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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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$2,485,000
$9,206/mo
Monthly Payment:
$9,206
Principal & Interest:
$9,206
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $497,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,826sq ft $515 / sq ft SFR
Lot Size14,584sq ft Built1959 On Site28days
Pre-Construction. This "Centerpiece of Park Avenue" will be a 6553sf estate that sets the new precedent for Modern Montecito. Thoughtfully designed for gracious living by Winter... more
Pre-Construction. This "Centerpiece of Park Avenue" will be a 6553sf estate that sets the new precedent for Modern Montecito. Thoughtfully designed for gracious living by Winter Park’s award-winning architect Slocum & Platts with builder Feely Custom Homes. The understated elegance is everywhere. The sense of arrival begins along 180' of Park Ave frontage. natural gas lanterns invite you through a 6' wide metal gate leading into a 22' high foyer, welcoming you to an open designed residence with 12' ceilings, double sided fireplace, seamless views of the lanai, pool and water fall through the expansive folding doors. A perfect blend of indoor-outdoor living. The open floor plan flows from the living areas into a professional Sub Zero/Wolf Kitchen and a bar with a 150 bottle electric wine cellar designed to entertain or partition off for catering with hidden custom pocket doors. The open plan leads into a library and an expansive master suite, a private dressing room with 5-sided mirror, a large walk-in closet and a spa-quality bathroom in Calcutta Gold marble throughout. The Pool and Spa are accompanied by an outdoor trellised dining room and summer kitchen with shell/limestone pavers. Features: 4 private suites, 3 car garage with a circular drive, security system, professionally organized closets, Jeld-Wen windows & doors, barrel tile roof, designer detailed ceilings with wood beams, two gas fireplaces and an extensive use of high-end materials. Truly one of the finest opportunities in Central Florida. less
Listing Provided Courtesy of Parkland International Realty
Popularity
Your search results are current and complete. Learn more
$149,999
$555/mo
Monthly Payment:
$555
Principal & Interest:
$555
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $30,000 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
3bed 2bath 1,532sq ft $98 / sq ft SFR
Lot Size10,469sq ft Built1972 On Site28days
Not a short sale! Not bank owned! Traditional sale! Owners can close immediately! Investor/handyman special! Winter Park! 3bedroom 2 bath split plan home with separate... more
Not a short sale! Not bank owned! Traditional sale! Owners can close immediately! Investor/handyman special! Winter Park! 3bedroom 2 bath split plan home with separate living area and family room with fireplace. One car garage huge back yard with towering oak trees. New roof 2010. House needs updating. Retail 180k/185k+ less
Listing Provided Courtesy of Sand Dollar Realty Group Inc
Popularity
$264,900
$981/mo
Monthly Payment:
$981
Principal & Interest:
$981
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $52,980 down)
Winter Park, FL 32792
Golfside Orange County School District
4bed 3bath 1,920sq ft $138 / sq ft SFR
Lot Size10,788sq ft Built1978 On Site28days
Don't miss your chance to own a one-of-a-kind 4 bedroom 3 bathroom home in the desirable Winter Park Pines neighborhood. Unique interior features include vaulted ceilings,... more
Don't miss your chance to own a one-of-a-kind 4 bedroom 3 bathroom home in the desirable Winter Park Pines neighborhood. Unique interior features include vaulted ceilings, double-sided fireplace, multiple skylights, and garden tub in the master bath. There is a screened in porch off the master suite that overlooks a courtyard with koi pond. The courtyard separates the main house from an in-law suite. The house is across from the Winter Park Golf Course, close to Cady Way Trail and in an excellent school district with no Homeowner's Association. Buyer's may qualify for the HomePath Ready Buyer Program. See attachments for more information. This is a Fannie Mae Homepath property. ** THIS PROPERTY HAS MULTIPLE OFFERS. HIGHEST AND BEST DUE BY Aug 13, 2015 BY NOON! ** less
Listing Provided Courtesy of Smith Realty Inc
Popularity
$525,000
$1,962/mo
Monthly Payment:
$1,962
Principal & Interest:
$1,945
HOA Dues:
$17
(Based on a 30 year fixed loan at 3.75% with $105,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,982sq ft $176 / sq ft SFR
