Winter Park, FL Homes

• 

  

  

  /29

  $2,625,000

  $70K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,048 Sq Ft

  413 W Morse Blvd, Winter Park, FL 32789

  LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, boutique shops, banks, post office, farmers market, Central Park and Rollins College. Designed by architect Phil Kean and built in 2017 the owners have embellished this townhome with custom millwork and finishes, wood floors, sound

  A.V. Blalock COLDWELL BANKER REALTY

  413 W Morse Blvd, Winter Park, FL 32789
• 

  

  

  /21

  $2,800 Per Month

  • 3 Beds
  • 2 Baths
  • 1,614 Sq Ft
  • House for Rent

  912 Carvell Dr, Winter Park, FL 32792

  Nestled in the sought-after Winter Park Estates neighborhood, this beautifully maintained 3-bedroom, 2-bathroom pool home offers the perfect blend of classic charm and modern updates. Step through the front door into a warm, welcoming living room that flows effortlessly into a dining area featuring updated kitchen finishes and quality appliances. Brand new flooring!The spacious family room

  Grace Feng INTOP REALTY LLC

  912 Carvell Dr, Winter Park, FL 32792
• 

  

  /2

  $1,850,000

  Sold Dec 15, 2025

  419 W Morse Blvd, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,027 Sq Ft
  • Built 2018

  Last Sold Summary

  • 5% Below List Price
  • $611/SF
  • 0 Days On Market

  Current Estimated Value $1,850,314

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  419 W Morse Blvd, Winter Park, FL 32789
• 

  

  

  /18

  Est $454,822

  Not Listed For Sale

  2774 Bright Bird Ln, Winter Park, FL 32792

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

  2774 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 1 Day On Market

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

  

  

  /48

  $739,777

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

  4039 Cool Water Ct, Winter Park, FL 32792

  Welcome to Lake Waunatta Woods, where neighbors become family. It is rare to find an exclusive, tight-knit community where neighbors look out for one another, and friendships feel more like family. This charming enclave of homes is a sanctuary of warmth, connection, and tranquility in a well-established Winter Park neighborhood. At the heart of this exceptional community is a beautifully

  Karen Arbutine RE/MAX CENTRAL REALTY

  4039 Cool Water Ct, Winter Park, FL 32792
• 

  

  /26

  $9,500 Per Month

  • 3 Beds
  • 3.5 Baths
  • 2,714 Sq Ft
  • Condo for Rent

  660 Osceola Ave Unit 101, Winter Park, FL 32789

  Experience the best of Winter Park waterfront living in this beautifully updated ground-floor residence at Perle du Lac, ideally located just a short stroll from the boutiques, restaurants, and cafés of Park Avenue. Even more rare, this exceptional residence includes a private covered boat slip on the pristine waters of Lake Virginia, offering direct access to the renowned Winter Park Chain of

  Jennifer King CORCORAN PREMIER REALTY

  660 Osceola Ave Unit 101, Winter Park, FL 32789
• 

  /2

  $445,000

  Sold Jun 01, 2026

  3720 Jonquil Ln, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,647 Sq Ft
  • Built 1982

  Last Sold Summary

  • $270/SF
  • 1 Day On Market

  Current Estimated Value $450,210

  Last Listing Agent Nicholas Kovats KELLER WILLIAMS ADVANTAGE REALTY

  3720 Jonquil Ln, Winter Park, FL 32792
• 

  

  /29

  Est $565,513

  Not Listed For Sale

  8097 Pleasant Pine Cir, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,003 Sq Ft
  • Built 2015

  8097 Pleasant Pine Cir, Winter Park, FL 32792

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
• 

  

  /34

  $745,000

  • 2 Beds
  • 3 Baths
  • 1,440 Sq Ft

  408 Holt Ave, Winter Park, FL 32789

  Rare investment opportunity in the heart of Winter Park/Rollins College area. This turnkey, fully renovated triplex is located within one of Winter Park’s highest-demand rental corridors, just steps from Rollins College, Park Avenue, and Lake Virginia. The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick street

  Brian Opre THE REAL ESTATE PRINCIPLE, INC

  408 Holt Ave, Winter Park, FL 32789
• 

  

  /21

  $3,150 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,803 Sq Ft
  • Townhouse for Rent

  1409 Michigan Ave, Winter Park, FL 32789

  Move-in ready and freshly painted inside and out, this spacious 3-bedroom, 2.5-bathroom Winter Park townhome features a private 2-car garage and a prime location.The bright, open-concept floor plan features a generous main living area alongside a versatile front flex room - ideal for a formal dining room or a dedicated home office. At the heart of the home is a well-appointed kitchen boasting

