Winter Park, FL Homes

• 

  

  

  /29

  $375,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  2827 Euston Rd, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to 2827 Euston Rd, a beautifully updated home in the highly desirable Winter Park area with the added bonus of no HOA! This charming residence offers 3 beds, 2baths, and a versatile bonus room that can be used as an office, playroom, or additional living space.The master suite is thoughtfully separated from the other two bedrooms, providing

  

  Evelyn Tejada

  REGENCY REAL ESTATE LLC

  (321) 461-5735

  2827 Euston Rd, Winter Park, FL 32789
• 

  

  

  /24

  $1,349 - $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
• 

  

  /2

  $480,000 Sold Jul 28, 2025

  • 1,598 Sq Ft
  • $300/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  1545 Indiana Ave Unit B, Winter Park, FL 32789

  Tucked away on a quiet street blocks from the cultural heartbeat of Winter Park is this 3-bedroom, 2.5-bath townhouse-style condo that offers a balance of comfort, convenience, and charm. With nearly 1,600 square feet of thoughtful space, the two-story home lives large, featuring an open-concept main floor with high ceilings, ceramic tile throughout, a spacious kitchen with granite counters and

  Ron Murray MAGIC REALTY LLC

  1545 Indiana Ave Unit B, Winter Park, FL 32789
• 

  

  /2

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 687 Sq Ft

  700 Melrose Ave Unit G, Winter Park, FL 32789

  700 Melrose Ave Unit G, Winter Park, FL 32789
• 

  

  

  /18

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,637 Sq Ft

  1050 Reading Ct, Winter Park, FL 32792

  Great investment opportunity in the prime location of Winter Park, Florida. Ideal for a growing family or investor. Well established neighborhood of Howell Estates, 3 bedroom, 2 full bathrooms, 1,637 square feet of living area with just over a quarter of an acre. Split plan bedrooms for added privacy. Exterior of the home is concrete block and stucco. The eat-in-kitchen and large family room

  

  Carmen Vazquez

  REALTY TECH INC

  (321) 850-2823

  1050 Reading Ct, Winter Park, FL 32792
• 

  

  /27

  $7,495 per month

  • 4 Beds
  • 3.5 Baths
  • 3,470 Sq Ft
  • House for Rent

  1841 Harland Park Dr, Winter Park, FL 32789

  Welcome home to the prestigious community of Windsong in Winter Park. Upon entering this Toll Brothers-built home, you will notice no detail has been spared. Soaring ceilings greet you as you enter the foyer. This 4-bedroom 3.5-bathroom home is loaded with upgrades. The office includes beautiful wood and detailed custom bookshelves with a double door for privacy. The formal dining room features a

  Craig Luiz SELECTIVE REALTY GROUP LLC

  1841 Harland Park Dr, Winter Park, FL 32789
• 

  /2

  $389,000 Sold Jul 25, 2025

  • 1,581 Sq Ft
  • $246/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  7331 Blue Jacket Place W, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Incredible Value! Priced to sell below market value—this is your chance to secure a fully upgraded home at a price that won’t last long. Act fast before it's gone!Welcome to this beautifully updated 3-bedroom, 2-bathroom home located in the highly desirable Winter Park community with no HOA! This luxury home sits on a large, fully fenced lot and

  Wendy Aldana LLC NETWORTH REALTY OF ORLANDO, LLC

  7331 Blue Jacket Place W, Winter Park, FL 32792
• 

  /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
• 

  

  /89

  $1,000,000

  • 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
• 

  

  /53

  $1,329 - $2,029 per month

  Serena Winter Park

  1-2 Beds

  2890 Red Lion Square, Winter Park, FL 32792

  Serena Winter Park is a newly remodeled apartment community. Our one and two bedroom apartment floor plans feature contemporary upgrades, large windows, spacious walk in closets, open kitchen styles and fantastic storage spaces. Our bungalow flats also offer private entry and patio. Our pet-friendly apartment community includes an all new impeccable 24-hour fitness center and billiards lounge! A

  2890 Red Lion Square, 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
• 

  /2

  Est $328,023 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
• 

  

  /42

  $875,000

  • 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
• 

  

  /16

  $2,480 per month

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • House for Rent

  1729 Puritan Ave, Winter Park, FL 32792

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

  Hunter Fendley MAIN STREET RENEWAL LLC

  1729 Puritan Ave, 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 $2,278,427 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,640 Sq Ft

  1770 Oakhurst Ave, Winter Park, FL 32789

  1770 Oakhurst Ave, Winter Park, FL 32789
• 

  

  /44

  $729,000

  • 4 Beds
  • 2.5 Baths
  • 2,046 Sq Ft

  607 Dunblane Dr, Winter Park, FL 32792

  Welcome to this beautifully renovated 4-bedroom, 2.5-bath home in the heart of Winter Park, just minutes from Park Avenue’s top dining and shopping. Thoughtfully updated from top to bottom, this move-in-ready home features a brand-new AC system, luxury vinyl plank flooring throughout, and a stunning chef’s kitchen with quartz waterfall countertops, custom cabinetry, and all-new stainless steel

  

  Khozaif Merali

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 490-4706

  607 Dunblane Dr, Winter Park, FL 32792
• 

  

