Winter Park, FL Homes for Sale

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  /89

  $950,000

  • 4 Beds
  • 3.5 Baths
  • 3,074 Sq Ft

  4107 Gabriella Ln, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Do you have a vision? Do you love Nature? Welcome to this Exceptional Bear Gully Lakefront Retreat – A Rare Blend of Privacy and Natural Beauty! Refurbish the house as it is, or start new on this amazing rare natural Florida lakefront ground. Tucked away on the serene shores of Bear Gully Lake, this one-of-a-kind property presents a rare

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  (321) 382-1061

  4107 Gabriella Ln, Winter Park, FL 32792
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  Explore Winter Park

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  /43

  $864,900

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft

  1090 Wildmeadow Run, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. This luxurious Modern Style home delivers the pinnacle lifestyle, in every aspect of MAINTENANCE FREE LIVING. You will enjoy premium views of nature with a RESORT CLUBHOUSE featuring an abundance of amenities including a resort pool, fitness center & playground, all JUST 250 FEET AWAY....This home has been IMPECCABLY MAINTAINED, and includes the

  

  Rod Chevalier

  BHHS FLORIDA REALTY

  (321) 339-2639

  1090 Wildmeadow Run, Winter Park, FL 32792
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  /34

  $119,000

  • 2 Beds
  • 2.5 Baths
  • 1,085 Sq Ft

  3002 George Mason Ave Unit 3, Winter Park, FL 32792

  Tucked away in Winter Park setting, this well-maintained 2-bedroom, 2.5-bathroom condo offers a blend of privacy and convenience. Enjoy quiet moments on the porch or the private balcony off the primary suite. The thoughtful layout features main living areas and a half bath on the first floor, with both bedrooms and two full baths upstairs for comfort and separation. Ideally located just minutes

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  (321) 399-7359

  3002 George Mason Ave Unit 3, Winter Park, FL 32792
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  /19

  $180,000

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792

  Well maintained 2 bedroom/2 bathroom condo located in Lancelot of Winter Park. This spacious second floor unit with large windows brings in plenty of natural light. The main living areas have wood laminate tile flooring and granite countertops in the kitchen. The bathrooms have been updated with sleek fixtures, modern design elements and newly painted. Nearby, you will find top rated schools and

  

  Monica Perlas

  COLDWELL BANKER REALTY

  (321) 449-2749

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792
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  /50

  $469,900

  • 3 Beds
  • 3 Baths
  • 1,880 Sq Ft

  2835 Bongart Rd, Winter Park, FL 32792

  Seller is Motivated and open to incentives, must sell NOW! - Welcome to your spectacular pool home in Winter Park Estates. This beautifully renovated 3-bedroom, 3-bath residence features all the modern upgrades you've been searching for inside and out! Enjoy peace of mind with a new A/C unit (warranty included) and resurfaced pool complete with a new pump—perfect for Florida living. The backyard

  

  Claudia Jenkins

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 450-7314

  2835 Bongart Rd, Winter Park, FL 32792
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  /53

  $720,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,497 Sq Ft

  3018 Carmello Ave, Orlando, FL 32814

  Welcome to your dream home in the heart of Baldwin Park, a highly sought-after community known for its charm and convenience. This exquisite single-story residence, inspired by Monticello French style, offers a perfect blend of elegance and modern living. With 3 spacious bedrooms, 2 well-appointed bathrooms, and a 2-car garage, this home is designed for both comfort and functionality.Step

  

  Angela Carney

  CORCORAN PREMIER REALTY

  (321) 895-9273

  3018 Carmello Ave, Orlando, FL 32814
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  /19

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7706 Country Place Unit A8, Winter Park, FL 32792

  Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining

  

  Carmen Vazquez

  REALTY TECH INC

  (321) 339-0107

  7706 Country Place Unit A8, Winter Park, FL 32792
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  /15

  $189,900

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit B216, Winter Park, FL 32789

