Location and Similar Properties
All
Similar
  1. Image 1 of 45 For 1585 Chestnut Avenue
  2. Image 2 of 45 For 1585 Chestnut Avenue
  3. Image 3 of 45 For 1585 Chestnut Avenue
  4. Image 4 of 45 For 1585 Chestnut Avenue
  5. Image 5 of 45 For 1585 Chestnut Avenue
  6. Image 6 of 45 For 1585 Chestnut Avenue
  7. Image 7 of 45 For 1585 Chestnut Avenue
  8. Image 8 of 45 For 1585 Chestnut Avenue
  9. Image 9 of 45 For 1585 Chestnut Avenue
  10. Image 10 of 45 For 1585 Chestnut Avenue
  11. Image 11 of 45 For 1585 Chestnut Avenue
  12. Image 12 of 45 For 1585 Chestnut Avenue
  13. Image 13 of 45 For 1585 Chestnut Avenue
  14. Image 14 of 45 For 1585 Chestnut Avenue
  15. Image 15 of 45 For 1585 Chestnut Avenue
  16. Image 16 of 45 For 1585 Chestnut Avenue
  17. Image 17 of 45 For 1585 Chestnut Avenue
  18. Image 18 of 45 For 1585 Chestnut Avenue
  19. Image 19 of 45 For 1585 Chestnut Avenue
  20. Image 20 of 45 For 1585 Chestnut Avenue
  21. Image 21 of 45 For 1585 Chestnut Avenue
  22. Image 22 of 45 For 1585 Chestnut Avenue
  23. Image 23 of 45 For 1585 Chestnut Avenue
  24. Image 24 of 45 For 1585 Chestnut Avenue
  25. Image 25 of 45 For 1585 Chestnut Avenue
  26. Image 26 of 45 For 1585 Chestnut Avenue
  27. Image 27 of 45 For 1585 Chestnut Avenue
  28. Image 28 of 45 For 1585 Chestnut Avenue
  29. Image 29 of 45 For 1585 Chestnut Avenue
  30. Image 30 of 45 For 1585 Chestnut Avenue
  31. Image 31 of 45 For 1585 Chestnut Avenue
  32. Image 32 of 45 For 1585 Chestnut Avenue
  33. Image 33 of 45 For 1585 Chestnut Avenue
  34. Image 34 of 45 For 1585 Chestnut Avenue
  35. Image 35 of 45 For 1585 Chestnut Avenue
  36. Image 36 of 45 For 1585 Chestnut Avenue
  37. Image 37 of 45 For 1585 Chestnut Avenue
  38. Image 38 of 45 For 1585 Chestnut Avenue
  39. Image 39 of 45 For 1585 Chestnut Avenue
  40. Image 40 of 45 For 1585 Chestnut Avenue
  41. Image 41 of 45 For 1585 Chestnut Avenue
  42. Image 42 of 45 For 1585 Chestnut Avenue
  43. Image 43 of 45 For 1585 Chestnut Avenue
  44. Image 44 of 45 For 1585 Chestnut Avenue
  45. Image 45 of 45 For 1585 Chestnut Avenue
Request More Information
  • All fields are required.
  • Check this box if you are a real person:
Virtual Tour
Reduced
More Like This
  • MLS#: O6280166 ( Residential )
  • Street Address: 1585 Chestnut Avenue
  • Viewed: 71
  • Price: $1,225,000
  • Price sqft: $466
  • Waterfront: No
  • Year Built: 1959
  • Bldg sqft: 2631
  • Bedrooms: 4
  • Total Baths: 3
  • Full Baths: 2
  • 1/2 Baths: 1
  • Garage / Parking Spaces: 1
  • Days On Market: 38
Description
Charming Spanish Style Bungalow with Private Oasis in the Heart of Winter Park. Step into the elegance of Old Florida with this exquisite Spanish style bungalow, nestled in Winter Park. Offering the perfect blend of historic charm and modern luxury, this 4 bedroom, 2.5 bath retreat is a hidden gem surrounded by lush, mature landscaping, creating a private sanctuary just minutes from the best Winter Park has to offer. From the moment you arrive, youll be captivated by the stunning curb appeal, featured on the front cover of Home & Garden magazine. The beautifully maintained exterior, with its 2023 terracotta styled flat roof sets the stage for what lies within. Inside, timeless character meets contemporary upgrades. French terracotta flooring, antique hardware, and neutral warm tones create an inviting atmosphere, while thoughtful renovations ensure every modern convenience is at your fingertips. The kitchen is a chefs dream, boasting vanilla quartz countertops with gold flecks, beautifully complementing the bronze accents and upgraded appliances. The open concept design seamlessly connects the kitchen, dining, and living area ideal for entertaining. For more intimate gatherings, unwind in the spacious family room or soak in the natural light from the attached sunroom, which overlooks the lush backyard retreat. Step outside to a tranquil space perfect for morning coffee or evening cocktails, all while enjoying the peaceful sounds of nature. The pool and jacuzzi (new heater installed in 2021) add a touch of resort style living, surrounded by meticulously curated landscaping with extensive landscape lighting (2022) that enhances the homes enchanting ambiance. Situated in a vibrant, walkable