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  1. School = Maitland Middle
Details for 1840 Bryan Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $1,899,500.00
  2. Price sqft: $407.18 / sqft
  3. Previous Price: $1,999,500
  4. Last Price Change: 11/16/25
  5. Days On Market: 229
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4665
  10. Acreage: 0.29 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2014
MLS#: O6304239
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Lakeview Terrace
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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This custom 2014 built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all that Winter Park offers. A home with function and flexibility with a s
Details for 825 Palmer Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $1,799,000.00
  2. Price sqft: $388.39 / sqft
  3. Days On Market: 102
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4632
  8. Acreage: 0.35 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Canal Front
  13. Year Built: 1953
MLS#: O6341209
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: J Kronenberger Sub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: KELLY PRICE & COMPANY LLC
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825 Palmer Avenue, Winter Park | $1,799,000 A Rare Venetian Canal Treasure Awaits Your Vision! Discover an extraordinary opportunity on one of Winter Park's most coveted waterways. This exceptional
Details for 800 Hamilton Place Court, WINTER PARK, FL 32789
Single Family
  1. Price: $1,295,000.00
  2. Price sqft: $331.03 / sqft
  3. Previous Price: $1,300,000
  4. Last Price Change: 11/11/25
  5. Days On Market: 173
  6. Bedrooms: 3
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3912
  10. Acreage: 0.15 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2015
MLS#: O6321816
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Hamilton Place
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: EPIC REAL ESTATE ADVISORS LLC
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Custom built and beautifully maintained, this large 3 bedroom home with loft is located in prime Old Winter Park on a quiet cul de sac. The interior boasts 18'+ high ceilings, creating a grand and air
Details for 1447 Caring Court, Maitland, FL 32751
Single Family
  1. Price: $625,000.00
  2. Price sqft: $220.69 / sqft
  3. Days On Market: 7
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2832
  8. Acreage: 0.13 acres
  9. Pool: Yes
  10. Community Pool: Yes
  11. Waterfront: No
  12. Year Built: 2006
MLS#: O6364719
  1. County: ORANGE
  2. City: Maitland
  3. Zipcode: 32751
  4. Subdivision: Enclave/maitland A F
  5. Elementary School: Lake Sybelia Elem
  6. Middle School: Maitland Middle
  7. High School: Edgewater High
  8. Provided by: KELLER WILLIAMS HERITAGE REALTY
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Beautiful move in ready home in the highly sought after gated community of Montacino, located in the heart of Maitland. This single story Mediterranean inspired home boasts three spacious bedrooms, in
Details for 2042 Yorkshire Drive, Winter Park, FL 32792
Land
  1. Price: $499,000.00
  2. Days On Market: 5
  3. Acreage: 0.24 acres
  4. Pool: No
  5. Waterfront: No
  6. Year Built: Not Available
MLS#: O6366830
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32792
  4. Subdivision: Park Manor First Add
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: KELLER WILLIAMS WINTER PARK
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This location cant be beat! 2042 Yorkshire Drive is a nearly quarter acre (.24) corner lot in desirable Winter Park with sought after schools: Lakemont Elementary, Maitland Middle, and Winter Park Hig
Details for 6 Barnard Court, MAITLAND, FL 32751
Single Family
  1. Price: $429,900.00
  2. Price sqft: $220.12 / sqft
  3. Days On Market: 34
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 1953
  8. Acreage: 0.20 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1956
MLS#: O6360107
  1. County: ORANGE
  2. City: MAITLAND
  3. Zipcode: 32751
  4. Subdivision: Lake Eulalia Heights
  5. Elementary School: Hungerford Elem
  6. Middle School: Maitland Middle
  7. High School: Edgewater High
  8. Provided by: LPT REALTY, LLC
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Step into timeless style with this completely updated mid century modern home tucked away on a quiet Maitland cul de sac. This 3 bedroom, 2 bath residence offers 1,521 sq ft of thoughtfully designed l
Details for 184 Sandlewood Trail 2, WINTER PARK, FL 32789
Condominium
  1. Price: $309,000.00
  2. Price sqft: $272.73 / sqft
  3. Previous Price: $315,000
  4. Last Price Change: 11/05/25
  5. Days On Market: 208
  6. Bedrooms: 2
  7. Baths: 3
  8. Bldg sqft: 1133
  9. Acreage: 0.19 acres
  10. Pool: No
  11. Waterfront: No
  12. Year Built: 1985
MLS#: O6311365
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Sandlewood Creek Condo
  5. Building: Sandlewood Creek Condo
  6. Elementary School: Dommerich Elem
  7. Middle School: Maitland Middle
  8. High School: Winter Park High
  9. Provided by: EXP REALTY LLC
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FHA, VA, and DPA approved. Nestled just minutes from the charming boutiques and award winning restaurants of Park Avenue, this beautifully updated 2 bedroom, 2.5 bathroom condo offers the perfect blen
Details for 519 Park North Court, Winter Park, FL 32789
Rental
  1. Price: $7,000.00
  2. Price sqft: $1.59 / sqft
  3. Days On Market: 8
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4415
  8. Acreage: 0.30 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1989
MLS#: O6365855
  1. County: ORANGE
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Park North
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: KELLY PRICE & COMPANY LLC
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Discover refined single story living at 519 Park North Court, an exceptional luxury rental in the heart of Winter Park. This beautifully appointed four bedroom, three and a half bath residence offers
Details for 1253 Blessing Street, MAITLAND, FL 32751
Rental
  1. Price: $2,500.00
  2. Price sqft: $1.21 / sqft
  3. Days On Market: 59
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 2073
  8. Acreage: 0.04 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2006
MLS#: O6352867
  1. County: ORANGE
  2. City: MAITLAND
  3. Zipcode: 32751
  4. Subdivision: Enclavemaitland Af
  5. Elementary School: Lake Sybelia Elem
  6. Middle School: Maitland Middle
  7. High School: Edgewater High
  8. Provided by: PALMANO GROUP RE BROKERAGE LLC
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Welcome to Montacino Gated Community Living at Its Finest! Available December 8, 2025, this beautifully updated 3 bedroom, 2.5 bath townhome offers a perfect blend of modern finishes, open living