Winter Park, FL Homes

• 

  

  

  /25

  $180,000

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 237, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. LOCATION, LOW HOA FEES AND NO ASSESSMENT FEES! excellently maintained turnkey 1 Bedroom/ 1 bathroom Condo at highly desired LAKESIDE MANOR community, with DOCK ACCESS to Lake KILLARNEY , true Florida living. This Low Maintenance Condo with LOW HOA FEES AND NO ASSESSMENT FEESi includes ground keeping and exterior / roof maintenance with an affordable

  Layla Zayed MARK SPAIN REAL ESTATE

  2500 Lee Rd Unit 237, Winter Park, FL 32789
• 

  

  

  /13

  $2,395 per month

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Townhouse for Rent

  3486 Bougainvillea Dr Unit A, Winter Park, FL 32792

  Nice house with 2 units in a great location and each unit is being rent separately. This property is located in the heart of Winter Park where everything is close by. This unit has great value and is near all of the main colleges. Come and enjoy this unit with your family and friends. Please schedule your showing today before it is gone.

  Smithj Salomon LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  3486 Bougainvillea Dr Unit A, Winter Park, FL 32792
• 

  

  /2

  $430,000 Sold Jul 25, 2025

  • 1,675 Sq Ft
  • $257/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  2003 Bentwood Dr, Winter Park, FL 32792

  Welcome to this well maintained three bedroom, two bathroom pool home, with a one year old roof in Winter Park! Perfectly designed for comfortable living, this home features a versatile office space, ideal for working from home.Inside, you’ll find an open floor plan with vaulted ceilings, spacious living areas with a cozy fireplace surrounded by built in shelves. This home features a

  Heather Kolin PALMANO GROUP RE BROKERAGE LLC

  2003 Bentwood Dr, Winter Park, FL 32792
• 

  

  

  /24

  Est $329,724 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft

  3173 Crown Jewel Ct, Winter Park, FL 32792

  3173 Crown Jewel Ct, Winter Park, FL 32792
• 

  

  

  /54

  $479,000

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

  130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789

  SUPERB LOCATION! Don’t miss out on this beautifully updated 2 bedroom 2.5 bath 2-story condo in Killarney Bay. Upon entering, you immediately notice the charm and character of this impeccably maintained condo. Recent updates include a fully renovated screened porch including floor, screen enclosure and roof, new sliding doors and windows, new refrigerator, new dishwasher, newly painted interior

  Lisa Gould KELLER WILLIAMS WINTER PARK

  130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789
• 

  

  /14

  $1,500 per month

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

  2929 Antique Oaks Cir Unit 53, Winter Park, FL 32792

  Welcome to this beautifully renovated 1-bedroom, 1-bathroom first-floor condo in the highly desirable Parkview Village community. This spacious and well-maintained unit features a modern, updated kitchen and bathroom, a large walk-in closet, and an in-unit washer and dryer for your convenience. The open-concept living and dining area creates a comfortable and functional layout, perfect for

  Julian Quezada INTERINVESTMENTS REALTY, INC.

  2929 Antique Oaks Cir Unit 53, Winter Park, FL 32792
• 

  /2

  $200,000 Sold Jul 25, 2025

  • 1,281 Sq Ft
  • $156/SF
  • 22 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  4952 Tangerine Ave, Winter Park, FL 32792

  Beautifully Updated 2BR/2BA Winter Park Townhome that is move-In Ready for a homeowners or investors. Rare opportunity to own a well-maintained 2-story townhome in a desirable Winter Park community. This spacious unit features 2 large bedrooms and 2 full bathrooms, an open floor plan, and numerous recent updates. Downstairs boasts ceramic tile and premium luxury vinyl flooring. The kitchen and

