28,315

Winter Park, FL Homes

Section Image Section Image
  • /34

    $249,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,020 Sq Ft

    2432 Barbados Dr, Winter Park, FL 32792

    Under contract-accepting backup offers. *ACCEPTING BACKUP OFFERS* Welcome to 2432 Barbados Dr, Winter Park! This beautifully updated 2-bedroom, 2-bath home that delivers the perfect blend of comfort, privacy, and that easy Florida lifestyle. From the moment you arrive, you’ll appreciate the peace of mind that comes with a BRAND NEW roof, along with a layout that feels both functional and

    Agent Photo

    Robert Cozzone

    KOKOMO REALTY LLC

    (321) 467-7900

    2432 Barbados Dr, Winter Park, FL 32792
  • /53

    $1,683 - $9,184 per month

    Juno Winter Park

    Studio - 3 Beds

    1305 Morgan Stanley Ave, Winter Park, FL 32789

    Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,

    1305 Morgan Stanley Ave, Winter Park, FL 32789
  • /2

    $374,900 Sold Oct 10, 2025

    2028 Leanne Ct, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,539 Sq Ft
    • Built 1968

    Last Sold Summary

    • $244/SF
    • 9 Days On Market

    Last Listing Agent Jamie Ampel ALL SELLERS & BUYERS REALTY INC

    2028 Leanne Ct, Winter Park, FL 32792
    • /2

      Est $1,169,273 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,871 Sq Ft

      363 N Phelps Ave, Winter Park, FL 32789

      363 N Phelps Ave, Winter Park, FL 32789
  • /8

    $260,000

    • Land
    • 0.81 Acre
    • $320,988 per Acre

    3580 Wilde Ave, Winter Park, FL 32792

    Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just shy of an acre, lot in coveted Winter Park. Nestled on a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level lot on a

    Agent Photo

    Gwendolen Flynn

    COLDWELL BANKER RESIDENTIAL RE

    (321) 334-2867

    3580 Wilde Ave, Winter Park, FL 32792
  • /25

    $6,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,354 Sq Ft
    • Condo for Rent

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

    Welcome to this charming condominium in Winter Park! This home features a spacious living area with ample natural light, a modern kitchen with sleek appliances, and large bedrooms. Enjoy the convenience of nearby shopping, dining, and entertainment. The community provides well-maintained amenities for residents to enjoy. With its prime location, this condo provides easy access to all that the

    Steven Koleno BEYCOME OF FLORIDA LLC

    782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789
  • /2

    $750,000 Sold Jun 09, 2025

    2756 Summerfield Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft
    • Built 1967

    Last Sold Summary

    • 3% Above List Price
    • $431/SF
    • 4 Days On Market

    Current Estimated Value $737,298

    Last Listing Agent Alexis Davis FANNIE HILLMAN & ASSOCIATES

    2756 Summerfield Rd, Winter Park, FL 32792
    • /2

      Est $700,271 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,940 Sq Ft

      678 Depugh St, Winter Park, FL 32789

      678 Depugh St, Winter Park, FL 32789
  • /19

    $225,000

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

    7706 Country Place Unit A8, Winter Park, FL 32792

    Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining

    Agent Photo

    Carmen Vazquez

    REALTY TECH INC

    (321) 339-0107

    7706 Country Place Unit A8, Winter Park, FL 32792
  • /103

    $1,991 - $6,413 per month

    Paseo at Winter Park Village

    1 - 3 Beds

    940 W Canton Ave, Winter Park, FL 32789

    Ready for an apartment home that truly feels like home? With upscale finishes and modern amenities, Paseo's units are ready to welcome you. You (and your pet!) can relax in our palm-lined courtyard, lounge by the pool, or play in our on-site dog park. With the shopping of Winter Park Village, movies at the Regal Cinema, and the historic downtown all close by, there are endless opportunities to

