Winter Park, FL Homes

• 

  

  

  /35

  $899,999

  • 6 Beds
  • 5 Baths
  • 3,715 Sq Ft

  4571 Kawilla Crest Place, Winter Park, FL 32792

  Welcome to this beautifully updated home located in the Winter Park area with a Private Mother in Law Suite! This property has been thoughtfully upgraded throughout, offering peace of mind and modern living at its finest. Major system updates include a roof replaced in 2019, solar installed in 2020 (paid off at closing), new electric water heater (2026), and both AC units replaced, providing

  Jeremy Toro THE WILKINS WAY LLC

  4571 Kawilla Crest Place, Winter Park, FL 32792
• 

  

  

  /16

  $2,675 Per Month

  • 3 Beds
  • 2 Baths
  • 1,525 Sq Ft
  • House for Rent

  1721 Shasta Ct, Winter Park, FL 32792

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  (407) 641-3217

  1721 Shasta Ct, Winter Park, FL 32792
• 

  

  /2

  $660,000 Sold Nov 17, 2025

  2421 Summerfield Rd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,256 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $293/SF
  • 6 Days On Market

  Current Estimated Value $650,425

  Last Listing Agent Simi Lakhani KELLER WILLIAMS CLASSIC

  2421 Summerfield Rd, Winter Park, FL 32792
• 

  

  

  /24

  Est $197,647 Not Listed For Sale

  200 Saint Andrews Blvd Unit 2210, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 2210, Winter Park, FL 32792

  Last Sold Summary

  • 21% Below List Price
  • $253/SF
  • 0 Days On Market

  • Last Sold Price $250,000
  • Jun 30, 2023

  Last Listing Agent Kelsey Taylor EXP REALTY LLC
• 

  

  

  /25

  $209,900

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft

  4858 Tangerine Ave Unit 4858, Winter Park, FL 32792

  Charming Updated Home in Prime Winter Park Location Welcome to this beautifully updated home located in the highly desirable area of Winter Park. Combining comfort, style, and convenience, this property offers a thoughtfully designed open floor plan that creates a seamless flow between the main living spaces, making it ideal for both everyday living and entertaining. The home features two

  Angelica Diaz Bajo WRA BUSINESS & REAL ESTATE

  4858 Tangerine Ave Unit 4858, Winter Park, FL 32792
• 

  

  /17

  $2,530 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,482 Sq Ft
  • House for Rent

  3313 Hamlet Loop, Winter Park, FL 32792

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

  (689) 329-3269

  3313 Hamlet Loop, Winter Park, FL 32792
• 

  /2

  $498,000 Sold May 28, 2025

  808 Denton Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 1961

  Last Sold Summary

  • $286/SF
  • 4 Days On Market

  Current Estimated Value $488,555

  Last Listing Agent Julie Vega-Dominguez PREMIER SOTHEBY'S INTL. REALTY

  808 Denton Rd, Winter Park, FL 32792
• 

  /2

  Est $1,549,094 Not Listed For Sale

  101 S New York Ave Unit 303, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,174 Sq Ft
  • Built 2009

  101 S New York Ave Unit 303, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $496/SF
  • 129 Days On Market

  • Last Sold Price $1,575,000
  • Jan 10, 2025

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES
• 

  

  /45

  $205,000

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

  3371 River View Way Unit 46, Winter Park, FL 32792

  Welcome to Unit 46 at Hidden Oaks, a townhome-style condo nestled in one of Winter Park's most convenient and well-established communities. Ideal for first-time buyers, down-sizers, or investors looking for location and lifestyle in one. The floor plan offers three bedrooms upstairs with two full bathrooms, plus a half bath on the main level — perfect for guests and everyday living. Two reserved

  Safiya Bourne REALTY ONE GROUP EVOLVE

  3371 River View Way Unit 46, Winter Park, FL 32792
• 

  /2

  $3,395 Per Month

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • House for Rent

  1937 Strathaven Rd, Winter Park, FL 32792

  Property Id: 158416INTERIOR PICTURES COMING SOON * Newly renovated kitchen * All new appliances * All new flooring * Freshly painted * Updated Baths * Open Floor Plan * Large living room * Large sun room * Great Fenced Yard * Includes New Washer / Dryer * Over-sized 2 Car Garage * Great schools * Quite Neighborhood * Rent includes lawn care and pest control

