Winter Park, FL Homes

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  /61

  $2,394,500

  New Construction Pending

  • 5 Beds
  • 6.5 Baths
  • 4,506 Sq Ft

  2412 Chantilly Ave, Winter Park, FL 32789

  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 both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This

  Tab Bish LLC REAL BROKER, LLC

  2412 Chantilly Ave, Winter Park, FL 32789
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  /18

  $3,400 Per Month

  • 3 Beds
  • 2 Baths
  • 1,810 Sq Ft
  • House for Rent

  904 Carvell Dr, Winter Park, FL 32792

  Welcome to Winter Park Estates, a quiet community conveniently located just minutes from Downtown Winter Park, 408, Downtown Orlando, Full Sail University, and more. This beautifully remodeled pool home, set on a spacious 0.26-acre lot, offers 3 bedrooms, 2 bathrooms, and an updated kitchen with a view of the sparkling pool. The open floor plan includes large living and dining areas, perfect for

  904 Carvell Dr, Winter Park, FL 32792
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  /2

  $397,500

  Sold Aug 28, 2026

  3463 Arnel Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft
  • Built 1967

  Last Sold Summary

  • 17% Below List Price
  • $225/SF
  • 133 Days On Market

  Current Estimated Value $405,977

  Last Listing Agent Alexa Monasterio Flores KELLER WILLIAMS ADVANTAGE 2 REALTY

  3463 Arnel Dr, Winter Park, FL 32792
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  /2

  Est $183,871

  Not Listed For Sale

  200 Saint Andrews Blvd Unit 2703, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,127 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 2703, Winter Park, FL 32792

  Last Sold Summary

  • 276 Days On Market

  Last Listing Agent Jodie Lutz COLDWELL BANKER REALTY
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  /27

  $660,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,243 Sq Ft

  1416 Border Dr, Winter Park, FL 32789

  An opportunity to build new in an established Winter Park neighborhood. The existing home remains on the property and is offered for its land value only, allowing a buyer to design from the ground up on a street where redevelopment is already underway. Within a half mile, seven custom single-family homes are in their final phase of construction, most starting near $1.5 million. Border Drive

  Audra Wilks PREMIER SOTHEBY'S INTL. REALTY

  1416 Border Dr, Winter Park, FL 32789
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  /19

  $1,450 Per Month

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Condo for Rent

  3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792

  Beautiful 2-bedroom, 2-bath condo available for rent in the highly desirable Winter Park area. This inviting home is thoughtfully designed for comfortable family living and features no carpet, with durable laminate flooring throughout perfect for easy cleaning and everyday use. The condo offers a spacious and functional layout, including a bright living area ideal for family time and

  Praveen Setty RIGHTHOUSE REALTY LLC

  3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792
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  /2

  $130,000

  Sold Nov 25, 2025

  200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 727 Sq Ft
  • Built 1970

  Last Sold Summary

  • 13% Below List Price
  • $179/SF
  • 35 Days On Market

  Current Estimated Value $136,130

  Last Listing Agent Mary Marwick PREMIUM PROPERTIES R.E SERVICE

  200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792
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  /2

  Est $384,867

  Not Listed For Sale

  620 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,214 Sq Ft
  • Built 1986

  620 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  Last Sold Summary

  • 188 Days On Market

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES
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  /38

  $810,000

  $69K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,030 Sq Ft

  1265 Arlington Place, Winter Park, FL 32789

  Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollins College, Park Avenue, and all the dining, shopping, and culture that downtown Winter Park provides. The main level features an open living area flowing into a well-equipped kitchen with granite countertops and solid wood

  Erika Beerbower FANNIE HILLMAN & ASSOCIATES

  1265 Arlington Place, Winter Park, FL 32789
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  /16

  $1,550 Per Month

  • 2 Beds
  • 2 Baths
  • 964 Sq Ft
  • Condo for Rent

  3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792

  This charming 2-bedroom, 2-bath duplex is ready for immediate move-in, offering a warm and inviting atmosphere for comfortable living.Step inside to discover a thoughtfully designed space with tile flooring throughout, providing both durability and easy maintenance. The heart of the home is the well-appointed kitchen, featuring stainless steel appliances and solid-surface countertops.

