Winter Park, FL Homes

• 

  

  

  /89

  $1,999,993

  • 6 Beds
  • 4 Baths
  • 3,853 Sq Ft

  1451 Lyndale Blvd, Winter Park, FL 32789

  **Luxurious Winter Park Estate with Detached TWO bedroom Guest House** RENOVATED POOL HOME with NO HOA! TWO Primary Bedrooms located on the main floor! Welcome to a world of unparalleled luxury and elegance in the heart of historic Winter Park, FL. This exquisitely renovated two-story pool home, set on a sprawling corner lot, offers a rare opportunity to experience the pinnacle of

  Christopher Soucy REALTY ONE GROUP MVP

  1451 Lyndale Blvd, Winter Park, FL 32789
• 

  

  

  /38

  $8,990 per month

  • 4 Beds
  • 3.5 Baths
  • 4,188 Sq Ft
  • House for Rent

  2020 Venetian Way, Winter Park, FL 32789

  Only available for a 4 to 6 month lease. This RARE LAKEFRONT retreat is located on a quiet, tree-lined street in the highly sought-after Vias of Winter Park. Custom-built and elevated on a prime lot with 90 feet of frontage on Lake Maitland, this one-of-a-kind mid-century home offers sweeping views of Lake Maitland and the Isle of Sicily. It combines timeless design, complete privacy, and a

  Nadia Moayeri PALMANO GROUP RE BROKERAGE LLC

  2020 Venetian Way, Winter Park, FL 32789
• 

  

  

  /51

  $704,700 Sold Mar 11, 2025

  350 Carolina Ave Unit 301, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,544 Sq Ft
  • Built 2006

  Last Sold Summary

  • 3% Below List Price
  • $456/SF
  • 26 Days On Market

  Current Estimated Value $706,914

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  350 Carolina Ave Unit 301, Winter Park, FL 32789
• 

  

  /2

  Est $91,131 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 549 Sq Ft

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

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

  

  

  /22

  $439,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,661 Sq Ft

  2743 Merrie Oaks Rd, Winter Park, FL 32792

  Welcome home to this 3-bedroom, 2-bath residence featuring a spacious 2-car garage and a long list of valuable updates. Enjoy peace of mind with a re-roof (2017), whole-home re-plumb with Pex and PVC (2024), new A/C system (2024), and new modern ceramic tile flooring in the kitchen, family room, foyer and hallway (2024). The hot water heater was replaced in 2022, and the home is enhanced with

  Julio Zayas ONE45 REALTY LLC

  2743 Merrie Oaks Rd, Winter Park, FL 32792
• 

  

  /13

  $2,650 per month

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Townhouse for Rent

  3486 Bougainvillea Dr Unit B, Winter Park, FL 32792

  Location! Location! Location! This exactly what you are looking for, a nice home in a great location. This a great unit featuring a nice kitchen with stainless steel appliances, and an updated flooring with luxury vinyl plank. This unit has an indoor heated swimming pool with an exercise room. This property is located near all of the main central Florida colleges. Come and enjoy with your family

  Smithj Salomon LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  3486 Bougainvillea Dr Unit B, Winter Park, FL 32792
• 

  /2

  $935,000 Sold Dec 19, 2025

  7706 Waunatta Ct, Winter Park, FL 32792

  • 5 Beds
  • 3 Baths
  • 3,858 Sq Ft
  • Built 1978

  Last Sold Summary

  • 11% Below List Price
  • $242/SF
  • 70 Days On Market

  Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC

  7706 Waunatta Ct, Winter Park, FL 32792
• 

  

  /18

  Est $425,000 Not Listed For Sale

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

  1916 Erudite Way, Winter Park, FL 32792

  1916 Erudite Way, Winter Park, FL 32792
• 

  

  /41

  $155,000

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit D116, Winter Park, FL 32789

  PRICE IMPROVEMENT! Best priced unit in the entire community! Location, location, location!! Priced to sell!! This 3 bedroom 2 bathroom corner unit first floor condo is conveniently located within a short drive distance to Rollins College, UCF, Valencia College, hospitals, shopping, dining, and entertainment! The unit is located on the first floor and has an open floor plan, spacious kitchen

