28,401

Winter Park, FL Homes

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  • /6

    $2,235,000

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 4,150 Sq Ft

    926 Enclave Place, Winter Park, FL 32792

    Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a

    Laura Earl CORCORAN PREMIER REALTY

    926 Enclave Place, Winter Park, FL 32792
  • /16

    $2,390 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,277 Sq Ft
    • House for Rent

    2866 Euston Rd, Winter Park, FL 32789

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

    2866 Euston Rd, Winter Park, FL 32789
  • /2

    $180,000

    Sold Feb 27, 2026

    200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 987 Sq Ft
    • Built 1970

    Last Sold Summary

    • 8% Below List Price
    • $182/SF
    • 11 Days On Market

    Current Estimated Value $184,242

    Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

    200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792
    • /2

      Est $1,761,051

      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

  • /6

    $99,000

    • Studio
    • 1 Bath
    • 537 Sq Ft

    3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792

    Attention investors! Take a look at this great opportunity to purchase a Cozy Condo located in Winter Park, FL. This studio condo features beautiful tile floors and lots of closet space. First-floor unit with open patio. Minutes away from Downtown Winter Park, expressway, downtown Orlando, Full Sail, and the University of Central Florida. This community offers a pool, tennis court, and clubhouse.

    Lynda Cheros GOLDENCREST REALTY LLC

    3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792
  • /20

    $2,200 Per Month

    • 3 Beds
    • 1.5 Baths
    • 950 Sq Ft
    • House for Rent

    5212 N Indiana Ave, Winter Park, FL 32792

    Property Id: 2594162Welcome to this beautifully remodeled 1,000-square-foot Mid-Century Modern home offering the perfect blend of timeless design and modern updates. This charming residence features 3 spacious bedrooms and 1.5 updated bathrooms, creating a comfortable and functional layout for everyday living. The heart of the home is the stunning new kitchen, showcasing crisp white

    5212 N Indiana Ave, Winter Park, FL 32792
  • /2

    $115,000

    Sold May 08, 2026

    1000 S Semoran Blvd Unit 512, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,072 Sq Ft
    • Built 1969

    Last Sold Summary

    • 11% Below List Price
    • $107/SF
    • 41 Days On Market

    Current Estimated Value $128,056

    Last Listing Agent Cristina Burgos REALSOURCE PROPERTY MANGNT LLC

    1000 S Semoran Blvd Unit 512, Winter Park, FL 32792
    • /18

      Est $231,908

      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

  • /4

    $2,050,000

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,813 Sq Ft

    930 Enclave Place, Winter Park, FL 32792

    Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a

    Matthew Burks CORCORAN PREMIER REALTY

    930 Enclave Place, Winter Park, FL 32792
  • /20

    $2,435 Per Month

    • 3 Beds
    • 2 Baths
    • 1,921 Sq Ft
    • House for Rent

    1546 Peruvian Ln, Winter Park, FL 32792

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2579.90. That covers your base rent, $2435.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1546 Peruvian Ln, Winter Park, FL 32792
  • /2

    $4,772,500

    Sold Sep 18, 2025

    765 Via Lugano, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 4,319 Sq Ft
    • Built 2019

    Last Sold Summary

    • $1,105/SF
    • 1 Day On Market

    Current Estimated Value $4,778,066

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

    765 Via Lugano, Winter Park, FL 32789
    • /2

      Est $226,457

      Not Listed For Sale

      7468 Swallow Run Unit 38, Winter Park, FL 32792

      • 2 Beds
      • 2.5 Baths
      • 1,578 Sq Ft
      • Built 1974
      7468 Swallow Run Unit 38, Winter Park, FL 32792

