Winter Park FL. Homes For Sale

MID CENTURY BEAUTY with timeless thoughtful design, quality construction & updates including gleaming hardwood floors, double pane windows, new garage door & new roof in ...

Welcome to your new home in the desired Winter Park Area. Your new home features brand new exterior stucco and paint, new home ac system installed, brand new electrical s...

Nestled in the heart of Winter Park and surrounded on both sides by brick streets, this elegant ONE-STORY 3 bed / 3 bath home sits on a large corner lot (100x125). The mo...

cOME AND SEE IT! Highly Desirable Winter Park location! Remodeled Kitchen has Stainless Steel Appliances and Quality Cabinetry. The Open Floor Plan 3 Bedroom home has dur...

This location is in the hub of Audubon Park with a Winter Park address. Walk everywhere. Enjoy Baldwin Park's amenities right across the street with no HOA fees. Nestled ...

Well-Priced & Sprawling FOUR Bedroom, 2.5 Bath Concrete Block, Two-Story ESTATE Home in the Prestigious WINTER PARK PINES! Shining Curb Appeal with Lush Landscaping and ...

Custom-built Mediterranean home, situated on a .64-acre lot (140x195), perfectly balances the classic Spanish style with the functionality of casual living. With over 6,4...

Live in the DESIRABLE City of Winter Park! Don't miss the opportunity to live in the charming community of Winter Park Estates close to shopping, dining and everything yo...

Back on market at one of the lowest prices per square foot in the neighborhood. Traditional home remodeled just 6 six years ago and sits on a 100 x 150 foot lot with pool...

Mediterranean garden paradise sitting on the pristine Lake Killarney. This exquisite home features 5 bedrooms, 3 full baths and two half baths. There is a phenomenal lake...

Are you looking for a beautiful home nestled in a cul-de-sac in Winter Park? Here is the must see for you. Enter and see the beautiful oaks and landscaping. The pride of ...

Under Construction. "Under Construction" Brand NEW energy-efficient home ready June 2019! This Shore home's split floor plan boasts a large owner’s suite with spa-like ma...

Stunning and Modern- 2017 new construction in a superior location! You will be blown away by this 4 bed / 4 full bath plus office and loft custom home. Light & bright ope...

This gorgeous three bedroom two bath home sits on nearly a QUARTER ACRE CORNER LOT in the heart of Winter Park. Your new home boasts amazing curb appeal from the well mai...

This property offers a wonderful opportunity to build new in Winter Park. Lot is 75x149x75x151, 11,237 sf. Great location - Just 1 block to the Y and a short stroll to Ph...

Welcome Home! The phone is already ringing and appointments are being scheduled. This property stands out as a wonderful opportunity to a multitude of buyers. Whether you...

Here it is! Great schools! No HOA! Walk to Winter Park High, Walk to winter Park Pines Golf Club! Private screened pool with large fenced yard and towering oaks! This hom...

Winter Park Gem!! Don't miss this incredible investment possibility. A builders DREAM property, on a quiet cul de sac, over sized lot of almost 10000 sq ft. Great for bu...

This move-in ready 4/2 home sits on a huge lot on a quiet cul-de-sac in classic Winter Park. This beautiful home is situated in a family-friendly neighborhood, updated wi...

LOCATION! LOCATION! LOCATION! You’ll be in the heart of Winter Park, right on a creek that lets out into Lake Killarney. Take your boat to enjoy a facial at the spa or gr...

Courtyard Home conveniently located in Winter Park. This 3 bedroom, 2 bath home boasts multiple private decks and courtyard. Walking distance to East End Market, Shops an...

This is a wonderful opportunity to own a 4 bedroom Winter Park pool home in one of the most desirable locations and in-demand areas! Perfectly located between downtown Wi...

Curbside appeal is just the beginning with this unique 1965, split-level, lakefront home located on Lake Sylvan. Serenity begins when you enter through the gates to a pri...

PRIME LOCATION and what a bargain! This home is located in the highly regarded city of Winter Park just minutes from the historic district. With a large yard and a great ...

This Winter Park one-story offers an in-ground pool, hardwood flooring, a fireplace, and a two-car garage. Upgraded features include a new HVAC unit. Home comes with a 30...

