$250,000
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
1500 Gay Rd Unit 3C, Winter Park, FL 32789
Heather Frazee FANNIE HILLMAN & ASSOCIATES
28,402
Winter Park, FL Homes
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1500 Gay Rd Unit 3C, Winter Park, FL 32789
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$2,700 Per Month
- 3 Beds
- 2.5 Baths
- 1,907 Sq Ft
- Townhouse for Rent
2817 Bright Bird Ln, Winter Park, FL 32792
2817 Bright Bird Ln, Winter Park, FL 32792Welcome to Grayson Square in Winter Park. This beautifully maintained 3-bedroom, 2.5-bath townhome is located in one of the area’s newer gated communities and shows like new throughout. Exceptionally clean and well cared for, this home is truly move-in ready. The open-concept living and dining area offers a comfortable layout for both everyday living and entertaining. The covered lanai overlooks
Denise Del Castillo LPT REALTY, LLC
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$567,500
Sold Dec 09, 20251010 Aragon Ave, Winter Park, FL 32789
- 3 Beds
- 2 Baths
- 1,453 Sq Ft
- Built 1949
Last Sold Summary
- 1% Below List Price
- $391/SF
- 2 Days On Market
Current Estimated Value $572,260
Last Listing Agent Devin Loh COLDWELL BANKER REALTY
1010 Aragon Ave, Winter Park, FL 32789 -
Est $819,938
Not Listed For Sale1770 Mondrian Cir, Winter Park, FL 32789
- 3 Beds
- 3.5 Baths
- 2,193 Sq Ft
- Built 2023
Last Sold Summary
- 18 Days On Market
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$600,000
$100K PRICE DROP Pending- 3 Beds
- 2.5 Baths
- 2,150 Sq Ft
661 Selkirk Dr, Winter Park, FL 32792
661 Selkirk Dr, Winter Park, FL 32792David Miller KELLER WILLIAMS HERITAGE REALTY
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$1,500 Per Month
- 2 Beds
- 1 Bath
- 754 Sq Ft
- HC - Goldenrod Road
4616 N Goldenrod Rd Unit 4616 N Goldenrod Rd, Winter Park, FL 32792
4616 N Goldenrod Rd Unit 4616 N Goldenrod Rd, Winter Park, FL 32792 -
$2,078,500
Sold Dec 11, 2025715 Via Bella, Winter Park, FL 32789
- 5 Beds
- 4 Baths
- 4,328 Sq Ft
- Built 1976
Last Sold Summary
- 12% Below List Price
- $480/SF
- 70 Days On Market
Current Estimated Value $2,150,831
Last Listing Agent Adam Roark COMPASS FLORIDA LLC
715 Via Bella, Winter Park, FL 32789 -
Not Listed For Sale
0 Grand Rd Unit MFRO6169911, Winter Park, FL 32792
Last Sold Summary
- 73 Days On Market
-
$1,800,000
$170K PRICE DROP Pending- 5 Beds
- 4.5 Baths
- 4,363 Sq Ft
1177 Kenwood Ave, Winter Park, FL 32789
1177 Kenwood Ave, Winter Park, FL 32789Karen Albright OPENDOOR BROKERAGE LLC
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$1,295 Per Month
- 1 Bed
- 1 Bath
- 809 Sq Ft
- Condo for Rent
7425 Daniel Webster Dr Unit B-11, Winter Park, FL 32792
7425 Daniel Webster Dr Unit B-11, Winter Park, FL 32792Discover this large first-level one-bedroom, one-bath condo in Winter Park. The unit features new cabinets and appliances, a remodeled bathroom, and new laminated flooring throughout. Enjoy a spacious bedroom with a bay window that brings in natural light, plus a covered tiled patio for outdoor seating.Washer and Dryer inside for convenience. The community offers a pool for residents.