neighborhood known for its tree lined streets and friendly atmosphere, this home is just a short stroll to Lake Knowles, the YMCA, and Phelps Park. Bring your golf cart and enjoy easy access to Interlachen Golf & Country Club or the Winter Park Racquet Club. Plus, youre less than a mile from the newly renovated Winter Park Hospital and just minutes from Park Ave world class dining and shopping. Top rated schools: Zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. This rare, character filled home offers a perfect blend of privacy, luxury, and location. Dont miss your chance to own a piece of Winter Parks most desirable neighborhood!
Description
Charming Spanish Style Bungalow with Private Oasis in the Heart of Winter Park. Step into the elegance of Old Florida with this exquisite Spanish style bungalow, nestled in Winter Park. Offering the perfect blend of historic charm and modern luxury, this 4 bedroom, 2.5 bath retreat is a hidden gem surrounded by lush, mature landscaping, creating a private sanctuary just minutes from the best Winter Park has to offer. From the moment you arrive, youll be captivated by the stunning curb appeal, featured on the front cover of Home & Garden magazine. The beautifully maintained exterior, with its 2023 terracotta styled flat roof sets the stage for what lies within. Inside, timeless character meets contemporary upgrades. French terracotta flooring, antique hardware, and neutral warm tones create an inviting atmosphere, while thoughtful renovations ensure every modern convenience is at your fingertips. The kitchen is a chefs dream, boasting vanilla quartz countertops with gold flecks, beautifully complementing the bronze accents and upgraded appliances. The open concept design seamlessly connects the kitchen, dining, and living area ideal for entertaining. For more intimate gatherings, unwind in the spacious family room or soak in the natural light from the attached sunroom, which overlooks the lush backyard retreat. Step outside to a tranquil space perfect for morning coffee or evening cocktails, all while enjoying the peaceful sounds of nature. The pool and jacuzzi (new heater installed in 2021) add a touch of resort style living, surrounded by meticulously curated landscaping with extensive landscape lighting (2022) that enhances the homes enchanting ambiance. Situated in a vibrant, walkable neighborhood known for its tree lined streets and friendly atmosphere, this home is just a short stroll to Lake Knowles, the YMCA, and Phelps Park. Bring your golf cart and enjoy easy access to Interlachen Golf & Country Club or the Winter Park Racquet Club. Plus, youre less than a mile from the newly renovated Winter Park Hospital and just minutes from Park Ave world class dining and shopping. Top rated schools: Zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. This rare, character filled home offers a perfect blend of privacy, luxury, and location. Dont miss your chance to own a piece of Winter Parks most desirable neighborhood!
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: Garden, Irrigation System, Lighting, Outdoor Kitchen, Private Mailbox, Rain Gutters, Sidewalk
  • Fencing: Wood
  • Flooring: Brick, Carpet, Ceramic Tile
  • Living Area: 2220.00
  • Other Structures: Outdoor Kitchen
  • Roof: Membrane, Tile
School Information
  • High School: Winter Park High
  • Middle School: Maitland Middle
  • School Elementary: Lakemont Elem
Garage and Parking
  • Garage Spaces: 1.00
Eco-Communities
  • Pool Features: In Ground
  • Water Source: Public
Utilities
  • Carport Spaces: 0.00
  • Cooling: Central Air
  • Heating: Central
  • Sewer: Public Sewer
  • Utilities: Electricity Connected, Sewer Connected, Water Connected
Finance and Tax Information
  • Home Owners Association Fee: 0.00
  • Net Operating Income: 0.00
  • Tax Year: 2024
Other Features
  • Appliances: Dishwasher, Disposal, Electric Water Heater
  • Country: US
  • Interior Features: Ceiling Fans(s), Open Floorplan, Primary Bedroom Main Floor, Walk-In Closet(s)
  • Legal Description: LAKE KNOWLES TERRACE K/4 LOT 12 BLK 1
  • Levels: One
  • Area Major: 32789 - Winter Park
  • Occupant Type: Vacant
  • Parcel Number: 32-21-30-4536-01-120
  • Views: 71
  • Zoning Code: R-1A
Similar Properties

