Winter Park, FL Homes

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  $179,900

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  200 Saint Andrews Blvd Unit 1905, Winter Park, FL 32792

  A Wonderful Opportunity Awaits!! Discover the ease of low-maintenance living in this well-maintained GROUND-FLOOR unit in the always-popular Four Seasons community. Currently leased for $1,800/month to an excellent tenant who would love to stay (month-to-month with 60-day notice), this condo offers built-in stability for investors or a smooth transition for future owner-occupants. Inside, enjoy

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  200 Saint Andrews Blvd Unit 1905, Winter Park, FL 32792
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  /18

  $2,625 per month

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • House for Rent

  6877 Jackman Blvd, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2769.90. That covers your base rent, $2625.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  6877 Jackman Blvd, Winter Park, FL 32792
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  $400,000 Sold May 29, 2025

  5144 Goldenrod Place Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Built 1972

  Last Sold Summary

  • 6% Below List Price
  • $273/SF
  • 36 Days On Market

  Current Estimated Value $404,201

  Last Listing Agent Rebecca Sparks C. APOLLO REALTY INC

  5144 Goldenrod Place Rd, Winter Park, FL 32792
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  /39

  Est $871,351 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft

  1770 Mondrian Cir, Winter Park, FL 32789

  1770 Mondrian Cir, Winter Park, FL 32789
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  /21

  $139,900

  • 2 Beds
  • 2 Baths
  • 1,030 Sq Ft

  3053 George Mason Ave Unit 8, Winter Park, FL 32792

  Updated 2-bedroom, 2-bath condo featuring modern finishes throughout! This condo features laminate floors, sleek granite countertops, and stainless steel appliances in the kitchen. A rare find with an in-unit washer and dryer for added convenience. Step out onto the brand new deck, upgraded with durable composite decking—perfect for relaxing or entertaining. Ideally located just minutes from Full

  Daniel Graves GRAVES REALTY

  3053 George Mason Ave Unit 8, Winter Park, FL 32792
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  /17

  $3,195 per month

  • 3 Beds
  • 2.5 Baths
  • 1,775 Sq Ft
  • Condo for Rent

  2238 Hawick Ln, Winter Park, FL 32792

  This delightful 3-bedroom, 2.5-bathroom condo is available for lease in the heart of Winter Park. Step inside to an open floor plan that exudes warmth and sophistication. The first level boasts high ceilings and chic tile floors, perfect for showcasing your unique style. The kitchen invites culinary adventures with its solid wood cabinets, granite countertops, stainless steel appliances, and a

  Brian Rotenberger COMPASS FLORIDA LLC

  2238 Hawick Ln, Winter Park, FL 32792
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  /2

  $468,470 Sold Jun 20, 2025

  1026 Manchester Cir, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • Built 1977

  Last Sold Summary

  • 3% Below List Price
  • $272/SF
  • 25 Days On Market

  Current Estimated Value $474,621

  Last Listing Agent David Miller KELLER WILLIAMS HERITAGE REALTY

  1026 Manchester Cir, Winter Park, FL 32792
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  Est $1,063,648 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft

  1768 Mondrian Cir, Winter Park, FL 32789

  1768 Mondrian Cir, Winter Park, FL 32789
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  /11

  $440,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,355 Sq Ft

  1909 Edwin Blvd, Winter Park, FL 32792

  The house is located in great location and features 3 bedrooms, 2 bathrooms. It sits on a corner lot and offers high ceilings throughout.

  Thu Nguyen CHARLES RUTENBERG REALTY ORLANDO

  1909 Edwin Blvd, Winter Park, FL 32792
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  $2,695 per month

  • 3 Beds
  • 2.5 Baths
  • 1,886 Sq Ft
  • Townhouse for Rent

  7518 Aloma Pines Ct, Winter Park, FL 32792

  Welcome to 7518 Aloma Pines Ct, a modern 3-bedroom, 2.5-bath townhome in the heart of Winter Park, FL. Set in a quiet, gated community, this 1,872 sq ft residence blends upscale living with smart home features — including a built-in 5.1 surround sound system for a theater-quality experience.Interior Highlights:•Chef’s kitchen with granite countertops, 42” wood cabinetry, stainless

  7518 Aloma Pines Ct, Winter Park, FL 32792
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  $430,000 Sold Aug 08, 2025

