28,402

Winter Park, FL Homes

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  • /52

    $699,900

    Open Sat 11AM - 2PM $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,411 Sq Ft

    860 N Denning Dr, Winter Park, FL 32789

    **NEW CONSTRUCTION QUALITY | WALKABLE WINTER PARK | DESIGNER SMART HOME** This is not a remodel — it's a complete architectural transformation completed in September 2022. Taken to the slab and studs, this Winter Park residence was entirely rebuilt with new roof trusses, all-new electrical, new AC system (inside and out), tankless water heater, new plumbing, and smart irrigation — delivering true

    LaDarrius Sanders OUTLET REALTY

    860 N Denning Dr, Winter Park, FL 32789
  • /33

    $1,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,037 Sq Ft
    • Apartment for Rent

    652 Saint Johns Ct Unit 652, Winter Park, FL 32792

    Don't miss this opportunity! Beautiful apartment located in Winter Park, one of the most convenient and desirable areas in the Orlando region. Conveniently located near Full Sail University, Rollins College, shopping centers, restaurants, entertainment, and major highways. Enjoy the comfort of a well-maintained community featuring a swimming pool and common areas for relaxation. This apartment

    David Carballo HOME PRIME REALTY LLC

    652 Saint Johns Ct Unit 652, Winter Park, FL 32792
  • /2

    $430,000

    Sold Aug 08, 2025

    1006 Bradford Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,130 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Above List Price
    • $202/SF
    • 7 Days On Market

    Current Estimated Value $449,716

    Last Listing Agent Paul Giannotti TERZA REAL ESTATE

    1006 Bradford Dr, Winter Park, FL 32792
    • /27

      Est $160,603

      Not Listed For Sale

      603 Saint Johns Ct Unit S, Winter Park, FL 32792

      • 1 Bed
      • 1 Bath
      • 759 Sq Ft
      • Built 1981
      603 Saint Johns Ct Unit S, Winter Park, FL 32792

      Last Sold Summary

      • 3 Days On Market

  • /42

    $800,000

    • 5 Beds
    • 3 Baths
    • 2,194 Sq Ft

    739 Roughbeard Rd, Winter Park, FL 32792

    Welcome to Winter Park Pines, one of Winter Park’s most desirable neighborhoods. This updated 5 bed, 3 bath pool home features a split floor plan, generous room sizes, and wood-plank tile flooring throughout most of the home. Inside, the formal living and dining rooms flow together and overlook the pool through French doors, while the large primary suite offers an en-suite bath, walk-in closet,

    John Harbuck SERHANT

    739 Roughbeard Rd, Winter Park, FL 32792
  • /9

    $2,100 Per Month

    • 3 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Nice 3 bedroom, 2 bath single family home

    3036 Patel Dr, Winter Park, FL 32792

    Available May 1st! 3/2 with open-concept kitchen. Your new home has an open and airy living room/kitchen area with easy-to-maintain tile. A HUGE screened patio looks out to a private wooded backyard. Privacy fence and attached one-car garage make this the perfect place to call home! The home is nestled on a cul-de-sac minutes from Full Sail.All ERA Grizzard Real Estate residents are

    3036 Patel Dr, Winter Park, FL 32792
  • /2

    $390,000

    Sold Feb 23, 2026

    1670 Clematis Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,401 Sq Ft
    • Built 1962

    Last Sold Summary

    • 11% Below List Price
    • $278/SF
    • 81 Days On Market

    Current Estimated Value $382,015

    Last Listing Agent Gea Gomez LPT REALTY, LLC

    1670 Clematis Ln, Winter Park, FL 32792
    • /46

      Est $1,167,829

      Not Listed For Sale

      1778 Mondrian Cir, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 2,377 Sq Ft
      • Built 2023
      1778 Mondrian Cir, Winter Park, FL 32789

      Last Sold Summary

      • 51 Days On Market

  • /25

    $1,699,000

    $51K PRICE DROP Pending
    • 3 Beds
    • 3 Baths
    • 2,488 Sq Ft

    1110 Alabama Dr, Winter Park, FL 32789

    Come home to this stunning 3 Bed/3 Bath Winter Park residence, fully renovated down to the studs in 2020 and perfectly positioned on a premier corner lot at Alabama Drive and Palmer Avenue. Set among historic estate homes and the iconic tree-lined brick streets of the Chain of Lakes district, this home offers one of Winter Park’s most coveted addresses.Enjoy an unmatched lifestyle just moments

