Winter Park, FL Homes for Sale with Garage

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  $549,900

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft

  1261 Indiana Ave, Winter Park, FL 32789

  Welcome to The Townhomes at Harper Place, where elegance meets convenience in beautiful Winter Park. This spacious and impeccably maintained 3-bedroom, 2.5-bath townhome with a 2-car garage offers the perfect blend of style, comfort, and location.Step inside to discover an open and versatile floor plan, featuring a formal living and dining room combo, perfect for entertaining. The gourmet

  Barbara Remington PRESTIGE PROPERTY SHOP LLC

  1261 Indiana Ave, Winter Park, FL 32789
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  $695,000

  • 3 Beds
  • 2 Baths
  • 2,193 Sq Ft

  1427 Lake Florence Way, Winter Park, FL 32792

  Welcome to this beautifully maintained, Stunning Better-Than-New 6-Year-Old Custom Home in Gated Lake FlorencePreserve, one-owner custom home that truly has it all. From the moment you enter, you’ll appreciate the exceptional quality and craftsmanship, including upgraded 8' interior doors, 10-foot ceilings, crown molding, and elegant tray ceilings throughout—even in the primary suite. One of

  Doug Addeo COMMUNITY REALTY ASSOCIATES

  1427 Lake Florence Way, Winter Park, FL 32792
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  $398,000

  • 3 Beds
  • 2 Baths
  • 1,405 Sq Ft

  616 Ellendale Dr, Winter Park, FL 32792

  Desirable Winter Park Estates - close to everything! Beautifully updated 3 Bedroom 2 Bath POOL home which is located in a highly desirable school district! Updated Contemporary Kitchen has newer Cabinetry, newer Stainless-Steel appliances, and Granite countertops which connect with the open Living room. Dining area extends to the generous size Family room - Ideal for Entertaining. The home has a

  David Ruiz CENTRAL REALTY

  616 Ellendale Dr, Winter Park, FL 32792
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  $610,000

  • 4 Beds
  • 3 Baths
  • 2,846 Sq Ft

  3115 Heartleaf Place, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Back on the market as previous buyers financing fell through. This stunning 4-bedroom, 3-bathroom residence is situated on a desirable corner lot, offering ample space and privacy. This home was recently updated with a brand new HVAC system installed (May 2025), and a roof that’s only 4 years old (2021), complete plumbing repipe done in (2020). This

  Selby Turnbull EXP REALTY LLC

  3115 Heartleaf Place, Winter Park, FL 32792
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  $520,000

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  346 S Ranger Blvd, Winter Park, FL 32792

  PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone

  Tetyana Vyushkina IMPERIAL REALTY OF FLORIDA INC

  346 S Ranger Blvd, Winter Park, FL 32792
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  /20

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,146 Sq Ft

  1033 Hamlet Dr, Maitland, FL 32751

  This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's

  Bennie Olivo BOX REAL ESTATE LLC

  1033 Hamlet Dr, Maitland, FL 32751
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  $750,000

  • 3 Beds
  • 2 Baths
  • 2,296 Sq Ft

  805 Nottingham St, Orlando, FL 32803

  One or more photo(s) has been virtually staged. Charming, Fully Updated Home in Coveted Orwin Manor! Tucked perfectly between the charm of College Park and the luxury of Park Avenue, this beautifully renovated Orwin Manor home feels like something out of a storybook. Picture quiet, tree-lined streets, friendly neighbors who wave from their porches, and the perfect blend of old Orlando character

  Angela Worachek DALTON WADE INC

  805 Nottingham St, Orlando, FL 32803
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  $775,000

  • 3 Beds
  • 2.5 Baths
  • 1,838 Sq Ft

  5343 Brady Ln, Orlando, FL 32814

  Welcome to 5343 Brady Lane — a beautifully updated David Weekley home in the heart of Baldwin Park, offering charm, privacy, and a picture-perfect front porch overlooking a peaceful park with no homes directly in front. This 3-bedroom, 2.5-bath home spans 1,838 sq ft and features a spacious, light-filled layout with thoughtful upgrades throughout. The inviting front porch is ideal for rocking

