Winter Park, FL Homes

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  /34

  $119,000

  • 2 Beds
  • 2.5 Baths
  • 1,085 Sq Ft

  3002 George Mason Ave Unit 3, Winter Park, FL 32792

  Tucked away in Winter Park setting, this well-maintained 2-bedroom, 2.5-bathroom condo offers a blend of privacy and convenience. Enjoy quiet moments on the porch or the private balcony off the primary suite. The thoughtful layout features main living areas and a half bath on the first floor, with both bedrooms and two full baths upstairs for comfort and separation. Ideally located just minutes

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  (321) 399-7359

  3002 George Mason Ave Unit 3, Winter Park, FL 32792
• 

  Explore Winter Park

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  /26

  $2,998 per month

  • 3 Beds
  • 2.5 Baths
  • 1,852 Sq Ft
  • Townhouse for Rent

  1127 Minnesota Ave Unit 3, Winter Park, FL 32789

  Beautiful and very spacious 3BR/2.5BA with 2 car garage, large upstairs balcony, fenced patio, New wood flooring throughout the unit, All freshlypainted, all appliances including side by side refrigerator and full size washer and dryer. This property is centrally located in winter park FL,walking distance to shopping, restaurants, bars, coffee shops, Publix Supermarket, short driving distance to

  

  Moshe Sheffi

  HPL REALTY INVESTMENTS

  (321) 490-0678

  1127 Minnesota Ave Unit 3, Winter Park, FL 32789
• 

  

  /2

  $434,000 Sold Sep 12, 2025

  • 1,556 Sq Ft
  • $279/SF
  • 55 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1978

  1122 Washington Ave Unit 7, Winter Park, FL 32789

  Welcome to 1122 Washington Avenue – a delightful 2-bedroom, 2.5-bath townhome located in one of Winter Park’s most desirable neighborhoods. Just a short stroll to Park Avenue, Rollins College, the Winter Park Tennis Center, and the brand-new Seven Oaks Park, this home offers the perfect blend of lifestyle and location.This area is undergoing tremendous transformation, especially along the

  Raul Veitia BELMONT REALTY

  1122 Washington Ave Unit 7, Winter Park, FL 32789
• 

  

  /2

  Est $1,680,008 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,162 Sq Ft

  1130 Kenwood Ave, Winter Park, FL 32789

  1130 Kenwood Ave, Winter Park, FL 32789
• 

  

  

  /19

  $180,000

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792

  Well maintained 2 bedroom/2 bathroom condo located in Lancelot of Winter Park. This spacious second floor unit with large windows brings in plenty of natural light. The main living areas have wood laminate tile flooring and granite countertops in the kitchen. The bathrooms have been updated with sleek fixtures, modern design elements and newly painted. Nearby, you will find top rated schools and

  

  Monica Perlas

  COLDWELL BANKER REALTY

  (321) 449-2749

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792
• 

  

  /22

  $2,800 per month

  • 4 Beds
  • 2 Baths
  • 1,758 Sq Ft
  • House for Rent

  3326 Young St, Winter Park, FL 32792

  Available to view and rent Sept. 7th. Adorable, Newly Renovated 4 Bedroom, 2 Bathroom home with a large fenced yard. Fresh paint and brand-new vinyl flooring throughout. All new energy-efficient windows and doors. Lots of natural light with brand and new cabinets and quartz countertops in the kitchen along with Stainless Steel Appliances. Split bedroom floor plan. The primary bedroom features a

  

  Shelley Davis

  REMI EMERSON RESIDENTIAL

  (321) 250-5179

  3326 Young St, Winter Park, FL 32792
• 

  /2

  $1,555,000 Sold Sep 12, 2025

  • 3,971 Sq Ft
  • $392/SF
  • 146 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1990

