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  1. Subdivision Like Maitland Shores
2211 Azalea Place
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Details for 2211 Azalea Place, WINTER PARK, FL 32789
Single Family
  1. Price: $5,495,000.00
  2. Price sqft: $599.50 / sqft
  3. Previous Price: $5,950,000
  4. Last Price Change: 11/02/25
  5. Days On Market: 135
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 5
  9. Bldg sqft: 9166
  10. Acreage: 0.69 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Canal Front,Lake Privileges
  16. Year Built: 2008
MLS#: O6319674
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Maitland Shores
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: FORTUNE INTERNATIONAL REALTY
  9. mfrmls
  10. DMCA Notice
Exquisite Waterfront Estate in the Heart of Winter Park Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Parks most prestigious neighb
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2550 Venetian Way
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Details for 2550 Venetian Way, WINTER PARK, FL 32789
Single Family
  1. Price: $2,599,000.00
  2. Price sqft: $423.36 / sqft
  3. Previous Price: $2,699,000
  4. Last Price Change: 10/18/25
  5. Days On Market: 352
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 6139
  10. Acreage: 0.27 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Canal - Freshwater
  15. Year Built: 2008
MLS#: O6258445
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Maitland Shores First Add
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: COMPASS FLORIDA LLC
  9. mfrmls
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"The richness of an artist is the fusion of influences that have shaped his life and work", ~ Fernando Botero. WELCOME HOME to 2550 Venetian Way, located in the historic and renowned city of Winter Pa
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2299 Via Tuscany
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Details for 2299 Via Tuscany, WINTER PARK, FL 32789
Single Family
  1. Price: $2,345,000.00
  2. Price sqft: $438.07 / sqft
  3. Days On Market: 1
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5353
  8. Acreage: 0.40 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1953
MLS#: O6355858
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Maitland Shores
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: CORCORAN PREMIER REALTY
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Stunning 4 bedroom, renovated pool home with new Architectural shingle roof (2023) on a generous .40 acre lot in the highly coveted Winter Park Vias with bright open living areas, high ceilings, hardw
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1016 Howell Branch Road
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Details for 1016 Howell Branch Road, WINTER PARK, FL 32789
Single Family
  1. Price: $1,836,000.00
  2. Price sqft: $448.24 / sqft
  3. Days On Market: 15
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4096
  8. Acreage: 0.37 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Canal - Freshwater
  13. Year Built: 1959
MLS#: O6354284
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Maitland Shores
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: PLAID PROPERTIES, LLC
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Canal Front Oasis on the Winter Park Chain of Lakes! Welcome to 1016 Howell Branch Road, where every day feels like a getaway. This beautifully reimagined 4 bedroom, 3 bath residence offers 3,142 squ
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913 Moss Lane
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Details for 913 Moss Lane, WINTER PARK, FL 32789
Single Family
  1. Price: $975,000.00
  2. Price sqft: $516.69 / sqft
  3. Previous Price: $999,000
  4. Last Price Change: 11/01/25
  5. Days On Market: 180
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 1887
  10. Acreage: 0.19 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1953
MLS#: O6307671
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Maitland Shores First Add
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: VECTOR PROPERTY GROUP
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***Lease purchase available | Remodeled in 2023 | Furniture package available | Short term rental allowed*** Discover Your Dream Retreat at 913 Moss Lane, Winter Park, FL A 2023 Masterpiece Awaits! S
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2020 Venetian Way
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Details for 2020 Venetian Way, WINTER PARK, FL 32789
Rental
  1. Price: $8,990.00
  2. Price sqft: $1.48 / sqft
  3. Previous Price: $9,995
  4. Last Price Change: 10/04/25
  5. Days On Market: 117
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6065
  10. Acreage: 0.63 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Privileges
  15. Year Built: 1979
MLS#: O6324414
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Maitland Shores
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: PALMANO GROUP RE BROKERAGE LLC
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Only available for a 4 to 6 month lease. This RARE LAKEFRONT retreat is located on a quiet, tree lined street in the highly sought after Vias of Winter Park. Custom built and elevated on a prime lot w
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