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Winter Park, FL Real Estate — Homes For Sale in Winter Park, FL

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Winter Park Real Estate Overview

Originally founded as a resort destination by affluent New Englanders in the late 1880s, Winter Park is today known for its majestic trees, beautiful parks, brick-lined streets, stunning homes, a private liberal arts college, educational museums, sparkling lakes, and amazing shops. Winter Park is located just 15 minutes from the...
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$774,900
$2,870/mo
Monthly Payment:
$2,870
Principal & Interest:
$2,870
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $154,980 down)

660 Ololu Drive NEW Added to the site in the last 3 days

Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 3bath 2,427sq ft $319 / sq ft SFR
Lot Size21,852sq ft Built1986 On Site2days
Lake killarney dream home. When you walk into this beautiful custom home, you have an immediate feeling of tranquility. Enjoy sunrises, or relaxing evenings on your expansive... more
Lake killarney dream home. When you walk into this beautiful custom home, you have an immediate feeling of tranquility. Enjoy sunrises, or relaxing evenings on your expansive screened patio overlooking beautiful lake killarney. Built in 1986, this home was designed with simple elegance and functionality in mind. Vaulted ceilings provide a feeling of openness and the split plan allows for privacy and ease of living. The master and bedroom 3 have views of the lake and offer direct access to the expansive screened patio overlooking lake killarney. The master bath features his and hers sinks, garden jacuzzi tub, separate shower stall and spacious 7”x7” walk in closet. All bedrooms feature walk-in closets and there is abundant storage space throughout this home. The kitchen offers a dine in design with views of the lake for your morning coffee. mature, lake irrigated landscaping with just the right balance of ground cover and well groomed trees and shrubbery make this an easy maintenance home in a scenic setting. Access to your deepwater boat dock is just steps away via the concrete walkway where you will find a boat lift for easy enjoyment of the lake with the vessel of your choice. the oversized 2 car attached garage is amazingly spacious, clean, and secure. The best way to experience this home is setup a showing today. Don’t miss this rare opportunity to own this well appointed, beautiful lakefront home close to everything great winter park and tranquil lakefront living has to offer. less
Listing Provided Courtesy of Silva & Roberts Llc
Popularity N/A
Your search results are current and complete. Learn more
$1,674,900
$6,205/mo
Monthly Payment:
$6,205
Principal & Interest:
$6,205
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $334,980 down)

620 Gaines Way NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
4bed 5bath 4,422sq ft $379 / sq ft SFR
Lot Size14,018sq ft Built2016 On Site3days
Pre-Construction in Highly sought after Olde Winter Park. Contemporary masterpiece will be meticulously crafted by FG Schaub Custom Homes. This modern understated home will have... more
Pre-Construction in Highly sought after Olde Winter Park. Contemporary masterpiece will be meticulously crafted by FG Schaub Custom Homes. This modern understated home will have 4 bedrooms and 4.5 bathrooms with 4,385 sq ft of living space and a 3 car garage. Thoughtfully designed for innovative living by David Larson, Ltd. The dramatic two-story stairwell allows light to flow through the open living spaces and leads to the great room with gorgeous views of the contemporary pool through the accordion glass wall. Just off the great room is a Grand “transitional” room adding over 400 sq ft of additional living space and is complete with energy efficient roll away screens. This soft tones, clean lines, and natural textures will impress the most discriminating buyers. The Gorgeous island kitchen has custom cabinets, 48” dual fuel gas range, 48” built in refrigeration, and walk-in pantry. The first floor master will be truly fantastic with clean lines and elegant, simple finishes. You will easily access the beautiful pool from the master, blending the indoor-outdoor living. There will be impressive views of Lake Maitland for the second story balcony of this home. Energy saving features include: tank less hot water heater, vinyl low “E” windows, spray foam insulation, NEST smart thermostat, LED lighting, injected foam in block walls, just to name a few. This home will have the distinguished Signature Landscape package to complete this modern marvel. less
