28,301

Winter Park, FL Homes

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  • /31

    $389,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,252 Sq Ft

    7213 Silver Place, Winter Park, FL 32792

    Under contract-accepting backup offers. Welcome to this charming 3-bedroom, 2-bath home tucked away on a quiet cul-de-sac in the Oakcrest community of Winter Park. Offering 1,252 square feet of comfortable living space, this single-story ranch sits on a generously sized 0.22-acre lot that provides plenty of room to enjoy outdoor living, entertain guests, or create your own backyard retreat.

    Michael Rogers INNOVATIVE REALTY, LLC

    7213 Silver Place, Winter Park, FL 32792
  • /15

    $2,400 per month

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft
    • House for Rent

    3221 Thistle Hill Dr, Aloma, FL 32792

    This home is exclusively offered by Brandywine Homes USA on a first-come, first-approved basis until the lease is signed and the security deposit is paid. Rental Qualifications: Rental Fees: Security Deposit: Varies based on credit, with a standard deposit equal to 1 month's rent. Security Deposit Alternatives available - $150 fee (subject to approval).

    3221 Thistle Hill Dr, Aloma, FL 32792
  • /2

    $699,000 Sold Jun 30, 2025

    1632 Haven Dr, Orlando, FL 32803

    • 3 Beds
    • 2.5 Baths
    • 1,772 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $394/SF
    • 110 Days On Market

    Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

    1632 Haven Dr, Orlando, FL 32803
    • /2

      Not Listed For Sale

      677 Grenadine Ct Unit S, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,037 Sq Ft
      • Built 1981
      677 Grenadine Ct Unit S, Winter Park, FL 32792

      Last Sold Summary

      • $207/SF
      • 103 Days On Market

      Last Sold Price $215,000

      Last Listing Agent Barbara Zapotocky RE/MAX

  • /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
  • /20

    $1,600 per month

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

    2523 Alexa Ct, Winter Park, FL 32792

    Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard

    Joseph LaRosa LA ROSA REALTY LLC

    2523 Alexa Ct, Winter Park, FL 32792
  • /2

    $689,500 Sold Jul 19, 2025

    1129 Golfside Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • Built 1978

    Last Sold Summary

    • 5% Below List Price
    • $394/SF
    • 21 Days On Market

    Current Estimated Value $673,611

    Last Listing Agent Tess Muccigrosso RE/MAX 200 REALTY

    1129 Golfside Dr, Winter Park, FL 32792
    • /2

      Est $246,617 Not Listed For Sale

      7164 Swallow Run Unit GE, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,470 Sq Ft
      • Built 2012
      7164 Swallow Run Unit GE, Winter Park, FL 32792

      Last Sold Summary

      • 15% Below List Price
      • $197/SF
      • 13 Days On Market

      Last Sold Price $290,000

      Last Listing Agent Christian Cruz Garayua CENTURY 21 NEXT LEVEL REALTY

  • /33

    $150,000

    • 1 Bed
    • 1 Bath
    • 749 Sq Ft

    2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792

    Welcome to this bright and cozy 1-bedroom, 1-bathroom corner unit located in the highly desirable Winter Park area of Orlando. This well-maintained condo features ceramic tile flooring throughout, a spacious walk-in closet in the master bedroom, a laundry closet with washer and dryer included, and modern light fixtures. Enjoy the outdoors on your very nice private balcony, and take advantage of

    SANTIAGO SILVA THE PAMPAS REAL ESTATE GROUP, LLC.

    2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792
  • /11

    $1,380 per month

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

    2942 Antique Oaks Cir Unit 82, Winter Park, FL 32792

    Property Id: 1010517Second Floor one bedroom unit in the highly desirable Parkview Condominium Complex across from Full Sail University. The rent includes water and sewer. All floors are laminate.