Celimar Sierra, LLC PREMIUM PROPERTIES R.E SERVICE
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$250,000
Sold Mar 11, 20262009 Cornell Ave, Winter Park, FL 32789
- 2 Beds
- 1 Bath
- 762 Sq Ft
- Built 1940
Last Sold Summary
- 7% Below List Price
- $328/SF
- 95 Days On Market
Current Estimated Value $267,851
Last Listing Agent Juliet Saldarriaga ORLANDO HOME DEALER LLC
2009 Cornell Ave, Winter Park, FL 32789 -
Est $101,754
Not Listed For Sale7453 Daniel Webster Dr Unit D, Winter Park, FL 32792
- 1 Bed
- 1 Bath
- 786 Sq Ft
- Built 1974
Last Sold Summary
- 4 Days On Market
-
$999,000
$201K PRICE DROP- 3 Beds
- 2.5 Baths
- 2,304 Sq Ft
241 W Lake Sue Ave, Winter Park, FL 32789
241 W Lake Sue Ave, Winter Park, FL 32789Ken Dalton COLDWELL BANKER REALTY
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$1,950 Per Month
- 2 Beds
- 2 Baths
- 1,058 Sq Ft
- House for Rent
4800 Tangerine Ave, Winter Park, FL 32792
4800 Tangerine Ave, Winter Park, FL 32792Beautiful & Spacious 2-Bedroom, 2-Bath Condo for Rent in Winter Park – $1,950/MonthDiscover the perfect blend of comfort, convenience, and lifestyle in this beautifully maintained condo located in the highly desirable Winter Park area. This home offers an exceptional layout with 2 spacious bedrooms and 2 full bathrooms, ideal for families, professionals, or roommates seeking a comfortable and
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$375,000
Sold Mar 06, 20261007 Early Ave, Winter Park, FL 32789
- 3 Beds
- 2 Baths
- 1,721 Sq Ft
- Built 1956
Last Sold Summary
- 12% Below List Price
- $218/SF
- 101 Days On Market
Current Estimated Value $382,604
Last Listing Agent Eric Gross EXP REALTY LLC
1007 Early Ave, Winter Park, FL 32789 -
Est $435,200
Not Listed For Sale2778 Bright Bird Ln, Winter Park, FL 32792
- 3 Beds
- 2.5 Baths
- 1,907 Sq Ft
- Built 2024
Last Sold Summary
- 1 Day On Market
-
$2,394,500
New Construction Pending- 5 Beds
- 6.5 Baths
- 4,506 Sq Ft
2412 Chantilly Ave, Winter Park, FL 32789
2412 Chantilly Ave, Winter Park, FL 32789Tab Bish LLC REAL BROKER, LLC
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$2,050 Per Month
- 2 Beds
- 1 Bath
- 1,125 Sq Ft
- House for Rent
503 Kilshore Ln, Winter Park, FL 32789
503 Kilshore Ln, Winter Park, FL 32789LOCATION! LOCATION! LOCATION! Home well positioned on large 0.28 acre lot in 32789. Gorgeous two bedroom home right in the heart of Winter Park , that just had a new roof put on.. At just a ten minute drive from Orlando, this home is in a very convenient location for anyone who wants to be in and out of the city whenever they'd like. Beautiful interior, with original wood flooring throughout.
