Searching on:
  1. School = Maitland Middle
  2. Listing Status = Active
Details for 887 Georgia Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $5,700,000.00
  2. Price sqft: $843.45 / sqft
  3. Previous Price: $5,900,000
  4. Last Price Change: 01/26/26
  5. Days On Market: 190
  6. Bedrooms: 6
  7. Baths: 6
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 6758
  10. Acreage: 1.07 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1924
MLS#: O6331715
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Dyer Susan Resub
  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
Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1 acre lot. Exuding timeless
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: 12/07/25
  5. Days On Market: 228
  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
Details for 1302 Raintree Place, WINTER PARK, FL 32789
Single Family
  1. Price: $5,150,000.00
  2. Price sqft: $872.00 / sqft
  3. Previous Price: $5,300,000
  4. Last Price Change: 01/13/26
  5. Days On Market: 113
  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 Middle
  7. High School: Winter Park High
  8. Provided by: FANNIE HILLMAN & ASSOCIATES
  9. mfrmls
  10. DMCA Notice
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.
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: 01/30/26
  5. Days On Market: 351
  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 Middle
  7. High School: Winter Park High
  8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
  9. mfrmls
  10. DMCA Notice
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
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: 222
  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 Middle
  7. High School: Winter Park High
  8. Provided by: KELLY PRICE & COMPANY LLC
  9. mfrmls
  10. DMCA Notice
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
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: 188
  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
Details for 1417 Williams Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $4,199,000.00
  2. Price sqft: $682.76 / sqft
  3. Days On Market: 23
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6150
  8. Acreage: 0.37 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2026
MLS#: O6368668
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Park Grove
  5. Elementary School: Dommerich Elem
  6. Middle School: Maitland Middle
  7. High School: Winter Park High
  8. Provided by: ONE LUXURY INTERNATIONAL LLC
  9. mfrmls
  10. DMCA Notice
Under Construction. Tucked away on a quiet cul de sac in the coveted Park Grove community, this home sits on an expansive 0.37 acre lot, just moments from the boutiques, dining, and charm of Park Aven
Details for 1250 Maitland Avenue, MAITLAND, FL 32751
Land
  1. Price: $3,990,900.00
  2. Previous Price: $4,490,900
  3. Last Price Change: 10/23/25
  4. Days On Market: 559
  5. Acreage: 7.82 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Lake Front
  10. Year Built: Not Available
MLS#: O6222186
  1. County: ORANGE
  2. City: MAITLAND
  3. Zipcode: 32751
  4. Subdivision: Woodbridge
  5. Elementary School: Lake Sybelia Elem
  6. Middle School: Maitland Middle
  7. High School: Edgewater High
  8. Provided by: AG REALTY SERVICES LLC
  9. mfrmls
  10. DMCA Notice
Exceptional opportunity for commercial developers, residential builders, or those seeking a private estate within the City of Maitland, Orange County. This rare offering includes approximately 8 acres
Details for 948 Poinciana Lane, WINTER PARK, FL 32789
Single Family
  1. Price: $3,599,000.00
  2. Price sqft: $794.66 / sqft
  3. Days On Market: 24
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4529
  8. Acreage: 0.30 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. 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 Middle
  7. High School: Winter Park High
  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
Details for 127 Whitecaps Circle, MAITLAND, FL 32751
Land
  1. Price: $3,425,000.00
  2. Previous Price: $3,495,000
  3. Last Price Change: 01/30/26
  4. Days On Market: 27
  5. Acreage: 0.56 acres
  6. Pool: No
  7. Waterfront: Yes
  8. Wateraccess: Yes
  9. Waterfront Type: Lake Privileges
  10. Year Built: Not Available
MLS#: O6367169
  1. County: ORANGE
  2. City: MAITLAND
  3. Zipcode: 32751
  4. Elementary School: Dommerich Elem
  5. Middle School: Maitland Middle
  6. High School: Winter Park High
  7. Provided by: PREMIER SOTHEBY'S INTL. REALTY
  8. mfrmls
  9. DMCA Notice
A rare opportunity to secure a Lake Maitland homesite on the desired MaitlandWinter Park Chain of Lakes, an increasingly limited offering as quality lakefront parcels continue to disappear. Along a qu