28,400

Winter Park, FL Homes

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  • /20

    $335,000

    • 3 Beds
    • 2.5 Baths
    • 1,682 Sq Ft

    1540 Florentino Ln, Winter Park, FL 32792

    Come and see your new home in the sought after Vistas at Howell Branch community. This two story townhouse has 3 bedrooms, 2.5 baths, and open first floor, floor plan. Relax in the evening on your screened in porch. The master bedroom has a walk in closet and large master bath. Your washer and dryer are on the second floor centrally located to all the bedrooms. You will find yourself within

    Ashley Fisak COLDWELL BANKER REALTY

    1540 Florentino Ln, Winter Park, FL 32792
  • /12

    $6,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Apartment for Rent

    301 W Comstock Ave, Winter Park, FL 32789

    Under Construction. Beautiful 2 bedroom, 2.5 bath, laundry in unit, detached two (2) car garage with private guest suite located in Hannibal Square. New Construction.

    Sydney Brownlee THE SYDGAN CORP

    301 W Comstock Ave, Winter Park, FL 32789
  • /2

    $199,900

    Sold Nov 03, 2025

    2500 Lee Rd Unit 134, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft
    • Built 1969

    Last Sold Summary

    • 5% Below List Price
    • $310/SF
    • 130 Days On Market

    Current Estimated Value $192,989

    Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

    2500 Lee Rd Unit 134, Winter Park, FL 32789
    • /2

      Est $1,358,078

      Not Listed For Sale

      1830 Pineview Cir, Winter Park, FL 32792

      • 4 Beds
      • 3.5 Baths
      • 2,843 Sq Ft
      • Built 2024
      1830 Pineview Cir, Winter Park, FL 32792

      Last Sold Summary

      • 57 Days On Market

  • /32

    $775,000

    $25K PRICE DROP Pending
    • 4 Beds
    • 3.5 Baths
    • 3,062 Sq Ft

    675 Overspin Dr, Winter Park, FL 32789

    Seller may consider buyer concessions if made in an offer ~ Beautiful upgrades, a versatile layout, and the best of Winter Park at your doorstep! With Dubsdread Golf Course just around the corner and Fairbanks Avenue minutes away, this 4-bedroom, 3.5-bath CUSTOM BUILT HOME puts you in the center of it all – NO HOA required! Major systems have been well maintained; including a NEW A/C UNIT with UV

    Jennifer Wemert WEMERT GROUP REALTY LLC

    675 Overspin Dr, Winter Park, FL 32789
  • /14

    $1,750 Per Month

    • 2 Beds
    • 1 Bath
    • 854 Sq Ft
    • House for Rent

    2304 Inagua Way, Winter Park, FL 32792

    Welcome to this charming 2 bedroom, 1 bathroom corner unit in Winter Park, FL. This single-story home features ceramic tile flooring throughout, perfect for easy maintenance. The freshly painted interior complements the renovated kitchen and bathroom, giving the space a modern and updated feel. Enjoy the privacy of the fenced backyard, ideal for outdoor entertaining or relaxing. Located in the

    2304 Inagua Way, Winter Park, FL 32792
  • /2

    $340,000

    Sold Feb 26, 2026

    7580 Aloma Pines Ct, Winter Park, FL 32792

    • 3 Beds
    • 3.5 Baths
    • 1,872 Sq Ft
    • Built 2016

    Last Sold Summary

    • 7% Below List Price
    • $182/SF
    • 94 Days On Market

    Current Estimated Value $347,480

    Last Listing Agent Simon Colak USCO CAPITAL GROUP

    7580 Aloma Pines Ct, Winter Park, FL 32792
    • /2

      Not Listed For Sale

      255 Sandlewood Trail, Winter Park, FL 32789

      • 2 Beds
      • 2.5 Baths
      • 960 Sq Ft
      • Built 1984
      255 Sandlewood Trail, Winter Park, FL 32789

      Last Sold Summary

      • 24 Days On Market

  • /14

    $399,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,363 Sq Ft

    2142 Blossom Ln, Winter Park, FL 32789

    Under contract-accepting backup offers. Exceptional opportunity to build new in one of Winter Park’s most desirable and established areas on the north shore of Lake Killarney. Situated on a spacious 0.34-acre lot, this property offers over one-third of an acre—providing ample room to design and construct a substantial custom home in a neighborhood known for its longtime charm, mature

    Billy Wygle THE WILKINS WAY LLC

    2142 Blossom Ln, Winter Park, FL 32789
  • /16

    $1,800 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,151 Sq Ft
    • Townhouse for Rent

    7420 Woodburn Ct Unit 25, Winter Park, FL 32792

    Corner lot 3 bedrooms and 2.5 bathroom, 2 assigned parking spaces. NEW 3 bathrooms kitchen, washer dryer and stove and new AC. No carpet only wood floor. Near to Costco and highway.

