28,231

Winter Park, FL Homes

Section Image
  • /16

    $799,000

    • 3 Beds
    • 2.5 Baths
    • 1,957 Sq Ft

    1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789

    In the heart of Winter Park’s coveted Virginia Heights neighborhood, just moments from the boutiques, dining, and charm of Park Avenue and the green spaces of Seven Oaks Park, this exceptional Mediterranean-inspired end-unit condominium offers an unparalleled blend of elegance, comfort and accessible convenience. Encompassing nearly 2,000 square feet, the residence features three bedrooms,

    Nancy Merriam PREMIER SOTHEBY'S INTL. REALTY

    1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789
  • /13

    $1,999 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,550 Sq Ft
    • Townhouse for Rent

    2648 Galliano Cir, Winter Park, FL 32792

    ***New residents will receive three (3) complimentary months of the Resident Benefits Package (RBP). Take advantage of this exclusive offer and enjoy added benefits at no cost for your first three months!*** This property will not last long! Schedule a showing today! Winter Park Two Story 2/2.5 Townhome located in the Private - Gated Community of Vistas at Lake Howell. All Stainless Steel

    2648 Galliano Cir, Winter Park, FL 32792
  • /2

    $2,200,000

    Sold Jun 16, 2026

    2550 Venetian Way, Winter Park, FL 32789

    • 4 Beds
    • 5 Baths
    • 5,051 Sq Ft
    • Built 2008

    Last Sold Summary

    • 10% Below List Price
    • $436/SF
    • 63 Days On Market

    Current Estimated Value $2,395,569

    Last Listing Agent Felicia Donateli PALM PROPERTIES OF CF, INC.

    2550 Venetian Way, Winter Park, FL 32789
    • /2

      Est $427,270

      Not Listed For Sale

      2817 Bright Bird Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2024
      2817 Bright Bird Ln, Winter Park, FL 32792

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC

  • /29

    $499,000

    $81K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 1,818 Sq Ft

    1807 Hammerlin Ave Unit G, Winter Park, FL 32789

    Virtually Staged. **Price Improvement**Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events.Situated in the heart of Winter Park, this residence offers the perfect blend of

    Courtney Dietch ALL REAL ESTATE & INVESTMENTS

    1807 Hammerlin Ave Unit G, Winter Park, FL 32789
  • /15

    $1,500 Per Month

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

    Unlisted Address

    2 Bedrooms, 1 Bathroom located on the first floor. IGalley kitchen (with a dishwasher, microwave, range, refrigerator, and a washer/dryer combo), walk-in closet in the primary bedroom, and an open living/dining room combo filled with natural light. A private patio, playground, and park. It includes 1 assigned parking space.

    Kirsten Cantello TRUSTHOME PROPERTIES INC

    Unlisted Address
  • /2

    $2,875,000

    Sold Jul 15, 2026

    1724 Pine Ave, Winter Park, FL 32789

    • 3 Beds
    • 5 Baths
    • 4,425 Sq Ft
    • Built 2012

    Last Sold Summary

    • 7% Below List Price
    • $650/SF
    • 6 Days On Market

    Current Estimated Value $3,030,610

    Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

    1724 Pine Ave, Winter Park, FL 32789
    • /18

      Est $431,709

      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

      Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC

  • /50

    $1,380,000

    $95K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,170 Sq Ft

    1751 Goodrich Ave, Winter Park, FL 32789

    Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes

    Stephanie Baldner EXP REALTY LLC

    1751 Goodrich Ave, Winter Park, FL 32789
  • /43

    $4,500 Per Month

    • 3 Beds
    • 3 Baths
    • 1,345 Sq Ft
    • House for Rent

    344 Starling Rd, Winter Park, FL 32789

    For Rent – Beautifully Updated Home Near Lake Killarney!Located just minutes from Downtown Winter Park, Park Avenue, I-4, and Maitland, this beautifully updated home offers convenient access to nearby shops and dining. The 3-bedroom, 3-full-bath layout features open living spaces and modern finishes throughout. LVP flooring flows through the entire home, complemented by fresh paint, abundant

