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  1. School = Dommerich Elem
  2. Listing Status = Active
1640 Adams Drive
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Details for 1640 Adams Drive, MAITLAND, FL 32751
Single Family
  1. Price: $10,950,000.00
  2. Price sqft: $1,289.90 / sqft
  3. Previous Price: $11,950,000
  4. Last Price Change: 09/06/25
  5. Days On Market: 269
  6. Bedrooms: 5
  7. Baths: 8
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 8489
  10. Acreage: 1.86 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Lake Privileges
  16. Year Built: 1991
MLS#: O6304588
  1. County: ORANGE
  2. City: MAITLAND
  3. Zipcode: 32751
  4. Subdivision: Adams Grove
  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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Villa Serenata A Lakefront Legacy on Lake Maitland. Behind private iron gates along the storied shores of Lake Maitland, Villa Serenata presents a rare opportunity to own a distinguished Mediterra
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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: 12/07/25
  5. Days On Market: 229
  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
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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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1302 Raintree Place
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Details for 1302 Raintree Place, WINTER PARK, FL 32789
Single Family
  1. Price: $5,150,000.00
  2. Price sqft: $872.00 / sqft
  3. Previous Price: $5,300,000
  4. Last Price Change: 01/13/26
  5. Days On Market: 114
  6. Bedrooms: 5
  7. Baths: 6
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5906
  10. Acreage: 0.34 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2025
MLS#: O6353083
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Camwood Sub
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophisticationall just steps from Winter Parks iconic Park Avenue.
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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: 25
  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 Middle
  7. High School: Winter Park High
  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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948 Poinciana Lane
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Details for 948 Poinciana Lane, WINTER PARK, FL 32789
Single Family
  1. Price: $3,599,000.00
  2. Price sqft: $794.66 / sqft
  3. Days On Market: 26
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4529
  8. Acreage: 0.30 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. 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 Middle
  7. High School: Winter Park High
  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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127 Whitecaps Circle
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Details for 127 Whitecaps Circle, MAITLAND, FL 32751
Land
  1. Price: $3,425,000.00
  2. Previous Price: $3,495,000
  3. Last Price Change: 01/30/26
  4. Days On Market: 29
  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 Middle
  6. High School: Winter Park High
  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: $3,399,999.00
  2. Price sqft: $539.94 / sqft
  3. Previous Price: $3,499,999
  4. Last Price Change: 01/25/26
  5. Days On Market: 240
  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 Middle
  7. High School: Winter Park High
  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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350 Northwind Road
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Details for 350 Northwind Road, MAITLAND, FL 32751
Single Family
  1. Price: $3,299,000.00
  2. Price sqft: $459.92 / sqft
  3. Days On Market: 7
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7173
  8. Acreage: 0.36 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. 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 Middle
  7. High School: Winter Park High
  8. Provided by: SOTERA LIVING
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Nestled within the gated 9 acre Lake Maitland Owl Preserve, this striking contemporary residencecrafted by acclaimed green builder E2 Homes offers a rare blend of architectural distinction, privacy, a
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670 Williams Drive
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Details for 670 Williams Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $3,190,000.00
  2. Price sqft: $611.46 / sqft
  3. Days On Market: 11
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5217
  8. Acreage: 0.31 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2016
MLS#: O6376953
  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: RE/MAX 200 REALTY
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This stunning custom residence built by respected Winter Park Builder Charles Clayton blends classic elegance with refined modern comfort, offering seamless indooroutdoor living and impeccable craftsm
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1401 Green Cove Road
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Details for 1401 Green Cove Road, WINTER PARK, FL 32789
Single Family
  1. Price: $2,900,000.00
  2. Price sqft: $425.16 / sqft
  3. Days On Market: 93
  4. Bedrooms: 3
  5. Baths: 7
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6821
  8. Acreage: 0.27 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2009
MLS#: O6358093
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Camwood Sub
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: ANCHOR REAL ESTATE
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Set across Lake Maitland on a street where every home is an architectural gem, this Award winning Villa Toscana blends Old World craftsmanship with timeless architectural elegance in one of Winter Par
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