    He Gao U S GLORY REALTY

    7420 Woodburn Ct Unit 25, Winter Park, FL 32792
  • /2

    $250,000

    Sold Apr 10, 2026

    1823 Maywood Rd, Winter Park, FL 32792

    • 3 Beds
    • 1.5 Baths
    • 1,232 Sq Ft
    • Built 1956

    Last Sold Summary

    • $203/SF
    • 1 Day On Market

    Current Estimated Value $237,520

    Last Listing Agent Abby Nelson RE/MAX 200 REALTY

    1823 Maywood Rd, Winter Park, FL 32792
    • /2

      Est $864,520

      Not Listed For Sale

      1919 S Lakemont Ave, Winter Park, FL 32792

      • 3 Beds
      • 3.5 Baths
      • 2,085 Sq Ft
      • Built 2024
      1919 S Lakemont Ave, Winter Park, FL 32792

      Last Sold Summary

      • 282 Days On Market

  • /38

    $280,000

    $5K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    5143 Lazy Oaks Dr, Winter Park, FL 32792

    Quiet Living in the Desirable Lazy Oaks Community of Winter Park. Welcome to the peaceful, well-established community of Lazy Oaks in highly sought-after Winter Park. This hidden gem offers beautifully landscaped grounds, meticulous maintenance, and the added benefit of a low HOA.This lovingly maintained 2-bedroom, 2-bath home features a spacious, thoughtfully designed floor plan with an

    Mindy Machock KELLER WILLIAMS REALTY AT THE PARKS

    5143 Lazy Oaks Dr, Winter Park, FL 32792
  • /16

    $1,600 Per Month

    • 2 Beds
    • 2 Baths
    • 964 Sq Ft
    • Condo for Rent

    3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792

    3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792
  • /2

    $266,000

    Sold Nov 19, 2025

    1500 Gay Rd Unit 9B, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft
    • Built 1972

    Last Sold Summary

    • 1% Below List Price
    • $259/SF
    • 5 Days On Market

    Current Estimated Value $258,285

    Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

    1500 Gay Rd Unit 9B, Winter Park, FL 32789
    • /2

      Est $196,794

      Not Listed For Sale

      3251 Forest Oaks Ct Unit 115, Winter Park, FL 32792

      • 2 Beds
      • 2.5 Baths
      • 1,031 Sq Ft
      • Built 1983
      3251 Forest Oaks Ct Unit 115, Winter Park, FL 32792

      Last Sold Summary

      • 13 Days On Market

  • /31

    $429,000

    Open Sat 10AM - 1PM
    • 4 Beds
    • 2 Baths
    • 1,836 Sq Ft

    1842 Puritan Ave, Winter Park, FL 32792

    Modern design , open concept layout , sleek quartz counter top , all new appliances, new luxury vinyl plank flooring, new lanai upgrade. This beautiful 4 bedroom and 2 full bath is situated on a 8,250 square feet lot, which was newly fenced in 2024 which gives a sense of privacy and spaciousness. As you exit the interior through the French door into the lanai . There is two detached shed for your

    Karan Jodha MOBED REALTY, P.A

    1842 Puritan Ave, Winter Park, FL 32792
  • /16

    $1,695 Per Month

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Condo for Rent

    620 Trinidad Ct Unit 620, Winter Park, FL 32792

    Beautifully Renovated 2-Bedroom Home in Desirable Winter Park! Welcome to this charming newly renovated 2-bedroom, 2-bath home located in the highly desirable Winter Park area. Featuring modern upgrades and a warm, inviting layout, this home offers the perfect blend of comfort and style. Enjoy ceramic tile flooring throughout the first floor, brand-new carpet in the upstairs bedroom, and a

    Jacob Hara TRANSCEND REALTY

    620 Trinidad Ct Unit 620, Winter Park, FL 32792
  • /2

    $470,000

    Sold Jan 15, 2026

    3319 Ellwood Ct, Winter Park, FL 32792

    • 5 Beds
    • 3 Baths
    • 1,546 Sq Ft
    • Built 1968

    Last Sold Summary

    • 2% Above List Price
    • $304/SF
    • 78 Days On Market

    Current Estimated Value $466,322

    Last Listing Agent Elena Sanchez BALDWIN PARK REALTY LLC

    3319 Ellwood Ct, Winter Park, FL 32792
    • /55

      Est $945,820

      Not Listed For Sale

      1484 Via Sangro Place, Winter Park, FL 32792

      • 4 Beds
      • 3 Baths
      • 3,063 Sq Ft
      • Built 2015
      1484 Via Sangro Place, Winter Park, FL 32792

