Winter Park, FL Homes for Sale with Garage

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  $1,595,000

  • 3 Beds
  • 2 Baths
  • 2,012 Sq Ft

  1113 Via Del Mar, Winter Park, FL 32789

  Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceablehomesite offering rare scale, privacy, and extraordinary future build potential. The primaryvalue is in the land, presenting an unparalleled canvas for a custom luxury residence, withvirtually no comparable vacant land available in the immediate vicinity. Set on a tranquil smalllake that

  David Barany BAY HILL REALTY LLC

  1113 Via Del Mar, Winter Park, FL 32789
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  $500,000

  • 3 Beds
  • 2 Baths
  • 1,413 Sq Ft

  512 N Lakemont Ave, Winter Park, FL 32792

  Set on an oversized corner lot in one of the most desirable pockets of Winter Park, this 3-bedroom, 2-bath pool home blends character, location, and opportunity.The backyard is a standout feature, with a resurfaced pool finished in Tahoe Blue PebbleTec and positioned for open sky views, a rare find in a neighborhood known for its mature tree canopy. It creates a bright, inviting outdoor space

  David Plasencia COLDWELL BANKER REALTY

  512 N Lakemont Ave, Winter Park, FL 32792
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  $695,000

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft

  715 S Ranger Blvd, Winter Park, FL 32792

  Welcome to your dream home in the highly sought-after community of Winter Park Pines! This beautifully maintained 4-bedroom, 3-bathroom residence offers 2,312 square feet of comfortable and stylish living space ideally designed for modern and multigenerational lifestyles.The recently remodeled primary suite is a true retreat, featuring new carpeting and tile flooring, dual granite vanities,

  Chuck Tolfa DAHLIA REALTY GROUP

  715 S Ranger Blvd, Winter Park, FL 32792
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  /22

  $235,000

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  2712 Tortoise Cove, Winter Park, FL 32792

  Why Rent WHEN you can own this 2 bedroom 1 bath single car garage on this 1/2 duplex with NO HOA. Located conveniently to all major roads, shopping, schools and restaurants. New roof installed 2025. Don't hesitate to come view!

  Lisa Wright CHARLES RUTENBERG REALTY ORLANDO

  2712 Tortoise Cove, Winter Park, FL 32792
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  $6,888,888

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,636 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  Set in the perfect Winter Park location, within exclusive Via Tuscany, this unique, RESILIENT CONSTRUCTION residence built by Developer & Builder Group, offers a rare blend of enduring quality, refined privacy, and effortless sophistication. Showcasing the finest European finishes, premium appliances, and exquisite light fixtures; this home is filled with clear, natural light and fresh air,

  Belinda Moreno The Keyes Company

  2661 Vía Tuscany, Winter Park, FL 32789
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  $1,500,000

  • 5 Beds
  • 4.5 Baths
  • 3,109 Sq Ft

  777 Halifax Ave, Winter Park, FL 32792

  Virtually Staged. Built in 2021 by David Weekley Homes, this thoughtfully designed 5-bedroom, 4.5-bath residence delivers 3,109 square feet of refined, light-filled living in one of Central Florida's most desirable locations. The sought-after Easterley floorplan opens into a bright, open-concept layout where soaring ceilings and abundant natural light set an effortlessly elegant tone, with

  Jared Smith SAFFORD REAL ESTATE LLC

  777 Halifax Ave, Winter Park, FL 32792
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  $625,000

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,978 Sq Ft

  2251 Nairn Dr, Winter Park, FL 32792

  Virtually Staged. Virtually Staged. Welcome to this exceptional SINGLE FAMILY-TOWNHOME with NO HOA offering the perfect blend of comfort, style, and location! Beautiful modern 4-bedroom, 2.5-bath, located in one of Winter Park's most established and sought-after neighborhoods. This spacious home features wood and laminate flooring throughout, a downstairs bonus room, a separate utility room, a

  Alfredo Karam COLDWELL BANKER REALTY

  2251 Nairn Dr, Winter Park, FL 32792
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  $1,895,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,617 Sq Ft

  914 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. 914 Enclave Place is a beautiful Alys Beach inspired design. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with

  Matthew Burks CORCORAN PREMIER REALTY

  914 Enclave Place, Winter Park, FL 32792
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  $710,000

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  300 Carolina Ave Unit 402C, Winter Park, FL 32789

