Winter Park, FL Homes

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  /26

  $500,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,745 Sq Ft

  2126 N Hampton Cir, Winter Park, FL 32792

  Under contract-accepting backup offers. Step into your own private retreat in the sought-after Winter Woods community! This beautifully maintained 3-bedroom, 2-bath pool home offers 1,745 square feet of inviting living space designed for both comfort and effortless entertaining. From the moment you arrive, you’ll be greeted by lush, mature landscaping that creates a sense of privacy and charm.

  Joseph Sipp KELLER WILLIAMS WINTER PARK

  2126 N Hampton Cir, Winter Park, FL 32792
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  /23

  $1,500 per month

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

  1695 Lee Rd Unit B114, Winter Park, FL 32789

  The unit has two spacious bedrooms, galley kitchen, walk in closet, living/dining room combo, washer and dryer combo brand new refrigerator , and lovely patio that leads to the community pool and playground. .This well-maintained unit features a spacious living area filled with natural light Cove is located centrally to major highways, schools, tons of shopping & restaurants so it is a great

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit B114, Winter Park, FL 32789
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  /2

  $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 $378,517

  Last Listing Agent Dora Siler FOLIO REALTY LLC

  350 Killarney Bay Ct Unit 5, Winter Park, FL 32789
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  /29

  Not Listed For Sale

  7482 Canford Ct Unit 7482, Winter Park, FL 32792

  • 2 Beds
  • 1.5 Baths
  • 1,393 Sq Ft
  • Built 1974

  7482 Canford Ct Unit 7482, Winter Park, FL 32792

  Last Sold Summary

  • $179/SF
  • 9 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Dee Concepcion ALL REAL ESTATE & INVESTMENTS
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  /69

  $1,675,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,263 Sq Ft

  446 Alberta Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only a mile stroll to the famous Park Ave shops, dining and entertaining. Home site over looks Lake Osceola and the multi million dollar homes all around!! A neighborhood lot, a few doors down, allows

  Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  446 Alberta Dr, Winter Park, FL 32789
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  /17

  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit E115, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit E115, Winter Park, FL 32789
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  /2

  $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

  Current Estimated Value $1,080,985

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  1450 Chestnut Ave, Winter Park, FL 32789
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  /11

  Est $436,953 Not Listed For Sale

  2711 Bright Bird Ln, Winter Park, FL 32792

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

  2711 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 1% Above List Price
  • $244/SF

  Last Sold Price $434,619

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  /55

  $495,000

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

  630 Killarney Bay Ct Unit 3, Winter Park, FL 32789

  Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath, with a convenient half

  Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

  630 Killarney Bay Ct Unit 3, Winter Park, FL 32789
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  /2

  $220,000 Sold Jan 30, 2026

  700 Melrose Ave Unit J23, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 772 Sq Ft
  • Built 1964

  Last Sold Summary

  • 6% Below List Price
  • $285/SF
  • 107 Days On Market

  Current Estimated Value $214,548

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit J23, Winter Park, FL 32789
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  /27

  Est $155,090 Not Listed For Sale

  603 Saint Johns Ct Unit S, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 759 Sq Ft
  • Built 1981

  603 Saint Johns Ct Unit S, Winter Park, FL 32792

  Last Sold Summary

  • 16% Below List Price
  • $244/SF
  • 3 Days On Market

  Last Sold Price $185,000

  Last Listing Agent Melissa Johnson EXP REALTY LLC
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  /46

  $450,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,694 Sq Ft

  2152 Conifer Ave, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Price ENHANCEMENT! The best value in the area. Do not miss out on the opportunity to be the next owner of Conifer Avenue!This POOL home is amazing in every way and is truly a must see! Original Owner with incredible pride of ownership. Brand NEW Roof, Brand NEW Water Heater 2025, HVAC 2020, entire replumb

  Denise Korrey KORR REALTY CORP

  2152 Conifer Ave, Winter Park, FL 32792
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  /2

  $400,000 Sold Feb 13, 2026

  2833 Prince John Rd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,605 Sq Ft
  • Built 1963

  Last Sold Summary

  • 7% Below List Price
  • $249/SF
  • 9 Days On Market

  Current Estimated Value $452,077

  Last Listing Agent Makena Clark EXIT REALTY PREMIER LEGACY

  2833 Prince John Rd, Winter Park, FL 32792
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  /44

  Not Listed For Sale

  1250 Formosa Ave, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 1,937 Sq Ft
  • Built 2022

  1250 Formosa Ave, Winter Park, FL 32789

  Last Sold Summary

  • 3% Above List Price
  • $307/SF
  • 50 Days On Market

  Last Sold Price $595,000

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS
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  /99

