Winter Park, FL Homes

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  $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 OAKSTRAND REALTY

  3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792
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  /35

  $1,290 - $2,105 per month

  Venue At Winter Park

  1 - 3 Beds

  5 Autumn Breeze Way, Winter Park, FL 32792

  Come home to Venue—a community nestled in the heart of Winter Park. Venue is designed to make your living experience better than it has ever been before.When it comes to finding the perfect floor plan for your lifestyle, we have you covered. Choose from our newly renovated 1, 2, and 3-bedroom residences offering refined interior finishes and premier features that are sure to fit all of your

  5 Autumn Breeze Way, Winter Park, FL 32792
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  $399,900 Sold Oct 08, 2025

  7553 Laurel Springs Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Built 1973

  Last Sold Summary

  • $338/SF
  • 20 Days On Market

  Current Estimated Value $395,777

  Last Listing Agent Yamila Lopez EMPIRE NETWORK REALTY

  7553 Laurel Springs Dr, Winter Park, FL 32792
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  /20

  Est $243,012 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 968 Sq Ft

  5498 Peaco Place, Winter Park, FL 32792

  5498 Peaco Place, Winter Park, FL 32792
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  /5

  $5,000

  • 4 Beds
  • 2 Baths
  • 1,979 Sq Ft

  3949 Cool Water Ct, Winter Park, FL 32792

  Foreclosure Auction Ends February 10, 2026 at 11:00 AM. Discover this inviting 4-bedroom, 2-bathroom single-family home, offering a wonderful opportunity to live in the desirable Winter Park community. The list price is the opening bid for the online auction. Sold As-is. Explore more details and submit your bid through Federa Home App.

  Jamie Boone Jamie L Boone LLC

  3949 Cool Water Ct, Winter Park, FL 32792
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  /33

  $2,400 per month

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft
  • Townhouse for Rent

  7522 Aloma Pines Ct, Winter Park, FL 32792

  Beautifully maintained 3-bedroom, 2.5-bath two-story townhome featuring an open and functional floor plan. Tile flooring throughout the first-floor living areas, kitchen, dining space,half bathroom, and interior utility room. The kitchen features granite countertops, ample cabinetry, a large center island, a walk-in pantry, and a full appliance package, including a washer and dryer. Sliding glass

  Vildan Nigro RIVA REALTY GROUP LLC

  7522 Aloma Pines Ct, Winter Park, FL 32792
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  /2

  $420,000 Sold Jan 15, 2026

  1847 Azalea Ave, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 1,477 Sq Ft
  • Built 1961

  Last Sold Summary

  • $284/SF
  • 1 Day On Market

  Last Listing Agent Trace Christian, III COLDWELL BANKER REALTY

  1847 Azalea Ave, Winter Park, FL 32789
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  /30

  Est $738,648 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,682 Sq Ft

  311 E Morse Blvd Unit 4-4, Winter Park, FL 32789

  311 E Morse Blvd Unit 4-4, Winter Park, FL 32789
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  /28

  $570,000

  • 4 Beds
  • 3 Baths
  • 1,526 Sq Ft

  731 Bongart Rd, Winter Park, FL 32792

  Experience luxury living in this stunning, remodeled single-family home located in the heart of Winter Park. This spectacular residence features four spacious bedrooms and three modern bathrooms, boasting sleek laminate flooring throughout. The chef-inspired kitchen comes fully equipped with premium stainless steel appliances, while the massive backyard and sparkling pool provide an ideal setting

  Maria Gomez Arevalo MY REALTY GROUP, LLC.

  731 Bongart Rd, Winter Park, FL 32792
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  /27

  $1,236 - $2,425 per month

  Village Park Senior

  1 - 3 Beds

  550 W Denning Dr, Winter Park, FL 32789

  WINTER PARK VILLAGE, an established lifestyle center located just north of Orlando in the affluent community of Winter Park on 17-92 between Lee Road and Fairbanks Avenue. This is the area’s most exciting destination for upscale shopping, dining, entertainment and just an overall great place to spend time away from the mall madness.

  550 W Denning Dr, Winter Park, FL 32789
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  /2

  $199,900 Sold Nov 03, 2025

  2500 Lee Rd Unit 134, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Built 1969

  Last Sold Summary

  • 5% Below List Price
  • $310/SF
  • 130 Days On Market

  Current Estimated Value $192,996

  Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

  2500 Lee Rd Unit 134, Winter Park, FL 32789
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  /30

  Est $1,335,830 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,734 Sq Ft

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789
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  /18

  $285,000

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft

  3220 Netherwood Dr, Winter Park, FL 32792

  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 of all, NO HOA! Conveniently located near

  Nimrah Ashraf THE FIRM RE

  3220 Netherwood Dr, Winter Park, FL 32792
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  /50

  $3,150 per month

  • 3 Beds
  • 2 Baths
  • 1,436 Sq Ft
  • House for Rent

  1835 Edwin Blvd, Winter Park, FL 32789

  Charming bungalow on a brick street in beautiful Winter Park, available January 12, 2026. This 3-bedroom, 2-bathhome offers a great split floorplan and newer finishes. The kitchen and both primary en-suite and secondary bathroomshave been completely remodeled with premium finishes. The home boasts a newer roof, hardwood and stone floorsthroughout, with granite counters, white