  Madalay Fleming LA ROSA REALTY KISSIMMEE

  1695 Lee Rd Unit D116, Winter Park, FL 32789
• 

  

  /12

  $1,450 per month

  • 2 Beds
  • 2 Baths
  • 1,003 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 115, Winter Park, FL 32792

  Welcome to Golfside Villas. This community is nestled near Downtown Orlando, Full Sail, UCF, Lynx bus stop, major shopping centers, restaurants, I-4, 408, & Orlando International Airport. This condominium features an open floor plan that consist of 2 bedrooms, 2 bathrooms, and a screened in patio. Over 1000 sqft of living space awaits you with a few upgrades. This neighborhood features a laundry

  Damon Mayers MAYERS REAL ESTATE LLC

  1000 S Semoran Blvd Unit 115, Winter Park, FL 32792
• 

  /2

  $1,110,000 Sold Aug 26, 2025

  233 Hampden Place, Winter Park, FL 32789

  • 5 Beds
  • 3 Baths
  • 2,813 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $395/SF
  • 7 Days On Market

  Current Estimated Value $1,161,867

  Last Listing Agent Frank Ferrell FERRELL REALTY, INC.

  233 Hampden Place, Winter Park, FL 32789
• 

  /2

  Est $523,051 Not Listed For Sale

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

  1051 Aragon Ave Unit 1051, Winter Park, FL 32789

  1051 Aragon Ave Unit 1051, Winter Park, FL 32789
• 

  

  /38

  $499,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,738 Sq Ft

  1116 Fairway Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. One or more photos has been virtually staged. Welcome to this beautiful, single-family home in the Golfside Community in Winter Park! This stunning 3-bedroom, 2-bathroom residence offers a living space of 1,738 square feet. When you enter the home, you step right into the family room. To the right of it, you

  Mathew Kelly TURN-KEY MOVES REALTY

  1116 Fairway Dr, Winter Park, FL 32792
• 

  

  /19

  $1,425 per month

  • 2 Beds
  • 2.5 Baths
  • 1,090 Sq Ft
  • Condo for Rent

  3007 George Mason Ave Unit H-3D, Winter Park, FL 32792

  HOLIDAY MOVE-IN SPECIAL!Apply and get approved by 12/31/25 and receive 1⁄2 month off PLUS your application fee back at move-in (up to $85).Terms apply Move-in ready and beautifully updated, this two-story condo in the desirable Colonies Community offers 2 bedrooms and 2.5 bathrooms, with each bedroom featuring its own private en-suite bath. All bedrooms are located upstairs. While a

  Alex Zweydoff ALLEGIANT MANAGEMENT GROUP INC

  3007 George Mason Ave Unit H-3D, Winter Park, FL 32792
• 

  /2

  $200,000 Sold Sep 13, 2025

  3251 Oak Lake Place Unit 135, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft
  • Built 1984

  Last Sold Summary

  • 11% Below List Price
  • $174/SF
  • 131 Days On Market

  Current Estimated Value $201,614

  Last Listing Agent Nick Nesta, III NESTA REAL ESTATE CONSULTANTS

  3251 Oak Lake Place Unit 135, Winter Park, FL 32792
• 

  

  /39

  Est $1,613,998 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,345 Sq Ft

  1007 S Pennsylvania Ave, Winter Park, FL 32789

  1007 S Pennsylvania Ave, Winter Park, FL 32789
• 

  

  /65

  $2,295,000

  • 3 Beds
  • 3.5 Baths
  • 2,714 Sq Ft

  660 Osceola Ave Unit 101, Winter Park, FL 32789

  Imagine waking, relaxing, and entertaining with serene lakefront views in this elegant ground-floor Perle du Lac residence. The refined 2,714-square-foot design includes hardwood and travertine flooring, ten-foot-high ceilings, and extensive millwork. The expansive open-plan living and dining room lets you configure your furniture however you’d like. A bank of glass doors leads to your covered

