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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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$1,039,000
$3,974/mo
Monthly Payment:
$3,974
Principal & Interest:
$3,849
HOA Dues:
$125
(Based on a 30 year fixed loan at 3.75% with $207,800 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 4,308sq ft $241 / sq ft SFR
Lot Size10,607sq ft Built2002 On Site141days
Fabulous four bedroom home with over 4,300 square feet of spacious living area. Home is located within the only gated community in Winter Park. Designed by award winning... more
Fabulous four bedroom home with over 4,300 square feet of spacious living area. Home is located within the only gated community in Winter Park. Designed by award winning architects, Slocum-Platts, this Showcase home features real oak and travertine floors throughout. Grand foyer, with soaring ceiling and a gorgeous staircase, welcomes you into the home. Spacious living areas, including formal living and dining room, have been tastefully decorated with crown molding, custom built-ins, French doors, and plantation shutters. Stunning kitchen offers a walk-in pantry, wood cabinets, granite countertops, gas cooktop and stainless steel appliances. Downstairs master suite is a retreat in and of itself with a gas fireplace and comfortable lounge with views of the meticulously landscaped yard. Master bath with his and her vanities, jetted tub, and glass shower is perfect for a little relaxation. Three oversized guest rooms upstairs and an adjacent 25x15’ game room is perfect for use a media room, game room, or home office. Brick paved, covered lanai with wood beam ceilings and a second story sun deck take advantage of the home’s outdoor beauty. Located in a highly sought after school district and just minutes from downtown Orlando and Winter Park, this home is truly a must see! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
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$979,000
$3,627/mo
Monthly Payment:
$3,627
Principal & Interest:
$3,627
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $195,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,700sq ft $363 / sq ft SFR
Lot Size10,118sq ft Built1980 On Site141days
California contemporary architecture in the "Via's" of Olde Winter Park. This one of a kind home was completely renovated in 2006. Downstairs Master suite and two bedrooms... more
California contemporary architecture in the "Via's" of Olde Winter Park. This one of a kind home was completely renovated in 2006. Downstairs Master suite and two bedrooms upstairs. Open floor plan for entertaining and huge windows for you to enjoy wonderful views and lots of natural light. Huge gourmet kitchen with exquisite imported granite from Madagascar, wine cooler & stainless appliances. The exterior features private pool, courtyards, balconies! Detached bedroom suite and/or family room plus two-car garage. less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity
$384,900
$1,426/mo
Monthly Payment:
$1,426
Principal & Interest:
$1,426
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $76,980 down)
Winter Park, FL 32792
Golfside Orange County School District
4bed 2bath 2,048sq ft $188 / sq ft SFR
Lot Size12,187sq ft Built1978 On Site141days
Fantastic home completely renovated and remodeled in the much sought after Greenview At Winter Green community of Winter Park. Beautiful oak canopied streets lead to this... more
Fantastic home completely renovated and remodeled in the much sought after Greenview At Winter Green community of Winter Park. Beautiful oak canopied streets lead to this stunning, move-in ready home located on one of the largest lots in the neighborhood. Unique open floor plan with two wood burning fire places, in the living room and in the den. Featuring New enlarged kitchen with all wood cabinets, Crown molding, Granite counter tops, Tiled backsplash, New Whirlpool Stainless Steel Appliances include French door refrigerator, Self cleaning smooth top range, Over the range microwave, Dishwasher, and disposal. New Bathrooms with tall, all wood cabinets, granite counter tops, new faucets and light fixtures. New Architectural shingled roof with 30 year warranty, New plumbing, New floors, New six panel doors, textured ceilings thru out the house, indoor laundry room. Fourth bedroom has French doors and would make a great office. A-rated Winter Park Schools are within walking or biking distance. Stay healthy by walking, biking, or jogging on the Cady Way Trail that runs thru the neighborhood. Includes transferable one year home warranty. Close to all of the great restaurants and shops on Winter Park's famed Park Ave. Also, close to Winter Park Hospital, Rollins College, UCF, and many cultural activities and museums. less
