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  1. School = Dommerich Elem
  2. Listing Status = Active
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: 276
  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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1302 Raintree Place
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Details for 1302 Raintree Place, WINTER PARK, FL 32789
Single Family
  1. Price: $4,995,000.00
  2. Price sqft: $845.75 / sqft
  3. Previous Price: $5,150,000
  4. Last Price Change: 03/07/26
  5. Days On Market: 161
  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
  7. High School: Winter Park
  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: 72
  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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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: 55
  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
  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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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: 76
  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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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: 73
  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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670 Williams Drive
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Details for 670 Williams Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $2,995,000.00
  2. Price sqft: $574.09 / sqft
  3. Previous Price: $3,090,000
  4. Last Price Change: 03/20/26
  5. Days On Market: 58
  6. Bedrooms: 5
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5217
  10. Acreage: 0.31 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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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125 Whitecaps Circle
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Details for 125 Whitecaps Circle, MAITLAND, FL 32751
Land
  1. Price: $2,795,000.00
  2. Previous Price: $2,875,000
  3. Last Price Change: 02/19/26
  4. Days On Market: 188
  5. Acreage: 0.42 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Lake Privileges
  10. Year Built: Not Available
MLS#: O6345537
  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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Wonderful lakefront lot opportunity to create a custom legacy estate on Lake Maitland, part of the Maitland Winter Park Chain of Lakes. Lakefront homesites are becoming increasingly rare, and this off
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2550 Venetian Way
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Details for 2550 Venetian Way, WINTER PARK, FL 32789
Single Family
  1. Price: $2,450,000.00
  2. Price sqft: $387.84 / sqft
  3. Days On Market: 20
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6317
  8. Acreage: 0.27 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Canal - Freshwater,Lake Privileges
  13. Year Built: 2008
MLS#: O6388219
  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: PALM PROPERTIES OF CF, INC.
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Chain of Lakes Water Front Home with Private Boat Dock, Winter Park Luxury Living. Step into your future with this extraordinary custom built residence, inspired by the artistic richness of Fernan
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1760 Legion Drive
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Details for 1760 Legion Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $2,395,000.00
  2. Price sqft: $389.49 / sqft
  3. Days On Market: 36
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 6149
  8. Acreage: 0.34 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1964
MLS#: O6383603
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Green Oaks 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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Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location
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