Winter Park FL. Homes For Sale

Great location, great school district, great quality home! This 4 bedroom 2 bath pool home features a *NEW ROOF*NEW A/C* new paint inside and out, updated kitchen and ba...

Updated pool home with guest cottage and lake access on a beautiful, quiet Winter Park street convenient to Park Avenue. This home offers numerous options for guests and ...

Welcome to THE NEW AMERICAN HOME 2021 - another stunning design/build by Phil Kean Design Group. Designed as the International Builders Showcase Home, this 3-story stunne...

Wonderful four bedroom family home on beautiful tree-lined Summerland. Walk to downtown Winter Park & Park Avenue, and close to Maitland City Center. This home sits on la...

-Wow, this slam dunk Winter Park home is ready for immediate showings! This beautifully remodeled home just 10 min from one of Central Florida‘s most expensive, and desir...

4 Bedrooms, 2 baths, updated kitchen, fenced corner lot, pool, workshop and plenty of room to entertain! Bring your personal touch and make this your shining castle. Exce...

Stunning remodel in the desirable Kenilworth Shores community. When you first step inside, you're greeted with an open floor plan and tons of natural light. A beautiful c...

Tranquil one-story living in the heart of Winter Park. This beautiful 4 bedroom, 3 bath pool home will amaze you as soon as you arrive, with it's amazing manicured curb a...

This Winter Park home will have to be yours. It is a 4 bedroom, 2 bath with nearly 2000 square feet that has been freshly updated throughout. Also, the home has a new roo...

Outstanding opportunity to live in the heart of Winter Park. Adorable 3 bedroom, 2 bathroom 1,896 sq ft home being sold by the original owner who has taken great pride i...

Welcome Home! Gorgeous traditional home featuring mother in law apartment is nestled next to the Vias in Olde Winter Park. Enjoy the tranquility of the front patio on a q...

One or more photo(s) has been virtually staged. Rare Opportunity to own this large 2 Bedroom / 2 Bathroom Winter Park Condo. There are only a handful of units in this E...

Enjoy this lovely, recently remodeled home, in the beautiful city of Winter Park. This 4 bedroom 2 bathroom all-block home is primed and ready for its new owners to a...

New listing! Check out this amazing, newly built home by Barefoot Brothers, just steps from the East End Market. Built in 2019, this 3-bedroom, 3.5 bath home features an ...

Move-in ready. Come check out this beautifully updated Winter Park home on a private cul-de-sac. Full kitchen renovation including gorgeous granite countertops, stainless...

Welcome to the newly updated home in Winter Park! This 3 bedroom 1 bath home has plenty of space. It includes a den and bonus room, which could be easily converted to a 4...

Charming 3 bedroom, 2 bath home in Winter Park’s Waterbridge Community. Tucked away on a quiet, tree-lined street this lovely tennis community sits in a central location ...

Do not wait to see this amazing home in Timberlane Shores; known as one of Winter Park’s most sought after neighborhoods! This could be the one you have been waiting for....

Lovingly immaculate home remodeled to perfection and strategically located in a beautiful family neighborhood in Winter Park! This home is conveniently located less than ...

An exquisite Chain of Lakes offering awaits the most discerning of lakefront homebuyers in the heart of Winter Park. Being presented for the first time on the market, thi...

Beautiful Rex Tibbs traditional 5 bedroom pool home with stunning curbside appeal sits back off of brick-lined Via Tuscany in heart of Winter Park. Located on a breathtak...

This stunning home is located in the heart of Winter Park on a beautiful street..A courtyard welcomes you with a Wrought Iron Gate. This home has an open floor plan with ...

LOCATION and gorgeous shady lot make this ranch-style Winter Park home the perfect spot for home sweet home. This 4 bed/2 bath home features "wood-like" tile floors, upda...

Perfect place to build your dream home! Nestled in a quaint, quiet neighborhood in Winter Park, surrounded by million dollar homes. Tons of new construction on the street...

