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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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$135,000
$500/mo
Monthly Payment:
$500
Principal & Interest:
$500
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $27,000 down)
Winter Park, FL 32792
2bed 2bath 1,219sq ft $111 / sq ft CND
Lot Size19.0acre Built1970 On Site37days
HOA, Includes water, sewer, garbage collection, 3 pools, lawn maintenance, tennis courts, shuffleboard, and car wash. Highly desired area.
HOA, Includes water, sewer, garbage collection, 3 pools, lawn maintenance, tennis courts, shuffleboard, and car wash. Highly desired area. less
Listing Provided Courtesy of Assist 2 Sell Veterans Realty
Popularity
Your search results are current and complete. Learn more
$119,900
$444/mo
Monthly Payment:
$444
Principal & Interest:
$444
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $23,980 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 1,127sq ft $106 / sq ft CND
Lot Size19.0acre Built1970 On Site37days
Walk to Publix, pharmacies, banks within the area. Short Drive to Park ave, Farmer's Market. Close to Full Sail.
Walk to Publix, pharmacies, banks within the area. Short Drive to Park ave, Farmer's Market. Close to Full Sail. less
Listing Provided Courtesy of Winter Park Land Co.
Popularity
$899,000
$3,330/mo
Monthly Payment:
$3,330
Principal & Interest:
$3,330
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $179,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,384sq ft $266 / sq ft SFR
Lot Size9,009sq ft Built2015 On Site37days
Olde winter park welcomes another lundev fabulous new custom home! This quiet location on a tree-lined cul-de-sac offers contemporary quality touches while offering energy... more
Olde winter park welcomes another lundev fabulous new custom home! This quiet location on a tree-lined cul-de-sac offers contemporary quality touches while offering energy efficient features. Covered entryway welcomes you inside to be greeted with designer wood floors. This family home offers a large gathering area with a spacious family room complete with a gas fireplace. The gourmet kitchen offers bosch appliances centered around a large kitchen island topped with a beautiful granite top amid custom maple cabinetry. Venture outside to a covered patio overlooking the yard with room for a pool. Luxurious first floor master bedroom offers plenty of storage in the large walk-in closet while the mbr bath features his and her vanities with a garden tub and separate shower stall. There's a second br also on the first floor . Privacy awaits in the downstairs library/den for family chats. Upstairs you'll find two additional bedrooms and a loft - perfect for a playroom or media room. This location is a short bike ride to famed park ave. And offers a schools: dommerich elem/maitland mid/wp high. Easy commuter access to 417. Call today for your private showing! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$174,900
$647/mo
Monthly Payment:
$647
Principal & Interest:
$647
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $34,980 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 2bath 1,120sq ft $156 / sq ft SFR
Lot Size7,000sq ft Built1954 On Site38days
Nice 3 bed 2 bath home in Winter Park. This property is a part of Freddie Mac’s First Look Program. Freddie Mac will only consider owner occupant buyers and second home... more
Nice 3 bed 2 bath home in Winter Park. This property is a part of Freddie Mac’s First Look Program. Freddie Mac will only consider owner occupant buyers and second home buyers through August 15, 2015 . No investor offers will be considered until after the 20th day on the market. All information including square footage, land area and HOA fees to be verified by the buyer. less
Listing Provided Courtesy of Croft Real Estate Service Llc
Popularity
$169,900
$629/mo
Monthly Payment:
$629
Principal & Interest:
$629
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $33,980 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
3bed 2bath 1,366sq ft $124 / sq ft SFR
Lot Size8,918sq ft Built1978 On Site38days
This lovely stucco and stone home has a brand new roof and the interior is completely updated, new kitchen, fresh paint, new bathroom vanities! With a pool and jacuzzi in the... more
This lovely stucco and stone home has a brand new roof and the interior is completely updated, new kitchen, fresh paint, new bathroom vanities! With a pool and jacuzzi in the backyard, this house has plenty of space for company. The screened patio keeps parties happy and bug-free, and the dog can hang around in the fenced backyard or join the party in the pool. With such an open floor plan, you'll feel right at home moving from the kitchen to the living room and onto the patio. less
Listing Provided Courtesy of Lemontree Realty Llc
Popularity
$229,900
$851/mo
Monthly Payment:
$851
Principal & Interest:
$851
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $45,980 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,458sq ft $158 / sq ft SFR
Lot Size8,400sq ft Built1969 On Site38days
updated 3/2 split plan with living & family rooms, updated kitchen and bathrooms. Great established neighborhood.