  Kyle Li UNIONE REALTY INC

  1409 Michigan Ave, Winter Park, FL 32789
• 

  /2

  $684,000

  Sold Dec 23, 2025

  1909 Cyril Ct, Winter Park, FL 32792

  • 3 Beds
  • 3.5 Baths
  • 3,102 Sq Ft
  • Built 1990

  Last Sold Summary

  • 9% Below List Price
  • $221/SF
  • 56 Days On Market

  Current Estimated Value $700,413

  Last Listing Agent James Hurst, II JAMES F. HURST II, BROKER

  1909 Cyril Ct, Winter Park, FL 32792
• 

  

  /16

  Est $186,515

  Not Listed For Sale

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

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Built 1984

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

  Last Sold Summary

  • 132 Days On Market

  Last Listing Agent ALLISON JOHNSTON THE SIMON SIMAAN GROUP
• 

  

  /64

  $3,750,000

  New Construction $1M PRICE DROP Under Contract

  • 4 Beds
  • 5.5 Baths
  • 3,826 Sq Ft

  1150 Via Salerno, Winter Park, FL 32789

  Under contract-accepting backup offers. In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement with organic warmth. Now offered at a compelling new price, the home presents a rare opportunity to experience architecturally distinctive new construction in the Vias neighborhood. Conceived, developed & designed by

  Padgett McCormick KELLY PRICE & COMPANY LLC

  1150 Via Salerno, Winter Park, FL 32789
• 

  

  /9

  $2,200 Per Month

  • 3 Beds
  • 2 Baths
  • 1,068 Sq Ft
  • House for Rent

  1751 Westchester Ave, Winter Park, FL 32789

  Move-in ready 3-bedroom, 2-bath home in a convenient Winter Park location just off Orange Avenue and minutes from Park Avenue. The home features updated vinyl flooring, fresh interior paint and fixtures, a kitchen with new appliances included, comfortable single-story layout, screened lanai, covered carport, and private backyard. Enjoy quick access to Downtown Winter Park, Park Avenue’s shops,

  Ahmad Hassan COMPASS FLORIDA LLC

  1751 Westchester Ave, Winter Park, FL 32789
• 

  /2

  $445,000

  Sold Jul 02, 2026

  1468 Auburn Green Loop, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,676 Sq Ft
  • Built 1984

  Last Sold Summary

  • 7% Below List Price
  • $266/SF
  • 26 Days On Market

  Current Estimated Value $471,349

  Last Listing Agent Jodie Ma COLDWELL BANKER VANGUARD EDGE REALTY

  1468 Auburn Green Loop, Winter Park, FL 32792
• 

  

  /10

  Est $433,411

  Not Listed For Sale

  2726 Bright Bird Ln, Winter Park, FL 32792

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

  2726 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE
• 

  

  /26

  $599,000

  • 3 Beds
  • 2 Baths
  • 2,031 Sq Ft

  4026 Tenita Dr, Winter Park, FL 32792

  MOVE IN READY! New roof, new bathrooms, new kitchen, new floors, new electrical panels and more. Located in the beautiful lake community of Lake Waunatta Woods. Large private lot on greenbelt. 3 bedroom, 2 bath POOL home with 2 masters and split floor plan. The second master has outside entrance for option to use as a mother-in-law suite or rental. Spacious living room/dining room, family room,

  Ruby Davis RUBY DAVIS, BROKER

  4026 Tenita Dr, Winter Park, FL 32792
• 

  /2

  $2,200 Per Month

  • 3 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • House for Rent

  128 Oak Grove Rd, Winter Park, FL 32789

  Charming 3-bedroom, 2-bathroom home in a desirable Winter Park location, within walking distance of the new Life Time Fitness. This bright and inviting residence features an open floor plan, tile flooring, large windows, and a well-appointed kitchen with granite countertops. The fenced backyard provides a private space for relaxing or entertaining, while the attached one-car garage offers added

  Lafa Britto NOVA REAL ESTATE SERVICES INC

  128 Oak Grove Rd, Winter Park, FL 32789
• 

  /2

  $3,800,000

  Sold Feb 24, 2026

  637 N Park Ave, Winter Park, FL 32789

  • 3 Beds
  • 5 Baths
  • 4,237 Sq Ft
  • Built 2019

  Last Sold Summary

  • 2% Below List Price
  • $897/SF
  • 24 Days On Market

  Current Estimated Value $3,815,914

  Last Listing Agent Whitney Johnson COLDWELL BANKER REALTY

  637 N Park Ave, Winter Park, FL 32789
• 

  

  /25

  Est $2,077,014

  Not Listed For Sale

  1925 Killarney Dr, Winter Park, FL 32789

  1925 Killarney Dr, Winter Park, FL 32789

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Cathy Marino CATHY S. MARINO REALTY, INC.

Showing Results 681 - 720, Page 18 of 18