Listing Provided Courtesy of Pozo Real Estate Investments
Popularity N/A
$449,999
$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
Fairview Shores Orange County School District
3bed 3bath 2,768sq ft $163 / sq ft SFR
Lot Size6,755sq ft Built1986 On Site143days
This unrivaled Winter Park Charmer is sure to wow you. From the moment you drive down this private quiet street facing beautiful Lake Killarney. Completely updated from top to... more
This unrivaled Winter Park Charmer is sure to wow you. From the moment you drive down this private quiet street facing beautiful Lake Killarney. Completely updated from top to bottom. Outstanding lake views make you feel like you're on a vacation. Exclusive gated entry 3 bedrooms plus office/study and 3 full baths. Large pool that was just resurfaced 2013. Newer roof 2005, 2 Trane AC units 2009, entire home replumbed 2014, hot water heater 2013. 2 car garage, irrigation system, security system, pavers. All hardwood flooring and tile thru-out. tray ceilings, crown moulding, wainscotting, chair rail. Downstairs has new double pane security glass & hurricane proof glass, and french doors. Back covered porch w/pavers & fenced yard. Utility shed tons of exquisite architectural features such as built in china cabinets, wine closet, butler pantry, wrought iron gates, ceiling beams. Granite in bath and kitchen, stainless appliances, 2 fireplaces, and so much more. Ready for you to move right in today. Prime location just minutes to Florida Hospital, Downtown, Park Avenue and New Trader Joe's. Easy access to I-4. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$850,000
$3,149/mo
Monthly Payment:
$3,149
Principal & Interest:
$3,149
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $170,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,478sq ft $244 / sq ft SFR
Lot Size10,125sq ft Built2003 On Site144days
Reduced!!! Owner financing and lease purchase available!!!!Wonderful traditional home in the heart of winter park. This home features a perfect floor plan, brazilian cherry wood... more
Reduced!!! Owner financing and lease purchase available!!!!Wonderful traditional home in the heart of winter park. This home features a perfect floor plan, brazilian cherry wood floors in the formal living room and dining room travertine,tile extensive crown molding, plantation shutters and 10' ceilings. Gourmet kitchen with state of the art appliances, 48" gas cook tops, granite counter tops large island and wine cooler. Breakfast nook which overlooks screened pool area as well as family room has a gas fireplace for cool evenings and french doors leading to pool area. Master suite has 2 california closets, tray ceilings, french doors, elegant master has a whirl pool tub and vanity mirrors with a built-in tv. Second floor has a master suite also with large dressing room and 2 other large bedrooms. Bonus room is perfect for a game room or movie theater. There is a large covered lanai with pool and pool bath. Great location close to winter park village, walk or ride your bike to park ave. To enjoy the fine and casual restaurants and great boutiques to chose from for shopping. convenient to orlando, best hospitals, and great schools. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$39,900
$382/mo
Monthly Payment:
$382
Principal & Interest:
$147
HOA Dues:
$235
(Based on a 30 year fixed loan at 3.75% with $7,980 down)
Winter Park, FL 32792
Orange County School District
1bed 1bath 756sq ft $53 / sq ft CND
Lot Size8,509sq ft Built1974 On Site144days
This is NOT a Short Sale or REO, quick closing available! This spacious second floor end unit is ready for a new owner. This property is a mere block from Full Sail University... more
This is NOT a Short Sale or REO, quick closing available! This spacious second floor end unit is ready for a new owner. This property is a mere block from Full Sail University and a short commute to the University of Central Florida. UPDATE: Owner just installed washer and dryer hookups in the unit and replaced carpet with hardwood flooring in the bedroom. Also added a built in entertainment center in the living room. Check out the new photos!! Shopping, restaurants, public transportation and major highways are closely located. The community offers a large clubhouse, pool, playground and dual tennis courts. Call about this great investment opportunity today! less
Listing Provided Courtesy of Berger Realty & Investments
Popularity