updated 3/2 split plan with living & family rooms, updated kitchen and bathrooms. Great established neighborhood. less
Listing Provided Courtesy of Premium Properties R.e Service
Popularity
$398,000
$1,474/mo
Monthly Payment:
$1,474
Principal & Interest:
$1,474
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $79,600 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,326sq ft $300 / sq ft SFR
Lot Size7,487sq ft Built1998 On Site38days
Turn-Key ready.. immaculate, impeccably maintained and cared for; this 1998 3-bedroom/ 2-bath split plan retreat plays above size with finished garage, outside storage and... more
Turn-Key ready.. immaculate, impeccably maintained and cared for; this 1998 3-bedroom/ 2-bath split plan retreat plays above size with finished garage, outside storage and 9-foot-ceilings throughout, under a 200mph hurricane rated modern hip-roof. Retreat to your own romantic, in-town, backyard garden paradise. Perfect for the weekend gardener and entertaining. No HOA fees, easy to maintain, efficient. A short walk from your front door are coffee houses, restaurants, locally owned shops, brew-pubs, botanic gardens, events, and artisan markets. Roll up the blankets and walk/ bike to a Jazz Fest at Leu Gardens, no Uber needed! Wood floors, french doors, updated fireplace, location, and open plan all make this home perfect for entertaining. Close to Leu Gardens, Mead Gardens, Blue Jacket Park, Baldwin Park shops and restaurants, Florida Hospital, Orlando Health, Rollins College, Park Avenue, East End Market, and more. Finished garage and backyard storage shed keep things neat and roomy. A-Rated Winter Park schools. Perfect for the active Winter Park/ Orlando lifestyle. less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity
$4,999,999
$18,524/mo
Monthly Payment:
$18,524
Principal & Interest:
$18,524
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $1,000,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 6,113sq ft $818 / sq ft SFR
Lot Size1.2acre Built2006 On Site38days
Located in the heart of Winter Park within walking distance to Park Ave, Winner of the 2007 Parade of homes, this custom home will not disappoint you. This 1.25 acre estate... more
Located in the heart of Winter Park within walking distance to Park Ave, Winner of the 2007 Parade of homes, this custom home will not disappoint you. This 1.25 acre estate boasts over 200 feet of water front on Lake Mizell, a part of Winter Park’s chain of lakes. Quality detail runs throughout the 6000 SF of elegant living area with MISSONI carpet in the upstairs bedrooms, extensive crown moulding and soffit ceilings throughout the entire house. The Beautiful Chef’s kitchen includes an oversized island, Viking built-in appliances, gas cooktop with 6 burners, double fridge with a bottom freezer and wooden cabinetry. The oversized master suite is located on the ground floor with 2 walk in closets and exquisite detailed bathroom. Spacious family room with hardwood floors, large sliding doors open up to slate lanai, which overlooks the pool and lake. Home theater with brand new equipment, leather reclining chairs and 8 foot projector screen. The house has a 4 car garage with extra outside space for a boat and trailer. The backyard features a large pool with beach style entry overlooking at the lake. The property has a private composite boat dock with automatic boat lift, generator and tankless water heater. Detached two story guest house has a summer kitchen and exercise room. less
Listing Provided Courtesy of Regal R.e. Professionals Llc
Popularity
$2,500,000
$9,302/mo
Monthly Payment:
$9,302
Principal & Interest:
$9,262
HOA Dues:
$40
(Based on a 30 year fixed loan at 3.75% with $500,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,846sq ft $516 / sq ft SFR
Lot Size43,124sq ft Built1972 On Site38days
Welcome to your Lake Sue Dream Estate. Featured in Winter Park Magazine, this beautiful two story block French Provincial home is on 200+ ft of prestigious waterfront and... more