Listing Provided Courtesy of La Rosa Realty, Llc
Popularity
$279,000
$1,309/mo
Monthly Payment:
$1,309
Principal & Interest:
$1,033
HOA Dues:
$276
(Based on a 30 year fixed loan at 3.75% with $55,800 down)
Winter Park, FL 32789
Orange County School District
2bed 3bath 1,214sq ft $230 / sq ft CND
Lot Size5,861sq ft Built1986 On Site4days
Best view of Lake Killarney in Winter Park - Completely Remodeled and Open Floorplan On the shores of Lake Killarney in Winter Park! - End Unit - Very Private - Large and... more
Best view of Lake Killarney in Winter Park - Completely Remodeled and Open Floorplan On the shores of Lake Killarney in Winter Park! - End Unit - Very Private - Large and inviting with water views from Kitchen, Breakfast Nook, Master Bedroom and Living Room with Floor to Ceiling Marble Fireplace - Hardwood & Marble Flooring - Private screened in balcony for your morning coffee or evening sunset. Double master bedrooms with full baths and large closets - Crystal Chandelier - Oversized Stainless Fan - Indoor Laundry includes Washer/Dryer - Private amenities give you exclusive use of the gorgeous community pool, dock and beach where you can park your boat - Near Trader Joes, Winter Park Village and minutes from Park Avenue less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$387,000
$1,433/mo
Monthly Payment:
$1,433
Principal & Interest:
$1,433
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $77,400 down)
Winter Park, FL 32792
Golfside Orange County School District
4bed 2bath 2,552sq ft $152 / sq ft SFR
Lot Size10,772sq ft Built1968 On Site4days
Location!! Location!! You do not want to miss this opportunity to call this beautiful place home in the sought after neighborhood of winter park pines. This 4 bedroom/2 bath... more
Location!! Location!! You do not want to miss this opportunity to call this beautiful place home in the sought after neighborhood of winter park pines. This 4 bedroom/2 bath home boasts 2582 square feet with a 2-car garage and a partial golf-course view. Experience the pride of ownership with an open and updated kitchen featuring a large island, granite counter tops, work center, wood-burning brick fireplace, split floor plan and spacious bedrooms with large closets containing built-ins for extra storage. The large, bright florida room is the focal point of the home featuring cathedral ceilings and sky lights making it the perfect place for relaxing. Other improvements you are sure to enjoy include roof (2005), a/c (2012), re-plumbed (2006) and updated electrical (2006). This home is not only situated in a highly sought after a-rated school district, but is conveniently located within walking distant to the cady way trail and lies within the historic city of winter park that brings some of the finest dining, retail shopping, art festivals, entertainment and farmer's markets that central florida has to offer. All information recorded in the mls is intended to be accurate however, it should be independently verified. less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$1,079,900
$4,000/mo
Monthly Payment:
$4,000
Principal & Interest:
$4,000
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $215,980 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,160sq ft $342 / sq ft SFR
Lot Size10,251sq ft Built2006 On Site4days
Traditional Winter Park home on a tree lined, brick street. This warm and welcoming residence was custom built by Arlington Homes and shows like a model. Extensive millwork and... more
Traditional Winter Park home on a tree lined, brick street. This warm and welcoming residence was custom built by Arlington Homes and shows like a model. Extensive millwork and real hardwood floors are just a few of the special touches this home features. Solid wood cabinetry, hammered copper countertops and handmade custom glass are some of the features of this open, functional kitchen. The large and airy master suite has a fantastic shower with body jets, a large soaking tub, dual walk in closets and a convenient laundry right off the bath. The expansive great room features a gas fireplace and an entertainment center. The upstairs has 3 large bedrooms and a great loft for the kids to enjoy their activities. The upstairs also has its own stackable W/D. Energy features include Andersen Doors and Windows, 2 speed