$2,100,000
$9,445/mo
Monthly Payment:
$9,445
Principal & Interest:
$7,780
HOA Dues:
$1,665
(Based on a 30 year fixed loan at 3.75% with $420,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,839sq ft $547 / sq ft CND
Lot Size27,512sq ft Built2008 On Site145days
Enjoy the convenience of Winter Park living without sacrificing the lifestyle of luxury and comfort that you are accustomed to. Reflecting the classic architecture of Tuscany... more
Enjoy the convenience of Winter Park living without sacrificing the lifestyle of luxury and comfort that you are accustomed to. Reflecting the classic architecture of Tuscany centuries-old Siena, Villa Siena combines Old World design with the modern comforts of estate luxury. Each unit is superbly appointed with fine finishes including stone and hardwood floors, private balconies and Sub-Zero and Wolf appliances. With only four floors, Villa Siena provides you with the privacy of an intimate setting that is rich in amenities including club room with bar, billiards & card lounge, fitness center and rooftop terrace. Villa Siena is located in the heart of Winter Park, walking distance to world class shopping & dining, Rollins College & the Alford Inn. less
Listing Provided Courtesy of Re/max Park Avenue
Popularity
$1,200,000
$5,311/mo
Monthly Payment:
$5,311
Principal & Interest:
$4,445
HOA Dues:
$866
(Based on a 30 year fixed loan at 3.75% with $240,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,290sq ft $524 / sq ft CND
Lot Size1.5acre Built2003 On Site145days
Exclusive lakefront condo located on the shores of Lake Virginia! This stunning residence offers pristine pool and lake views from two private patios and includes a deeded,... more
Exclusive lakefront condo located on the shores of Lake Virginia! This stunning residence offers pristine pool and lake views from two private patios and includes a deeded, on-site boat slip. From the secured, gated entry to the impressive architectural exterior this luxury condo has it all. The property boasts 2,290 square feet of spacious living and elegant appointments. The grand marble foyer will welcome you home and lead you to the formal living/dining rooms with pool and lake views. The generously sized kitchen is thoughtfully designed and features solid wood cabinets, granite counter-tops and stainless steel appliances. The kitchen opens to a second living area that can easily include a less formal dining table. The master bedroom has french doors leading to a second private patio also overlooking the lake. It offers a luxurious master bathroom complete with Jacuzzi tub, separate shower, dual vanities, and a large walk-in closet. Two additional size-able bedrooms and two full bathrooms on the other side of the condo provide that sought after split-plan privacy. This residence is conveyed with a vast and private storage area. Located just steps from Park Avenue, enjoy all that our special city has to offer from the convenience of this maintenance-free, plush residence. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$1,329,000
$4,940/mo
Monthly Payment:
$4,940
Principal & Interest:
$4,923
HOA Dues:
$17
(Based on a 30 year fixed loan at 3.75% with $265,800 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,386sq ft $303 / sq ft SFR
Lot Size13,800sq ft Built2007 On Site145days
This Traditional home located in desired Park Grove steps from Park Avenue is feature rich and loaded with amenities. This warm and inviting home built by Bates Custom Homes in... more
This Traditional home located in desired Park Grove steps from Park Avenue is feature rich and loaded with amenities. This warm and inviting home built by Bates Custom Homes in 2007 features 5 bedrooms, 4.5 baths. The generous Master suite on the main floor leads to a private patio overlooking the pool. The master bath features travertine, dual shower and sinks, jetted tub and a built-in towel warmer. The master suite also has a huge walk in closet with custom shelving and drawers galore. This home features an Epicurean kitchen with an island, breakfast bar, full walk in pantry, built in desk, all leading to the inviting breakfast room overlooking the pool. The downstairs offers the family room a fireplace, separate formal living and dinning rooms, butlers panty/wet bar with ice maker and bar refrigerator. In addition, the first floor features a private guest/mother in law suite with a full bath. Upstairs is a family oasis with a large den/game room surrounded by 4 bedrooms and 2 full baths, convenient laundry chute to downstairs laundry room offering ample cabinets and built-ins including work stations for homework. An outdoor brick patio flows to large pool deck perfect for entertaining, also a deep pool with a diving board, 2 tank less gas water heaters and countless amenities. Park Grove is in a sought after school district with convenient access to anywhere. It’s a fabulous home in a great neighborhood! less
