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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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$249,500
$924/mo
Monthly Payment:
$924
Principal & Interest:
$924
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $49,900 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,277sq ft $195 / sq ft SFR
Lot Size9,589sq ft Built1958 On Site124days
Fabulous home located in the City of Winter Park boasts 3 bedrooms and 2 full baths. The Kitchen has been updated with new stainless steel appliances, dishwasher, disposal,... more
Fabulous home located in the City of Winter Park boasts 3 bedrooms and 2 full baths. The Kitchen has been updated with new stainless steel appliances, dishwasher, disposal, refrigerator and glass top stove for easy clean up. Lots of counter tops and storage for all your kitchen gadget and treats. The counter bar and service area open to the dining room will delight the cook and the tasters! Beautiful parquet flooring throughout the home and Cathedral Ceiling. The Large Living area has a Huge Window facing the back yard. The Kitchen and Bath rooms have ceramic tile floors. French doors in dining room leads the party out to the large, private fenced back yard. The Master Bedroom has a private full bath with shower stall. The home has a Utility Room for Laundry with tub sink and a work shop area located in the carport area. This home is located in a great school district, near shopping, Cady Way Bike Trail Park, Hospital, and Winter Park Wellness Center/YMCA. Built of Sold Block Construction! Move in ready, clean and fresh. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
Your search results are current and complete. Learn more
$3,525,000
$13,059/mo
Monthly Payment:
$13,059
Principal & Interest:
$13,059
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $705,000 down)
Winter Park, FL 32789
Orange County School District
6bed 7bath 6,763sq ft $521 / sq ft SFR
Lot Size1.7acre Built1991 On Site124days
Spectacular Winter Park Chain-of-Lakes Pool Home. Step inside to experience the true grandeur of this home~ the first view from the foyer is breath-taking with the 2-story... more
Spectacular Winter Park Chain-of-Lakes Pool Home. Step inside to experience the true grandeur of this home~ the first view from the foyer is breath-taking with the 2-story formal living room showcasing views of the pool, grounds and Lake Maitland. Originally built & designed by Randy Reyna in 1991, and renovated by Charles Clayton in 2004, this home has incredible living spaces. The kitchen offers top-of-the-line appliances including a Meile 6-burner gas range, double ovens & two side-by-side integrated Subzeros and a breakfast room/2nd dining room with a custom bar with a 52-bottle wine fridge. The private master suite has a sitting area/office, a marble fireplace, a 20x16 closet & a luxurious bath suite. A bedroom is adjacent to the master suite, and can be a fitness room, office or nursery. The formal dining room and family room complete the first floor, and creates the perfect space for entertaining with floor-to-ceiling windows. The expansive lanai overlooks the grounds and beautiful lake. The second floor has four bedroom en suites ~ three with access to the balcony that spans the width of the home. Extras include, but are not limited to: a great dock & boat house w/hoist, a 3-car garage w/storage space, two laundry rooms (one on each floor), Lutron lighting & surround-sound speakers throughout the first floor, and a state-of-the-art security system with video surveillance. Located in a premier Winter Park neighborhood~ walking distance to fine dining and shopping on Winter Park's renowned Park Ave. less
Listing Provided Courtesy of Not Available
Popularity
$759,000
$2,812/mo
Monthly Payment:
$2,812
Principal & Interest:
$2,812
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $151,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,932sq ft $259 / sq ft SFR
Lot Size1,300sq ft Built1969 On Site124days
Welcome home to park north, a great nieghborhood, walking distance to downtown winter park. Attractive brick front block home. Beautiful landscaping. Eat in kitchen, formal... more
Welcome home to park north, a great nieghborhood, walking distance to downtown winter park. Attractive brick front block home. Beautiful landscaping. Eat in kitchen, formal dining and living rooms. Fireplace in family room. Large master has a sitting room. Private, heated pool. Brand new heat and air systems, and a newer tile roof. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$429,000
$1,589/mo
Monthly Payment:
$1,589
Principal & Interest:
$1,589
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $85,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,153sq ft $199 / sq ft SFR
Lot Size7,720sq ft Built1957 On Site124days