Lot Size12,022sq ft Built1974 On Site28days
Fantastic four bedroom, three bath home in Winter Park’s desirable Quail Hollow community. Zoned for great schools; Audubon Elementary, Glenridge Middle, and Winter Park... more
Fantastic four bedroom, three bath home in Winter Park’s desirable Quail Hollow community. Zoned for great schools; Audubon Elementary, Glenridge Middle, and Winter Park High. Formal living and dining rooms flow seamlessly into the home’s bright and comfortable Sunroom. Wood-burning, brick mantled fireplace in the Family room is warm and inviting. Master bedroom is generously sized and offers tranquil views of the home’s resort styled pool and outdoor living area, complimented by Chicago brick pavers. Numerous updates throughout the home, including new granite countertops in the kitchen, crown molding, and fresh paint. Absolutely charming home and a must see! Easy to show so call today! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$227,500
$842/mo
Monthly Payment:
$842
Principal & Interest:
$842
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $45,500 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 2bath 1,224sq ft $186 / sq ft SFR
Lot Size6,502sq ft Built1925 On Site29days
Very cute 3/2 over 1,200 sq ft cozy home in the Winter Park/College Park area. Refurbished wood floors, tile, new paint inside and deck, wood burning fireplace, french doors,... more
Very cute 3/2 over 1,200 sq ft cozy home in the Winter Park/College Park area. Refurbished wood floors, tile, new paint inside and deck, wood burning fireplace, french doors, large lot with plenty of storage, large carport and fenced. A must see to appreciate. Close to golf club, I-4, and Downtown Orlando & Winter Park. Sold AS-IS. New buyer to verify room sizes and all appliances sold as-is, no warranty that they work. less
Listing Provided Courtesy of Centergate Realty Llc
Popularity
$1,025,000
$3,922/mo
Monthly Payment:
$3,922
Principal & Interest:
$3,797
HOA Dues:
$125
(Based on a 30 year fixed loan at 3.75% with $205,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 4,308sq ft $238 / sq ft SFR
Lot Size10,607sq ft Built2002 On Site29days
A gorgeous home in Winter Park's only gated community! This elegant home boasts exquisite features throughout - a dramatic entry with travertine and marble detail flooring with... more
A gorgeous home in Winter Park's only gated community! This elegant home boasts exquisite features throughout - a dramatic entry with travertine and marble detail flooring with a view to the formal living room, beautiful hardwood floors in all bedrooms and living areas, surround sound, plantation shutters, crown molding, high ceilings and 2 custom gas fireplaces. The open kitchen features an island with prep sink, granite counters, a natural gas cooktop, KitchenAid fridge, large closet pantry, a kitchen bar, desk and breakfast nook. It overlooks a fabulous family room with a fireplace and French doors that open to the lanai. From the kitchen there's a wine room and butler's pantry that lead to a formal dining room. The grand master suite has a vaulted ceiling, fireplace, 2 large walk-in closets and sitting area. The luxurious bath has travertine flooring, spa tub, walk-in shower, large water closet and dual sinks with an extra vanity, all with granite counters. The elegant curved staircase with custom wrought iron railing leads you upstairs to a landing area and 3 more bedrooms, 2 bathrooms and large bonus room - it has a large closet and is suitable as a game room, media room or work space. There are 2 balconies off the bedrooms. Downstairs, the covered lanai overlooks a lush back garden. On a secluded cul-de-sac, there's just 11 homes in Winter Park Place. Easy walking distance to restaurants and shops. Great WP schools, Fla. Hosp., Lake Highland Prep and upscale Park Ave. nearby! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$435,000
$1,611/mo
Monthly Payment:
$1,611
Principal & Interest:
$1,611
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $87,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,257sq ft $346 / sq ft SFR
Lot Size7,000sq ft Built1940 On Site29days
Rollins college area: 1940’s winter park home located in the historical district. 1000 foot walk to rollins down the brick lined street. 3 bed 2 bath, large living room... more