      Last Sold Summary

      • 52 Days On Market

  • /36

    $579,000

    Pending
    • 4 Beds
    • 2 Baths
    • 1,821 Sq Ft

    2829 Aloma Ave, Winter Park, FL 32792

    Under contract-accepting backup offers. Under contract but accepting back up offers – 2829 Aloma Avenue, Winter Park This is the one you’ve been waiting for. A completely remodeled home with a private pool in one of the most desirable areas of Central Florida—all for under $600,000. Enjoy the perfect blend of modern upgrades and unbeatable location, just minutes from top-rated restaurants,

    Roberto Silva LPT REALTY, LLC

    2829 Aloma Ave, Winter Park, FL 32792
  • /17

    $2,510 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,397 Sq Ft
    • Townhouse for Rent

    1839 Blaine Terrace, Winter Park, FL 32792

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

    1839 Blaine Terrace, Winter Park, FL 32792
  • /2

    $3,100,000

    Sold Jun 27, 2025

    731 Williams Dr, Winter Park, FL 32789

    • 5 Beds
    • 6 Baths
    • 4,260 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $728/SF
    • 45 Days On Market

    Current Estimated Value $2,885,321

    Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

    731 Williams Dr, Winter Park, FL 32789
    • /2

      Not Listed For Sale

      3000 George Mason Ave Unit 1, Winter Park, FL 32792

      • 2 Beds
      • 2.5 Baths
      • 1,108 Sq Ft
      • Built 1974
      3000 George Mason Ave Unit 1, Winter Park, FL 32792

      Last Sold Summary

      • 58 Days On Market

  • /33

    $450,000

    $50K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 2,117 Sq Ft

    1923 Linden Rd, Winter Park, FL 32792

    ***WINTER PARK **** 4 BEDROOMS ****3 BATHROOM **** PAID OFF SOLAR ***** WILL HELP BUYER****METAL ROOF ***1/3 ACRE*** Welcome to 1923 Linden Rd, Winter Park—a well-maintained single-story residence offering space, character, and an exceptional location. Built in 1955, this solid masonry and concrete block home features 4 bedrooms, 3 full bathrooms, and approximately 2,117 heated square feet, with

    Milton James COLDWELL BANKER REALTY

    1923 Linden Rd, Winter Park, FL 32792
  • /20

    $2,375 Per Month

    • 3 Beds
    • 2 Baths
    • 1,455 Sq Ft
    • House for Rent

    7523 Dockside St, Winter Park, FL 32792

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2519.90. That covers your base rent, $2375.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    7523 Dockside St, Winter Park, FL 32792
  • /2

    $2,700,000

    Sold Oct 02, 2025

    1445 Holts Grove Cir, Winter Park, FL 32789

    • 5 Beds
    • 5 Baths
    • 4,489 Sq Ft
    • Built 2002

    Last Sold Summary

    • 2% Above List Price
    • $601/SF
    • 2 Days On Market

    Current Estimated Value $2,704,546

    Last Listing Agent Shelley Heistand PREMIER SOTHEBY'S INTL. REALTY

    1445 Holts Grove Cir, Winter Park, FL 32789
    • /2

      Est $281,495

      Not Listed For Sale

      218 Balfour Dr Unit 12, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,256 Sq Ft
      • Built 1985
      218 Balfour Dr Unit 12, Winter Park, FL 32792

      Last Sold Summary

      • 19 Days On Market

  • /8

    $849,000

    $49K PRICE INCREASE
    • 4 Beds
    • 2 Baths
    • 1,617 Sq Ft

    1780 Bryan Ave, Winter Park, FL 32789

    Build your dream home in one of Winter Park’s most desirable locations. This 66.6’ x 127’ homesite at 1780 Bryan Avenue offers a rare opportunity to secure the last remaining lot of three consecutive new construction parcels. Surrounded by newly built luxury residences, the property provides a clean slate for custom design while maintaining strong future value.The lot’s generous dimensions

    Nickolas McKee KELLER WILLIAMS WINTER PARK

    1780 Bryan Ave, Winter Park, FL 32789
  • /20

    $2,445 Per Month

    • 3 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • House for Rent

    2313 Dunbury Ct, Winter Park, FL 32792

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2589.90. That covers your base rent, $2445.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    2313 Dunbury Ct, Winter Park, FL 32792
  • /2