  Virtually Staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from the boutiques, dining, and charm of Park Avenue. This unique 4th floor residence offers an exceptional combination of space, privacy, and potential. Featuring 3 bedrooms and 2 bathrooms, the expansive floor plan has been enlarged

  Erin Baker FANNIE HILLMAN & ASSOCIATES

  300 Carolina Ave Unit 402C, Winter Park, FL 32789
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  $415,000

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft

  1533 Springtime Loop, Winter Park, FL 32792

  Welcome to this inviting 3-bedroom, 2-bathroom pool home in the Autumn Glen neighborhood of Winter Park, offering over 1,100 square feet of comfortable living space. As you step through the front door, you are immediately greeted by the bright, open-concept design, with natural light flowing throughout the home and creating a warm and welcoming atmosphere. To your left, the kitchen takes center

  Daniel Lennon LPT REALTY LLC

  1533 Springtime Loop, Winter Park, FL 32792
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  $765,000

  • 4 Beds
  • 3 Baths
  • 2,673 Sq Ft

  110 Longhorn Rd, Winter Park, FL 32792

  Virtually Staged. Nestled on an OVERSIZED HOMESITE of well over half an acre in the sought-after Lake Ann Estates of Winter Park, this BEAUTIFULLY UPDATED 4-bedroom, 3-bath pool home offers the perfect combination of space, style, and freedom with NO HOA. Surrounded by MATURE LANDSCAPING and offering more than 2,600 SQUARE FEET of thoughtfully designed living space, this single-story residence is

  Jennifer Wemert WEMERT GROUP REALTY LLC

  110 Longhorn Rd, Winter Park, FL 32792
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  $1,262,500

  Open Sun 12AM - 3PM $13K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,024 Sq Ft

  2015 Summerfield Rd, Winter Park, FL 32792

  Welcome to one of Winter Park's most impressive move-in-ready homes, where luxury, comfort, and location come together seamlessly.Completely reimagined and renovated, this stunning 4-bedroom, 4-bath residence offers the rare combination of modern construction quality and an established Winter Park location just minutes from Baldwin Park, Park Avenue, Rollins College, and top-rated

  Courtney Lindsay UNITED REAL ESTATE PREFERRED

  2015 Summerfield Rd, Winter Park, FL 32792
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  /2

  $1,495,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,738 Sq Ft

  901 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, blending timeless character with modern luxury. 901 Enclave Place (Lot1) is a thoughtfully designed courtyard home offering an elegant yet functional layout centered around private outdoor living. A charming covered front porch

  Laura Earl CORCORAN PREMIER REALTY

  901 Enclave Place, Winter Park, FL 32792
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  $625,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  1871 Bryan Ave, Winter Park, FL 32789

  Opportunity meets location at 1871 Bryan Avenue, a well-positioned Winter Park property offering an approachable entry point into the highly sought-after 32789 area. Set on a 50-by-127-foot lot, the home features 1,210 square feet of living space with a practical layout that can suit a variety of needs, whether you’re purchasing your first home, looking to downsize, or adding a property to your

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1871 Bryan Ave, Winter Park, FL 32789
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  $350,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft

  2521 Galliano Cir, Winter Park, FL 32792

  Welcome to this beautifully maintained townhome located in the heart of Winter Park, Florida. From the moment you arrive, the charming exterior draws you in with its classic stucco finish, attached one-car garage, manicured landscaping, and a welcoming shaded entry framing the front door. Step inside to an inviting foyer featuring high ceilings, modern lighting, and a striking staircase that sets

  Daniel Lennon LPT REALTY LLC

  2521 Galliano Cir, Winter Park, FL 32792
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  $549,000

  Open Sun 1PM - 4PM $66K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft

  4392 Wardell Place Unit 201, Orlando, FL 32814

  SIGNIFICANT PRICE IMPORVEMENT!! This exquisite second-floor condo is a rare corner unit beautifully nestled in the heart of Baldwin Park. Boasting 1,434 square feet of living space, the home features a spacious open floor plan with impressive high ceilings and stunning natural light and a wrap-around porch. Brand new luxury vinyl floors run throughout the entire home, which includes three

