Winter Park, FL Homes for Sale with Garage

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  $549,000

  $101K PRICE DROP

  • 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

  $1,599,900

  New Construction Open Fri 2PM - 6PM $35K PRICE DROP

  • 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

  • 4 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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  $485,000

  $15K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,656 Sq Ft

  1850 Aster Dr, Winter Park, FL 32792

  Welcome to the heart of Winter Park.This beautifully maintained 4-bedroom, 2.5-bath pool home offers the perfect blend of warmth, functionality, and charm. From the moment you arrive, the curb appeal is unforgettable. Lush landscaping, mature greenery, and peaceful natural surroundings create a private and inviting setting that immediately feels like home. Inside you'll find an open and welcoming

  Kimberly English EXP Realty, LLC

  1850 Aster Dr, 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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  /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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  $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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  /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. 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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  /34

  $750,000

  • 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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  /49

  $1,395,000

  • 4 Beds
  • 4 Baths
  • 3,046 Sq Ft

  1077 Minnesota Ave, Winter Park, FL 32789

  Location. Design. Lifestyle. Newly built in 2025 by Nautilus Homes and lightly lived in, this exceptional custom residence offers the perfect blend of modern construction, elevated design, and an unbeatable Winter Park location. Ideally positioned between Orlando Avenue and Orange Avenue, just moments from Park Avenue, Mead Botanical Garden, acclaimed dining, boutique shopping, and cultural

  Frank Benevento COLDWELL BANKER REALTY

  1077 Minnesota Ave, Winter Park, FL 32789
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  $1,275,000

  Open Sat 2PM - 5PM

  • 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 schools. From

  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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  /31

  $475,000

  $65K PRICE DROP

  • 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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  /44

  $1,115,000

  $45K PRICE DROP

  • 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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  /27

  $360,000

  Open Sun 12PM - 3PM

  • 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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  $615,000

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

  4392 Wardell Place Unit 201, Orlando, FL 32814

  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 bedrooms and two full bathrooms. The

  Brian Cirillo BALDWIN PARK REALTY LLC

  4392 Wardell Place Unit 201, Orlando, FL 32814
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  /42

  $945,000

  Open Sat 12PM - 2PM

  • 5 Beds
  • 3 Baths
  • 3,370 Sq Ft

  624 Tuscarora Trail, Maitland, FL 32751

  Welcome to this impressive 5-bedroom, 3-bath split-level POOL home in desirable Dommerich Hills, perfectly nestled on a generous 0.34-acre lot backing to a quiet creek and scenic preserve. Enjoy exceptional privacy and natural beauty with no rear neighbors, creating a peaceful backyard retreat.This remarkable residence offers almost 3400 square feet of living space, providing plenty of room

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  624 Tuscarora Trail, 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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  $1,095,000

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

  505 Westminster St, Orlando, FL 32803

  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 2,349 square feet has been thoughtfully

  Kelly Price KELLY PRICE & COMPANY LLC

  505 Westminster St, Orlando, FL 32803
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  /21

  $1,149,000

  Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,642 Sq Ft

  2506 Woodside Ave, Orlando, FL 32803

  Welcome to 2506 Woodside Ave — a meticulously appointed 2017-built home with distinctive modern architecture tucked into one of Orlando's most beloved and established neighborhoods. Clean lines, bold design, and an unmistakable contemporary presence set this home apart on a street of charming older Florida homes and newer construction alike. Surrounded by mature trees and quiet streets where

  Steven Koleno BEYCOME OF FLORIDA LLC

  2506 Woodside Ave, Orlando, FL 32803
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  /66

  $2,490,000

  Coming Soon

  • 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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  /13

  $527,300

  $23K PRICE DROP

  • 2 Beds
  • 2.5 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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