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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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$859,000
$3,182/mo
Monthly Payment:
$3,182
Principal & Interest:
$3,182
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $171,800 down)
Winter Park, FL 32789
Orange County School District
4bed 6bath 3,595sq ft $239 / sq ft SFR
Lot Size14,280sq ft Built1957 On Site134days
Wonderful Home in a tucked-away area in the heart of Winter Park. Main House with 3 Bedrooms 3.5 Baths and Office/Study connected to Master Downstairs.......then GUEST/IN-LAW... more
Wonderful Home in a tucked-away area in the heart of Winter Park. Main House with 3 Bedrooms 3.5 Baths and Office/Study connected to Master Downstairs.......then GUEST/IN-LAW HOUSE w/Living Room, Bedroom, Bath, and Complete Kitchen. All very Spacious Rooms...Gourmet Kitchen opening to Family Room opening to Dining Room...all overlooking the Beautiful Screened Pool. Two Fireplaces...one in the Family Room, one in the Living Room. 2BR 2 Baths upstairs. High end appliances: Sub-Zero Refrigerator, Wolf Gas Range/Convection Oven and Bosch Dishwasher. 3-Car Garage...one with a full Bath. LAKE OSCEOLA ACCESS ACROSS THE STREET. Beautiful Landscaping/Trees. Family Room and Kitchen TVs plus Surround Sound stay. RENOVATED IN 2003 and 2006! Now it can be Yours!! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
Your search results are current and complete. Learn more
$998,000
$3,697/mo
Monthly Payment:
$3,697
Principal & Interest:
$3,697
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $199,600 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 3,767sq ft $265 / sq ft SFR
Lot Size12,059sq ft Built2014 On Site135days
The moment you walk in the front door of an Osprey Custom Home, you're drawn by the innovative, open floor plans. We encourage you to customize your home and put your personal... more
The moment you walk in the front door of an Osprey Custom Home, you're drawn by the innovative, open floor plans. We encourage you to customize your home and put your personal touch on it. Our experience allows us to offer creative suggestions that can significantly enhance the comfort and value of your new home. This home combines the timeless elegance of an estate with the amenities that today's luxury buyers expect. Please see a list of exterior appointments, energy saving features and technology, interior appointments, gourmet kitchen features, and luxury master suite features attached to Matrix. Floor plans and survey are also attached to Matrix. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity N/A
$1,199,900
$4,652/mo
Monthly Payment:
$4,652
Principal & Interest:
$4,445
HOA Dues:
$207
(Based on a 30 year fixed loan at 3.75% with $239,980 down)
Winter Park, FL 32789
Windsong Orange County School District
4bed 5bath 4,259sq ft $282 / sq ft SFR
Lot Size15,059sq ft Built2006 On Site136days
Perfect opportunity to be in an exquisite Custom Built by "Signature Homes" in one of the most prestigious communities, Windsong in the Desirable City of Winter Park with access... more
Perfect opportunity to be in an exquisite Custom Built by "Signature Homes" in one of the most prestigious communities, Windsong in the Desirable City of Winter Park with access to a Chain of Lakes. Mediterranean style, it features a circular driveways, side-entry 3 car garage, luscious landscaping. Grand entrance enhanced with stone columns & a sophisticated solid wood-class door leading into an open foyer & the family-living combo with polished wood floors & French Doors overlooking the relaxing backyard. The high ceilings & the intricately detailed wrought-iron staircase welcomes you into a world of elegance. The half bath is a masterpiece. True European style. Gourmet kitchen with solid wood cabinets, high end granite tops, Wolf & Subzero appliances with warming tray, Bosch dual dishwasher, wine cooler, butler pantry & designer back splash camouflage a large walking pantry. Telescoping sliding doors in the family room give a feel of openness & the wrap around Lanai with summer kitchen are an extension to the house. Granite counters, crown molding and wood shutters throughout. Master bathroom has dual sinks, grandiose mirror, luxurious spa setting, dual-head shower, walking closed with custom built-ins & valet hooks. Guest suite downstairs. Two masters upstairs with large Theater Room with surround sound and HD projector. 94" HD screen & pool table. Energy Star home with Icyenene Foam Insulation. Low utility bills. Gas appliances. Walking distance to the community pool. less
Listing Provided Courtesy of Powerhouse Brokers Int'l
Popularity
$299,800
$1,131/mo
Monthly Payment:
$1,131
Principal & Interest:
$1,110
HOA Dues:
$21
(Based on a 30 year fixed loan at 3.75% with $59,960 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 2,275sq ft $132 / sq ft SFR
Lot Size13,175sq ft Built1988 On Site137days
Huge price reduction for buyer to have their own choice in updating home. This home is on a corner lot,1/4+ acre, with a good size pool and screened pool enclosure with a... more