  Lovely 3 bedroom 2 bathroom second floor unit at Waterfall Cove in the heart of Winter Park, close to shopping, restaurants, schools and major roadways. The end unit features a nice open floorplan with lots of natural light. The kitchen is spacious and has lots of cabinet storage and countertop space it overlooks the large living room with sliding glass doors that lead out to the balcony with a

  

  Martha Grasty

  RE/MAX ASSURED

  (321) 381-3262

  1695 Lee Rd Unit B216, Winter Park, FL 32789
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  /8

  $260,000

  • Land
  • 0.81 Acre
  • $320,988 per Acre

  3580 Wilde Ave, Winter Park, FL 32792

  Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just shy of an acre, lot in coveted Winter Park. Nestled on a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level lot on a

  

  Gwendolen Flynn

  COLDWELL BANKER RESIDENTIAL RE

  (321) 334-2867

  3580 Wilde Ave, Winter Park, FL 32792
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  /42

  $765,000

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft

  2418 Whitehall Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. MAJOR PRICE REDUCTION! MOTIVATED SELLER! Don't miss out!!! A true GEM located in the highly desirable Brookshire Heights, presenting this FULLY REMODELED spacious single-story property in the heart of WINTER PARK. Showcasing a new meticulously designed floorplan, this property has also recently been EXTENDED by a total approx. 1,040 sqft. Exuding

  

  Alice Anne Jackson

  CORCORAN PREMIER REALTY

  (321) 599-7240

  2418 Whitehall Cir, Winter Park, FL 32792
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  /39

  $699,000

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft

  2338 Tuscarora Trail, Maitland, FL 32751

  ***Charming Dommerich Hills Home with Scenic Lake Views and Modern Updates*** Nestled in the desirable Dommerich Hills, this beautiful 4-bedroom, 2-bath lakeside home offers a serene lifestyle with views of the lush conservation area and Lake Waumpi. Mature trees and an expansive backyard create a peaceful retreat, with ample space to add a pool. The home’s classic Florida charm is enhanced with

  

  Timothy Smith

  WHITE WHALE REAL ESTATE

  (321) 329-6311

  2338 Tuscarora Trail, Maitland, FL 32751
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  /59

  $1,475,000

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

  690 Osceola Ave Unit 604, Winter Park, FL 32789

  Gorgeous Lakefront 2-Story Winter Park Penthouse, corner builder’s unit with panoramic views of Lake Virginia from almost every room and its expansive full-width balcony. Welcome to Lakefront Luxury Living in the heart of Winter Park. This extraordinary Penthouse residence on the Chain of Lakes perfectly captures the essence of opulent Florida living. The 2-story lakefront home offers an

  Larry Slung COLDWELL BANKER RESIDENTIAL RE

  690 Osceola Ave Unit 604, Winter Park, FL 32789
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  /35

  $770,000

  • 5 Beds
  • 4 Baths
  • 2,866 Sq Ft

  5618 Winterbrook Way, Winter Park, FL 32792

  PRICE IMPROVEMENT - THIS HOME IS TRULY A MUST SEE! This stunning 5-bed, 4-bath home in the exclusive gated WINTERBROOK community is move in ready and ready for you to enjoy. Built in 2020 by Pulte Homes, this like new energy-efficient home offers luxury wood-look tile, wood beams, a 2 car garage with epoxy floors and a beautifully landscaped backyard. The gourmet kitchen features quartzite

  Elizabeth Binder REDFIN CORPORATION

  5618 Winterbrook Way, Winter Park, FL 32792
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  /28

  $649,900

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789

  Rare opportunity to own a first floor unit with soaring 9 foot ceilings only steps away from the prestegious Park Avenue! Discover the perfect blend of luxury, comfort, and convenience with this immaculate, move-in-ready condo, in the heart of Winter Park. Recently transformed with meticulous attention to detail, this lock-and-leave gem boasts an elegant, high-end renovation that exudes