  Richard Traynor FLORIDA ONE REAL ESTATE LLC

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

  

  /9

  $702,000 per month

  • Property for Rent

  7839 University Garden Dr, Winter Park, FL 32792

  Build your dream home on 4.93 acres in Winter Park. No HOA, lot dimensions 665ft x 323ft, zoning A-2/FARMLAND RURAL, land use vacant residential. The sale price included 2 parcels 11 22 30 0000 00 125 & 11 22 30 0000 00 042 with a factory home 3/2, 1344 sf. heated, built in 1976, and a mobile home. Convenient to SR-551/ Goldenrod Rd, SR-426/Aloma Rd, SR-50/Colonial Dr, University Blvd, FL-417,

  Shettle Huynh FLORIDA REALTY INVESTMENTS

  7839 University Garden Dr, Winter Park, FL 32792
• 

  /2

  $1,575,000 Sold Dec 27, 2024

  2435 Chantilly Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,055 Sq Ft
  • Built 2023

  Last Sold Summary

  • 5% Below List Price
  • $516/SF
  • 42 Days On Market

  Current Estimated Value $1,580,443

  Last Listing Agent Aleksey Volchek FLORIDA REALTY INVESTMENTS

  2435 Chantilly Ave, Winter Park, FL 32789
• 

  

  /32

  Est $463,835 Not Listed For Sale

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

  2445 Firstlight Way, Winter Park, FL 32792

  2445 Firstlight Way, Winter Park, FL 32792
• 

  

  /15

  $425,000

  • Land
  • 0.11 Acre
  • $3,863,636 per Acre

  786 W Canton Ave, Winter Park, FL 32789

  Incredible opportunity for the right family. This is a 49x96 Perfectly high and dry lot with a tree to shade your backyard. Nestled in the highly sought after City of Winter Park amongst million dollar homes. LOCATION LOCATION LOCATION! A perfect home site for your future custom dwelling. Bring your imagination creativity and builder to take a look. What a Winter Park sweet spot. Lots in this

  Laurie Cash Cain CHARLES RUTENBERG REALTY ORLANDO

  786 W Canton Ave, Winter Park, FL 32789
• 

  

  /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
• 

  /2

  $292,000 Sold Feb 28, 2025

  2690 Granada Run, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $199/SF
  • 33 Days On Market

  Current Estimated Value $294,845

  Last Listing Agent Jacquie Sosa EXP REALTY LLC

  2690 Granada Run, Winter Park, FL 32792
• 

  

  /62

  Est $1,969,509 Not Listed For Sale

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

  2156 Talman Ct, Winter Park, FL 32792

  2156 Talman Ct, Winter Park, FL 32792
• 

  

  /31

  $635,000

  • 3 Beds
  • 2.5 Baths
  • 1,798 Sq Ft

  1267 Michigan Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Modern Comfort in the Heart of Winter Park! Built in 2019, this 3-bedroom, 2-bath, 1,798sf townhome offers the perfect blend of convenience and contemporary style in a private 12-unit community. Light and bright with high ceilings and tile floors, the open-concept living area features a quartz island kitchen with Samsung appliances, solid wood

  Megan Cross FANNIE HILLMAN & ASSOCIATES

  1267 Michigan Ave, Winter Park, FL 32789
• 

  

  /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
• 

  /2

  $3,200,000 Sold Nov 04, 2025

  1900 W Fawsett Rd, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,600 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $696/SF
  • 6 Days On Market

  Last Listing Agent Bianca Rey KELLER WILLIAMS WINTER PARK

  1900 W Fawsett Rd, Winter Park, FL 32789
• 

  

  /20

  Est $466,606 Not Listed For Sale

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

  2448 Firstlight Way, Winter Park, FL 32792

  2448 Firstlight Way, Winter Park, FL 32792
• 

  

  /48

  $4,950,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 6,406 Sq Ft

  1660 Palmer Ave, Winter Park, FL 32789

  New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1660 Palmer Ave, Winter Park, FL 32789
• 

