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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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$650,000
$2,462/mo
Monthly Payment:
$2,462
Principal & Interest:
$2,408
HOA Dues:
$54
(Based on a 30 year fixed loan at 3.75% with $130,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size1.0acre BuiltN/A On Site123days
Over 1 acre in The Vias! Fantastic Lake Temple lakefront lot available. Located in Tuscany Place, on a quiet cul-de-sac this home site offers gorgeous lake views with grand oaks... more
Over 1 acre in The Vias! Fantastic Lake Temple lakefront lot available. Located in Tuscany Place, on a quiet cul-de-sac this home site offers gorgeous lake views with grand oaks and deeded access to the Winter Park chain-of-lakes. Existing home presents a Designer’s “Dream Challenge”. Featuring over 3,000 SF with four bedrooms and three and one-half baths, the California contemporary inspired interior showcases high ceilings, large windows with great natural light, and beautiful wood beam stairs. Large bonus room across the back of the home is perfect for use as a large office or multi-purpose room overlooking the lake. Oversized backyard leaves plenty of room for a pool, outdoor kitchen, and more! Zoned for A-rated Winter Park schools and just minutes from Park Avenue, the racquet club, Winter Park Golf Course and shops and dining. Move-in, renovate, or build your dream home, the possibilities are endless! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
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$1,509,000
$6,870/mo
Monthly Payment:
$6,870
Principal & Interest:
$5,590
HOA Dues:
$1,280
(Based on a 30 year fixed loan at 3.75% with $301,800 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,291sq ft $659 / sq ft CND
Lot Size13,765sq ft Built2008 On Site123days
This classic style residence invites you in with warm accents and designer lighting. The large, open kitchen with an included wine refrigerator is perfect for entertaining. The... more
This classic style residence invites you in with warm accents and designer lighting. The large, open kitchen with an included wine refrigerator is perfect for entertaining. The french doors that line the walls of the living room create a Manhattan-like ambiance with the charm of Winter Park. The master bedroom is fully equipped with a grand his/her bathroom including a walk-closet efficiently designed and ready for use. This residence exudes a luxury lifestyle with all the qualities of home. less
Listing Provided Courtesy of Taylor & Mathis Orlando
Popularity
$1,544,236
$7,001/mo
Monthly Payment:
$7,001
Principal & Interest:
$5,721
HOA Dues:
$1,280
(Based on a 30 year fixed loan at 3.75% with $308,847 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,450sq ft $630 / sq ft CND
Lot Size13,765sq ft Built2008 On Site123days
The Landmark is the finest, most prestigious condominium residence nestled among the high profile streets of downtown Winter Park steps from Park Avenue. The aesthetically... more
The Landmark is the finest, most prestigious condominium residence nestled among the high profile streets of downtown Winter Park steps from Park Avenue. The aesthetically pleasing and award-winning architectural design presents a European, old world style throughout each detail. This spacious second floor luxury condo has unparalleled views of downtown activity in Winter Park. The kitchen is ready to be adorned with cabinets and personal accents to create a masterpiece for the chef. This residence gives you the opportunity to create a family room, an additional 3rd bedroom, den or even an executive office. It is open, bright and ready to come alive! less
Listing Provided Courtesy of Taylor & Mathis Orlando
Popularity
$1,675,000
$7,485/mo
Monthly Payment:
$7,485
Principal & Interest:
$6,205
HOA Dues:
$1,280
(Based on a 30 year fixed loan at 3.75% with $335,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,143sq ft $782 / sq ft CND
Lot Size13,765sq ft Built2008 On Site126days
Welcome home to an exclusive residence detailing all the amenities of luxurious living. Located in the heart of charming downtown Winter Park, just steps off beautiful Park... more
Welcome home to an exclusive residence detailing all the amenities of luxurious living. Located in the heart of charming downtown Winter Park, just steps off beautiful Park Avenue with its many fine bars, boutiques, shops, fine restaurants, wine rooms and sidewalk cafes.This Penthouse condominium is full of surprises and elegant touches of handcrafted architecture and design. The warm and inviting Chef's kitchen is perfect when entertaining guests as it sits adjacent to a spacious living and dining area. As you sit admiring the views of the illuminating gas fireplace, the glass lined walls display peaceful tree-lined images boasting the ambiance of serenity. The private Master Bedroom is designed with a unique his and her bathroom. A shower dressed in glass is shared by two separate private vanity areas. Not only will you witness the awe-inspiring views from the full length balcony, you have the privilege of the panoramic sights from the private roof-top terrace. The quality and charm is unmistakable in this fully dressed Penthouse Suite. less
Listing Provided Courtesy of Taylor & Mathis Orlando
Popularity
$589,900
$2,218/mo
Monthly Payment:
$2,218