    Non-Member Mls Agent

    1110 Alabama Dr, Winter Park, FL 32789
  • /24

    $2,200 Per Month

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • Condo for Rent

    151 N Orlando Ave Unit 118, Winter Park, FL 32789

    Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

    Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

    151 N Orlando Ave Unit 118, Winter Park, FL 32789
  • /2

    $1,199,000

    Sold Jun 09, 2026

    1807 Magnolia Ave, Winter Park, FL 32789

    • 5 Beds
    • 3 Baths
    • 2,618 Sq Ft
    • Built 2026

    Last Sold Summary

    • $458/SF
    • 9 Days On Market

    Current Estimated Value $1,143,370

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    1807 Magnolia Ave, Winter Park, FL 32789
    • /44

      Est $877,952

      Not Listed For Sale

      1403 Michigan Ave, Winter Park, FL 32789

      • 4 Beds
      • 3.5 Baths
      • 2,513 Sq Ft
      • Built 2024
      1403 Michigan Ave, Winter Park, FL 32789

      Last Sold Summary

      • 65 Days On Market

  • /19

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,285 Sq Ft

    1605 Puritan Ave, Winter Park, FL 32792

    Stunning 3-bedroom, 2-bath remodeled home with no HOA, ideally located on the border of Winter Park and Orlando. This move-in-ready property features a new roof installed in July 2025, an updated kitchen with beautiful granite countertops and brand new appliances. Enjoy the perfect combination of comfort, style, and convenience with easy access to shopping, dining, schools, and major roadways.

    Angelica Tomlinson LLC CENTURY 21 CARIOTI

    1605 Puritan Ave, Winter Park, FL 32792
  • /22

    $1,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Spacious 3 bedroom Villa

    3056 Autumn Ct, Winter Park, FL 32792

    Discover this inviting villa in Winter Park, FL, featuring comfortable LVT flooring throughout and carpeted bedrooms. The home offers stainless steel appliances, ceiling fans, and a screened porch for added outdoor enjoyment. Residents have access to a community pool, and the location provides easy access to nearby shopping and restaurants as well as convenient connections to I-4 and 417.

    3056 Autumn Ct, Winter Park, FL 32792
  • /2

    $1,595,000

    Sold Sep 02, 2025

    1733 Harmon Ave, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,267 Sq Ft
    • Built 2025

    Last Sold Summary

    • $488/SF
    • 27 Days On Market

    Current Estimated Value $1,613,895

    Last Listing Agent Jordan Freeland SOUTH REALTY, INC

    1733 Harmon Ave, Winter Park, FL 32789
    • /18

      Est $436,927

      Not Listed For Sale

      2809 Bright Bird Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2024
      2809 Bright Bird Ln, Winter Park, FL 32792

      Last Sold Summary

      • 29 Days On Market

  • /16

    $319,900

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft

    751 Warrenton Rd, Winter Park, FL 32792

    Beautiful 3 bedroom 2 bath duplex in Winter Park in the Winter Park school district on a quiet dead end street near the Winter Park Pines Golf Course. Your new home is freshly painted inside and out, has updated kitchen and bathrooms, stainless steel appliances, new A/C system, new roof, and a new hot water heater. There is no need to worry about your yard, your bushes, or your fence, they are

    Stephen Hachey FLAT FEE MLS REALTY

    751 Warrenton Rd, Winter Park, FL 32792
  • /21

    $2,400 Per Month

    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft
    • Townhouse for Rent

    2657 Exuma Way, Winter Park, FL 32792

    Freshly remodeled and move-in ready, this 3-bedroom, 2-bath townhome offers comfortable living in a highly desirable Winter Park location. The open-concept living and dining areas create a welcoming space for everyday living and entertaining, while the convenient pass-through window connects the kitchen and dining room for added functionality. The brand-new kitchen remodel features granite

    Jerry Agan HAVEN PROPERTY GROUP LLC

    2657 Exuma Way, Winter Park, FL 32792
  • /2

    $749,000

    Sold Aug 13, 2025

    627 Darcey Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,509 Sq Ft
    • Built 1967

    Last Sold Summary

    • 6% Below List Price
    • $299/SF
    • 52 Days On Market

    Current Estimated Value $775,588

    Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

    627 Darcey Dr, Winter Park, FL 32792
    • /18

      Est $435,013

      Not Listed For Sale

      2805 Bright Bird Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2024
      2805 Bright Bird Ln, Winter Park, FL 32792

      Last Sold Summary

      • 6 Days On Market

  • /28

    $170,000

    $3K PRICE INCREASE Pending
    • 1 Bed
    • 1 Bath
    • 793 Sq Ft

    200 Saint Andrews Blvd Unit 312, Winter Park, FL 32792

    Beautifully maintained condo in a prime Winter Park location! This bright and inviting unit has been exceptionally well cared for and shows true pride of ownership. The interior is spotless, featuring a clean, modern feel with comfortable living spaces that make it easy to feel right at home. Enjoy a well-designed layout with plenty of natural light and a welcoming atmosphere throughout. The

    Reinaldo Roman ROMAN'S PRO REALTY LLC

    200 Saint Andrews Blvd Unit 312, Winter Park, FL 32792
  • /15

    $2,095 Per Month

    • 3 Beds
    • 2 Baths
    • 1,083 Sq Ft
    • 3 Bedroom 2 Bath Duplex in Winter Park For RENT!