  (689) 220-1342

  1937 Strathaven Rd, Winter Park, FL 32792
• 

  /2

  $3,485,000 Sold Oct 17, 2025

  2171 Forrest Rd, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,565 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $763/SF
  • 134 Days On Market

  Current Estimated Value $3,358,092

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

  2171 Forrest Rd, Winter Park, FL 32789
• 

  

  /38

  Est $3,053,798 Not Listed For Sale

  140 E Morse Blvd Unit G, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,367 Sq Ft
  • Built 2008

  140 E Morse Blvd Unit G, Winter Park, FL 32789

  Last Sold Summary

  • 5% Below List Price
  • $950/SF
  • 3 Days On Market

  • Last Sold Price $3,200,000
  • Jul 31, 2023

  Last Listing Agent Andrea Sider, PA KELLER WILLIAMS WINTER PARK
• 

  

  /74

  $925,000

  • 4 Beds
  • 2 Baths
  • 3,950 Sq Ft

  1521 Heron Wood Place, Winter Park, FL 32792

  Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides immediate income for a hands-on owner or family-run operation.One structure is currently utilized for daycare operations, while the second structure is a single-family home that offers excellent potential for future daycare

  Ronald Trotter RE/MAX INNOVATION

  1521 Heron Wood Place, Winter Park, FL 32792
• 

  

  /3

  $2,300 Per Month

  • 3 Beds
  • 1 Bath
  • 1,260 Sq Ft
  • Condo for Rent

  2827 Riddle Dr, Winter Park, FL 32789

  Welcome to your new oasis in the charming city of Winter Park, FL! This beautiful property is perfect for those seeking comfort and convenience in a vibrant community. With nearby restaurants offering a delightful culinary experience, you'll always have something new to explore.This property features spacious accommodations designed for your relaxation. Enjoy a comfortable living

  (321) 381-3659

  2827 Riddle Dr, Winter Park, FL 32789
• 

  /2

  $1,645,000 Sold May 20, 2025

  681 Balmoral Rd, Winter Park, FL 32789

  • Land
  • 1.14 Acres
  • $1,442,982 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 55 Days On Market

  Current Estimated Value $1,598,071

  Last Listing Agent Chris Burden EPIC REAL ESTATE ADVISORS LLC

  681 Balmoral Rd, Winter Park, FL 32789
• 

  

  /30

  Est $1,429,852 Not Listed For Sale

  311 E Morse Blvd Unit 1-1, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,066 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 1-1, Winter Park, FL 32789

  Last Sold Summary

  • 8% Below List Price
  • $749/SF
  • 0 Days On Market

  • Last Sold Price $1,547,500
  • Dec 16, 2023

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

  

  /44

  $899,000

  • 3 Beds
  • 2 Baths
  • 2,003 Sq Ft

  1507 Golfside Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW

  Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  1507 Golfside Dr, Winter Park, FL 32792
• 

  

  /47

  $2,675 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Townhouse for Rent

  2760 Bright Bird Ln, Winter Park, FL 32792

  Stunning 3 beds/2.5 bath/1car garage townhome ready to move-in June at Grayson Square, Winter park. RENT INCLUDES high-speed 1GB fiber optic internet & 75 streaming cable and music channels. The first floor is efficiently laid out with the kitchen, powder room, and spacious gathering room perfect for entertaining with a sliding glass door that opens to the covered lanai and patio that overlooks a

  Fabian Berastegui P & C PROPERTIES

  2760 Bright Bird Ln, Winter Park, FL 32792
• 

  /2

  $335,000 Sold Sep 23, 2025

  5144 N Orange Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 1976

  Last Sold Summary

  • 16% Below List Price
  • $263/SF
  • 128 Days On Market

  Current Estimated Value $337,543

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  5144 N Orange Ave, Winter Park, FL 32792
• 

  

  /47

  Est $246,528 Not Listed For Sale

  200 Saint Andrews Blvd Unit 1203, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,322 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 1203, Winter Park, FL 32792

  Last Sold Summary

  • 16% Below List Price
  • $222/SF
  • 8 Days On Market

  • Last Sold Price $293,455
  • May 19, 2023

  Last Listing Agent Steven Luppert COMPASS FLORIDA LLC
• 

  

  /11

  $198,000

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft

  3060 George Mason Ave Unit 12, Winter Park, FL 32792

  Welcome to your new home in Winter Park!Completely remodeled unit with luxury finishes, ceramic floors, modern bathrooms, brand new kitchen with steel appliances and a nice quartz counter. Community amenities include pool, tennis and playground. Great Schools - zoned for Winter Park HS. Just minutes to Full Sail, UCF & Valencia. Don’t miss out on this gem!