    940 W Canton Ave, Winter Park, FL 32789
  • /2

    $2,295,000 Sold Dec 16, 2025

    1661 Palm Ave, Winter Park, FL 32789

    • 4 Beds
    • 6 Baths
    • 3,570 Sq Ft
    • Built 2025

    Last Sold Summary

    • 12% Below List Price
    • $643/SF
    • 26 Days On Market

    Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

    1661 Palm Ave, Winter Park, FL 32789
    • /2

      Est $818,970 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,861 Sq Ft

      439 N Capen Ave, Winter Park, FL 32789

      439 N Capen Ave, Winter Park, FL 32789
  • /31

    $359,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft

    1690 Viburnum Ln, Winter Park, FL 32792

    Under contract-accepting backup offers. Welcome to 1690 Viburnum Lane, a classy, 3 Bed, 2 Bath home in the heart of Winter Park! *NEW* Roof (2024), Driveway (2025), Water Heater (2026), HVAC & Double-Pane Windows (2019)! The spacious & open layout is highlighted by the large windows allowing natural light to flood in the living room area through to the kitchen. The kitchen features ample storage

    Agent Photo

    Julie Boyd-Elrod

    CHARLES RUTENBERG REALTY ORLANDO

    (321) 483-3150

    1690 Viburnum Ln, Winter Park, FL 32792
  • /20

    $2,600 per month

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Townhouse for Rent

    2344 Flamingo Way, Winter Park, FL 32792

    Discover 2344 Flamingo Way in Winter Park, FL. This well maintained townhome offers comfort and convenience in a prime location. The home features 1,536 square feet with three bedrooms and two bathrooms. The layout includes a living room, dining room, dinette, and a modern kitchen. The kitchen offers a tile backsplash, decorative countertops, and stainless steel appliances including a flat

    Rodrigo Marsal LIFESTYLE INTERNATIONAL REALTY

    2344 Flamingo Way, Winter Park, FL 32792
  • /2

    $2,700,000 Sold Oct 30, 2025

    1020 Mayfield Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,663 Sq Ft
    • Built 1989

    Last Sold Summary

    • 15% Below List Price
    • $1,014/SF
    • 149 Days On Market

    Current Estimated Value $2,662,282

    Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

    1020 Mayfield Ave, Winter Park, FL 32789
    • /2

      Est $483,012 Not Listed For Sale

      • 1 Bed

      2313 Loch Lomond Dr, Winter Park, FL 32792

      2313 Loch Lomond Dr, Winter Park, FL 32792
  • /51

    $1,489,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,459 Sq Ft

    102 Bell Place, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Dreams Do Come True! This spectacular brand-new 2025 block construction home, crafted with steel framing instead of wood, combines modern luxury with timeless design in one of Winter Park’s up incoming desirable areas—just moments from Interlachen Country Club and the Lakemont Heights neighborhood an NO HOA!Step through the double-door entry

    Agent Photo

    Freddie Crespo

    INVESTOR'S REAL ESTATE LLC

    (321) 490-4832

    102 Bell Place, Winter Park, FL 32792
  • /37

    $1,210 - $1,823 per month

    Seabrook

    1 - 2 Beds

    3114 Terry Brook Dr, Winter Park, FL 32792

    The Seabrook Apartment community is located near the 408 Expressway, close to shopping and dining areas 1/4 mile away, just minutes away from the downtown areas of Orlando and Winter Park. Several renowned schools such as Brookshire Elementary, Glenridge Middle School and Winter Park High School are nearby as well. We offer spacious one and two-bedroom apartments. All of our homes have been

    3114 Terry Brook Dr, Winter Park, FL 32792
  • /89

    $830,000 Sold Mar 11, 2025

    1223 Formosa Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 3,834 Sq Ft
    • Built 1940

    Last Sold Summary

    • 31% Below List Price
    • $216/SF
    • 240 Days On Market

    Current Estimated Value $857,873

    Last Listing Agent Farah Bloom KELLER WILLIAMS WINTER PARK

    1223 Formosa Ave, Winter Park, FL 32789
    • /2

      Est $2,297,669 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,467 Sq Ft

      2172 Temple Dr, Winter Park, FL 32789

      2172 Temple Dr, Winter Park, FL 32789
  • /26

    $439,900 Pending

    • 3 Beds
    • 3 Baths
    • 1,880 Sq Ft

    2835 Bongart Rd, Winter Park, FL 32792

    Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Opportunities like this are rare. Perfectly suited for multi-generational living, mother-in-law suite potential, or rental income, this versatile POOL home sits on an oversized lot with no HOA in one of Central Florida’s most desirable locations — Winter Park.The flexible floor plan allows for comfortable

