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2211 Azalea Place
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Details for 2211 Azalea Place, WINTER PARK, FL 32789
Single Family
  1. Price: $5,250,000.00
  2. Price sqft: $572.77 / sqft
  3. Previous Price: $5,495,000
  4. Last Price Change: 04/16/26
  5. Days On Market: 299
  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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1760 Via Venetia
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Details for 1760 Via Venetia, WINTER PARK, FL 32789
Single Family
  1. Price: $4,650,000.00
  2. Price sqft: $512.96 / sqft
  3. Days On Market: 22
  4. Bedrooms: 4
  5. Baths: 7
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 9065
  8. Acreage: 0.43 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2013
MLS#: O6391840
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Sicilian Shores Rep 02
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Presenting an extraordinary southern traditional estate in the heart of the coveted Vias of Winter Park, a residence that effortlessly blends timeless architecture with exceptional craftsmanship. This
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1441 Cardinal Court
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Details for 1441 Cardinal Court, WINTER PARK, FL 32789
Single Family
  1. Price: $4,285,000.00
  2. Price sqft: $772.77 / sqft
  3. Days On Market: 3
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5545
  8. Acreage: 0.36 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2022
MLS#: O6399395
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winflor Court Pt Rep
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: CHARLES RUTENBERG REALTY ORLANDO
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Beautifully built in 2022 by Lonnie Richardson, this custom one story home sits on a quiet cul de sac in the heart of Winter Park. Designed with a modern, timeless style, it offers luxury finishes pai
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1417 Williams Drive
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Details for 1417 Williams Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $4,199,000.00
  2. Price sqft: $682.76 / sqft
  3. Days On Market: 95
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6150
  8. Acreage: 0.37 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2026
MLS#: O6368668
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Park Grove
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: ONE LUXURY INTERNATIONAL LLC
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Under Construction. Tucked away on a quiet cul de sac in the coveted Park Grove community, this home sits on an expansive 0.37 acre lot, just moments from the boutiques, dining, and charm of Park Aven
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2020 Via Tuscany
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Details for 2020 Via Tuscany, Winter Park, FL 32789
Single Family
  1. Price: $4,195,000.00
  2. Price sqft: $798.14 / sqft
  3. Days On Market: 2
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5256
  8. Acreage: 0.35 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6400063
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Tuscania
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: VISTA CAY REALTY COMPANY
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PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the
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2020 Via Tuscany
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Details for 2020 Via Tuscany, WINTER PARK, FL 32789
Single Family
  1. Price: $4,195,000.00
  2. Price sqft: $798.14 / sqft
  3. Days On Market: 23
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5256
  8. Acreage: 0.35 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6394117
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Tuscania
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: CORCORAN PREMIER REALTY
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PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the
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127 Whitecaps Circle
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Details for 127 Whitecaps Circle, MAITLAND, FL 32751
Land
  1. Price: $3,295,000.00
  2. Previous Price: $3,425,000
  3. Last Price Change: 02/19/26
  4. Days On Market: 99
  5. Acreage: 0.56 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Lake Privileges
  10. Year Built: Not Available
MLS#: O6367169
  1. County: ORANGE
  2. City: MAITLAND
  3. Zipcode: 32751
  4. Elementary School: Dommerich Elem
  5. Middle School: Maitland
  6. High School: Winter Park
  7. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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A rare opportunity to secure a Lake Maitland homesite on the desired MaitlandWinter Park Chain of Lakes, an increasingly limited offering as quality lakefront parcels continue to disappear. Along a qu
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1761 Legion Drive
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Details for 1761 Legion Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $3,270,000.00
  2. Price sqft: $519.30 / sqft
  3. Previous Price: $3,295,000
  4. Last Price Change: 04/16/26
  5. Days On Market: 310
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6297
  10. Acreage: 0.39 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2017
MLS#: O6302616
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Green Oaks Rep 02
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: SCANLON REALTY GROUP LLC
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One of the most coveted neighborhoods in all of Winter Park! This custom built 5 bedroom, 5.5 bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and
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948 Poinciana Lane
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Details for 948 Poinciana Lane, WINTER PARK, FL 32789
Single Family
  1. Price: $3,199,000.00
  2. Price sqft: $706.34 / sqft
  3. Previous Price: $3,599,000
  4. Last Price Change: 03/24/26
  5. Days On Market: 96
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4529
  10. Acreage: 0.30 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2001
MLS#: O6372165
  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
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
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Timeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an extraordinary residence where exceptional craftsmanship and sophisticated design converge at 948 Poinciana Lan
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350 Northwind Road
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Details for 350 Northwind Road, MAITLAND, FL 32751
Single Family
  1. Price: $3,100,000.00
  2. Price sqft: $432.18 / sqft
  3. Previous Price: $3,299,000
  4. Last Price Change: 04/11/26
  5. Days On Market: 78
  6. Bedrooms: 5
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 7173
  10. Acreage: 0.36 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2019
MLS#: O6377888
  1. County: ORANGE
  2. City: MAITLAND
  3. Zipcode: 32751
  4. Subdivision: Lake Maitland Owl Preserve
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: SOTERA LIVING
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Nestled within the 9 acre Lake Maitland Owl Preserve, this striking contemporary residencecrafted by acclaimed green builder E2 Homes offers a rare blend of architectural distinction, privacy, and nat
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