Winter Park, FL Homes for Sale with Garage

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  $1,200,000

  • 3 Beds
  • 2 Baths
  • 2,158 Sq Ft

  1600 S Pennsylvania Ave, Winter Park, FL 32789

  Welcome to this charming 3 bedroom, 2 bath home located in the highly desirable area of Winter Park. Situated on an oversized lot, this property offers both comfort and space with a layout designed for everyday living and entertaining. The home features a inviting living area along with a unique sunken sunroom just off the two-car garage; perfect for a relaxing sitting room, home office, or play

  Jami Giles EXIT REAL ESTATE PROPERTY SOL

  1600 S Pennsylvania Ave, Winter Park, FL 32789
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  /44

  $549,000

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  1809 Hammerlin Ave, Winter Park, FL 32789

  Highly coveted Winter Park! 40+ Pictures! This stunning 2-story end unit offers the epitome of modern convenience and elegant living; this residence provides the ideal "lock and go" lifestyle. Step through the charming covered front porch into the inviting open living area, adorned with abundant natural light, gleaming real wood flooring, and exquisite crown molding. Hosting gatherings is

  Edward Rice NICOLE-HUDSON REALTY CORP

  1809 Hammerlin Ave, Winter Park, FL 32789
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  /70

  $1,634,900 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft

  1510 Miller Ave, Winter Park, FL 32789

  New Construction – Carefully Curated by SGC Conctruction. Discover Modern Luxury in Winter Park's Latest Neighborhood, Winter Park Grove! Step into a world of refined living with this breathtaking new construction pool home, located in the vibrant heart of Winter Park. Just moments away from the eclectic energy of Park Avenue, this modern masterpiece seamlessly blends sophistication, style, and

  Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  1510 Miller Ave, Winter Park, FL 32789
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  /2

  $1,495,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,756 Sq Ft

  905 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. 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. Ideally located within walking distance to Park Avenue and historic Old Winter Park, this exclusive neighborhood blends timeless character with modern luxury. The

  Matthew Burks CORCORAN PREMIER REALTY

  905 Enclave Place, Winter Park, FL 32792
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  /55

  $1,399,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,984 Sq Ft

  1540 Miller Ave, Winter Park, FL 32789

  Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by SGC Construction! This stunning new Mid-Century Modern–inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shopping, dining, and entertainment Winter Park is famous for, this home combines

  Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  1540 Miller Ave, Winter Park, FL 32789
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  /18

  $625,000

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  1760 Greenwich Ave, Winter Park, FL 32789

  Fabulous Winter Park location. This is a 3 bedroom, 2 bath patio home with a great layout, split bedroom plan, high ceilings in the living room, and an eat in kitchen that is open to the family room. A large primary bedroom which has a walk in closet, two additional closets and french doors leading out to the back yard. There is a screened in patio off of the breakfast / dining area and an

  Meg Dolan FANNIE HILLMAN & ASSOCIATES

  1760 Greenwich Ave, Winter Park, FL 32789
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  /9

  $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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  /43

  $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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  /3

  $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. 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 intention, The Enclave offers a rare opportunity to enjoy a

  Matthew Burks CORCORAN PREMIER REALTY

  914 Enclave Place, Winter Park, FL 32792
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  /39

  $3,350,000

  • 5 Beds
  • 6 Baths
  • 4,636 Sq Ft

  2040 Randall Cir, Winter Park, FL 32789

  Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2040 Randall Cir, Winter Park, FL 32789
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  /2

  $1,495,000 New Construction

  • 3 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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  /10

  $1,689,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft

  1810 Hollywood Ave, Winter Park, FL 32789

  Under Construction. Estimated completion August!! Experience modern luxury living in the heart of Winter Park with this beautifully designed pool home at 1810 Hollywood Avenue. Offering 4 bedrooms, 3.5 bathrooms, and 2,604 square feet of thoughtfully planned living space, this residence blends high-end finishes with everyday functionality in one of Central Florida’s most sought-after locations.

  Ken Pozek REAL BROKER, LLC

  1810 Hollywood Ave, Winter Park, FL 32789
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  /31

  $485,000

  • 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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  /73

  $3,449,999

  • 4 Beds
  • 5 Baths
  • 3,658 Sq Ft

  1742 Temple Dr, Winter Park, FL 32789

  A New Standard of Modern Sophistication in Winter ParkIn a city known for its heritage, this ground-up architectural renovation emerges as a bold statement of modern luxury. Located within one of Winter Park’s most coveted enclaves, this four-bedroom, five-bathroom residence is not merely a place to live, but a meticulously crafted experience where high-design meets intuitive living.Step

  Mark Anthony Buot ROI AVE LLC

  1742 Temple Dr, Winter Park, FL 32789
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  /44

  $1,160,000

  • 4 Beds
  • 3 Baths
  • 2,597 Sq Ft

  2232 Banchory Rd, Winter Park, FL 32792

  Step into the Winter Park lifestyle with a fully turnkey home designed to make daily living feel effortless. Set on an oversized corner lot, this fully updated home blends clean design with thoughtful upgrades.Inside, the home is built to bring people together. The open-concept layout flows seamlessly from living to dining to kitchen, anchored by a striking 9-foot Carrera Thassos quartz

  Kirstie Hines PREMIER SOTHEBY'S INTL. REALTY

  2232 Banchory Rd, Winter Park, FL 32792
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  /5

  $4,200,000 New Construction

  • 5 Beds
  • 7 Baths
  • 5,500 Sq Ft

  141 W Lake Sue Ave, Winter Park, FL 32789

  Pre-Construction. To be built. A Generational Opportunity in the Heart of Winter Park Presenting an exceptionally rare opportunity to build a fully custom luxury estate on one of Winter Park’s most extraordinary homesites. Situated on an expansive 1/2-acre corner lot, an offering virtually unheard of in this coveted location, this property represents the pinnacle of luxury new construction

  Brian Hyser THE AGENCY FL

  141 W Lake Sue Ave, Winter Park, FL 32789
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  /55

  $2,650,000

  • 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 six-bedroom, three-and-a-half-bath main home—featuring one bedroom currently used as a private office—plus a detached 384 SF casita (seventh bedroom) sits on a

  Gwyn Clark FANNIE HILLMAN & ASSOCIATES

  1411 Nottingham St, Orlando, FL 32803
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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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  /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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  /13

  $550,000

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

  210 Alpine Dr, Maitland, FL 32751

  Don't miss this Great opportunity in the Maitland-Winter Park area! There's Potential for Renovation, Expansion or Development with this property. Imagine the Improvements that can be made for the Future. This is a One Owner Home held be the same family since the 1960s. New roof in 2022. The adjacent property at 220 Alpine is also available for purchase.

  Beth Hathaway PREMIUM PROPERTIES R.E SERVICE

  210 Alpine Dr, Maitland, FL 32751
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  /30

  $500,000

  • 3 Beds
  • 2 Baths
  • 1,707 Sq Ft

  612 Green Meadow Ave, Maitland, FL 32751

  Welcome to a home that doesn’t just check boxes — it supports your lifestyle. Tucked into one of Maitland’s beloved neighborhoods, Forest Brook, this delightful property blends comfort, practicality, and a little everyday serenity. *Lots of new since 2023: Whole house generator, 20’x12’ shed, front and back sod (just completed 4/2026), renovated driveway, gutters, vinyl fence in backyard & so

  Stacy Wayne FLORIDA HOME TEAM REALTY LLC

  612 Green Meadow Ave, Maitland, FL 32751

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