  Brian Cirillo BALDWIN PARK REALTY LLC

  4392 Wardell Place Unit 201, Orlando, FL 32814
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  $2,950,000

  • 5 Beds
  • 5.5 Baths
  • 3,501 Sq Ft

  1236 Chichester St, Orlando, FL 32803

  Fresh, inspired design defines this distinctive residence in the coveted Beverly Shores/Rose Isle neighborhood, thoughtfully created with an emphasis on craftsmanship, natural materials & spaces that flow beautifully from one to the next. The foyer makes an immediate impression with custom herringbone-pattern white oak flooring, a tailored wainscot accent wall & white oak-cased openings that draw

  Lisa Shear FANNIE HILLMAN & ASSOCIATES

  1236 Chichester St, Orlando, FL 32803
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  $950,000

  • 3 Beds
  • 3 Baths
  • 2,586 Sq Ft

  2425 Lake Sue Dr, Orlando, FL 32803

  Opportunity awaits in the Beeman Park neighborhood, with access to the beautiful Lake Sue. This classic mid-century home features 3 bedrooms and 3 bathrooms spread across multiple levels, offering a unique layout with excellent potential for renovation, restoration, or complete reimagining.The property requires repairs and updates, making it an ideal project for investors, contractors, or

  Sandy Fox CHARLES RUTENBERG REALTY ORLANDO

  2425 Lake Sue Dr, Orlando, FL 32803
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  $2,995,000

  New Construction

  • 5 Beds
  • 6 Baths
  • 3,689 Sq Ft

  1204 Nottingham St, Orlando, FL 32803

  A REFINED CUSTOM SINGLE-STORY RESIDENCE WITH CASITA BY M. LAHR HOMES! Located in the highly sought-after Beverly Shores / Rose Isle neighborhood of Orlando / Winter Park, this newly completed custom residence represents a rare opportunity in one of Central Florida’s most desirable and seldom-available areas. This home reflects the level of craftsmanship, detail, and execution that has made the

  Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  1204 Nottingham St, Orlando, FL 32803
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  $998,500

  $97K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,349 Sq Ft

  505 Westminster St, Orlando, FL 32803

  BUYER FINANCING FELL THROUGH! Here's your chance... Stunning Renovation in the Heart of Orwin Manor | $1,095,000 | 3 BD | 3 BA | 2,349 SFA rare find in one of Winter Park's most sought-after neighborhoods, this beautifully reimagined 1947 estate blends the character of a classic home with the quality of brand-new construction. Renovated by the celebrated Maroon Fine Homes, every inch of its

  Kelly Price KELLY PRICE & COMPANY LLC

  505 Westminster St, Orlando, FL 32803
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  $2,395,000

  $95K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 3,982 Sq Ft

  2656 Meeting Place, Orlando, FL 32814

  Set along one of Baldwin Park's most desirable park-facing streets, this fully reimagined five-bedroom, five-bath residence provides a rare blend of space, design, and lifestyle just moments from the charm of Winter Park. Spanning nearly 4,000 square feet, the home has been thoughtfully renovated with high-end custom finishes and a modern transitional aesthetic that feels both elevated and

  Chocky Burks CORCORAN PREMIER REALTY

  2656 Meeting Place, Orlando, FL 32814
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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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  $449,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,128 Sq Ft

  3365 Pelham Rd, Orlando, FL 32803

  Nestled in the highly sought-after Orwin Manor neighborhood, this charming 3-bedroom, 2-bath home offers the perfect blend of character, comfort, and opportunity. Whether you're searching for a move-in ready home, an investment property, or the ideal location to build your custom dream home, this property delivers exceptional flexibility in one of Orlando's most desirable

  Tiffany Yates COMPASS FLORIDA LLC

  3365 Pelham Rd, Orlando, FL 32803
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  /21

  $834,900

  • 3 Beds
  • 2 Baths
  • 1,959 Sq Ft

  2624 Tuscarora Trail, Maitland, FL 32751

  Discover a rare waterfront, pool-home in the desirable Dommerich Hills neighborhood. This exceptional property offers the ideal combination of family-friendly living, modern convenience, and breathtaking natural beauty.The open floor plan welcomes you with vaulted ceilings and natural light in the living room, dining room, kitchen, and family room. Bamboo flooring enhances the bedrooms and

  Lori Wall EXP REALTY LLC

  2624 Tuscarora Trail, Maitland, FL 32751

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