  $5,495,000

  • 5 Beds
  • 6.5 Baths
  • 7,278 Sq Ft

  2211 Azalea Place, Winter Park, FL 32789

  Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Park’s most prestigious neighborhoods—just moments from the exclusive Winter Park Racquet Club. This extraordinary residence offers the perfect blend of timeless architecture, refined finishes, and state-of-the-art updates, all

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  2211 Azalea Place, Winter Park, FL 32789
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  /2

  $538,500 Sold May 16, 2025

  2855 Cady Way, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • Built 1964

  Last Sold Summary

  • 9% Below List Price
  • $310/SF
  • 76 Days On Market

  Current Estimated Value $536,032

  Last Listing Agent Joe Cremonese GLOBAL PROPERTIES SALES & MGMT

  2855 Cady Way, Winter Park, FL 32792
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  /44

  Est $868,596 Not Listed For Sale

  1403 Michigan Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,513 Sq Ft
  • Built 2024

  1403 Michigan Ave, Winter Park, FL 32789

  Last Sold Summary

  • 6% Below List Price
  • $369/SF
  • 65 Days On Market

  Last Sold Price $927,000

  Last Listing Agent Amanda Wood RE/MAX
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  /53

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft

  100 S Interlachen Ave Unit 101, Winter Park, FL 32789

  On the first floor within The Cloisters, this three-bedroom, two-bath residence offers 1,734 square feet of renovated living space in one of Winter Park’s accessible lakefront communities. An oversized tiled patio, partially covered and ideal for outdoor dining or morning coffee, extends the living space and enhances everyday functionality. Renovated in 2021 by Charles Clayton Construction, an

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 101, Winter Park, FL 32789
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  /2

  $284,000 Sold May 23, 2025

  2539 Antilles Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1976

  Last Sold Summary

  • 5% Below List Price
  • $249/SF
  • 50 Days On Market

  Current Estimated Value $278,476

  Last Listing Agent Allie George CORCORAN PREMIER REALTY

  2539 Antilles Dr, Winter Park, FL 32792
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  /18

  Est $437,500 Not Listed For Sale

  2809 Bright Bird Ln, Winter Park, FL 32792

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

  2809 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $232/SF
  • 29 Days On Market

  Last Sold Price $442,190

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  /62

  $4,995,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,738 Sq Ft

  1302 Raintree Place, Winter Park, FL 32789

  An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired

  Rikhil Amin FANNIE HILLMAN & ASSOCIATES

  1302 Raintree Place, Winter Park, FL 32789
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  /2

  $290,000 Sold Sep 22, 2025

  7102 Easter St, Winter Park, FL 32792

  • 3 Beds
  • 1 Bath
  • 1,114 Sq Ft
  • Built 1956

  Last Sold Summary

  • 3% Below List Price
  • $260/SF
  • 67 Days On Market

  Current Estimated Value $292,847

  Last Listing Agent Mayken Giraldo THE C SMITH REAL ESTATE GROUP LLC

  7102 Easter St, Winter Park, FL 32792
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  /18

  Est $435,460 Not Listed For Sale

  2805 Bright Bird Ln, Winter Park, FL 32792

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

  2805 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • $227/SF
  • 6 Days On Market

  Last Sold Price $433,390

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  /27

  $295,000

  • 3 Beds
  • 2 Baths
  • 1,178 Sq Ft

  5473 Bracken Ct, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Move-in ready 3-bedroom, 2-bath townhome in desirable Winter Park featuring recent exterior paint and a clean, modern presentation throughout. BRAND NEW water heater, A/C replaced in 2021, and NEW ROOF (2026). The spacious family room sits beneath dramatic two-story vaulted ceilings highlighted by tongue-and-groove ceiling planks, creating an open

  David Fraser KELLER WILLIAMS ADVANTAGE III

  5473 Bracken Ct, Winter Park, FL 32792
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  /2

  $805,000 Sold Jul 01, 2025

  1795 Walker Ave, Winter Park, FL 32789

  • 5 Beds
  • 3 Baths
  • 1,813 Sq Ft
  • Built 1958

  Last Sold Summary

  • 17% Below List Price
  • $444/SF
  • 143 Days On Market

  Current Estimated Value $794,536

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1795 Walker Ave, Winter Park, FL 32789
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  /18

  Est $444,247 Not Listed For Sale

  2821 Bright Bird Ln, Winter Park, FL 32792

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

  2821 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 5% Below List Price
  • $263/SF
  • 49 Days On Market

  Last Sold Price $468,490

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  /11

  $317,500

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  121 Stefanik Rd, Winter Park, FL 32792

  A MUST SEE! Beautifully remodeled 3 bedroom 2 bath home. This is a two bedroom and one bath in the front with a one bedroom one bath mother-in-law suite in the back, off of the laundry room with its own entrance as well. Main house has a large foyer and living room. Kitchen has beautiful cabinets and granite counter tops. Septic system was just replaced in September. Currently rented for $2,000