Huge price reduction for buyer to have their own choice in updating home. This home is on a corner lot,1/4+ acre, with a good size pool and screened pool enclosure with a spacious tiled porch which is great for entertaining or just relaxing with the family. The formal and family rooms have sliding doors that make easy access to the porch and pool. Top rated seminole county schools and close to major shopping, restaurants and 417. Also close to walking and biking trail. Two large ponds with benches and ducks enhance subdivision entrance close to ucf. Don't miss this rare opportunity, come and see this lovely home today ! Send in your offer. less
Listing Provided Courtesy of Cosmopolitan Home Realty Llc
Popularity
$599,500
$2,221/mo
Monthly Payment:
$2,221
Principal & Interest:
$2,221
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $119,900 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,457sq ft $244 / sq ft SFR
Lot Size11,068sq ft Built1963 On Site139days
NEW PRICE! Eclectic mid-century modern home by the design-build team of Sorenson Fletcher -who contributed more to the residential landscape of Winter Park in the 1950s and... more
NEW PRICE! Eclectic mid-century modern home by the design-build team of Sorenson Fletcher -who contributed more to the residential landscape of Winter Park in the 1950s and 1960s than perhaps any builders- reflects a life of clean and uncluttered living featuring a single-story open floor plan with flat roofline, tile fireplace, 2-car carport. It has been updated with the modern conveniences required by 21st century owners while retaining the original "Mad Men" architectural style -all in one of Winter Park's finest brick-street neighborhoods. Immediately upon entering, the terrazzo foyer sets the tone of the house. From there you'll step into the perfect-for-entertaining open floor plan, flooded with natural light. Renovated kitchen with custom cabinets, granite, stainless appliances, wine bar and separate desk/work station. Adjacent laundry/utility room has plenty of room for pantry storage and the convenient half bath. Dining room has floor to ceiling glass on two sides, looking out at the resort-like lush back yard and plunge pool. Four generous bedrooms feature lots of closet space, and two full baths -with an easy solution for creating a third full bath and your true master suite. Dual AC units, energy efficient tankless hot water. Convenient to the YMCA, WP Racquet Club, Whole Foods, Park Ave and SunRail. This home is a 2457 sq ft treasure! less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$1,895,000
$7,241/mo
Monthly Payment:
$7,241
Principal & Interest:
$7,020
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $379,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 5,500sq ft $345 / sq ft SFR
Lot Size15,751sq ft Built2006 On Site140days
Stunning French Provincial, five bedroom estate in prestigious Windsong. This elegant two story home has gorgeous Australian pine floors and crown molding throughout. Welcoming... more
Stunning French Provincial, five bedroom estate in prestigious Windsong. This elegant two story home has gorgeous Australian pine floors and crown molding throughout. Welcoming foyer is open to the formal dining and living room with French doors that overlook the pool and a beautiful fireplace. Gourmet kitchen with custom cabinets, granite counters, integrated refrigerator, double oven, island with gas cooktop and breakfast bar, and built-in desk all overlooking the spacious family room. The large master retreat with French doors overlooking the pool area and a lavish master bath with dual sinks, jetted tub, separate shower and walk-in closet. Also, this home has a first floor guest suite with full bath, and a sophisticated office with custom tasteful built-ins and seating area. There are three large bedrooms, each with it's own spacious closet, a bonus room and open loft all on the second floor. Fabulous fenced backyard features covered lanai, outdoor grill and sparking pool and spa. Professionally landscaped by Keller outdoor and meticulously maintained. Windsong is one of Winter Park's most exclusive neighborhoods and features two community pools, water park and access to the Winter Park chain of lakes. Excellent schools and just minutes to Park Avenue and downtown Orlando! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$209,900
$777/mo
Monthly Payment:
$777
Principal & Interest:
$777
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $41,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,614sq ft $130 / sq ft SFR
Lot Size7,606sq ft Built1979 On Site141days
Don’t miss this amazing opportunity to live in Central Florida’s most sought after city, Winter Park! This 3 Bed—2Bath home is located in the Orwin Manor... more