  Jonathan Ruiz KELLER WILLIAMS WINTER PARK

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789
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  /20

  $265,000

  • 2 Beds
  • 2.5 Baths
  • 1,295 Sq Ft

  2394 Sun Valley Cir, Winter Park, FL 32792

  This charming 2-bedroom, 2-bathroom condo offers 1,295 square feet of comfortable single-level living, thoughtfully designed for easy living and entertaining. The open floor plan boasts a spacious, sunlit living area and a well-appointed kitchen, perfect for culinary creations. Both bedrooms are generously sized and provide privacy, each featuring its own en-suite bathroom for added convenience.

  Jamie Vanosdol EXP REALTY LLC

  2394 Sun Valley Cir, Winter Park, FL 32792
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  /24

  $100,000

  • 2 Beds
  • 1.5 Baths
  • 1,085 Sq Ft

  126 Scottsdale Square Unit B126, Winter Park, FL 32792

  Great location!! Discover the charm of this beautifully maintained condo at 126 Scottsdale Square, nestled in a serene and convenient Orlando community. This condo boasts 3 bedrooms and 2 bathrooms thoughtfully designed with a spacious layout perfect for comfortable living. From the bright and open living area to the modern kitchen with upgraded appliances. Every detail has been tailored for

  Thomas Hicks, Sr LPT REALTY, LLC

  126 Scottsdale Square Unit B126, Winter Park, FL 32792
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  /38

  $875,000

  • 4 Beds
  • 4 Baths
  • 2,759 Sq Ft

  730 S Ranger Blvd, Winter Park, FL 32792

  Stunning, one of kind, 4/4 Winter Park pool home loaded with upgrades! ROOF, AC & WATER HEATER (2020), NEW FLOORING, KITCHEN & BATHS (2025), QUARTZ COUNTER TOPS (2025) FRESH INTERIOR PAINT (2025) & EXTERIOR (2023). Enjoy NEW DRIVEWAY PAVERS, FRONT YARD IRRIGATION (2025), REPLACEMENT WINDOWS & FRENCH DOORS (2016). Largest old school POOL in the neighborhood (20x40) RESURFACED (2016) with NEW PUMP

  David Knight EXP REALTY LLC

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

  $400,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,071 Sq Ft

  2320 High St, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Enjoy a 1% lower interest rate for your first year with our preferred lender! Located in the highly sought after Winter Park area, this home features 3 Bedrooms, 2 Bathrooms was thoughtfully renovated in 2025 by the current owner. Perfect for a first time homebuyer or investor looking for a move-in ready, low maintenance property! Updates include a

  Jessica Lee THE AGENCY ORLANDO

  2320 High St, Winter Park, FL 32792
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  /72

  $945,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 3 Baths
  • 2,456 Sq Ft

  915 Garden Dr, Winter Park, FL 32789

  Step into this beautifully maintained Mid-Century Modern home, nestled in the prestigious Winter Park community and just a short three-minute stroll to the serene beauty of Mead Botanical Garden. A true raised ranch design, this home radiates warmth and character from the moment you arrive, featuring an expansive covered front patio that welcomes you inside.Inside, you’ll be greeted by

  Cassie Lamoureux KELLER WILLIAMS CLASSIC

  915 Garden Dr, Winter Park, FL 32789
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  /32

  $465,000

  • 5 Beds
  • 3 Baths
  • 1,442 Sq Ft

  2181 Linden Rd, Winter Park, FL 32792

  Discover this beautifully remodeled home at 2181 Linden Road, located in the heart of Winter Park. With 5 bedrooms and 3 bathrooms, this property features modern upgrades throughout, including a brand-new kitchen, updated bathrooms, and fresh finishes. Nestled on a spacious lot with no HOA, it offers both privacy and flexibility for homeowners seeking comfort and style.Enjoy living just