  Adriana Sanchez WF REALTY CORP.

  3060 George Mason Ave Unit 12, Winter Park, FL 32792
• 

  

  /15

  $2,125 Per Month

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • House for Rent

  1407 Chilean Ln, Winter Park, FL 32792

  We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be

  1407 Chilean Ln, Winter Park, FL 32792
• 

  /2

  $397,000 Sold Jul 01, 2025

  1109 Denton Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,236 Sq Ft
  • Built 1963

  Last Sold Summary

  • 3% Below List Price
  • $321/SF
  • 83 Days On Market

  Current Estimated Value $398,354

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1109 Denton Rd, Winter Park, FL 32792
• 

  

  /64

  Est $648,645 Not Listed For Sale

  1327 Fountain Hills Ct, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,575 Sq Ft
  • Built 2017

  1327 Fountain Hills Ct, Winter Park, FL 32792

  Last Sold Summary

  • $252/SF
  • 0 Days On Market

  • Last Sold Price $650,000
  • May 24, 2023

  Last Listing Agent Brannon Ogburn JPAR SOUTH FLORIDA LIVING
• 

  

  /49

  $189,999

  • 2 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  7468 Canford Ct Unit 24, Winter Park, FL 32792

  This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spacious living areas and thoughtful storage throughout. The community features deluxe vinyl fencing installed by the HOA, along with a clubhouse and a community pool, providing great amenities for residents to enjoy. Inside, you’ll find the convenience of an in-unit washer and dryer combo, ample storage under

  Javier Albelo Rivera EMPIRE NETWORK REALTY

  7468 Canford Ct Unit 24, Winter Park, FL 32792
• 

  

  /11

  $2,350 Per Month

  • 3 Beds
  • 2 Baths
  • 1,355 Sq Ft
  • House for Rent

  1931 Staunton Ave, Winter Park, FL 32789

  Available for rent! Tucked onto a desirable corner lot just steps from Lake Killarney, this beautifully updated 3 bedroom, 2 bath single-family home puts you in one of the area's most sought-after spots. Walkable, quiet, and moments from the water. Inside, the home is move-in ready with a full suite of brand-new appliances (dishwasher, range, and refrigerator) plus washer/dryer hookups ready for

  Zach Mitchell SAND DOLLAR REALTY GROUP INC

  1931 Staunton Ave, Winter Park, FL 32789
• 

  /2

  $145,000 Sold Aug 13, 2025

  7352 Swallow Run, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 802 Sq Ft
  • Built 1983

  Last Sold Summary

  • 39% Below List Price
  • $181/SF
  • 68 Days On Market

  Current Estimated Value $142,632

  Last Listing Agent Ashley Quandt LEERDAM PROPERTIES INC.

  7352 Swallow Run, Winter Park, FL 32792
• 

  /2

  Est $366,901 Not Listed For Sale

  1312 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 864 Sq Ft
  • Built 1983

  1312 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  Last Sold Summary

  • 14% Below List Price
  • $492/SF
  • 36 Days On Market

  • Last Sold Price $425,000
  • Oct 17, 2024

  Last Listing Agent Jenni Owens KELLER WILLIAMS WINTER PARK
• 

  

  /48

  $1,175,000

  • 5 Beds
  • 3 Baths
  • 2,656 Sq Ft

  2702 Parkland Dr, Winter Park, FL 32789

  Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace

  Elizabeth Nordquist NORDQUIST & COMPANY INC

  2702 Parkland Dr, Winter Park, FL 32789
• 

  

  /15

  $2,175 Per Month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  3091 Crane Strand Dr, Winter Park, FL 32792