  817 Antonette Ave, Winter Park, FL 32789

  Iconic Winter Park treasure! Welcome home to 817 Antonette, an architecturally inviting residence that exudes quality and charm. This thoughtfully designed home boasts detailed moldings and millwork, wood floors, high ceilings, and beautiful oversized windows throughout. A grand foyer leads to a central gallery with an atrium and a custom-designed bannister, while a unique glass ceiling allows

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  817 Antonette Ave, Winter Park, FL 32789
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  /2

  Est $507,875 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,631 Sq Ft

  1638 Berkshire Ave, Winter Park, FL 32789

  1638 Berkshire Ave, Winter Park, FL 32789
• 

  

  /50

  $469,900

  • 3 Beds
  • 3 Baths
  • 1,880 Sq Ft

  2835 Bongart Rd, Winter Park, FL 32792

  Seller is Motivated and open to incentives, must sell NOW! - Welcome to your spectacular pool home in Winter Park Estates. This beautifully renovated 3-bedroom, 3-bath residence features all the modern upgrades you've been searching for inside and out! Enjoy peace of mind with a new A/C unit (warranty included) and resurfaced pool complete with a new pump—perfect for Florida living. The backyard

  

  Claudia Jenkins

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 450-7314

  2835 Bongart Rd, Winter Park, FL 32792
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  /25

  $1,419 - $1,659 per month

  Indigo Winter Park

  1 Bed

  220 S Semoran Blvd, Winter Park, FL 32792

  Indigo Winter Park is a lavishly landscaped apartment home community. Each of our one bedroom, one bathroom apartments feature laminate flooring, carpeted bedrooms, washers & dryers, walk in closets, screened in patios, maple wood cabinetry, gas stoves and efficient appliances. Our pet-friendly apartment community includes three resort style pools, bbq grilling stations, two double tennis courts,

  220 S Semoran Blvd, Winter Park, FL 32792
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  /2

  $365,000 Sold Sep 11, 2025

  • 1,278 Sq Ft
  • $286/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  2008 Nottingdale Ln, Winter Park, FL 32792

  Nestled in the highly desirable Winter Park, Florida, 2008 Nottingdale Lane presents a meticulously updated and move-in-ready single-family home. This delightful residence offers 3 bedrooms and 2 bathrooms within a comfortable 1,278 square feet of living space, all without the encumbrance of a Homeowners Association (HOA). Situated on a generous 0.24-acre lot, the property boasts a fully fenced

  Robert Bretz, PA EXP REALTY LLC

  2008 Nottingdale Ln, Winter Park, FL 32792
• 

  /2

  Est $680,318 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  355 Cambridge Blvd, Winter Park, FL 32789

  355 Cambridge Blvd, Winter Park, FL 32789
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  /43

  $864,900

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft

  1090 Wildmeadow Run, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. This luxurious Modern Style home delivers the pinnacle lifestyle, in every aspect of MAINTENANCE FREE LIVING. You will enjoy premium views of nature with a RESORT CLUBHOUSE featuring an abundance of amenities including a resort pool, fitness center & playground, all JUST 250 FEET AWAY....This home has been IMPECCABLY MAINTAINED, and includes the

  

  Rod Chevalier

  BHHS FLORIDA REALTY

  (321) 339-2639

  1090 Wildmeadow Run, Winter Park, FL 32792
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  /30

  $2,995 per month

  • 3 Beds
  • 2 Baths
  • 1,678 Sq Ft
  • House for Rent

  502 Dunraven Dr, Winter Park, FL 32792

  Discover the perfect blend of comfort and convenience in this delightful 3-bedroom, 2-bathroom home nestled in the sought-after Kenilworth Shores neighborhood of Winter Park. With over 1,600 square feet of thoughtfully designed living space, this property offers everything you need for comfortable Florida living. The home features two separate living spaces that are perfect for entertaining or

  Kelly Price KELLY PRICE & COMPANY LLC

  502 Dunraven Dr, Winter Park, FL 32792
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  /2

  $1,785,000 Sold Sep 11, 2025

  • 2,907 Sq Ft
  • $614/SF
  • 29 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1953