Vincent Paige, PA COLDWELL BANKER REALTY
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$434,000
Sold Sep 12, 20251122 Washington Ave Unit 7, Winter Park, FL 32789
- 2 Beds
- 2.5 Baths
- 1,556 Sq Ft
- Built 1978
Last Sold Summary
- 2% Above List Price
- $279/SF
- 55 Days On Market
Current Estimated Value $465,911
Last Listing Agent Raul Veitia BELMONT REALTY
1122 Washington Ave Unit 7, Winter Park, FL 32789 -
Est $455,691
Not Listed For Sale2774 Bright Bird Ln, Winter Park, FL 32792
- 3 Beds
- 2.5 Baths
- 1,907 Sq Ft
- Built 2024
-
$324,000
$15K PRICE DROP- 3 Beds
- 2 Baths
- 1,160 Sq Ft
1760 Peruvian Ln, Winter Park, FL 32792
1760 Peruvian Ln, Winter Park, FL 32792Moe Mossa SAVVY AVENUE, LLC
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$1,495 Per Month
- 2 Beds
- 2 Baths
- 756 Sq Ft
- Condo for Rent
7302 Swallow Run Unit 7302, Winter Park, FL 32792
7302 Swallow Run Unit 7302, Winter Park, FL 32792AVAILABLE NOW! Please call or text to schedule a showing. This 2 bedroom, 2 bathroom condo is located in Winter Park's Whisperwood community near local shops, restaurants, and schools. Features include a spacious living area with dining room, lovely kitchen with granite countertops, a wonderful primary suite, and outdoor patio. Community amenities include a swimming pool. Pets under 35
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$850,000
Sold Mar 25, 2026465 N Phelps Ave, Winter Park, FL 32789
- Land
- 11,761 Sq Ft
- $3,148,148 per Acre
Last Sold Summary
- 7 Days On Market
Current Estimated Value $834,246
Last Listing Agent Hircanys Vicioso FIDICITY REALTY INC
465 N Phelps Ave, Winter Park, FL 32789 -
Est $549,639
Not Listed For Sale8097 Pleasant Pine Cir, Winter Park, FL 32792
- 4 Beds
- 2 Baths
- 2,003 Sq Ft
- Built 2015
Last Sold Summary
- 2 Days On Market
-
$879,000
- 3 Beds
- 3.5 Baths
- 2,030 Sq Ft
1265 Arlington Place, Winter Park, FL 32789
1265 Arlington Place, Winter Park, FL 32789Erika Beerbower FANNIE HILLMAN & ASSOCIATES
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$1,750 Per Month
- 2 Beds
- 1 Bath
- 854 Sq Ft
- Condo for Rent
2304 Inagua Way Unit 2304, Winter Park, FL 32792
2304 Inagua Way Unit 2304, Winter Park, FL 32792Welcome to this charming 2 bedroom, 1 bathroom corner unit in Winter Park, FL. This single-story home features ceramic tile flooring throughout, perfect for easy maintenance. The freshly painted interior complements the renovated kitchen and bathroom, giving the space a modern and updated feel. Enjoy the privacy of the fenced backyard, ideal for outdoor entertaining or relaxing. Located in the
Francisco Nieves-Taranto CT HOMES REALTY CORPORATION
-
$505,000
Sold Aug 01, 2025715 Roughbeard Rd, Winter Park, FL 32792
- 4 Beds
- 2 Baths
- 2,250 Sq Ft
- Built 1968
Last Sold Summary
- 12% Below List Price
- $224/SF
- 60 Days On Market
Current Estimated Value $565,239
Last Listing Agent Christine Gerardi NEXTHOME DIAMOND PROPERTIES
715 Roughbeard Rd, Winter Park, FL 32792 -
Est $187,807
Not Listed For Sale3378 Cedar Springs Place Unit 154, Winter Park, FL 32792
- 2 Beds
- 2.5 Baths
- 1,031 Sq Ft
- Built 1984
Last Sold Summary
- 132 Days On Market
-
$444,900
$5K PRICE DROP- 3 Beds
- 2.5 Baths
- 1,782 Sq Ft
1951 Canny Cove, Winter Park, FL 32792
1951 Canny Cove, Winter Park, FL 32792Denise Del Castillo LPT REALTY, LLC
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$2,595 Per Month
- 3 Beds
- 2.5 Baths
- 1,907 Sq Ft
- Townhouse for Rent
2887 Clever Ln, Winter Park, FL 32792