Don’t miss this amazing opportunity to live in Central Florida’s most sought after city, Winter Park! This 3 Bed—2Bath home is located in the Orwin Manor district of Winter Park, just minutes from the Florida Hospital, Park Ave and Downtown Orlando. This home has been completely remodeled inside and out including a brand new kitchen with stainless steel appliances, new wood floors and carpet throughout the home, new interior paint throughout, a brand new roof, completely re-done landscaping, and new exterior paint. Upon entering the home you are greeted by a small stair case leading to the main floor with an enormous family room, master bedroom, kitchen and dining room. Off of the kitchen and dining room are sliding doors that lead you to the new outside deck, perfect for family BBQ’s and entertaining guest. The first floor of the home contains another large bedroom and full bath with French doors and access to the screened in lanai and back yard. The home is conveniently located near I-4 and in a very good school zone! This home is a must see and will not last long at this price. Call today for more information! less
Listing Provided Courtesy of Fusilier Realty Group
Popularity
$450,000
$1,667/mo
Monthly Payment:
$1,667
Principal & Interest:
$1,667
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $90,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 2,493sq ft $181 / sq ft SFR
Lot Size18,741sq ft Built1916 On Site142days
Winter park lakefront gem!!!!!!!!!!!! Do not miss your opportunity to own this amazing lakefront property in winter park! Minutes from park ave, rollins college and a wonderful... more
Winter park lakefront gem!!!!!!!!!!!! Do not miss your opportunity to own this amazing lakefront property in winter park! Minutes from park ave, rollins college and a wonderful variety of shops and restaurants. This home exhibits a myriad of antique features including original hardwood floors, original trim work, crown molding, doors and best of all a true florida basement. This home also features an updated kitchen, remodeled bathrooms, newer ac system, recently added covered and screened back porch and much more. With a little work, this home could be an antique show stopper!!!!! The basement has all new wood and travertine flooring and set up for a home theater! In addition it features a circular drive and an oversized lakefront lot on lake sylvan! This home is sure to please anyone whom appreciates this early century charm! less
Listing Provided Courtesy of Metro City Realty
Popularity
$550,000
$2,037/mo
Monthly Payment:
$2,037
Principal & Interest:
$2,037
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $110,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 2,118sq ft $260 / sq ft SFR
Lot Size13,904sq ft Built1950 On Site142days
Wonderful Lake Sylvan lakefront home with spectacular views. Step into the entrance foyer and notice the real wood hardwood floors. Home office with window facing the lake. Take... more
Wonderful Lake Sylvan lakefront home with spectacular views. Step into the entrance foyer and notice the real wood hardwood floors. Home office with window facing the lake. Take 3 steps down into the vaulted beamed 13' high ceiling with working fireplace. Very large eat in updated kitchen with lake views, The Florida room is a great place to read the morning paper or rest after work while looking at the light shimmering off the water. Master Suite has a 8' x 8' closet, separate tub and shower. Metal black fenced in rear yard. Circular driveway allows for easy in and out access. Walk to Whole Foods, Outback Steak House or Starbucks. Very private and quiet. less
Listing Provided Courtesy of Winter Park Land Co.
Popularity
$260,000
$963/mo
Monthly Payment:
$963
Principal & Interest:
$963
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $52,000 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,084sq ft $240 / sq ft SFR
Lot Size6,845sq ft Built1952 On Site142days
Fantastic opportunity to own a wonderful piece of property in highly desirable Winter Park. Vintage 1950’s home on a 50x137 lot. Lot provides ample space to build +/-... more
Fantastic opportunity to own a wonderful piece of property in highly desirable Winter Park. Vintage 1950’s home on a 50x137 lot. Lot provides ample space to build +/- 2500 square feet with two stories or +/- 3,000 square feet with three stories. This property has prime location on brick, tree-lined street. Convenient location to Phelps Park, YMCA, Whole Foods, hospital, shops and restaurants. Perfect spot to create the home of your dreams. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity N/A
$199,900
$740/mo
Monthly Payment:
$740
Principal & Interest:
$740
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $39,980 down)
Winter Park, FL 32792
Seminole County School District
4bed 4bath 2,699sq ft $74 / sq ft SFR
Lot Size31,035sq ft Built1972 On Site143days
Corner lot Pool Home! You could not ask for more! Charm and just plenty to create with! Split floor plan with just the right amount of rooms and space that one might just want... more
Corner lot Pool Home! You could not ask for more! Charm and just plenty to create with! Split floor plan with just the right amount of rooms and space that one might just want to call home and then be so proud of owning a nice home in Winter Park! This means... so Close to everything Winter Park has to offer.. Shopping, Fine Dining, Hospitals, Great Schools, Character!! This is a Fannie Mae HomePath property. less
Listing Provided Courtesy of T Real Estate Inc.