Welcome to your Lake Sue Dream Estate. Featured in Winter Park Magazine, this beautiful two story block French Provincial home is on 200+ ft of prestigious waterfront and approximately 1 acre of land. Built from olde Chicago brick salvaged from the Chicago River in one of Winter Parks only walled neighborhoods, Sevilla. Near to downtown Winter Park, Orlando, shopping, and A-rated schools. Enter the estate at the end of a private cul-de-sac on a magnificent herringbone brick circle drive (2010). Lush, mature utopia with cypress, oak, elm, and camphor trees. Top of the line boathouse, electronic lift. Wrought iron fenced solar heated pool maintains vast lake vistas. Grand, marble entry sweeps into open, traditional dining/living rooms, full of light. Lake views in almost every room. First floor master with office/nursery renovated 2010. The best finishes in master bath: custom cabinetry, granite, porcelain floor tiles, LeFroy fixtures, and Kaldwei iron soaking tub. Kitchen renovated 2010 with custom island and cabinetry, Miele appliances, walk-in pantry, and separate lined silver pantry. Large family room with wood-burning fireplace and built-ins. Bonus area upstairs with more built-ins and four oversized bedrooms. ainscoting in mud/breakfast room, cedar ski closet, ample storage, working shutters, Wirepath Surveillance system, new roof and water heaters, new Pella doors/windows, refrigerated wine storage, basketball area, extra covered parking. Must see if you enjoy lakefront living in a superior location! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$71,500
$551/mo
Monthly Payment:
$551
Principal & Interest:
$264
HOA Dues:
$287
(Based on a 30 year fixed loan at 3.75% with $14,300 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 1,018sq ft $70 / sq ft CND
Lot Size4,228sq ft Built1984 On Site39days
2 Bedroom, 2 bath condo located on the 2nd floor! Condo features a spacious main living area with sliding doors to access your screened patio. The kitchen features breakfast bar... more
2 Bedroom, 2 bath condo located on the 2nd floor! Condo features a spacious main living area with sliding doors to access your screened patio. The kitchen features breakfast bar with access from the living room. The master suite features a private bathroom with shower and walk in closet. There is also another full bath with tub/shower combination. There is an inside laundry room for added convenience. The complex offers community pool, spa, playground, sport court and clubhouse. Conveniently located close to schools, shopping, dining and major highways. This is a Fannie Mae HomePath property. less
Listing Provided Courtesy of Re/max Town & Country Realty
Popularity
$1,081,000
$4,005/mo
Monthly Payment:
$4,005
Principal & Interest:
$4,005
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $216,200 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 4,900sq ft $221 / sq ft SFR
Lot Size16,962sq ft Built1954 On Site39days
Just reduced! This 5 bedroom 5 bath 5 car garage canal front home is located on a secluded lot with stunning views of the canal that has access to the winter park chain of... more
Just reduced! This 5 bedroom 5 bath 5 car garage canal front home is located on a secluded lot with stunning views of the canal that has access to the winter park chain of lakes. Inside you are going to find a family room with fireplace, gourmet kitchen with granite counter tops, ample cabinet space a built in miele coffee maker and new stainless steel appliances. There is a home theater, wine room, and guest room downstairs. The master bedroom is upstairs on the south side of the home with a balcony overlooking the canal and pool area. On the north side second floor you will find three en suite bedrooms all with large walk in closets. Take the boat out of a sunset cruise from your private boat dock and then you will be ready to cool off in the crystal blue pool upon your return. Do not miss this opportunity to purchase this winter park canal front home in the winter park school district. See attachment for pas requirements and wfhm offer submittal information in mls document section. No digital or electronic signatures allowed by the seller. Seller should be owner of record. less
Listing Provided Courtesy of Fannie Hillman & Associates
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
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size8,125sq ft BuiltN/A On Site39days
Small 2/1 home on lot. Lake access deeded 25 Ft. on Lake Killarney - not attached. INCREDIBLE OPPORUNITY to own all that Lake Killarney has to offer! Additional 25' lakefront... more
