Winter Park, FL Homes

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  $80,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft

  304 Scottsdale Square Unit L304, Winter Park, FL 32792

  Two bedroom, 2 bathroom condo on second floor. Offers living room/dining room combination with exterior porch and laundry room.

  Laura Hilton CHARLES RUTENBERG REALTY ORLANDO

  304 Scottsdale Square Unit L304, Winter Park, FL 32792
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  /17

  $2,455 per month

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

  3363 Hamlet Loop, 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

  3363 Hamlet Loop, Winter Park, FL 32792
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  $1,206,400 Sold Oct 15, 2025

  4048 Gilder Rose Place, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 3,321 Sq Ft
  • Built 1992

  Last Sold Summary

  • $363/SF
  • 101 Days On Market

  Current Estimated Value $1,196,981

  Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

  4048 Gilder Rose Place, Winter Park, FL 32792
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  /2

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 525 Sq Ft

  3065 George Mason Ave Unit B, Winter Park, FL 32792

  3065 George Mason Ave Unit B, Winter Park, FL 32792
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  /27

  $127,400

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit E204, Winter Park, FL 32789

  Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom.

  Brandy Ray LOKATION

  1695 Lee Rd Unit E204, Winter Park, FL 32789
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  $7,000 per month

  • 4 Beds
  • 5 Baths
  • 3,302 Sq Ft
  • House for Rent

  519 Park North Ct, Winter Park, FL 32789

  Discover refined single-story living at 519 Park North Court, an exceptional luxury rental in the heart of Winter Park. This beautifully appointed four-bedroom, three-and-a-half-bath residence offers an ideal blend of elegance and comfort, with a thoughtfully designed split floor plan that ensures both privacy and functionality for modern living.The home welcomes you with a formal living room

  Kelly Price KELLY PRICE & COMPANY LLC

  519 Park North Ct, Winter Park, FL 32789
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  $72,000 Sold Jun 24, 2025

  273 Scottsdale Square Unit 273, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 785 Sq Ft
  • Built 1974

  Last Sold Summary

  • 24% Below List Price
  • $92/SF
  • 4 Days On Market

  Current Estimated Value $76,258

  Last Listing Agent Erin Tompkins COLDWELL BANKER RESIDENTIAL RE

  273 Scottsdale Square Unit 273, Winter Park, FL 32792
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  /2

  Est $210,482 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  608 Montego Bay Ct Unit S, Winter Park, FL 32792

  608 Montego Bay Ct Unit S, Winter Park, FL 32792
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  /69

  $1,675,000

  • 4 Beds
  • 2.5 Baths
  • 3,263 Sq Ft

  446 Alberta Dr, Winter Park, FL 32789

  Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only a mile stroll to the famous Park Ave shops, dining and entertaining. Home site over looks Lake Osceola and the multi million dollar homes all around!! A neighborhood lot, a few doors down, allows residents to have walking access to Lake

  Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  446 Alberta Dr, Winter Park, FL 32789
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  /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
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  $660,000 Sold May 23, 2025

  2732 Lion Heart Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,975 Sq Ft
  • Built 1962

  Last Sold Summary

  • $334/SF
  • 2 Days On Market

  Current Estimated Value $648,191

  Last Listing Agent Sue Grafton FANNIE HILLMAN & ASSOCIATES

  2732 Lion Heart Rd, Winter Park, FL 32792
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  /89

  Est $1,322,073 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft

  3629 Midiron Dr, Winter Park, FL 32789

  3629 Midiron Dr, Winter Park, FL 32789
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  /55

  $549,900

  • 2 Beds
  • 2.5 Baths
  • 1,428 Sq Ft

  630 Killarney Bay Ct Unit 3, Winter Park, FL 32789

  Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath, with a convenient half

  Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

  630 Killarney Bay Ct Unit 3, Winter Park, FL 32789
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  /30

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Condo for Rent

  650 Trinidad Ct Unit 650, Winter Park, FL 32792

  Welcome to your dream home in the heart of Winter Park, FL. This stunning Corner Unit 2-bedroom, 2-bathroom residence offers a perfect blend of comfort and style. The house is designed with a spacious layout that ensures ample natural light in every corner. The community amenities are sure to impress, with a sparkling pool, a well-equipped gym, and tennis courts available for your leisure and

  Dawn Slaughter TRUSTHOME PROPERTIES INC

  650 Trinidad Ct Unit 650, Winter Park, FL 32792
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  $685,000 Sold May 27, 2025