  3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792
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  /2

  $975,000

  Sold Feb 10, 2026

  1150 Kenwood Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,557 Sq Ft
  • Built 1988

  Last Sold Summary

  • 24% Below List Price
  • $381/SF
  • 97 Days On Market

  Current Estimated Value $1,043,116

  Last Listing Agent JJ Mackle PREMIER SOTHEBY'S INTL. REALTY

  1150 Kenwood Ave, Winter Park, FL 32789
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  /2

  Est $550,254

  Not Listed For Sale

  875 Miles Ave Unit 4, Winter Park, FL 32789

  • 18 Beds
  • 18 Baths
  • 1,852 Sq Ft
  • Built 2005

  875 Miles Ave Unit 4, Winter Park, FL 32789

  Last Sold Summary

  • 123 Days On Market

  Last Listing Agent Moshe Sheffi HPL REALTY INVESTMENTS
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  /4

  $1,750,000

  • Land
  • 16,117 Sq Ft
  • $4,729,730 per Acre

  313L Sylvan Dr, Winter Park, FL 32789

  Exceptional opportunity to build on beautiful Lake Sylvan with this 0.37-acre (approximately 16,603-square-foot) lakefront homesite. Offering a picturesque waterfront setting, the property is ideally positioned just minutes from Park Avenue's shops and restaurants, major roadways, leading hospitals and top private schools. Create a custom lakefront residence tailored to your vision in one of

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  313L Sylvan Dr, Winter Park, FL 32789
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  /18

  $2,200 Per Month

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Condo for Rent

  Unlisted Address

  Townhouse in Winter Park! Totally Renovated 3 bed 2 bath townhouse. Large Living room. Dinette off of kitchen. Updated kitchen with stainless steel appliances. Wash and dryer hook ups inside closet. Big master suite. Good size covered porch in back. Enjoy the 2 community pools, playground, tennis and shuffleboard courts! Good schools. Zoned for Lake Howell High School. Must see!

  Kirsten Cantello TRUSTHOME PROPERTIES INC

  Unlisted Address
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  /2

  $415,000

  Sold Mar 04, 2026

  1816 Ivy Ln, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,725 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $241/SF
  • 139 Days On Market

  Current Estimated Value $401,860

  Last Listing Agent Michael Cameron CAMERON REALTY GROUP LLC

  1816 Ivy Ln, Winter Park, FL 32792
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  /2

  Est $438,297

  Not Listed For Sale

  2931 Clever Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2024

  2931 Clever Ln, Winter Park, FL 32792

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
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  /42

  $399,800

  $30K PRICE DROP Under Contract

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  1610 Gladiolas Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. PRICE IMPROVEMENT! This 4-bedroom, 2-bath pool home in the heart of Winter Park is priced to sell and offers an incredible opportunity to make it your own. While the property could use some TLC, it features solid major updates and endless potential to add value.Situated on an oversized lot with NO HOA, this home features a spacious enclosed lanai,

  Jasmin Cabral LIFESTYLE INTERNATIONAL REALTY

  1610 Gladiolas Dr, Winter Park, FL 32792
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  /26

  $2,800 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,378 Sq Ft
  • Townhouse for Rent

  2452 Firstlight Way, Winter Park, FL 32792

  Let me present this Like new townhome in a gated new community in Winter Park.This immaculate 3 bed 2.5 bath townhome is ready to move-in. Massive 23x14 Master bedroom. Open concept family room opens to the kitchen / nook area. The downstairs dining area could be used as an office / den or add a closet for a 4th bedroom. A large loft is great for a computer area / play area. The Master

  2452 Firstlight Way, Winter Park, FL 32792
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  /2

  $475,000

  Sold May 14, 2026

  665 W Lyman Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Built 1994

  Last Sold Summary

  • 6% Above List Price
  • $424/SF
  • 6 Days On Market

  Current Estimated Value $467,792

  Last Listing Agent Jonathan Nakhnoukh CENTRAL FLORIDA PRIME REAL ESTATE LLC

  665 W Lyman Ave, Winter Park, FL 32789
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  /2

  Est $450,254

  Not Listed For Sale

  2939 Clever Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2024

  2939 Clever Ln, Winter Park, FL 32792

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
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  /11

  $4,299,000

  • Land
  • 8.23 Acres
  • $522,357 per Acre

  2403 Euston Rd, Winter Park, FL 32789

  Fly In. Unwind. Build Your Dream on Lake Killarney. Bring your seaplane and envision the lakefront estate of your dreams on one of Winter Park’srarest offerings. Tucked away on a private peninsula surrounded by multi-million-dollar homes, this extraordinary property spans approximately432 feet of shoreline along the spring-fed, crystal-clear waters of Lake Killarney. With 1.514 buildable