Rollins college area: 1940’s winter park home located in the historical district. 1000 foot walk to rollins down the brick lined street. 3 bed 2 bath, large living room with gas fireplace and formal dining room. Master bath with separate shower, claw foot tub and pedestal sink. Hard wood flooring in main living areas and ceramic tile in kitchen and inside laundry room. Beautiful custom gourmet kitchen with preparation island and commercial grade stainless steel appliances throughout. Dinette area within the kitchen opens to wood deck which overlooks the beautifully landscaped private back yard and outside utility shed / work shop. Conveniently located within 5 minutes to park ave. 30 minutes to downtown orlando and international airports. less
Listing Provided Courtesy of Bhhsthe Property Place
Popularity
$525,000
$1,970/mo
Monthly Payment:
$1,970
Principal & Interest:
$1,945
HOA Dues:
$25
(Based on a 30 year fixed loan at 3.75% with $105,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,393sq ft $219 / sq ft SFR
Lot Size17,506sq ft Built1997 On Site29days
Must see 4/3 in Winter Park's Lake Knowles Neighborhood. This beautiful home has an open floor plan, with separate den and formal dining room. The kitchen will not disappoint... more
Must see 4/3 in Winter Park's Lake Knowles Neighborhood. This beautiful home has an open floor plan, with separate den and formal dining room. The kitchen will not disappoint with its sleek appliances and sparkling granite counter tops! This home has many green features that will help keep the utilities low. Irrigation system draws from the properties well (a rarity in Winter Park) Don't miss out on this immaculate Winter Park home. Call for an appointment today. less
Listing Provided Courtesy of Alicia Spears Realty
Popularity
$795,000
$2,945/mo
Monthly Payment:
$2,945
Principal & Interest:
$2,945
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $159,000 down)
Winter Park, FL 32789
Orange County School District
4bed 2bath 3,402sq ft $234 / sq ft SFR
Lot Size29,111sq ft Built1941 On Site29days
Prime olde Winter Park location near Lake Sue… Build your dream home on this almost 30,000 sq.ft. corner lot on one of Winter Park’s most beautiful brick streets.... more
Prime olde Winter Park location near Lake Sue… Build your dream home on this almost 30,000 sq.ft. corner lot on one of Winter Park’s most beautiful brick streets. This lot is apprx. 150 x 200 and only one house off of Lake Sue so there is potential for lake views from a newly designed home… This gorgeous property is built up from the streets so you can enjoy an elevated setting. Although no value is placed on the existing house/structure sitting on property, the kitchen in the house was completely new 4 years ago with quality cabinets and granite. Some of the cabinets and countertops could be reused. A beautiful pool was installed in 1999 at the back of the lot. Lots this large do not come along very often in Winter Park so don’t miss this great opportunity! Convenient location to hospitals, Lake Highland Prep, downtown Orlando, Rollins College, and Park Avenue. Winter Park “A” rated schools… less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$795,000
$2,945/mo
Monthly Payment:
$2,945
Principal & Interest:
$2,945
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $159,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size29,111sq ft BuiltN/A On Site29days
Prime olde Winter Park location near Lake Sue… Build your dream home on this almost 30,000 sq.ft. corner lot on one of Winter Park’s most beautiful brick streets.... more
Prime olde Winter Park location near Lake Sue… Build your dream home on this almost 30,000 sq.ft. corner lot on one of Winter Park’s most beautiful brick streets. This lot is apprx. 150 x 200 and only one house off of Lake Sue so there is potential for lake views from a newly designed home… This gorgeous property is built up from the streets so you can enjoy an elevated setting. Although no value is placed on the existing house/structure sitting on property, the kitchen in the house was completely new 4 years ago with quality cabinets and granite. Some of the cabinets and countertops could be reused. A beautiful pool was installed in 1999 at the back of the lot. Lots this large do not come along very often in Winter Park so don’t miss this great opportunity! Convenient location to hospitals, Lake Highland Prep, downtown Orlando, Rollins College, and Park Avenue. Winter Park “A” rated schools… less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$1,499,900
$5,557/mo
Monthly Payment:
$5,557
Principal & Interest:
$5,557
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $299,980 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,085sq ft $367 / sq ft SFR
Lot Size11,998sq ft Built2016 On Site29days