  Alejandro Rodriguez AROD PARTNERS REALTY

  2181 Linden Rd, Winter Park, FL 32792
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  /41

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,263 Sq Ft

  5331 Oak Ct, Winter Park, FL 32792

  Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to

  Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

  5331 Oak Ct, Winter Park, FL 32792
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  /44

  $3,499,999

  • 5 Beds
  • 5.5 Baths
  • 4,955 Sq Ft

  1761 Legion Dr, Winter Park, FL 32789

  One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly

  Kelly Price KELLY PRICE & COMPANY LLC

  1761 Legion Dr, Winter Park, FL 32789
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  /77

  $2,900,000

  • 4 Beds
  • 7 Baths
  • 5,416 Sq Ft

  1401 Green Cove Rd, Winter Park, FL 32789

  This award-winning Tuscan Mediterranean residence seamlessly blends timeless architecture with a light-filled, open interior, situated on a spacious corner lot just moments from Park Avenue. From the moment you step into the grand foyer—with its graceful circular staircase, custom tile work, and rich wood floors—it's clear that every detail of this home was crafted with care.The heart of

  Terry Yonker BUCKEYE REALTY LLC

  1401 Green Cove Rd, Winter Park, FL 32789
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  /37

  $950,000

  • 3 Beds
  • 3.5 Baths
  • 2,116 Sq Ft

  1251 Arlington Place, Winter Park, FL 32789

  STUNNING WINTER PARK TOWNHOME - NO HOA, DESIGNER KITCHEN, PRIVATE BACKYARD OASISWelcome to this rare gem in the heart of Winter Park — a beautifully updated 3-bedroom, 3.5-bath townhome that lives like a single-family home WITH NO HOA! From the moment you walk in, you’ll be impressed by 20-FOOT CEILINGS in the foyer and family room, elegant hardwood floors, and OVERSIZED 8.5-FOOT DOORS

  Brad Barnett ANNE ROGERS REALTY GROUP INC

  1251 Arlington Place, Winter Park, FL 32789
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  /85

  $1,549,000

  • 5 Beds
  • 4.5 Baths
  • 5,329 Sq Ft

  8041 Lake Waunatta Dr, Winter Park, FL 32792

  Modern Lakefront Dream home NOW AVAILABLE! Nestled in the peaceful Lake Waunatta Woods neighborhood, this stunning renovated lakefront estate seamlessly blends modern style with effortless luxury. With over 5,300 square feet, five spacious bedrooms, and breathtaking panoramic views of Lake Waunatta from nearly every room, this one-of-a-kind property offers the ultimate waterfront lifestyle.

  Kathryn Stelljes KELLER WILLIAMS REALTY AT THE PARKS

  8041 Lake Waunatta Dr, Winter Park, FL 32792
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  /48

  $2,150,000

  • 5 Beds
  • 4.5 Baths
  • 3,851 Sq Ft

  1560 Woodland Ave, Winter Park, FL 32789

  You have arrived to 1560 Woodland Avenue, a beautiful home in a prime location inside the Winter Park municipality, situated on a peaceful brick-paved street. There are five bedrooms and four and a half bathrooms spread out over 3,800 square feet in this stunning property. Featuring a welcoming pool and relaxing spa. A separate suite with its own entrance is available for use by the mother-in-law

  Manny Alvarez LOKATION

  1560 Woodland Ave, Winter Park, FL 32789
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  /42

  $430,000

  • 4 Beds
  • 2 Baths
  • 1,821 Sq Ft

  2829 Aloma Ave, Winter Park, FL 32792

  Rare Opportunity in Highly Sought-After Winter Park!Don’t miss your chance to own this fantastic ...LISTED WELL BELOW APPRAISED VALUE ! Known for its top-rated schools and unbeatable location as well , this home exudes timeless charm with elegant terrazzo floors throughout. Newer Roof ( 2021) and Newer A/C ( 2019) Too!Step inside to a spacious and inviting layout, featuring a