  1321 Medinah Ct, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,446 Sq Ft
  • Built 1979

  Last Sold Summary

  • 9% Below List Price
  • $280/SF
  • 53 Days On Market

  Current Estimated Value $684,074

  Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

  1321 Medinah Ct, Winter Park, FL 32792
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  Est $762,198 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,894 Sq Ft

  1477 Lone Feather Trail, Winter Park, FL 32792

  1477 Lone Feather Trail, Winter Park, FL 32792
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  /46

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,694 Sq Ft

  2152 Conifer Ave, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Price ENHANCEMENT! The best value in the area. Do not miss out on the opportunity to be the next owner of Conifer Avenue!This POOL home is amazing in every way and is truly a must see! Original Owner with incredible pride of ownership. Brand NEW Roof, Brand NEW Water Heater 2025, HVAC 2020, entire replumb and newer windows throughout. Nestled in

  Denise Korrey KORR REALTY CORP

  2152 Conifer Ave, Winter Park, FL 32792
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  /46

  $1,850 per month

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • Condo for Rent

  2918 Antique Oaks Cir Unit 31, Winter Park, FL 32792

  This beautifully updated, fully furnished two-bedroom, two-bath ground-floor condominium is available for lease in the highly desirable Parkview Village community in Winter Park. Designed for comfort, efficiency, and low-maintenance living, this move-in-ready home is ideal for professional residents.The open-concept floor plan features luxury vinyl plank flooring, granite countertops, and

  2918 Antique Oaks Cir Unit 31, Winter Park, FL 32792
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  $637,500 Sold Jan 16, 2026

  595 Huntington Ave Unit 4, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,951 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Below List Price
  • $327/SF
  • 149 Days On Market

  Last Listing Agent Andrew Livingston COLDWELL BANKER RESIDENTIAL RE

  595 Huntington Ave Unit 4, Winter Park, FL 32789
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  /2

  Est $203,004 Not Listed For Sale

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

  200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792
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  /99

  $5,495,000

  • 5 Beds
  • 6.5 Baths
  • 7,278 Sq Ft

  2211 Azalea Place, Winter Park, FL 32789

  Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Park’s most prestigious neighborhoods—just moments from the exclusive Winter Park Racquet Club. This extraordinary residence offers the perfect blend of timeless architecture, refined finishes, and state-of-the-art updates, all

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  2211 Azalea Place, Winter Park, FL 32789
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  /16

  $1,270 per month

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft
  • Townhouse for Rent

  2183 Crandon Ave Unit 1/2, Winter Park, FL 32789

  This 2 bedroom, 1 bathroom, 2nd floor unit is located in the heart of Winter Park. Enjoy all of Downtown Winter Park, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious living area, a lovely kitchen, a screened patio area, and a shared laundry room

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  2183 Crandon Ave Unit 1/2, Winter Park, FL 32789
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  $400,000 Sold May 29, 2025

  5144 Goldenrod Place Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Built 1972

  Last Sold Summary

  • 6% Below List Price
  • $273/SF
  • 36 Days On Market

  Current Estimated Value $403,244

  Last Listing Agent Rebecca Sparks C. APOLLO REALTY INC

  5144 Goldenrod Place Rd, Winter Park, FL 32792
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  /2

  Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,079 Sq Ft

  3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792

  3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792
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  /26

  $625,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,890 Sq Ft

  1360 Formosa Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Discover a rare and lucrative opportunity at 1360 Formosa Ave, a corner lot triplex in the highly sought-after Winter Park market. This income-generating property features three fully rented one-bedroom, one-bathroom units, providing a strong and steady return on investment. With 100% occupancy, this property is already a cash-flowing asset, but its

  Salvison Dickson TOP FLORIDA HOMES

  1360 Formosa Ave, Winter Park, FL 32789
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  /27

  $1,400 per month

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

  2500 Lee Rd Unit 212, Winter Park, FL 32789

  Welcome to Lakeside Manor on beautiful Lake Killarney! This charming 2 bedroom, 1 bathroom second-floor condo offers tranquil living in one of Central Florida’s most desirable areas. Enjoy a serene, park-like setting right outside your door and access to breathtaking sunset views from the private community dock.Just minutes from Park Ave, Rollins College, Mills District, top dining,

  2500 Lee Rd Unit 212, Winter Park, FL 32789
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  $1,250,000 Sold Dec 29, 2025