Stunning home located in one of Winter Park’s most desirable neighborhoods! Completely renovated, this captivating, traditional style home features three bedrooms, three... more
Stunning home located in one of Winter Park’s most desirable neighborhoods! Completely renovated, this captivating, traditional style home features three bedrooms, three full baths and an open living and dining area filled with natural light. Character and charm flow throughout the home with meticulously maintained, original hardwood floors. An updated kitchen, featuring solid wood cabinets, granite countertops and a GE appliance package bring a modern touch to the home’s interior. Master suite is generous in size and offers an en suite with oversized soaking tub, separate shower and walk-in closet with custom built-ins. French doors lead to the open patio and allow for a relaxing environment, overlooking the professionally landscaped backyard. Located in the heart of Winter Park, among the mature oak trees, and within walking distance to “A” rated schools, do not miss the opportunity to lives just minutes from Winter Park’s celebrated Park Avenue and call this residence your home! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$485,000
$1,796/mo
Monthly Payment:
$1,796
Principal & Interest:
$1,796
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $97,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,386sq ft $203 / sq ft SFR
Lot Size10,546sq ft Built1951 On Site127days
Welcome Home! As you park on your driveway's custom pavers behind privacy hedges, you'll notice the majestic oak trees and wonderful landscaping. Upon entering, you'll... more
Welcome Home! As you park on your driveway's custom pavers behind privacy hedges, you'll notice the majestic oak trees and wonderful landscaping. Upon entering, you'll immediately feel this homes unique warmth and appeal. Beautiful hardwood floors greet you in your foyer and lead you through the home. Take a step up into your large living room which leads you to the downstairs bedrooms as well as into your kitchen. This kitchen has all the finishing touches, with stainless steel appliances, granite counter tops, stone backsplash, and tall cabinets complete with crown molding. Next to your kitchen is your charming dining room with built-ins and your spacious family room with volume ceilings, wood flooring, and plenty of natural light. Upstairs leads you to your private master suite. Enjoy lots of room, "his & her" walk in closets, and french doors that take you to your own walkout balcony. Your screened-in pool and patio has plenty of room to entertain the entire family, friends, and guests. The spa is automated and can be set from anywhere on your mobile device. Beyond your pool, you have a large backyard, with paver walkways taking you to additional spots to enjoy the outdoors. Conveniently located to the scenic Phelps Park as well as the Winter Park YMCA. You're minutes from Park Avenue, Whole foods, Top Schools, dining, entertainment, and much more. This home truly is in the heart of Winter Park. CALL US TODAY TO SET UP YOUR PRIVATE SHOWING!!! less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$2,395,000
$9,094/mo
Monthly Payment:
$9,094
Principal & Interest:
$8,873
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $479,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 6,175sq ft $388 / sq ft SFR
Lot Size20,640sq ft Built2005 On Site127days
Spectacular, private estate in prestigious Windsong! Built in 2005 & featuring five bedrooms, five & two-half baths, this home boasts 6,175 SF of neoclassical inspired interior... more
Spectacular, private estate in prestigious Windsong! Built in 2005 & featuring five bedrooms, five & two-half baths, this home boasts 6,175 SF of neoclassical inspired interior details. Grand two-story entry with stone columns invites guests into formal living & dining areas. Polished marble flooring, high ceilings, & magnificent wrought-iron staircase, combined with Illuminating natural light give this formal living area a palatial feel. Luxury continues throughout the home & into the designer kitchen, where solid wood cabinetry with hand-carved trimming, glass doors, granite countertops, & top-of-the-line chef’s appliances make this kitchen truly inspiring. Second living room off kitchen, has gas fireplace & built-in cabinetry with walk-thru to breakfast area & wet bar. Executive office, with floor to ceiling bookshelves & tray ceiling, maintain a studious environment for the professional in this home. Extravagant, downstairs master suite features lavish, two-story, solid-wood closet. Master bath leaves little to be desired with its jetted tub, large walk-in shower, & double vanities. Upstairs provides the perfect retreat for entertaining. Billiard room, with full bar overlooks downstairs living area, & home theater makes movie night at home a cinematic event. Three of the four upstairs bedrooms are generously sized & offer full bath, walk-in closets, & walk-out balcony. Resort style pool & spa, gazebo with summer kitchen, & covered patio exemplify outdoor living at its finest. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$544,000
