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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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$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 Site282days
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
We show you every available listing. Here's how
$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 Site282days
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
$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 Site283days
A Winter Park build to suit close to renowned Park Ave shopping district. We offer this new, 5 bedroom, 5 bath, 1 half bath, 4,350 sf French New Orleans style home at $321/sf!... more
A Winter Park build to suit close to renowned Park Ave shopping district. We offer this new, 5 bedroom, 5 bath, 1 half bath, 4,350 sf French New Orleans style home at $321/sf! Interiors are intended to be transitional, modern and clean with touches of the New Orleans style for added whimsy. Guest and Master bedroom downstairs. Master has spacious en suite with large 11×16 walk-in closet! Theater and game room and 2 separate wet bars for entertaining. Stone and wood flooring, granite counters and travertine showers. Laundry both upstairs and down. Kitchen is a chef’s dream with upgraded cabinets, soft close doors, in cabinet lighting, and wolf/sub zero appliances. Celebrate Mardi gras year round in this luxury estate. less
Listing Provided Courtesy of USREALTY.COM LLP
Popularity
$1,229,999
$4,557/mo
Monthly Payment:
$4,557
Principal & Interest:
$4,557
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $246,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 3,753sq ft $328 / sq ft SFR
Lot Size13,234sq ft Built1991 On Site284days
Open Sat Feb 6, 11am-2pm
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
$499,000
$1,848/mo
Monthly Payment:
$1,848
Principal & Interest:
$1,848
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $99,800 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
6bed 7bath 4,072sq ft $123 / sq ft SFR
Lot Size17,500sq ft Built1935 On Site289days
This home is for sale $40,000 below appraised value! The newly renovated historic home is on a double lot in the beautiful dubsdread hieghts community. Just steps from the the... more
This home is for sale $40,000 below appraised value! The newly renovated historic home is on a double lot in the beautiful dubsdread hieghts community. Just steps from the the historic dubsdread golf course and merely minutes from the art district of winter park and downtown Orlando. This custom home was renovated in 2015 on a lot size of 125 x 140. A detached 652 s/f 1 bed/1 bath home is included in sq. footage. The 2+car garage has also been converted into an 1 bed one bath efficiency as well which is includes in the sq footage calculations. 3 lots on both sides of this home are also for sale. realtor only remarks. Custom designed cathedral ceilings in the Family/Great Room will be the talking point of your guests when they visit your new residence. This home has 2 fireplaces in the main house. The following renovations were completed within the last year; travertine flooring, refinished solid oak hardwood flooring, All new cabinets and granite countertops in the kitchen and bathrooms, New Irrigation system, New paved driveway, New exterior paint, and new interior paint in all rooms. The garage conversion/in law suite features a kitchen and 1 bath. The separate guest house features new cabinets in the kitchen and bathroom, and a fireplace. The main house is around 2900sq ft 4bed 4.1/2 bath. the garage conversion and the guest house are both 1/1 and are each aroun 650sq ft. less
Listing Provided Courtesy of HOMEFIRST REALTY
Popularity
$149,988
$555/mo
Monthly Payment:
$555
Principal & Interest:
$555
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $29,998 down)
Winter Park, FL 32789
N/Asq ft N/A / sq ft LND
Lot Size19,316sq ft BuiltN/A On Site289days
Looking to build your dream home?? Perfect location on this 19,000 sq. ft. corner lot with deeded access to Lake Killarney - one of Winter Park's most private and desirable ski... more
Looking to build your dream home?? Perfect location on this 19,000 sq. ft. corner lot with deeded access to Lake Killarney - one of Winter Park's most private and desirable ski lakes! Beautiful new homes on same street. Conveniently located near I-4, Winter Park Village, in the heart of new development, shopping and dining on Park Ave. *Seller paid over 20k for plans for a 5 bed, 5 bath custom home with 3692 sq. ft. (SEE ATTACHMENTS). less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$1,695,000
$6,279/mo
Monthly Payment:
$6,279
Principal & Interest:
$6,279
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $339,000 down)
Winter Park, FL 32789
Orange County School District
4bed 6bath 3,824sq ft $443 / sq ft SFR
Lot Size9,900sq ft Built2015 On Site292days
Welcome to The Turnberry by Maroon Fine Homes, a beautiful two-story residence. located in the Via's of Winter Park. Designed for indoor and outdoor living, this home offers... more