  We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be

  3091 Crane Strand Dr, Winter Park, FL 32792
• 

  /2

  $228,000 Sold Jun 27, 2025

  1979 Staunton Ave, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft
  • Built 1948

  Last Sold Summary

  • 24% Below List Price
  • $310/SF
  • 16 Days On Market

  Current Estimated Value $226,368

  Last Listing Agent Michael Kara CORBELO LLC

  1979 Staunton Ave, Winter Park, FL 32789
• 

  /2

  Est $820,333 Not Listed For Sale

  2320 Janice Ave, Winter Park, FL 32789

  2320 Janice Ave, Winter Park, FL 32789

  Last Sold Summary

  • 3% Above List Price
  • 2 Days On Market

  • Last Sold Price $799,000
  • Apr 30, 2025

  Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES
• 

  

  /15

  $219,900

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7771 Country Place Unit 7, Winter Park, FL 32792

  Motivated Seller....Fantastic 3-Bedroom, 2-Bathroom Condo Located in the Highly Desirable Winter Park Area! This Home Features an Open Galley Kitchen with a High Vaulted Ceiling and a Convenient Pantry. The Spacious Living/Dining Room Combination Also Boasts Vaulted Ceilings and Fills with Natural Light Through the Sliding Glass Doors, Creating an Inviting Yet Cozy Atmosphere. Beautiful Laminate

  Ivan Tobon OUTLET REALTY

  7771 Country Place Unit 7, Winter Park, FL 32792
• 

  

  /24

  $2,599 Per Month

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft
  • House for Rent

  3465 Balsam Dr, Winter Park, FL 32792

  Welcome to this charming 3-bedroom, 2-bathroom home located in a well-established Winter Park neighborhood. This property offers a comfortable single-story layout with inviting living spaces, ideal for everyday living and entertaining. The home features a functional floor plan with a bright living area, an eat-in kitchen, and well-sized bedrooms, including a primary suite with a private bath.

  Steve Simpson 407 PROPERTIES

  3465 Balsam Dr, Winter Park, FL 32792
• 

  /2

  $1,905,000 Sold Apr 10, 2026

  501 Henkel Cir, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,746 Sq Ft
  • Built 2009

  Last Sold Summary

  • 4% Above List Price
  • $509/SF
  • 4 Days On Market

  Current Estimated Value $1,855,042

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  501 Henkel Cir, Winter Park, FL 32789
• 

  /2

  Est $263,588 Not Listed For Sale

  609 Gallery Dr Unit 2, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 929 Sq Ft
  • Built 1984

  609 Gallery Dr Unit 2, Winter Park, FL 32792

  Last Sold Summary

  • 2% Below List Price
  • $291/SF
  • 12 Days On Market

  • Last Sold Price $270,000
  • Apr 04, 2025

  Last Listing Agent Kim Oliver NONA LEGACY POWERED BY LA ROSA
• 

  

  /47

  $899,000

  • 3 Beds
  • 3 Baths
  • 1,864 Sq Ft

  1960 E Winter Park Rd, Winter Park, FL 32789

  Discover the perfect canvas for your dream home at 1960 Winter Park Road! With utilities and sewer connected, plus a complete roof replacement in 2019, newer gutters with gutter guards added in 2020, and various new appliances and thoughtful upgrades since, this 1⁄4-acre lot presents the ideal opportunity to either build new, or remodel.Zoned for the highly esteemed Audubon K-8 School, this

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1960 E Winter Park Rd, Winter Park, FL 32789
• 

  

  /83

  $2,695

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 990 Sq Ft
  • Condo for Rent

  2007 Cornell Ave Unit SI ID1032296P, Winter Park, FL 32789

  The advertised rate of $2,696/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 22, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  2007 Cornell Ave Unit SI ID1032296P, Winter Park, FL 32789
• 

  /2

  $399,900 Sold Oct 08, 2025

  7553 Laurel Springs Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Built 1973

  Last Sold Summary

  • $338/SF
  • 20 Days On Market

  Current Estimated Value $393,107

  Last Listing Agent Yamila Lopez EMPIRE NETWORK REALTY

  7553 Laurel Springs Dr, Winter Park, FL 32792
• 

  /2

  Not Listed For Sale

  3045 Aaron Burr Ave Unit P-2D, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • Built 1974

  3045 Aaron Burr Ave Unit P-2D, Winter Park, FL 32792

  Last Sold Summary

  • $118/SF
  • 26 Days On Market

  • Last Sold Price $125,000
  • Apr 21, 2025

  Last Listing Agent Leyder Salamanca FLORIDA REALTY INVESTMENTS

Showing Results 201 - 240, Page 6 of 18