Popularity
$399,000
$1,478/mo
Monthly Payment:
$1,478
Principal & Interest:
$1,478
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $79,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,406sq ft $166 / sq ft SFR
Lot Size12,000sq ft Built1965 On Site143days
***price reduced***well kept 4 bdrm 21/2 bath pool home located in beautiful winter park on a conservation area comes with open floor plan, large master bdrm, fla room w/ wood... more
***price reduced***well kept 4 bdrm 21/2 bath pool home located in beautiful winter park on a conservation area comes with open floor plan, large master bdrm, fla room w/ wood burning fireplace, living room/dining combo. A must see!!! less
Listing Provided Courtesy of Weichert Realtors Hallmark Pr
Popularity
$399,999
$1,481/mo
Monthly Payment:
$1,481
Principal & Interest:
$1,481
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $80,000 down)
Winter Park, FL 32789
Orange County School District
2bed 1bath 1,168sq ft $342 / sq ft SFR
Lot Size7,357sq ft Built1946 On Site146days
This quaint 2/1 pool home with cabana is located in the town of Winter Park surrounded by million dollar high end homes. It's in close proximity to all the amenities of Park... more
This quaint 2/1 pool home with cabana is located in the town of Winter Park surrounded by million dollar high end homes. It's in close proximity to all the amenities of Park Avenue. Don't miss out in this great deal! less
Listing Provided Courtesy of Homes In Florida Real Estate
Popularity
$235,000
$870/mo
Monthly Payment:
$870
Principal & Interest:
$870
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $47,000 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,398sq ft $168 / sq ft SFR
Lot Size9,225sq ft Built1961 On Site148days
Winter park golfer's dream home! Excellent location! This 3/2 home features its own pristine 6-hole putting green in the private back yard, mature landscaping and paver... more
Winter park golfer's dream home! Excellent location! This 3/2 home features its own pristine 6-hole putting green in the private back yard, mature landscaping and paver driveway. The living room features an exposed brick wall, beautiful terrazzo flooring throughout. The kitchen features granite counter tops and updated cabinets. Screened porch, great curb appeal with expensive palm trees. Centrally located near winter park retail shopping and restaurants and top rated schools. Call today for your private tour! less
Listing Provided Courtesy of Re/max Town & Country Realty
Popularity
$115,000
$669/mo
Monthly Payment:
$669
Principal & Interest:
$426
HOA Dues:
$243
(Based on a 30 year fixed loan at 3.75% with $23,000 down)
Winter Park, FL 32792
2bed 2bath 1,295sq ft $89 / sq ft CND
Lot Size1,841sq ft Built1981 On Site148days
Location! Location! This charming and well maintained 2/2 condo offers one story spacious living. Its light and bright inside, with many upgrades. This home offers vaulted... more
Location! Location! This charming and well maintained 2/2 condo offers one story spacious living. Its light and bright inside, with many upgrades. This home offers vaulted ceilings, large open great room and a formal dining room with a wet bar. There is an upgraded eat in kitchen including all appliances. The great room has a fireplace and a large sliding glass door that opens to the screened porch. The screened porch provides a cool shady retreat for relaxation an outdoor fun. Its within walking distance to shopping, supermarkets and restaurants. It has a convenient two space dedicated parking pad out front with easy access to major reads and Downtown Winter Park. Cedarwood Village is a well cared for community with a community pool and tennis courts. Don't miss this wonderful home! Owner will consider all offers. less
Listing Provided Courtesy of Watson Realty Corp
Popularity
ZipRealty helps you find current homes for sale in Bay Shore Union Free School District. 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
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.

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Data last updated: Thursday, November 27, 2014 at 1:40 PM