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  1. Subdivision Like Maitland Shores
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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: 274
  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
  9. mfrmls
  10. DMCA Notice
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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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: 71
  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
  9. mfrmls
  10. DMCA Notice
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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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: 18
  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.
  9. mfrmls
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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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2299 Via Tuscany
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Details for 2299 Via Tuscany, WINTER PARK, FL 32789
Single Family
  1. Price: $2,295,000.00
  2. Price sqft: $428.73 / sqft
  3. Previous Price: $2,345,000
  4. Last Price Change: 02/14/26
  5. Days On Market: 140
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 5353
  10. Acreage: 0.40 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1953
MLS#: O6355858
  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: CORCORAN PREMIER REALTY
  9. mfrmls
  10. DMCA Notice
Welcome to 2299 Via Tuscany, a remarkable 4 bedroom, 3.5 bathroom residence in the prestigious Winter Park Vias. This 3,986 square foot home, set on a .40 acre private lot, offers a blend of luxury an
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1016 Howell Branch Road
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Details for 1016 Howell Branch Road, WINTER PARK, FL 32789
Single Family
  1. Price: $1,699,000.00
  2. Price sqft: $414.80 / sqft
  3. Days On Market: 4
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4096
  8. Acreage: 0.37 acres
  9. Pool: No
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Canal - Freshwater,Canal Front
  14. Year Built: 1959
MLS#: O6392409
  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: PLAID PROPERTIES, LLC
  9. mfrmls
  10. DMCA Notice
Canal Front Oasis on the Winter Park Chain of Lakes! (Seller Financing Available for Qualified Buyers) Welcome to 1016 Howell Branch Road, where every day feels like a getaway. This beautifully reimag
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952 Moss Lane
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Details for 952 Moss Lane, WINTER PARK, FL 32789
Single Family
  1. Price: $1,329,950.00
  2. Price sqft: $281.00 / sqft
  3. Previous Price: $1,359,950
  4. Last Price Change: 02/12/26
  5. Days On Market: 307
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4733
  10. Acreage: 0.21 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2008
MLS#: TB8388549
  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: THE SHOP REAL ESTATE CO.
  9. mfrmls
  10. DMCA Notice
Back on market at no fault of the seller! Brand new Roof and HVAC systems 2025. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and
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67 Cypress Lane
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Details for 67 Cypress Lane, MAITLAND, FL 32751
Single Family
  1. Price: $1,225,000.00
  2. Price sqft: $394.40 / sqft
  3. Previous Price: $1,339,000
  4. Last Price Change: 03/07/26
  5. Days On Market: 75
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3106
  10. Acreage: 0.27 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1979
MLS#: O6371328
  1. County: ORANGE
  2. City: MAITLAND
  3. Zipcode: 32751
  4. Subdivision: Maitland Shores
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
  9. mfrmls
  10. DMCA Notice
Welcome to 67 Cypress Lane, a stunning single owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This archit
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1016 Howell Branch Road
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Details for 1016 Howell Branch Road, WINTER PARK, FL 32789
Rental
  1. Price: $7,200.00
  2. Price sqft: $1.76 / sqft
  3. Days On Market: 4
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4096
  8. Acreage: 0.37 acres
  9. Pool: No
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Canal - Freshwater,Canal Front
  14. Year Built: 1959
MLS#: O6392422
  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: PLAID PROPERTIES, LLC
  9. mfrmls
  10. DMCA Notice
Canal Front Oasis on the Winter Park Chain of Lakes! Welcome to 1016 Howell Branch Road, where every day feels like a getaway. (Property can be leased furnished for an additional fee.) This beaut
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