  Rick Brown KELLER WILLIAMS ADVANTAGE 2 REALTY

  4952 Tangerine Ave, Winter Park, FL 32792
• 

  /2

  Est $213,572 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 927 Sq Ft

  204 Lewfield Cir Unit 204, Winter Park, FL 32792

  204 Lewfield Cir Unit 204, Winter Park, FL 32792
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  /47

  $2,149,000

  • 5 Beds
  • 4.5 Baths
  • 3,174 Sq Ft

  1710 Oneco Ave, Winter Park, FL 32789

  Stunning 2020 Mediterranean Pool Home by M. Lahr Custom Homes in one of the sought-after neighborhoods of Winter Park. Experience unparalleled luxury in this breathtaking exquisite 5-bedroom, 4.5-bathroom home with bonus room that offers a perfect blend of comfort, and functionality. This exceptional residence features high-end designer finishes and exceptional craftsmanship throughout for modern

  Rhonda Chesmore KELLY PRICE & COMPANY LLC

  1710 Oneco Ave, Winter Park, FL 32789
• 

  

  /21

  $1,800 per month

  • 2 Beds
  • 2 Baths
  • 1,038 Sq Ft
  • Townhouse for Rent

  3019 Casselwood St, Winter Park, FL 32792

  ATTENTION GOOD RENTERS!! COME TO SHOW THIS WONDERFUL OPORTUNITY FOR RENT THIS WONDERFUL TOWNHOUSE IN A REALLY GOOD LOCATION IN WINTER PARK AREA NEAR TO SEMORAN. THIS TOWNHOUSE HAS 2 BED AND 2 BATH WITH A NICE DISTRIBUTION INSIDE. IT HAS AS WELL, A BACK YARD WHERE YOU CAN ENJOY WITH FAMILY AND FRIENDS. IT HAS AS WELL TWO PARKING CAR IN FRONT OF THE TOWNHOUSE. VERY CONVINIENT LOCATION!!! NEAR TO

  Maria G Camacho ORLANDO KEY REALTY LLC

  3019 Casselwood St, Winter Park, FL 32792
• 

  /2

  $599,000 Sold Jul 25, 2025

  • 2,266 Sq Ft
  • $264/SF
  • 20 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1935

  490 Shoreview Ave, Winter Park, FL 32789

  Step into timeless elegance with this beautiful 2-story, 3-bed, 2-bath historic home located in one of Winter Park’s most coveted neighborhoods. Built in 1935, this classic residence boasts stunning architectural details throughout—including solid wood floors, 10-inch baseboards, two cozy wood-burning fireplaces, and ornate trim surrounding the windows and doors. The generous living room opens

  Justin Harvey FLORIDA HOME TEAM REALTY LLC

  490 Shoreview Ave, Winter Park, FL 32789
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  /50

  Est $482,631 Not Listed For Sale

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

  1607 Little Wren Ln, Winter Park, FL 32792

  1607 Little Wren Ln, Winter Park, FL 32792
• 

  

  /34

  $610,000

  • 3 Beds
  • 3.5 Baths
  • 1,937 Sq Ft

  1250 Formosa Ave, Winter Park, FL 32789

  Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nestled in the highly sought-after Urban Green Community. Built in 2022, this move-in ready residence showcases sleek, contemporary finishes throughout all three levels. Step up to a welcoming covered and pavered front porch, fenced-in front yard, and into a thoughtfully designed layout. The first floor offers a

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  1250 Formosa Ave, Winter Park, FL 32789
• 

  

  /18

  $1,950 per month

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • House for Rent

  1902 Azalea Ave, Winter Park, FL 32792

  Welcome to 1902 Azalea Street, a beautifully maintained 3-bedroom, 2-bathroom home in the heart of Winter Park. This delightful property blends classic Florida charm with modern updates, offering a bright and inviting interior. Nestled on a quiet, tree-lined street, the home is perfect for relaxing or entertaining. Just minutes from Park Avenue, Rollins College, and top-rated schools, you’ll

  Alison Ashby CORCORAN PREMIER REALTY

  1902 Azalea Ave, Winter Park, FL 32792
• 

  /2

  $275,000 Sold Jul 25, 2025

  • 894 Sq Ft
  • $308/SF
  • 54 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1957

  849 Driver Ave, Winter Park, FL 32789

  Great Opportunity in Prime Location! Price adjustment below appraised value.Located just off the Fairbanks Avenue exit from I-4, this charming 2-bedroom, 1-bath fixer-upper sits on a generous 7,000 sq ft lot in a quiet, convenient neighborhood. With original hardwood floors in the living area and bedrooms, this home is full of character and ready for your personal touch. The

