Winter Park, FL Homes

• 

  

  

  /14

  $2,289,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,334 Sq Ft

  2722 Eastern Pkwy, Winter Park, FL 32789

  Under contract-accepting backup offers. Under Construction. Masterfully designed new construction by LUIH Luxury Homes, where architectural elegance and refined livability meet an unbeatable lifestyle. Located in the Audubon Park School District just a short stroll from the iconic East End Market. From its captivating façade to its meticulously curated interiors, every element of this residence

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  2722 Eastern Pkwy, Winter Park, FL 32789
• 

  

  

  /13

  $2,550 Per Month

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • **MOVE IN SPECIAL $500 off first months rent** Beautiful 2 bedroom, 2 bath Condo located in Winte...

  110 Killarney Bay Ct, Winter Park, FL 32789

  **MOVE IN SPECIAL $500 off first months rent** Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining.Both bedrooms

  110 Killarney Bay Ct, Winter Park, FL 32789
• 

  

  /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 $1,095,027

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  1450 Chestnut Ave, Winter Park, FL 32789
• 

  

  

  /35

  Est $232,950 Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Built 1981

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

  Last Sold Summary

  • 12% Below List Price
  • $256/SF
  • 27 Days On Market

  • Last Sold Price $265,000
  • May 28, 2024

  Last Listing Agent Marina Gamundi KELLER WILLIAMS ADVANTAGE III
• 

  

  

  /32

  $144,000

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  291 Lewfield Cir Unit 291, Winter Park, FL 32792

  One of the best patio views in this community. Enjoy easy living in this cozy, open-concept first-floor condo located in a desirable Winter Park community. Step out onto your newly screened-in patio and take in the peaceful, park-like setting — a relaxing extension of your living space and the perfect spot for morning coffee or evening unwinding. Recent 2025 improvements include a new A/C system,

  Barbara Coy WATSON REALTY CORP

  291 Lewfield Cir Unit 291, Winter Park, FL 32792
• 

  

  /18

  $4,300 Per Month

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • House for Rent

  1026 S Lakemont Ave, Winter Park, FL 32792

  Lawn and pool maintenance included in rent! Welcome to this beautifully upgraded Winter Park pool home, designed for effortless living and exceptional entertaining. This 3-bedroom, 2-bath residence offers an open, inviting floor plan with a spacious kitchen featuring updated countertops and cabinetry, stainless steel appliances, beautiful bathroom finishes and updated flooring throughout. The

  Lianna D'Angelo SOTERA LIVING

  1026 S Lakemont Ave, Winter Park, FL 32792
• 

  /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 $218,304

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit J23, Winter Park, FL 32789
• 

  /2

  Est $369,133 Not Listed For Sale

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

  • 2 Beds
  • 2.5 Baths
  • 1,536 Sq Ft
  • Built 1986

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

  Last Sold Summary

  • 19% Above List Price
  • $202/SF
  • 53 Days On Market

  • Last Sold Price $310,000
  • Jul 22, 2024

  Last Listing Agent Carol van den Berg VAN DEN BERG REAL ESTATE GROUP
• 

  

  /15

  $175,000

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft

  Unlisted Address

  Welcome to this beautifully maintained 2-bedroom, 1.5-bathroom townhouse-style condominium located in the desirable Hidden Oaks Condominium community. This charming unit features a spacious living and dining area with tile flooring throughout the first floor, along with a well-appointed kitchen, breakfast nook, and convenient indoor laundry room. The home has been freshly updated with new

  Jessie Lin SOGO REAL ESTATE SERVICES LLC

  Unlisted Address
• 

  

  /37

  $2,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Affordable 3BR Home in Winter Park – Prime Location & Move-In Ready!

  151 N Orlando Ave, Winter Park, FL 32789

  Discover this affordable and well-located 3-bedroom, 2-bathroom home in the desirable Winter Park area, perfect for those seeking comfort, convenience, and long-term stability.This property offers a functional layout with comfortable living spaces, ideal for families or individuals looking for a practical and welcoming place to call home.

  151 N Orlando Ave, Winter Park, FL 32789
• 

  /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 $413,804

  Last Listing Agent Makena Clark EXIT REALTY PREMIER LEGACY

  2833 Prince John Rd, Winter Park, FL 32792
• 

  

  /24

  Est $347,721 Not Listed For Sale

  172 Balfour Dr Unit 2, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft
  • Built 1980

  172 Balfour Dr Unit 2, Winter Park, FL 32792

  Last Sold Summary

  • 12% Below List Price
  • $276/SF
  • 6 Days On Market

  • Last Sold Price $394,000
  • May 01, 2024

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES
• 

  

  /36

  $450,000 Pending

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

  665 W Lyman Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to this beautifully updated Winter Park bungalow, just steps from Hannibal Square and Park Avenue! This charming 3-bedroom, 2-bath home offers just over 1,100 square feet of thoughtfully renovated living space. The kitchen has been tastefully renovated and upgraded with modern appliances, while tile flooring runs throughout the entire home. Major