    $375,000

    Sold Dec 30, 2025

    3083 Crane Strand Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1972

    Last Sold Summary

    • $312/SF
    • 12 Days On Market

    Current Estimated Value $372,440

    Last Listing Agent Sheri Malin REDFIN CORPORATION

    3083 Crane Strand Dr, Winter Park, FL 32792
    • /2

      Est $304,301

      Not Listed For Sale

      311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

      • 1 Bed
      • 1 Bath
      • 482 Sq Ft
      • Built 1960
      311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

      Last Sold Summary

      • 3 Days On Market

  • /18

    $269,000

    $16K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft

    3220 Netherwood Dr, Winter Park, FL 32792

    Under contract-accepting backup offers. Welcome home to this fully renovated 2-bedroom, 1.5-bath residence! This home features a brand-new kitchen, new flooring throughout, and beautifully updated bathrooms. Nestled in a quiet neighborhood, it offers a large backyard—perfect for outdoor entertaining or future expansion. Ideal for a first-time homebuyer or anyone seeking stress-free living. Best

    Nimrah Ashraf THE FIRM RE

    3220 Netherwood Dr, Winter Park, FL 32792
  • /13

    $1,275

    Total Monthly Price

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

    2037 Linden Rd Unit 2037 linden rd unit A, Winter Park, FL 32792

    Mother in law suite 1 bd /1 bath 613 Sqf Nice neighborhood, washer and dryer. Parking Garage Cable, internet, Electricity. Include in the rent Not Smoking. Small pet. Cat. Independent Entrance Door

    2037 Linden Rd Unit 2037 linden rd unit A, Winter Park, FL 32792
  • /2

    $560,000

    Sold Aug 20, 2025

    1901 Loch Berry Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,420 Sq Ft
    • Built 1957

    Last Sold Summary

    • 1% Below List Price
    • $394/SF
    • 7 Days On Market

    Current Estimated Value $550,150

    Last Listing Agent Monica Tipirneni FOLIO REALTY LLC

    1901 Loch Berry Rd, Winter Park, FL 32792
    • /2

      Est $320,995

      Not Listed For Sale

      3251 Crown Jewel Ct, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,408 Sq Ft
      • Built 2019
      3251 Crown Jewel Ct, Winter Park, FL 32792

      Last Sold Summary

      • 6 Days On Market

  • /47

    $617,500

    $18K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,785 Sq Ft

    2708 Lion Heart Rd, Winter Park, FL 32792

    Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning

    Navid Rokh EQUITYPRO LLC

    2708 Lion Heart Rd, Winter Park, FL 32792
  • /24

    $1,150

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,165 Sq Ft
    • Condo for Rent

    200 Saint Andrews Blvd Unit 2402, Winter Park, FL 32792

    Looking for a co-tenant. Four Seasons offers walkability that many Winter Park addresses simply don’t. You’re steps from the scenic Cady Way Trail and Ward Park. A short stroll takes you to Publix, Sprouts Farmers Market, Starbucks, and Panera Bread. Historic Park Avenue with its boutiques, restaurants, and charm is just five minutes by car. AdventHealth Winter Park and the Center for Health

    200 Saint Andrews Blvd Unit 2402, Winter Park, FL 32792
  • /2

    $916,000

    Sold Jul 17, 2025

    609 Langholm Dr, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 1,981 Sq Ft
    • Built 1960

    Last Sold Summary

    • 4% Below List Price
    • $462/SF
    • 8 Days On Market

    Current Estimated Value $911,312

    Last Listing Agent Jason Shore JMO REAL ESTATE GROUP

    609 Langholm Dr, Winter Park, FL 32789
    • /2

      Not Listed For Sale

      2609 Holly Rd Unit 2611, Winter Park, FL 32792

      • 4 Beds
      • 4 Baths
      • 2,382 Sq Ft
      • Built 1972
      2609 Holly Rd Unit 2611, Winter Park, FL 32792

