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    1. School = Maitland
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    570 Manor Road
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    Details for 570 Manor Road, MAITLAND, FL 32751
    Single Family
    1. Price: $12,500,000.00
    2. Price sqft: $838.76 / sqft
    3. Days On Market: 387
    4. Bedrooms: 6
    5. Baths: 10
    6. Garage / Parking Spaces: 6
    7. Bldg sqft: 14903
    8. Acreage: 2.73 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: Yes
    12. Wateraccess: Yes
    13. Waterfront Type: Lake Front,Lake Privileges
    14. Year Built: 1996
    MLS#: O6300040
    1. County: ORANGE
    2. City: MAITLAND
    3. Zipcode: 32751
    4. Subdivision: Lake Maitland Manor
    5. Elementary School: Lake Sybelia Elem
    6. Middle School: Maitland Middle
    7. High School: Winter Park High
    8. Provided by: FORTUNE INTERNATIONAL REALTY
    9. mfrmls
    10. DMCA Notice
    Welcome to Maison du Lac a breathtaking lakefront estate that epitomizes unrivaled luxury, timeless elegance, and an extraordinary lifestyle. Situated on an expansive 2.7 acre lot along the prestigio
    Listing Details and 98 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: 89
    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 Middle
    6. High School: Winter Park High
    7. Provided by: ONE LUXURY INTERNATIONAL LLC
    8. mfrmls
    9. DMCA Notice
    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
    Listing Details and 16 Additional Pictures
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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: 67
    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 Middle
    7. High School: Winter Park High
    8. Provided by: KELLY PRICE & COMPANY LLC
    9. mfrmls
    10. DMCA Notice
    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
    Listing Details and 57 Additional Pictures
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    550 Palmer Avenue
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    Details for 550 Palmer Avenue, WINTER PARK, FL 32789
    Single Family
    1. Price: $6,495,000.00
    2. Price sqft: $811.67 / sqft
    3. Previous Price: $6,895,000
    4. Last Price Change: 05/07/26
    5. Days On Market: 199
    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 Middle
    7. High School: Winter Park High
    8. Provided by: FANNIE HILLMAN & ASSOCIATES
    9. mfrmls
    10. DMCA Notice
    Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenues renowned shops, fine dining,
    Listing Details and 75 Additional Pictures
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    1200 Via Salerno
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    Details for 1200 Via Salerno, WINTER PARK, FL 32789
    Single Family
    1. Price: $5,995,000.00
    2. Price sqft: $737.94 / sqft
    3. Previous Price: $6,200,000
    4. Last Price Change: 05/07/26
    5. Days On Market: 85
    6. Bedrooms: 5
    7. Baths: 6
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 8124
    10. Acreage: 0.45 acres
    11. Pool: Yes
    12. Waterfront: No
    13. 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 Middle
    7. High School: Winter Park High
    8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
    9. mfrmls
    10. DMCA Notice
    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
    Listing Details and 46 Additional Pictures
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    2211 Azalea Place
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    Details for 2211 Azalea Place, WINTER PARK, FL 32789
    Single Family
    1. Price: $5,250,000.00
    2. Price sqft: $572.77 / sqft
    3. Previous Price: $5,495,000
    4. Last Price Change: 04/15/26
    5. Days On Market: 320
    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
    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
    Listing Details and 98 Additional Pictures
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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: 01/28/26
    4. Days On Market: 281
    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 Middle
    7. High School: Winter Park High
    8. Provided by: KELLY PRICE & COMPANY LLC
    9. mfrmls
    10. DMCA Notice
    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
    Listing Details and 11 Additional Pictures
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    1441 Cardinal Court
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    Details for 1441 Cardinal Court, WINTER PARK, FL 32789
    Single Family
    1. Price: $4,285,000.00
    2. Price sqft: $772.77 / sqft
    3. Days On Market: 24
    4. Bedrooms: 4
    5. Baths: 6
    6. Garage / Parking Spaces: 2
    7. Bldg sqft: 5545
    8. Acreage: 0.36 acres
    9. Pool: Yes
    10. Waterfront: No
    11. Year Built: 2022
    MLS#: O6399395
    1. County: ORANGE
    2. City: WINTER PARK
    3. Zipcode: 32789
    4. Subdivision: Winflor Court Pt Rep
    5. Elementary School: Dommerich Elem
    6. Middle School: Maitland Middle
    7. High School: Winter Park High
    8. Provided by: CHARLES RUTENBERG REALTY ORLANDO
    9. mfrmls
    10. DMCA Notice
    Beautifully built in 2022 by Lonnie Richardson, this custom one story home sits on a quiet cul de sac in the heart of Winter Park. Designed with a modern, timeless style, it offers luxury finishes pai
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    1161 Valencia Avenue
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    Details for 1161 Valencia Avenue, WINTER PARK, FL 32789
    Single Family
    1. Price: $4,200,000.00
    2. Price sqft: $767.40 / sqft
    3. Previous Price: $4,270,000
    4. Last Price Change: 05/03/26
    5. Days On Market: 262
    6. Bedrooms: 4
    7. Baths: 5
    8. Garage / Parking Spaces: 2
    9. Bldg sqft: 5473
    10. Acreage: 0.32 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: No
    14. Year Built: 2021
    MLS#: O6330736
    1. County: ORANGE
    2. City: WINTER PARK
    3. Zipcode: 32789
    4. Subdivision: Valencia Terrace
    5. Elementary School: Lakemont Elem
    6. Middle School: Maitland Middle
    7. High School: Winter Park High
    8. Provided by: THE REAL ESTATE COLLECTION LLC
    9. mfrmls
    10. DMCA Notice
    Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Completed in 2
    Listing Details and 64 Additional Pictures
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    1782 Pine Avenue
    New Construction
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    Details for 1782 Pine Avenue, WINTER PARK, FL 32789
    Single Family
    1. Price: $4,197,000.00
    2. Price sqft: $624.28 / sqft
    3. Days On Market: 59
    4. Bedrooms: 5
    5. Baths: 7
    6. Garage / Parking Spaces: 4
    7. Bldg sqft: 6723
    8. Acreage: 0.36 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: No
    12. Year Built: 2026
    MLS#: O6389039
    1. County: ORANGE
    2. City: WINTER PARK
    3. Zipcode: 32789
    4. Subdivision: Conwill Estates
    5. Elementary School: Lakemont Elem
    6. Middle School: Maitland Middle
    7. High School: Winter Park High
    8. Provided by: KELLER WILLIAMS ADVANTAGE REALTY
    9. mfrmls
    10. DMCA Notice
    Step into this stunning West Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the heart of City of Winter Park. This
    Listing Details and 65 Additional Pictures
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    Listings provided courtesy of The Hernando County Association of Realtors MLS.
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    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
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    Datafeed Last updated on May 10, 2026 @ 12:00 am
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