Searching on:
  1. City = Winter Park
  2. Listing Status = Active
Details for 570 Manor Road Maitland, Winter Park, FL 32751
Single Family
  1. Price: $12,500,000.00
  2. Days On Market: 447
  3. Bedrooms: 6
  4. Baths: 10
  5. Garage / Parking Spaces: 6
  6. Acreage: 0.00 acres
  7. Pool: Yes
  8. Waterfront: No
  9. Year Built: 1996
MLS#: A11776219
  1. County: Orange
  2. City: Winter Park
  3. Zipcode: 32751
  4. Subdivision: Lake Maitland Manor
  5. Provided by: Fortune Christie's International Real Estate
  6. Provided through
  7. DMCA Notice
Lakefront estate featuring 6 bed, 7 full and 3 half baths. over 11,000 SqFt on 2,7 acres. Resort style pool, summer kitchen, 6 car garage, fully fenced with a private gate. 120 feet of lake front on W
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: 275
  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: 148
  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
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: 126
  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
Details for 2661 Via Tuscany, Winter Park, FL 32789
Single Family
  1. Price: $6,888,888.00
  2. Price sqft: $1,485.96 / sqft
  3. Days On Market: 51
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4636
  8. Acreage: 0.00 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2024
MLS#: B26030158
  1. County: Orange
  2. City: Winter Park
  3. Zipcode: 32789
  4. Subdivision: Winter Park
  5. Provided by: The Keyes Company
  6. REALTORS® Association of the Palm Beaches, Inc
  7. DMCA Notice
Set in the perfect Winter Park location, within exclusive Via Tuscany, this unique, RESILIENT CONSTRUCTION residence built by Developer & Builder Group, offers a rare blend of enduring quality, refine
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: 258
  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 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 1571 Woodland Avenue, WINTER PARK, FL 32789
Single Family
  1. Price: $6,000,000.00
  2. Price sqft: $624.02 / sqft
  3. Days On Market: 40
  4. Bedrooms: 5
  5. Baths: 8
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 9615
  8. Acreage: 0.38 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2007
MLS#: O6411706
  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: CHARLES RUTENBERG REALTY ORLANDO
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Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one of a kind exceptional estate offers more than 7,300 square feet across three beautifully d
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: 05/08/26
  5. Days On Market: 144
  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 2228 Azalea Place, WINTER PARK, FL 32789
Single Family
  1. Price: $5,600,000.00
  2. Price sqft: $826.57 / sqft
  3. Days On Market: 11
  4. Bedrooms: 5
  5. Baths: 6
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 6775
  8. Acreage: 0.33 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2008
MLS#: O6416342
  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: COMPASS FLORIDA LLC
  9. mfrmls
  10. DMCA Notice
This elegant transitional French Provincial residence is located on a large, elevated corner lot in a quiet and secluded area in the Vias of Winter Park. This residence has been significantly enhanced
Details for 313 Sylvan Drive, WINTER PARK, FL 32789
Single Family
  1. Price: $5,500,000.00
  2. Price sqft: $963.73 / sqft
  3. Days On Market: 22
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5707
  8. Acreage: 0.37 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Front
  13. Year Built: 2027
MLS#: O6407606
  1. County: ORANGE
  2. City: WINTER PARK
  3. Zipcode: 32789
  4. Subdivision: Sylvan Park
  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
Pre Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37 acre (16,603 square foot) homesite, presents a rare opportunity to own a thoughtfully curat