  Marie Ledbetter COLDWELL BANKER REALTY

  2403 Euston Rd, Winter Park, FL 32789
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  /40

  $3,450 Per Month

  • 4 Beds
  • 2 Baths
  • 1,660 Sq Ft
  • House for Rent

  333 Cornwall Rd, Winter Park, FL 32792

  Located in the heart of Winter Park, Winter Park Pines is a well-established neighborhood known for its convenience, school zoning, and access to outdoor living. A place to slow down, where evening walks feel like something out of a storybook, and the Cady Way Trail is just steps from your back door for morning runs, bike rides, and everything in between. One of the standout features is having

  Melissa Johnson EXP REALTY LLC

  333 Cornwall Rd, Winter Park, FL 32792
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  /2

  $168,146

  Sold Jun 01, 2026

  1000 S Semoran Blvd Unit 805, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,003 Sq Ft
  • Built 1969

  Last Sold Summary

  • 6% Below List Price
  • $168/SF
  • 46 Days On Market

  Current Estimated Value $168,872

  Last Listing Agent Carrie Shawfield SHAWFIELD REALTY GROUP

  1000 S Semoran Blvd Unit 805, Winter Park, FL 32792
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  /2

  Not Listed For Sale

  3065 George Mason Ave Unit B, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 525 Sq Ft
  • Built 1974

  3065 George Mason Ave Unit B, Winter Park, FL 32792

  Last Sold Summary

  • 168 Days On Market

  Last Listing Agent Jacki Sandler SANDLER MANAGEMENT INC
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  /45

  $965,000

  Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,957 Sq Ft

  1256 S Pennsylvania Ave Unit 9, Winter Park, FL 32789

  Positioned in Winter Park’s Virginia Heights neighborhood, just moments from Park Avenue and Seven Oaks Park, this Mediterranean-inspired townhome-style condominium offers three bedrooms, two and a half baths and nearly 2,000 square feet of conditioned living space. A rare private driveway, gated entry and paver walkway establish a distinct sense of arrival, while wrought-iron details introduce

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  1256 S Pennsylvania Ave Unit 9, Winter Park, FL 32789
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  /16

  $1,700 Per Month

  • 2 Beds
  • 2 Baths
  • 1,059 Sq Ft
  • Excellent location

  4968 Tangerine Ave Unit 4968, Winter Park, FL 32792

  This roomy condo is available for immediate occupancy. New Luxury Vinyl Plank floors just installed. The unit is ideally located in Winter Park, not far from Full Sail or UCF. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet community with plenty of privacy. Amenities include a pool and workout room. Call today for your private tour of this amazing

  4968 Tangerine Ave Unit 4968, Winter Park, FL 32792
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  /2

  $170,000

  Sold Sep 24, 2025

  200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Built 1970

  Last Sold Summary

  • 10% Below List Price
  • $152/SF
  • 74 Days On Market

  Current Estimated Value $181,746

  Last Listing Agent Evelyn Pilchick RE/MAX 200 REALTY

  200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792
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  /2

  Est $203,882

  Not Listed For Sale

  608 Montego Bay Ct Unit S, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1981

  608 Montego Bay Ct Unit S, Winter Park, FL 32792

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK
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  /59

  $455,000

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,903 Sq Ft

  8433 Commander Cove, Winter Park, FL 32792

  NEW ROOF TO BE INSTALLED OCTOBER 2026 + NEW WATER HEATER!Welcome to 8433 Commander Cove, a spacious 4-bedroom, 2.5-bath home located on a quiet cul-de-sac in the desirable Trinity Bay community.Vaulted ceilings, abundant natural light and a stunning cathedral-style front window create a bright, inviting feel. The family room features a grand brick fireplace, while the flexible

  Brandi Cepeda CEPEDA REAL ESTATE LLC

  8433 Commander Cove, Winter Park, FL 32792
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  /21

  $2,295 Per Month

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft
  • Condo for Rent

  700 Melrose Ave Unit A5, Winter Park, FL 32789

  Beautifully upgraded 2-bedroom, 2-bath condo in the heart of Winter Park! Located in a sought-after 55+ community surrounded by mature, lush landscaping, this charming condo offers the perfect blend of comfort and convenience. Enjoy a short walk to Mead Botanical Garden or the shops, dining, and entertainment along Park Avenue. With easy access to I-4, downtown Orlando, hospitals, shopping, and