    2700 Tortoise Cove, Winter Park, FL 32792

    * 3 Bedroom 2 bath with a 2 car garage, 1083 sq. ft.* Eat in kitchen, stove, fridge, dishwasher included* Kitchen newly remodeled* Blinds and Ceiling fans* Tile through out* Walk in closets* Rear yard privacy fence* All new paint, and fencing* Rear patio* Sliding glass doors off master to back yard* Pet Friendly* Washer dryer hookups in garage*

    2700 Tortoise Cove, Winter Park, FL 32792
  • /2

    $1,095,000

    Sold Dec 01, 2025

    1450 Chestnut Ave, Winter Park, FL 32789

    • 3 Beds
    • 3.5 Baths
    • 1,942 Sq Ft
    • Built 2009

    Last Sold Summary

    • 16% Below List Price
    • $564/SF
    • 49 Days On Market

    Current Estimated Value $1,123,145

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    1450 Chestnut Ave, Winter Park, FL 32789
    • /18

      Est $443,193

      Not Listed For Sale

      2821 Bright Bird Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,782 Sq Ft
      • Built 2024
      2821 Bright Bird Ln, Winter Park, FL 32792

      Last Sold Summary

      • 49 Days On Market

  • /44

    $1,045,000

    Open Sun 2PM - 4PM
    • 4 Beds
    • 4.5 Baths
    • 2,638 Sq Ft

    616 Brechin Dr, Winter Park, FL 32792

    Welcome to your fully reimagined Florida home. Among tree-canopied streets in the desired Kenilworth Shores neighborhood, this mid-century modern ranch home was completely transformed in 2005. The redesign added substantial square footage and created a completely unique, functional floor plan that separates it from any other home in the area. Spanning 2,638 square feet of seamless indoor-outdoor

    Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    616 Brechin Dr, Winter Park, FL 32792
  • /10

    $2,600 Per Month

    • 3 Beds
    • 3 Baths
    • 1,782 Sq Ft
    • Townhouse for Rent

    2737 Bright Bird Ln, Winter Park, FL 32792

    DO not miss out on this thoughtfully designed townhome! This gorgeous end unit Marigold two-story townhome has no direct rear neighbors, water view and features a Craftsman exterior. Townhome offers 3 bedrooms, 2 full bathrooms, a powder room, a two-car garage and a covered lanai. The kitchen is fully equipped with a pantry, modern gray cabinetry, a Suite Arabesque ceramic tile backsplash, Lagoon

    Nicole Howell FANNIE HILLMAN & ASSOCIATES

    2737 Bright Bird Ln, Winter Park, FL 32792
  • /2

    $220,000

    Sold Jan 30, 2026

    700 Melrose Ave Unit J23, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 772 Sq Ft
    • Built 1964

    Last Sold Summary

    • 6% Below List Price
    • $285/SF
    • 107 Days On Market

    Current Estimated Value $217,744

    Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

    700 Melrose Ave Unit J23, Winter Park, FL 32789
    • /18

      Est $447,813

      Not Listed For Sale

      2796 Bright Bird Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,782 Sq Ft
      • Built 2024
      2796 Bright Bird Ln, Winter Park, FL 32792

      Last Sold Summary

      • 78 Days On Market

  • /48

    $469,900

    Pending
    • 4 Beds
    • 2 Baths
    • 1,863 Sq Ft

    5350 Orange Ave, Winter Park, FL 32792

    Under contract-accepting backup offers. 4 BEDROOM | 2 BATH | 1,863 SQ FT + TINY HOUSE GUEST SUITE | CUSTOM BUILD | NO HOA | WINTER PARK | Located just minutes from the charm and energy of Downtown Winter Park, this exceptional custom-built residence offers a rare opportunity to enjoy thoughtfully crafted living in one of Central Florida's most convenient and desirable corridors. Built in 2011 in

    Bruce Gordon ABSOLUTE REALTY GROUP, LLC

    5350 Orange Ave, Winter Park, FL 32792
  • /23

    $1,175 Per Month

    • 1 Bed
    • 1 Bath
    • 537 Sq Ft
    • One bedroom apt 7 or 12 months furnish or unfurnished. Apartamento disponible amueblado o sin mue...

