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  1. City = Winter Park
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: 110
  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
  7. High School: Winter Park
  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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New Construction
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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: 09/08/25
  5. Days On Market: 293
  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!! Private auction with bid reserve at $6,600,000 seller financing available with very attractive terms introducing a unique, stunning modern home a ground
Listing Details and 99 Additional Pictures
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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: 46
  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
  7. High School: Winter Park
  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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1240 Harding Street
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Details for 1240 Harding Street, Winter Park, FL 32789
Single Family
  1. Price: $5,999,000.00
  2. Price sqft: $729.81 / sqft
  3. Days On Market: 6
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 8220
  8. Acreage: 0.55 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2021
MLS#: O6342506
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: J Kronenberger Sub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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This stunning private residence is situated on an oversized lot featuring a private sports pad, kids playground, and sparkling pool. Encompassing over 6,700 square feet of expansive .55 acre lot, t
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1240 Harding Street
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Details for 1240 Harding Street, WINTER PARK, FL 32789
Single Family
  1. Price: $5,999,000.00
  2. Price sqft: $729.81 / sqft
  3. Days On Market: 6
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 8220
  8. Acreage: 0.55 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2021
MLS#: O6342506
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: J Kronenberger Sub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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This stunning private residence is situated on an oversized lot featuring a private sports pad, kids playground, and sparkling pool. Encompassing over 6,700 square feet of expansive .55 acre lot, t
Listing Details and 63 Additional Pictures
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1181 Via Capri
New Construction
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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: 41
  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
  7. High School: Winter Park
  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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1221 Richmond Road
Reduced
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Details for 1221 Richmond Road, WINTER PARK, FL 32789
Single Family
  1. Price: $5,575,000.00
  2. Price sqft: $854.54 / sqft
  3. Previous Price: $5,800,000
  4. Last Price Change: 09/10/25
  5. Days On Market: 66
  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 K
  6. Middle School: Audubon Park K
  7. High School: Winter Park
  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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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: 45
  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
  7. High School: Winter Park
  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 FG Schaub Custom Homes, known for grand open spaces and superior craftsmans
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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. Previous Price: $5,950,000
  4. Last Price Change: 09/08/25
  5. Days On Market: 84
  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
  7. High School: Winter Park
  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
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503 Interlachen Avenue
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Details for 503 Interlachen Avenue, WINTER PARK, FL 32789
Land
  1. Price: $4,999,000.00
  2. Days On Market: 45
  3. Acreage: 0.48 acres
  4. Pool: No
  5. Waterfront: No
  6. Year Built: Not Available
MLS#: O6331207
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
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JUST LISTED RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK OFFERED AT $4,999,000!!! Zoned R 3, this multi family, prime piece of land is ready for development. Luxury townhomes or condos, nothi
Listing Details and 11 Additional Pictures
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