Pre construction! This magnificent british west indies estate home awaits your final touches. A soaring 2 story foyer greets you with views of the pool as you enter this very... more
Pre construction! This magnificent british west indies estate home awaits your final touches. A soaring 2 story foyer greets you with views of the pool as you enter this very special home. The large, open kitchen features thermador appliances and a huge island with seating for 6 that overlooks the great room. There are beautiful coffered ceilings in the dining room which is large enough to hold a table for 12! The private master retreat is located on the first floor and has dual closets, a large shower, a freestanding tub and separate vanities. There is second bedroom adjacent to the master that could be used as a study, nursery or guest suite. Upstairs, there are three large en suite bedrooms with a loft in the center that leads to a stunning covered balcony for more entertaining possibilities. This home also has numerous energy features including spray foam isolation, a standing seam metal roof, tank less hot water heaters, and smart home technology pre wired to run the lighting, security and hvac systems at the touch of your smart phone or tablet. This home is located on a lovely brick street in one of the most sought after neighborhoods in winter park with "a" rated schools and proximity to everything winter park has to offer. Call today for plans and specs and a personal preview of this fantastic residence. less
Listing Provided Courtesy of Coledev Real Estate Llc
Popularity
$565,000
$2,093/mo
Monthly Payment:
$2,093
Principal & Interest:
$2,093
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $113,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,435sq ft $164 / sq ft SFR
Lot Size21,000sq ft Built1926 On Site30days
Residential Compound! Winter Park historic Home with separate Office suite and private Apartment to the rear of the property, great for rental income or multi-family. This... more
Residential Compound! Winter Park historic Home with separate Office suite and private Apartment to the rear of the property, great for rental income or multi-family. This Spanish villa style Main house was built in 1926 and is 2 bed/ 2 bath. Enter into history… large Living room with original hand cut wood floors, chic crystal accent lighting and gas fireplace. Delightful Dining room with designer wall sconces and chandelier. Large remodeled Kitchen is light and bright and opens to the Family room – perfect for family gatherings. Also on main level is a secondary Bedroom with a full bath. Master Bedroom is on the second floor and features built-in wardrobe cabinets and a fireplace. The Master features a romantic window lined turret, perfect for sitting area or desk. The separate Office is attached to the Guest House and has a full bath, tall ceilings, French doors & accent lighting. The complete Guest House in the rear has Mexican tile floors and is a 2 bed/ 2 bath with living room, dining area, full kitchen and own laundry. All sits on a triple lot measuring 140 x 150 with circular drive, 3 car carport & plenty of room for additional parking. Plenty of room to expand, add a pool and/or a 3 car garage. The east third of the property is like a park with zoysia grass and is completely fenced & gated. Great multi-family situation. This property has been a wonderful rental investment property and can be yours too! Easy access to I-4, both downtown Winter Park & downtown Orlando and to Florida Hospital. less
Listing Provided Courtesy of Parkland International Realty
Popularity
$210,000
$778/mo
Monthly Payment:
$778
Principal & Interest:
$778
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $42,000 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,669sq ft $126 / sq ft SFR
Lot Size6,955sq ft Built1956 On Site30days
Short Sale. Welcome to one of the best citied to live in, Winter Park. Close to great schools, Park Ave, Rollins College and many entertainment such as Disney, Universal,... more