Gorgeous 5 bedroom 5.2 bath home located in the heart of "The Vias". Fantastic floorplan featuring downstairs master suite including 2 walk in closets, large master bath ...

Stunning Windsong Estate in Heart of Winter Park! Located on a quiet street in one of Winter Park’s most sought-after neighborhoods, this 4 bedroom, 5 bath pool home feat...

Finish the cosmetics on this 4 bed, 3 bath, 2 car garage project home and sell, rent, or enjoy your sweat equity! Fundamentals done: new fencing and gates, soffits and fa...

You will want to see this well maintained 4/3 pool house in the desirable community of Kings Cove. As soon as you pull up to this house, you will notice it sits at the ...

Three Years NEW Construction. This Modern Transitional home is a Must See. It is walking distance to East End Market and all of the shops and restaurants from fine dining...

This home has the best LOCATION, LOCATION, LOCATION. This neighborhood is known as the "TREE STREETS". Great Investment Home located on a brick street. Situated on a 50' ...

Be Ready to be Impressed with this Completely Updated & Renovated Home for your Family. This Home Features a Fully Renovated Kitchen with Granite Countertops, Stainless S...

INVESTORS or soon-to-be HOMEOWNERS! Introducing to you, this fantastic Winter Park home looking for your personal touch! On a large corner lot, right off Hole 7 on Dubsdr...

LAKEFRONT home in exclusive Bear Gully Pointe. This home was constructed by the Original Owner who happened to be one of Central Florida's top custom builders for over 3...

Gorgeous estate home located in desirable Winter Park, Florida! The original owners have cared for this impeccably maintained home - no detail spared. Extra-long pavered ...

A move-in ready spacious home in a wonderful Winter Park neighborhood that is close to everything great about the area. Good schools, parks, golf, excellent shopping, Wel...

LOCATION! LOCATION! LOCATION! Home well positioned on large 0.28 acre lot in 32789. Gorgeous two bedroom home right in the heart of Winter Park. Perfect lot for a new bui...

Thoughtfully conceived and designed, this award winning, custom built Lake Maitland waterfront estate is sure to impress! Crafted all on one level, this charming lakefron...

This lovely Winter Park, 4 Bedroom, 2 Bath home is spacious, light and bright ! Laminate wood flooring throughout. Bathrooms have been updated with new tile, fixtures a...

Looking for a spacious, meticulously maintained and updated home in the Winter Park area? Your search is over, you’ve found it! Upon arrival you’re greeted by swaying pal...

Located on the shores of Lake Howell, this Lakefront property offers the potential buyer over 4 acres of High and Dry Land in a serene natural setting. After viewing the...

Gorgeous brand new construction in Winter Park! Walking distance to Park Avenue and the Winter Park Village puts you within minutes to the best restaurants and shops in t...

Under Construction. To be completed by award winning custom home builder M. Lahr Homes on one of the most exquisite “tree streets” of Winter Park. This transitional two-...

Beautiful Winter Park Pool Home! This updated pool home is located on a tree lined street of the desirable Winter Woods Community. Your new home features a large, fully r...

Brand new to the market is this beautiful 3 bedroom and 2 1/2 bathroom with 1618 square feet of living space located in the heart of Winter Park. Upon entering this beaut...

Incredibly charming 3 bedroom, 2 bath home located on Winter Park’s desirable Park Avenue! Steps away to all of the downtown shops, restaurants, parks and more! Great cur...

This lovely, traditional Winter Park home has been updated and is ready to move in. The antique brick porch and welcoming front entry make you feel at home as soon as you...

Welcome home to 1709 Pine Avenue! Located on a 75'x130' lot, this charming 2 bedroom, 2 bathroom home features an amazing location in the heart of Winter Park, great livi...

Elegant modern Mediterranean home located in the downtown Winter Park corridor within walking distance to Park Avenue shops/restaurants as well as the Winter Park Village...

Beautiful 3 bedroom 2 bath home located in the tucked away neighborhood of Lost Creek. Gorgeous hardwood flooring, extensive ceramic tile, french doors, split bedroom flo...