Trane Air handlers with a HEPA electronic filtration system, new wireless thermostats, 2 tankless gas water heaters and radiant barrier insulation. The home is prewired for a generator with a separate pad and panel. The detached garage sits in the back of this very deep (157') lot and has a 382 sf finished storage space above. The very private backyard has a saltwater pool with an in floor cleaning system for low maintenance enjoyment. The front and back porches have tongue and groove cypress ceilings. The lanai has a complete summer kitchen for relaxing and entertaining. Add "A" rated schools and a wonderful location and you have found the perfect place to call home! Make an appointment today! less
Listing Provided Courtesy of Coledev Real Estate Llc
Popularity
$225,000
$833/mo
Monthly Payment:
$833
Principal & Interest:
$833
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $45,000 down)
Winter Park, FL 32789
Orange County School District
2bed 1bath 850sq ft $265 / sq ft SFR
Lot Size6,179sq ft Built1950 On Site4days
Great opportunity to own in the heart of Winter Park. Walk to shopping, dining, entertainment on Park Ave and Hannibal Square. Value is mostly in the land. Location, location,... more
Great opportunity to own in the heart of Winter Park. Walk to shopping, dining, entertainment on Park Ave and Hannibal Square. Value is mostly in the land. Location, location, location! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$325,000
$1,204/mo
Monthly Payment:
$1,204
Principal & Interest:
$1,204
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $65,000 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 3bath 1,852sq ft $175 / sq ft SFR
Lot Size13,293sq ft Built2002 On Site5days
Newer home built in 2002 and already upgraded with granite counter tops, all new flooring, freshly painted inside and out. All this and new appliances. This home features a... more
Newer home built in 2002 and already upgraded with granite counter tops, all new flooring, freshly painted inside and out. All this and new appliances. This home features a large great room, 10 foot ceilings throughout the first floor with French doors leading to a deck overlooking the private back yard with plenty of room to play. You will love the convenience of an inside laundry room and a 2 car garage. Termite and pest control have been serviced regularly as home was built with tubes in the walls for easy treatment. You will not find a more convenient location, close to I-4 and all Winter Park, College Park and downtown Orlando has to offer. less
Listing Provided Courtesy of Classic Homes
Popularity
$1,295,000
$4,797/mo
Monthly Payment:
$4,797
Principal & Interest:
$4,797
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $259,000 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 4,367sq ft $297 / sq ft SFR
Lot Size12,900sq ft Built2001 On Site5days
Stunning Lake Killarney lakefront home! Five bedrooms, three and one-half baths, over 5,000 SF of open living. Downstairs master suite offers sunrise views, a jetted tub,... more
Stunning Lake Killarney lakefront home! Five bedrooms, three and one-half baths, over 5,000 SF of open living. Downstairs master suite offers sunrise views, a jetted tub, frameless shower, his and her vanities and a walk-in closet. Carrera marble kitchen is a chef’s dream come true with gas range, double ovens, and custom cabinetry. Family room off the kitchen features French doors that open onto the covered brick patio, while the informal dining room centers on the cozy fireplace. Upstairs are four generously sized bedrooms, each with oversized walk-in closets. Walk out balcony takes advantage of the lakefront views and is the perfect place to pull up a chair and relax. Gorgeous lawn and gardens have South East views overlooking the lake. Home has been meticulously cared for and beautifully decorated. Easy to show with just a little notice. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$129,900
$721/mo
Monthly Payment:
$721
Principal & Interest:
$481
HOA Dues:
$240
(Based on a 30 year fixed loan at 3.75% with $25,980 down)
Winter Park, FL 32789
Orange County School District
2bed 3bath 1,130sq ft $115 / sq ft CND
Lot Size15,664sq ft Built1986 On Site5days
Rare opportunity in Sandlewood Creek Condos! Private corner location with assigned parking right at your door. Sunny kitchen with bay window seat. Updated kitchen with new... more