  /28

  $1,589 - $1,629 per month

  Elon Winter Park

  1 Bed

  712 Nicolet Ave, Winter Park, FL 32789

  Welcome to Elon Winter Park Apartments in Winter Park, Florida, where chic meets serenity in the heart of Winter Park's vibrant tapestry. Nestled within this charming community, our boutique one-bedroom apartments redefine urban living with spacious interiors, a contemporary aesthetic, and designer accents that elevate every moment. Immerse yourself in the allure of Winter Park's entertainment

  712 Nicolet Ave, Winter Park, FL 32789
• 

  /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
• 

  /2

  Est $308,109 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,233 Sq Ft

  603 Warrenton Rd, Winter Park, FL 32792

  603 Warrenton Rd, Winter Park, FL 32792
• 

  

  /35

  $149,900

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit E103, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Price Reduced!! Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with all the perks of modern living. Located in the heart of Orlando, this condo is perfect for those looking for a blend of city life and natural beauty. As you step into the condo, you're greeted by a

  

  Jason Price

  ROBERT SLACK LLC

  (321) 490-1756

  1695 Lee Rd Unit E103, Winter Park, FL 32789
• 

  

  /23

  $1,600 per month

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

  1695 Lee Rd Unit D212, Winter Park, FL 32789

  This great second floor two-bedrooms 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 D212, Winter Park, FL 32789
• 

  /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
• 

  /2

  Est $393,127 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,262 Sq Ft

  5421 Albert Dr, Winter Park, FL 32792

  5421 Albert Dr, Winter Park, FL 32792
• 

  

  /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
• 

  

  /74

  $1,841 - $5,181 per month

  Vintage Winter Park Apartments

  1-3 Beds

  7490 Dwell Well Way, Winter Park, FL 32792

  Dwell well with us. Welcome to quintessential Vintage Winter Park, a residential community featuring One, Two & Three bedroom apartments in Winter Park, FL. Spacious layouts and amenities welcome you home, along with exceptional service and an ideal location within walking distance to shopping, dining and entertainment options.

  7490 Dwell Well Way, Winter Park, FL 32792
• 

  /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
• 

  /2

  Est $2,442,308 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 4,002 Sq Ft

  1620 Palm Ave, Winter Park, FL 32789

  1620 Palm Ave, Winter Park, FL 32789
• 

  

  /45

  $1,300,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,303 Sq Ft

  1500 Mizell Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. An extraordinary opportunity to own a beautifully renovated home on a prestigious tree-lined street in Winter Park’s 32789. Set on a desirable 13,500 square foot (90 × 150) lot with no HOA and bordering the prestigious Windsong community, this prime property offers the freedom to live comfortably now, expand

  

  Lisa Ratanasirintrawoot

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 485-6636

  1500 Mizell Ave, Winter Park, FL 32789
• 

  

  /21

  $1,375 per month

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

  200 Saint Andrews Blvd Unit 3412, Winter Park, FL 32792

  BEST UNIT LOCATION IN THE FOUR SEASON COMPLEX! This large one bedroom condo is available for lease immediately. The freshly-painted second floor home features a huge bedroom and a spacious walk-in closet. Since it's an end-unit, there are no neighbors on one side. It's located above the laundry room so you're close by and don't have to deal with neighbors below you. You're also right next to the

  Kaveh Albekord ALBEKORD, INC.

  200 Saint Andrews Blvd Unit 3412, 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
• 

  /2

  Est $228,148 Not Listed For Sale

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

  632 Montego Bay Ct, Winter Park, FL 32792

  632 Montego Bay Ct, Winter Park, FL 32792
• 

  

  /26

  $699,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,622 Sq Ft

  1891 Bryan Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Rare find in Winter Park! This charming one-story pool home offers three bedrooms, two full baths, high ceilings, and an open floor plan—all at an incredible price point. The updated kitchen features gas appliances, a center island, breakfast bar, and a separate beverage fridge. Wood-look tile flooring runs throughout the home for a cohesive, modern

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 336-5610

  1891 Bryan Ave, Winter Park, FL 32789
• 

  

  /39

  $1,192 - $1,727 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
• 

  /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
• 

  /2

  Est $498,125 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,874 Sq Ft

  2657 Tierra Cir, Winter Park, FL 32792

  2657 Tierra 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
• 

  

  /34

  $2,950 per month

  • 4 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • House for Rent

  5037 Lake Howell Rd, Winter Park, FL 32792

  Single family home for rent in the desirable city of Winter Park! This beautiful home features a main house with 3 bedrooms and 1 bathroom, with an in-law suite of 1 bedroom and 1 bathroom, located in the back of the oversized backyard where you can park all your vehicles including your boat or RV as there is no HOA! Enjoy the 0.27 acre lot completely fenced backyard for yourself, friends and

  Rafael Casallas, Pa EMPIRE NETWORK REALTY

  5037 Lake Howell Rd, Winter Park, FL 32792
• 

  /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
• 

  /2

  Est $679,653 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,946 Sq Ft

  2308 Summerfield Rd, Winter Park, FL 32792

  2308 Summerfield Rd, Winter Park, FL 32792

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