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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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$2,950,000
$10,929/mo
Monthly Payment:
$10,929
Principal & Interest:
$10,929
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $590,000 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 5,409sq ft $545 / sq ft SFR
Lot Size33,479sq ft Built1930 On Site153days
One of the original Winter Park Spanish Mediterranean estate homes built in 1930 to the Sinclair Oil family and noted in Winter Park history. This home has been renovated within... more
One of the original Winter Park Spanish Mediterranean estate homes built in 1930 to the Sinclair Oil family and noted in Winter Park history. This home has been renovated within its original design, authentic to every detail. Situated on Lake Osceola and part of the Winter Park chain of lakes it cannot be matched. Inside you will notice cypress woodwork, original tile, plaster walls, and all the details you would expect. Large rooms with expansive lake views including a large Master Suite downstairs. Upstairs four additional bedrooms all with privacy and views of the lake as well. Kitchen and bathrooms all renovated with today's modern requirements including a whole house generator system. Large yard with a large swimming pool and dock for your enjoyment of Lake Osceola. Call today for your private showing. less
Listing Provided Courtesy of Bhhs Florida Realty
Popularity
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$163,500
$605/mo
Monthly Payment:
$605
Principal & Interest:
$605
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $32,700 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
4bed 2bath 1,778sq ft $92 / sq ft SFR
Lot Size10,315sq ft Built1972 On Site153days
You can't go wrong with purchasing this 4 bedroom, 2 bath pool home in Wrenwood Heights. Needs some updating but has some great potential. This home features separate formal... more
You can't go wrong with purchasing this 4 bedroom, 2 bath pool home in Wrenwood Heights. Needs some updating but has some great potential. This home features separate formal living and dining rooms, a combination kitchen and family room with wood-burning stone front fireplace, a nicely finished florida room and a lot of space for the family! less
Listing Provided Courtesy of Metro Brokers Realty
Popularity
$599,000
$2,219/mo
Monthly Payment:
$2,219
Principal & Interest:
$2,219
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $119,800 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 1bath 1,092sq ft $549 / sq ft SFR
Lot Size21,003sq ft Built1960 On Site155days
Total of 6 lots already assembled with development potential in Winter Park. Future rezoning from R2 may allow mixed use opportunity. 1516 Minnesota is 3 lots with 150FF x... more
Total of 6 lots already assembled with development potential in Winter Park. Future rezoning from R2 may allow mixed use opportunity. 1516 Minnesota is 3 lots with 150FF x 140'deep with a 3/1 home providing $1000/mo income, 12mo lease started 4/01/14. Only being sold together with 1518 Minnesota Ave MLS# O5308267 also 3 lots with 150FF x 140'deep with a 3/2 home providing $1150/mo income,12month lease started 5/01/14 plus 1/1cottage providing $650/mo income. Purchase this 300x140 (.96Ac) property with $2800/mo income today, hold for appreciation or future higher density development opportunity. less
Listing Provided Courtesy of Re/max 200 Realty
Popularity N/A
$599,000
$2,219/mo
Monthly Payment:
$2,219
Principal & Interest:
$2,219
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $119,800 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
4bed 3bath 1,701sq ft $352 / sq ft SFR
Lot Size20,863sq ft Built1953 On Site155days
Total of 6 lots already assembled with development potential in Winter Park. Future rezoning from R2 may allow mixed use opportunity. 1518 Minnesota is 3 lots with 150FF x... more
Total of 6 lots already assembled with development potential in Winter Park. Future rezoning from R2 may allow mixed use opportunity. 1518 Minnesota is 3 lots with 150FF x 140'deep with a 3/2 home providing $1150/mo income,12month lease started 5/01/14 + 1/1cottage providing $650/mo income. Only being sold together with 1516 Minnesota Ave MLS#O5308266 also 3 lots with 150FF x 140'deep with a 3/1 home providing $1000/mo income, 12mo lease started 4/01/14. Purchase this 300x140 (.96Ac) property with $2800/mo income today, hold for appreciation or future higher density development opportunity. less
Listing Provided Courtesy of Re/max 200 Realty
Popularity N/A
$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 4bath 3,634sq ft $269 / sq ft SFR
Lot Size9,774sq ft Built2014 On Site157days