Principal & Interest:
$2,185
HOA Dues:
$33
(Based on a 30 year fixed loan at 3.75% with $117,980 down)
Winter Park, FL 32789
Orange County School District
4bed 2bath 3,092sq ft $191 / sq ft SFR
Lot Size16,281sq ft Built1980 On Site126days
Located on cul de sac in beautiful Waterbridge subdivision next to Windsong easement. Unusually spacious and private backyard with large, open, rectangular, in-ground pool and... more
Located on cul de sac in beautiful Waterbridge subdivision next to Windsong easement. Unusually spacious and private backyard with large, open, rectangular, in-ground pool and large backyard. 9 rooms have pool view. Schools: Brookshire, Glenridge Middle, WP HS. Master BR suite includes study and double walk-in closets. Master bath includes extra vanity/dressing area. Cathedral ceiling in living and family rooms. Ceramic tile in foyer, and family room as well as kitchen / breakfast room. less
Listing Provided Courtesy of The Sheridan Network.com
Popularity
$2,149,000
$7,961/mo
Monthly Payment:
$7,961
Principal & Interest:
$7,961
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $429,800 down)
Winter Park, FL 32789
Orange County School District
4bed 6bath 5,194sq ft $414 / sq ft SFR
Lot Size24,227sq ft Built2009 On Site126days
Huge price reduction. Sellers need to sell quickly. Please bring your offers. Stunning home in an absolutely great location. Impeccable craftsmanship, luxurious comfort, privacy... more
Huge price reduction. Sellers need to sell quickly. Please bring your offers. Stunning home in an absolutely great location. Impeccable craftsmanship, luxurious comfort, privacy and unsurpassed elegancy is what makes this home perfect for a family. This rare find rustic-italian tuscany style home includes/ features a grand entry with a breathtaking view of the lake. Beautiful rounded staircase leading to second floor suites. Gourmet kitchen with two dish washers, professional chef's stove, huge hidden pantry with additional two refrigerators, with beautiful traditional style cabinets and granite counter tops. Loaded with countless details from tray ceiling, niches, hardwood floors, travertine, granite, wood trim, beams, and entertainment centers. Owner suite on the main floor and second master suite both include jacuzzi, built in closets, and a private balcony on the second floor suite. Second floor features family room with built in bar area, and additional laundry room. Numerous elegant architectural details include: 4 private balconies, 2 covered patios with summer-kitchen and gas fireplace, salt water pool/spa, and steam room. Private covered boat dock that includes boat and jet ski lift. Enjoy fantastic panoramic views of ski - lake killarney and breathtaking sunset views from almost every room in your house. Conveniently located to winter park village plaza, park avenue, farmers market, rollins, winter park country club, i-4, downtown orlando. less
Listing Provided Courtesy of Re/max Select
Popularity
$299,900
$1,306/mo
Monthly Payment:
$1,306
Principal & Interest:
$1,111
HOA Dues:
$195
(Based on a 30 year fixed loan at 3.75% with $59,980 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,599sq ft $188 / sq ft TWN
Lot Size2,030sq ft Built2006 On Site126days
Welcome home to this move-in ready, 3 bedroom end unit townhouse in the desirable community of townhomes at harper place in winter park! A light and bright open floor plan that... more
Welcome home to this move-in ready, 3 bedroom end unit townhouse in the desirable community of townhomes at harper place in winter park! A light and bright open floor plan that features gorgeous cherry hardwood throughout the downstairs, a gourmet style eat-in kitchen with granite counter tops, cherry cabinets, stainless appliances with gas range, and built-in wine refrigerator with custom made hutch! Enjoy watching the sunrise from the second story balcony of the master suite or entertaining friends in the evening on your private fenced and tiled patio courtyard. Extras include an attached 2 car garage, crown molding, blinds throughout, indoor laundry, dual sinks and walk-in closet in the master and many more! The community is conveniently located just a short distance from the amazing shops and restaurants of downtown winter park, the florida hospital complex and downtown orlando. Come enjoy low maintenance living and make your appointment today! less
Listing Provided Courtesy of All Real Estate & Investments
Popularity
$530,000
$1,963/mo
Monthly Payment:
$1,963
Principal & Interest:
$1,963
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $106,000 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 2,943sq ft $180 / sq ft SFR
Lot Size9,165sq ft Built1986 On Site126days
The location is incomparable as it is uniquely located directly on the Winter Park golf course. This character home boasts five bedrooms, three and one-half baths, wood burning... more
The location is incomparable as it is uniquely located directly on the Winter Park golf course. This character home boasts five bedrooms, three and one-half baths, wood burning fireplace and two car garage. Downstairs master suite overlooks golf course and has a claw foot bath tub. Upstairs features four bedrooms plus a bonus room. Enjoy watching golfers play from the wrap around porch. Great opportunity to build your dream home or renovate existing home and be one of the only homes on the golf course. This lot is approx 76 X 120 , .21 acres, 9156 square feet. Ask listing agent for more details regarding the adjacent land as it is not part of this parcel. Property currently has a long term tenant and term is flexible although current owner has committed to tenant through June 1, 2016. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$2,400,000