  Moe Mossa SAVVY AVENUE, LLC

  121 Stefanik Rd, Winter Park, FL 32792
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  /2

  $567,500 Sold Dec 09, 2025

  1010 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 $562,085

  Last Listing Agent Devin Loh COLDWELL BANKER REALTY

  1010 Aragon Ave, Winter Park, FL 32789
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  /18

  Est $449,368 Not Listed For Sale

  2796 Bright Bird Ln, Winter Park, FL 32792

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

  2796 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

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

  Last Sold Price $474,590

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  /29

  $415,000

  • 3 Beds
  • 2 Baths
  • 1,197 Sq Ft

  1518 Pinewood Dr, Winter Park, FL 32789

  Income-producing home with a detached in-law apartment in a prime central Orlando location — ideal for a house hack, long-term rental, or short-term rental (Airbnb allowed). The main house is a two-bedroom, one-bath residence, while the in-law apartment is a completely detached one-bedroom, one-bath unit with separate entrances and separate mailboxes, offering excellent privacy and flexibility.

  Dan Grieb KELLER WILLIAMS REALTY AT THE PARKS

  1518 Pinewood Dr, Winter Park, FL 32789
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  /2

  $2,078,500 Sold Dec 11, 2025

  715 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 $2,115,882

  Last Listing Agent Adam Roark COMPASS FLORIDA LLC

  715 Via Bella, Winter Park, FL 32789
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  /88

  Est $1,986,652 Not Listed For Sale

  1661 Hillcrest Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,161 Sq Ft
  • Built 2017

  1661 Hillcrest Ave, Winter Park, FL 32789

  Last Sold Summary

  • 10% Above List Price
  • $569/SF
  • 21 Days On Market

  Last Sold Price $1,800,000

  Last Listing Agent Domenique Lombardo ROYALTY R E BOUTIQUE INC
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  /28

  $170,000

  • 1 Bed
  • 1 Bath
  • 793 Sq Ft

  200 Saint Andrews Blvd Unit 312, Winter Park, FL 32792

  Beautifully maintained condo in a prime Winter Park location! This bright and inviting unit has been exceptionally well cared for and shows true pride of ownership. The interior is spotless, featuring a clean, modern feel with comfortable living spaces that make it easy to feel right at home. Enjoy a well-designed layout with plenty of natural light and a welcoming atmosphere throughout. The

  Reinaldo Roman ROMAN'S PRO REALTY LLC

  200 Saint Andrews Blvd Unit 312, Winter Park, FL 32792
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  /2

  $602,500 Sold May 09, 2025

  777 S Denning Dr Unit B, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 1,762 Sq Ft
  • Built 2004

  Last Sold Summary

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

  Current Estimated Value $582,504

  Last Listing Agent Susan Chapin KELLER WILLIAMS WINTER PARK

  777 S Denning Dr Unit B, Winter Park, FL 32789
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  /2

  Est $443,531 Not Listed For Sale

  2719 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,780 Sq Ft
  • Built 2024

  2719 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 8% Above List Price
  • $230/SF

  Last Sold Price $408,990

  Last Listing Agent Denise Del Castillo LPT REALTY, LLC
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  /6

  $795,000 Pending

  • Land
  • 0.22 Acre
  • $3,613,636 per Acre

  325 N Phelps Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Fantastic lot opportunity to build in one of Winter Park’s prime neighborhoods. Bring your vision and your builder to design a home tailored to your lifestyle on this 64-by-150-foot lot. The property includes a two-bedroom, one-bath single-family home with approximately 1,400 square feet of living space, making it an ideal potential income-producing

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  325 N Phelps Ave, Winter Park, FL 32789
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  /2

  $250,000 Sold Mar 11, 2026

  2009 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 $255,156

  Last Listing Agent Juliet Saldarriaga ORLANDO HOME DEALER LLC

  2009 Cornell Ave, Winter Park, FL 32789
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  /18

  Est $443,022 Not Listed For Sale

  2790 Bright Bird Ln, Winter Park, FL 32792

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

  2790 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 5% Below List Price
  • $261/SF
  • 19 Days On Market

  Last Sold Price $465,790

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
• 

  

  /33

  $320,000 Open Sun 12PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft

  2401 Antilles Dr, Winter Park, FL 32792

  Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. The home has newer A/C, high impact windows and the home has been re-piped for your peace of mind. This is a

  George Freelove KELLER WILLIAMS REALTY AT THE PARKS

  2401 Antilles Dr, Winter Park, FL 32792
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  /2

  $375,000 Sold Mar 06, 2026

  1007 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 $380,832

  Last Listing Agent Eric Gross EXP REALTY LLC

  1007 Early Ave, Winter Park, FL 32789

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