28,231

Winter Park, FL Homes

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  • /59

    $2,195,000

    $100K 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
  • /46

    $2,800 Per Month

    • 4 Beds
    • 3 Baths
    • 1,835 Sq Ft
    • House for Rent

    2719 Merrie Oaks Rd, Winter Park, FL 32792

    Welcome to this 4-bedroom, 3-bathroom home nestled in the desirable Winter Park Pines area of Winter Park. This spacious residence features a well-equipped kitchen complete with all major appliances and an abundance of cabinet space, making it perfect for any home chef. The inviting den and family room serve as the heart of the home, featuring a cozy fireplace ideal for relaxing evenings. The

    2719 Merrie Oaks Rd, Winter Park, FL 32792
  • /2

    $145,000

    Sold Apr 23, 2026

    2500 Lee Rd Unit 243, Winter Park, FL 32789

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

    Last Sold Summary

    • 28% Below List Price
    • $225/SF
    • 286 Days On Market

    Current Estimated Value $145,972

    Last Listing Agent Sue Gilman KELLER WILLIAMS WINTER PARK

    2500 Lee Rd Unit 243, Winter Park, FL 32789
    • /2

      Est $1,441,948

      Not Listed For Sale

      1077 Minnesota Ave, Winter Park, FL 32789

      • 4 Beds
      • 4 Baths
      • 3,046 Sq Ft
      • Built 2025
      1077 Minnesota Ave, Winter Park, FL 32789

      Last Sold Summary

      • 75 Days On Market

      Last Listing Agent Jake Johnson SHORES REAL ESTATE

  • /31

    $669,000

    $15K PRICE DROP Under Contract
    • 4 Beds
    • 2 Baths
    • 1,605 Sq Ft

    2833 Prince John Rd, Winter Park, FL 32792

    Under contract-accepting backup offers. Virtually Staged. Welcome to a residence where timeless design meets modern sophistication in the highly sought-after Winter Park Pines community—one of Winter Park's most established neighborhoods, celebrated for its tree-lined streets, oversized homesites, exceptional schools, and proximity to world-class dining, shopping, golf, and cultural attractions.

    Wendy Aldana LLC NETWORTH REALTY OF ORLANDO, LLC

    2833 Prince John Rd, Winter Park, FL 32792
  • /18

    $1,600 Per Month

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

    3651 N Goldenrod Rd Unit 103, Winter Park, FL 32792

    2-bedroom, 2-bathroom first-floor unit with an open floor plan to the kitchen, living /dining area and breakfast bar. This lovely home includes newer Whirlpool stainless appliances, including Refrigerator, Microwave, cook top Range/oven, and Dishwasher. A washer and Dryer in the unit is included also. Steps from the community pool/clubhouse. Excellent school zone which includes desirable Winter

    Youree Lundy KELLER WILLIAMS ADVANTAGE III

    3651 N Goldenrod Rd Unit 103, Winter Park, FL 32792
  • /2

    $850,000

    Sold Mar 31, 2026

    1929 S Lakemont Ave, Winter Park, FL 32792

    • 3 Beds
    • 3.5 Baths
    • 2,160 Sq Ft
    • Built 2023

    Last Sold Summary

    • 10% Below List Price
    • $394/SF
    • 91 Days On Market

    Current Estimated Value $875,647

    Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

    1929 S Lakemont Ave, Winter Park, FL 32792
    • /2

      Est $712,298

      Not Listed For Sale

      1151 Wildmeadow Run, Winter Park, FL 32792

      • 4 Beds
      • 2.5 Baths
      • 2,196 Sq Ft
      • Built 2020
      1151 Wildmeadow Run, Winter Park, FL 32792

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

  • /59

    $1,999,990

    New Construction $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,330 Sq Ft

    525 S Lakemont Ave, Winter Park, FL 32792

    Thoughtfully designed with an uncompromising commitment to quality, craftsmanship, and detail, this exceptional new construction residence is an expression of luxury living. Defined by its striking architecture and refined contemporary design, the home makes an unforgettable first impression with a dramatic two-story foyer featuring soaring ceilings, a statement staircase with custom millwork,

    Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    525 S Lakemont Ave, Winter Park, FL 32792
  • /30

    $1,600 Per Month

    • 2 Beds
    • 2 Baths
    • 1,018 Sq Ft
    • House for Rent

    2911 Antique Oaks Cir, Winter Park, FL 32792

    Beautiful Vintage Condo Home For Rent! 2 Bed 2 Bath ( AVAILABLE MOVE IN NOW! )Come View This Amazing 2 Bed 2 Full Bath Condo home for Rent in Orlando, FL! - HOME SWEET HOME!Welcome home to this spacious 2 bed 2 Full bath home! Wood Flooring all through out the home great for entertaining family and friends. The Open kitchen highlights a beautiful open concept. There is also 2 Full