A MUST SEE COMPLETELY REMODELED 3 BEDROOM, 2 BATH END UNIT HOME. MASTER BATH HAS DOUBLE SINKS AND WALK IN SHOWER, GUEST BATH HAS 6 FOOT TUB/SHOWER COMBO. LARGE OPEN SP...

Breathtaking Lakefront home on Lake Killarney!! A slice of paradise in the heart of sought after Winter Park. This custom home has a touch of Mediterranean flair built by...

Location, location, location! This beautiful, 3 bedroom 2 bath well-kept home has all of the traditional features of the classic mid-century style. Situated on a corner ...

Under Construction. The adorable bungalow that is 1217 Kenwood Ave is located a couple houses off of famed Park Avenue and steps from the Winter Park Village which is und...

Welcome to this charming Winter Park bungalow located on a quiet dead end street. LARGE 59 x 157 lot features new backyard wood fence & shed. Inside you will find 2 Bed...

Elegant single-family home nestled in the heart of the Orwin Manor neighborhood of Winter Park. Only steps from the great dining of Orlando Avenue, Park Avenue, and Downt...

YOUR GAIN! Laminate floors, plantation shutters, stainless appliances, French doors, in-ground pool, covered patio, NEW ROOF, generous lot, fully fenced yard, and so much...

Winter Park one story large single family pool home four full bedrooms and 2 baths in main house... additional apartment which has living room kitchen space, bedroom and ...

A quiet, tree lined street leads you to this beautiful cottage style home in Winter Park! A neatly manicured front lawn and towering oak trees greet you as you walk up th...

This updated and well-maintained home is perfect for anyone who loves to entertain and is looking for an open floor plan! Enjoy the mature landscaping on this large corne...

Presenting to the market for the first time in 54 years and on a double lot with approximately 200 feet of water frontage within footsteps of Park Avenue, situated on Lak...

"The richness of an artist is the fusion of influences that have shaped his life and work", ~ Fernando Botero. WELCOME HOME to 2550 Venetian Way, located in the historic...

CHARMING WINTER PARK HOME LOCATED IN THE HIGHLY SOUGHT AFTER GARDEN LAKE ESTATES COMMUNITY! This stunning split plan home was recently remodeled including new wall & knoc...

Charming pool home in premier Winter Park location nestled along the Via’s with neighborhood lake access to Lake Maitland. Floorplan is open and inviting with dining room...

Pre-Construction. To be built. To Be Built. This stunning Alys Beach Modern Dutch Masterpiece is being crafted by none other than, Floridian Custom Homes of Winter Park....

Wonderful home in beautiful Winter Park Estates! Larger home in the area. 4 large bedrooms and 2 bathrooms. Fully renovated with designer features. Beautiful new kitchen ...

This charming bungalow is located in the prime location of Winter Park. It offers some vintage details combined with upgrades and additional qualities. Walk in to a very ...

This Winter Park one-story home offers a one-car garage.

Located in a quiet WINTER PARK community with a FANTASTIC VIEW to a WATER FRONT and PARK, this 3BD/2BA Single Family AFFORDABLE LUXURY HOME offers FANTASTIC INSIDE UPGRAD...

This three bedroom, two bath home, ideally tucked away on a quiet cul-de-sac, sits on the edge of the Winter Park Pines Golf Course. The traditional layout includes forma...

Under Construction. Location, location, location! Nestled in Winter Park, this home is convenient to the best in shopping, dining and entertainment! The two-story Easterl...

Pure potential in Winter Park. Large, 4 bedroom, 3.5 bath pool home with detached studio and full bath. Incredible location between downtown Winter Park and nearby Baldwi...

Finally the one you've been looking for! Fantastic Rated Schools, Saltwater Pool, Completely updated inside and out! 5 Minutes to Baldwin Park & Winter Park's Famous "Par...

Wonderful opportunity to own this exquisite 4 bedroom, 3 bath + bonus room home in the heart of Winter Park. Located in the gated community of Enclave at Aloma. This op...

Unparalleled quality in highly desirable Winter Park. Just completed new Construction. A must see 2 story 4 bedroom 3-1/2 bathroom dream home. 2,472 sq.ft. conditioned ar...