  1006 Bradford Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,130 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Above List Price
  • $202/SF
  • 7 Days On Market

  Current Estimated Value $431,297

  Last Listing Agent Paul Giannotti TERZA REAL ESTATE

  1006 Bradford Dr, Winter Park, FL 32792
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  Not Listed For Sale

  0 Grand Rd Unit MFRO6169911, Winter Park, FL 32792

  0 Grand Rd Unit MFRO6169911, Winter Park, FL 32792
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  $1,750,000

  • 3 Beds
  • 4.5 Baths
  • 3,164 Sq Ft

  1630 Chestnut Ave, Winter Park, FL 32789

  Discover a fresh take on modern living in one of Winter Park's most admired neighborhoods - the "Tree Streets." This custom three-story LunDev home marries modern minimalism with subtle Dutch Colonial influences, creating a distinctive and inviting retreat. The carefully curated neutral palette sets a relaxed tone throughout, blending timeless design elements with contemporary

  Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1630 Chestnut Ave, Winter Park, FL 32789
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  $5,400 per month

  • 4 Beds
  • 3 Baths
  • 2,841 Sq Ft
  • House for Rent

  1701 Palmer Ave, Winter Park, FL 32789

  Winter Park– Prime 32789 Location!Live in style in this spacious 4-bedroom, 3-bath home with a private pool, just steps from Phelps Park and minutes from Park Avenue dining, shopping, and Rollins College.Enjoy bright open living spaces, a large kitchen with wood cabinetry and wine fridge, and French doors leading to a courtyard and pool area — perfect for entertaining or relaxing.

  Rhonda Fisher TRUST EQUITY GROUP LLC

  1701 Palmer Ave, Winter Park, FL 32789
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  $1,242,000 Sold Feb 07, 2025

  335 W Welbourne Ave Unit 103, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,734 Sq Ft
  • Built 2008

  Last Sold Summary

  • 14% Below List Price
  • $454/SF
  • 184 Days On Market

  Current Estimated Value $1,241,199

  Last Listing Agent Gernelle Bokuniewicz LIVELY REAL ESTATE

  335 W Welbourne Ave Unit 103, Winter Park, FL 32789
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  /2

  Est $107,346 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 786 Sq Ft

  7453 Daniel Webster Dr Unit D, Winter Park, FL 32792

  7453 Daniel Webster Dr Unit D, Winter Park, FL 32792
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  $449,900

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  1951 Canny Cove, Winter Park, FL 32792

  Discover comfortable Winter Park living in this bright and stylish 3-bedroom, 2.5-bathroom corner-unit townhome located in the gated Grayson Square community. Abundant natural light fills the open-concept living area, which flows seamlessly to a covered lanai that’s perfect for relaxing mornings or quiet evenings. The modern kitchen includes stainless steel appliances, quartz countertops, and

  Denise Del Castillo LPT REALTY, LLC

  1951 Canny Cove, Winter Park, FL 32792
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  /27

  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft
  • Condo for Rent

  2500 Lee Rd Unit 212, Winter Park, FL 32789

  Welcome to Lakeside Manor on beautiful Lake Killarney! This charming 2 bedroom, 1 bathroom second-floor condo offers tranquil living in one of Central Florida’s most desirable areas. Enjoy a serene, park-like setting right outside your door and access to breathtaking sunset views from the private community dock.Just minutes from Park Ave, Rollins College, Mills District, top dining,

  2500 Lee Rd Unit 212, Winter Park, FL 32789
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  $715,000 Sold Jan 24, 2025

  2235 Coldstream Dr, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,347 Sq Ft
  • Built 2003

  Last Sold Summary

  • 13% Below List Price
  • $305/SF
  • 120 Days On Market

  Current Estimated Value $744,624

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  2235 Coldstream Dr, Winter Park, FL 32792
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  /18

  Est $413,238 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2778 Bright Bird Ln, Winter Park, FL 32792

  2778 Bright Bird Ln, Winter Park, FL 32792
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  $1,999,000

  • 5 Beds
  • 3.5 Baths
  • 3,423 Sq Ft

  1540 Palm Ave, Winter Park, FL 32789

  Welcome to this stunning SINGLE STORY five-bedroom home with high ceilings, in one of Winter Park’s most desirable neighborhoods, where charming restorations and luxury new builds create a vibrant community feel. Designed with both beauty and comfort in mind, this open-concept home offers bright, welcoming living spaces and thoughtful upgrades throughout. Completely rebuilt in 2014 and tons of