Located in the Howell Estates community. This 4 bedroom, 2 bath home features an open floor plan, dining area, galley kitchen, and family room. The home has been fully r...

Custom Winter Park home on prestigious Palmer Avenue now available for you. The floor plan flows perfect for entertaining and at the same time offers privacy and comfort ...

PRICE IMPROVEMENT!!! COASTAL INSPIRED DESIGN BY DAVID WEEKLEY HOMES, LOCATED IN THE HISTORIC DISTRICT OF WINTER PARK, ENJOY FINE DINING, SHOPPING AND ENTERTAINMENT IN WAL...

PRICE IMPROVEMENT!!! COASTAL INSPIRED DESIGN BY DAVID WEEKLEY HOMES, LOCATED IN THE HISTORIC DISTRICT OF WINTER PARK, ENJOY FINE DINING, SHOPPING AND ENTERTAINMENT IN WAL...

PRICE IMPROVEMENT!!! THIS NEW DAVID WEEKLEY HOMES COMMUNITY IS NESTLED RIGHT IN THE HEART OF HISTORIC WINTER PARK, CONVENIENT WALK TO THE BEST DINING, SHOPPING AND ENTERT...

This beautifully updated lakefront gem awaits you! This home is solar powered and includes insulated windows and a Nest thermostat for maximum energy savings. This home f...

Under Construction. Under Construction - Estimated Completion June 2019 - BRAND NEW home located in gated Winter park community!! Small 28 home community with access to L...

***Located in TOP rated school district and convenient to Maitland and downtown Winter Park. Come check out your new home! This eclectic Winter Park mid-century modern ho...

You might think you’re in a model home! Located on a quiet CUL-DE-SAC, the ORIGINAL OWNERS have meticulously cared for this 4 bedroom, 2 bath home. BRAND NEW ROOF (2/19)....

Come see this beautifully renovated ranch style home in the heart of Winter Park! Within walking/biking distance of top rated Winter Park schools, beautiful Baldwin Park,...

DON'T WANT TO MISS THIS HOME. Welcome home to the Winter Park Pines where the mailman delivers to your door and sidewalks line both sides of the street. DO NOT MISS this ...

LOCATION. LOCATION. LOCATION. This gem of a home is nestled inside a quaint Winter Park neighborhood. Walking distance to Winter Park Village, Publix Shopping Center and ...

Fantastic Mid-Century, Country French Ranch style Home in the Heart of the Winter Park Growth District. Now available, this 3/2 Solid Block home Right across the street f...

This property is in a high demand area of Winter Park, close to Dubdsread Golf Course. It sits on a quite street just off Fairbanks Ave. and I-4 entrance ramp. Your just ...

Better than NEW Custom home located in Desirable Winter Park. 4 Bedroom, 4 ½ bath home has EVERYTHING! DRAMATIC, open floor plan. Lovely formal dining room, HUGE Gourmet...

Beautiful home on Winter Park Chain of Lakes. Stunning estate on Lake Osceola with long private driveway to home that has gorgeous views of pool, gardens and lake. This o...

Amazing opportunity to own a Rex-Tibbs home built in 2013 taken to the next level by the original owners! It is located on a secluded brick street surrounded by many new...

Must see beautifully redone 3 bed 2 bath split plan home located in Winter Park near Full Sail, Sprouts and Lucky's Market. Move in immediately, everything is ready for y...

Welcome home to this beautiful 4 bed/2 bath Winter Park family home. Amazing location, modern charm, updates though out. You will be enchanted by the meandering OAKS THAT...

Beautiful 4 bed/2 bath pool home in Winter Park, just steps from skiable Lake Killarney. This one of a kind home has been updated and renovated to give it a modern feel ...

Under Construction. This 2019 Parade Of Homes entry is another stunning new custom build by LunDev Homes. This 4 bedroom 3 1/2 bath transitional farmhouse with old Florid...

This Stately Custom Built Rex Tibbs traditional home has a grand entry from sought after Via Tuscany location onto a circular drive that extends to side garage entrance. ...

MOVE IN RREADY. This 4 bedroom, 2 and half bath 2 story house is located at a gated Winter Park community. NEW fresh interior paint throughout the whole house. The OPEN F...