  Cassie Lamoureux KELLER WILLIAMS CLASSIC

  2829 Aloma Ave, Winter Park, FL 32792
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  /32

  $899,000 Open Sat 1PM - 4PM

  • 5 Beds
  • 4 Baths
  • 3,424 Sq Ft

  2604 Marble Ave, Orlando, FL 32803

  Stunning 5 BEDROOM POOL HOME in the Heart of AUDUBON PARK GARDEN DISTRICT. Welcome to 2604 Marble Avenue — a beautifully appointed 5-bedroom, 4-bathroom home offering 3,424 SQUARE FEET of stylish living space in one of Orlando's most desirable neighborhoods. Zoned for top-rated AUDUBON PARK K-8 and WINTER PARK HIGH SCHOOL, this home combines location, comfort, and exceptional versatility.

  Brian Spain LAKESIDE REALTY

  2604 Marble Ave, Orlando, FL 32803
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  /28

  $320,000

  • 2 Beds
  • 2 Baths
  • 1,004 Sq Ft

  2411 Gallery View Dr Unit 103, Winter Park, FL 32792

  FIRST-FLOOR LIVING WITH DIRECT WATER VIEWS AND AN UNBEATABLE LOCATION! Located in one of Winter Park’s most convenient and cared-for communities, The Gallery at Winter Park. This 2-bedroom, 2-bath condo showcases a beautifully updated kitchen and refreshed bathrooms. Contemporary luxury vinyl floors extend across the bedrooms and living areas for a clean, cohesive look. The primary suite is at

  Maria Elena Perez MEP REALTY INVESTMENTS LLC

  2411 Gallery View Dr Unit 103, Winter Park, FL 32792
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  /20

  $210,000

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  103 Lewfield Cir Unit 103, Winter Park, FL 32792

  Don’t miss your opportunity to own this lovingly cared for home in beautiful Winter Park! This UPDATED 2-bedroom, 2-bath condo is just minutes from the vibrant downtown area with its boutique shopping, renowned restaurants, museums, colleges, boat tours, and more. Located on the first floor with NO STAIRS, this home offers numerous UPGRADES, including: energy-efficient double-pane windows and

  Jim Chuba CHARLES RUTENBERG REALTY ORLANDO

  103 Lewfield Cir Unit 103, Winter Park, FL 32792
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  /56

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 2,565 Sq Ft

  215 Salvador Square, Winter Park, FL 32789

  Welcome home to this lovely four-bedroom, three-and-a-half-bath pool home in the prestigious Sevilla neighborhood of Winter Park! Tucked off a charming brick-lined street just 1⁄4 mile from Park Avenue, this .40-acre property offers both privacy and convenience to your Winter Park lifestyle. Inside, you’ll find timeless details such as marble and parquet flooring, crown molding, plantation

  Carrie Bantel PREMIER SOTHEBY'S INTL. REALTY

  215 Salvador Square, Winter Park, FL 32789
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  /23

  $318,000

  • 2 Beds
  • 2 Baths
  • 1,457 Sq Ft

  2458 Grand Teton Cir, Winter Park, FL 32792

  Welcome to your dream home in Winter Park! This beautifully updated, spacious two-bedroom condo is nestled in the highly sought-after Cedarwood Village Condominium, a well-maintained community known for its charm and appeal. Meticulously cared for, this residence boasts modern elegance with gleaming quartz countertops and premium flooring throughout. The master suite is a true retreat, featuring

  Bryce Jones CHARLES RUTENBERG REALTY ORLANDO

  2458 Grand Teton Cir, Winter Park, FL 32792
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  /2

  $1,690,000

  • 2 Beds
  • 1 Bath
  • 1,559 Sq Ft

  141 W Lake Sue Ave, Winter Park, FL 32789

  AMAZING Winter Park Opportunity! Nestled in one of the most desirable locations, 141 W Lake Sue Avenue offers a VERY HARD to find 1⁄2 acre lot—the epitome of prime real estate. The true value lies in the land, making this a rare chance for builders or buyers to create their dream Winter Park residence. Surrounded by beautiful homes and tree-lined streets, this pristine lot provides the perfect