    2911 Antique Oaks Cir, Winter Park, FL 32792
  • /2

    $912,500

    Sold Jan 14, 2026

    210 Laurel Park Ct, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,838 Sq Ft
    • Built 2006

    Last Sold Summary

    • 4% Below List Price
    • $322/SF
    • 25 Days On Market

    Current Estimated Value $917,338

    Last Listing Agent Alireza Partovi EXP REALTY LLC

    210 Laurel Park Ct, Winter Park, FL 32792
    • /2

      Est $770,667

      Not Listed For Sale

      2320 Janice Ave, Winter Park, FL 32789

      2320 Janice Ave, Winter Park, FL 32789

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES

  • /34

    $639,000

    • 3 Beds
    • 2 Baths
    • 1,783 Sq Ft

    508 Brechin Dr, Winter Park, FL 32792

    Completely renovated and move-in ready, this beautifully updated Winter Park home offers a fresh, modern interior without the hassle of renovations. The brand-new kitchen features new cabinetry, quartz countertops and all new appliances, while both bathrooms have been fully renovated with new finishes and fixtures. New luxury vinyl plank flooring runs throughout the home, complemented by fresh

    Mary Lowen MTL REALTY LLC

    508 Brechin Dr, Winter Park, FL 32792
  • /2

    $2,495 Per Month

    • 2 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Condo for Rent

    720 Killarney Bay Ct, Winter Park, FL 32789

    LAKE KILLARNEY CONDO IN WINTER PARK! Enjoy the best of Winter Park living in this beautiful 2-bedroom, 2-bath corner condo in the private lakefront community of Killarney Bay. Featuring an open floor plan, stone and wood flooring, high ceilings, quartz kitchen countertops, stainless-steel appliances, generous storage, and a stunning stone-accented fireplace. Plus a utility room with a full size

    Lisa Gould KELLER WILLIAMS WINTER PARK

    720 Killarney Bay Ct, Winter Park, FL 32789
  • /2

    $335,000

    Sold Oct 31, 2025

    3525 Baxter Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1970

    Last Sold Summary

    • 14% Above List Price
    • $215/SF
    • 5 Days On Market

    Current Estimated Value $338,173

    Last Listing Agent Ashley Fisak COLDWELL BANKER REALTY

    3525 Baxter Dr, Winter Park, FL 32792
    • /2

      Est $263,164

      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

      • 12 Days On Market

      Last Listing Agent Kim Oliver NONA LEGACY POWERED BY LA ROSA

  • /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 COLDWELL BANKER REALTY

    3440 Allston Ln, Winter Park, FL 32792
  • /24

    $2,400 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,243 Sq Ft
    • Townhouse for Rent

    920 Aragon Ave, Winter Park, FL 32789

    Charming 2-Bedroom Townhouse in Prime Winter Park Location**Welcome to this beautifully maintained 2-bedroom, 2.5-bath townhouse with a one-car garage, ideally located in one of Winter Park\'s most sought-after neighborhoods. Just minutes from I-4, Orange Avenue, and downtown Winter Park, this home offers both convenience and comfort.This two-story residence features two spacious

    920 Aragon Ave, Winter Park, FL 32789
  • /2

    $715,000

    Sold Jun 12, 2026

    688 Brechin Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,599 Sq Ft
    • Built 1961

    Last Sold Summary

    • 1% Below List Price
    • $447/SF
    • 3 Days On Market

    Current Estimated Value $708,085

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

    688 Brechin 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

      • 26 Days On Market

      Last Listing Agent Leyder Salamanca FLORIDA REALTY INVESTMENTS

  • /42

    $299,000

    $15K PRICE INCREASE Pending
    • 3 Beds
    • 2 Baths
    • 1,235 Sq Ft

    2313 Knoll St, Winter Park, FL 32792

    Winter Park address with Seminole County taxes, and a new roof already in place from 2023. Three bedrooms, two baths, roughly 1,235 sf of living space in solid concrete block with central air. The 9,000 sf lot is fenced and shaded by mature oaks, and a 550 sf carport with workshop space. Flood Zone X, so no lender-required flood insurance. No HOA. No CDD. For an investor, the basis here pencils