Small 2/1 home on lot. Lake access deeded 25 Ft. on Lake Killarney - not attached. INCREDIBLE OPPORUNITY to own all that Lake Killarney has to offer! Additional 25' lakefront lot available for total package at $350,000. Additional 125 feet on water also available - see 430 Killarney Drive. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$169,900
$629/mo
Monthly Payment:
$629
Principal & Interest:
$629
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $33,980 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
4bed 3bath 1,736sq ft $98 / sq ft SFR
Lot Size9,774sq ft Built1970 On Site39days
Looking for Winter Park schools AND 4 bedrooms/3 full baths? With a pool & spa? UNDER $170,000? THIS COULD BE YOUR NEXT HOME! Want a Family Room with fireplace, separate Living... more
Looking for Winter Park schools AND 4 bedrooms/3 full baths? With a pool & spa? UNDER $170,000? THIS COULD BE YOUR NEXT HOME! Want a Family Room with fireplace, separate Living Room, a big open Kitchen with breakfast bar and a 1 car garage, AND 2 extra carports? Here's your chance! Beautiful sparkling open pool and spa (new pumps!), with a backyard big enough for friends & fun. Covered parking pad behind your privacy fence could house your RV or boat, OR become a gazebo for poolside entertaining. With a fire pit! House has over 1700 heated & cooled square feet, but lives REALLY BIG. The previous owner made some updates and additions, but there's LOTS of room for creativity & custom touches to make this spacious house YOUR home! COME BY and LOOK US OVER! **This is a Fannie Mae HomePath Property. “First Time Buyers, complete the HomePath Ready Buyer homeownership course on the HomePath website. Attach certificate to offer and request up to 3% closing cost assistance. Check the HomePath website for more details or ask your Realtor. Restrictions apply.” All information recorded in the MLS is intended to be accurate but cannot be guaranteed, buyer advised to verify. less
Listing Provided Courtesy of Profitable Properties
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
Orange County School District
2bed 1bath 1,021sq ft $318 / sq ft SFR
Lot Size7,500sq ft Built1947 On Site39days
Charming 2 bedroom 1 bath home with detached 25' Lakefront Lot on Lake Killarney. INCREDIBLE OPPORTUNITY to own all that Lake Killarney has to offer! Additional 25' lakefront... more
Charming 2 bedroom 1 bath home with detached 25' Lakefront Lot on Lake Killarney. INCREDIBLE OPPORTUNITY to own all that Lake Killarney has to offer! Additional 25' lakefront lot also available for total package at $350,000. Adjacent property at 430 Killarney Drive can be purchased for $800,000 with 125' Lakefront on Lake Killarney. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$249,900
$928/mo
Monthly Payment:
$928
Principal & Interest:
$925
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $49,980 down)
Winter Park, FL 32792
Orange County School District
4bed 2bath 1,596sq ft $157 / sq ft SFR
Lot Size10,346sq ft Built1964 On Site39days
Enjoy classic Winter Park charm in this beautiful 4 bedroom/2 bath corner lot home in the highly sought after community of Winter Park Pines. House has newer plumbing, A/C and... more
Enjoy classic Winter Park charm in this beautiful 4 bedroom/2 bath corner lot home in the highly sought after community of Winter Park Pines. House has newer plumbing, A/C and upgraded electrical, roof replaced in 2006. Spacious kitchen features plenty of cabinets and stainless steel appliances and granite breakfast bar. Home features some laminate wood, enclosed screened patio, bright and open living space, separate dining area, fenced yard, side entry garage. Home is close to downtown Winter Park, schools, hospital and Cady Way. Seller is motivated, quick answer to offers. Bring your buyers to see this one!! Family room has new laminate floors to match dining room. less
Listing Provided Courtesy of Homecenter Realty Associates
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.

Copyright 2015 Mid-Florida Regional Multiple Listing Service. All rights reserved.

Data last updated: Wednesday, September 2, 2015 at 8:24 PM. Properties in listings may have been sold or may no longer be available.