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    1. City = Winter Park
    2. Listing Status = Active
    Details for 1120 Preserve Point Drive, WINTER PARK, FL 32789
    Single Family
    1. Price: $8,950,000.00
    2. Price sqft: $669.06 / sqft
    3. Days On Market: 214
    4. Bedrooms: 7
    5. Baths: 11
    6. Garage / Parking Spaces: 4
    7. Bldg sqft: 13377
    8. Acreage: 1.63 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: Yes
    12. Wateraccess: Yes
    13. Waterfront Type: Lake Front
    14. Year Built: 2009
    MLS#: O6350054
    1. County: ORANGE
    2. City: WINTER PARK
    3. Zipcode: 32789
    4. Subdivision: Windsongpreserve Point
    5. Elementary School: Brookshire Elem
    6. Middle School: Glenridge
    7. High School: Winter Park
    8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
    9. mfrmls
    10. DMCA Notice
    In the exclusive community of Windsong on Lake Berry, this magnificent 1.6 acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped
    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: 88
    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
    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
    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: 65
    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
    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
    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: 04/11/26
    5. Days On Market: 198
    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
    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,
    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: $6,450,000
    4. Last Price Change: 04/23/26
    5. Days On Market: 84
    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
    7. High School: Winter Park
    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
    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: 04/16/26
    5. Days On Market: 319
    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
    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: 279
    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
    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
    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: 23
    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
    7. High School: Winter Park
    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
    Details for 1298 Beachview Avenue, WINTER PARK, FL 32789
    Land
    1. Price: $4,200,000.00
    2. Days On Market: 2
    3. Acreage: 0.34 acres
    4. Pool: No
    5. Waterfront: Yes
    6. Wateraccess: Yes
    7. Waterfront Type: Lake Front
    8. Year Built: Not Available
    MLS#: O6405064
    1. County: ORANGE
    2. City: WINTER PARK
    3. Zipcode: 32789
    4. Subdivision: Killarney Estates
    5. Provided by: PREMIER SOTHEBYS INT'L REALTY
    6. mfrmls
    7. DMCA Notice
    This is a rare Lake Killarney portfolio offering of four parcels in Winter Park. An exceptional opportunity to acquire a four parcel assemblage in one of Winter Parks most coveted locations, just mome
    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: 05/04/26
    5. Days On Market: 260
    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
    7. High School: Winter Park
    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
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