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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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$799,000
$3,181/mo
Monthly Payment:
$3,181
Principal & Interest:
$2,960
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $159,800 down)
Winter Park, FL 32789
Baldwin Park Orange County School District
4bed 4bath 2,853sq ft $280 / sq ft SFR
Lot Size6,297sq ft Built2000 On Site116days
Pristine Windsong home with wonderful details and quality throughout! Enjoy first floor living including master suite and 2 bedrooms. 2nd floor is 4th bedroom/bonus. Renovated... more
Pristine Windsong home with wonderful details and quality throughout! Enjoy first floor living including master suite and 2 bedrooms. 2nd floor is 4th bedroom/bonus. Renovated kitchen with eat-in area and natural gas cooking, 3 way split bedroom plan, gorgeous lanai with pavers and charming space for entertaining. Additional features include wood floors, built-ins, plantation shutters, rear entry 2 car garage, inside utility, 2 new AC units 2013. Enjoy all the great amenities Windsong has to offer! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
Your search results are current and complete. Learn more
$1,485,000
$5,501/mo
Monthly Payment:
$5,501
Principal & Interest:
$5,501
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $297,000 down)
Winter Park, FL 32789
Orange County School District
5bed 8bath 4,832sq ft $307 / sq ft SFR
Lot Size10,514sq ft Built2007 On Site118days
Winter Park Pool Home with Lake Access. Builders own home built with all the modern amenities, exceptional quality and craftsmanship. Move in Ready totally updated. Functional... more
Winter Park Pool Home with Lake Access. Builders own home built with all the modern amenities, exceptional quality and craftsmanship. Move in Ready totally updated. Functional open floor plan has a downstairs Master Suite as well as a 2nd.Bedroom which is perfect for a Nursery, Office or Additional Living Room. The sun filled Great Room has 18' ceilings, four Patio Doors overlooking the sparkling Salt Water Pool & Waterfall. The Formal Dining Room has a 2-sided gas or wood burning fireplace. Gourmet Kitchen equipped with Viking Professional Series Stainless Appliances, Custom Maple Cabinets, Granite Counters, Walk in Pantry and Plantation Blinds throughout. 4 oversized Bedrooms Upstairs have Private Luxury Baths, Walk in Closets with California Closet Systems. A 2nd Family Room perfectly located upstairs by the secondary Bedrooms, great for teenagers so they have own space. Abundance of storage space as well as an extra 600 sf. of heated unfinished space that can easily be finished as a Theatre or Media Room. 2 Laundry Rooms one up & one down, outdoor Security Cameras , Detached Cabana & Pool Bath can be a 6th Bedroom or could be the 3rd. Car Garage. Gorgeous Hardwood, and Travertine Marble Flooring throughout. Convenient Circular Brick Paved Driveway, and Side-Entry 2 or 3 Car Garage with an oversized parking pad. Brick Paved Patio, Salt Water Pool, Covered Lanai and Wrought-Iron Gates, and Outdoor Lighting. Lake Access!!!! less
Listing Provided Courtesy of Westgate Realty
Popularity
$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 Site118days
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
$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 Site118days
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 Site118days
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 Site121days
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 Site121days
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 Site121days
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 Site121days
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 Site121days
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 Site122days
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 Site122days
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 Site122days
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 Site123days
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 Site124days
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
17 18 19 20 21 22 23 24 25 ... 30
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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

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: Saturday, August 29, 2015 at 8:57 PM. Properties in listings may have been sold or may no longer be available.