Tucked away in such a sweet community yet close to everything! This home has all the touches of an elegant interior at an affordable price. Freshly painted inside and ou...

Gorgeous custom home in Winter Park 32789 on a lovely tree lined cul-de-sac! Immediately upon entering you are greeted by a wonderful open and bright home with vaulted ce...

REDUCED!!! REDUCED!!! Seller Motivated!!! Bring Your Investors!!! Winter Park Schools! This newly updated home is located in the perfect spot. 7 minutes to Park Ave and 1...

Freshly painted inside out along with a brand new AC system is this comfortable 4 bedroom 2 bath 2 car-garage pool home located in the peaceful Wrenwood Subdivision. Walk...

WINTER PARK WELCOMES IT'S NEWEST ADDITION TO THE LUXURY HOME MARKET! This exquisite recently completed dramatic & sophisticated new construction home by M. Lahr Homes is ...

Beautifully renovated 3 bedroom 2 bath home in Kenilworth Shores! As you walk in you will see the kitchen has been renovated with 20 inch tile, granite counter tops with ...

GREAT LOCATION IN DESIRABLE WINTER PARK AREA , GREAT OPPORTUNITY TO LIVE AND WORK. This is a 2 unit property , a single family home AND a day care center. This 2,250 ...

This amazing Winter Park home benefits not only from it's highly sought after location, but from an extensive 2016 renovation that included a new pitched roof, brand new ...

Wonderful Lake Virginia one story pool home at the end of quiet Virginia Drive in Timberlane Shores. This home has great entertaining spaces with living room, oversized f...

Welcome Home to the LAKEFRONT WINTER PARK LIFESTYLE you've been dreaming about! Properties on Lake Virginia are RARELY available, and this one is brimming with potential ...

Winter Park Chain of Lakes, Lake Osceola waterfront property, with over 100 feet of shoreline, ready for a new custom home or renovate the existing structure. A beautiful...

Pre-Construction. To be built. Custom Home by Winter Park’s Classic Homes. This Contemporary design will feature all the high-end finishes & quality craftsmanship that th...

Under Construction. New construction Winter Park French European Estate on corner of Palmer & Anchorage Court, a special street rich in history, close to Lake Maitland, a...

Under Construction. This New Construction home is located in one of Winter Park's most convenient neighborhoods. This California Coastal home is on two lots. Entering the...

Stunning 4 bedrooms, 2 bathrooms home with more than 2300sf of living area. The house will be sold with a new roof. This home was remodeled with porcelain tile floor, ...

Proudly offering a beautiful Mediterranean style home in highly desirable Winter Park. This charming home has so many unique features, it can only be appreciated by viewi...

Beautiful Custom two-story home Built in 2005 located in Winter Park on the cusp of Orwin Manor. Professionally landscaped. Meticulously clean and well maintained. Bri...

***DON’T MISS THIS ONE*** You are going to fall in love with this beautifully updated 4 bed, 2 bath pool home situated on an oversized lot in the very popular Winter Park...

Welcome to Casa Bella Vista. Magnificent one-owner Mediterranean lakefront featuring quality and character throughout capturing lake views from almost every room with an ...

Nestled in the heart of Winter Park, in the highly sought after Via’s, this is a must see beautiful, custom home on a half acre corner lot! Awash in natural light this ho...

Absolutely stunning and newly constructed modern delight home featuring modern upgrades that provide efficiency, energy savings and living conveniences in sought after Wi...

The freshly painted interior of this 3 bedroom 2 bath home greets you with lots of light and wood floors. Casual dining space with sliding glass doors over looking the b...

Great corner lot with screen enclosed pool. Most of the homes in this area have low ceilings but not this one. When the trusses were replaced we were able to raise the ro...

Come see all that this lovely 4 bedroom 2 bathroom Winter Park home has to offer! This house sits on a large corner lot that is over 10,000 square feet. Home features a v...

This custom built modern luxury home with a view of lake Killarney features 3 bed, 3 bath and a bonus room. Move in ready, bright and open floor plan is excellent for any...

Inviting pool home that is move-in ready! The enticing neighborhood of Autumn Glen features community tennis courts, a playground and a pond. The 4/2 split floor-plan o...