Welcome to The Turnberry by Maroon Fine Homes, a beautiful two-story residence. located in the Via's of Winter Park. Designed for indoor and outdoor living, this home offers four bedrooms, four full and two half bathrooms and features a unique play/lap pool and cabana. Featuring a warm transitional architectural style and accented by modern interior design, the home offers a blend of hospitality and sophistication. Elegant wide-planked walnut wood floors travel throughout the interior, from the foyer and great room to the kitchen, dining room and home office. Beautiful finishes including smooth stained beams in the great room, along with extensive interior architectural by Niemann Interiors that further enhance this primary living areas. The kitchen offers a walk-in pantry, center island, appliances by Wolf and Sub-Zero and rich, custom all-wood cabinetry. The home's outdoor living area features an expansive pool with mature existing landscaping. The covered lanai features a summer kitchen with stainless steel grill and pool storage. This relaxing retreat is located not far from Park Avenue. less
Listing Provided Courtesy of MAROON REALTY GROUP LLC
Popularity
$1,275,000
$4,723/mo
Monthly Payment:
$4,723
Principal & Interest:
$4,723
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $255,000 down)
Winter Park, FL 32792
Orange County School District
3bed 3bath 2,218sq ft $575 / sq ft SFR
Lot Size1.7acre Built1953 On Site296days
This amazing property is at the end of Lake Spier Drive. It has direct frontage on Lakes Spier and Compton. Located across the street from Lake Baldwin Park and Lake Baldwin and... more
This amazing property is at the end of Lake Spier Drive. It has direct frontage on Lakes Spier and Compton. Located across the street from Lake Baldwin Park and Lake Baldwin and just a short walk to downtown Baldwin Park. Great Winter Park schools. less
Listing Provided Courtesy of BRAD GUSTAFSON, REALTOR
Popularity
$698,000
$2,586/mo
Monthly Payment:
$2,586
Principal & Interest:
$2,586
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $139,600 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 2,442sq ft $286 / sq ft SFR
Lot Size7,380sq ft Built1925 On Site305days
Just completed - february 2016! Showcasing real hardwood floors - this home is a must see! Timeless winter park landmark with a new custom built addition that enhances all of... more
Just completed - february 2016! Showcasing real hardwood floors - this home is a must see! Timeless winter park landmark with a new custom built addition that enhances all of the existing architectural elegance. This perfect mission style home is located on a highly desirable street less than one block from park avenue. Come see the charm that every nook has in this beautiful home. Upgraded features include viking appliances, natural stone master bath, upstairs optional second master suite, hardwood floors and reclaimed chicago style brick driveway with guest spaces. Quick driving distance to the new whole foods market and winter park village. less
Listing Provided Courtesy of PARKLAND INTERNATIONAL REALTY
Popularity
$775,000
$2,871/mo
Monthly Payment:
$2,871
Principal & Interest:
$2,871
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $155,000 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 3,400sq ft $228 / sq ft SFR
Lot Size11,229sq ft Built1965 On Site311days
Beautiful white brick home, completely rebuilt in 2006, situated on corner lot in very desirable Sylvan Lake Shores. Enjoy the neighborhood park and lake across the street and... more
Beautiful white brick home, completely rebuilt in 2006, situated on corner lot in very desirable Sylvan Lake Shores. Enjoy the neighborhood park and lake across the street and historical houses throughout the neighborhood lined with brick streets and old oak trees. Home has four nicely sized bedrooms plus another playroom/bedroom and upstairs suite including gorgeous office retreat with stunning built-ins/wet bar/fridge, bedroom and bathroom retreat plus lots of storage for files or holiday decor. Two spacious master bedrooms. One is on first floor with his and hers closets. Master bath has separate vanities and soaking tub with huge shower. Wide plank hardwood floors, custom moldings and high ceilings throughout. Well-appointed kitchen with granite counters, bead board woodwork, sunroom overlooking saltwater pool and private backyard. Natural gas on the street and gas stove in the home. Living room has wood burning fireplace. Family room boasts custom built-in bookshelves. You will love the close proximity to excellent Winter Park schools, Whole Foods and Park Avenue. Convenient to downtown and Baldwin Park. Great walking neighborhood and adjacent to the North Shore of Windsong. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$1,295,000
$5,861/mo
Monthly Payment:
$5,861
Principal & Interest:
$4,797
HOA Dues:
$1,064
(Based on a 30 year fixed loan at 3.75% with $259,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,714sq ft $477 / sq ft CND
Lot Size1.5acre Built2003 On Site311days
Gorgeous top floor lakefront condo with fantastic views of Lake Virginia and surrounding pool area. 3 bedroom/3.5 baths, 2,714 sq ft, with 12 ft ceilings and a versatile floor... more