    3075 Aaron Burr Ave, Winter Park, FL 32792

    Centrally located in Winter Park near Full Sail University, and check out this cute move-in ready, 1 Bed/1 Bath second-floor condo with a rear balcony. All tiled flooring, new paint, new toilets and light fixtures, new dishwasher and range. The community features a large swimming pool and a coined laundry room inside a community multipurpose room. This location is zoned for A-rated schools and

    3075 Aaron Burr Ave, Winter Park, FL 32792
  • /2

    $400,000

    Sold Feb 13, 2026

    2833 Prince John Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,605 Sq Ft
    • Built 1963

    Last Sold Summary

    • 7% Below List Price
    • $249/SF
    • 9 Days On Market

    Current Estimated Value $409,870

    Last Listing Agent Makena Clark EXIT REALTY PREMIER LEGACY

    2833 Prince John Rd, Winter Park, FL 32792
    • /88

      Est $1,834,590

      Not Listed For Sale

      1661 Hillcrest Ave, Winter Park, FL 32789

      • 4 Beds
      • 3.5 Baths
      • 3,161 Sq Ft
      • Built 2017
      1661 Hillcrest Ave, Winter Park, FL 32789

      Last Sold Summary

      • 21 Days On Market

  • /33

    $320,000

    $10K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,719 Sq Ft

    2401 Antilles Dr, Winter Park, FL 32792

    Under contract-accepting backup offers. Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. The home has newer A/C, high impact windows and the home has been

    George Freelove KELLER WILLIAMS REALTY AT THE PARKS

    2401 Antilles Dr, Winter Park, FL 32792
  • /11

    $4,200 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,589 Sq Ft
    • House for Rent

    1235 Verdant Glade Place, Winter Park, FL 32792

    Winter Park Community, great schools, Hawk’s Crest’s gated community, all lawn maintenance included, community pool/gym/2 playgrounds, fenced, 2596 sqft, 2 story, two-car garage with AC, 4 bedrooms, 3 1/2 baths, 10 ft x 10 ft office, huge loft, gourmet kitchen, reverse osmosis water filter, microwave is built-in above the oven, Ring security system, living room includes wall mounted 86” LG 4K

    Steven Koleno BEYCOME OF FLORIDA LLC

    1235 Verdant Glade Place, Winter Park, FL 32792
  • /2

    $290,000

    Sold Sep 22, 2025

    7102 Easter St, Winter Park, FL 32792

    • 3 Beds
    • 1 Bath
    • 1,114 Sq Ft
    • Built 1956

    Last Sold Summary

    • 3% Below List Price
    • $260/SF
    • 67 Days On Market

    Current Estimated Value $297,596

    Last Listing Agent Mayken Giraldo THE C SMITH REAL ESTATE GROUP LLC

    7102 Easter St, Winter Park, FL 32792
    • /2

      Est $451,258

      Not Listed For Sale

      2719 Bright Bird Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,780 Sq Ft
      • Built 2024
      2719 Bright Bird Ln, Winter Park, FL 32792

      Last Sold Summary

  • /21

    $154,900

    • 1 Bed
    • 1 Bath
    • 749 Sq Ft

    3037 Antique Oaks Cir Unit 156, Winter Park, FL 32792

    Cute as a button and move-in ready! This charming top floor 1-bedroom, 1-bath condo offers a bright, airy feel with an open-concept layout designed for comfortable living. Literally just steps away, you will enjoy peaceful views overlooking the hot tub and community pool from your private retreat above it all! The updated kitchen features beautiful white cabinetry with SOFT-CLOSE DRAWERS,

    Chuck Valence VALENCE REALTY GROUP

    3037 Antique Oaks Cir Unit 156, Winter Park, FL 32792
  • /11

    $1,950 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,024 Sq Ft
    • House for Rent

    731 W Comstock Ave, Winter Park, FL 32789

    Close to downtown Winter Park, Winter Park Village, and Park Avenue - Charming 3 bedroom 1.5 bath home, with single carport, fenced backyard, ceiling fans and blinds. Tile floors in main living areas and NEW carpet in bedrooms. Additional sun room located off the kitchen with entry to/from carport. This home is available for immediate move in. PETS NEGOTIABLE. Please call to schedule an

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

    $805,000

    Sold Jul 01, 2025

    1795 Walker Ave, Winter Park, FL 32789

    • 5 Beds
    • 3 Baths
    • 1,813 Sq Ft
    • Built 1958

    Last Sold Summary

    • 17% Below List Price
    • $444/SF
    • 143 Days On Market

    Current Estimated Value $808,096

    Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

    1795 Walker Ave, Winter Park, FL 32789
    • /18

      Est $442,064

      Not Listed For Sale

      2790 Bright Bird Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,782 Sq Ft
      • Built 2024
      2790 Bright Bird Ln, Winter Park, FL 32792

      Last Sold Summary

      • 19 Days On Market

Showing Results 481 - 520, Page 13 of 18

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