  Thor Falk CASTLE & COTTAGE REALTY LLC

  849 Driver Ave, Winter Park, FL 32789
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  /32

  Est $436,867 Not Listed For Sale

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

  1999 Canny Cove, Winter Park, FL 32792

  1999 Canny Cove, Winter Park, FL 32792
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  /36

  $720,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,256 Sq Ft

  2478 Whitehall Cir, Winter Park, FL 32792

  **Sellers will replace roof prior to closing** Expect to be impressed with this updated 3BR home in one of Winter Park’s well-established neighborhoods. It starts with great curb appeal – meticulously manicuredfront lawn, decorative paver stones surrounding the entryway and a 3-car garage! Stepinside to space originally designed as formal living and dining rooms – versatile

  Erica Magtira LPT REALTY, LLC

  2478 Whitehall Cir, Winter Park, FL 32792
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  /11

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • House for Rent

  460 Cambridge Blvd Unit A, Winter Park, FL 32789

  Fully renovated 3-bedroom, 2-bath home in the heart of Winter Park—available for immediate move-in! This charming unit features an updated kitchen with stainless steel appliances, durable vinyl plank flooring throughout, and a full-sized washer and dryer for added convenience. Enjoy private parking and an oversized fenced backyard, perfect for entertaining or relaxing outdoors. Located near

  Amy Fouraker 4 ACRE REALTY LLC

  460 Cambridge Blvd Unit A, Winter Park, FL 32789
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  /2

  $3,450,000 Sold Jul 25, 2025

  • 4,812 Sq Ft
  • $717/SF
  • 61 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 2025

  182 N Phelps Ave, Winter Park, FL 32789

  Welcome to a stunning new home positioned near Windsong and the AdventHealth Hospital. This extraordinary property boasts 4,812 square feet under AC. The stately manner is thoughtfully designed with four commodious bedrooms and five full-size bathrooms. Additionally, it features an expansive three-car garage complemented by an impressively constructed circular paver driveway. The first floor

  Marcio Tannus LA ROSA REALTY HORIZONS LLC

  182 N Phelps Ave, Winter Park, FL 32789
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  /9

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,027 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /26

  $362,500

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789

  Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfect blend of privacy, style, and unbeatable location. Just one block from Winter Park Village and only a mile from Park Avenue, you’ll enjoy walkable access to some of the area’s best dining, shopping, and entertainment.Located on the first floor, this beautifully renovated 2-bed, 2-bath home features

  Brandon Geers COMPASS FLORIDA LLC

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789
• 

  

  /79

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 2,102 Sq Ft
  • House for Rent

  1946 Strathaven Rd, Winter Park, FL 32792

  $100 OFF THE FIRST 6 MONTHSFor Rent – Spacious 3BR Home in Prime Winter Park Location!LOCATION, LOCATION, LOCATION! This spacious 3-bedroom, 2-bath home with a large den and cozy wood-burning fireplace sits on an oversized lot in Kenilworth Shores – Sec 7, with deeded access to Lake Berry.Zoned for Winter Park High, Glenridge Middle, and Brookshire Elementary, and just

  Youbel Montesino LPT REALTY, LLC

  1946 Strathaven Rd, Winter Park, FL 32792
• 

  /2

  $500,000 Sold Jul 25, 2025

  • 1,752 Sq Ft
  • $285/SF
  • 63 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1964

  2138 Whitehall Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to this well-maintained home in the desirable Kenilworth Shores Neighborhood of Winter Park. The three-bedroom, two-bath home has just over 1,750 square feet and has lots of extra storage. Wonderful floorplan with large living room, dining room, and separate family room with wood-burning fireplace. Updates include BRAND-NEW Roof (4/2025),

  Angela McCloskey KELLER WILLIAMS REALTY AT THE PARKS

  2138 Whitehall Dr, Winter Park, FL 32792
• 

  

  /11

  Est $436,274 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2877 Clever Ln, Winter Park, FL 32792

  2877 Clever Ln, Winter Park, FL 32792
• 

  