  Jonathan Nakhnoukh CENTRAL FLORIDA PRIME REAL ESTATE LLC

  665 W Lyman Ave, Winter Park, FL 32789
• 

  

  /43

  $19,000 Per Month

  • 5 Beds
  • 5.5 Baths
  • 5,164 Sq Ft
  • House for Rent

  1221 Richmond Rd, Winter Park, FL 32789

  Owner/Builder/Agent - An Award-Winning Architectural Masterpiece built by Chris Salhab of Valdara Custom Homes. 5,164 Sq Ft | 5 Bedrooms | 6 Bathrooms | Welcome to 1221 Richmond Rd, an extraordinary custom residence located in the coveted Virginia Heights neighborhood of Winter Park-offering deeded lake access to the Winter Park Chain of Lakes. This architectural showpiece was honored as the 2024

  Christopher Salhab La Rosa Realty Llc

  1221 Richmond Rd, Winter Park, FL 32789
• 

  /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 $535,099

  Last Listing Agent Joe Cremonese GLOBAL PROPERTIES SALES & MGMT

  2855 Cady Way, Winter Park, FL 32792
• 

  

  /18

  Est $434,492 Not Listed For Sale

  2786 Bright Bird Ln, Winter Park, FL 32792

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

  2786 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 2% Below List Price
  • $233/SF
  • 7 Days On Market

  • Last Sold Price $444,190
  • Apr 08, 2024

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

  

  /68

  $2,950,000

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

  151 Oakwood Way, Winter Park, FL 32789

  Welcome to 151 Oakwood Way, a beautifully executed residence by LunDev Custom Homes, set on a quiet, tree-lined street in the heart of Winter Park. Blending timeless architecture with a clean transitional aesthetic, this newer pool home offers sophisticated design, comfortable livability, and the kind of indoor-outdoor flow today’s buyers are looking for. Inside, the home is filled with natural

  Matthew Burks CORCORAN PREMIER REALTY

  151 Oakwood Way, Winter Park, FL 32789
• 

  

  /18

  $1,950 Per Month

  • 3 Beds
  • 2 Baths
  • 1,266 Sq Ft
  • Condo for Rent

  3050 Autumn Ct, Winter Park, FL 32792

  ?? Price Reduced! 3BR Condo in Winter Park – Now $1,950Don’t miss this charming 3-bedroom, 2-bath condo—now available at a reduced price! Conveniently located just off 436 in Winter Park, this home offers the perfect mix of comfort, convenience, and community living.Step inside to find tile and laminate flooring throughout, making for easy maintenance and a modern feel. Enjoy the

  3050 Autumn Ct, Winter Park, FL 32792
• 

  /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 $283,922

  Last Listing Agent Allie George CORCORAN PREMIER REALTY

  2539 Antilles Dr, Winter Park, FL 32792
• 

  

  /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
  • Apr 23, 2024

  Last Listing Agent Dee Concepcion ALL REAL ESTATE & INVESTMENTS
• 

  

  /35

  $299,999 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  3204 Netherwood Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. Discover this beautifully renovated 2-bedroom, 1.5 -bathroom villa in the heart of Winter Park! Nestled on a private cul-de-sac lot with no HOA, this home has been completely upgraded to offer modern comfort and style. Step inside to luxury vinyl flooring throughout, an open-concept living space, and a sleek kitchen with stainless steel appliances. The

  Renee Anthony WATSON REALTY CORP.

  3204 Netherwood Dr, Winter Park, FL 32792
• 

  

  /74

  $2,350 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,550 Sq Ft
  • Townhouse for Rent

  1508 Florentino Ln, Winter Park, FL 32792

  Nestled in the heart of Winter Park just off Howell Branch Rd., in the gated community of VISTAS AT LAKE HOWELL awaits this charming,spacious well equipped 2bedroom/2.5bathroom/1car garage with a loft and screen enclosed patio. This townhome features a modern aestheticfrom upgraded recessed lighting and ceiling fans, upgraded wall switches, granite counter-tops, stainless steel

  Barbarite Adams REALTY HUB

  1508 Florentino Ln, Winter Park, FL 32792
• 

  /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 $292,533

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

  7102 Easter St, Winter Park, FL 32792
• 

  

  /11

  Est $447,794 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

  • 3% Above List Price
  • $244/SF

  • Last Sold Price $434,619
  • Feb 06, 2024

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
• 

  

  /30

  $630,000

  • 5 Beds
  • 3 Baths
  • 2,472 Sq Ft

  2612 Roxbury Rd, Winter Park, FL 32789

  SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!!Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with

  Laura Mcadams EXP REALTY LLC

  2612 Roxbury Rd, Winter Park, FL 32789
• 

  

  /9

  $1,450 Per Month

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Newly remodeled 2/2 condo Winter Park $300. incentive for move in by 6/15/2026

  3651 N Goldenrod Rd Unit A104, Winter Park, FL 32792

  This 2 bedroom two bath condo has been remodeled with new tile flooring, new bathrooms and all new appliances including Washer and dryer as well as kitchen appliances, stove, fridge, dishwasher, and microwave. Community has a large community pool right outside your door. Great location with access to major roads, great dining venues and shopping possibilities. Ready for move in now. Come