    Terry Yonker BUCKEYE REALTY LLC

    2313 Knoll St, Winter Park, FL 32792
  • /21

    $1,400 Per Month

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

    1695 Lee Rd Unit B204, Winter Park, FL 32789

    $100 month rent decrease2 bedroom, 1 bathroom condo located in the desirable and well maintained Waterfall Cove community in Winter Park. New tile floor was installed and freshly painted. Washer & Dryer in the unit. No min credit score is required. Enjoy a highly walkable location close to Whole Foods, LA Fitness, Winter Park Village, shopping, dining, and more. Community amenities include a

    Mauricio Toro MTRE GROUPE LLC

    1695 Lee Rd Unit B204, Winter Park, FL 32789
  • /2

    $179,900

    Sold Jun 02, 2026

    3651 N Goldenrod Rd Unit 101, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Built 1990

    Last Sold Summary

    • 3% Below List Price
    • $214/SF
    • 44 Days On Market

    Current Estimated Value $178,219

    Last Listing Agent REZA Shirzad ANNE ROGERS REALTY GROUP INC

    3651 N Goldenrod Rd Unit 101, Winter Park, FL 32792
    • /2

      Est $1,510,637

      Not Listed For Sale

      2185 Talman Ct, Winter Park, FL 32792

      • 5 Beds
      • 6 Baths
      • 4,760 Sq Ft
      • Built 2008
      2185 Talman Ct, Winter Park, FL 32792

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  • /65

    $1,395,000

    Under Contract
    • 4 Beds
    • 4 Baths
    • 4,247 Sq Ft

    2873 Old Castle Dr, Winter Park, FL 32792

    Under contract-accepting backup offers. Welcome to 2873 Old Castle Drive, an exceptional property located within the sought-after gatedcommunity of Bear Gully Pointe in Winter Park. Nestled along the shores of Bear Lake, a 137-acre spring-fed lake, this stunning estate-like property sits on more than half an acre and issurrounded by lush landscaping, mature trees and beautifully

    Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

    2873 Old Castle Dr, Winter Park, FL 32792
  • /2

    $3,400 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    1939 Gunn Rd, Winter Park, FL 32792

    Adorable 3 bedroom, 2 bathroom one story home in Winter Park. Minutes from Baldwin Park and downtown Park Ave. The home has been beautifully renovated. There is a large backyard with paver patio area. Inside utility room with access to kitchen and carport area. Kitchen and family room are open to each other and boast plenty of built in storage. Designer light fixtures throughout the home.

    1939 Gunn Rd, Winter Park, FL 32792
  • /2

    $893,000

    Sold Oct 09, 2025

    2890 Wild Ginger Ct, Winter Park, FL 32792

    • 4 Beds
    • 4.5 Baths
    • 3,408 Sq Ft
    • Built 1993

    Last Sold Summary

    • 27% Below List Price
    • $262/SF
    • 78 Days On Market

    Current Estimated Value $903,710

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

    2890 Wild Ginger Ct, Winter Park, FL 32792
    • /2

      Est $422,559

      Not Listed For Sale

      1496 Broad Wing Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,755 Sq Ft
      • Built 2021
      1496 Broad Wing Ln, Winter Park, FL 32792

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Michelle Deleon BHHS FLORIDA REALTY

  • /28

    $424,900

    $70K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,746 Sq Ft

    5340 N Lake Burkett Ln, Winter Park, FL 32792

    Beat the heat in the Large Community Pool or bring your boat or jet skis and enjoy the Private Lake Access! There is also Fishing Dock and Playground further inviting you to enjoy the outdoors! Welcome to Exceptional Florida Living! Welcome to Trinity Bay, a charming community offering deeded access to Lake Burkett, a private 75-acre spring-fed ski lake featuring navigable access to Lake Martha.

    Tanya McDonnell RE/MAX TOWN & COUNTRY REALTY

    5340 N Lake Burkett Ln, Winter Park, FL 32792
  • /82

    $1,850 Per Month

    • 3 Beds
    • 2 Baths
    • 1,149 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit E215, Winter Park, FL 32789

    Discover your ideal home in this newly renovated 3-bedroom, 2-bathroom condo at Waterfall Cove in Winter Park, FL. Enjoy fresh paint, modern stainless steel appliances, and a fully upgraded kitchen that makes cooking a delight. Each spacious room offers plenty of natural light and comfort. This condo comes equipped with a washer and dryer, and includes cable and internet for your convenience. The

