28,401

Winter Park, FL Homes

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  • /29

    $2,695,000

    • 3 Beds
    • 3.5 Baths
    • 3,048 Sq Ft

    413 W Morse Blvd, Winter Park, FL 32789

    LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, boutique shops, banks, post office, farmers market, Central Park and Rollins College. Designed by architect Phil Kean and built in 2017 the owners have embellished this townhome with custom millwork and finishes, wood floors, sound

    A.V. Blalock COLDWELL BANKER REALTY

    413 W Morse Blvd, Winter Park, FL 32789
  • /20

    $2,100 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,236 Sq Ft
    • Condo for Rent

    5171 Lazy Oaks Dr Unit 5171, Winter Park, FL 32792

    This Winter Park condo features two bedrooms and three bathrooms, with an attached garage for convenient parking. The entrance welcomes you with a charming foyer. At the heart of the spacious open great room is the kitchen—highlighted by custom cabinets, quartz countertops, and stainless-steel appliances, all thoughtfully arranged on the first floor. An oversized counter provides space for

    Joyce Gary PAINE-ANDERSON PROPERTIES, INC

    5171 Lazy Oaks Dr Unit 5171, Winter Park, FL 32792
  • /2

    $475,000

    Sold May 14, 2026

    665 W Lyman Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,119 Sq Ft
    • Built 1994

    Last Sold Summary

    • 6% Above List Price
    • $424/SF
    • 6 Days On Market

    Current Estimated Value $447,753

    Last Listing Agent Jonathan Nakhnoukh CENTRAL FLORIDA PRIME REAL ESTATE LLC

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

      Est $439,610

      Not Listed For Sale

      2865 Clever Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2023
      2865 Clever Ln, Winter Park, FL 32792

      Last Sold Summary

      • 140 Days On Market

  • /7

    $375,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 1,656 Sq Ft

    1761 Gladiolas Dr, Winter Park, FL 32792

    Under contract-accepting backup offers. INVESTOR SPECIAL! Priced to sell and loaded with potential, this 4-bedroom, 2.5-bath home in Winter Park offers an excellent opportunity for investors, renovators, or buyers looking to add their personal touch. Situated on a spacious corner lot in the established Garden Lake Estates community, the property features 1,656 square feet of living space, a

    Mauricio Gomez LPT REALTY, LLC

    1761 Gladiolas Dr, Winter Park, FL 32792
  • /7

    $1,350 Per Month

    • 1 Bed
    • 1 Bath
    • 759 Sq Ft
    • 1/1 @ Winter Park Villas

    667 Trinidad Ct, Winter Park, FL 32792

    1/1 condo at Winter Park Villas. Minutes from UCF,Full Sail University and downtown Winter Park. Winter Park Villas community have many amenities, including pool, tennis court,fitness room, car care center, and picnic area w/ grills.Appointment require to show the unitClose to bus line. Pets are subject of approval of owner/HOA. Security Deposit amount subject to credit/background

    667 Trinidad Ct, Winter Park, FL 32792
  • /2

    $168,146

    Sold Jun 01, 2026

    1000 S Semoran Blvd Unit 805, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,003 Sq Ft
    • Built 1969

    Last Sold Summary

    • 6% Below List Price
    • $168/SF
    • 46 Days On Market

    Current Estimated Value $173,010

    Last Listing Agent Carrie Shawfield SHAWFIELD REALTY GROUP

    1000 S Semoran Blvd Unit 805, Winter Park, FL 32792
    • /32

      Est $598,656

      Not Listed For Sale

      1178 Wildmeadow Run, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,770 Sq Ft
      • Built 2021
      1178 Wildmeadow Run, Winter Park, FL 32792

      Last Sold Summary

      • 6 Days On Market

  • /34

    $745,000

    • 2 Beds
    • 3 Baths
    • 1,440 Sq Ft

    408 Holt Ave, Winter Park, FL 32789

    Rare investment opportunity in the heart of Winter Park/Rollins College area. This turnkey, fully renovated triplex is located within one of Winter Park’s highest-demand rental corridors, just steps from Rollins College, Park Avenue, and Lake Virginia. The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick street

    Brian Opre THE REAL ESTATE PRINCIPLE, INC

    408 Holt Ave, Winter Park, FL 32789
  • /30

    $2,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,106 Sq Ft
    • House for Rent