Gorgeous top floor lakefront condo with fantastic views of Lake Virginia and surrounding pool area. 3 bedroom/3.5 baths, 2,714 sq ft, with 12 ft ceilings and a versatile floor plan. Glamorous master suite, with water view, has Jacuzzi tub, separate vanities, glass shower and walk-in closet. Gourmet kitchen has granite, custom cabinetry, and upgraded stainless appliances. Spacious great room has adjoining dining room and balcony with a spiral stair case leading down to the pool area. Intimate family room has a alcove which could be used as a eat-in dinette or office. Other amenities include wood and travertine flooring, crown molding, surround sound, and Pella low e double pane doors and windows. Two side-by-side underground parking spaces plus climate-controlled storage. Gated entrance and locked building entrance provide a safe lock and leave lifestyle. Well-maintained grounds with mature landscaping. Luxury lakefront living! Just a short stroll to downtown Winter Park and Rollins College. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$329,900
$1,222/mo
Monthly Payment:
$1,222
Principal & Interest:
$1,222
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $65,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,525sq ft $216 / sq ft SFR
Lot Size6,651sq ft Built1925 On Site312days
Open Sun Feb 7, 1pm-4pm
Welcome to 2600 Winter Park Road. Seller has just UPDATED electrical wires and breaker boxes. Built in 1925, this Spanish Mediterranean home can claim a designation in the... more
Welcome to 2600 Winter Park Road. Seller has just UPDATED electrical wires and breaker boxes. Built in 1925, this Spanish Mediterranean home can claim a designation in the Winter Park Register of Historic places. The original owner since 1957 has lovingly cared for and maintained this 3 bedroom, 2 bath home. The entrance to the home is through a segmented arched opening on the front facing gable. The living room features a wood burning fireplace, a cathedral beamed ceiling, original windows and hardwood floors. From the dining room, French doors, open to a screened side porch. The updated kitchen features recessed lighting, granite counters, Kitchen Aid appliances, new hardwood floors and window treatments. One bathroom has a walk-in shower and the second bathroom has a tub/shower. A free standing two-car garage has been attached to the main body of the house by an open breezeway. The house has many unique architectural features and mature landscaping. Seller will transfer a one year home warranty. Walking distance to the new East End marketplace and Blue Jacket Park. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$275,000
$1,018/mo
Monthly Payment:
$1,018
Principal & Interest:
$1,018
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $55,000 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,393sq ft $197 / sq ft SFR
Lot Size6,847sq ft Built1952 On Site319days
Charming bungalow on the brick "tree streets" of Winter Park! Oversized Master Bedroom overlooking a large fenced in backyard with storage shed. Enjoy both a living room and... more
Charming bungalow on the brick "tree streets" of Winter Park! Oversized Master Bedroom overlooking a large fenced in backyard with storage shed. Enjoy both a living room and great room with a cozy fireplace (garage conversion). Make this your new home or design your dream home in this area of new construction homes! less
Listing Provided Courtesy of ROSE PROPERTIES INC
Popularity
$42,000
$287/mo
Monthly Payment:
$287
Principal & Interest:
$155
HOA Dues:
$132
(Based on a 30 year fixed loan at 3.75% with $8,400 down)
Winter Park, FL 32792
Orange County School District
1bed 1bath 537sq ft $78 / sq ft CND
Lot Size10.1acre Built1974 On Site325days
Studio style condo located in Winter Park, with convienient access to shopping and public transport. Ground floor with patio and tile flooring throughout. Great investment... more
Studio style condo located in Winter Park, with convienient access to shopping and public transport. Ground floor with patio and tile flooring throughout. Great investment property. less
Listing Provided Courtesy of BRENNAN REAL ESTATE GROUP LLC
Popularity
$1,595,000
$5,909/mo
Monthly Payment:
$5,909
Principal & Interest:
$5,909
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $319,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,819sq ft $566 / sq ft CND
Lot Size27,512sq ft Built2008 On Site326days
Fabulous penthouse in the heart of downtown winter park! Steps to park ave with it's world class shopping and dining. This 4th floor corner unit is finished with top quality... more
Fabulous penthouse in the heart of downtown winter park! Steps to park ave with it's world class shopping and dining. This 4th floor corner unit is finished with top quality materials throughout with wolf and subzero appliances, stone and wood flooring. A wet bar with wine cooler and refrigeration drawers. A spacious master suite with 14 foot tray ceiling, an elegant bath and a balcony. The living room features a fireplace and french doors that lead to a balcony with a gas grill and a spiral staircase up to the private roof top terrace with a fireplace and views of the winter park skyline and lake osceola. Villa siena provides you with the privacy of an intimate setting and amenities including a club room with bar, billiards, fitness center and a roof top terrace. Enjoy the downtown lifestyle without giving up the privacy, security and serenity this condo has to offer. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
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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Data last updated: Saturday, February 6, 2016 at 6:08 AM. Properties in listings may have been sold or may no longer be available.