Winter Park, FL Homes for Sale

• 

  

  

  /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
• 

  

  /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
• 

  

  

  /55

  $171,000

  • 2 Beds
  • 2 Baths
  • 927 Sq Ft

  256 Lewfield Cir Unit 256, Winter Park, FL 32792

  This charming and well-maintained 2 bedroom, second-floor condo in Winter Park is ready for you to call your own! The home features comfortable carpeted living areas throughout. The centrally located galley kitchen offers plenty of cabinet and counter space and connects directly to the dining room. The spacious living room gets plenty of natural light through large sliding glass doors, opening to

  Renee Kumar LLC LA ROSA REALTY LLC

  256 Lewfield Cir Unit 256, Winter Park, FL 32792
• 

  

  

  /25

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  1280 Gladiolas Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bath home with a New Roof 2021, screened-in pool, ideally located in the heart of Winter Park. Step inside to a fresh, move-in-ready feel with new flooring throughout, new light fixtures, new windows, and new doors—all thoughtfully selected to give the home a clean, modern look. The open, inviting

  Ian Trumbach FLORIDA PRESTIGIOUS HOMES INC

  1280 Gladiolas Dr, Winter Park, FL 32792
• 

  

  

  /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
• 

  

  /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
• 

  

  /73

  $3,549,995

  • 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
• 

  

  /28

  $739,990

  • 3 Beds
  • 2 Baths
  • 1,495 Sq Ft

  1741 Lyndale Blvd, Maitland, FL 32751

  Charming Newly Renovated Bungalow in Prime Maitland Location – Move-In Ready with Endless Potential!Discover this beautifully updated 3-bedroom, 2-bath bungalow at 1741 Lyndale Blvd, Maitland, FL 32751 – perfectly positioned on the edge of Winter Park for an unbeatable blend of tranquility and convenience. Freshly renovated and move-in ready, this home offers immediate comfort while sitting

  Matías Ugarte CHARLES RUTENBERG REALTY ORLANDO

  1741 Lyndale Blvd, Maitland, FL 32751
• 

  

  /18

  $700,000

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

  805 Nottingham St, Orlando, FL 32803

  One or more photo(s) has been virtually staged. Fully Renovated Orwin Manor Home | High-End Finishes | Major Systems Updated Located in desirable Orwin Manor, ideally positioned between the charm of College Park and the shopping, dining, and cultural destinations of Park Avenue, this fully renovated residence blends timeless character with high-end modern upgrades. The home has undergone an

  Anna Snyder CFL REAL ESTATE LLC

  805 Nottingham St, Orlando, FL 32803
• 

  

  /37

  $789,000

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  2514 Tuscarora Trail, Maitland, FL 32751

  Seller $10,000 Credit to Buyer “Discover the advantage of owning one of Tuscarora Trail’s premier homesites—where space, privacy, and lifestyle come together, all within the highly sought-after Dommerich school district, supporting both today’s living and tomorrow’s resale value. ” Nestled on a serene lakeside setting in the heart of Maitland, this beautifully upgraded 4-bedroom, 2.5-bath home

  Tom Noelke NOELKE REALTY

  2514 Tuscarora Trail, Maitland, FL 32751
• 

  

  /47

  $2,740,000

  • 6 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
• 

  

  /31

  $784,000

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

  1732 Ridgewood Ave Unit S, Maitland, FL 32751

  This custom two-story townhome delivers what most properties in this category simply don’t; space, light, and a layout that actually makes sense. Open, airy, and thoughtfully designed, every detail feels intentional. Perfectly positioned between Maitland and Winter Park, you’re just minutes from Park Avenue, Winter Park Village, and some of the best dining and shopping in Central Florida. Step

  Brandon Geers COMPASS FLORIDA LLC

  1732 Ridgewood Ave Unit S, Maitland, FL 32751
• 

  

  /75

  $3,495,000 Open Wed 3PM - 5:30PM

  • 5 Beds
  • 5.5 Baths
  • 4,387 Sq Ft

  1208 Nottingham St, Orlando, FL 32803

  A REFINED CUSTOM RESIDENCE 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 most desirable and seldom-available areas. This home reflects the level of craftsmanship, detail, and execution that has made the builder one of the

  Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  1208 Nottingham St, Orlando, FL 32803
• 

  

  /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
• 

  

  /4

  $450,000

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft

  220 Alpine Dr, Maitland, FL 32751

  Opportunity in the Maitland / Winter Park area! This one-owner home, held by the same family since the 1960s, is ideally located near shopping, dining, parks, and major roadways, providing convenient access throughout Central Florida.The property offers potential for renovation, expansion, or redevelopment, with a lot that provides space for future improvements. Ideal for homeowners,

  Beth Hathaway PREMIUM PROPERTIES R.E SERVICE

  220 Alpine Dr, Maitland, FL 32751
• 

  

  /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
• 

  

  /34

  $615,000

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft

  4392 Wardell Place Unit 102, Orlando, FL 32814

  Welcome home to this charming, first floor, corner-unit condo in the heart of Baldwin Park! This impressive home features an oversized wrap around patio, an attached one car garage and has been fully updated throughout! Move in stress-free with a New HVAC (2022), New Paint (2022), all New Luxury Vinyl Plank Flooring throughout (2022), Brand new Refrigerator, Microwave, Range (2024), New Disposal

  Lindsey Hahn ALL REAL ESTATE & INVESTMENTS

  4392 Wardell Place Unit 102, Orlando, FL 32814

Showing Results 321 - 337, Page 9 of 9