Winter Park FL. Homes For Sale

This lovely three-bedroom, two-bath landscaped home has all the best Winter Park has to offer. It is less than two blocks from Winter Park’s Central Park and Park Avenue’...

Welcome to the heart of the Vias! This 3,900+ SF home sits on a corner lot over 1/3 acres, with a circular drive, great floorplan, downstairs Master & spectacular outdoor...

Step into this newly renovated four-bedroom, three-bath, gorgeous pool home located in Winter Park's beautiful Park North neighborhood! Just steps to Park Avenue dining,...

Warm and elegant home in the heart of Winter Park just blocks away from Park Avenue, Rollins College, and across the street from Trismen Park. This completely remodeled 4...

Nice, Updated house in desirable Winter Park! New appliances, New laminate floor in bedrooms. Second bedroom with its own bathroom could be used as studio apartment with ...

Move in ready 4 bed/2 ½ bath Clayton built Parade of Homes! Only 3rd owner who meticulously updated home with designer touches throughout and added a master wing! Fabulou...

Beautiful Winter Park home built in 1955. This is a 4/2 pool home with 2,121 sf with hardwood floors throughout, and porcelain tile in the kitchen, laundry room and bathr...

Do not miss your opportunity to call this lovely 3 bedroom, 2 bathroom property in Winter Park HOME!!! This bright and airy home has a great split bedroom open floorplan....

Looking for a quiet & peaceful place, with a magnificent water view, look no further! This pristine home was custom built in 2004 by Bill Felkel and remains loved by the ...

Charm and sophistication at its finest. This landmark Kenilworth Shores home boasts 4 bedrooms, 2 full baths, and a captivating screened in heated pool. Both efficient an...

This nicely maintained traditional style home is located on the brick-paved streets of winter park within walking distance to all shops and restaurants Winter Park has to...

Pre-Construction. To be built. “Pre-Construction. To be built.” VIA VENETO is an exclusive new subdivision of four (4) oversized Lakefront Lots in Winter Park's most desi...

WELCOME HOME to the Winter Park Pines, where the mailman delivers to your door, beautiful tree lined streets, and sidewalks made for easy access around the neighborhood o...

SUPERB Location!! Come see this beautiful 2bedroom / 1bathroom with extra bonus room, BRAND NEW ROOF, newly remodel single family home. Home is located just a few minutes...

WOW! FOUR BEDROOM POOL HOME ON .44 ACRE LOT ON A QUIET CUL-DE-SAC!! This is an OUTSTANDING opportunity to own the home of your dreams!! 4 Bedroom 2 Bath split plan flo...

This four-bedroom, two-bathroom home is located in Winter Park on a cozy street bordering the College Park area just down the road from Dubsdread Golf Course. Walk up to...

Quaint updated Winter Park bungalow located at the end of a quiet brick street. This 2 bedroom 1 bathroom home features a cozy living room with original wood floors, upda...

Located in the heart of Winter Park in the well-established community of Quail Hollow! Sitting on a large corner lot, sits this charming 1-story home featuring 4 bedroo...

Your wait is over, this beautiful WINTER PARK home is calling your name!! This immaculate 4/2.5 POOL home is sitting on a beautifully maintained lot, with NO HOA. This sp...

THE MOMENT YOU DRIVE UP, YOUR HEART BEGINS TO QUICKEN. This well maintained home is more than you had hoped. Contemporary double pane windows have replaced the out dated ...

This Property Is Move In Ready, Great Location. This Four Bedroom Two And One Half bathroom Has Two Fireplaces, One In The Living And The Other In The Large Family Room. ...

An extraordinary opportunity to own a luxurious & contemporary designed home in the heart of the highly desired area of Winter Park! The curb appeal is magnificent w/prof...

This is a wonderful opportunity to own a beautiful Winter Park pool home. Elevated on a large lot of over half an acre in the desirable Sevilla neighborhood, this home ha...

PENDING - LOCATION, LOCATION, LOCATION! TAKE ADVANTAGE OF A SHORT WINDOW TO BUY THIS PROPERTY! Currently leased for $3,700 per month, so great investment property or make...