  John McDade FANNIE HILLMAN & ASSOCIATES

  1540 Palm Ave, Winter Park, FL 32789
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  /22

  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 1,090 Sq Ft
  • House for Rent

  1613 Winter Green Blvd, Winter Park, FL 32792

  Feel right at home in this cozy single-family gem located in one of the most sought-after communities! Bright, open living spaces make it perfect for family time and entertaining. Enjoy a peaceful backyard and amazing community amenities — including a pool, and recreation areas for everyone to enjoy. Close to great schools, restaurants, and shopping, this home offers comfort, convenience, and a

  Edgard Rodriguez CENTRAL FLORIDA GROUP REALTY LLC

  1613 Winter Green Blvd, Winter Park, FL 32792
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  $1,595,000 Sold Sep 02, 2025

  1733 Harmon Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,267 Sq Ft
  • Built 2025

  Last Sold Summary

  • $488/SF
  • 27 Days On Market

  Current Estimated Value $1,568,298

  Last Listing Agent Jordan Freeland SOUTH REALTY, INC

  1733 Harmon Ave, Winter Park, FL 32789
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  /29

  Est $559,091 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,003 Sq Ft

  8097 Pleasant Pine Cir, Winter Park, FL 32792

  8097 Pleasant Pine Cir, Winter Park, FL 32792
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  /53

  $2,775,000

  • 5 Beds
  • 5 Baths
  • 4,026 Sq Ft

  2503 Versailles Ave, Winter Park, FL 32789

  Beautifully updated and offered for the first time, this 2015 David Weekley home sits on a rare cul-de-sac in the heart of Winter Park, zoned for Dommerich Elementary and Winter Park schools. This 5-bedroom, 5-bath home features an office, large bonus room, covered lanai with full summer kitchen, and a backyard putting green. Additional highlights include a 3-car garage, a gated parking pad ideal

  Sarah Tomlinson COMPASS FLORIDA LLC

  2503 Versailles Ave, Winter Park, FL 32789
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  /19

  $1,000 per month

  • 1 Bed
  • 1 Bath
  • 408 Sq Ft
  • House for Rent

  5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792

  Attention Full Sail and UCF Students! This is the place for which you've been looking. This is a shared living space that is fully furnished with all utilities included. Each of the 4 rooms has its own electronic keypad lock for your privacy and security. The extra large common areas provide the perfect space for dining and living. Spacious laundry and kitchen provide you with plenty of space

  5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792
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  $749,000 Sold Aug 13, 2025

  627 Darcey Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,509 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Below List Price
  • $299/SF
  • 52 Days On Market

  Current Estimated Value $750,569

  Last Listing Agent Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

  627 Darcey Dr, Winter Park, FL 32792
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  /16

  Est $191,593 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft

  3378 Cedar Springs Place Unit 154, Winter Park, FL 32792

  3378 Cedar Springs Place Unit 154, Winter Park, FL 32792
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  $1,525,000

  • 4 Beds
  • 4 Baths
  • 3,237 Sq Ft

  1408 Chapman Cir, Winter Park, FL 32789

  Nestled in the Elizabeth’s Walk subdivision in the highly desirable Windsong community of Winter Park, this renovated four-bedroom, four-bathroom pool home offers exceptional privacy and refined updates. Quiet interior street and mature landscaping the home feels secluded. Recent improvements include a new roof (2023), two new AC systems 4-ton Carrier Infinity downstairs and a 2.5-ton Trane

  Jennifer Sloan COMPASS FLORIDA LLC

  1408 Chapman Cir, Winter Park, FL 32789
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  /57

  $3,225 per month

  • 3 Beds
  • 2 Baths
  • 1,436 Sq Ft
  • House for Rent

  1835 Edwin Blvd, Winter Park, FL 32789

  Welcome to this charming bungalow located near the historic district of Winter Park, FL. This home boasts three spacious bedrooms and two fully renovated bathrooms, featuring beautiful tile finishes. The kitchen is a chef's dream with stainless steel appliances, granite countertops, travertine floors and a modern design. The living room and bedrooms are adorned with beautiful wood flooring,