  Vincent Scarlatos CORCORAN PREMIER REALTY

  1835 Edwin Blvd, Winter Park, FL 32789
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  /19

  $172,000 Sold May 23, 2025

  700 Melrose Ave Unit E24, Winter Park, FL 32789

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

  Last Sold Summary

  • 14% Below List Price
  • $219/SF
  • 164 Days On Market

  Current Estimated Value $181,870

  Last Listing Agent Susan Dering HOMEVEST REALTY

  700 Melrose Ave Unit E24, Winter Park, FL 32789
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  /2

  Est $857,498 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,610 Sq Ft

  1245 Wisconsin Ave, Winter Park, FL 32789

  1245 Wisconsin Ave, Winter Park, FL 32789
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  /28

  $145,000

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 243, Winter Park, FL 32789

  Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living

  Sue Gilman KELLER WILLIAMS WINTER PARK

  2500 Lee Rd Unit 243, Winter Park, FL 32789
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  /35

  $976 - $1,373 per month

  Golden Oaks

  2 - 3 Beds

  7701 Acorn Woods Cir, Winter Park, FL 32792

  Golden Oaks Apartments is your destination for quality, affordable living, offering spacious two and three-bedroom apartment options designed to meet your needs. Located in a serene, peaceful area, our community combines the tranquility of a residential neighborhood with the convenience of nearby shopping, dining, and entertainment. With income restrictions in place to ensure affordability,

  7701 Acorn Woods Cir, Winter Park, FL 32792
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  /2

  $266,000 Sold Nov 19, 2025

  1500 Gay Rd Unit 9B, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $259/SF
  • 5 Days On Market

  Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 9B, Winter Park, FL 32789
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  /36

  Est $189,126 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft

  2935 Antique Oaks Cir Unit 62, Winter Park, FL 32792

  2935 Antique Oaks Cir Unit 62, Winter Park, FL 32792
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  /32

  $949,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,160 Sq Ft

  1929 S Lakemont Ave, Winter Park, FL 32792

  This modern Winter Park townhome sits in a quiet pocket between Lake Spier and Lake Compton, offering a rare mix of style, comfort, and convenience. This home feels tucked away while still keeping you close to everything you love about Winter and Baldwin Park. Inside, the layout is open and easy to live in. The kitchen features stone countertops, stainless steel appliances, and a large island

  Brandon Geers COMPASS FLORIDA LLC

  1929 S Lakemont Ave, Winter Park, FL 32792
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  /27

  $4,495 per month

  • 3 Beds
  • 2.5 Baths
  • 2,317 Sq Ft
  • Townhouse for Rent

  438 W Swoope Ave, Winter Park, FL 32789

  $4495.00 for a 15 MO LEASE$4695.00 12 MO LEASE Nestled within the exclusive 400 West enclave intimate community of just nine residences, just moments from Park Avenue this modern townhome seamlessly combines superior craftsmanship, elegant interiors, and outstanding walkability. Entering through either the private garage or the charming garden-style front path, you're welcomed into a

  Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

  438 W Swoope Ave, Winter Park, FL 32789
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  /2

  $600,000 Sold Apr 10, 2025

  7531 Lodge Pole Trail, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,141 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $280/SF
  • 20 Days On Market

  Current Estimated Value $582,782

  Last Listing Agent Austin Cummings NEXTDWELL

  7531 Lodge Pole Trail, Winter Park, FL 32792
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  /2

  Est $141,181 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  289 Lewfield Cir, Winter Park, FL 32792

  289 Lewfield Cir, Winter Park, FL 32792
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  /36

  $424,000

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2834 Bright Bird Ln, Winter Park, FL 32792

  Preferred Lender rate Incentives available. This beautifully maintained 3-bedroom, 2.5-bath townhome with a one-car garage, located in a newly gated community that offers comfort, style, and convenience. The home features ambient high-hat lighting throughout, creating a warm and modern atmosphere. The spacious kitchen is ideal for everyday living and entertaining, while the open living area is

  Irene Navarro LIFESTYLE INTERNATIONAL REALTY

  2834 Bright Bird Ln, Winter Park, FL 32792
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  /24

  $1,258 - $3,052 per month

  Alvista Winter Park

  1 - 2 Beds

  3935 Sutton Place Blvd, Winter Park, FL 32792

  Live life better at Alvista Winter Park! Located in the sought-after neighborhood of Winter Park, Orlando, and just minutes from Full Sail University, Harbor Park and Winter Pines Golf Club, our community effortlessly blends the concepts of convenience and ease. Our collection of lifestyle amenities and interior details make our residents quickly feel right at home!Choose from spacious one and

  3935 Sutton Place Blvd, Winter Park, FL 32792
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  /2

  $470,000 Sold Jan 15, 2026

  3319 Ellwood Ct, Winter Park, FL 32792

  • 5 Beds
  • 3 Baths
  • 1,546 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $304/SF
  • 78 Days On Market

