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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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$1,390,000
$5,149/mo
Monthly Payment:
$5,149
Principal & Interest:
$5,149
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $278,000 down)
Winter Park, FL 32789
Orange County School District
6bed 4bath 5,169sq ft $269 / sq ft SFR
Lot Size14,677sq ft Built1991 On Site160days
Mediterranean beauty, within walking distance of the downtown Winter Park area with its charming boutique shops, parks, public golf courses, bistros and gourmet restaurants. You... more
Mediterranean beauty, within walking distance of the downtown Winter Park area with its charming boutique shops, parks, public golf courses, bistros and gourmet restaurants. You are within minutes of public and private schools as well as easy access to I-4, downtown Orlando and area theme parks. The natural light within the home is one of the main reasons the homeowners purchased this home. The living room and kitchen combine to offer the owners a spacious entertaining/family area within the home. The gourmet kitchen features two islands with quartz countertops and top of the line appliances. The home includes two bedrooms/full baths downstairs with 4 bedrooms 2 full bathrooms upstairs. The downstairs in-law quarters/suite has its own separate gated entrance, full bath, sitting area and kitchenette. The upstairs master bedroom has wonderful views overlooking the pool and back yard. The spa-like master bath features a separate glass enclosed shower with digital shower heads, and separate jetted tub. There is lots of wall space to display your artwork. The flooring within the home is a mix of bamboo and travertine tiles all designed for durability and easy maintenance. Renovation upgrades per the seller of $240,000. Come enjoy the community atmosphere Winter Park is all about with its many activities, parades and social life! less
Listing Provided Courtesy of Engel & Voelkers Orlando
Popularity
Your search results are current and complete. Learn more
$615,000
$2,278/mo
Monthly Payment:
$2,278
Principal & Interest:
$2,278
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $123,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,159sq ft $285 / sq ft SFR
Lot Size6,831sq ft Built2015 On Site163days
Custom built 3/3.5 on corner lot in prestigious Winter Park. Travertine flooring throughout the first floor, vaulted ceiling, master and second bedroom upstairs. Third bedroom... more
Custom built 3/3.5 on corner lot in prestigious Winter Park. Travertine flooring throughout the first floor, vaulted ceiling, master and second bedroom upstairs. Third bedroom can be used as den/office. All bedrooms have private bathrooms. Spanish tile roof, covered patio with summer kitchen and over-sized garage. Walking distance to Winter Park village and one mile from Park Ave. Expected completion date mid-January. less
Listing Provided Courtesy of Bhhs Florida Realty
Popularity N/A
$265,900
$985/mo
Monthly Payment:
$985
Principal & Interest:
$985
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $53,180 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,625sq ft $164 / sq ft SFR
Lot Size7,703sq ft Built1957 On Site173days
Charming home conveniently located in Old Winter Park on beautiful brick line street, near Rollins College and Park Ave. Home is tastefully landscaped and has been updated.... more
Charming home conveniently located in Old Winter Park on beautiful brick line street, near Rollins College and Park Ave. Home is tastefully landscaped and has been updated. Brick fireplace in kitchen area, french doors, it is a must see! This is a Fannie Mae HomePath property. All information recorded in the MLS is intended to be accurate but cannot be guaranteed, buyers advised to verify. less
Listing Provided Courtesy of Mickey Hage Inc
Popularity
$3,875,000
$14,356/mo
Monthly Payment:
$14,356
Principal & Interest:
$14,356
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $775,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 5,731sq ft $676 / sq ft SFR
Lot Size30,500sq ft Built1989 On Site175days
Unquestionably one of the most elegant, sophisticated and delightful lakefront homes in all of Winter Park. Situated on Lake Osceola and the Winter Park chain on a beautiful... more
Unquestionably one of the most elegant, sophisticated and delightful lakefront homes in all of Winter Park. Situated on Lake Osceola and the Winter Park chain on a beautiful tree-lined street, only blocks from Park Avenue and all that downtown Winter Park has to offer. Although built in 1989, this home has a historic feel that oozes warmth, luxury and charm. This home has been totally renovated with the very best in quality including enormous brand new gourmet kitchen in 2009, all new AC’s, new Heart of Pine floors throughout, all new LED lighting and much more. Grand entrance foyer, kitchen open to large family room with built-ins and gorgeous details, breakfast room with incredible lake views, formal living room with gas fireplace, paneled library including wine room and separate office. Stunning master suite situated lakefront on the 2nd floor plus additional bedroom suite both open to grand covered balcony. 3rd bedroom suite has separate staircase and 4th bedroom suite is accessible by private elevator to the third floor. Lushly landscaped grounds including private courtyard, dock and covered boathouse with entertaining room. A truly one of a kind home for the most particular buyer. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$1,900,000
$7,039/mo
Monthly Payment:
$7,039
Principal & Interest:
$7,039
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $380,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size37,500sq ft BuiltN/A On Site176days
150 x 250 vacant lot, 37,500 sf. Rarely available "shovel ready" development for 15 townhouses. Approved with variances in place. Total 41,000 sf with a net of 34,000 sf of net... more