    2942 Antique Oaks Cir Unit 82, 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 $885,674

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

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

      Not Listed For Sale

      681 Grenadine Ct Unit S, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,037 Sq Ft
      • Built 1981
      681 Grenadine Ct Unit S, Winter Park, FL 32792

      Last Sold Summary

      • $191/SF
      • 147 Days On Market

      Last Sold Price $198,000

      Last Listing Agent Reinaldo Roman ROMAN'S PRO REALTY LLC

  • /52

    $180,000

    • 1 Bed
    • 1 Bath
    • 727 Sq Ft

    200 Saint Andrews Blvd Unit 705, Winter Park, FL 32792

    This isn’t your average condo. It’s professionally updated with large rooms and more closet space than you’ll know what to do with. There’s even a washer and dryer right in the unit (no more laundry runs!), newer appliances, and parking right outside your door. On a scale from 1 to 10, this place is easily a TWENTY! Seriously, no expense was spared to make it super comfortable. You’ll love the

    Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

    200 Saint Andrews Blvd Unit 705, Winter Park, FL 32792
  • /38

    $2,600 per month

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft
    • Townhouse for Rent

    1994 Canny Cove, Winter Park, FL 32792

    This beautiful three bedroom, two and a half bath townhome is located in the newly developed Grayson Square, a gated community in Winter Park. High-speed Internet and cable are included. There are no rear neighbors, so you will enjoy relaxing on your back porch with a beautiful water view. As you enter the home, the entrance leads to the large kitchen and living area. The kitchen features

    Vildan Nigro RIVA REALTY GROUP LLC

    1994 Canny Cove, Winter Park, FL 32792
  • /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 $940,446

    Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

    4107 Gabriella Ln, Winter Park, FL 32792
    • /33

      Est $469,917 Not Listed For Sale

      2260 Shadowland Loop, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 2,308 Sq Ft
      • Built 2021
      2260 Shadowland Loop, Winter Park, FL 32792

      Last Sold Summary

      • $204/SF
      • 2 Days On Market

      Last Sold Price $470,000

      Last Listing Agent Jennifer Grimes ERA GRIZZARD REAL ESTATE

  • /27

    $145,000

    • 2 Beds
    • 2.5 Baths
    • 1,090 Sq Ft

    3021 Aaron Burr Ave Unit 3, Winter Park, FL 32792

    Townhouse 2 bedroom 2.5 bath, both bathrooms on the second floor are remodeled. The Townhome is rent $1,600. The unit is located in Winter Park Area and is close to the shopping and dining. It is also close to public transportation. HOME GUARANTY OF AMERICA HWA 13 MONTH INCLUDED.

    Daiana Garcia Medrano LA ROSA REALTY ORLANDO LLC

    3021 Aaron Burr Ave Unit 3, Winter Park, FL 32792
  • /17

    $2,625 per month

    • 3 Beds
    • 2 Baths
    • 1,530 Sq Ft
    • House for Rent

    6877 Jackman Blvd, 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 $2769.90. That covers your base rent, $2625.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    6877 Jackman Blvd, Winter Park, FL 32792
  • /2

    $380,000 Sold Mar 27, 2025

    3877 Waterview Loop, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,527 Sq Ft
    • Built 1988

    Last Sold Summary

    • $249/SF

    Current Estimated Value $376,728

    Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

    3877 Waterview Loop, Winter Park, FL 32792
    • /2

      Not Listed For Sale

      0 Grand Rd Unit MFRO6213919, Winter Park, FL 32792

      0 Grand Rd Unit MFRO6213919, Winter Park, FL 32792

      Last Sold Summary

      • 55 Days On Market

      Last Sold Price $635,000

      Last Listing Agent Marcella Mineo MARGAUX REALTY INC

  • /14

    $2,289,000 Pending

    • 5 Beds
    • 4.5 Baths
    • 3,334 Sq Ft

    2722 Eastern Pkwy, Winter Park, FL 32789

    Under contract-accepting backup offers. Under Construction. Masterfully designed new construction by LUIH Luxury Homes, where architectural elegance and refined livability meet an unbeatable lifestyle. Located in the Audubon Park School District just a short stroll from the iconic East End Market. From its captivating façade to its meticulously curated interiors, every element of this residence

    Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    2722 Eastern Pkwy, Winter Park, FL 32789
  • /24

    $1,650 per month

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

    1695 Lee Rd Unit C216, Winter Park, FL 32789

    Available for immediate move-in, this comfortable second-floor corner condo offers a peaceful setting with playground and pool views. The home features a fully carpeted interior, a spacious kitchen with a pantry closet, and a newer refrigerator. Washer and dryer are included for added convenience. Great balcony for relaxing on the cooler Florida days! Located in desirable Winter Park, you'll

