Winter Park, FL Homes

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  /11

  Not Listed For Sale

  0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792

  0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792

  Last Sold Summary

  • 8 Days On Market

  • Last Sold Price $417,500
  • Nov 29, 2023

  Last Listing Agent John Muccigrosso RE/MAX
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  /57

  $1,870,000

  • 5 Beds
  • 4.5 Baths
  • 4,363 Sq Ft

  1177 Kenwood Ave, Winter Park, FL 32789

  Welcome to 1177 Kenwood Ave, a home that blends warmth, comfort, and thoughtful design. The inviting living room features a cozy fireplace, creating the perfect space to relax on cooler evenings. The kitchen is designed with both style and function in mind, stainless steel appliances and a center island ideal for meal preparation and gathering. The spacious primary suite serves as a retreat,

  Karen Albright OPENDOOR BROKERAGE LLC

  1177 Kenwood Ave, Winter Park, FL 32789
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  /2

  $627,000 Sold Mar 23, 2026

  428 Selkirk Dr, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 1,782 Sq Ft
  • Built 1957

  Last Sold Summary

  • 5% Below List Price
  • $352/SF
  • 103 Days On Market

  Current Estimated Value $624,915

  Last Listing Agent Sheri Malin REDFIN CORPORATION

  428 Selkirk Dr, Winter Park, FL 32792
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  /11

  Est $454,003 Not Listed For Sale

  2737 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2023

  2737 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 5% Below List Price
  • $268/SF
  • 110 Days On Market

  • Last Sold Price $477,790
  • Feb 16, 2024

  Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES
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  $2,394,500 New Construction

  • 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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  /2

  $625,000 Sold Mar 27, 2026

  1500 Berkshire Ave, Winter Park, FL 32789

  • 3 Beds
  • 1.5 Baths
  • 1,485 Sq Ft
  • Built 1925

  Last Sold Summary

  • $421/SF
  • 51 Days On Market

  Current Estimated Value $614,957

  Last Listing Agent Lianna D'Angelo SOTERA LIVING

  1500 Berkshire Ave, Winter Park, FL 32789
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  /2

  Est $6,222,655 Not Listed For Sale

  654 W Morse Blvd, Winter Park, FL 32789

  • 5 Beds
  • 7.5 Baths
  • 8,752 Sq Ft
  • Built 2022

  654 W Morse Blvd, Winter Park, FL 32789

  Last Sold Summary

  • 3% Above List Price
  • $691/SF
  • 120 Days On Market

  • Last Sold Price $6,050,000
  • Feb 10, 2025

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC
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  /23

  $339,000

  • 3 Beds
  • 2 Baths
  • 1,160 Sq Ft

  1760 Peruvian Ln, Winter Park, FL 32792

  Winter Park “Sweet Spot”, Priced to Sell: Rare 3/2 Opportunity in Eastbrook Discover the perfect blend of value, location, and versatility in Winter Park’s highly sought-after Eastbrook neighborhood. This 3-bedroom, 2-bathroom home is ideal for homebuyers looking to make new memories or savvy investors seeking a turn-key property. Move-in Ready: From the moment you step inside this roomy, open

  Moe Mossa SAVVY AVENUE, LLC

  1760 Peruvian Ln, Winter Park, FL 32792
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  /2

  $1,430,000 Sold Nov 10, 2025

  1011 Mckean Cir, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,230 Sq Ft
  • Built 1955

  Last Sold Summary

  • $641/SF
  • 0 Days On Market

  Current Estimated Value $1,449,623

  Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

  1011 Mckean Cir, Winter Park, FL 32789
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  /21

  Est $440,832 Not Listed For Sale

  2861 Clever Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2023

  2861 Clever Ln, Winter Park, FL 32792

  Last Sold Summary

  • 4% Above List Price
  • $221/SF
  • 1 Day On Market

  • Last Sold Price $421,990
  • Oct 23, 2023

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  /21

  $129,900

  • 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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  /2