2887 Clever Ln, Winter Park, FL 32792Welcome home to 2887 Clever Lane, a three bedroom, two and a half bath town home with a one car garage! The kitchen overlooks the main living area and features a full suite of stainless steel appliances including the refrigerator, range, over the range microwave and dishwasher as well as plenty of cabinetry and counter top space. The half bath is located on the first floor, easily accessible for
-
$252,500
Sold Jul 17, 20252309 Sun Valley Cir, Winter Park, FL 32792
- 2 Beds
- 2 Baths
- 1,669 Sq Ft
- Built 1985
Last Sold Summary
- 11% Below List Price
- $151/SF
- 65 Days On Market
Current Estimated Value $262,325
Last Listing Agent Kristin Vogt PLLC KGV REALTY GROUP
2309 Sun Valley Cir, Winter Park, FL 32792 -
Est $437,997
Not Listed For Sale2726 Bright Bird Ln, Winter Park, FL 32792
- 3 Beds
- 2.5 Baths
- 1,907 Sq Ft
- Built 2023
Last Sold Summary
-
$6,950,000
New Construction- 5 Beds
- 5.5 Baths
- 5,905 Sq Ft
40 Palmer Ave, Winter Park, FL 32789
40 Palmer Ave, Winter Park, FL 32789Julie Christensen ONE LUXURY INTERNATIONAL LLC
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$3,060 Per Month
- 3 Beds
- 2.5 Baths
- 1,700 Sq Ft
- Townhouse for Rent
1415 Harmon Ave, Winter Park, FL 32789
1415 Harmon Ave, Winter Park, FL 32789In the heart of Winter Park on a quiet cobbled street, this Mediterranean style 3-bedroom, 3-bathroom house is available to rent today. With beautiful Travertine floors throughout the downstairs of the home, granite countertop kitchen, marble countertop bathrooms, and limestone ornate pillars throughout the home, this home boasts character. Upstairs the home enjoys three bedrooms, two bathrooms,
Moire McKibbin LA ROSA REALTY ORLANDO LLC
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$445,000
Sold Jun 04, 20261832 E Cheryl Dr, Winter Park, FL 32792
- 4 Beds
- 2 Baths
- 1,808 Sq Ft
- Built 1983
Last Sold Summary
- 3% Above List Price
- $246/SF
- 6 Days On Market
Current Estimated Value $437,334
Last Listing Agent Shanon Luiz SELECTIVE REALTY GROUP LLC
1832 E Cheryl Dr, Winter Park, FL 32792 -
Est $2,025,887
Not Listed For Sale1925 Killarney Dr, Winter Park, FL 32789
Last Sold Summary
- 33 Days On Market
-
$465,000
- 4 Beds
- 2.5 Baths
- 1,903 Sq Ft
8433 Commander Cove, Winter Park, FL 32792
8433 Commander Cove, Winter Park, FL 32792Brandi Cepeda CEPEDA REAL ESTATE LLC
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$5,500 Per Month
- 4 Beds
- 3 Baths
- 2,511 Sq Ft
- Hidden Winter Park Oasis
610 Gaines Way, Winter Park, FL 32789
610 Gaines Way, Winter Park, FL 32789Tucked away at the quiet end of a private cul-de-sac in Winter Park’s premier 32789 zip code, this exceptional property blends classic elegance with a bright, modern lifestyle. From the gleaming wood floors that flow throughout the entire home to the thoughtful architectural details, this residence is designed for those who appreciate both privacy and top-tier entertaining.The Interior
-
$268,000
Sold Feb 24, 2026609 Gallery Dr Unit 204, Winter Park, FL 32792
- 2 Beds
- 2 Baths
- 893 Sq Ft
- Built 1984
Last Sold Summary
- 10% Below List Price
- $300/SF
- 99 Days On Market
Current Estimated Value $255,023
Last Listing Agent Olga Ray A2Z REALTY GROUP
609 Gallery Dr Unit 204, Winter Park, FL 32792 -
Est $365,222
Not Listed For Sale7494 Aloma Pines Ct, Winter Park, FL 32792
- 3 Beds
- 2.5 Baths
- 1,872 Sq Ft
- Built 2017
Last Sold Summary
- 112 Days On Market
Showing Results 521 - 560, Page 14 of 18
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