    Irina Paul FUTURE HOME REALTY INC

    2835 Bongart Rd, Winter Park, FL 32792
  • /27

    $2,450 per month

    • 2 Beds
    • 2 Baths
    • 1,050 Sq Ft
    • Townhouse for Rent

    1256 Michigan Ave, Winter Park, FL 32789

    Completely renovated. Beautiful two bedrooms, two baths with laundry room and private fenced backyard and carport. Close to upscale restaurants and shopping, and Interstate 4. This beautiful property is between Winter Park and downtown Orlando.

    Farah Novin PREMIER SOTHEBY'S INTL. REALTY

    1256 Michigan Ave, Winter Park, FL 32789
  • /2

    $4,100,000 Sold Apr 18, 2025

    1691 Chestnut Ave, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 4,582 Sq Ft
    • Built 2024

    Last Sold Summary

    • 15% Below List Price
    • $895/SF
    • 1 Day On Market

    Current Estimated Value $3,851,500

    Last Listing Agent Sue Silberbusch COMPASS FLORIDA LLC

    1691 Chestnut Ave, Winter Park, FL 32789
    • /2

      Est $438,692 Not Listed For Sale

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

      3092 Nicholson Dr, Winter Park, FL 32792

      3092 Nicholson Dr, Winter Park, FL 32792
  • /54

    $439,900

    • 3 Beds
    • 2 Baths
    • 2,083 Sq Ft

    1367 Tierra Cir, Winter Park, FL 32792

    Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers Spanish architectural combined with thoughtful modern improvements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with updated landscaping, the property offers

    Brian Bauer SOUTHERN LAND & HOMES

    1367 Tierra Cir, Winter Park, FL 32792
  • /74

    $1,610 - $5,139 per month

    Vintage Winter Park Apartments

    1 - 3 Beds

    7490 Dwell Well Way, Winter Park, FL 32792

    Dwell well with us. Welcome to quintessential Vintage Winter Park, a residential community featuring One, Two & Three bedroom apartments in Winter Park, FL. Spacious layouts and amenities welcome you home, along with exceptional service and an ideal location within walking distance to shopping, dining and entertainment options.

    7490 Dwell Well Way, Winter Park, FL 32792
  • /2

    $3,900,000 Sold Feb 18, 2025

    1341 College Point, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 4,279 Sq Ft
    • Built 2005

    Last Sold Summary

    • 8% Below List Price
    • $911/SF
    • 66 Days On Market

    Current Estimated Value $3,831,882

    Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

    1341 College Point, Winter Park, FL 32789
    • /2

      Est $418,331 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,346 Sq Ft

      5201 Lake Howell Rd, Winter Park, FL 32792

      5201 Lake Howell Rd, Winter Park, FL 32792
  • /35

    $200,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft

    623 Saint Johns Ct Unit 623, Winter Park, FL 32792

    If you’re searching for a place that feels like home the moment you walk in—not just another condo—this one might be exactly what you’ve been looking for. Nearby to Full Sail University, UCF, restaurants, shopping, entertainment, and major road access, this property is in a prime location. Step through the covered front porch and into a bright, welcoming space with soaring vaulted ceilings, new

    David Dorman CENTURY 21 CARIOTI

    623 Saint Johns Ct Unit 623, Winter Park, FL 32792
  • /21

    $2,375 per month

    • 3 Beds
    • 2 Baths
    • 1,238 Sq Ft
    • House for Rent

    1812 Pineview Cir, Winter Park, FL 32792

    WOW!! Renovated to perfection. Recently painted inside and out and a newer kitchen featuring white shaker cabinets with quartz countertops plus new appliances make this home a great find in an amazing location. This adorable and spotless Winter Park charmer is nestled on a quiet street a stone's throw to Lakemont Elementary. Tile and laminate throughout makes this home easy breezy to maintain.