  $439,900 Sold Jul 22, 2025

  1945 Bering Ave, Winter Park, FL 32789

  • 3 Beds
  • 1.5 Baths
  • 1,576 Sq Ft
  • Built 1958

  Last Sold Summary

  • $279/SF
  • 6 Days On Market

  Current Estimated Value $439,314

  Last Listing Agent Carmen Gonzalez, Pa HORIZON WEST REALTY

  1945 Bering Ave, Winter Park, FL 32789
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  /23

  Est $296,432 Not Listed For Sale

  3197 Crown Jewel Ct, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft
  • Built 2019

  3197 Crown Jewel Ct, Winter Park, FL 32792

  Last Sold Summary

  • 13% Below List Price
  • $241/SF
  • 23 Days On Market

  • Last Sold Price $340,000
  • Oct 20, 2023

  Last Listing Agent Priscilla Chan FLORIDA REALTY INVESTMENTS
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  /31

  $599,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,556 Sq Ft

  1951 Staunton Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. TRANSFERABLE TERMITE BOND INCLUDED. Welcome home to the charm and character of the bygone days. This 3-bedroom, 2-bathroom home offers 2,556 square feet, with the historic main home originally built in 1922. Featuring original antique wood floors, a classic fireplace, and a one of a kind upstairs loft, there's nothing quite like it! A charming front porch

  Veronica Figueroa EXP REALTY LLC

  1951 Staunton Ave, Winter Park, FL 32789
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  /2

  $570,000 Sold May 04, 2026

  1537 Bantam Way, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft
  • Built 2022

  Last Sold Summary

  • 20% Above List Price
  • $247/SF
  • 3 Days On Market

  Current Estimated Value $471,365

  Last Listing Agent Jared Dunn LIVE MVRK LLC

  1537 Bantam Way, Winter Park, FL 32792
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  Est $588,558 Not Listed For Sale

  1178 Wildmeadow Run, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft
  • Built 2021

  1178 Wildmeadow Run, Winter Park, FL 32792

  Last Sold Summary

  • 2% Below List Price
  • $340/SF
  • 6 Days On Market

  • Last Sold Price $601,000
  • Oct 27, 2023

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES
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  /64

  $444,900

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

  1951 Canny Cove, Winter Park, FL 32792

  Welcome to easy, light-filled living in this beautifully maintained 3-bedroom, 2.5-bath corner townhome in the gated Grayson Square community. Freshly painted and designed for comfort, the open living and dining spaces feel bright and inviting, flowing effortlessly to a covered lanai—perfect for relaxing evenings or casual gatherings. The kitchen offers a clean, modern look with stainless steel

  Denise Del Castillo LPT REALTY, LLC

  1951 Canny Cove, Winter Park, FL 32792
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  /2

  $385,000 Sold Feb 09, 2026

  5563 Garden Grove Cir, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,436 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Below List Price
  • $268/SF
  • 36 Days On Market

  Current Estimated Value $391,042

  Last Listing Agent Anne Jones COLDWELL BANKER HUBBARD HANSEN

  5563 Garden Grove Cir, Winter Park, FL 32792
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  /18

  Not Listed For Sale

  1411 Miller Ave, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 1,813 Sq Ft
  • Built 2023

  1411 Miller Ave, Winter Park, FL 32789

  Last Sold Summary

  • $430/SF
  • 30 Days On Market

  • Last Sold Price $779,900
  • Nov 14, 2023

  Last Listing Agent Kimberly Griffin RE/MAX
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  /17

  $6,950,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,905 Sq Ft

  40 Palmer Ave, Winter Park, FL 32789

  Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  40 Palmer Ave, Winter Park, FL 32789
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  /2

  $2,575,000 Sold Oct 20, 2025

  1341 Place Picardy, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,469 Sq Ft
  • Built 2016

  Last Sold Summary

  • 8% Below List Price
  • $576/SF
  • 95 Days On Market

  Current Estimated Value $2,546,833

  Last Listing Agent Julie Bettosini STOCKWORTH REALTY GROUP

  1341 Place Picardy, Winter Park, FL 32789
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  /2

  Est $95,313 Not Listed For Sale

  3035 George Mason Ave Unit 18, Winter Park, FL 32792

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

  3035 George Mason Ave Unit 18, Winter Park, FL 32792

  Last Sold Summary

  • 18% Below List Price
  • $211/SF
  • 196 Days On Market

  • Last Sold Price $116,000
  • Sep 10, 2024

  Last Listing Agent Margarita Morales OLYMPUS EXECUTIVE REALTY INC
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  /53