Under Construction. Transitional style 4 bedroom / 3.5 bathroom new home in Winter Park. Stunning and meticulously done, located in the beautiful and highly sought-after...

Coastal inspired, newly built, 2-story POOL home exceeds your expectations and is desirably located just minutes away from the Park Avenue fine dining and retail shopping...

Seller says "SELL THIS HOUSE!" So, Bring all offers! LOCATION, LOCATION, LOCATION! less than 10 MINUTES TO DOWNTOWN WINTER PARK! If you love the finished homes from the s...

This four-bedroom, four and one-half bath pool home is a unique opportunity with over one-half acre, in the heart of Winter Park, minutes walk to Park Avenue shops and di...

Welcome Home to Maitland Shores on the 'Chain of Lakes' in beautiful Winter Park, Florida! Property/Lot located ON THE CANAL WITH DIRECT ACCESS to Lake Maitland and Chain...

***MOVE IN READY HOME IN WINTER PARK with 4 BR/2.5 BA*** Quiet neighborhood – Very convenient to Full Sail University and University of Central Florida, highways and sho...

Announcing a fantastic new listing in the Heart of Winter Park within walking distance to Park Avenue, the golf course, shops, dining and more. Tucked quietly off Park Av...

Priced to sell in desirable Winter Park. This 3bed/2bath home is conveniently located with close proximity to Baldwin Park and downtown Winter Park. Terrazzo floors throu...

2016 LunDev beautiful modern farmhouse on a quiet street in Winter Park. Light, bright and open concept with great split-plan layout. Kitchen open to dining and gathering...

Luxury lakefront custom home awaits. This Parade of Homes winner features spacious open floor plan with great attention to detail. Large gourmet kitchen opens to spacious...

This charming and updated split 3 bedroom 2 bath bungalow on an oversized fenced-in lot, It is located on a quiet cobblestone street in the heart of one of Florida’s mos...

One or more photo(s) has been virtually staged. Prepare to be amazed by this ultra modern home located in the private gated community of Hawks Crest. This incredible home...

Captivating and Traditional Southern Home in Winter Park! Situated on a sizeable 0.26+acre lot, this storybook 4BR/4BA abode captures attention with a muted buttercream e...

Located in the highly desirable Winter Park Location. This 4 Bedroom/ 2 Bathroom recently renovated home features updates throughout. This beautiful charming newly remode...

STATE-OF-THE-ART technology, TOP-OF-THE-LINE finishes, attention to DETAIL, and centrally LOCATED in historic WINTER PARK is where you will find this 2019 fully renovated...

Located in the heart of Winter Park with close proximity to shopping, Winter Park hospital, and A rated schools. This 6,592 square foot lot is ready to build your dream ...

Over-Sized Lot. The fabulous Winter Park Custom Builder Rex-Tibbs has designed this Winter Park home, that is located in one of Winter Park's most beautiful and private n...

Presenting to the market for the first time in 53 years, this stunning Spanish Revival estate home. This fourteen-room estate sits on 3 lots. There are lake views from do...

2019 PARADE OF HOMES Entrant - Come see this lovely pool home with a nice open floor plan located in walking distance to all that Winter Park has to offer. After a long w...

Fabulous modern Mediterranean on a quiet cul-de-sac location nearby downtown Winter Park/Park Avenue. The property affords wonderful privacy with a "park-like" backyard. ...

One or more photo(s) has been virtually staged. STUNNING AND STATELY 4,720 square foot Mediterranean Winter Park home CLOSE TO PARK AVE and beautiful Lake Virginia. A Cla...

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 distinguished Winter...

Priced to sell. Custom built Mediterranean home on secluded cul-de-sac in exclusive Elizabeth's Walk enclave of Windsong. Exterior features include 10' solid mahogany d...

Rare 10+ acres with 3 adjoining parcels 5500,5490,5510 in Winter Park. Potential Commercial Perfect opportunity to build multi-family, subdivision, strip mall, church, or...

The work of a local award-winning designer, this transitional Winter Park classic features a modern exterior elevation, with ornate compliments of very familiar and local...