$8,891/mo
Monthly Payment:
$8,891
Principal & Interest:
$8,891
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $480,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 5,706sq ft $421 / sq ft SFR
Lot Size23,958sq ft Built1999 On Site127days
Located on one of Central Florida's most sought after streets---PARK AVE. Timeless classic elegance best describes this beautiful two story brick estate. Built with meticulous... more
Located on one of Central Florida's most sought after streets---PARK AVE. Timeless classic elegance best describes this beautiful two story brick estate. Built with meticulous detail and classic finishes such as hardwood floors, extensive ceiling details, leaded glass, detailed gas fireplaces, and custom built-ins in almost every room. The grand foyer welcomes guests with a graceful sweeping staircase and both formal living and dining rooms. The secluded master suite occupies the left wing of the home on the first floor and boasts a fireplace, luxurious master bath, dressing room, and a surprise hidden coffee bar. The kitchens oversize island, breakfast nook and family room all flow together for casual family time. Large French doors open to the covered lanai featuring a summer kitchen and bar area for entertaining poolside in a very private outdoor setting. Just off the kitchen is a spacious butler's pantry and wine closet. Head down the hallway to another large self-contained suite. This can serve as an in-law suite, billiard room, or executive home office. Upstairs you will find oversized bedrooms with private baths, large walk in closets, and access to the second story open-air balconies. There is a second set of stairs that offers direct access to the kitchen and family room. Bring the cars and toys-- this home has a large motor court with 4-car garages and a private gated side entry. This is a luxury home that will appeal to all generations for years to come. less
Listing Provided Courtesy of Sand Dollar Realty Group Inc
Popularity
$1,035,000
$3,834/mo
Monthly Payment:
$3,834
Principal & Interest:
$3,834
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $207,000 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 3,901sq ft $265 / sq ft SFR
Lot Size11,409sq ft Built2015 On Site127days
Combine a much desired Winter Park neighborhood and Benchmark Building Inc. and you'll find this beautifully constructed Mediterranean-Modern home. Built with attention to... more
Combine a much desired Winter Park neighborhood and Benchmark Building Inc. and you'll find this beautifully constructed Mediterranean-Modern home. Built with attention to detail with the very best quality and craftsmanship to include: travertine and white washed oak wood flooring, Mohawk designer carpeting in bedrooms, Venetian plaster, Smart House System with iPad controls, glass stair railing, solid walnut wooden breakfast bar, quartzite/carerra/travertine countertops, Grohe faucets, custom kitchen with pullout and swivel shelving, hidden pantry, Thermador Gas Appliances, 42" refrigerator, designer lighting throughout, high efficiency AC, Pella windows, two tank-less gas water heaters, fiberglass french doors, and pre wired for video surveillance. Outdoor features a private courtyard with linear fireplace, gas grill, two story lanai/balcony with chisel edge travertine flooring and rear yard is an ideal location for future pool. * Pool rendering and pricing available upon request. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$1,398,800
$5,182/mo
Monthly Payment:
$5,182
Principal & Interest:
$5,182
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $279,760 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,350sq ft $322 / sq ft SFR
Lot Size9,500sq ft Built2015 On Site127days
Within minutes of Park Ave. 5 bedroom, 5 bath, 4,350 sf French New Orleans style at $321/sf! Interiors intended to be transitional and clean with touches of the New Orleans... more
Within minutes of Park Ave. 5 bedroom, 5 bath, 4,350 sf French New Orleans style at $321/sf! Interiors intended to be transitional and clean with touches of the New Orleans style for added whimsy. Guest and Master bedroom downstairs. Master has spacious en suite with large 11x16 walk-in closet! Theater and game room and 2 separate wet bars for entertaining. Stone and wood flooring, granite counters and travertine showers. Kitchen is a chef's dream with upgraded cabinets, soft close doors, in cabinet lighting, and wolf/sub zero type appliances. less
Listing Provided Courtesy of Usrealty.com Llp
Popularity
$1,249,000
$4,627/mo
Monthly Payment:
$4,627
Principal & Interest:
$4,627
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $249,800 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 3,753sq ft $333 / sq ft SFR
Lot Size13,234sq ft Built1991 On Site128days
Stunning 4 bedroom 4 1/2 bath home with a separate study/den that could be a 5th bedroom. This home is in a prime Via location on one of the most desirable streets in Winter... more