  $2,184,000 Pending

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

  2503 Versailles Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Back on the market—an exceptional opportunity in Winter Park. Now offered below appraised value, this residence has been thoughtfully refreshed with new carpet, interior paint, and thoughtful enhancements.Presented for the first time, this beautifully appointed 2014 David Weekley home is tucked away on a large corner lot within a rare cul-de-sac in the

  Sarah Tomlinson COMPASS FLORIDA LLC

  2503 Versailles Ave, Winter Park, FL 32789
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  /2

  $435,000 Sold Aug 31, 2025

  2209 Fairglenn Way, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,027 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Below List Price
  • $215/SF
  • 54 Days On Market

  Current Estimated Value $448,669

  Last Listing Agent Benjamin Benami CHARLES RUTENBERG REALTY ORLANDO

  2209 Fairglenn Way, Winter Park, FL 32792
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  /18

  Est $447,697 Not Listed For Sale

  1916 Erudite Way, Winter Park, FL 32792

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

  1916 Erudite Way, Winter Park, FL 32792

  Last Sold Summary

  • 4% Below List Price
  • $262/SF
  • 146 Days On Market

  • Last Sold Price $466,790
  • Mar 11, 2024

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  /41

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,263 Sq Ft

  5331 Oak Ct, Winter Park, FL 32792

  Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to

  Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

  5331 Oak Ct, Winter Park, FL 32792
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  /2

  $714,000 Sold Feb 25, 2026

  1449 Pelican Bay Trail, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,928 Sq Ft
  • Built 1982

  Last Sold Summary

  • $244/SF
  • 2 Days On Market

  Current Estimated Value $713,552

  Last Listing Agent Steven Ritz KELLER WILLIAMS WINTER PARK

  1449 Pelican Bay Trail, Winter Park, FL 32792
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  /2

  Est $537,990 Not Listed For Sale

  1051 Aragon Ave Unit 1051, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,669 Sq Ft
  • Built 1987

  1051 Aragon Ave Unit 1051, Winter Park, FL 32789

  Last Sold Summary

  • 6% Below List Price
  • $342/SF
  • 104 Days On Market

  • Last Sold Price $570,000
  • Sep 16, 2024

  Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES
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  /27

  $169,500

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft

  3282 Oak Lake Place, Winter Park, FL 32792

  Welcome to Hidden Oaks! This beautifully updated 2-story condo offers the perfect blend of style and affordability. Featuring a fresh kitchen, renovated bathroom, and new flooring throughout, this move-in-ready home includes an in-unit washer/dryer for ultimate convenience. As a desirable end unit, you’ll enjoy extra privacy and a peaceful view of the adjacent conservation area. Relax on your

  Chad Busby BUSBY REALTY LLC

  3282 Oak Lake Place, Winter Park, FL 32792
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  /2

  $242,000 Sold Oct 15, 2025

  200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792

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

  Last Sold Summary

  • 9% Below List Price
  • $199/SF
  • 125 Days On Market

  Current Estimated Value $234,932

  Last Listing Agent Jessica Geer A+ REALTY PROFESSIONALS, INC

  200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792
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  /2

  Est $369,461 Not Listed For Sale

  7632 Aloma Pines Ct, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft
  • Built 2018

  7632 Aloma Pines Ct, Winter Park, FL 32792

  Last Sold Summary

  • $198/SF
  • 129 Days On Market

  • Last Sold Price $370,000
  • Jan 30, 2025

  Last Listing Agent Dayanne Rivera PREFERRED REAL ESTATE BROKERS
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  /43