    7522 Laurel Springs Dr, Winter Park, FL 32792

    Located in the highly sought-after Winter Park High School district, this beautifully maintained 3-bedroom, 2-bath home in Laurel Springs provides comfort, space, and convenience. The bright and inviting living area features tile and an open, welcoming feel. Enjoy year-round indoor-outdoor living in the expansive 400+ sq. feet. enclosed patio overlooking a fully fenced backyard—perfect for

    Liu Zhang JOY ESTATE ENTERPRISE INC

    7522 Laurel Springs Dr, Winter Park, FL 32792
  • /2

    $170,000

    Sold Sep 24, 2025

    200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,119 Sq Ft
    • Built 1970

    Last Sold Summary

    • 10% Below List Price
    • $152/SF
    • 74 Days On Market

    Current Estimated Value $181,789

    Last Listing Agent Evelyn Pilchick RE/MAX 200 REALTY

    200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792
    • /2

      Est $96,196

      Not Listed For Sale

      3035 George Mason Ave Unit 18, Winter Park, FL 32792

      • 1 Bed
      • 1 Bath
      • 549 Sq Ft
      • Built 1974
      3035 George Mason Ave Unit 18, Winter Park, FL 32792

      Last Sold Summary

      • 196 Days On Market

  • /62

    $4,195,000

    New Construction $555K PRICE DROP
    • 4 Beds
    • 5.5 Baths
    • 3,850 Sq Ft

    1150 Via Salerno, Winter Park, FL 32789

    In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Now offered at a newly adjusted price, the home presents a compelling opportunity to experience design-forward new construction in the Vias neighborhood. Developed and designed by Steve & Jodie Warrick Konold of Scout & Co., the 3,850-sf

    Padgett McCormick KELLY PRICE & COMPANY LLC

    1150 Via Salerno, Winter Park, FL 32789
  • /24

    $1,495 Per Month

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

    2942 Antique Oaks Cir Unit 88, Winter Park, FL 32792

    This beautiful one-bedroom, one-bath 749 sqft condo is located in the Parkview Village community near Semoran and Aloma. Located on the second floor, the condominium offers an expansive feeling with the kitchen open to the living room and dining area. Off to the side of the living area is a sliding glass door that leads to the private patio, a perfect spot to enjoy your morning cup of coffee. The

    2942 Antique Oaks Cir Unit 88, Winter Park, FL 32792
  • /2

    $475,000

    Sold Feb 02, 2026

    1740 Anzle Ave, Winter Park, FL 32789

    • 4 Beds
    • 2 Baths
    • 1,808 Sq Ft
    • Built 1956

    Last Sold Summary

    • 40% Below List Price
    • $263/SF
    • 109 Days On Market

    Current Estimated Value $607,200

    Last Listing Agent Freddy DeCoster GOYAL & DECOSTER REALTY

    1740 Anzle Ave, Winter Park, FL 32789
    • /18

      Est $429,511

      Not Listed For Sale

      1916 Erudite Way, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,782 Sq Ft
      • Built 2024
      1916 Erudite Way, Winter Park, FL 32792

      Last Sold Summary

      • 146 Days On Market

  • /34

    $595,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,370 Sq Ft

    508 Dunraven Dr, Winter Park, FL 32792

    Welcome to this stylishly renovated ranch-style pool home in Kenilworth Shores, a special Winter Park neighborhood known for its connected community, central location, and easy access to everything people love about Winter Park. This beautifully renovated 3-bedroom, 2-bath home sits on nearly a quarter-acre lot and offers the perfect blend of style, comfort, and outdoor living. Step inside and

    Kathryn Stelljes KELLER WILLIAMS REALTY AT THE PARKS

    508 Dunraven Dr, Winter Park, FL 32792
  • /8

    $2,995 Per Month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    1137 S Pennsylvania Ave, Winter Park, FL 32789

    Location!!Walking distance to Rollins campus and to downtown Winter Park. Beautiful 3-bedroom 2-bathroom home. Recently renovated kitchen and freshly painted. Nearby schools include Audubon Park elementary, Glenridge Middle School, and Winter Park education center school. This house is in the perfect location, close to great restaurants and within walking distance to Winter Park farmer's