    Yarmmys Vargas ZEN LIVING HOMES LLC

    1695 Lee Rd Unit C216, Winter Park, FL 32789
  • /2

    $396,477 Sold May 20, 2025

    7543 Dockside St, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,434 Sq Ft
    • Built 1973

    Last Sold Summary

    • 3% Above List Price
    • $276/SF
    • 7 Days On Market

    Current Estimated Value $389,650

    Last Listing Agent Juan Matias LPT REALTY, LLC

    7543 Dockside St, Winter Park, FL 32792
    • /2

      Est $685,980 Not Listed For Sale

      1360 Blue Stem Ln, Winter Park, FL 32792

      • 4 Beds
      • 2.5 Baths
      • 2,416 Sq Ft
      • Built 2021
      1360 Blue Stem Ln, Winter Park, FL 32792

      Last Sold Summary

      • 1% Above List Price
      • $281/SF
      • 8 Days On Market

      Last Sold Price $680,000

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

  • /32

    $144,000

    • 1 Bed
    • 1 Bath
    • 678 Sq Ft

    291 Lewfield Cir Unit 291, Winter Park, FL 32792

    One of the best views in this community. Enjoy easy living in this cozy, open-concept first-floor condo located in a desirable Winter Park community. Step out onto your newly screened-in patio and take in the peaceful, park-like setting — a relaxing extension of your living space and the perfect spot for morning coffee or evening unwinding. Recent 2025 improvements include a new A/C system, water

    Barbara Coy WATSON REALTY CORP

    291 Lewfield Cir Unit 291, Winter Park, FL 32792
  • /20

    $1,650 per month

    • 1 Bed
    • 1 Bath
    • 502 Sq Ft
    • House for Rent

    1550 Michigan Ave, Winter Park, FL 32789

    Welcome to your future home in the charming district of Winter Park, FL! This inviting property offers a warm atmosphere perfect for relaxation and convenience, surrounded by a vibrant community.This residence boasts spacious living equipped with essential comforts. With ample bedrooms and bathrooms, it accommodates various lifestyles. You'll appreciate the central heating and cooling

    1550 Michigan Ave, Winter Park, FL 32789
  • /2

    $3,020,000 Sold Oct 02, 2025

    1820 Englewood Rd, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 4,263 Sq Ft
    • Built 2015

    Last Sold Summary

    • 8% Below List Price
    • $708/SF
    • 70 Days On Market

    Current Estimated Value $3,022,056

    Last Listing Agent David Hung KELLER WILLIAMS ADVANTAGE III

    1820 Englewood Rd, Winter Park, FL 32789
    • /2

      Est $150,908 Not Listed For Sale

      160 Lewfield Cir Unit 160, Winter Park, FL 32792

      • 1 Bed
      • 1 Bath
      • 678 Sq Ft
      • Built 1973
      160 Lewfield Cir Unit 160, Winter Park, FL 32792

      Last Sold Summary

      • 11% Below List Price
      • $249/SF
      • 18 Days On Market

      Last Sold Price $169,000

      Last Listing Agent Luis Cancel GLOBAL BROKERS RLTY OF FLORIDA

  • /7

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,104 Sq Ft

    Unlisted Address

    One or more photo(s) has been virtually staged Move-in ready 3-bedroom, 2-bath home in desirable Winter Park with recent interior updates. The home has been freshly painted throughout and features an updated kitchen with new cabinets and quartz countertops, creating a modern and inviting space.The functional layout offers comfortable living areas along with a screened patio, perfect for

    Rosa Rivera SKINNER REALTY, INC.

    Unlisted Address
  • /14

    $1,395 per month

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

    3651 N Goldenrod Rd Unit 204, Winter Park, FL 32792

    This is a 2 bedroom, 2 bathroom, second floor condo in the Lancelot at Winter Park community near local shops, restaurants, and schools. Features include a spacious main living area, a lovely kitchen, vaulted ceilings, spacious bedrooms, and a laundry closet. Community amenities include a pool, gym, and clubhouse. Schedule a showing or submit an application online. All Real Property Management &

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    3651 N Goldenrod Rd Unit 204, Winter Park, FL 32792
  • /2