  1640 Mayfield Ave, Winter Park, FL 32789

  This elegant one story home is located in highly desirable Winter Park on an oversized .28 acre lot with mature and lush landscaping and NO HOA. It has 10' ceilings and an open floor plan combining kitchen, dining, and living rooms with gorgeous wood floors and plenty of natural light overlooking the secluded & screened salt water pool with cascading water features, gas heated spa, and covered

  Beverly Brown RE/MAX PRIME PROPERTIES

  1640 Mayfield Ave, Winter Park, FL 32789
• 

  /2

  Est $1,796,803 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,590 Sq Ft

  2125 Sycamore Dr, Winter Park, FL 32789

  2125 Sycamore Dr, Winter Park, FL 32789
• 

  

  /89

  $950,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,074 Sq Ft

  4107 Gabriella Ln, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Do you have a vision? Do you love Nature? Welcome to this Exceptional Bear Gully Lakefront Retreat – A Rare Blend of Privacy and Natural Beauty! Refurbish the house as it is, or start new on this amazing rare natural Florida lakefront ground. Tucked away on the serene shores of Bear Gully Lake, this one-of-a-kind property presents a rare

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  (321) 382-1061

  4107 Gabriella Ln, Winter Park, FL 32792
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  /40

  $1,293 - $1,830 per month

  Seabrook

  1 - 2 Beds

  3114 Terry Brook Dr, Winter Park, FL 32792

  The Seabrook Apartment community is located near the 408 Expressway, close to shopping and dining areas 1/4 mile away, just minutes away from the downtown areas of Orlando and Winter Park. Several renowned schools such as Brookshire Elementary, Glenridge Middle School and Winter Park High School are nearby as well. We offer spacious one and two-bedroom apartments. All of our homes have been

  3114 Terry Brook Dr, Winter Park, FL 32792
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  /2

  $410,000 Sold Sep 11, 2025

  • 1,907 Sq Ft
  • $215/SF
  • 109 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2023

  2949 Clever Ln, Winter Park, FL 32792

  Welcome to this stunning former model townhome built in 2023, ideally located in the highly sought-after gated community of Grayson Square in Winter Park, Florida. This beautifully designed residence offers a blend of modern finishes and functional layout, with the first floor featuring a completely open floor plan bathed in natural light. The spacious kitchen boasts quartz countertops, upgraded

  Joseph Sipp KELLER WILLIAMS WINTER PARK

  2949 Clever Ln, Winter Park, FL 32792
• 

  /2

  Est $1,005,084 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,387 Sq Ft

  2217 Howard Dr, Winter Park, FL 32789

  2217 Howard Dr, Winter Park, FL 32789
• 

  

  /46

  $1,100,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,839 Sq Ft

  2880 Old Castle Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. Welcome to this beautifully designed executive pool home with private in-law quarters, nestled on an oversized corner lot in the gated community of Bear Gully Pointe in Winter Park. Thoughtfully crafted with architectural elegance, this residence features timeless details including plantation shutters, crown molding, and hardwood flooring throughout the

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 517-2794

  2880 Old Castle Dr, Winter Park, FL 32792
• 

  

  /20

  $2,195 per month

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft
  • House for Rent

  438 Garfield Ave, Winter Park, FL 32789

  Updated 3-bedroom, 2-bath single family home in downtown Winter Park. Separate living, dining, and family rooms with laminate flooring throughout. Fresh paint throughout and new carpet in the bedrooms. Kitchen has updated cabinetry and granite countertops. Single car garage with laundry area and washer/dryer included. Front and side screened porches with fully fenced backyard, total sq footage

  Christopher Gold WMGI

  438 Garfield Ave, Winter Park, FL 32789
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  /2

  $265,000 Sold Sep 11, 2025

  • 1,036 Sq Ft
  • $256/SF
  • 116 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1982