      Last Sold Summary

      • 7 Days On Market

  • /48

    $4,200,000

    • Land
    • 14,810 Sq Ft
    • $12,352,941 per Acre

    1298 Beachview Ave, Winter Park, FL 32789

    This is a rare Lake Killarney portfolio offering of four parcels in Winter Park. An exceptional opportunity to acquire a four-parcel assemblage in one of Winter Park’s most coveted locations, just moments from the shores of Lake Killarney. This offering includes 1321 Fairview Ave. and 230 and 240 Killarney Drive, all with potential for private dock access, and a desirable live/work parcel on 1298

    Shandy Ortiz PREMIER SOTHEBYS INT'L REALTY

    1298 Beachview Ave, Winter Park, FL 32789
  • /12

    $2,950

    Total Monthly Price

    • 3 Beds
    • 3.5 Baths
    • 1,400 Sq Ft
    • Townhouse for Rent

    223 Sandlewood Trail, Winter Park, FL 32789

    The townhouse has been renovated, including updates to the kitchen with modern countertops, cabinetry, and stainless steel appliances. The bathrooms are renovated with updated vanities, fixtures, and finishes. Includes community pool access and directly behind the property is a recreational area offering various amenities.

    223 Sandlewood Trail, Winter Park, FL 32789
  • /2

    $660,000

    Sold Nov 17, 2025

    2421 Summerfield Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,256 Sq Ft
    • Built 1968

    Last Sold Summary

    • 2% Above List Price
    • $293/SF
    • 6 Days On Market

    Current Estimated Value $669,556

    Last Listing Agent Simi Lakhani KELLER WILLIAMS CLASSIC

    2421 Summerfield Rd, Winter Park, FL 32792
    • /2

      Not Listed For Sale

      104 Moyses Rd, Winter Park, FL 32792

      • 4 Beds
      • 4 Baths
      • 1,872 Sq Ft
      • Built 1985
      104 Moyses Rd, Winter Park, FL 32792

      Last Sold Summary

      • 43 Days On Market

  • /2

    $999,000

    $51K PRICE DROP
    • Land
    • 11,325 Sq Ft
    • $3,842,308 per Acre

    1836 Grinnell Terrace, Winter Park, FL 32789

    Opportunity to build your dream home in gorgeous Winter Park. This large lot includes a 3 bedroom 2 bath updated home. With a lot comprising 140 x 78 (11,305 square feet) there is plenty of room for a pool. Live in the house while you make your future plans!

    Cindy Kuykendall FANNIE HILLMAN & ASSOCIATES

    1836 Grinnell Terrace, Winter Park, FL 32789
  • /12

    $1,300

    Total Monthly Price

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

    1360 Formosa Ave Unit 1360 Formosa, Winter Park, FL 32789

    Centrally located 2/1 apartment. Near Shopping, gas, churches, golf, convenience store, park and much more. Across the street is Orlando. Hardwood floors. Over 100 restaurants within 1 mile. Easy on and off I-4. Good neighbors. No pets.

    1360 Formosa Ave Unit 1360 Formosa, Winter Park, FL 32789
  • /2

    $610,000

    Sold Jun 12, 2026

    1174 Wildmeadow Run, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,770 Sq Ft
    • Built 2021

    Last Sold Summary

    • 9% Below List Price
    • $345/SF
    • 54 Days On Market

    Current Estimated Value $647,112

    Last Listing Agent Kara Lushear COLDWELL BANKER REALTY

    1174 Wildmeadow Run, Winter Park, FL 32792
    • /2

      Est $461,471

      Not Listed For Sale

      1323 Merrydale Way, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,964 Sq Ft
      • Built 2021
      1323 Merrydale Way, Winter Park, FL 32792

      Last Sold Summary

      • 98 Days On Market

Showing Results 201 - 240, Page 6 of 18

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