Listing Provided Courtesy of Olde Town Brokers Inc
Popularity
$469,000
$1,737/mo
Monthly Payment:
$1,737
Principal & Interest:
$1,737
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $93,800 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
3bed 4bath 2,154sq ft $218 / sq ft SFR
Lot Size4,928sq ft Built2000 On Site146days
Beautiful and Spacious two story 3 Bedroom, 3 1/2 Bath Townhome in Winter Park with attached 2 Car Garage. NO HOA FEES! Short walk to Park Ave Shopping, Dining, Winter Park... more
Beautiful and Spacious two story 3 Bedroom, 3 1/2 Bath Townhome in Winter Park with attached 2 Car Garage. NO HOA FEES! Short walk to Park Ave Shopping, Dining, Winter Park Farmers Market and Rollins College. This well maintained Townhome features a Great Open Floorplan with 3 Upper Level Bedrooms, all with Ensuite Full Baths. Plenty of closet space with built ins in all Bedrooms. Spacious Master Bedroom with Juliette Balcony and Walk in Closet with more Built ins. Master Bath features dual sinks, jetted Tub and separate large Shower. Gourmet Kitchen with Gas Stove top. Gorgeous hardwood floors throughout the lower level and main living areas. Separate Dining Room, Living Room, and Family Room. French Doors leading to a Spacious Courtyard, perfect for Grilling and Entertaining This one is not to be missed! Enjoy the Winter Park lifestyle! less
Listing Provided Courtesy of Keller Williams Heritage Rlty
Popularity
$299,000
$1,640/mo
Monthly Payment:
$1,640
Principal & Interest:
$1,107
HOA Dues:
$533
(Based on a 30 year fixed loan at 3.75% with $59,800 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 950sq ft $315 / sq ft CND
Lot Size24,593sq ft Built1956 On Site148days
A great opportunity to live on Park Avenue! Make this place your very own - a two bedroom, two bath renovated condo in Park Aire, next to some of the most beautiful landmarks of... more
A great opportunity to live on Park Avenue! Make this place your very own - a two bedroom, two bath renovated condo in Park Aire, next to some of the most beautiful landmarks of downtown Winter Park ~ Casa Feliz, St. Margaret Mary and the Winter Park Country Club! This unit is located on the third floor, has a spacious bedroom with a walk-in closet, large windows overlooking the golf course, and access to a patio/porch area perfect for entertaining. Park Aire is situated in a courtyard style with a lawn area and pool, reserved underground parking and a laundry facility. Prime downtown location, stroll to fabulous Park Avenue shops and restaurants, stop by Casa Feliz for their numerous free weekend concerts, or walk to the clubhouse of the Winter Park Country Club to play a round of golf! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$725,000
$2,740/mo
Monthly Payment:
$2,740
Principal & Interest:
$2,686
HOA Dues:
$54
(Based on a 30 year fixed loan at 3.75% with $145,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,065sq ft $237 / sq ft SFR
Lot Size1.0acre Built1979 On Site148days
A fantastic opportunity to own a 3065 sq. ft. home on a small lakefront in the Vias! This home sits on a quiet cul-de-sac location surrounded by multi-million dollar homes in... more
A fantastic opportunity to own a 3065 sq. ft. home on a small lakefront in the Vias! This home sits on a quiet cul-de-sac location surrounded by multi-million dollar homes in Winter Park. Pure potential in this four bedroom, three and one half bath home! Vaulted ceilings and large windows allow relaxing lake vistas from every room. Split bedrooms with master and additional bedroom down. Large bonus room across the back of the home makes for a large office or playroom overlooking the lake, and open to the family room as well. Nestled in one of the most desirable and private neighborhoods in Winter Park, this home has privacy plus with its expansive yard, lake and cul-de-sac location. Plenty of room for a pool here with over an acre! Low HOA membership just once a year. A-rated Winter Park Schools. In addition to lakefront on Lake Temple, the home also has deeded access to the Winter Park chain of lakes ramp nearby. Remodel or build to suit on this expansive, waterfront acreage. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity N/A
$295,000
$1,368/mo
Monthly Payment:
$1,368
Principal & Interest:
$1,092
HOA Dues:
$276