  $169,000 Pending

  • 1 Bed
  • 1 Bath
  • 793 Sq Ft

  200 Saint Andrews Blvd Unit 315, Winter Park, FL 32792

  **One or more photos were virtually stages**Experience elevated living in this beautifully appointed 1-bedroom, 1-bath residence located on the second floor in the heart of Winter Park, Florida. The home showcases elegant wood-look tile flooring throughout, creating a seamless, upscale aesthetic with both style and durability.The primary bedroom is enhanced with classic plantation shutters,

  Eric Zimmerman RE/MAX Advantage

  200 Saint Andrews Blvd Unit 315, Winter Park, FL 32792
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  /2

  $535,000 Sold May 28, 2025

  4200 Bear Gully Rd, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 1,945 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $275/SF
  • 35 Days On Market

  Current Estimated Value $538,464

  Last Listing Agent Renee Killiri RED BIRD REALTY OF FLORIDA INC

  4200 Bear Gully Rd, Winter Park, FL 32792
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  /32

  Est $457,540 Not Listed For Sale

  2445 Firstlight Way, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft
  • Built 2018

  2445 Firstlight Way, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $229/SF
  • 41 Days On Market

  • Last Sold Price $460,000
  • Oct 17, 2023

  Last Listing Agent Karen Wheeler RE/MAX CENTRAL REALTY
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  /27

  $470,000

  • 4 Beds
  • 2 Baths
  • 1,787 Sq Ft

  1032 Manchester Cir, Winter Park, FL 32792

  Welcome to this beautifully maintained 4-bedroom, 2-bath pool home nestled in one of the nice neighborhoods in Winter Park, located within Seminole County. Offering the perfect blend of comfort, space, and Florida living, this home is designed for both everyday enjoyment and effortless entertaining.Step inside to discover a spacious, light-filled floor plan featuring generous living areas,

  Nancy Morales BHHS FLORIDA REALTY

  1032 Manchester Cir, Winter Park, FL 32792
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  /2

  $528,000 Sold Nov 25, 2025

  4991 Tangerine Ave, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,124 Sq Ft
  • Built 1972

  Last Sold Summary

  • $249/SF
  • 5 Days On Market

  Current Estimated Value $518,614

  Last Listing Agent Edwin Ayala, Jr EXP REALTY LLC

  4991 Tangerine Ave, Winter Park, FL 32792
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  Est $1,972,239 Not Listed For Sale

  2156 Talman Ct, Winter Park, FL 32792

  • 5 Beds
  • 8 Baths
  • 7,762 Sq Ft
  • Built 2008

  2156 Talman Ct, Winter Park, FL 32792

  Last Sold Summary

  • 4% Below List Price
  • $264/SF
  • 32 Days On Market

  • Last Sold Price $2,050,000
  • Oct 26, 2023

  Last Listing Agent Abby Nguyen AGENCYONE
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  /9

  $349,000

  • 2 Beds
  • 1 Bath
  • 749 Sq Ft

  811 Overspin Dr, Winter Park, FL 32789

  Charming Winter Park Opportunity in Desirable Dubsdread Heights! NEW ROOF NEW A/c new kitchen ,bath, floor Welcome to 811 Overspin Drive, a cozy and character-filled 2-bedroom, 1-bath single-family home nestled in the heart of Winter Park. This property offers approximately 700+ square feet of living space on a generously sized lot, providing endless potential for homeowners, investors, or those

  Rickey Singh RICK SINGH REAL ESTATE

  811 Overspin Dr, Winter Park, FL 32789
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  /2

  $415,000 Sold Mar 02, 2026

  875 W Lyman Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 760 Sq Ft
  • Built 1925

  Last Sold Summary

  • 13% Below List Price
  • $546/SF
  • 60 Days On Market

  Current Estimated Value $417,125

  Last Listing Agent Joey Bruno CHARLES RUTENBERG REALTY ORLANDO

  875 W Lyman Ave, Winter Park, FL 32789
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  /20

  Est $467,151 Not Listed For Sale

  2448 Firstlight Way, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft
  • Built 2020

  2448 Firstlight Way, Winter Park, FL 32792

  Last Sold Summary

  • 5% Above List Price
  • $214/SF
  • 89 Days On Market

  • Last Sold Price $445,000
  • Oct 30, 2023

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

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