Lovely Winter Park home to enjoy Florida's outdoor lifestyle with an amazing backyard pool spa deck and fire pit. House offers outdoor views and natural light from every ...

One of kind Zachary Kauffman masterpiece on 1+acre on Lake Maitland now available. With his renowned attention to quality & detail, this 5+bed/5+bath has timeless traditi...

Welcome home to this luxurious, custom built two-story, Modern Farm style home. Boasting 5 Bedrooms, 5.5 Baths and 4,434 SF of interior living space. This striking home ...

Welcome home! You’ll be right off University Boulevard and close to shopping centers, restaurants, Full Sail University, Publix, UCF, 417, Orlando Executive Airport, Bald...

Stunning modern Mediterranean on a quiet beautiful brick street in Olde Winter Park near Lake Sue. One owner home meticulously maintained with quality and craftsmanship t...

New Construction in WINTER PARK! This is the one you have been searching for! Lovely location just a few short blocks to PARK AVE, with wonderful dining, shopping, and en...

OUTSTANDING REMODELED HOME IN WINTER PARK WITH BRAND NEW KITCHEN, BATHROOMS AND FLOORS!!! This gorgeous home has been completely Upgraded from top to bottom with Granit...

Location, Location, Location ! This amazing property is Located in the heart of the exclusive Winter Park. A custom build home that offers two living rooms and a stylish ...

Charming Winter Park pool home now available. Fresh exterior paint and landscaping invite you into this spacious split level home. The main level offers tile through ou...

Wonderful opportunity to build new on this Half Acre Lot, or renovate existing home on Beautiful Lake Berry! With a Southern Exposure your views of the Sunrise and Sunse...

Amazing Winter Park neighborhood, surrounded by multi-million dollar homes and new construction! This property features 3 bedrooms, 2 baths, a pool and is tucked away on ...

BEAUTIFUL. Functional OPEN FLOOR PLAN gem in desirable Kenilworth Shores. CIRCULAR DRIVEWAY for additional parking space. FRONT PORCH takes you inside to FOYER. LIVING AR...

One or more photo(s) has been virtually staged. 2019 PARADE OF HOMES Entrant - Amazing 4 bedroom / 4.5 bathroom modern masterpiece with soaring 12-foot custom coffered & ...

RECENTLY APPRAISED FOR WELL OVER LIST PRICE! Live in a vibrant area of Winter Park - where convenience and lifestyle are all around you! Immaculate Ranch style 3 Bedroom/...

NEW CONSTRUCTION, MODERN HOME CLOSE TO PARK AVE. WINTER PARK! This home has plenty to offer. Fantastic lighting throughout by thoughtful use of large windows and oversi...

Under Construction. The latest masterpiece from Winter Park’s premier builder FG Schaub Custom Homes. This Modern Farmhouse was designed by David Larson and is sure to ex...

Simply stunning! This like new Mediterranean Estate Home is located in the highly sought after Windsong Community and has been tastefully upgraded and meticulously mainta...

This luxurious estate is a European masterpiece located in the golden triangle of Winter Park. A mature, well manicured podocarpus hedge surrounds this .59 acre property ...

When pride of ownership meets your opportunity to own a beautiful traditional home in Winter Park. Updated with quality and attention to detail, this 3 bedroom 3/1 bath i...

Tremendous character and charm throughout this stunning Santa Barbara-style Mediterranean resting on almost a 1-acre lot in the Vias. Waterfront estate size property on t...

We believe that everyone should have a place to call their own home. We bring to the market beautiful properties like this one in excellent conditions and at affordable p...

Situated on an oversized beautiful corner lot in the heart of Olde Winter Park, this 1920s home with historical designation, boasts character and charm. Located in the hi...

Great location in Winter Park 32789 on an oversized 0.27-acre lot steps from beautiful Lake Killarney! Charm radiates throughout this inviting three-bedroom, two & a half...

Exquisite inside and out! This magnificent Georgian-style estate home was meticulously constructed by Posada Custom Homes and is located in one of Winter Park's most desi...

This is your opportunity to own a beautiful home Located in the heart of Winter Park Historical District, Roof is less than a year old, new A/C System , beautiful Pool...