  359 Beloit Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,395 Sq Ft
  • Built 1979

  Last Sold Summary

  • $522/SF
  • 0 Days On Market

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  359 Beloit Ave, Winter Park, FL 32789
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  /2

  Est $430,885 Not Listed For Sale

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

  Unlisted Address

  Unlisted Address
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  /62

  $5,150,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,738 Sq Ft

  1302 Raintree Place, Winter Park, FL 32789

  An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired

  Rikhil Amin FANNIE HILLMAN & ASSOCIATES

  1302 Raintree Place, Winter Park, FL 32789
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  /12

  $7,000 per month

  • 4 Beds
  • 3 Baths
  • 2,310 Sq Ft
  • House for Rent

  1400 S Pennsylvania Ave, Winter Park, FL 32789

  A chic and trendy residence and winter park in an incredible location. A fully remodeled, one level four bedroom home with a fence corner lot. This home has an amazing curb appeal with its wide half circle, paved driveway, with plenty of parking flanked with lush mature landscaping. The open floor plan offers today's contemporary living and entertaining, with designer porcelain tile, trendy light

  Jack Keller JACK KELLER INC

  1400 S Pennsylvania Ave, Winter Park, FL 32789
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  $468,470 Sold Jun 20, 2025

  1026 Manchester Cir, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • Built 1977

  Last Sold Summary

  • 3% Below List Price
  • $272/SF
  • 25 Days On Market

  Current Estimated Value $485,328

  Last Listing Agent David Miller KELLER WILLIAMS HERITAGE REALTY

  1026 Manchester Cir, Winter Park, FL 32792
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  /2

  Est $428,880 Not Listed For Sale

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

  2838 Bright Bird Ln, Winter Park, FL 32792

  2838 Bright Bird Ln, Winter Park, FL 32792
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  /27

  $310,000

  • 3 Beds
  • 2 Baths
  • 1,178 Sq Ft

  5473 Bracken Ct, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Move-in ready 3-bedroom, 2-bath townhome in desirable Winter Park featuring recent exterior paint and a clean, modern presentation throughout. BRAND NEW water heater, A/C replaced in 2021, and NEW ROOF (2026). The spacious family room sits beneath dramatic two-story vaulted ceilings highlighted by tongue-and-groove ceiling planks, creating an open

  David Fraser KELLER WILLIAMS ADVANTAGE III

  5473 Bracken Ct, Winter Park, FL 32792
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  /19

  $1,000 per month

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

  5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792

  Attention Full Sail and UCF Students! This is the place for which you've been looking. This is a shared living space that is fully furnished with all utilities included. Each of the 4 rooms has its own electronic keypad lock for your privacy and security. The extra large common areas provide the perfect space for dining and living. Spacious laundry and kitchen provide you with plenty of space

  5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792
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  $430,000 Sold Aug 08, 2025

  1006 Bradford Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,130 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Above List Price
  • $202/SF
  • 7 Days On Market

  Current Estimated Value $437,769

  Last Listing Agent Paul Giannotti TERZA REAL ESTATE

  1006 Bradford Dr, Winter Park, FL 32792
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  /35

  Est $215,720 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft

  656 Saint Johns Ct Unit S, Winter Park, FL 32792

  656 Saint Johns Ct Unit S, Winter Park, FL 32792
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  /11

  $327,500

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  121 Stefanik Rd, Winter Park, FL 32792

  A MUST SEE! Beautifully remodeled 3 bedroom 2 bath home. This is a two bedroom and one bath in the front with a one bedroom one bath mother-in-law suite in the back, off of the laundry room with its own entrance as well. Main house has a large foyer and living room. Kitchen has beautiful cabinets and granite counter tops. Septic system was just replaced in September. Currently rented for $2,000

  Moe Mossa SAVVY AVENUE, LLC

  121 Stefanik Rd, Winter Park, FL 32792
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  /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
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  /2

  $1,595,000 Sold Sep 02, 2025

  1733 Harmon Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,267 Sq Ft
  • Built 2025

  Last Sold Summary

  • $488/SF
  • 27 Days On Market

  Current Estimated Value $1,572,177

  Last Listing Agent Jordan Freeland SOUTH REALTY, INC

  1733 Harmon Ave, Winter Park, FL 32789
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  /2

  Est $377,046 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  230 Killarney Bay Ct Unit 3, Winter Park, FL 32789

  230 Killarney Bay Ct Unit 3, Winter Park, FL 32789

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