      Last Sold Summary

      • 5 Days On Market

  • /53

    $2,225,000

    Open Sun 2PM - 4PM $70K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,691 Sq Ft

    1885 Temple Dr, Winter Park, FL 32789

    Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most sought-after neighborhoods adjacent to the Vias, Winter Park Racquet Club and Dommerich

    Jennifer Sloan COMPASS FLORIDA LLC

    1885 Temple Dr, Winter Park, FL 32789
  • /22

    $1,450 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    151 N Orlando Ave, Winter Park, FL 32789

    Discover comfortable living in this charming 1-bedroom, 1-bathroom residential condo at 151 N Orlando Ave, Winter Park, FL. Spanning 600 sq ft, this unit features modern hardwood flooring, large closets, and a private patio perfect for relaxing or entertaining. The kitchen is equipped with a range and refrigerator, complemented by air conditioning for year-round comfort. Water and trash services

    151 N Orlando Ave, Winter Park, FL 32789
  • /2

    $245,900

    Sold Aug 11, 2025

    195 Sandlewood Trail Unit 2, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 1,132 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Below List Price
    • $217/SF
    • 2 Days On Market

    Current Estimated Value $251,521

    Last Listing Agent Matt Merdian MERDIAN REALTY LLC

    195 Sandlewood Trail Unit 2, Winter Park, FL 32789
    • /2

      Est $824,236

      Not Listed For Sale

      1776 Mondrian Cir, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 2,193 Sq Ft
      • Built 2022
      1776 Mondrian Cir, Winter Park, FL 32789

      Last Sold Summary

      • 88 Days On Market

  • /44

    $625,000

    Open Fri 5PM - 7PM
    • 5 Beds
    • 2 Baths
    • 1,938 Sq Ft

    2652 Abbey Rd, Winter Park, FL 32792

    Welcome to 2652 Abbey Road, a beautifully renovated home tucked away on a quiet cul-de-sac in the highly desirable Winter Park Estates community. Situated on a spacious corner lot, this stunning 4-bedroom, 2-bath residence with a dedicated office offers the perfect blend of modern design, functionality, and location. From the moment you step inside, you'll appreciate the open-concept floor plan

    Mario Zendeli COMPASS FLORIDA LLC

    2652 Abbey Rd, Winter Park, FL 32792
  • /27

    $3,400 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,219 Sq Ft
    • House for Rent

    7864 Broken Arrow Trail, Winter Park, FL 32792

    Fabulous rental opportunity in the sought-after Winter Park School District. This 4-bedroom, 2.5-bath, 2219-square-foot home also boasts glorious lake views from the massive 1,000-square-foot Florida room, ideal for entertaining and enjoying the Florida lifestyle on an expansive 1⁄2 acre lot. Ready for move-in, the home is full of natural light pouring in and shining onto the wood flooring

    Julia Magnani LOKATION

    7864 Broken Arrow Trail, Winter Park, FL 32792
  • /2

    $165,000

    Sold Jun 01, 2026

    200 Saint Andrews Blvd Unit 315, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 793 Sq Ft
    • Built 1970

    Last Sold Summary

    • 6% Below List Price
    • $208/SF
    • 77 Days On Market

    Current Estimated Value $165,396

    Last Listing Agent Eric Zimmerman RE/MAX ADVANTAGE

    200 Saint Andrews Blvd Unit 315, Winter Park, FL 32792
    • /2

      Est $716,556

      Not Listed For Sale

      1806 Mondrian Cir, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 2,016 Sq Ft
      • Built 2018
      1806 Mondrian Cir, Winter Park, FL 32789

      Last Sold Summary

      • 61 Days On Market

  • /25

    $209,900

    $10K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,058 Sq Ft

    4858 Tangerine Ave Unit 4858, Winter Park, FL 32792

    Under contract-accepting backup offers. 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

    Angelica Diaz Bajo WRA BUSINESS & REAL ESTATE

    4858 Tangerine Ave Unit 4858, Winter Park, FL 32792
  • /26

    $2,350 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,482 Sq Ft
    • Beautiful 3 bedroom 2.5 bath home with vaulted ceilings and 2 car garage