Located in HIGHLY desirable Winter Park “College Quarter” historic district, this home boasts plenty of CHARACTER and CHARM. Take a short walk to Rollins College and Par...

***Handyman Special*** Come check out this fixer upper featuring 3-bedrooms and 2-baths located in Winter Park. Property needs a roof, some TLC and updating. The seller ...

Inspired by the architectural styles of New Orleans, 1133 Sunset Drive is a modern take on tradition. Custom details abound in this 3 story, 3 bedroom, 2.5 bathroom Doubl...

Stately, French Chateau style, brick home located in Sevilla, one of Winter Park’s most desirable neighborhoods. Enter through large custom wood - double doors to a spect...

AWESOME "THE TRIANGLE HOUSE" PROFESSIONALLY DECORATED! 2 fireplaces - high ceilings, a spectacular lot make a special setting for a beautiful home. Mature landscaping gi...

This luxurious Taylor Morrison residence in Windsong, one of Winter Park's most exclusive neighborhoods, is designed to be breathtaking. Be amazed by the tree-lined ...

Sprawling 2,200+ square foot, 5 BED, 3 FULL BATH Winter Park Ranch! This flowing floor plan offers both formal Living and Dining rooms, a Family Room fireplace surrounde...

One or more photo(s) has been virtually staged. Beautiful WINTER PARK 2013 construction home with NO REAR NEIGHBORS & peaceful CONSERVATION VIEWS! Covered front patio tak...

POOLSIDE PARADISE. This home is located on a large corner lot and features a stunning tropical backyard with large open air pool, not one but two sundecks and is perfect ...

Spacious warm welcoming home in a gated community of Enclave at Aloma in Winter Park! This 5 bedroom 4 bath home has the curb appeal and looks brand new ! The natural ...

Step inside this newly updated Winter Park home and you might just fall in love. This home has 4 spacious bedrooms and 2 updated bathrooms. Walk-in and you automatically ...

Perfectly charming 3 bedroom, 2 bathroom, 1 car carport home located in the Winter Park city limits and zoned for A-rated Dommerich Elementary, Maitland Middle and Winter...

Beautifully designed and custom-built by premier Winter Park builder Bill Felkel, this stunning home is situated on an oversized 0.40 acre lot in the prestigious Winter P...

Sensational renovation of this adorable Winter Park-Orwin Manor home. All new Kitchen with new custom cabinets, new white quartz Corian counters, new cabinet pulls, new a...

Newly built custom home located in one of Winter Park's most established neighborhood of Winter Park Estates. This is a five bedroom and three bath single family home wit...

Spectacular corner lot. A Dream Location with views of Lake Wilbar. With multiple lots that total nearly a 1/2 acre of property, this Gem would make a fabulous location f...

Walking distance to Lakemont Elementary and Lakemont YMCA. NO HOA. Zoned for Winter Park schools, near places to shop and eat. This home has a screened in patio with a la...

Pure Potential! Excellent opportunity in Winter Park. Charming 2 bedroom, 1 bath home in the Heart of Town. Walk to Winter Park Village & more. Home has been lovingly ca...

Welcome to the Winter Park Pines, with tree-lined streets and the mailman that delivers to your door! You will not want to miss this beautifully, FULLY renovated home in ...

Gorgeous custom built pool home in the highly desirable Via's neighborhood in the heart of Winter Park. This home was designed to relax with family or entertain friends i...

Elevated on a stunning corner, double lot with panoramic views of Lake Sue, this gorgeous "Aurora award-winning" lakefront estate exudes elegance and grandeur. Luxury abo...

Motivated Seller!! Location, Location, Location! Excellent Winter Park location in the heart of Bear Gully Lake, Wow! Rare opportunity to live in Quail Hollow subdivisio...

With over 200K in recent upgrades, this home is the perfect combination of luxury & comfort. Not only will you find Busby cabinets throughout but also solid wood doors, n...

This Winter Park home has Lake Killarney access, it's a block home 3 bedroom 2 bath 1 car garage. Newer roof, new ac, new paint in and out, new kitchen with solid wood ca...