Stunning 4 bedroom 4 1/2 bath home with a separate study/den that could be a 5th bedroom. This home is in a prime Via location on one of the most desirable streets in Winter Park. This gorgeous home has been updated with top of the line finishes; Bamboo flooring, hardwood, marble, crown molding, plantation shutters throughout, stainless gas appliances, granite countertops and much more. The private master suite is downstairs on the 1st floor and features a very large walk in closet with organizers and large master bath. Upstairs are 3 additional bedrooms, which one can be another large master suite or bonus room. This home has lots of closets and storage throughout. New gourmet kitchen with gas and large eat in area, and family room all overlooking private fenced yard and beautiful pool with pavers and stone. Separate 2 car detached garage with 1/2 bath and summer kitchen for entertaining. Roof is 2 1/2 years, 3 A/C's (2 new), new tankless hot water heater and pool heater and more. Walk to Winter Park Racquet Club. This is a quality home with Winter Parks A+ Schools. Dommerich Elementary, Maitland Middle, and Winter High School. Come view this home today! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$725,000
$2,686/mo
Monthly Payment:
$2,686
Principal & Interest:
$2,686
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $145,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,555sq ft $284 / sq ft SFR
Lot Size10,999sq ft Built1973 On Site129days
Location is everything! Priced to sell by motivated seller, this 2,555-square-foot home with private, rear-entry 600-square-foot two-car garage presents a rare opportunity to... more
Location is everything! Priced to sell by motivated seller, this 2,555-square-foot home with private, rear-entry 600-square-foot two-car garage presents a rare opportunity to live on a quiet tree-lined brick street in one of Winter Park's most desirable neighborhoods. Located near the museums, shops, and restaurants of downtown Winter Park and Park Avenue, the Winter Park Country Club, the Winter Park Racquet Club, and the popular lakeside Kraft Azalea Gardens, this traditional two-story home has 3 (or 4) bedrooms and 2.5 baths, with formal living and dining rooms, a family room with custom-milled coffered ceiling, and a master bedroom suite with seating area and a large, room-sized walk-in closet with custom-designed and built cabinetry. Additional outstanding features include Wood-mode custom cabinets and granite countertops in the kitchen, a Travertine marble and granite guest bathroom, Sunburst plantation shutters throughout, Pella double-pane low-E windows, deep crown molding in every room, Brazilian hardwood and Saltillo tile flooring, a Diamond Brite in-ground pool complemented by an adjacent large, raised patio with Sundek coating, a private fenced backyard, and professional landscaping complemented by custom lighting and automatic, zoned landscape irrigation/sprinkler system. This home offers an exceptional chance to live in Winter Park’s very special Golden Triangle – come see for yourself! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$63,300
$234/mo
Monthly Payment:
$234
Principal & Interest:
$234
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $12,660 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 1,085sq ft $58 / sq ft CND
Lot Size5,644sq ft Built1974 On Site130days
2 bedroom 1.5 bath unit recently updated with new stainless steel appliances, new carpet, upgraded tile in the baths, a newer AC unit and water heater are just some of the... more
2 bedroom 1.5 bath unit recently updated with new stainless steel appliances, new carpet, upgraded tile in the baths, a newer AC unit and water heater are just some of the features that make this property a great deal for an investor or student. Washer and dryer are also included. Property is walking distance to Full Sail and just a short commute to UCF and Valencia. less
Listing Provided Courtesy of Jr Kroll Realty
Popularity
$600,000
$2,222/mo
Monthly Payment:
$2,222
Principal & Interest:
$2,222
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $120,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size1.3acre BuiltN/A On Site130days
Only 1 lot left - the one next door of equal size has been sold. Lot size left is 1.35 acres. Seller financing an option - Rare opportunity to find 1.35 acres of Olde Florida... more
Only 1 lot left - the one next door of equal size has been sold. Lot size left is 1.35 acres. Seller financing an option - Rare opportunity to find 1.35 acres of Olde Florida charm with 100 ft of lake front on Lake Temple - IN Winter Park city limits. Towering oaks, spanish moss and citrus trees dot the property. Value is in the land but a house and separate studio/guest house on property are ready to put your own touches on, or tear down and build your own lake front dream home - the large mouth bass are literally jumping. This is for the buyer who wants seclusion and privacy - you can't even see most of property or house from Temple Dr. Sought after Winter Park schools - Dommerich Elem, Maitland Middle and Winter Park High. Enjoy the best the metro Orlando area has to offer - Central Florida's gem - Winter Park. Your own piece of old Florida charm. less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity
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: Thursday, September 3, 2015 at 2:06 PM. Properties in listings may have been sold or may no longer be available.