  3651 N Goldenrod Rd Unit A104, Winter Park, FL 32792
• 

  /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 $788,738

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1795 Walker Ave, Winter Park, FL 32789
• 

  

  /27

  Est $162,594 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

  • 12% Below List Price
  • $244/SF
  • 3 Days On Market

  • Last Sold Price $185,000
  • Mar 26, 2024

  Last Listing Agent Melissa Johnson EXP REALTY LLC
• 

  

  /50

  $1,375,000

  • 4 Beds
  • 4 Baths
  • 3,024 Sq Ft

  2015 Summerfield Rd, Winter Park, FL 32792

  Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake Baldwin trails, and the dining and boutiques of Park Avenue. This location places you close to Rollins College, Winter Park High, and the cultural center of Winter Park FL. Inside, natural light moves through open living spaces finished with wide porcelain tile floors. The

  Christina Fata REAL BROKER, LLC

  2015 Summerfield Rd, Winter Park, FL 32792
• 

  

  /78

  $11,000 Per Month

  • 5 Beds
  • 4 Baths
  • 4,200 Sq Ft
  • House for Rent

  1814 Barker Dr, Winter Park, FL 32789

  Stunning newer-construction luxury home in Winter Park offering 5 bedrooms, 4 baths, and 4,100 sq ft of modern living. Sleek architectural lines, abundant natural light, and seamless indoor–outdoor flow define this exceptional residence. The chef’s kitchen features premium stainless steel appliances, breakfast bar, custom cabinetry, and a large walk-in pantry. The spacious living area includes a

  Tab Bish LLC REAL BROKER, LLC

  1814 Barker Dr, Winter Park, FL 32789
• 

  /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 $560,518

  Last Listing Agent Devin Loh COLDWELL BANKER REALTY

  1010 Aragon Ave, Winter Park, FL 32789
• 

  

  /46

  Est $1,225,837 Not Listed For Sale

  1778 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,377 Sq Ft
  • Built 2023

  1778 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $526/SF
  • 51 Days On Market

  • Last Sold Price $1,250,000
  • Mar 14, 2025

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
• 

  

  /25

  $284,900

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft

  2335 Inagua Way, Winter Park, FL 32792

  Rare opportunity in beautiful Winter Park - Move in ready 3 bed 2 bath townhome for under $300,000. Super low HOA at only $92/month. Spacious split plan with new roof, newer AC, new carpet in bedrooms, freshly painted, tile, inside laundry, atrium off living room and open floor plan. Patio with storage room and shed. Front entrance & parking area with beautiful pavers. Townhome is on

  Marion McGrath ABSOLUTE REALTY GROUP, LLC

  2335 Inagua Way, Winter Park, FL 32792
• 

  

  /19

  $1,250 Per Month

  • 1 Bed
  • 1 Bath
  • Townhouse for Rent

  138 Lewfield Cir, Winter Park, FL 32792

  Charming 1-Bedroom Condo in the Heart of Winter Park!Welcome to 138 Lewfield Cir – a beautifully maintained 1-bedroom, 1-bath second-floor condo offering 678 sq ft of comfortable living in the desirable Lake Howell community. From the moment you walk in, you'll feel right at home with a spacious open layout, well-sized bedroom, and a cozy living area that opens up to a private balcony

  138 Lewfield Cir, Winter Park, FL 32792
• 

  /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 $2,117,045

  Last Listing Agent Adam Roark COMPASS FLORIDA LLC

  715 Via Bella, Winter Park, FL 32789
• 

  

  /44

  Est $571,664 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

  • 4% Below List Price
  • $307/SF
  • 50 Days On Market

  • Last Sold Price $595,000
  • May 06, 2024

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS
• 

  

  /30

  $624,000

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft

  2087 Laurelwood Way, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Set within the serene gated community of Hawks Crest in Winter Park, this beautifully designed single-story home combines modern comfort with resort-style living. Featuring 4 bedrooms, 2 baths, and 1,920 sq. ft. of thoughtfully crafted space, it’s the perfect blend of style and function. Inside, an open-concept layout creates seamless flow between

  Brian Rotenberger COMPASS FLORIDA LLC

  2087 Laurelwood Way, Winter Park, FL 32792
• 

  

  /12

  $1,500 Per Month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Townhouse for Rent

  1565 Michigan Ave, Winter Park, FL 32789

  Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College.

  Troy Hensley BHHS FLORIDA REALTY

  1565 Michigan Ave, Winter Park, FL 32789
• 

  /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 $255,675

  Last Listing Agent Juliet Saldarriaga ORLANDO HOME DEALER LLC

  2009 Cornell Ave, Winter Park, FL 32789
• 

  

  /44

  Est $861,182 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

  • 7% Below List Price
  • $369/SF
  • 65 Days On Market

  • Last Sold Price $927,000
  • May 06, 2024

  Last Listing Agent Amanda Wood RE/MAX

Showing Results 481 - 520, Page 13 of 18