    Kelly Price KELLY PRICE & COMPANY LLC

    344 Starling Rd, Winter Park, FL 32789
  • /2

    $2,575,000

    Sold Oct 20, 2025

    1341 Place Picardy, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 4,469 Sq Ft
    • Built 2016

    Last Sold Summary

    • 8% Below List Price
    • $576/SF
    • 95 Days On Market

    Current Estimated Value $2,605,737

    Last Listing Agent Julie Bettosini STOCKWORTH REALTY GROUP

    1341 Place Picardy, Winter Park, FL 32789
    • /18

      Est $429,558

      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

      Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC

  • /34

    $539,000

    $21K PRICE DROP Pre-Foreclosure
    • 3 Beds
    • 3 Baths
    • 1,602 Sq Ft

    7641 Village Green Dr, Winter Park, FL 32792

    Welcome to this beautifully maintained home in the heart of Winter Park, where comfort, charm, and convenience come together effortlessly. Nestled in a central Florida community, this residence offers a warm and inviting atmosphere from the moment you step inside. The home features a spacious and functional layout filled with natural light, creating an ideal setting for both everyday living and

    7641 Village Green Dr, Winter Park, FL 32792
  • /25

    $1,590 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft
    • Townhouse for Rent

    3374 Cedar Springs Place Unit 155, Winter Park, FL 32792

    2br 2.5ba UPDATED home in Hidden Oaks, Winter Park!!! Kitchen UPDATED with GRANITE counters and solid wood cabinets, upgraded toilets throughout, updated sinks & faucets in all baths. TILE FLOORS downstairs with neutral tone carpet on stairs and second floor. Dry bar area in living room. Both bedrooms are upstairs, each with their own full bathroom! Half bath downstairs off the living/dining room

    Greg Mann BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P

    3374 Cedar Springs Place Unit 155, Winter Park, FL 32792
  • /2

    $714,000

    Sold Feb 25, 2026

    1449 Pelican Bay Trail, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,928 Sq Ft
    • Built 1982

    Last Sold Summary

    • $244/SF
    • 2 Days On Market

    Current Estimated Value $714,972

    Last Listing Agent Steven Ritz KELLER WILLIAMS WINTER PARK

    1449 Pelican Bay Trail, Winter Park, FL 32792
    • /18

      Est $441,517

      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

      Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC

  • /49

    $1,800,000

    • 5 Beds
    • 4.5 Baths
    • 4,029 Sq Ft

    281 Brewer Ave, Winter Park, FL 32789

    Short Sale. Welcome to this luxury, home in the heart of Winter Park. Less than a mile away from Park Ave. Winter Park that offers entertainment, restaurants, farmers market and so much more. A beautiful contemporary style home with modern interior finishes. Featuring an open floor plan, 5 bedrooms, 4.5 baths, a loft/flex space, media room, 2 study areas, front porch, back patio, lanai and so

    John Henthorn HENTHORN REAL ESTATE

    281 Brewer Ave, Winter Park, FL 32789
  • /12

    $1,800 Per Month

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

    3367 River View Way Unit 450, Winter Park, FL 32792

    Welcome to this beautifully updated 3-bedroom home . This home has been refreshed with many new features, including brand-new appliances, a new washer and dryer, a new stove, and a new dishwasher. The kitchen has also been upgraded with a beautiful new countertop, while the new wood flooring throughout gives the home a clean and modern feel. With its fresh updates and comfortable layout, this

    Hao Jun Chang CINO INTERNATIONAL INC

    3367 River View Way Unit 450, Winter Park, FL 32792
  • /2

    $435,000

    Sold May 15, 2026

    7445 Betty St, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,576 Sq Ft
    • Built 1983

    Last Sold Summary

    • $276/SF
    • 3 Days On Market

    Current Estimated Value $432,320

    Last Listing Agent Nicholas Macy LISTY, LLC

    7445 Betty St, Winter Park, FL 32792
    • /18

      Est $448,865

      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

      Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC

  • /43

    $1,750,000

    $115K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,307 Sq Ft

    2343 Versailles Ave, Winter Park, FL 32789

    This modern and sleek Winter Park residence, with over $130K of improvements, is tucked along a quiet dead-end street, offering a functional, open floorplan in an exceptional location. Recent upgrades make this home feel wonderfully fresh and new, including a Mosquito Nix misting system, Culligan whole-home water filtration system, fresh paint throughout the entire home, a beautifully remodeled

    MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    2343 Versailles Ave, Winter Park, FL 32789
  • /44