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit A5, Winter Park, FL 32789
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  /2

  $475,000

  Sold Feb 02, 2026

  1740 Anzle Ave, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft
  • Built 1956

  Last Sold Summary

  • 40% Below List Price
  • $263/SF
  • 109 Days On Market

  Current Estimated Value $551,610

  Last Listing Agent Freddy DeCoster GOYAL & DECOSTER REALTY

  1740 Anzle Ave, Winter Park, FL 32789
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  /89

  Est $1,306,610

  Not Listed For Sale

  3629 Midiron Dr, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft
  • Built 2024

  3629 Midiron Dr, Winter Park, FL 32789

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Amanda Wood RE/MAX EXCLUSIVE COLLECTION
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  /100

  $765,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 2,137 Sq Ft

  1246 Verdant Glade Place, Winter Park, FL 32792

  Welcome to 1246 Verdant Glade Place in The Meadows at Hawk’s Crest, where luxury, thoughtful design, andresort-style living come together! This beautifully maintained original-owner 4-bedroom, 3.5-bath homeshowcases exceptional upgrades, including LVP flooring on both levels, plantation shutters, 8-foot first-floordoors, 5.25-inch baseboards, upgraded cabinetry, custom woodwork, and

  Greg Lowe FLORIDA REALTY RESULTS LLC

  1246 Verdant Glade Place, Winter Park, FL 32792
• 

  

  /23

  $2,599 Per Month

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft
  • House for Rent

  3465 Balsam Dr, Winter Park, FL 32792

  Welcome to this charming 3-bedroom, 2-bathroom home in a well-established Winter Park neighborhood. This single-story property offers a comfortable layout with inviting living spaces, a bright living area, an eat-in kitchen, and well-sized bedrooms, including a primary suite with a private bath. Features include a whole-home water softener, premium appliances, spa-like showers, wood and tile

  3465 Balsam Dr, Winter Park, FL 32792
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  /2

  $2,750,000

  Sold Jun 18, 2026

  151 Oakwood Way, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,129 Sq Ft
  • Built 2023

  Last Sold Summary

  • 14% Below List Price
  • $666/SF
  • 113 Days On Market

  Current Estimated Value $2,780,288

  Last Listing Agent Matthew Burks CORCORAN PREMIER REALTY

  151 Oakwood Way, Winter Park, FL 32789
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  /38

  Est $784,405

  Not Listed For Sale

  1477 Lone Feather Trail, Winter Park, FL 32792

  • 5 Beds
  • 3.5 Baths
  • 2,894 Sq Ft
  • Built 2021

  1477 Lone Feather Trail, Winter Park, FL 32792

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Christopher Soucy REALTY ONE GROUP MVP
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  /13

  $1,275,000

  • 3 Beds
  • 2.5 Baths
  • 1,329 Sq Ft

  240 Killarney Dr, Winter Park, FL 32789

  Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just

  Shandy Ortiz PREMIER SOTHEBYS INT'L REALTY

  240 Killarney Dr, Winter Park, FL 32789
• 

  

  /19

  $1,750 Per Month

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Apartment for Rent

  652 Saint Johns Ct Unit 652, Winter Park, FL 32792

  Prime Winter Park rental opportunity! Conveniently located near top universities, shopping centers, restaurants, and major highways, this well-kept apartment delivers exceptional comfort and accessibility. Community amenities include a swimming pool and landscaped common areas. Pets considered on a case-by-case basis with size approval. Prompt scheduling is recommended, reach out today to set up

  Marina Gamundi KELLER WILLIAMS ADVANTAGE III

  652 Saint Johns Ct Unit 652, Winter Park, FL 32792
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  /2

  $1,725,000

  Sold Mar 05, 2026

  617 Worthington Dr, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,533 Sq Ft
  • Built 2018

  Last Sold Summary

  • 13% Below List Price
  • $488/SF
  • 215 Days On Market

  Current Estimated Value $1,751,487

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  617 Worthington Dr, Winter Park, FL 32789
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  /2

  Est $210,397

  Not Listed For Sale

  200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792

  Last Sold Summary

  • 108 Days On Market

  Last Listing Agent Larry Ouellette MANA REAL ESTATE

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