Under Construction. Under Construction. Soak up all the charm of the Seaburg Floor Plan. Located in the highly sought out area of Winter Park, 32789. This premiere locati...

Under Construction. Under Construction! One or more photos have been virtually rendered.This two-story contemporary home features 4 bedrooms, 3 full and one half bathroom...

Under Construction. Under construction. This is a custom home located in the trendy Lake Midget neighborhood of Winter Park. One of a kind. The architectural style of the...

Nestled on a quiet cul de sac in the desirable subdivision of Winter woods. This charming single story Pool home features spacious front porch & landscaping all around. I...

Considered one of Winter Park’s quaintest streets, this spacious two-story five bedroom home, plus an In-Law suite offers a versatile floor plan to fulfill every family's...

Beautiful 4 Bedroom, 2 Bath single family in the brilliant community of Brookshire Heights, Expanded Kitchen area with granite countertops and open granite countertop is...

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

Bring offers! Seller will pay up to 3% buyer closing cost on full price offer. Great Winter Park location FHA, VA approved property. Fully remolded and waiting for you! W...

Fantastic opportunity to purchase NEW CONSTRUCTION in one of Winter Park’s most desirable neighborhoods walking distance to Phelps Park, the YMCA, Lakemont Elementary and...

This premier Winter Park lakefront property on Lake Osceola provides an opportunity to build anew, renovate or use existing home on an absolutely beautiful elevated lot o...

Picturesque four-decade family home located in the prestigious Via’s of Winter Park! Three bedrooms plus loft and office/in law suite. Owner/Architect designed the total ...

Welcome Home to this charming solid block home in the desirable family neighborhood of Kenilworth Shores. Upon entering you will enjoy the light and open modern floor pla...

ONE OF A KIND 3 Bed, 3 Bath, 3,427 sf estate (main house) INCLUDING detached IN LAW SUITE - 4th Bed/Full Bath! This spectacular home combines the warmth of historic Wint...

SHOWCASE HOME- When you want your life to feel like a resort! Custom designed by Origins Residential Design. (Dan Delong) Modern, Flexible Floorplan featuring spacious o...

Situated on a corner lot in the sought after lovely community of Winter Park Pines is this 4 bdrm/3 bath home of quality concrete construction. Meticulously maintained & ...

Southern Elegance just steps from Beautiful Park Avenue! Walk to Shops, Restaurants, Art Festivals and all that Downtown Winter Park has to offer. This Lovely Home Exudes...

Well appointed modern home in great location overlooking water. 4 bedrooms with one bedroom downstairs and built in 2014. Volume, two story great room open up to kitchen ...

CHARMING CIRCA 1922 WINTER PARK CRAFTSMAN ON .37 ACRE LOT! Pride of Ownership apparent in this precious & impeccably maintained home. Main house 2150 sq ft + detached 20...

Fantastic opportunity in the Dommerich School District! 4 bedroom, 2 bath pool home with ¼ acre lot. Open layout with separate dining room, great room, and updated kitche...

An oversized lot in Winter Park walking to Brookshire and Winter Park High, this 3-bedroom 2-bath split plan is a rare find. This expansive lot wraps the corner with a bl...

This Winter Park Pines home offers unique 3-way split living plan with an abundance of space for every family member. Mostly updated, this home offers a spacious kitche...

Under Construction. "Under Construction" Brand NEW energy-efficient home ready June 2019! This Wimberley II home's chef-inspired kitchen overlooks the spacious family roo...

Under Construction. "Under Construction" Brand NEW energy-efficient home ready March 2019! This Pomelo home features a stunning modern elevation. Gourmet kitchen overlook...

Under Construction. "Under Construction" Brand NEW energy-efficient home ready May 2019! Use this Florentine's first-floor flex room as a formal living or dining room, or...

Under Construction. "Under Construction" Brand NEW energy-efficient home ready May 2019! The Pomelo is an open floor plan home with lots of flexibility. Flex space can be...

Under Construction. "Under Construction" Brand NEW energy-efficient home ready March 2019! Formal living and dining areas off the foyer flow to the kitchen and family roo...