    3449 Allston Ln, Winter Park, FL 32792

    Come check out this gorgeous Winter Park home with a BRAND NEW ROOF! Home has 3 walk-in closets and vaulted ceilings throughout. Enjoy the large eat-in kitchen with plenty of cabinet space for all of your home cooked meals. The living room is spacious with room for a formal dining room or office. Home features the main floor master and laundry with two additional bedrooms upstairs. You will

    3449 Allston Ln, Winter Park, FL 32792
  • /2

    $1,300,000

    Sold Sep 22, 2025

    1371 Lyndale Blvd, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,714 Sq Ft
    • Built 1949

    Last Sold Summary

    • 4% Below List Price
    • $479/SF
    • 8 Days On Market

    Current Estimated Value $1,287,836

    Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

    1371 Lyndale Blvd, Winter Park, FL 32789
    • /2

      Not Listed For Sale

      663 Trinidad Ct Unit S, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 1981
      663 Trinidad Ct Unit S, Winter Park, FL 32792

      Last Sold Summary

      • 164 Days On Market

  • /29

    $429,000

    $31K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,405 Sq Ft

    2779 Sanbina St, Winter Park, FL 32789

    Under contract-accepting backup offers. Rare opportunity in the heart of 32789 — priced under $500K, this 3-bedroom, 2-bathroom Winter Park home delivers the location, lot, and bones that buyers in this zip code rarely find at this price point. Zoned for Dommerich Elementary and Winter Park High School and situated on a generous 0.23-acre lot, this is the one worth moving quickly on. Upon entry,

    Caroline Fiore MAINFRAME REAL ESTATE

    2779 Sanbina St, Winter Park, FL 32789
  • /17

    $1,300 Per Month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit D213, Winter Park, FL 32789

    Adorable and cozy second floor condo, conveniently located off Lee Road in Orlando, minutes from SR I-4. This 2-bedroom 1 full bath condo is located in the quiet community or Waterfall Cove. Water is included with a community pool and playground for tenants to enjoy. Open floor plan with carpet and laminate in kitchen and bath. Fresh paint throughout. Balcony just outside the sliders in living

    Rachel DeCamp RLL Real Estate Group

    1695 Lee Rd Unit D213, Winter Park, FL 32789
  • /2

    $405,000

    Sold Jan 09, 2026

    3425 Ferndell Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,516 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $267/SF
    • 164 Days On Market

    Current Estimated Value $401,545

    Last Listing Agent Ivanhoe Alvarez LOKATION

    3425 Ferndell Dr, Winter Park, FL 32792
    • /2

      Est $176,082

      Not Listed For Sale

      3208 Oak Lawn Place Unit 218, Winter Park, FL 32792

      • 2 Beds
      • 2.5 Baths
      • 1,031 Sq Ft
      • Built 1984
      3208 Oak Lawn Place Unit 218, Winter Park, FL 32792

      Last Sold Summary

      • 53 Days On Market

  • /36

    $405,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,533 Sq Ft

    3440 Allston Ln, Winter Park, FL 32792

    Exceptional Single-Family Home in Winter Park, FLThis beautifully maintained 3-bedroom, 2.5-bathroom residence offers an impressive open floor plan with elegant laminate flooring throughout, updated just two years ago. The renovated kitchen (2019) features granite countertops and comes fully equipped with all appliances. Major capital improvements include a new roof (2019) and a new HVAC

    Hugo Hernandez EXIT GLOBAL REALTY

    3440 Allston Ln, Winter Park, FL 32792
  • /26

    $1,950 Per Month

    • 3 Beds
    • 2.5 Baths
    • Townhouse for Rent

    7454 Wynnewood Square, Winter Park, FL 32792

    3 Bedroom 2.5 Bath Townhome located in Winter Park. Washer/Dryer Connections and Plenty of Storage inside and out! No Pets Allowed!

    7454 Wynnewood Square, Winter Park, FL 32792
  • /2

    $235,000

    Sold Jan 29, 2026

    613 Orange Tree Ct Unit 507, Maitland, FL 32751

    • 3 Beds
    • 2 Baths
    • 1,256 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Below List Price
    • $187/SF
    • 10 Days On Market

    Current Estimated Value $234,369

    Last Listing Agent Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

    613 Orange Tree Ct Unit 507, Maitland, FL 32751
    • /2

      Est $1,210,535

      Not Listed For Sale

      2726 Lake Howell Ln, Winter Park, FL 32792

      • 3 Beds
      • Built 1960
      2726 Lake Howell Ln, Winter Park, FL 32792

      Last Sold Summary

      • 49 Days On Market

Showing Results 281 - 320, Page 8 of 18

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