    $1,120,000 Sold Jan 08, 2026

    5236 Lake Howell Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 3,710 Sq Ft
    • Built 2025

    Last Sold Summary

    • 23% Below List Price
    • $302/SF
    • 129 Days On Market

    Current Estimated Value $1,066,080

    Last Listing Agent Troy Hensley BHHS FLORIDA REALTY

    5236 Lake Howell Rd, Winter Park, FL 32792
    • /2

      Est $444,795 Not Listed For Sale

      2953 Clever Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2024
      2953 Clever Ln, Winter Park, FL 32792

      Last Sold Summary

      • 5% Below List Price
      • $246/SF
      • 7 Days On Market

      Last Sold Price $469,190

      Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

  • /75

    $3,055,000

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

    151 Oakwood Way, Winter Park, FL 32789

    Welcome to 151 Oakwood Way. This is a rare Winter Park showpiece by LunDev Custom Homes, tucked on a quiet, tree-lined street in the heart of Winter Park. This newer luxury pool home delivers the perfect blend of timeless architecture and modern comfort, pairing clean transitional design with warm, high-end selections and true Florida indoor/outdoor living. Inside, a bright open-concept floor

    Matthew Burks CORCORAN PREMIER REALTY

    151 Oakwood Way, Winter Park, FL 32789
  • /16

    $2,230 per month

    • 3 Beds
    • 2 Baths
    • 1,305 Sq Ft
    • House for Rent

    5484 Park Vale Blvd, 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.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

    5484 Park Vale Blvd, Winter Park, FL 32792
  • /2

    $799,000 Sold Apr 30, 2025

    2320 Janice Ave, Winter Park, FL 32789

    • Land
    • 0.28 Acre
    • $2,853,571 per Acre

    Last Sold Summary

    • 2 Days On Market

    Current Estimated Value $793,000

    Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES

    2320 Janice Ave, Winter Park, FL 32789
    • /18

      Est $181,178 Not Listed For Sale

      3351 River View Way Unit 41, Winter Park, FL 32792

      • 2 Beds
      • 1.5 Baths
      • 990 Sq Ft
      • Built 1983
      3351 River View Way Unit 41, Winter Park, FL 32792

      Last Sold Summary

      • 21% Below List Price
      • $231/SF
      • 53 Days On Market

      Last Sold Price $229,000

      Last Listing Agent My Hien Domeika Coldwell Banker Realty

  • /55

    $1,329,950

    • 4 Beds
    • 4 Baths
    • 3,474 Sq Ft

    952 Moss Ln, Winter Park, FL 32789

    Back on market at no fault of the seller! Brand new Roof and HVAC systems 2025. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 3-bathroom home exudes warmth and sophistication, creating an inviting haven for discerning buyers. Sunlight floods every room, highlighting the home’s

    Terry Connors THE SHOP REAL ESTATE CO.

    952 Moss Ln, Winter Park, FL 32789
  • /19

    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,113 Sq Ft
    • House for Rent

    1931 Carrigan Ave, Winter Park, FL 32792

    An excellent place to call home. This newly renovated 3 bedroom 2 bath house offers a lot of entertainment options; it is sitting on an oversize lot which features ample backyard space which is completely fenced. This home has brand new AC, Plumbing and Electric and offers washer/dryer hookups. Close to A+ schools and is approximately 7 minutes from Park Ave shopping and dining. This will not

    Amanda Beckman RED DOOR INVESTMENT GRP LLC

    1931 Carrigan Ave, Winter Park, FL 32792
  • /2

    $235,000 Sold Apr 29, 2025

    2529 Leeward Way, Winter Park, FL 32792

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft
    • Built 1977

    Last Sold Summary

    • $258/SF
    • 26 Days On Market

    Current Estimated Value $231,692

    Last Listing Agent Chris Creegan CREEGAN GROUP

    2529 Leeward Way, Winter Park, FL 32792
    • /42

      Est $482,388 Not Listed For Sale

      2444 Firstlight Way, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 2,376 Sq Ft
      • Built 2020
      2444 Firstlight Way, Winter Park, FL 32792

      Last Sold Summary

      • 1% Below List Price
      • $204/SF
      • 11 Days On Market

      Last Sold Price $485,000

      Last Listing Agent Patrick Pixley THE AGENCY FL

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