    $5,600 Per Month

    • 3 Beds
    • 3 Baths
    • 2,434 Sq Ft
    • Townhouse for Rent

    1136 S Pennsylvania Ave, Winter Park, FL 32789

    Welcome home to this beautifully appointed end-unit Georgetown townhome in the highly desirable Virginia Heights community. Ideally located just minutes from Rollins College, Park Avenue, and the best shopping, dining, and entertainment that Winter Park has to offer, this exceptional residence offers the perfect blend of elegance, comfort, and convenience. Step inside to discover a bright, open

    Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

    1136 S Pennsylvania Ave, Winter Park, FL 32789
  • /2

    $242,000

    Sold Oct 15, 2025

    200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792

    • 2 Beds
    • 1.5 Baths
    • 1,219 Sq Ft
    • Built 1970

    Last Sold Summary

    • 9% Below List Price
    • $199/SF
    • 125 Days On Market

    Current Estimated Value $234,719

    Last Listing Agent Jessica Geer A+ REALTY PROFESSIONALS, INC

    200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792
    • /88

      Est $1,865,465

      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

      Last Listing Agent Domenique Lombardo ROYALTY R E BOUTIQUE INC

  • /39

    $450,000

    • 5 Beds
    • 3 Baths
    • 1,442 Sq Ft

    2181 Linden Rd, Winter Park, FL 32792

    Welcome to 2181 Linden Road, where modern updates meet the everyday convenience of Winter Park living. Thoughtfully renovated and designed with flexibility in mind, this home offers a versatile layout, contemporary finishes, and a private separate-entry suite that adds valuable space for guests, a home office, or additional living arrangements. With no HOA, the property offers added flexibility

    Paula Chavez KELLER WILLIAMS ADVANTAGE III

    2181 Linden Rd, Winter Park, FL 32792
  • /10

    $1,700 Per Month

    • 2 Beds
    • 1.5 Baths
    • 990 Sq Ft
    • Condo for Rent

    7336 Forest Hill Ct Unit 240, Winter Park, FL 32792

    2-BEDROOM HOME IN WINTER PARK | END UNIT | PRIVATE FENCED PATIO | COMMUNITY POOL | WASHER & DRYER | NEAR FULL SAIL & UCFUpdated 2-bedroom, 1.5-bath end-unit townhome-style condo located in the Hidden Oaks community of Winter Park. This two-story residence offers approximately 990 sq. ft. of living space with a functional layout, natural light, and a convenient location close to major

    Mara Brasil REALIZE INTERNATIONAL REALTY L

    7336 Forest Hill Ct Unit 240, Winter Park, FL 32792
  • /2

    $99,000

    Sold May 27, 2026

    3028 George Mason Ave Unit 7, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,088 Sq Ft
    • Built 1974

    Last Sold Summary

    • 6% Below List Price
    • $91/SF
    • 5 Days On Market

    Last Listing Agent Alex Khalil EXP REALTY LLC

    3028 George Mason Ave Unit 7, Winter Park, FL 32792
    • /18

      Est $442,197

      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

      Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC

  • /27

    $1,249,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,936 Sq Ft

    Winter Park, FL 32789

    Pre-Construction. To be built. NEW CONSTRUCTION! Introducing an exquisite new construction home in Winter Park Grove, Winter Park's newest community! This residence is carefully curated by SGC Development, a highly respected local builder known for their dedication to quality and craftsmanship. This residence combines luxury living with the utmost convenience, located within walking distance to

    Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

    Winter Park, FL 32789
  • /13

    $2,595 Per Month

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • Townhouse for Rent

    3486 Bougainvillea Dr Unit B, Winter Park, FL 32792

    Nice house with 2 units in a great location and each unit is being rent separately. This property is located in the heart of Winter Park where everything is close by. This unit has great value, comes with a pool and is near all of the main colleges. Come and enjoy this unit with your family and friends. Please schedule your showing today before it is gone.

