Winter Park, FL Homes

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  /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

  

  Robert Cozzone

  KOKOMO REALTY LLC

  (321) 467-7900

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

  

  Gwendolen Flynn

  COLDWELL BANKER RESIDENTIAL RE

  (321) 334-2867

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

  

  Carmen Vazquez

  REALTY TECH INC

  (321) 339-0107

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

  

  Julie Boyd-Elrod

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 483-3150

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

  

  Freddie Crespo

  INVESTOR'S REAL ESTATE LLC

  (321) 490-4832

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