  /38

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,785 Sq Ft

  2708 Lion Heart Rd, Winter Park, FL 32792

  Here is a fantastic home in Winter Park Pines, a well established and sought after community and location in Winter Park! This property is located on a corner lot and has a private pool as well as a two-car garage. This a great way to obtain home ownership at an affordable price. The construction is a Block/Brick built home making it a solid home unlike one you could buy new today. The Roof and

  Corey Cannon BHHS FLORIDA REALTY

  2708 Lion Heart Rd, Winter Park, FL 32792
• 

  

  /18

  $4,900 per month

  • 4 Beds
  • 2.5 Baths
  • 1,856 Sq Ft
  • House for Rent

  2952 de Brocy Way, Winter Park, FL 32792

  Step inside and be amazed by this fully renovated Winter Park Pines home, where modern luxury, stylish finishes, and everyday comfort come together seamlessly. With spacious bedrooms, an open, airy layout, and designer touches throughout, this home is ideal for entertaining or simply enjoying peaceful living. Step out to a screened-in patio overlooking a sprawling backyard and private pool, your

  Summer Hornburg BELMONT REALTY

  2952 de Brocy Way, Winter Park, FL 32792
• 

  /2

  $425,000 Sold Jul 25, 2025

  • 1,947 Sq Ft
  • $218/SF
  • 83 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  1430 Hyde Park Dr, Winter Park, FL 32792

  Step inside and be ready to see an AMAZING LAKE VIEW from this SPLIT plan, 2 bedroom 2 bath BEAUTIFUL home. NEW LUXURY VINYL PLANK flooring throughout the entire home. NEW paint and NEW baseboards inside. The family room has a FIREPLACE, and a separate dining room adjacent to it. Kitchen features NEW STAINLESS STEEL APPLIANCES and beautiful lake views from the breakfast nook. The HUGE

  Heather Pryor KELLER WILLIAMS ADVANTAGE REALTY

  1430 Hyde Park Dr, Winter Park, FL 32792
• 

  

  /9

  Est $388,423 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  1768 Miller Ave, Winter Park, FL 32789

  1768 Miller Ave, Winter Park, FL 32789
• 

  

  /22

  $244,900

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  7744 Country Place Unit C4, Winter Park, FL 32792

  Location, Location, Location! This highly sought-after two-bedroom, two-bath condo in Winter Park won’t last long! Ideally situated close to the University of Central Florida, it's a perfect investment opportunity for parents offering lower monthly payments compared to the high costs of on-campus housing.Upgrades made in 2020 include a new roof, air conditioning system, and enhanced attic

  Travis Sorci DALTON WADE INC

  7744 Country Place Unit C4, Winter Park, FL 32792
• 

  

  /36

  $4,950 per month

  • 4 Beds
  • 2.5 Baths
  • 2,406 Sq Ft
  • House for Rent

  1580 Oakhurst Ave, Winter Park, FL 32789

  Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are

  Lisa Gould KELLER WILLIAMS WINTER PARK

  1580 Oakhurst Ave, Winter Park, FL 32789
• 

  /2

  $520,000 Sold Jul 25, 2025

  • 1,420 Sq Ft
  • $366/SF
  • 309 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  274 N Ranger Blvd, Winter Park, FL 32792

  Welcome to your fully renovated home located in the highly sought-after Winter Park Pines Golf Course Community. This beautiful open floor plan residence offers a fresh and modern living experience, perfect for both relaxation and entertaining. Inside you'll find brand-new flooring throughout, along with fully upgraded bathrooms that include stylish new vanities and custom tile work. The kitchen

  Wendy Aldana LLC NETWORTH REALTY OF ORLANDO, LLC

  274 N Ranger Blvd, Winter Park, FL 32792
• 

  

  /9

  Est $424,851 Not Listed For Sale

  • 2 Beds

  822 Symonds Ave, Winter Park, FL 32789

  822 Symonds Ave, Winter Park, FL 32789
• 

  

  /23

  $265,000

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  7707 Country Place Unit 4, Winter Park, FL 32792

  Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. Enjoy an insulated, screen-enclosed lanai with its own AC unit, plus a brand-new backyard deck and private patio. Both bedrooms offer ensuite baths with updated vanities and large walk-in closets. NEW luxury vinyl plank flooring throughout. Extended kitchen with added cabinets and bar seating. Laundry room

  Stephanie Sanchez WEICHERT REALTORS HALLMARK PRO

  7707 Country Place Unit 4, Winter Park, FL 32792
• 

  

  /22

  $1,399 per month

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

  3651 N Goldenrod Rd Unit B109, Winter Park, FL 32792

  Welcome home! This fantastic 2 bedroom, 2 bath Condo is available for move in on July 8th, 2025! You will love this fabulous condo in the charming and great central location of Winter Park /East Orlando. The 2 bedroom, 2 bath condo offers a spacious living and dining combo, with an open floor paln, large kitchen with lots of cabinet and storage space!! There are Sizable closet space in both

  Steve Simpson 407 PROPERTIES

  3651 N Goldenrod Rd Unit B109, Winter Park, FL 32792
• 

  /2

  $436,000 Sold Jul 24, 2025

  • 2,290 Sq Ft
  • $190/SF
  • 224 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1987

  5240 N Lake Burkett Ln, Winter Park, FL 32792

  Seller is offering up to $3,000 in concessions. Welcome to 5240 North Lake Burkett Lane, a classic 4 bedroom, 2.5 bathroom home, located in beautiful Winter Park! The open floor plan and high ceilings offer a bright, airy feel. At the center of the home is a large kitchen, connecting the dining, living, and family rooms. The primary suite is conveniently located on the first floor for

  Ashley Harper COLDWELL BANKER REALTY

  5240 N Lake Burkett Ln, Winter Park, FL 32792
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  /42

  Est $695,166 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,196 Sq Ft

  1252 Verdant Glade Place, Winter Park, FL 32792

  1252 Verdant Glade Place, Winter Park, FL 32792
• 

  

  /52

  $5,575,000

  • 5 Beds
  • 5.5 Baths
  • 5,164 Sq Ft

  1221 Richmond Rd, Winter Park, FL 32789

  An Award-Winning Architectural Masterpiece built by Chris Salhab of Valdara Custom Homes. 5,164 Sq Ft | 5 Bedrooms | 6 Bathrooms | Welcome to 1221 Richmond Rd, an extraordinary custom residence located in the coveted Virginia Heights neighborhood of Winter Park—offering deeded lake access to the Winter Park Chain of Lakes. This architectural showpiece was honored as the 2024 Parade of Homes

  Audra Wilks KELLER WILLIAMS WINTER PARK

  1221 Richmond Rd, Winter Park, FL 32789
• 

  

  /28

  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,375 Sq Ft
  • House for Rent

  1513 Harmon Ave, Winter Park, FL 32789

  This fantastic 2/2 plus office Orwin Manor home just completed new kitchen updates and features hardwood flooring throughout with tile in kitchen and Florida Room/Sunroom areas. Florida Room/sunroom is perfect light and bright area for home office/workspace/flex/fitness room. Great Room is a generous space for larger modular or L-couch layout. Newer interior paint throughout. Primary suite is

  Vincent Scarlatos CORCORAN PREMIER REALTY

  1513 Harmon Ave, Winter Park, FL 32789
• 

  /2

  $525,000 Sold Jul 23, 2025

  • 2,733 Sq Ft
  • $192/SF
  • 104 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1979

  4029 Cool Water Ct Unit 2, Winter Park, FL 32792

  Welcome Home! This spacious 5-bedroom, 3-bathroom home nestled in highly sought-after Winter Park. This home offers a versatile layout, oversized lot, and limitless potential to make it your own. Priced below market value based on square footage. Upgraded features include a NEW ROOF, flooring, updated plumbing, epoxy garage flooring, modern light fixtures, ceiling fans, freshly painted interior &

  Cedrick Williams MAGNUS REALTY GROUP LLC

  4029 Cool Water Ct Unit 2, Winter Park, FL 32792
• 

  

  /36

  Est $740,932 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,822 Sq Ft

  5263 Pine Lily Cir, Winter Park, FL 32792

  5263 Pine Lily Cir, Winter Park, FL 32792

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