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1112 Preserve Point Drive
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Details for 1112 Preserve Point Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $8,500,000.00
  2. Price sqft: $928.05 / sqft
  3. Days On Market: 130
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 9159
  8. Acreage: 1.94 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Spa/HotTub: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Lake Front
  15. Year Built: 2013
MLS#: O6312768
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Windsong Preserve Point 4376
  5. Elementary School: Brookshire Elem
  6. Middle School: Glenridge Middle
  7. High School: Winter Park High
  8. Provided by: KELLY PRICE & COMPANY LLC
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Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and private, nearly 2 acre lakefront estate, is absolutely gorgeous and is available for the first time! Cus
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2661 Via Tuscany
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Details for 2661 Via Tuscany, WINTER PARK, FL 32789
Single Family
  1. Price: $6,600,000.00
  2. Price sqft: $1,261.71 / sqft
  3. Previous Price: $8,500,000
  4. Last Price Change: 09/16/25
  5. Days On Market: 313
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5231
  10. Acreage: 0.36 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2024
MLS#: O6260493
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  5. Provided by: PV LUXURY GROUP PA
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Calling highest and best by 09/26/2025!! Seller financing available with very attractive terms introducing a unique, stunning modern home a groundbreaking architectural masterpiece, this one of
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887 Georgia Avenue
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Details for 887 Georgia Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $6,500,000.00
  2. Price sqft: $961.82 / sqft
  3. Days On Market: 66
  4. Bedrooms: 6
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6758
  8. Acreage: 1.07 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1924
MLS#: O6331715
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Dyer Susan Resub
  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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Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1 acre lot. Exuding timeless
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1181 Via Capri
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Details for 1181 Via Capri, WINTER PARK, FL 32789
Single Family
  1. Price: $5,950,000.00
  2. Price sqft: $1,059.28 / sqft
  3. Days On Market: 62
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5617
  8. Acreage: 0.30 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6332790
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Cloister Grove Sub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: PHIL KEAN REAL ESTATE LLC
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Under Construction. Situated on one of the choicest streets in Winter Park on a large and lovely lot will soon be a Phil Kean Design Group new construction project. Enjoy a world class location along
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1400 Alabama Drive
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Details for 1400 Alabama Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $5,895,000.00
  2. Price sqft: $579.36 / sqft
  3. Days On Market: 219
  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 Privileges
  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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Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .71 acre corner lot in one of Winter Park's most sought after locations. This 7,916 SF property includes a main residence of ov
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1400 Alabama Drive
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Details for 1400 Alabama Drive, Winter Park, FL 32789
Single Family
  1. Price: $5,895,000.00
  2. Price sqft: $579.36 / sqft
  3. Days On Market: 219
  4. Bedrooms: 5
  5. Baths: 9
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 10175
  8. Acreage: 0.70 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake
  13. 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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Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .71 acre corner lot in one of Winter Park's most sought after locations. This 7,916 SF property includes a main residence of ov
Listing Details and 83 Additional Pictures
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698 New York Avenue
New Construction
Green Listing
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Details for 698 New York Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $5,549,000.00
  2. Price sqft: $869.48 / sqft
  3. Days On Market: 65
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6382
  8. Acreage: 0.16 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2026
MLS#: O6318156
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Greenspk
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: CORCORAN PREMIER REALTY
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Under Construction. Rare, new construction opportunity in the heart of Winter Park JUST 1 BLOCK FROM PARK AVENUE being built by FG Schaub Custom Homes, known for grand open spaces and superior craftsm
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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. Days On Market: 105
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 5
  7. Bldg sqft: 9166
  8. Acreage: 0.69 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Canal Front,Lake Privileges
  14. 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
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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
Listing Details and 98 Additional Pictures
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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. Days On Market: 105
  4. Bedrooms: 5
  5. Baths: 7
  6. Garage / Parking Spaces: 5
  7. Bldg sqft: 9166
  8. Acreage: 0.69 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: CanalFront,Lake,LakePrivileges
  13. 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
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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
Listing Details and 98 Additional Pictures
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1221 Richmond Road
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Details for 1221 Richmond Road, WINTER PARK, FL 32789
Single Family
  1. Price: $5,450,000.00
  2. Price sqft: $835.38 / sqft
  3. Previous Price: $5,575,000
  4. Last Price Change: 10/04/25
  5. Days On Market: 86
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 6524
  10. Acreage: 0.34 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2024
MLS#: O6321906
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Virginia Heights Rep
  5. Elementary School: Audubon Park K8
  6. Middle School: Audubon Park K 8
  7. High School: Winter Park High
  8. Provided by: KELLER WILLIAMS WINTER PARK
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An Award Winning Architectural Masterpiece built by Chris Salhab of Valdara Custom Homes. 5,164 Sq Ft | 5 Bedrooms | 6 Bathrooms | Welcome to 1221 Richmond Rd, an extraordinary custom residence locat
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