Perfect family home located on a quiet tree lined cul-de-sac in the heart of Winter Park. Spacious living areas include a formal living room, dining room, and a large eat in... more
Perfect family home located on a quiet tree lined cul-de-sac in the heart of Winter Park. Spacious living areas include a formal living room, dining room, and a large eat in kitchen open to the family that is perfect for entertaining. French doors from the family room lead to a secluded and private backyard with professional landscaping. This desirable floor-plan includes a well-appointed master suite downstairs with generous closets and his and hers vanities. Upstairs there are 3 additional bedrooms plus a large bonus area that can be used as a home office, playroom or additional storage. less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$849,000
$3,145/mo
Monthly Payment:
$3,145
Principal & Interest:
$3,145
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $169,800 down)
Winter Park, FL 32789
Orange County School District
4bed 6bath 3,595sq ft $236 / sq ft SFR
Lot Size14,280sq ft Built1957 On Site158days
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
$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 Site159days
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
$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 Site160days
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 Site161days
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
$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 Site164days
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
$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 32789
Orange County School District
3bed 2bath 1,614sq ft $124 / sq ft SFR
Lot Size7,606sq ft Built1979 On Site165days
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 Site166days
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 Site166days
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
$185,900
$688/mo
Monthly Payment:
$688
Principal & Interest:
$688
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $37,180 down)
Winter Park, FL 32792
Orange County School District
4bed 2bath 1,673sq ft $111 / sq ft SFR
Lot Size10,740sq ft Built1958 On Site166days
Back on market, entertaining offers from 185,900 to 199,900. Just look at this beautiful 4 bedroom 2 bath home with over 1657 sf, located in winter park estates. This home is... more
Back on market, entertaining offers from 185,900 to 199,900. Just look at this beautiful 4 bedroom 2 bath home with over 1657 sf, located in winter park estates. This home is just amazing and beautiful and has been completely renovated and updated to 2014. Home offers new ceramic tile, new berber carpet in bedrooms, new bathrooms, new kitchen, newly installed custom granite with stainless steel sinks, new stainless steel appliances, new kitchen,new bathrooms and new central air/ and much more. This is not a short sale, or bank owned and can close in less than 30 days. seller will contribute towards closing costs. less
Listing Provided Courtesy of Robert Michael & Company Inc.
Popularity
$309,000
$1,144/mo
Monthly Payment:
$1,144
Principal & Interest:
$1,144
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $61,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,283sq ft $241 / sq ft SFR
Lot Size7,193sq ft Built1955 On Site166days
Wonderful Mid-Century 1950's bungalow with a beautifully landscaped front yard nestled on a quaint Winter Park street. Recently improved with new engineered wood floors... more
Wonderful Mid-Century 1950's bungalow with a beautifully landscaped front yard nestled on a quaint Winter Park street. Recently improved with new engineered wood floors throughout, an open kitchen with stainless steel appliances and granite counters, newer windows and remodeled baths ~ all updated in the past 5 years along with the roof. Brand new A/C system with new ductwork is one year old. Great split floor plan including a formal dining room with a built-in buffet and a spacious master suite with separate closets and private bath. Enjoy the charming brick paver patio overlooking the fenced backyard with storage shed (grandfathered-in by the city). Backyard has room for a pool! Great location close to A+ schools, the Winter Park Hospital, Whole Foods and more! Ride your bike to Park Avenue or Rollins College! less
Listing Provided Courtesy of Not Available
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
Content provided and owned by Coldwell Banker Residential Real Estate.
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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.

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 MLS and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited.

Copyright 2014 Mid Florida Regional MLS. All rights reserved.

Data last updated: Saturday, December 20, 2014 at 9:20 PM