VALENTINES SPECIAL !! COMPLETELY RENOVATED WINTER PARK CHARMER JUST WAITING FOR ITS NEW OWNER. THIS THREE BEDROOM TWO BATH IS LIKE NEW FEATURING ALL NEW STAINLESS STEEL A...

Wonderful 4 bedroom/3.5 Bath Home located on a Beautiful Street in the “Heart of Winter Park”! A Private Courtyard with a Wrought Iron Gate Welcomes you! Enjoy this Open...

This stunning custom built home has the curb appeal you've been looking for! From the moment you pull up you'll fall in love with the architectural design, professionally...

Sale price is 205K CASH FIRM....Home needs new roof, flooring and tile in baths and is priced accordingly. Hyde Park is right where you want to be! Home features fireplac...

Southern Elegance with a Transitional Flair, this 4/5 bedroom/4.2 bath Pool Home with an Oversized Lot is located in the “Heart” of the Winter Park “Via’s”. A Fantastic F...

Unique property in a lovely neighborhood. Close proximity to I-4, Maitland, Winter Park Village, Park Ave, wonderful places to eat and great shopping. Take this opportun...

Great location! Highly desired neighborhood.Close proximity to I-4, Downtown Orlando, Maitland, Trader Joe's,Winter Park Village, Park Avenue, Restaurants and shopping. O...

Elegant Mediterranean home offers everything you desire when dreaming of living within 5 min walk of downtown Winter Park with neighborhood deeded lake access. Designed f...

A home like this seldom comes along. . . Winter Park lakefront home. Located on over 1 acre with 176 feet of lakefront on Bear Gully Lake, this charming home offers 5 be...

Gorgeous, Newer Construction (2016), FOUR Bedroom, Three & a half Bath, 3245 Square Foot, Two-Car Garage within 1/2 mile to Brookshire Elementary, Winter Park High, Ward ...

2018 Parade of Homes winner, completely custom built masterpiece is nestled on the border of Baldwin Park/WP. Your gorgeous 2018 home features an unparalleled list of upg...

Welcome to this gorgeous beauty in Windsong! Stunning travertine walkway entrance. Wonderful 12ft ceilings downstairs. Beautiful Brazilian cherry wood flooring throughou...

LOCATION, LOCATION, LOCATION.... If your looking for a great Investment property in Winter Park this is it. This home is right around the corner from The Winter Park Golf...

Enjoy lakeside living at it's best with water skiing, Kayaking or paddle boarding or dining at Hillstones before you head home. The value in this property is in the land!...

Fix and flip. Fix and reside. Take down and build a new home. If you are looking to have the opportunity to own in Winter Park - this may be your chance. Close to dow...

This custom creation by Winter Park's own Parkland Homes is a true representation of the "TRANSITIONAL HOME" movement offering timeless traditional exterior elevation wit...

JUST REDUCED. Well maintained Winter Park bungalow. Wood floors. Brand new roof on house, Jan. 2020!!. New central air and heat, summer 2019 too. Breakfast counters in k...

Just blocks from Lake Killarney, this bright and modern, open concept home is full of light and space. The kitchen with the large center Island is perfect for entertainin...

Searching for Land to build in Winter Park 32789 / Zoned R-2 with Top Rated Schools? This property is Adjacent to the proposed Orange Ave Overlay District featuring Place...

Searching for Land to build in Winter Park 32789 with Top Rated Schools? Be sure to check out this 77' x 161' homesite. Private corner lot measuring .28 acre on brick ...

Come take a look at this lovely updated home within the sought after community of Park Grove in Winter Park! After a long week of work, invite the neighbors over for a B...

This 2014 custom built home is for the lifestyle enthusiast. A perfect location combined with highly desired custom features will thrill the most discerning buyers. Shops...

Welcome to the fabulous one story home in the heart of Winter Park! As you walk in the front door you will love how light and bright the home is, which is accented by the...

Welcome to this charming pool home in a fabulous location and situated on a wonderful .25 acre lot. Lovely wood floors throughout the formal rooms and all 4 bedrooms. G...

Exceptional 4 bedroom/2 bath home in desirable Eastbrook! This wonderful home is located on a large corner lot. The open floor plan greets you with a generous living room...