    Smithj Salomon LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

    3486 Bougainvillea Dr Unit B, Winter Park, FL 32792
  • /2

    $528,000

    Sold Nov 25, 2025

    4991 Tangerine Ave, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,124 Sq Ft
    • Built 1972

    Last Sold Summary

    • $249/SF
    • 5 Days On Market

    Current Estimated Value $527,072

    Last Listing Agent Edwin Ayala, Jr EXP REALTY LLC

    4991 Tangerine Ave, Winter Park, FL 32792
    • /39

      Est $846,093

      Not Listed For Sale

      1770 Mondrian Cir, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 2,193 Sq Ft
      • Built 2023
      1770 Mondrian Cir, Winter Park, FL 32789

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  • /5

    $1,000,000

    • Land
    • 4.93 Acres
    • $202,840 per Acre

    7839 University Garden Dr, Winter Park, FL 32792

    REMARKABLE LAND OPPORTUNITY IN WINTER PARK! Welcome to an exceptional real estate offering situated on 4.93 level, usable acres in the highly desirable Winter Park area (Zip Code 32792). This unique property features both an existing mobile home and a separate concrete block home, presenting an incredible value-add situation for investors, developers, or buyers looking for a place to live while

    Ioan Baciu PREMIUM PROPERTIES R.E SERVICE

    7839 University Garden Dr, Winter Park, FL 32792
  • /23

    $4,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,405 Sq Ft
    • Property for Rent

    616 Ellendale Dr, Winter Park, FL 32792

    Virtually Staged. Move right into this beautifully updated pool home in the highly desirable Winter Park Estates community, offering an exceptional combination of storage space, flexibility, and location. New A/C (2026), Freshly painted throughout (2026), New Kitchen Countertops coming soon (2026) this move-in-ready home features an open-concept layout filled with natural light, seamlessly

    Elena Sanchez BALDWIN PARK REALTY LLC

    616 Ellendale Dr, Winter Park, FL 32792
  • /2

    $1,300,000

    Sold Jul 24, 2026

    321 Sylvan Blvd, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,821 Sq Ft
    • Built 1940

    Last Sold Summary

    • 7% Below List Price
    • $461/SF
    • 0 Days On Market

    Current Estimated Value $1,280,780

    Last Listing Agent Mel Bernstein PREMIER SOTHEBYS INT'L REALTY

    321 Sylvan Blvd, Winter Park, FL 32789
    • /32

      Not Listed For Sale

      0 Grand Rd Unit MFRO6169911, Winter Park, FL 32792

      0 Grand Rd Unit MFRO6169911, Winter Park, FL 32792

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Rick Cole KELLER WILLIAMS WINTER PARK

  • /11

    $198,000

    $2K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,062 Sq Ft

    3060 George Mason Ave Unit 12, Winter Park, FL 32792

    Welcome to your new home in Winter Park!Completely remodeled unit with luxury finishes, ceramic floors, modern bathrooms, brand new kitchen with steel appliances and a nice quartz counter. Community amenities include pool, tennis and playground. Great Schools - zoned for Winter Park HS. Just minutes to Full Sail, UCF & Valencia. Don’t miss out on this gem!

    Adriana Sanchez AROD PARTNERS REALTY

    3060 George Mason Ave Unit 12, Winter Park, FL 32792
  • /14

    $1,600 Per Month

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

    1695 Lee Rd Unit C103, Winter Park, FL 32789

    Charming condo for Lease! location , Location , location ! This 2-bedroom, 1-bathroom apartment offers an open layout with plenty of natural light, a spacious living area, and a well-equipped kitchen with brand new interior paint job.Enjoy the convenience of in-unit laundry and modern amenities throughout. The apartment is situated in a serene community, offering easy access to shopping, dining,

    Yigit Orer EMPIRE NETWORK REALTY

    1695 Lee Rd Unit C103, Winter Park, FL 32789
  • /2

    $415,000

    Sold Mar 02, 2026

    875 W Lyman Ave, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 760 Sq Ft
    • Built 1925

    Last Sold Summary

    • 13% Below List Price
    • $546/SF
    • 60 Days On Market

    Current Estimated Value $440,049

    Last Listing Agent Joey Bruno CHARLES RUTENBERG REALTY ORLANDO

    875 W Lyman Ave, Winter Park, FL 32789
    • /2

      Est $99,301

      Not Listed For Sale

      7453 Daniel Webster Dr Unit D, Winter Park, FL 32792

      • 1 Bed
      • 1 Bath
      • 786 Sq Ft
      • Built 1974
      7453 Daniel Webster Dr Unit D, Winter Park, FL 32792

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Rizwan Rashid MNT INTERNATIONAL

Showing Results 641 - 680, Page 17 of 18

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