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  1. School = Maitland
  2. Listing Status = Active
1640 Adams Drive
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Details for 1640 Adams Drive, MAITLAND, FL 32751
Single Family
  1. Price: $10,450,000.00
  2. Price sqft: $1,231.00 / sqft
  3. Previous Price: $10,950,000
  4. Last Price Change: 02/20/26
  5. Days On Market: 314
  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
  9. mfrmls
  10. DMCA Notice
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 Mediterranea
Listing Details and 59 Additional Pictures
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40 Palmer Avenue
New Construction
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Details for 40 Palmer Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $6,950,000.00
  2. Price sqft: $799.03 / sqft
  3. Days On Market: 43
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 8698
  8. Acreage: 0.30 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2026
MLS#: O6380444
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Elementary School: Lakemont Elem
  5. Middle School: Maitland
  6. High School: Winter Park
  7. Provided by: ONE LUXURY INTERNATIONAL LLC
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Under Construction. Opportunities like this rarely present themself, just a eight minute walk from the iconic shops, restaurants, and cafs of Park Avenue, 40 Palmer represents a rare convergence of ar
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1260 Alabama Drive
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Details for 1260 Alabama Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $6,900,000.00
  2. Price sqft: $875.41 / sqft
  3. Days On Market: 21
  4. Bedrooms: 6
  5. Baths: 7
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 7882
  8. Acreage: 0.57 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Canal - Freshwater
  14. Year Built: 1991
MLS#: O6387200
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: J Kronenberger Sub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
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Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of
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550 Palmer Avenue
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New Construction
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Details for 550 Palmer Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $6,895,000.00
  2. Price sqft: $861.66 / sqft
  3. Previous Price: $7,200,000
  4. Last Price Change: 01/07/26
  5. Days On Market: 153
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 8002
  10. Acreage: 0.48 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2025
MLS#: O6349188
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Osceola Place
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
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Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenues renowned shops, fine dining, and the iconic Winter Park 9 hole golf course,
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1200 Via Salerno
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Details for 1200 Via Salerno, WINTER PARK, FL 32789
Single Family
  1. Price: $6,450,000.00
  2. Price sqft: $793.94 / sqft
  3. Days On Market: 39
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 8124
  8. Acreage: 0.45 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2001
MLS#: O6381761
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Cloister Grove Sub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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Along one of the cobblestone brick streets in the prestigious Vias of Winter Park, this completely renovated residence pairs timeless European influence with clean architectural lines and bespoke fini
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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
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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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New Construction
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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: 159
  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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1660 Palmer Avenue
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New Construction
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Details for 1660 Palmer Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $4,950,000.00
  2. Price sqft: $661.50 / sqft
  3. Previous Price: $5,200,000
  4. Last Price Change: 07/25/25
  5. Days On Market: 397
  6. Bedrooms: 5
  7. Baths: 7
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 7483
  10. Acreage: 0.36 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2024
MLS#: O6282425
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Comstock Park
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
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New Hamptons style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exception
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1150 Via Salerno
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New Construction
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Details for 1150 Via Salerno, WINTER PARK, FL 32789
Single Family
  1. Price: $4,750,000.00
  2. Price sqft: $1,082.99 / sqft
  3. Days On Market: 269
  4. Bedrooms: 4
  5. Baths: 6
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4386
  8. Acreage: 0.21 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: O6321143
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Cloister Grove Sub
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
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In the heart of Winter Parks coveted Vias neighborhood, 1150 Via Salerno is a newly completed Mediterranean minimalist residence that blends architectural refinement w/ organic warmth. Designed and de
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503 Interlachen Avenue
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Details for 503 Interlachen Avenue, WINTER PARK, FL 32789
Land
  1. Price: $4,500,000.00
  2. Previous Price: $4,999,000
  3. Last Price Change: 01/29/26
  4. Days On Market: 235
  5. Acreage: 0.48 acres
  6. Pool: No
  7. Waterfront: No
  8. Year Built: Not Available
MLS#: O6331207
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  5. Elementary School: Lakemont Elem
  6. Middle School: Maitland
  7. High School: Winter Park
  8. Provided by: KELLY PRICE & COMPANY LLC
  9. mfrmls
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JUST LISTED RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK OFFERED AT $4,999,000!!! Zoned R 3, this multi family, prime piece of land is ready for development. Luxury townhomes or condos, nothi
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