(Based on a 30 year fixed loan at 3.75% with $59,000 down)
Winter Park, FL 32789
Orange County School District
2bed 3bath 1,214sq ft $243 / sq ft CND
Lot Size3.3acre Built1986 On Site149days
Fantastic opportunity to own a lakefront condo in Winter Park! This charming two bedroom, two and one-half bath unit has over 1,200 square feet of open living space and features... more
Fantastic opportunity to own a lakefront condo in Winter Park! This charming two bedroom, two and one-half bath unit has over 1,200 square feet of open living space and features a large kitchen with room for dining and a living room with wood burning fireplace. Enjoy the lakefront breeze or an evening sunset from your own private screened-in patio. Double master bedrooms each have a full bath and tons of closet space. Killarney Bay is a small, private community on the shores of Lake Killarney. Amenities include exclusive use of the community dock and pool, and a location that can’t be beat! Walk to the Winter Park Village, the new Trader Joe’s plaza, and many other nearby shops and restaurants. Don’t miss the opportunity to see this home or its stunning view! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$1,400,000
$5,186/mo
Monthly Payment:
$5,186
Principal & Interest:
$5,186
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $280,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,703sq ft $298 / sq ft SFR
Lot Size39,102sq ft Built1964 On Site149days
Welcome to Winter Park ski-lake living in a magnificent custom home completely rebuilt by PSG in 2000 and refreshed in 2015. Close to Park Avenue shopping and all the amenities... more
Welcome to Winter Park ski-lake living in a magnificent custom home completely rebuilt by PSG in 2000 and refreshed in 2015. Close to Park Avenue shopping and all the amenities of the 32789 lifestyle, this perfectly presented home is made for family fun, entertaining and enjoying the serenity of Florida's true beauty. With unbounded spaciousness, it offers a boat dock, jet ski garage, secondary bedrooms with walk-in closets and en suite baths and banks of 8' French doors that allow the crystal blues of lake water and warm oranges of sunsets to fill views from bedrooms and living areas. Other unique features include a glamorously-appointed elevator, custom cabinetry at every turn, three walk-in storage rooms (60 sq ft each), and an oversized walk-in kitchen pantry. It's a must-see on a quiet lakeside of re-builds and re-dos. less
Listing Provided Courtesy of Stephen Philip Wood
Popularity
$875,000
$3,241/mo
Monthly Payment:
$3,241
Principal & Interest:
$3,241
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $175,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,641sq ft $240 / sq ft SFR
Lot Size11,260sq ft Built2009 On Site151days
Spectacular pool home in the heart of Winter Park. This traditional home has been graciously appointed and boasts four bedrooms, an office, four and one half baths and a bonus... more
Spectacular pool home in the heart of Winter Park. This traditional home has been graciously appointed and boasts four bedrooms, an office, four and one half baths and a bonus room. Home office w/ full bath and closet could easily be used as a fifth bedroom. A thoughtfully designed floorplan welcomes guests into a spacious foyer and leads them past the formal dining into the gourmet kitchen featuring top-of-the-line stainless steel gas appliances, built-in double ovens, cooking island, gorgeous granite counters, large breakfast bar, copper barn sink and walk in pantry. Off the kitchen is an open, expansive family room,with double sided gas fireplace and two sets of French doors that lead to the screened in, outdoor living area.The downstairs master retreat offers spa bath showcasing a custom built shower with body sprayers, a jetted tub, his and her vanities, and large walk-in closet. The second floor includes three bedrooms, two full baths, and bonus/flex room, large enough for a pool table or use as a theater room with walkout balcony. The outdoor living space has been thoughtfully considered and created to be the ideal entertainment space, complimented by a double-sided fireplace, summer kitchen, and views of the sparkling pool and spa. Additional features include:gorgeous hardwood flooring, extensive crown molding, over-sized corner lot, impeccable landscaping, fenced yard.Seller Motivated! Seller willing to contribute towards buyers closing costs with an acceptable offer closing by July 31, 2015. less
Listing Provided Courtesy of Kelly Price & Company Llc
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: Friday, July 3, 2015 at 4:32 AM