  3310 Royal St, Winter Park, FL 32792

  Welcome to 3310 Royal Street – a beautifully maintained mid-century gem nestled in one of Winter Park’s most desirable neighborhoods. This 2-bedroom, 1 and a half bath home offers the perfect blend of timeless charm and modern updates, ideal for families, professionals, or anyone looking to enjoy the Winter Park lifestyle.Step inside to discover an open-concept layout filled with natural

  Kevin Schudel BUY IT INC

  3310 Royal St, Winter Park, FL 32792
• 

  /2

  Est $266,268 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,227 Sq Ft

  7796 Country Place Unit E1, Winter Park, FL 32792

  7796 Country Place Unit E1, Winter Park, FL 32792
• 

  

  /35

  $450,000

  • 4 Beds
  • 2.5 Baths
  • 1,980 Sq Ft

  1660 Tremont Ln, Winter Park, FL 32792

  4 Bedrooms | 2.5 Baths | New Roof | Winter Park’s Country LaneWelcome to this well-cared-for 4-bedroom, 2.5-bath home in the highly desirable Country Lane neighborhood of Winter Park!On the first floor, you’ll find a bright and inviting layout with a kitchen featuring stainless steel appliances, along with ample cabinet and counter space. There’s plenty of room to entertain, with

  

  Jason Howell

  REAL BROKER, LLC

  (321) 325-3575

  1660 Tremont Ln, Winter Park, FL 32792
• 

  

  /37

  $1,318 - $3,121 per month

  Cranes Landing Apartments

  1 - 3 Beds

  3440 N Goldenrod Rd, Winter Park, FL 32792

  Incredible Move In Specials!Up to 6 Weeks Free!Receive a small kitchen appliance if you Look & Lease the same day!!!LIMITED TIME ONLY!!!Open House Saturday 10am - 4pm

  3440 N Goldenrod Rd, Winter Park, FL 32792
• 

  /2

  $240,000 Sold Sep 10, 2025

  • 1,173 Sq Ft
  • $205/SF
  • 41 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  2480 Tahoe Cir, Winter Park, FL 32792

  Seminole County and Winter Park! Centrally located on the border of Orange County, this well-established community of Cedarwood Village is conveniently located to beautiful Park Ave and all of the greater Orlando suburbs, locations and attractions. This well maintained single story cinderblock stucco has amble skylight natural light, open kitchen to family room, soaring vaulted ceilings and

  Michael Wood UNITED REAL ESTATE PREFERRED

  2480 Tahoe Cir, Winter Park, FL 32792
• 

  /2

  Est $333,386 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,550 Sq Ft

  2688 Galliano Cir, Winter Park, FL 32792

  2688 Galliano Cir, Winter Park, FL 32792
• 

  

  /8

  $260,000

  • Land
  • 0.81 Acre
  • $320,988 per Acre

  3580 Wilde Ave, Winter Park, FL 32792

  Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just shy of an acre, lot in coveted Winter Park. Nestled on a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level lot on a

  

  Gwendolen Flynn

  COLDWELL BANKER RESIDENTIAL RE

  (321) 334-2867

  3580 Wilde Ave, Winter Park, FL 32792
• 

  

  /13

  $1,200 per month

  • 1 Bath
  • 546 Sq Ft
  • Condo for Rent

  7417 Daniel Webster Dr Unit 3, Winter Park, FL 32792

  Cozy condo in The Colonies Community. This unit is Ground floor 1 bed 1bath with a community Pool. Ceramic Tile throughout the unit, stainless steal appliances, washer and dryer hookup with a porch area. Conveniently located close to supermarkets, shopping, Orlando airport and much more. You don't want to miss this opportunity. Contact us now!