Rare opportunity in Sandlewood Creek Condos! Private corner location with assigned parking right at your door. Sunny kitchen with bay window seat. Updated kitchen with new cabinets, granite composite counter tops and shiny stainless sink. Tile floors throughout the first level. Spacious outdoor patio with privacy wall. The powder room is updated to impress with new cabinets and granite counter tops. You will love this open great room with cozy wood fireplace. Upstairs the spacious master bedroom offers soaring vaulted ceiling and crown molding detail. The master bath is beautifully updated with new soaking tub, tile, cabinets, granite and faucet. Crown molding completes the luxurious bath. The second bedroom includes a private full bath. Full size washer and dryer included! Exceptional location with top rated Winter Park Schools. See this home today, it won't last! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$749,000
$2,774/mo
Monthly Payment:
$2,774
Principal & Interest:
$2,774
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $149,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,765sq ft $271 / sq ft SFR
Lot Size13,013sq ft Built1990 On Site5days
Key West meets Winter Park at this renovated sparkling gem of a home on one of Winter Park’s most beautiful brick streets. Light, bright and open with soaring ceilings... more
Key West meets Winter Park at this renovated sparkling gem of a home on one of Winter Park’s most beautiful brick streets. Light, bright and open with soaring ceilings and lots of windows. Three way split plan with 3 bedrooms/2 baths on one side of home and on the other is master suite with luxurious bath, double vanity, and walk-in closet. Separate living room, dining room, and kitchen open to family room with amazing view of spacious backyard and pavered patio. Kitchen has granite, newer stainless steel appliances, double oven, built-in desk, and adjacent wet bar. Everything in home has been very well maintained or completely renovated. Numerous improvements include all new top-of-the-line tile floors in main rooms, new wood floors in 3 bedrooms, renovated bathrooms, new Trane AC, new attic insulation, new landscaping & fence, new light fixtures and fans, new garage doors/cabinets/storage system, and interior and exterior repainted. Features include plantation shutters, custom built-ins, double sided fireplace, interior laundry room, closet organization systems, full alarm system and video system. Great location, walking distance to Phelps Park and downtown Winter Park. “A” rated schools. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$675,000
$2,504/mo
Monthly Payment:
$2,504
Principal & Interest:
$2,500
HOA Dues:
$4
(Based on a 30 year fixed loan at 3.75% with $135,000 down)
Winter Park, FL 32789
Orange County School District
5bed 3bath 3,136sq ft $215 / sq ft SFR
Lot Size18,991sq ft Built1967 On Site5days
WELCOME to your new home in Winter Park! Perfectly located in a secluded 32789 neighborhood with sidewalks, this FIVE bedroom THREE bath ONE STORY home has EVERYTHING you have... more
WELCOME to your new home in Winter Park! Perfectly located in a secluded 32789 neighborhood with sidewalks, this FIVE bedroom THREE bath ONE STORY home has EVERYTHING you have been searching for! Beautiful .44 acre corner lot on a serene tree-lined street includes a sprawling 700 square feet lanai for additional entertaining overlooking a sparkling, screened 32 x 16 pool with a private park-like backyard. Expect to be impressed by the completely remodeled kitchen with an AMAZING over 9 foot long granite island & stainless steel appliances flowing directly into your family room with a custom fireplace, built-ins & French doors opening to lanai & pool. Large elegant separate formal living & formal dining rooms are sure to delight. Hardwood floors and crown molding throughout your living and dining areas, and enjoy music of your choice through the built in surround sound speakers. The split floor plan offers large bedrooms & 3 full baths. Convenience to shopping a great bonus! Additional features include: LARGE inside laundry room PLUS 3 car side-entry garage. Zoned for Dommerich, Maitland, Winter Park High! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$189,000
$700/mo
Monthly Payment:
$700
Principal & Interest:
$700
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $37,800 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size6,180sq ft BuiltN/A On Site5days
Build your dream home in the hottest new location in Winter Park. Walking distance to Park Avenue and Winter Park Village.