  /2

  $1,750 per month

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Townhouse for Rent

  7412 Woodburn Ct Unit 23, Winter Park, FL 32792

  Great townhouse in Winter Park. Winter Park Schoolls. Close to everything, shopping, Costco, restaurants, Valencia Community College East Campus and The University of Central Florida. Close to Siemens and Lockheed Martin. Easy access to main Arteries 408 to all others. The townhouse has been professionally painted in 2019 and new cabinets doors were placed in the kitchen in 2020. New disposal and

  Dyna Stephens POWERHOUSE BROKERS INT'L

  7412 Woodburn Ct Unit 23, Winter Park, FL 32792
• 

  /2

  $1,850,000 Sold Apr 07, 2025

  2248 Middleton Ave, Winter Park, FL 32792

  • 4 Beds
  • 4.5 Baths
  • 3,505 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $528/SF
  • 10 Days On Market

  Current Estimated Value $1,806,733

  Last Listing Agent Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

  2248 Middleton Ave, Winter Park, FL 32792
• 

  

  /22

  Est $196,323 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792
• 

  

  /46

  $4,250,000 New Construction

  • 4 Beds
  • 5.5 Baths
  • 3,720 Sq Ft

  702 Via Bella, Winter Park, FL 32789

  Welcome to 702 Via Bella, an impressive 2025 English cottage estate by Floridian Custom Homes that captures the essence of timeless architecture exemplifying elegance and artisan craftsmanship. In one of Winter Park’s desirable residential corridors, warmth and beauty abound in this four-bedroom, six-bath residence spanning 3,720 square feet or air conditioned and 4,535 square feet total under

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  702 Via Bella, Winter Park, FL 32789
• 

  /2

  $428,000 Sold Jan 21, 2025

  5142 Tangerine Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,563 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Above List Price
  • $274/SF
  • 5 Days On Market

  Current Estimated Value $423,797

  Last Listing Agent Lorry Robles EXP REALTY LLC

  5142 Tangerine Ave, Winter Park, FL 32792
• 

  

  /77

  Est $787,104 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,496 Sq Ft

  7904 Pleasant Pine Cir, Winter Park, FL 32792

  7904 Pleasant Pine Cir, Winter Park, FL 32792
• 

  

  /16

  $40,000

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft

  3028 George Mason Ave Unit 7, Winter Park, FL 32792

  Two-bedroom two bath in the Winter Park School District. Convenient to shopping and bus service. Property needs rehab.

  David Rollins FLORIDA REALTY INVESTMENTS

  3028 George Mason Ave Unit 7, Winter Park, FL 32792
• 

  /2

  $879,000 Sold Nov 14, 2025

  451 Fairfax Ave, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,227 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $395/SF
  • 5 Days On Market

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

  451 Fairfax Ave, Winter Park, FL 32789
• 

  

  /28

  Est $263,098 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft

  7113 Swallow Run Unit 2, Winter Park, FL 32792

  7113 Swallow Run Unit 2, Winter Park, FL 32792
• 

  

  /34

  $339,000

  • 4 Beds
  • 2 Baths
  • 1,242 Sq Ft

  5047 Ferncrest Dr, Winter Park, FL 32792

  Lovingly Maintained by original owner. This is a true 4 bedroom home with 2 bathrooms and a single car garage. Located in desirable Winter Park with easy access to major roads, convenient to shopping, the post office, restaurants, higher education, and airports. This solid built home features a split plan, large living room with a wall of closet space, easy access walk - through kitchen, screened

  Wanda Perkins GLOBAL PROPERTIES SALES & MGMT

  5047 Ferncrest Dr, Winter Park, FL 32792
• 

  /2

  $630,000 Sold Aug 11, 2025

  1792 Killarney Dr, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,264 Sq Ft
  • Built 1958

  Last Sold Summary

  • 3% Below List Price
  • $278/SF
  • 1 Day On Market

  Current Estimated Value $633,705

  Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

  1792 Killarney Dr, Winter Park, FL 32789

Showing Results 601 - 640, Page 16 of 18