  Georgina Pinango ROMAN'S PRO REALTY LLC

  7417 Daniel Webster Dr Unit 3, Winter Park, FL 32792
• 

  /2

  $25,000 Sold Sep 09, 2025

  • Land
  • 0.2 Acre
  • $125,000 per Acre

  • 10 Days On Market

  1964 Bering Ave, Winter Park, FL 32789

  There is a light pole easement. This lot is not buildable and is only good for non structural uses that are comparable with duke energy requirements. Please conduct your own due diligence before making an offer.

  Clarence Fields LUXURY & BEACH REALTY INC

  1964 Bering Ave, Winter Park, FL 32789
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  /42

  Est $1,591,553 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,052 Sq Ft

  1805 Harland Park Dr, Winter Park, FL 32789

  1805 Harland Park Dr, Winter Park, FL 32789
• 

  

  /42

  $765,000

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft

  2418 Whitehall Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. MAJOR PRICE REDUCTION! MOTIVATED SELLER! Don't miss out!!! A true GEM located in the highly desirable Brookshire Heights, presenting this FULLY REMODELED spacious single-story property in the heart of WINTER PARK. Showcasing a new meticulously designed floorplan, this property has also recently been EXTENDED by a total approx. 1,040 sqft. Exuding

  

  Alice Anne Jackson

  CORCORAN PREMIER REALTY

  (321) 599-7240

  2418 Whitehall Cir, Winter Park, FL 32792
• 

  

  /23

  $1,881 - $6,506 per month

  Juno Winter Park

  Studio - 3 Beds

  1305 Morgan Stanley Ave, Winter Park, FL 32789

  Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,

  1305 Morgan Stanley Ave, Winter Park, FL 32789
• 

  /2

  $2,200,000 Sold Sep 09, 2025

  • 3,155 Sq Ft
  • $697/SF
  • 2 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1954

  1554 Lake Knowles Cir, Winter Park, FL 32789

  Exuding timeless charm and Southern elegance, this gorgeous Charleston-style residence sits on a large lot overlooking the tranquil waters of Lake Knowles. Framed by a picturesque brick street lined with beautiful homes, the property boasts striking curb appeal, a 32-foot second-story porch with breathtaking sunset views, and classic architectural details that invite you in at every turn. A

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1554 Lake Knowles Cir, Winter Park, FL 32789
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  /26

  Est $478,984 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft

  2469 Firstlight Way, Winter Park, FL 32792

  2469 Firstlight Way, Winter Park, FL 32792
• 

  

  /19

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7706 Country Place Unit A8, Winter Park, FL 32792

  Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining

  

  Carmen Vazquez

  REALTY TECH INC

  (321) 339-0107

  7706 Country Place Unit A8, Winter Park, FL 32792
• 

  

  /17

  $1,695 per month

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft
  • House for Rent

  2328 Inagua Way, Winter Park, FL 32792

  This 2 bedroom, 2 bathroom home is located in the Windward Square community near local Winter Park shops, restaurants, and schools. Features include a spacious floor plan with a large main living area, a lovely kitchen, dining room, a wonderful primary suite with walk-in closet, a laundry closet, a screened patio, a beautiful fenced backyard, and carport. Community amenities include 2 swimming

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  2328 Inagua Way, Winter Park, FL 32792
• 

  /2

  $100,000 Sold Sep 09, 2025

  • 1,036 Sq Ft
  • $97/SF
  • 38 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792

  What an opportunity !! A 2 bedroom 2 bath Condo located in Winter Park. Fantastic opportunity-priced to sell! 2 bedroom, 2 bath condo in The Colonies ready for new owner. Light and bright First floor unit features Eat-kitchen, tile floors throughout - no carpet! French doors with built-in blinds lead to spacious balcony. Both bedrooms have large Walk-In closets! *Inside laundry *A/C 2017 -

  Pedro Ramos ROCKER'S REAL ESTATE, LLC

  7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792
• 

  

  /47

  Est $1,192,567 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,575 Sq Ft

  1939 Woodcrest Dr, Winter Park, FL 32792

  1939 Woodcrest Dr, Winter Park, FL 32792

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