Details for 1611 Chestnut Avenue, WINTER PARK, FL 32789
$1,295,000.00 ($390.53 / sqft )

1611 Chestnut Avenue Virtual Tour More Like This

Welcome to this stunning, fully renovated home in the heart of Winter Park. Located on Chestnut avenue beautifully rebuilt, tree lined street filled with brand new homes. This 4 bedroom, 4 bath reside

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 4
  3. Approx. 3316 sqft
  1. MLSID: O6281275
  2. Provided by PARK AVENUE REALTY LLC
  3. Contact Didem Isik-Widener
  4. mfrmls
  5. DMCA Notice
81 Pictures and Information
Details for 181 Phelps Avenue, WINTER PARK, FL 32789
$1,350,000.00 ($389.72 / sqft )

181 Phelps Avenue Virtual Tour More Like This

Renovated and Charming One Story Home in the Heart of Winter Park Nestled in the heart of Winter Park, this elegant one story home features a classic brick circular driveway and a welcoming covere

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 4
  3. Approx. 3464 sqft
  1. MLSID: O6278498
  2. Provided by ORLANDO BROTHERS REAL ESTATE LLC
  3. Contact Iluska Kruse
  4. mfrmls
  5. DMCA Notice
50 Pictures and Information
Details for 433 Carolina Avenue, WINTER PARK, FL 32789
$1,295,000.00 ($479.63 / sqft )

433 Carolina Avenue Virtual Tour More Like This

From the boutique address at 433 Carolina Ave, take a stroll down to historic Hannibal Square or to the New England gourmet corridor. On Saturday's mornings, have your breakfast at the Winter Park far

  1. Request Information
  1. Bedrooms: 5
  2. Baths: 4
  3. Approx. 2700 sqft
  1. MLSID: O6270087
  2. Provided by COLDWELL BANKER RESIDENTIAL RE
  3. Contact Thomas Bonner
  4. mfrmls
  5. DMCA Notice
22 Pictures and Information
Nearby Subdivisions
Albert Lee Ridge   Albert Lee Ridge 1st Add   Albert Lee Ridge First Additio   Alexander Place   Banks Colonial Estates   Charmont   College Place Rep   Comstock Park   Conwill Estates   Cortland Park   Dixie Terrace   Dommerich Hills Fourth Add   Dubsdread Heights   Fairbanks Park   Fairbanks Shores 4th Add   Flamingo Shores   Fontainebleau   Forest Hills   Glencoe Sub   Henkel Add   Howell Forest   Jenkins Add   Kenilworth Shores Sec 06   Lake Forest Park   Lake Killarney Shores   Lake Knowles Terrace   Lake Knowles Terrace Add 02   Lawndale   Lords Sub   Lugano Terrace   Magnolia Gardens Sub   Maitland Shores First Add   Morseland Sub   Northwood Terrace   Olympia Heights   Olympia Heights Annex   Orange Terrace   Osceola Heights   Osceola Shores Sec 03   Palmer Ave Lakeside Prop   Pennsylvania Place Rep   Sevilla   Shores Lake Killarney Sec 02   Stonehurst Estates   Sylvan Lake Shores   Tangerine Court   Tantum Add   Temple Terrace   Timberlane Shores   Tuscania   Tuscany Terrace   V H Musselwhites Sub   Virginia Heights   Virginia Heights Rep   Windsong   Windsongpreserve Point   Winter Park   Winter Park Heights   Winter Park Manor   Winter Park Village  

Contact Info

Skip to Main Content
Headshot for Associate Trudi Geniale
  1. Trudi Geniale, Broker
  2. Tropic Shores Realty
  3. Mobile: 619.578.1100
  4. Fax: 800.541.3688
  5. trudigen@live.com