Must see this beautiful 4 bedroom 3.5 bath 3,606 sqft home on one of the most charming streets in Winter Park nestled between Lk Knowles and Lk Wilbar. This home was exte...

Rare opportunity to own a completely multi-generational home in the exclusive neighborhood of Talman Mews on DUAL lots. The statement entrance begins under the portico w...

Award Winning, Winter Park Historic 4 Bed, 3-1/2 Bath Home meticulously restored to Perfection. With Features and Finishes that rival new homes in the area, it will not ...

Presenting to the market for the first time in 54 years and the first time ever as three properties combined over the years all within footsteps of Park Avenue and situat...

Move-In Ready!! This Brand New 2021 Custom Home is ready for your family. Rex-Tibbs Construction has been building timeless homes in Winter Park for over 35 years. A guar...

Classic lakefront home in Winter Park, 32789! Experience the tranquility and extraordinary views of the protected natural habitat across the lake. The far shoreline of La...

Rare Opportunity to live in Winter Park, in a secluded beautiful Cul-de-Sac overlooking a wide open green area with a great privacy. Only a steps away from all the Major ...

Magnificent new construction Downtown Winter Park estate, built by one of the country’s top builders, this architectural masterpiece is situated just steps from Park Aven...

One of a kind meticulously maintained ONE STORY Winter Park Charmer within walking distance to Downtown Park Avenue. Originally custom built for the local Miller hardware...

Winter Parks Hidden Gem Seranza Park. This Almost-New Home is a Must for any buyer. Located in Seminole county with an A rated school district. Conveniently located near...

Opportunity Knocking - located at the end of a private drive off of Old Winter Park Road. Do you want to make money in real estate? A wise person once said buy on locati...

One or more photo(s) has been virtually staged. Don't miss out on this one of a kind, well maintained, and extensively renovated five bedroom, three and a half bath Winte...

This truly unique historic property built in the 1880's has been described as the most Victorian cottage still standing in Winter Park and perhaps the finest example of V...

Welcome Home! ***Per previous appraisal, Main house is 3,021 sq. ft. and Guest cottage is 649 sq. ft.*** $20K Price Reduction! Great Opportunity to own a Winter Park Heat...

WINTER PARK HOME AT EASTBROOK COMMUNITY. COMPLETED RENOVATED HOME !!! NEW WATER HEATER, NEW LUXURY VINYL PLANKS FLOORING THROUGHOUT THE WHOLE HOUSE, NEWER A/C, NEW KITCH...

Pre-Construction. To be built. Modern French country villa, situated on an oversized 0.36-acre lot located along the beautiful tree-lined Palmer Avenue. This villa is des...

This is your opportunity. Exquisite Winter Park Townhome Style property offering best of single family living with no HOA. Conveniently located - Winter Park shopping, di...

Custom built home located Inside the beautiful, gated, Cypress Reserve neighborhood. Spacious 6 bedroom, 5 bathrooms and 3983 Square feet. This house has LOTS of room f...

One or more photo(s) has been virtually staged. Welcome to this one-of-a-kind contemporary masterpiece, custom-built by LunDev in the heart of highly desired Winter Park!...

One or more photo(s) has been virtually staged. Located in the heart of Winter Park, this virtually new Modern Florida Coastal custom pool home was built by David Cahill ...

Back on the market!! Owners wanted one more holiday season of memories before parting with their home of 35 years. This home provides a popular 5/2.5 three way split poo...

WELCOME TO YOUR FOREVER HOME - LOCATION! LOCATION!! THIS IS A MUST SEE HOME!!! THIS METI...

Entertain! Entertain! Entertain! Beautiful 2018 Custom built Winter Park lake front home on one of the most desired lakes in the area. This home features all the amenitie...

Beautiful one-owner custom-built home. All richly appointed with beautiful moldings, stunning wood floors throughout, with Grand Foyer & Entry. Formal living and family ...

IMMEDIATE SALE!! 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 yo...

Lake Front on large, clear, spring fed Lake Waunatta. Bass fishing / water ski / jet ski. 3 Bed 2 Bath. Approx 3244 SF single story home. 2 year new roof. Ceramic tile t...