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    1. School = Dommerich Elem
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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: 04/16/26
    5. Days On Market: 321
    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
    Listing Details and 98 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: 25
    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
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    1761 Legion Drive
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    Details for 1761 Legion Drive, WINTER PARK, FL 32789
    Single Family
    1. Price: $3,270,000.00
    2. Price sqft: $519.30 / sqft
    3. Previous Price: $3,295,000
    4. Last Price Change: 04/16/26
    5. Days On Market: 332
    6. Bedrooms: 5
    7. Baths: 6
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 6297
    10. Acreage: 0.39 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: No
    14. Year Built: 2017
    MLS#: O6302616
    1. County: ORANGE
    2. City: WINTER PARK
    3. Zipcode: 32789
    4. Subdivision: Green Oaks Rep 02
    5. Elementary School: Dommerich Elem
    6. Middle School: Maitland
    7. High School: Winter Park
    8. Provided by: SCANLON REALTY GROUP LLC
    9. mfrmls
    10. DMCA Notice
    One of the most coveted neighborhoods in all of Winter Park! This custom built 5 bedroom, 5.5 bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and
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    948 Poinciana Lane
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    Details for 948 Poinciana Lane, WINTER PARK, FL 32789
    Single Family
    1. Price: $3,174,000.00
    2. Price sqft: $700.82 / sqft
    3. Previous Price: $3,199,000
    4. Last Price Change: 04/25/26
    5. Days On Market: 118
    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
    Listing Details and 56 Additional Pictures
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    670 Williams Drive
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    Details for 670 Williams Drive, WINTER PARK, FL 32789
    Single Family
    1. Price: $2,895,000.00
    2. Price sqft: $554.92 / sqft
    3. Days On Market: 4
    4. Bedrooms: 5
    5. Baths: 5
    6. Garage / Parking Spaces: 2
    7. Bldg sqft: 5217
    8. Acreage: 0.31 acres
    9. Pool: Yes
    10. Waterfront: No
    11. Year Built: 2016
    MLS#: O6405256
    1. County: ORANGE
    2. City: WINTER PARK
    3. Zipcode: 32789
    4. Subdivision: Park Grove
    5. Elementary School: Dommerich Elem
    6. Middle School: Maitland
    7. High School: Winter Park
    8. Provided by: FANNIE HILLMAN & ASSOCIATES
    9. mfrmls
    10. DMCA Notice
    Graceful and timeless, this classic Southern inspired residence by esteemed builder Charles Clayton sits on a generous lot in Park Groveone of Winter Parks most coveted neighborhoodsand makes a striki
    Listing Details and 57 Additional Pictures
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    620 Pinetree Road
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    Details for 620 Pinetree Road, WINTER PARK, FL 32789
    Land
    1. Price: $2,790,000.00
    2. Days On Market: 31
    3. Acreage: 0.49 acres
    4. Pool: No
    5. Waterfront: No
    6. Year Built: Not Available
    MLS#: O6397264
    1. County: ORANGE
    2. City: WINTER PARK
    3. Zipcode: 32789
    4. Subdivision: Sicilian Shores
    5. Elementary School: Dommerich Elem
    6. Middle School: Maitland
    7. High School: Winter Park
    8. Provided by: FANNIE HILLMAN & ASSOCIATES
    9. mfrmls
    10. DMCA Notice
    One of the last remaining opportunities to build on a truly exceptional street in the Winter Park Vias, this .48 acre homesite offers a fantastic combination of location, scale, and design potential.
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    2412 Chantilly Avenue
    New Construction
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    Details for 2412 Chantilly Avenue, WINTER PARK, FL 32789
    Single Family
    1. Price: $2,394,500.00
    2. Price sqft: $460.84 / sqft
    3. Previous Price: $2,395,000
    4. Last Price Change: 04/21/26
    5. Days On Market: 88
    6. Bedrooms: 5
    7. Baths: 7
    8. Garage / Parking Spaces: 3
    9. Bldg sqft: 5196
    10. Acreage: 0.27 acres
    11. Pool: Yes
    12. Waterfront: No
    13. Year Built: 2026
    MLS#: O6381552
    1. County: ORANGE
    2. City: WINTER PARK
    3. Zipcode: 32789
    4. Subdivision: Winter Park Village
    5. Elementary School: Dommerich Elem
    6. Middle School: Maitland
    7. High School: Winter Park
    8. Provided by: REAL BROKER, LLC
    9. mfrmls
    10. DMCA Notice
    Exceptional design meets refined luxury in this brand new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for bo
    Listing Details and 60 Additional Pictures
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    800 Juanita Rael
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    Details for 800 Juanita Rael, WINTER PARK, FL 32789
    Single Family
    1. Price: $2,300,000.00
    2. Price sqft: $497.41 / sqft
    3. Days On Market: 32
    4. Bedrooms: 5
    5. Baths: 4
    6. Garage / Parking Spaces: 2
    7. Bldg sqft: 4624
    8. Acreage: 0.36 acres
    9. Pool: Yes
    10. Waterfront: No
    11. Year Built: 1961
    MLS#: O6396611
    1. County: ORANGE
    2. City: WINTER PARK
    3. Zipcode: 32789
    4. Subdivision: Green Oaks Rep 02
    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
    Welcome to an exceptional opportunity in the highly desirable Park Grove community, an impeccably updated one story residence ideally situated just moments from the vibrant shops and dining of Park Av
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    1760 Legion Drive
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    Details for 1760 Legion Drive, WINTER PARK, FL 32789
    Single Family
    1. Price: $2,295,000.00
    2. Price sqft: $373.23 / sqft
    3. Previous Price: $2,395,000
    4. Last Price Change: 04/16/26
    5. Days On Market: 81
    6. Bedrooms: 4
    7. Baths: 6
    8. Garage / Parking Spaces: 2
    9. Bldg sqft: 6149
    10. Acreage: 0.34 acres
    11. Pool: Yes
    12. Waterfront: No
    13. Year Built: 1964
    MLS#: O6383603
    1. County: ORANGE
    2. City: WINTER PARK
    3. Zipcode: 32789
    4. Subdivision: Green Oaks 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
    Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location
    Listing Details and 65 Additional Pictures
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    1885 Temple Drive
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    Details for 1885 Temple Drive, WINTER PARK, FL 32789
    Single Family
    1. Price: $2,265,000.00
    2. Price sqft: $504.12 / sqft
    3. Previous Price: $2,295,000
    4. Last Price Change: 03/21/26
    5. Days On Market: 179
    6. Bedrooms: 5
    7. Baths: 4
    8. Garage / Parking Spaces: 2
    9. Bldg sqft: 4493
    10. Acreage: 0.24 acres
    11. Pool: Yes
    12. Waterfront: No
    13. Year Built: 1963
    MLS#: O6359471
    1. County: ORANGE
    2. City: WINTER PARK
    3. Zipcode: 32789
    4. Subdivision: Lugano Terrace
    5. Elementary School: Dommerich Elem
    6. Middle School: Maitland
    7. High School: Winter Park
    8. Provided by: COMPASS FLORIDA LLC
    9. mfrmls
    10. DMCA Notice
    Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5 bedroom, 3.5 bath brick home effortlessly blends timeless charm with extensive
    Listing Details and 52 Additional Pictures
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    Equal Housing Opportunity
    Listings provided courtesy of The Hernando County Association of Realtors MLS.
    Listing Data ©2026 REALTOR® Association of Citrus County
    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.
    Display of MLS data is usually deemed reliable but is NOT guaranteed accurate.
    Datafeed Last updated on May 11, 2026 @ 12:00 am
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