    Sherrie Pillat RE/MAX ASSURED

    1812 Pineview Cir, Winter Park, FL 32792
  • /2

    $638,250 Sold Sep 02, 2025

    1536 Golfside Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,888 Sq Ft
    • Built 1980

    Last Sold Summary

    • $338/SF
    • 3 Days On Market

    Current Estimated Value $639,424

    Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

    1536 Golfside Dr, Winter Park, FL 32792
    • /2

      Est $349,081 Not Listed For Sale

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

      5229 N Woodcrest Dr, Winter Park, FL 32792

      5229 N Woodcrest Dr, Winter Park, FL 32792
  • /40

    $899,000 Pending

    • 5 Beds
    • 2 Baths
    • 2,554 Sq Ft

    2609 Summerfield Rd, Winter Park, FL 32792

    Under contract-accepting backup offers. Luxury living meets the fairways in this exceptional 5/2, 2554 sqft. retreat, perfectly positioned across from the Winter Park Pines Golf Course and its vibrant clubhouse for dining and drinks. Professionally designed from top to bottom, this sun-filled home blends timeless elegance with modern peace of mind—every detail thoughtfully upgraded, every space

    Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

    2609 Summerfield Rd, Winter Park, FL 32792
  • /51

    $1,311 - $2,085 per month

    Cranes Landing Apartments

    1 - 3 Beds

    3440 N Goldenrod Rd, Winter Park, FL 32792

    Experience the perfect blend of comfort and convenience at Cranes Landing Apartments in Winter Park, Florida. Our beautifully designed one-, two-, and three-bedroom apartment homes feature open-concept layouts, modern finishes, and premium appliances to complement your lifestyle.Enjoy a community that’s built around connection and comfort. Relax by the resort-style pool, challenge friends

    3440 N Goldenrod Rd, Winter Park, FL 32792
  • /2

    $401,000 Sold Oct 15, 2025

    1809 Palmer Ave, Winter Park, FL 32792

    • Land
    • 0.21 Acre
    • $1,909,524 per Acre

    Last Sold Summary

    • 5 Days On Market

    Current Estimated Value $390,328

    Last Listing Agent Christina Munkberg COLDWELL BANKER RESIDENTIAL RE

    1809 Palmer Ave, Winter Park, FL 32792
    • /2

      Est $305,235 Not Listed For Sale

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

      2327 Antilles Dr, Winter Park, FL 32792

      2327 Antilles Dr, Winter Park, FL 32792
  • /34

    $579,999

    • 3 Beds
    • 2 Baths
    • 1,570 Sq Ft

    330 Elkhorn Ct, Winter Park, FL 32792

    330 Elkhorn Ct is a beautifully renovated, move-in-ready home located in the highly desired Winter Park Pines community. Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette that feels clean and inviting. The kitchen has been thoughtfully updated with shaker-style cabinetry, sleek countertops, stainless steel appliances, and

    Neil Chetram LA ROSA REALTY CW PROPERTIES L

    330 Elkhorn Ct, Winter Park, FL 32792
  • /28

    $1,750 per month

    • 2 Beds
    • 2 Baths
    • 1,058 Sq Ft
    • Condo for Rent

    4858 Tangerine Ave Unit 4858, Winter Park, FL 32792

    Renovated ONE story condo available in Wrenwood. Light and Bright 2 BEDROOM, 2 BATH unit features neutral tile and LVT flooring (no carpet), Quartz counters, Stainless Steel appliances, Full size all-in-one WASHER/DRYER. Freshly Painted with UPDATES throughout- ready for occupancy! Generously sized bedrooms with ample closet space; Sliding doors from living room lead to a private Screened-in

    Emily Lemieux RE/MAX TOWN & COUNTRY REALTY

    4858 Tangerine Ave Unit 4858, Winter Park, FL 32792
  • /2

    $775,000 Sold May 21, 2025

    1818 Mondrian Cir, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 2,265 Sq Ft
    • Built 2018

    Last Sold Summary

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

    Current Estimated Value $806,281

    Last Listing Agent Brian Teach COLDWELL BANKER RESIDENTIAL RE

    1818 Mondrian Cir, Winter Park, FL 32789
    • /2

      Est $542,217 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,040 Sq Ft

      1981 Japonica Rd, Winter Park, FL 32792

      1981 Japonica Rd, Winter Park, FL 32792

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home