  Brian Mitnik RE/MAX 200 REALTY

  141 W Lake Sue Ave, Winter Park, FL 32789
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  /51

  $1,285,000

  • 4 Beds
  • 2 Baths
  • 2,750 Sq Ft

  1981 Blue Ridge Rd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**Welcome home to this beautifully renovated 4-bedroom, 2-bathroom home nestled on a desirable corner lot in the heart of Winter Park’s Timberlane Shores community. Boasting

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1981 Blue Ridge Rd, Winter Park, FL 32789
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  /50

  $1,050,000 Open Sun 2PM - 4PM

  • 5 Beds
  • 3 Baths
  • 3,858 Sq Ft

  7706 Waunatta Ct, Winter Park, FL 32792

  Stunning Lakefront Retreat in Winter Park! Welcome to your dream home on beautiful Lake Waunatta! This spacious and upgraded 5-bedroom/1-office/3-bathroom lakefront property offers over 3,850 sq. ft. of living space (5,113 sq. ft. total) on a nearly half-acre lot with ~100 feet of private shoreline. Enjoy breathtaking lake views from multiple rooms and the balcony. Open floorplan offers flexible

  Robert Arnold SAND DOLLAR REALTY GROUP INC

  7706 Waunatta Ct, Winter Park, FL 32792
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  /32

  $829,000

  • 4 Beds
  • 3.5 Baths
  • 3,062 Sq Ft

  675 Overspin Dr, Winter Park, FL 32789

  Seller may consider buyer concessions if made in an offer ~ Beautiful upgrades, a versatile layout, and the best of Winter Park at your doorstep! With Dubsdread Golf Course just around the corner and Fairbanks Avenue minutes away, this 4-bedroom, 3.5-bath CUSTOM BUILT HOME puts you in the center of it all – NO HOA required! Major systems have been well maintained; including a NEW A/C UNIT with UV

  Jennifer Wemert WEMERT GROUP REALTY LLC

  675 Overspin Dr, Winter Park, FL 32789
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  /53

  $469,000

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft

  1447 Broad Wing Ln, Winter Park, FL 32792

  This 3-bedroom, 2.5-bath townhome combines style, functionality, and low-maintenance living and is ready for you to move right in.It features a paver driveway and walkway framed by lush landscaping. As you step inside the home, you will find a versatile flex space, which is perfect as a home office, or additional living room.The main level boasts soaring 9+ foot ceilings. The

  Gaelle Cenord FOWLKES REALTY CO

  1447 Broad Wing Ln, Winter Park, FL 32792
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  /52

  $893,000

  • 5 Beds
  • 3 Baths
  • 2,242 Sq Ft

  1927 Eland Ave, Winter Park, FL 32789

  Tucked away on a quiet dead-end street with no rear neighbors, 1927 Eland Avenue combines charm, versatility, and an unbeatable Winter Park lifestyle. This beautifully maintained property offers both a character-filled main home and a modern detached in-law suite.The main residence features 3 bedrooms, 2 bathrooms, real wood floors, abundant natural light, and warm Spanish Colonial

  Adriana Gonzalez PERFECT INVESTMENT REALTY

  1927 Eland Ave, Winter Park, FL 32789
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  /35

  $210,000 Open Sat 12PM - 2PM

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  2500 Lee Rd Unit 219, Winter Park, FL 32789

  Welcome to life on Lake Killarney, one of Winter Park’s most sought-after lakefront communities! This charming 2-bedroom, 1-bathroom condo offers an unbeatable location and resort-style amenities—perfect for those seeking the true Florida lifestyle.Enjoy direct access to Lake Killarney, where residents can take advantage of boat slips available at a low cost on a first-come, first-serve basis, as