Short Sale. Welcome to one of the best citied to live in, Winter Park. Close to great schools, Park Ave, Rollins College and many entertainment such as Disney, Universal, SeaWorld and more. Winter Park is a heavy desirable area to live in, take a look at this property asap. When you walk in thru your front door, your amazed at the living room style and ceramic tiles. Walking thru the living room and to the left are two bedrooms with a bathroom. On the other side of the living room you reach the gourmet kitchen. Have fun entertaining and preparing great meals to eat, and enjoy you separate dining area next to the kitchen. Fit a beautiful dining table and enjoy your thanksgiving diner you've always wanted with your loved ones. Your bonus room can be changed to a 4th bedroom by adding a closet or keep it as is and use as an office, play area, game room, or anything you've always wanted to have in your home. Walking pass the kitchen you come to a separate loft, relax or set up another area of you choosing such as a game room, play area. Next to the loft you have your washer and dryer hook up area, and your master bedroom. The master bedroom show with ample space for any size furniture, go king if you want to, and you own private walk in closet and separate bathroom. This is a great property to own, and with your love it will become a home. less
Listing Provided Courtesy of Exit Realty Central
Popularity
$949,000
$3,515/mo
Monthly Payment:
$3,515
Principal & Interest:
$3,515
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $189,800 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,266sq ft $291 / sq ft SFR
Lot Size9,221sq ft Built1999 On Site30days
Don’t miss this beautiful New Orleans style home in the “heart of Winter Park”. This 5bdrm/5bath pool home boasts quality throughout. From the minute you... more
Don’t miss this beautiful New Orleans style home in the “heart of Winter Park”. This 5bdrm/5bath pool home boasts quality throughout. From the minute you pull into the driveway, you will feel at home. The expansive front porches are perfect for morning coffee or for visiting with neighbors. This lovely home features beautiful tongue and groove hardwood floors, crown molding, plantation shutters, downstairs office with bath (could also be a bedroom), downstairs master suite. The kitchen and family room combination are perfect for entertaining. The family room is warm and inviting with a brick gas or wood burning fireplace. The ceilings and windows in the family expand to the 2nd floor so extra light shines through. You will love cooking in the lovely kitchen featuring a gas cooktop, double ovens, warming drawer, newer refrigerator and dishwasher, granite countertops and a fabulous breakfast nook overlooking the pool and backyard. If you need a private guest suite, bonus room or a separate office, the flex space above the garage is the perfect place. The pool area is an oasis featuring a saltwater pool, extensive brick patio, full bath and beautiful landscaping. Many upgrades include brand new landscaping, updated kitchen countertops, replaced two bathroom vanities, newer pool equipment and refinished floors. Walking distance to Phelps Park and Park Avenue. Winter Park “A” Schools. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$665,000
$2,463/mo
Monthly Payment:
$2,463
Principal & Interest:
$2,463
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $133,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,780sq ft $239 / sq ft SFR
Lot Size7,494sq ft Built2008 On Site32days
Beautiful, newer 4/2.5 on wonderful brick­lined Winter Park Street. Modern clean lines interior and open floor plan with exceptional stacked marble wall in the... more
Beautiful, newer 4/2.5 on wonderful brick­lined Winter Park Street. Modern clean lines interior and open floor plan with exceptional stacked marble wall in the foyer. Kitchen flows into bright living room with vaulted ceilings, stacked marble Eco­Smart gas fireplace, custom built­ins and custom window treatments. Downstairs Master Suite with custom walk­in closet, beautiful bath with dual sinks, jetted tub and large glass walk­in shower. Three additional bedrooms upstairs with ample closet space, Jack­and­Jill bath, plus bright bonus room/loft. Granite countertops and wood floors throughout, newly installed hand­scraped Spanish wood on second floor, crown molding, tankless hot water heater, double pane windows, downstairs laundry room, stainless steel appliances, detached 2­car garage, meticulously landscaped back yard with organic garden beds and much more. Enjoy contemporary living near Lakemont YMCA, Phelps Park, top rated Winter Park Schools, and Whole Foods. Priced right, so call today for your private showing! less
Listing Provided Courtesy of Murphy Properties Llc
Popularity
3 4 5 6 7 8 9 10 11 ... 16 26
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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.

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Data last updated: Monday, August 31, 2015 at 8:40 PM. Properties in listings may have been sold or may no longer be available.