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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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$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 Site163days
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
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$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 Site163days
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 Site163days
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 Site163days
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
$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 Site163days
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
$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 Site164days
***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 Site167days
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 Site169days
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 Site169days
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
$255,500
$981/mo
Monthly Payment:
$981
Principal & Interest:
$946
HOA Dues:
$35
(Based on a 30 year fixed loan at 3.75% with $51,100 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,806sq ft $141 / sq ft SFR
Lot Size8,983sq ft Built2002 On Site170days
Seller ready to move! That means a great opportunity for you to own & enjoy this spacious & super clean 3bd + office/2ba pool home on cul-de-sac in quiet one street subdivision.... more
Seller ready to move! That means a great opportunity for you to own & enjoy this spacious & super clean 3bd + office/2ba pool home on cul-de-sac in quiet one street subdivision. Located just minutes from shopping, restaurants, full sail, ucf, major roads & more! You will not be disappointed. Act now & be in by the holidays! See it today! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$265,000
$981/mo
Monthly Payment:
$981
Principal & Interest:
$981
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $53,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size15,075sq ft BuiltN/A On Site171days
Vacant Land for sale in beautiful Winter Park, Florida. Build your dream home. This is a rare find. Property has a lake view of Lake Killarney. The property is conveniently... more
Vacant Land for sale in beautiful Winter Park, Florida. Build your dream home. This is a rare find. Property has a lake view of Lake Killarney. The property is conveniently located near I-4 and Lee Rd with easy access to Winter Park Village and the new Ravaudage Development, as well as to the historic Winter Park area. Close to downtown Orlando and all Orlando attractions. Lot Size: 15,074 sq ft/0.35 acre Property has deeded lake privileges. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$4,899,000
$18,150/mo
Monthly Payment:
$18,150
Principal & Interest:
$18,150
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $979,800 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 8,207sq ft $597 / sq ft SFR
Lot Size4.6acre Built2001 On Site172days
This exquisite lakefront gated estate custom built by Charles Clayton in 2001 is situated on an amazing 1.5 acre meticulously manicured lot with 157 ft on the shores of Lake... more
This exquisite lakefront gated estate custom built by Charles Clayton in 2001 is situated on an amazing 1.5 acre meticulously manicured lot with 157 ft on the shores of Lake Maitland of the exclusive Winter Park Chain of Lakes. Spectacular lake views and quality craftsmanship throughout . Downstairs master suite with sitting room and fireplace. Downstairs guest suite with private entrance. Rich mahogany paneled office/library with fireplace. Gourmet kitchen boasts delightful breakfast nook. Fantastic living room with 20 ft ceilings. Cozy family room has a fireplace and walk-in wet bar. Upstairs are three bedroom suites, a soundproof media room with theatre seating and state of the art electronics as well as a large bonus/game room and exercise room. Enjoy stunning sunsets year-round from the large covered lanai with screened solar and gas heated pool , fountain, spa and summer kitchen. Private boat dock and lift make this home perfect for entertaining or family living! The oversized three car garage with separate air conditioned one car garage plus additional storage building will hold your cars, boat, motorcycles and more. Absolutely no detail overlooked. Excellent Winter Park location in the heart of Olde Winter Park . CREATIVE SELLER FINANCING AVAILABLE. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$420,000
$1,556/mo
Monthly Payment:
$1,556
Principal & Interest:
$1,556
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $84,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,153sq ft $195 / sq ft SFR
Lot Size7,720sq ft Built1957 On Site179days
Stunning home located in one of Winter Park’s most desirable neighborhoods! Completely renovated, this captivating, traditional style home features three bedrooms, three... more
Stunning home located in one of Winter Park’s most desirable neighborhoods! Completely renovated, this captivating, traditional style home features three bedrooms, three full baths and an open living and dining area filled with natural light. Character and charm flow throughout the home with meticulously maintained, original hardwood floors. An updated kitchen, featuring solid wood cabinets, granite countertops and a GE appliance package bring a modern touch to the home’s interior. Master suite is generous in size and offers an en suite with oversized soaking tub, separate shower and walk-in closet with custom built-ins. French doors lead to the open patio and allow for a relaxing environment, overlooking the professionally landscaped backyard. Located in the heart of Winter Park, among the mature oak trees, and within walking distance to “A” rated schools, do not miss the opportunity to lives just minutes from Winter Park’s celebrated Park Avenue and call this residence your home! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$2,395,000
$9,094/mo
Monthly Payment:
$9,094
Principal & Interest:
$8,873
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $479,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 6,175sq ft $388 / sq ft SFR
Lot Size20,640sq ft Built2005 On Site182days
Spectacular, private estate in prestigious Windsong! Built in 2005 & featuring five bedrooms, five & two-half baths, this home boasts 6,175 SF of neoclassical inspired interior... more
Spectacular, private estate in prestigious Windsong! Built in 2005 & featuring five bedrooms, five & two-half baths, this home boasts 6,175 SF of neoclassical inspired interior details. Grand two-story entry with stone columns invites guests into formal living & dining areas. Polished marble flooring, high ceilings, & magnificent wrought-iron staircase, combined with Illuminating natural light give this formal living area a palatial feel. Luxury continues throughout the home & into the designer kitchen, where solid wood cabinetry with hand-carved trimming, glass doors, granite countertops, & top-of-the-line chef’s appliances make this kitchen truly inspiring. Second living room off kitchen, has gas fireplace & built-in cabinetry with walk-thru to breakfast area & wet bar. Executive office, with floor to ceiling bookshelves & tray ceiling, maintain a studious environment for the professional in this home. Extravagant, downstairs master suite features lavish, two-story, solid-wood closet. Master bath leaves little to be desired with its jetted tub, large walk-in shower, & double vanities. Upstairs provides the perfect retreat for entertaining. Billiard room, with full bar overlooks downstairs living area, & home theater makes movie night at home a cinematic event. Three of the four upstairs bedrooms are generously sized & offer full bath, walk-in closets, & walk-out balcony. Resort style pool & spa, gazebo with summer kitchen, & covered patio exemplify outdoor living at its finest. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$544,000
$2,015/mo
Monthly Payment:
$2,015
Principal & Interest:
$2,015
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $108,800 down)
Winter Park, FL 32789
Orange County School District
5bed 3bath 3,079sq ft $177 / sq ft SFR
Lot Size9,066sq ft Built1959 On Site183days
Fantastic Family Home! 5 bedrooms, 2 car garage, updated thru out. Beautiful kitchen with stainless steel appliances and granite counter tops. Bathrooms are updated as well.... more
Fantastic Family Home! 5 bedrooms, 2 car garage, updated thru out. Beautiful kitchen with stainless steel appliances and granite counter tops. Bathrooms are updated as well. Crown molding thru out. Wonderful real wood flooring. Master upstairs has an additional space being used as an office. Back yard is private and has plenty of room for a pool if buyer needed. Winter Park Schools! 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
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.

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Data last updated: Thursday, December 18, 2014 at 6:21 AM