  Nicole Van Treese SUNDIAL REAL ESTATE LLC

  2500 Lee Rd Unit 219, Winter Park, FL 32789
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  /55

  $990,000

  • 4 Beds
  • 3.5 Baths
  • 2,173 Sq Ft

  208 Brewer Ave, Winter Park, FL 32789

  SELLERS ARE OFFERING $10,000 BUYER CLOSING COST CONCESSION FOR ANY BUYER WITH AN ACCEPTED CONTRACT BY 8/31/25. A $5,000 CREDIT TO A BUYER FOR AN ACCEPTED CONTRACT BY 09/30/25! Welcome to this beautifully updated 4-bedroom, 3.5-bath Craftsman-style home, offering just under 2,200 sq ft of thoughtfully designed living space. From the moment you arrive, the charm is undeniable—with classic

  Cassandra King COMPASS FLORIDA LLC

  208 Brewer Ave, Winter Park, FL 32789

Showing Results 1 - 40, Page 1 of 10

Why Live in Winter Park

Winter Park, located near Orlando, Florida, began in the 1880s as a planned community appealing to northern ex-pats with its warm winters, good schools, and lively arts scene. Today, it maintains its "City of Arts and Culture" nickname with museums and a vibrant cultural atmosphere. The main commercial district, Park Avenue, features high-end boutiques and bistros, including The Ravenous Pig, a renowned gastropub. Rollins College and The Rollins Museum of Art are local highlights, along with The Alfond Inn, which serves as a social hub. The city’s nearly 30,000 residents enjoy highly rated schools such as Winter Park High and Trinity Preparatory School of Florida. Housing options range from petite bungalows to lakeside mansions, with styles including New Traditional, midcentury-era ranch homes, Colonial Revival, and Contemporary homes. The Winter Park Chain of Lakes offers boating, kayaking, and paddleboarding opportunities, while Central Park provides 11 acres of green space with walking paths and a rose garden. Annual events like the Winter Park Sidewalk Arts Festival and Christmas on Park attract visitors and foster community spirit. Residents have access to Interstate 4, SunRail, and Lynx buses for transportation, with Orlando International Airport about 20 miles away. Winter Park’s crime rates are lower than the national average, making it a safer area compared to nearby Orlando.

Learn more about living in Winter Park

Frequently Asked Questions

What is the average home price in Winter Park, FL?

Homes for sale in Winter Park, FL have an average home price of $952,655.

How many homes have sold over the last 12 months in Winter Park, FL?

1,027 homes have sold in Winter Park, FL over the last 12 months.

What are the most popular zip codes in Winter Park, FL?

The most popular zip codes in Winter Park, FL include 32789, 32792, 32751, 32803 and 32814.

How much do you need to make to afford a house in Winter Park?

The median home price in Winter Park is $525,000. If you put a 20% down payment of $105,000 and had a 30-year fixed mortgage with an interest rate of 6.56%, your estimated principal and interest payment would be $2,670 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $114K a year to afford the median home price in Winter Park.

How are the schools in Winter Park, FL?

Winter Park, FL has highly rated public and private schools. Some of the best schools in Winter Park based on Niche Grades are Trinity Preparatory School, Audubon Park School and Baldwin Park Elementary. Browse all the schools in Winter Park, FL to learn more.

Home Trends in Winter Park, FL

On average, homes in Winter Park, FL sell after 62 days on the market compared to the national average of 52 days. The median sale price for homes in Winter Park, FL over the last 12 months is $480,000, up 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$480,000

Median Single Family Sale Price

$610,000

Median Townhouse Sale Price

$474,000

Median 2 Bedroom Sale Price

$220,000

Median 1 Bedroom Sale Price

$155,000

Average Price Per Sq Ft

$369

Number of Homes for Sale

303

Last 12 months Home Sales

1,027

Months of Supply

3.50

Median List Price

$525,000

Median Change From 1st List Price

5%

Median Home Sale Price YoY Change

2%