$2,015/mo
Monthly Payment:
$2,015
Principal & Interest:
$2,015
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $108,800 down)
Winter Park, FL 32789
Orange County School District
5bed 3bath 3,079sq ft $177 / sq ft SFR
Lot Size9,066sq ft Built1959 On Site128days
Fantastic Family Home! 5 bedrooms, 2 car garage, updated thru out. Beautiful kitchen with stainless steel appliances and granite counter tops. Bathrooms are updated as well.... more
Fantastic Family Home! 5 bedrooms, 2 car garage, updated thru out. Beautiful kitchen with stainless steel appliances and granite counter tops. Bathrooms are updated as well. Crown molding thru out. Wonderful real wood flooring. Master upstairs has an additional space being used as an office. Back yard is private and has plenty of room for a pool if buyer needed. Winter Park Schools! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$995,000
$3,686/mo
Monthly Payment:
$3,686
Principal & Interest:
$3,686
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $199,000 down)
Winter Park, FL 32789
Orange County School District
5bed 3bath 3,756sq ft $265 / sq ft SFR
Lot Size11,239sq ft Built2006 On Site128days
Have you been searching for a unique Winter Park residence that offers you luxury living without the restrictions of a Homeowner's Association? Built in 2006, this expansive yet... more
Have you been searching for a unique Winter Park residence that offers you luxury living without the restrictions of a Homeowner's Association? Built in 2006, this expansive yet intimate villa will remind you of a castle. Boasting over 3,700 square feet, this property offers four bedrooms with two and a half bathrooms. You'll notice no detail has been spared, from arched doorways, Brazilian rosewood floors, back-lit tray ceilings, to a Venetian plaster wall treatment. This custom-built beauty offers a versatile floor plan with numerous bonus rooms, including a "man cave" with a coffered wood ceiling, and a study on the first floor. Tuscan half-columns flank the family room, which offers views of the sparkling Gothic-style pool and outdoor kitchen area. Functional and beautiful, the gourmet kitchen offers an abundance of space, a butcher block island, contrasting wood cabinets, stainless steel and gas appliances, and a walk-in pantry. The Master Suite includes plenty of space for oversized bedroom furniture and more! As you make your way into the Master Bathroom, you'll find that it boasts travertine tile, double sinks, a garden tub, walk-in shower and a large walk-in closet. Upstairs you will find plenty of closet space within each of the bedrooms. The study could easily be converted into a fifth bedroom. Located on a coveted corner lot across from Marvin Smiley Park, you'll enjoy park views and added privacy. Close to Florida Hospital and Park Avenue this location cannot be beat! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$249,000
$922/mo
Monthly Payment:
$922
Principal & Interest:
$922
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $49,800 down)
Winter Park, FL 32792
Goldenrod Orange County School District
3bed 2bath 1,676sq ft $149 / sq ft SFR
Lot Size8,424sq ft Built1968 On Site129days
Winter Park's secret neighborhood! WINTER PARK FOREST!! Located on a quiet Orange County cul-de-sac/dead end street. Corner lot provides extra side yard... more
Winter Park's secret neighborhood! WINTER PARK FOREST!! Located on a quiet Orange County cul-de-sac/dead end street. Corner lot provides extra side yard perfect for RV or boat storage! IMMACULATE split bedroom plan with updated kitchen & baths. Formal living & dining rooms plus kitchen opens to a spacious family room. 29 x 9 screened porch overlooks private, newly fenced yard & sparkling swimming pool!! Extras include: Natural gas, 2 car garage and Winter Park Schools: LAKEMONT ELEMENTARY, MAITLAND MIDDLE, WINTER PARK HIGH! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$879,553
$3,258/mo
Monthly Payment:
$3,258
Principal & Interest:
$3,258
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $175,911 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,204sq ft $275 / sq ft SFR
Lot Size12,797sq ft Built2014 On Site129days
Don't miss your opportunity to own a brand new David Weekley Home in the heart of Winter Park. This home will be pre construction for a limited time so hurry in to make all of... more
Don't miss your opportunity to own a brand new David Weekley Home in the heart of Winter Park. This home will be pre construction for a limited time so hurry in to make all of your interior selections before it is too late! less
Listing Provided Courtesy of Weekley Homes Realty Company
Popularity N/A
$815,455
$3,021/mo
Monthly Payment:
$3,021
Principal & Interest:
$3,021
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $163,091 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,084sq ft $264 / sq ft SFR
Lot Size9,884sq ft Built2014 On Site129days
Don't miss your opportunity to own a brand new David Weekley Home in the heart of Winter Park. This home will be pre construction for a limited time so hurry in to make all of... more
Don't miss your opportunity to own a brand new David Weekley Home in the heart of Winter Park. This home will be pre construction for a limited time so hurry in to make all of your interior selections before it is too late! less
Listing Provided Courtesy of Weekley Homes Realty Company
Popularity
$100,000
$613/mo
Monthly Payment:
$613
Principal & Interest:
$370
HOA Dues:
$243
(Based on a 30 year fixed loan at 3.75% with $20,000 down)
Winter Park, FL 32792
2bed 2bath 1,495sq ft $67 / sq ft CND
Lot Size2,030sq ft Built1981 On Site130days
Welcome to this two bedroom, two bath villa. This home features volume ceilings, wood burning fire place, walk in closets, upstairs loft, attic space for extra storage, bar area... more
Welcome to this two bedroom, two bath villa. This home features volume ceilings, wood burning fire place, walk in closets, upstairs loft, attic space for extra storage, bar area with sink, screen enclosed back porch and so much more. A MUST SEE! THIS PROPERTY IS BEING SOLD AS IS AND IS SUBJECT TO HUD GUIDELINES 24 CFR 206.125. less
Listing Provided Courtesy of Exit Real Estate Results
Popularity
$289,000
$1,070/mo
Monthly Payment:
$1,070
Principal & Interest:
$1,070
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $57,800 down)
Winter Park, FL 32792
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size3.5acre BuiltN/A On Site131days
Multi-family 3.5 acres. Sold as-is.
Multi-family 3.5 acres. Sold as-is. less
Listing Provided Courtesy of Re/max 200 Realty
Popularity N/A
$99,900
$370/mo
Monthly Payment:
$370
Principal & Interest:
$370
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $19,980 down)
Winter Park, FL 32792
Goldenrod Orange County School District
3bed 1bath 1,393sq ft $72 / sq ft SFR
Lot Size7,806sq ft Built1958 On Site134days
3 bed 1 bath home. 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 July 3... more
3 bed 1 bath home. 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 July 3 2014. 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
$1,125,000
$4,168/mo
Monthly Payment:
$4,168
Principal & Interest:
$4,168
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $225,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,018sq ft $373 / sq ft SFR
Lot Size29,526sq ft Built1954 On Site134days
Open Sat Oct 25, 2pm-5pm
Wonderful single story Mediterranean on expansive apprx. 30,000 SF elevated corner lot in premier Via's neighborhood with deeded access to Lake Maitland & Chain of Lakes via HOA... more
Wonderful single story Mediterranean on expansive apprx. 30,000 SF elevated corner lot in premier Via's neighborhood with deeded access to Lake Maitland & Chain of Lakes via HOA boat ramp & park lot... This split-level home (all bedrooms & living area on main level & huge 3 car garage & misc storage on lower level) has been meticulously maintained with numerous upgrades & remodeling by present owner while maintaining the character and charm of the 50's era... Fabulous well landscaped yard & grounds with motor court, circular drive & pool w/ cabana... This home has elegant hardwood floors thru-out, remodeled kitchen & baths with granite, extensive moldings and built-ins, 2 fireplaces, oversized master suite and more... the main residence has 3 BE & an office in addition to the living areas + a separate private 4th bedroom suite perfect for older child, in-laws, guest, or flex room (home office, media or exercise)... This is a fantastic property with lots of great characteristics to create a unique residence in prime location... walk to WPRC! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
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Local real estate services provided by:
Coldwell Banker Residential Real Estate
Coldwell Banker Residential Real Estate
5951 Cattleridge Ave
Sarasota, FL 34232
1.941.487.1400
Local service is provided by our preferred broker, Coldwell Banker Residential Real Estate. By logging on to ziprealty.com, you are authorizing ZipRealty to refer you to Coldwell Banker Residential Real Estate for real estate brokerage services, and ZipRealty will receive a referral fee or other valuable consideration for such referral.
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The information being provided by Mid Florida Regional MLS 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 MLS. 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 MLS. 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 MLS 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: Thursday, October 23, 2014 at 7:57 PM