  Last Listing Agent Elena Sanchez BALDWIN PARK REALTY LLC

  3319 Ellwood Ct, Winter Park, FL 32792
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  /39

  Est $223,972 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,300 Sq Ft

  220 Lewfield Cir, Winter Park, FL 32792

  220 Lewfield Cir, Winter Park, FL 32792
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  /47

  $1,199,000

  • 3 Beds
  • 2.5 Baths
  • 2,578 Sq Ft

  1541 Westchester Ave, Winter Park, FL 32789

  Set on over half an acre in Winter Park’s coveted Orwin Manor, this 1935 French Provincial estate offers a rare blend of architectural character, modern system updates, and extraordinary future potential. The property offers the unique opportunity to own an estate in a beautifully historic Winter Park neighborhood. Whether thoughtfully renovated, expanded, or reimagined, this property stands as a

  Lisa Gould KELLER WILLIAMS WINTER PARK

  1541 Westchester Ave, Winter Park, FL 32789
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  /15

  $1,350 per month

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

  1695 Lee Rd Unit B210, Winter Park, FL 32789

  This great second floor one bedroom 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and

  giuseppina moriconi GM SUNSHINE REALTY LLC

  1695 Lee Rd Unit B210, Winter Park, FL 32789
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  /2

  $245,900 Sold Aug 11, 2025

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 1,132 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $217/SF
  • 2 Days On Market

  Current Estimated Value $251,206

  Last Listing Agent Matt Merdian MERDIAN REALTY LLC

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789
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  /21

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft

  7340 Daniel Webster Dr Unit A, Winter Park, FL 32792

  7340 Daniel Webster Dr Unit A, Winter Park, FL 32792
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  /21

  $259,000

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 18A, Winter Park, FL 32789

  Lakefront Community on beautiful Lake Killarney. 2 Bedroom/2 Bath First Floor Unit with Courtyard And Lake Views. Lovingly updated and meticulously maintained. Kitchen has raised ceilings, Maple Cabinets and Granite Counters. Dining Room has matching Cabinets and Counters with pull-out Drawers for additional Storage. Tile Floors in Living Areas. New Carpets in both Bedrooms. Windows and Sliding

  Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 18A, Winter Park, FL 32789
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  /35

  $1,455 - $2,620 per month

  Stonecastle Apartment Homes

  1 - 3 Beds

  2015 New Stonecastle Terrace, Winter Park, FL 32792

  Stonecastle Apartments is the community you've been looking for in Winter Park, FL. With spacious one-, two-, and three-bedroom homes complete with in-home washers and dryers, stainless steel appliances, and smart thermostats, you're guaranteed to find a place to live with a lifestyle to love. What's more, as a member of the community you'll also have access to our fitness center, resident

  2015 New Stonecastle Terrace, Winter Park, FL 32792
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  /2

  $725,000 Sold May 13, 2025

  1570 Grove Terrace, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,663 Sq Ft
  • Built 1991

  Last Sold Summary

  • $436/SF

  Current Estimated Value $753,158

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

  1570 Grove Terrace, Winter Park, FL 32789
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  /24

  Est $189,863 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  200 Saint Andrews Blvd Unit 2210, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 2210, Winter Park, FL 32792
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  /17

  $195,000

  • 1 Bed
  • 1 Bath
  • 732 Sq Ft

  1500 Gay Rd Unit 5, Winter Park, FL 32789

  Welcome to Chateaux du Lac, a lakefront community in the heart of Winter Park, FL, offering an active and convenient lifestyle. Residents enjoy an impressive array of amenities including a heated community pool, clubhouse, lakefront community deck, BBQ area, resident-only boat ramp, community laundry facilities, and two on-site saunas. This second-floor one-bedroom, one-bath apartment features

  Jacob Hara TRANSCEND REALTY

  1500 Gay Rd Unit 5, Winter Park, FL 32789
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  /13

  $2,000 per month

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft
  • Townhouse for Rent

  200 Saint Andrews Blvd Unit 1805, Winter Park, FL 32792

  This condo offers the perfect blend of comfort and contemporary style. With 2 large bedrooms, 1 and a half bathrooms, and a range of brand new upgrades. As you step inside, you'll immediately notice the attention to detail and the modern finishes throughout. The full bath has been fully updated with real marble flooring. The half bath has also been upgraded and continues the LVF put in the

  Alexander Horton LIVE MVRK LLC

  200 Saint Andrews Blvd Unit 1805, Winter Park, FL 32792
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  /49

  $1,650,000 Sold Mar 12, 2025

  1781 Goodrich Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,701 Sq Ft
  • Built 2024

  Last Sold Summary

  • 15% Below List Price
  • $611/SF
  • 88 Days On Market

  Current Estimated Value $1,673,434

  Last Listing Agent Laura Hope COMPASS FLORIDA LLC

  1781 Goodrich Ave, Winter Park, FL 32789
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  /2

  Est $1,622,065 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,174 Sq Ft

  101 S New York Ave Unit 303, Winter Park, FL 32789

  101 S New York Ave Unit 303, Winter Park, FL 32789

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