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  1. School = Maitland Middle
1400 Alabama Drive
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Details for 1400 Alabama Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $6,950,000.00
  2. Price sqft: $683.05 / sqft
  3. Days On Market: 29
  4. Bedrooms: 5
  5. Baths: 9
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 10175
  8. Acreage: 0.70 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake
  14. Year Built: 1996
MLS#: O6285791
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: J Kronenberger Sub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: THE AGENCY ORLANDO
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Custom Waterfront Estate located in the heart of Winter Park with a covered Boat Dock on Lake Maitland the largest of the Winter Park Chain of Lakes. A timeless Neoclassical Italian home that exudes
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2228 Azalea Place
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Details for 2228 Azalea Place, WINTER PARK, FL 32789
Single Family
  1. Price: $5,400,000.00
  2. Price sqft: $797.05 / sqft
  3. Days On Market: 163
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6775
  8. Acreage: 0.33 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2008
MLS#: O6250411
  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
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Gorgeous Winter Park home beautifully curated with designer details and recently featured in Junes Orange Appeal and was the 2022 Mystery Home Tour selected by Council of 101 for the Orlando Museum of
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2020 Venetian Way
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Details for 2020 Venetian Way, WINTER PARK, FL 32789
Single Family
  1. Price: $3,995,000.00
  2. Price sqft: $658.70 / sqft
  3. Days On Market: 2
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6065
  8. Acreage: 0.63 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Front,Lake
  13. Year Built: 1979
MLS#: O6288344
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Venetian
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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This Custom Built home has stylish midcentury influences and is elevated over a .64 acre lot with clear views to the Isle of Sicily and long views across Lake Maitland. A quaint street lined with oaks
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1250 Maitland Avenue
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Details for 1250 Maitland Avenue, MAITLAND, FL 32751
Land
  1. Price: $3,990,900.00
  2. Previous Price: $4,490,900
  3. Last Price Change: 03/27/25
  4. Days On Market: 247
  5. Acreage: 7.82 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Lake Front
  10. Year Built: Not Available
MLS#: O6222186
  1. County: ORANGE
  2. City: MAITLAND
  3. Zipcode: 32751
  4. Subdivision: Woodbridge
  5. Elementary School: Lake Sybelia Elem
  6. Middle School: Maitland Middle
  7. High School: Edgewater High
  8. Provided by: AG REALTY SERVICES LLC
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Amazing opportunity for developers, residential builders, or those seeking a personal private estate! This unique lakeview and lakefront property features approximately +/ 8 acres of usable land withi
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851 Georgia Avenue
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Details for 851 Georgia Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $3,950,000.00
  2. Price sqft: $45.01 / sqft
  3. Days On Market: 10
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 87762
  8. Acreage: 0.89 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1935
MLS#: O6291851
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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Nestled on a sprawling 0.89 acre estate, this luxurious home offers the perfect balance of privacy and convenience, just moments from the vibrant downtown Winter Park. A rare gem, this 1935 James Gamb
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640 Old Horatio Avenue
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Details for 640 Old Horatio Avenue, MAITLAND, FL 32751
Single Family
  1. Price: $3,450,000.00
  2. Price sqft: $648.74 / sqft
  3. Days On Market: 14
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5318
  8. Acreage: 0.40 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Canal - Freshwater
  14. Year Built: 2025
MLS#: O6290533
  1. County: ORANGE
  2. City: MAITLAND
  3. Zipcode: 32751
  4. Subdivision: Long Branch Sub
  5. Elementary School: Lake Sybelia Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: RE/MAX EXCLUSIVE COLLECTION
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Just Completed!! New Construction with Winter Park Chain of Lakes Access!! You'll be stunned by this gorgeous coastal style home on a private canal that leads to Lake Maitland. This magnificent resid
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2550 Venetian Way
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Details for 2550 Venetian Way, WINTER PARK, FL 32789
Single Family
  1. Price: $2,999,900.00
  2. Price sqft: $488.66 / sqft
  3. Days On Market: 132
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6139
  8. Acreage: 0.27 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Canal - Freshwater
  13. 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
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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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1630 Lasbury Avenue
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Details for 1630 Lasbury Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $2,895,000.00
  2. Price sqft: $548.61 / sqft
  3. Days On Market: 17
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5277
  8. Acreage: 0.34 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2003
MLS#: O6289369
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Comstock Park
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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Nestled on a serene, brick paved street in the heart of Winter Park, this elegant 5 bedroom, 3.2 bathroom pool home is situated on a stunning oversized lot. Custom built in 2003, it offers a thoughtfu
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7849 Georgeann Street
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Details for 7849 Georgeann Street, WINTER PARK, FL 32792
Single Family
  1. Price: $2,690,000.00
  2. Price sqft: $380.16 / sqft
  3. Days On Market: 2
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7076
  8. Acreage: 0.86 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Lake Front
  14. Year Built: 2012
MLS#: O6294301
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32792
  4. Subdivision: Georgeann Homes
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: KELLER WILLIAMS REALTY AT THE PARKS
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Lakefront luxury in winter park. This custom gated estate feels like living at a resort. Situated on the beautiful 72 acre private, spring fed lake waunatta, this property has it all. Completely rebui
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2412 Chantilly Avenue
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Details for 2412 Chantilly Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $2,395,000.00
  2. Price sqft: $460.93 / sqft
  3. Days On Market: 46
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5196
  8. Acreage: 0.27 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2024
MLS#: O6278049
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park Village
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: COMPASS FLORIDA LLC
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Discover an extraordinary blend of modern elegance and thoughtful craftsmanship in this brand new architectural gem by DaVinci Development. This stunning five bedroom, six and a half bathroom home spa
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Tropic Shores Realty - Crystal River
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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Datafeed Last updated on March 31, 2025 @ 12:00 am
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