    Raquel Elliott COLDWELL BANKER REALTY

    1137 S Pennsylvania Ave, Winter Park, FL 32789
  • /2

    $2,750,000

    Sold Jun 18, 2026

    151 Oakwood Way, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 4,129 Sq Ft
    • Built 2023

    Last Sold Summary

    • 14% Below List Price
    • $666/SF
    • 113 Days On Market

    Current Estimated Value $2,884,311

    Last Listing Agent Matthew Burks CORCORAN PREMIER REALTY

    151 Oakwood Way, Winter Park, FL 32789
    • /2

      Est $530,004

      Not Listed For Sale

      1051 Aragon Ave Unit 1051, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 1,669 Sq Ft
      • Built 1987
      1051 Aragon Ave Unit 1051, Winter Park, FL 32789

      Last Sold Summary

      • 104 Days On Market

  • /48

    $1,139,750

    $35K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,656 Sq Ft

    2702 Parkland Dr, Winter Park, FL 32789

    Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace

    Elizabeth Nordquist NORDQUIST & COMPANY INC

    2702 Parkland Dr, Winter Park, FL 32789
  • /7

    $1,600 Per Month

    • 2 Beds
    • 2 Baths
    • 967 Sq Ft
    • 1/2 Duplex in Winter Park

    3012 Patel Dr, Winter Park, FL 32792

    Nice two bedroom, two bath home with spacious kitchen and living area. House is tiled throughout. Driveway accommodates 2 cars. Fenced in backyard with small shed. Close to Target, Costco Publix, Aldi. Winter Park Schools.

    3012 Patel Dr, Winter Park, FL 32792
  • /2

    $325,000

    Sold Oct 03, 2025

    260 Killarney Bay Ct Unit 6, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft
    • Built 1986

    Last Sold Summary

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

    Current Estimated Value $325,603

    Last Listing Agent Tyler Gibson LPT REALTY, LLC

    260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
    • /2

      Est $372,693

      Not Listed For Sale

      7632 Aloma Pines Ct, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,872 Sq Ft
      • Built 2018
      7632 Aloma Pines Ct, Winter Park, FL 32792

      Last Sold Summary

      • 129 Days On Market

  • /55

    $735,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,739 Sq Ft

    738 S Pennsylvania Ave, Winter Park, FL 32789

    Under contract-accepting backup offers. Experience the pinnacle of the Winter Park lifestyle in this enchanting historic cottage, offering an unbeatable, highly walkable location just a 2-minute stroll from the pristine campus of Rollins College, a 4-minute walk to the neighborhood coffee shop, and approximately 11 minutes on foot to the boutique shops, world-class dining, and scenic shores of

    Justin Jodha COMPASS FLORIDA LLC

    738 S Pennsylvania Ave, Winter Park, FL 32789
  • /16

    $1,500 Per Month

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

    7340 Swallow Run Unit 7340, Winter Park, FL 32792

    Check out this 2nd floor 2-bedroom, 2 bathroom condo with brand new beautiful wood floors throughout. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options.

    Bobby Mills METRO CITY REALTY

    7340 Swallow Run Unit 7340, Winter Park, FL 32792
  • /2

    $1,725,000

    Sold Mar 05, 2026

    617 Worthington Dr, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,533 Sq Ft
    • Built 2018

    Last Sold Summary

    • 13% Below List Price
    • $488/SF
    • 215 Days On Market

    Current Estimated Value $1,755,958

    Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

    617 Worthington Dr, Winter Park, FL 32789
    • /32

      Est $462,418

      Not Listed For Sale

      2445 Firstlight Way, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 2,010 Sq Ft
      • Built 2018
      2445 Firstlight Way, Winter Park, FL 32792

      Last Sold Summary

      • 41 Days On Market

  • /30

    $245,000

    Pending
    • 1 Bed
    • 1 Bath
    • 787 Sq Ft

    700 Melrose Ave Unit K25, Winter Park, FL 32789

    Under contract-accepting backup offers. Bright, beautifully updated 1-bed/1-bath condo with floor-to-ceiling views and a prime walkable location in the heart of Winter Park. The renovated kitchen and bath shine with modern finishes, while expansive windows frame serene, ever-changing views of the lushly landscaped grounds. Set within the sought-after Winter Park Gardens, residents enjoy 8 acres

    Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

    700 Melrose Ave Unit K25, Winter Park, FL 32789
  • /14

    $1,595 Per Month

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

    1695 Lee Rd Unit Apartment A103, Winter Park, FL 32789

    2 Bedrooms, 1 Bathroom located on the first floor. Galley 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.This property offers an option of a security deposit-free lease

    1695 Lee Rd Unit Apartment A103, Winter Park, FL 32789
  • /2

    $286,000

    Sold May 22, 2026

    3204 Netherwood Dr, Winter Park, FL 32792

    • 2 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • Built 1983

    Last Sold Summary

    • 12% Below List Price
    • $271/SF
    • 66 Days On Market

    Current Estimated Value $294,110

    Last Listing Agent Renee Anthony WATSON REALTY CORP.