PRICE DROP! Partly/Mostly Remodeled: Beautiful 3 Bedroom, 2 Bathroom POOL home in Winter Park, just outside of Baldwin Park. Located on a huge 1/3 acre fenced lot. Home h...

Beautifully renovated 3 bedroom, 2 bath pool home in Brookshire Heights! This home offers quality construction, new paint, high quality wood grain laminate flooring, an e...

This mid-century modern two-bedroom and two-bathroom home could use someone with the love for renovation. You could alternatively utilize the 86’ x 116’ lot to build to s...

Exceptionally stunning, brand new construction on Winter Park’s Lake Killarney. Built by Lazarus Development this modern, Spanish-inspired home features an amazing floorp...

A timeless property in Winter Park, designed by nationally renowned architect Gamble Rogers on a street rich in history & steps away from Lake Osceola. Privacy abounds wh...

Live your Florida dream in the flexible, open-concept Santa Rosa floor plan. Adapt this new Orlando home to your lifestyle and needs. Then enjoy the possibilities. Enter...

The spacious Anastasia floor plan offers a unique layout that’s ideal for family living. The foyer of the new home in Orlando angles off the front porch, with access to t...

Located on a corner lot in the elegant community of Penn Place, this fabulous home sits just blocks from the Winter Park 9-hole golf course, Park Avenue, and the WP Villa...

WHAT A LOCATION!! in sought after Winter Park, TOTALY REMODELED AND UNDER 245,000,Urban friendly within minutes to restaurants, groceries, retail, professional offices & ...

Gorgeous two-story Mediterranean pool home located in Winter Park’s prestigious Windsong community. Special highlights include multiple indoor and outdoor entertaining sp...

Absolutely stunning, brand new, custom built 4 bed, 3.5 bath pool home, presented by Lazarus Development Group. This home features so much attention to detail, including ...

LOCATION! LOCATION! LOCATION! This conveniently located mid-century modern home is just a 10 min drive from downtown Orlando. This well positioned home is on a quiet stre...

Significant opportunity to own one of the largest lots in the highly desirable tree lined streets of Winter Park. Land value is $550,000. – at lot size of 18,418 square f...

This fabulous transitional 5 bedroom home is situated on a quiet brick street just minutes to Park Avenue’s shopping & restaurants or downtown Orlando’s business district...

Stunning 2016 custom LunDev Homes masterpiece situated on a brick street full of newer homes just a short walk to Park Avenue! Superior construction and the finest finish...

Simply stunning MOVE-IN READY FIVE BEDROOM three full bathroom WINTER PARK home nestled in the small GATED community of Enclave at Aloma!! FRESH EXTERIOR PAINT!Step insid...

Stunningly inviting, this beautifully appointed Winter Park home in the prestigious GATED Bear Gully Pointe community will take your breath away! The community is situat...

Start Packing! This Lovely four bedroom two bathroom home located in sought after Winter Park Pines ready for a new owner. This home is exquisitely upgraded with beautifu...

LOCATION! LOCATION! LOCATION! Mid-Century Large Cottage Home. NO HOA! There are so many charming details about this home, the tile (backsplash) in the kitchen, the built-...

This contemporary elegant home is located in Olde Winter Park...the interior of the home has a very open floor plan...it has a resort style pool with lush landscaping and...

Welcome to your very own slice of paradise in Winter Park! Opening the front door you’re immediately welcomed into the living room filled with natural light from the larg...

Wanting to live in the "Via's"- This home is perfect for you! Full of upgrades and the attention to detail as you would expect! The home was just freshly painted outside,...

This is the house your buyers have been asking for! Fabulous home within walking distance to Park Avenue and Rollins College. Everything is done in this awesome house. Si...

Beautiful Charming and Newly Remodeled 4/2 home in well Desired area in winter park. This property boasts new tiles floors , new hard wood flooring in bedrooms, newly ren...

Imagine the possibilities! This property features a charming bungalow that you could move into, renovate, or tear down and build something brand new. It's comprised of tw...