  Cara Edwards ALL REAL ESTATE & INVESTMENTS

  5343 Brady Ln, Orlando, FL 32814
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  $1,300,000

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  1421 Sunnyside Dr, Maitland, FL 32751

  Welcome to 1421 Sunnyside Drive in Maitland, a beautifully maintained home where timeless design meets modern luxury. This 4-bedroom, 2.5-bath corner lot residence with a pool has a thoughtfully designed indoor and outdoor living space. Its location provides quick access to top-rated schools, boutique shopping, and local dining in one of the most desirable neighborhoods in the Maitland and Winter

  Amanda Binns STRICKLAND REALTY GROUP INC

  1421 Sunnyside Dr, Maitland, FL 32751
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  $2,885,000

  • 5 Beds
  • 5 Baths
  • 4,001 Sq Ft

  1411 Nottingham St, Orlando, FL 32803

  This one-of-a-kind, top-tier custom contemporary home in coveted Beverly Shores/Rose Isle delivers true turnkey luxury with exceptional finishes, premium cabinetry, high-end appliances, and fully integrated smart features throughout. The five-bedroom, three-and-a-half-bath main home plus a detached 384 SF casita (sixth bedroom) sits on a premium lot with unmatched access to scenic Mead

  Gwyn Clark FANNIE HILLMAN & ASSOCIATES

  1411 Nottingham St, Orlando, FL 32803
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  $1,097,000

  • 3 Beds
  • 3 Baths
  • 2,460 Sq Ft

  1901 Lake Sue Dr, Orlando, FL 32803

  One story, 3-bedroom, 3 bath, RENOVATED home with resort-style backyard and screened lap pool is ready to move in to. Lot Size: 14,331 Sq Ft / 1,331 SqM. This home features a modern kitchen with a marble Breakfast bar and marble countertops, an Open floor plan with lots of natural light. New White-Oak wood floors installed throughout in September 2025. The huge primary Bedroom suite with sitting

  Pamela Stewart REALCOM REAL ESTATE SERVICES INC

  1901 Lake Sue Dr, Orlando, FL 32803
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  /25

  $815,000

  • 3 Beds
  • 3.5 Baths
  • 2,407 Sq Ft

  1732 Ridgewood Ave Unit S, Maitland, FL 32751

  PRICE ADJUSTMENT/IMPROVEMENT! NOW IS YOUR OPPORTUNITY TO OWN THIS GORGEOUS 2 STORY TOWNHOME IN PRIME LOCATION! Discover a unique living experience in this Santa Barbara style townhome condo. Nestled in a sought after neighborhood on the border of Maitland/Winter Park. Inspired by the California architectural charm of Santa Barbara, this property offers a rare blend of style and convenience.

  Andrea Sider, PA KELLER WILLIAMS WINTER PARK

  1732 Ridgewood Ave Unit S, Maitland, FL 32751
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  /20

  $308,000

  • 3 Beds
  • 2 Baths
  • 1,076 Sq Ft

  1074 Hamlet Dr, Maitland, FL 32751

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, convenience, and an unbeatable location. From the moment you step inside, you’ll notice the inviting layout featuring a spacious living area filled with natural light and a functional kitchen equipped with newer stainless steel appliances—perfect for everyday living and entertaining alike. The home sits on a

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  1074 Hamlet Dr, Maitland, FL 32751
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  $285,000

  • 3 Beds
  • 3 Baths
  • 1,328 Sq Ft

  1618 Gulfview Dr Unit 417, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Welcome to this exquisitely renovated home offering the best value in the maintenance-free community of Park Lake Grove! This stunning 3-bedroom, 3-bathroom property features 1,328 square feet of beautifully updated living space and a rear-facing, fully enclosed one-car garage. Every inch of this home has been thoughtfully renovated with quality and

  Wendy Aldana LLC NETWORTH REALTY OF ORLANDO, LLC

  1618 Gulfview Dr Unit 417, Maitland, FL 32751

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