    3204 Netherwood Dr, Winter Park, FL 32792
    • /62

      Est $1,992,428

      Not Listed For Sale

      2156 Talman Ct, Winter Park, FL 32792

      • 5 Beds
      • 8 Baths
      • 7,762 Sq Ft
      • Built 2008
      2156 Talman Ct, Winter Park, FL 32792

      Last Sold Summary

      • 32 Days On Market

  • /34

    $645,000

    Open Sun 2AM - 4PM
    • 4 Beds
    • 2 Baths
    • 1,560 Sq Ft

    2774 Banchory Rd, Winter Park, FL 32792

    Some homes are updated. Others are completely reimagined.At 2774 Banchory Road, the transformation started with a bold decision: remove the walls and rethink how the home lives. The result is a light-filled great room where the kitchen, dining, and living spaces flow together effortlessly—creating the kind of open, connected lifestyle today's buyers are searching for.The kitchen was

    Shelley Dawson COMPASS FLORIDA LLC

    2774 Banchory Rd, Winter Park, FL 32792
  • /58

    $3,300 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,891 Sq Ft
    • House for Rent

    1843 Shadyhill Terrace, Winter Park, FL 32792

    Available for lease in the desirable Autumn Glen community of Winter Park. This spacious and well-maintained 4-bedroom, 2-bathroom single-family home offers comfort, space, and serenity in a peaceful neighborhood setting. Thoughtfully landscaped with lush greenery and tranquil water views, the home features an oversized kitchen with stainless steel appliances, ample storage, and a pass-through

    Beatrice Miranda METRO CITY REALTY

    1843 Shadyhill Terrace, Winter Park, FL 32792
  • /2

    $385,000

    Sold Nov 12, 2025

    4421 Steed Terrace, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 1,788 Sq Ft
    • Built 1989

    Last Sold Summary

    • 14% Below List Price
    • $215/SF
    • 209 Days On Market

    Current Estimated Value $416,071

    Last Listing Agent Andrey Bustamante BUSTAMANTE REAL ESTATE INC

    4421 Steed Terrace, Winter Park, FL 32792
    • /20

      Est $461,454

      Not Listed For Sale

      2448 Firstlight Way, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 2,076 Sq Ft
      • Built 2020
      2448 Firstlight Way, Winter Park, FL 32792

      Last Sold Summary

      • 89 Days On Market

  • /58

    $2,895,000

    Pending
    • 5 Beds
    • 4.5 Baths
    • 4,091 Sq Ft

    670 Williams Dr, Winter Park, FL 32789

    Graceful and timeless, this classic Southern-inspired residence by esteemed builder Charles Clayton sits on a generous lot in Winter Park’s coveted Park Grove neighborhood and makes a striking first impression with beautifully composed architecture, charming dormer windows, a sweeping front porch with historic reclaimed Detroit brick flooring, and curated landscaping. Inside, the foyer unfolds

    MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    670 Williams Dr, Winter Park, FL 32789
  • /16

    $1,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Excellent location

    4968 Tangerine Ave Unit 4968, Winter Park, FL 32792

    This roomy condo is available for immediate occupancy. New Luxury Vinyl Plank floors just installed. The unit is ideally located in Winter Park, not far from Full Sail or UCF. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet community with plenty of privacy. Amenities include a pool and workout room. Call today for your private tour of this amazing

    4968 Tangerine Ave Unit 4968, Winter Park, FL 32792
  • /2

    $2,835,000

    Sold Nov 24, 2025

    255 Stirling Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,635 Sq Ft
    • Built 1982

    Last Sold Summary

    • 14% Below List Price
    • $780/SF
    • 25 Days On Market

    Current Estimated Value $2,868,037

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

    255 Stirling Ave, Winter Park, FL 32789
    • /22

      Est $197,057

      Not Listed For Sale

      200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 987 Sq Ft
      • Built 1970
      200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792

      Last Sold Summary

      • 4 Days On Market

Showing Results 641 - 680, Page 17 of 18

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