Pre-Construction. To be built. International Design meets elegant transitional lines in this new Golf-View Winter Park home. Located in the downtown Winter Park corridor/...

In the celebrated City of Winter Park. No HOA fee, "A" School district home. Immaculate Converted 4 bedroom 2 bath split plan home with fresh interior paint! Converted ro...

Will not last! This house has been given a contemporary face lift. Gorgeous renovated Kitchen including granite countertops, tiled back splash, Skylight, and built in eat...

Under Construction. BRAND NEW CONSTRUCTION IN WINTER PARK! Stunning 4 bedroom, 3.5 bath home designed and built by local builder Homes by Carmen Dominguez. Every detail t...

One or more photo(s) has been virtually staged. Looking for a home built with magic? This is it! This 5 bedroom, 5 and a half bathroom home boasts breathtaking views of B...

Breathtaking high-quality home built by Zoltan Homes, in prime location in Winter Park. Boasting a tremendous open floor plan with over 11ft ceilings on the 1st floor and...

This Stunning transitional 5 bedroom pool home is perfect for family living & entertaining. Floor plan is ideal w/ 2 bedroom suites downstairs plus office/flex space. Met...

Another meticulously custom built masterpiece by award winning Austin Homes! Situated on an over-sized lot w/ deeded lake access to the prestigious Winter Park Chain of L...

Just Listed! Gorgeous .82 acre estate home in Winter Park’s Sevilla neighborhood. Set on an oversized lot that offers 120’ along Howell Creek, this amazing, one-of-a-kind...

Great quiet neighborhood in Winter Park. NO HOA! 4 bedroom 2 bathroom home updated in and out! No carpet in living areas! (engineered hardwood and tile) and carpets in...

Come tour this adorable, move-in ready ranch-style home located at the heart of everything! Winter Park Schools! Just a short stroll to Park Avenue, Rollins College, YMCA...

Spectacular home in a great Winter Park location...this 4 bedroom custom home is located on a quiet street in the heart of Winter Park. The 1st floor has stone flooring &...

The location of this charming updated gem does not get any better in Winter Park. This stunning 4 bedroom 3 bath property sits with lovely elevation on one of the most d...

THIS IS A MUST SEE ULTIMATE energy efficient smart home. This newly built MOVE IN READY home has 5 bedrooms and 3 bathrooms and is located in the highly sought after Haw...

One or more photo(s) has been virtually staged. Lovely custom built home with numerous upgrades throughout. Walk to Phelps Park, YMCA & Lakemont Elementary! Spacious & pr...

Final Price Drop! Wow! Location, Location, Location! This solid built home is filled with potential. Located in the heart of Winter Park, right around the corner from the...

Under Construction. "Under Construction" Brand NEW energy-efficient home ready March 2020! The Kerrville II floor plan impresses upon entry with a formal living and dinin...

PRICED BELOW APPRAISAL! The perfect balance of elegance, luxury and location adorns this 4 bedroom, 3.5 bath custom built home located on prestigious Palmer Avenue. You w...

Ready to move in Mediterranean Ranch home with new updates in the heart of Winter Park. Fully remodeled gourmet kitchen upgrades include large marble island, GE double o...

PRICE IMPROVEMENT! Amazing Coastal Modern home is now available. Located in the highly coveted tree streets of Winter Park. Custom built by premier builder Austin Homes a...

Situated on over a half acre of lush landscaping located a short walking distance to Park Avenue... this gorgeous 1940s ranch-style residence has been meticulously mainta...

Welcome home to this beautifully renovated just under 3, 000 Sq. Ft., four-bedroom, two-bath ranch style house which offers the opportunity to live and play in the Heart ...

Former parade of home winner underwent a meticulous renovation in 2019 creating the newest completely updated home in the Vias available on the market today. With its pro...

Welcome to this gorgeous, one-of-a-kind, contemporary-style home with over 150’ on the shores of Lake Berry. Custom built and architecturally stunning, this 5 bedroom, 4....

Half an acre in superior location steps away from Lake Chelton on brick streets in 32789. Considered one of the best neighborhoods in Winter Park! Beautifully remodeled M...

Close to everything. Back yard is adjacent to enviromental area.