Build your dream home in the hottest new location in Winter Park. Walking distance to Park Avenue and Winter Park Village. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$47,000
$174/mo
Monthly Payment:
$174
Principal & Interest:
$174
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $9,400 down)
Winter Park, FL 32792
1bed 1bath 678sq ft $69 / sq ft CND
Lot Size655sq ft Built1973 On Site6days
Bank owned, sold "as is" this condo is a ground floor 1 bedroom 1 bathroom with a covered porch. Located near ucf, full sail, rollins college, downtown winter park and... more
Bank owned, sold "as is" this condo is a ground floor 1 bedroom 1 bathroom with a covered porch. Located near ucf, full sail, rollins college, downtown winter park and much more. The stratford condominiums furnish the water and sewer. Cash offers only. Hoa requires owner/occupant. No investors at this time. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$70,000
$259/mo
Monthly Payment:
$259
Principal & Interest:
$259
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $14,000 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 840sq ft $83 / sq ft CND
Lot Size5,668sq ft Built1990 On Site6days
Great condo with Granite Countertops in Kitchen and Bathrooms, with newer range, dishwasher, washer and dryer a WIDE OPEN floor plan, breakfast bar, newer fans, mirrored closet... more
Great condo with Granite Countertops in Kitchen and Bathrooms, with newer range, dishwasher, washer and dryer a WIDE OPEN floor plan, breakfast bar, newer fans, mirrored closet doors. Lancelot is a wonderful community featuring a sparkling pool...this special home really has it all! An ideal location only a few minutes to downtown Orlando, UCF, Valencia, Full Sail, Rollins College, theme parks, beaches, airport, highways 417 & 408, entertainment, dining & shopping! Hurry and Make Offer today, won't last long. less
Listing Provided Courtesy of Realty Executives Seminole
Popularity
$1,474,900
$5,464/mo
Monthly Payment:
$5,464
Principal & Interest:
$5,464
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $294,980 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,179sq ft $353 / sq ft SFR
Lot Size12,270sq ft Built2016 On Site6days
Pre-Construction in Olde Winter Park near beautiful Lake Sue. Stunning Contemporary Home will be meticulously crafted by FG Schaub Custom Homes. This home will boast a clean and... more
Pre-Construction in Olde Winter Park near beautiful Lake Sue. Stunning Contemporary Home will be meticulously crafted by FG Schaub Custom Homes. This home will boast a clean and understated approach that will reveal a modern aesthetic and sense of place. Crediting the design to David Larson, Ltd. This home will make extensive use of windows allowing natural light to flow through the open living space. The first floor Master suite will have modern features and a walk in closet of nearly 150 sq. ft. This modern masterpiece will have a formal dining room, 4 bedrooms and 4.5 bathrooms, an over sized walk through pantry, with access to the kitchen which will have all of the latest cutting edge features: including a Thermador appliance package, custom cabinets, Quartz counter tops, and 90 degree Moen faucets . The great room overlooks the pool and provides access to the grand “transitional” room adding nearly 400 sq ft with roll away screens. Plus a summer kitchen that allows for a perfect blend of indoor-outdoor living. Beautiful outdoor package by Signature Landscape. Energy saving features include: tank less hot water heater, vinyl low “E” windows, spray foam insulation, NEST smart thermostat, LED lighting, injected foam in block walls. All this on a private, cul-de-sac and with a 3 car garage! This home will have the distinguished Signature Landscape package to complete this Modern Marvel. Easy 15 minute commute to Florida Hospital and neighboring facilities. less
Listing Provided Courtesy of La Rosa Realty, Llc
Popularity
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ZipRealty helps you find current homes for sale in Winter Park, FL. We show up to 30% more MLS listings than other websites, including new homes for sale, condos for sale, townhomes for sale, foreclosed homes for sale and land for sale. Set up your unique Winter Park real estate search criteria to see results that match what you're looking for. Explore maps, photos, schools and more to get an idea of what your life would be like in a new neighborhood. Find a local Winter Park real estate agent to work with by reading realtor reviews left by buyers and sellers like you. If you want to know what your home is worth, you can instantly view home values for any address by visiting our Seller Center. If you're planning to sell your home, you can also see how much similar homes are selling for in Winter Park to get an idea of how to price your home.
Local real estate services provided by:
Coldwell Banker Residential Real Estate
Coldwell Banker Residential Real Estate
5951 Cattleridge Ave
Sarasota, FL 34232

844.662.5638
Website provided and owned by Coldwell Banker Residential Real Estate.
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The information being provided by Mid-Florida Regional Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Mid-Florida Regional Multiple Listing Service. Coldwell Banker Residential Real Estate is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Coldwell Banker Residential Real Estate, a broker participant of Mid-Florida Regional Multiple Listing Service. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.

The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Mid-Florida Regional Multiple Listing Service and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited.

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Data last updated: Sunday, August 30, 2015 at 8:59 PM. Properties in listings may have been sold or may no longer be available.