    Jenaia Fowlkes FOWLKES REALTY CO

    1695 Lee Rd Unit E215, Winter Park, FL 32789
  • /2

    $800,200

    Sold Oct 03, 2025

    4107 Gabriella Ln, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 3,074 Sq Ft
    • Built 1998

    Last Sold Summary

    • 33% Below List Price
    • $260/SF
    • 112 Days On Market

    Current Estimated Value $934,837

    Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

    4107 Gabriella Ln, Winter Park, FL 32792
    • /2

      Est $1,024,463

      Not Listed For Sale

      1975 Biscayne Dr, Winter Park, FL 32789

      • 5 Beds
      • 4 Baths
      • 3,270 Sq Ft
      • Built 2020
      1975 Biscayne Dr, Winter Park, FL 32789

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent nana Ahn SOGO REAL ESTATE SERVICES LLC

  • /5

    $2,700,000

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,588 Sq Ft

    648 Worthington Dr, Winter Park, FL 32789

    Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable pocket of Winter Park. A sophisticated modern farmhouse façade creates an impressive first impression, framed by a sweeping double-entry curved driveway that gives the home a commanding yet welcoming presence. Inside, the

    Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    648 Worthington Dr, Winter Park, FL 32789
  • /21

    $2,295 Per Month

    • 2 Beds
    • 2 Baths
    • 1,074 Sq Ft
    • House for Rent

    700 Melrose Ave, Winter Park, FL 32789

    Beautifully upgraded 2-bedroom, 2-bath condo in the heart of Winter Park! Located in a sought-after 55+ community surrounded by mature, lush landscaping, this charming condo offers the perfect blend of comfort and convenience. Enjoy a short walk to Mead Botanical Garden or the shops, dining, and entertainment along Park Avenue. With easy access to I-4, downtown Orlando, hospitals, shopping, and

    700 Melrose Ave, Winter Park, FL 32789
  • /2

    $405,500

    Sold May 28, 2026

    2834 Bright Bird Ln, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft
    • Built 2024

    Last Sold Summary

    • 7% Below List Price
    • $213/SF
    • 108 Days On Market

    Current Estimated Value $413,175

    Last Listing Agent Irene Navarro LIFESTYLE INTERNATIONAL REALTY

    2834 Bright Bird Ln, Winter Park, FL 32792
    • /2

      Est $1,743,988

      Not Listed For Sale

      643 Balmoral Rd, Winter Park, FL 32789

      643 Balmoral Rd, Winter Park, FL 32789

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Laura Hope COMPASS FLORIDA LLC

  • /26

    $370,000

    • 3 Beds
    • 2 Baths
    • 1,283 Sq Ft

    780 Baffie Ave, Winter Park, FL 32789

    Great opportunity to live in Winter Park in the Dubsdread Golf Community. This 3 bedroom, 2 bath home is situated on a deep lot (50 x 140) with 1283 sq. ft., Bamboo hardwood floors in several rooms, split bedroom floor plan, large kitchen with tile floors, and oak cabinets, and the dining room has a tongue and groove wood ceiling. The primary bedroom has Bamboo floors, tongue and groove wood

    Melissa Woodman FANNIE HILLMAN & ASSOCIATES

    780 Baffie Ave, Winter Park, FL 32789
  • /23

    $1,995 Per Month

    • 2 Beds
    • 1.5 Baths
    • 988 Sq Ft
    • Townhouse for Rent

    937 Aragon Ave, Winter Park, FL 32789

    Beautiful home located on a quaint, tree lined, brick street in desirable Winter Park. You will walk in a large family room with a wood burning fireplace and an open kitchen with beautiful new granite countertops and backsplach. Two bedrooms with walk in closets and a split bathroom with 2 vanities and 2 toilets. All new interior paint throughout. Kitchen was updated with custom backsplash and

    Vivian Lippi LIPPI REALTY LLC

    937 Aragon Ave, Winter Park, FL 32789
  • /2

    $430,000

    Sold Aug 19, 2026

    5225 Albert Dr, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,716 Sq Ft
    • Built 1979

    Last Sold Summary

    • 1% Below List Price
    • $251/SF
    • 2 Days On Market

    Current Estimated Value $400,745

    Last Listing Agent Celimar Sierra, LLC PREMIUM PROPERTIES R.E SERVICE

    5225 Albert Dr, Winter Park, FL 32792
    • /18

      Est $226,511

      Not Listed For Sale

      7781 Country Place Unit J-1, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,227 Sq Ft
      • Built 1988
      7781 Country Place Unit J-1, Winter Park, FL 32792

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Rick Protheroe RE/MAX TOWN & COUNTRY REALTY

Showing Results 321 - 360, Page 9 of 18

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