If you love to cook and/or bake this is the kitchen for you. Recently remodeled and ready for you. Lovely granite counters and stainless steel appliances. Both bathroo...

Welcome to the highly desirable water view neighborhood in Winter Park. CANAL FRONT estate on the chain of lakes with original boat slip. 2 pieces of parcels for a pric...

Exceptional & Delightful Winter Park home! A thoughtfully executed quality build by Rex-Tibbs that offers so many sought after features, like gracious open floor plan, sp...

Cute and cozy Florida home located in Winter Park. This 3 bedroom 1.5 bath home with an extra bonus room in Winter Park Estates features over 1200 sq ft of living space. ...

NEW CUSTOM CONSTRUCTION IN WINTER PARK 32789 UNDER $700K!!! Stunning coastal modern home, wide open and very bright living areas, 3 bedrooms/2.5 baths, with lush tropical...

Don't miss out on this one of a kind, 3 story home. This home is 5 bedroom, 3.5 bathroom homes zoned for a work/live so you can easily make this space your office as well...

One or more photo(s) has been virtually staged. **New Construction and newly Renovated Property** Welcome to beautiful 1811 Bryan Avenue, centrally located in the heart ...

The value is in the land. Fantastic location. Unique opportunity to build a custom home with Maroon Fine Home, Inc. This beautiful property is located only a few bl...

Are you looking for that special Winter Park home with separate Office/Studio? Look No Further! This is the Winter Park home that you have been looking for. Warm and fami...

Located on a cul-de-sac in a desirable gated community in Winter Park, this 5 bedrooms/3 full bathrooms/2 ½ bathrooms house sits on an oversized lot. The community border...

Lovely 4/2 home with screen patio & 2 car garage

Welcome to this move-in-ready 4 bedroom, 3 1/2 bathroom pool home located in the wonderful community of Enclave at Aloma in Winter Park. This home features an open livin...

By far one of the most dramatic interiors of any home on the market in Winter Park. Award winning Brian Schlosser of NV design has created this exquisite remodel in the h...

Live in Winter Park’s Golden Triangle! Walk to Park Avenue, the Winter Park 9, Whole Foods - you name it! Rarely available, prime location and pure potential, this lock...

Under Construction. "Under Construction". Brand NEW energy-efficient home ready January 2020! The Valencia features an open floor plan providing flexibility and is perfec...

Under Construction. "Under Construction". Brand NEW energy-efficient home ready January 2020! The one-story Shore home features a split floor plan. Gourmet kitchen overlo...

Under Construction. "Under Construction". Brand NEW energy-efficient home ready February 2020! Relax and unwind in the Chislett's private master suite featuring tray ceil...

Builder's dream lot! This very large lot, 77x151.42, is located on one of the very desirable "tree streets" of Winter Park. Extremely convenient location, walking dista...

Stately custom Winter Park estate on Lake Maitland spans over 10,000 sq ft, offers 6-bed,7-baths,2-half for gracious living and refined comfortable entertaining.Two-story...

Just a short stroll to Winter Park's shops and restaurants, this updated large quality home features high ceilings, hardwood flooring, crown molding and spacious master b...

Unique ONE-STORY build on oversized lot. Brand new construction offered by Rex-Tibbs Construction, one of Winter Park's premier custom home builders for over 35 years. Th...

This beautiful Spanish Casita style home is located in highly desirable Winter Park. It is a short distance to Park Avenue, Hannibal Square, and Winter Park Village. Ente...

INVESTOR ALERT! Great tenants in place and occupied until 5/15/20. Owner has moved out of state and looking to sell. Beautifully remodeled home in A-rated school distric...

This beautiful 7 bedroom pool home features a traditional layout with formal living and dining rooms, an open kitchen and family room, and downstairs guest bedroom. From ...

INVESTOR ALERT! Great tenants in place and occupied until 5/12/20. Owner has moved out of state and looking to sell. Beautifully remodeled home in A-rated school distric...

INVESTOR ALERT! Great tenants in place and occupied until 5/12/20. Owner has moved out of state and looking to sell. Beautifully remodeled home in A-rated school distric...