  Francisco Nieves-Taranto CT HOMES REALTY CORPORATION

  1835 Edwin Blvd, Winter Park, FL 32789
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  $380,000 Sold May 02, 2025

  350 Killarney Bay Ct Unit 5, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,428 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $266/SF
  • 42 Days On Market

  Current Estimated Value $390,177

  Last Listing Agent Dora Siler FOLIO REALTY LLC

  350 Killarney Bay Ct Unit 5, Winter Park, FL 32789
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  Est $442,767 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2726 Bright Bird Ln, Winter Park, FL 32792

  2726 Bright Bird Ln, Winter Park, FL 32792
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  /5

  $995,000

  • Land
  • 0.45 Acre
  • $2,211,111 per Acre

  2260 Hawick Ln, Winter Park, FL 32792

  This Winter Park investment opportunity is prime for Developers, Builders, & Investors for redevelopment. The Hawick Lane property is currently vacant as the home and trees were recently demo'ed. The future development of three (3) fee simple single family lots (50’ wide) is the highest and best use of this land. The lot split process is complete with individual surveys for each 50' wide lot. The

  Michael Rasmussen DAVEN REAL ESTATE INC

  2260 Hawick Ln, Winter Park, FL 32792
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  /18

  $2,395 per month

  • 3 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • House for Rent

  1148 Park Green Place, Winter Park, FL 32789

  Single family home in Winter Park! Close to shopping, theater, malls! Single family three bedroom two bath home Fully tiled interior, all appliances including washer and dryer. Fenced courtyard and patio. Two car garage with remote! Home is currently occupied. Call ahead for showing appointments

  Linda Baez DON ASHER & ASSOCIATES, INC.

  1148 Park Green Place, Winter Park, FL 32789
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  $1,095,000 Sold Dec 01, 2025

  1450 Chestnut Ave, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 1,942 Sq Ft
  • Built 2009

  Last Sold Summary

  • 16% Below List Price
  • $564/SF
  • 49 Days On Market

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  1450 Chestnut Ave, Winter Park, FL 32789
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  /25

  Est $2,016,711 Not Listed For Sale

  1925 Killarney Dr, Winter Park, FL 32789

  1925 Killarney Dr, Winter Park, FL 32789
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  /58

  $2,900,000

  • 3 Beds
  • 7 Baths
  • 5,483 Sq Ft

  1401 Green Cove Rd, Winter Park, FL 32789

  Set across Lake Maitland on a street where every home is an architectural gem, this Award-winning Villa Toscana blends Old-World craftsmanship with timeless architectural elegance in one of Winter Park’s most coveted enclaves. Built in 2009 and named “Best of Show” in the Parade of Homes, this 5,483 sq ft estate offers 3 bedrooms, 7 bathrooms, and 7 versatile bonus rooms, including a private

  Adriana Oyarce ANCHOR REAL ESTATE

  1401 Green Cove Rd, Winter Park, FL 32789
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  /19

  $4,695 per month

  • 3 Beds
  • 5 Baths
  • 2,659 Sq Ft
  • House for Rent

  1166 Palmer Ave, Winter Park, FL 32789

  1166 Palmer Ave Winter Park, Fl 32789 - Available December 1st - March 31st! Welcome home to this absolutely stunning property boasting an exceptionally open floor plan with loads of character! Located in the heart of Winter Park minutes from Downtown you will not find this opportunity arise often. This must see spacious home features 3 bedrooms, 3 full bathrooms, and 2 half bathrooms. Gorgeous

  Brock Stocksett HOMEVEST REALTY

  1166 Palmer Ave, Winter Park, FL 32789
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  $260,000 Sold Feb 27, 2025

  5132 Lazy Oaks Dr Unit 5132, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1982

  Last Sold Summary

  • 5% Below List Price
  • $258/SF
  • 1 Day On Market

  Current Estimated Value $259,121

  Last Listing Agent Natalia Moege PARK 26 REALTY LLC

  5132 Lazy Oaks Dr Unit 5132, Winter Park, FL 32792
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  /25

  Est $400,909 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  7494 Aloma Pines Ct, Winter Park, FL 32792

  7494 Aloma Pines Ct, Winter Park, FL 32792

Showing Results 481 - 520, Page 13 of 18