150 x 250 vacant lot, 37,500 sf. Rarely available "shovel ready" development for 15 townhouses. Approved with variances in place. Total 41,000 sf with a net of 34,000 sf of net saleable air conditioned space. Each unit has a 2 car attached garage and access to outdoor parking for 7+ extra parking spaces. Four 2 story units and eleven 3 story units. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity N/A
$3,300,000
$12,226/mo
Monthly Payment:
$12,226
Principal & Interest:
$12,226
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $660,000 down)
Winter Park, FL 32789
Orange County School District
4bed 6bath 5,684sq ft $581 / sq ft SFR
Lot Size2.7acre Built1977 On Site184days
Lakefront living at it's finest in a spectacular downtown winter park location! Chain of lakes executive estate with amazing guest quarters nestled in the heart of olde... more
Lakefront living at it's finest in a spectacular downtown winter park location! Chain of lakes executive estate with amazing guest quarters nestled in the heart of olde winter park! Sprawling property offers panoramic views from 130 waterfront feet on picturesque lake maitland! This elegant home (totally renovated in 2001) boasts an outstanding master suite with his & her bathrooms & walk in closets; soaring ceilings in foyer & formal rooms; a smartly appointed gourmet kitchen with stunning cabinets & granite and a cozy breakfast nook; family room with exquisite millwork & built-ins plus a gas fireplace! The 26 x 17 downstairs bonus room perfect for your home office, game room or in-law suite plus an incredible guest home above the 3 car detached garage includes vaulted ceilings, large bedroom/full bath & fully equipped kitchen & laundry room. Stunning back yard oasis includes a fabulous patio for entertaining, perfectly manicured landscaping & stone enhanced waterfront with boat dock. Walk to park avenue from this serene cul-de-sac location! Welcome home! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$145,500
$539/mo
Monthly Payment:
$539
Principal & Interest:
$539
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $29,100 down)
Winter Park, FL 32792
Goldenrod Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size1.8acre BuiltN/A On Site188days
Great opportunity!!! Lake front with 2.31 acres with lots of potential. Call today before it is to late.
Great opportunity!!! Lake front with 2.31 acres with lots of potential. Call today before it is to late. less
Listing Provided Courtesy of Assist 2 Sell All Sellers & Bu
Popularity
$314,900
$1,166/mo
Monthly Payment:
$1,166
Principal & Interest:
$1,166
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $62,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 975sq ft $323 / sq ft SFR
Lot Size15,364sq ft Built1971 On Site189days
Value is in the land! This is an oversized lot...75 x 205 (15,364 sf) located in the highly desirable "Tree Street" neighborhood of Winter Park. Build your dream home here with... more
Value is in the land! This is an oversized lot...75 x 205 (15,364 sf) located in the highly desirable "Tree Street" neighborhood of Winter Park. Build your dream home here with A rated schools and new construction all around. Conveniently located close to the YMCA, Park Avenue Retail District, Rollins College, Farmer's Market, Florida Hospital, and so much more! This lot can support up to a 5,000 sf home with 3 car garage, pool, and wonderful outdoor living spaces. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity N/A
$314,900
$1,166/mo
Monthly Payment:
$1,166
Principal & Interest:
$1,166
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $62,980 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size15,364sq ft BuiltN/A On Site189days
Value is in the land! This is an oversized lot...75 x 205 (15,364 sf) located in the highly desirable "Tree Street" neighborhood of Winter Park. Build your dream home here with... more
Value is in the land! This is an oversized lot...75 x 205 (15,364 sf) located in the highly desirable "Tree Street" neighborhood of Winter Park. Build your dream home here with A rated schools and new construction all around. Conveniently located close to the YMCA, Park Avenue Retail District, Rollins College, Farmer's Market, Florida Hospital, and so much more! This lot can support up to a 5,000 sf home with 3 car garage, pool, and wonderful outdoor living spaces. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity N/A
$800,000
$2,963/mo
Monthly Payment:
$2,963
Principal & Interest:
$2,963
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $160,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size19,059sq ft BuiltN/A On Site195days
Big 150'x130 (approx) building lot (s), serene lake view setting, viewed from the front porch of your new custom home. 15 new homes under construction within 1/2 mile of this... more
Big 150'x130 (approx) building lot (s), serene lake view setting, viewed from the front porch of your new custom home. 15 new homes under construction within 1/2 mile of this location, up to $1.5M. Approved Winter Park City lot split into two 75x130 (approx) lots. See attachment for approval letter. City of Winter Park Building Codes apply. Value is in the land for one large or two separate building lots. Winter Park City maintained Lake Wilbar. less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity N/A
$2,495,000
$9,243/mo
Monthly Payment:
$9,243
Principal & Interest:
$9,243
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $499,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 6,285sq ft $397 / sq ft SFR
Lot Size32,129sq ft Built2011 On Site196days
Magnificent estate home & unique oversized property in the heart of the Via's... premier location on triple lot (3/4 acre) on quiet street... This home was custom built in 2011... more
Magnificent estate home & unique oversized property in the heart of the Via's... premier location on triple lot (3/4 acre) on quiet street... This home was custom built in 2011 with Hal George at Parkland Homes, top quality craftsmanship & exquisite trim / moldings thru-out, bright-open floor plan, high detailed ceilings, generous room sizes, designer lighting, lots of great windows & french doors... Fabulous 1st floor master retreat with lavish bath along with his & her baths/dressing areas... Wonderful huge gourmet island kitchen with commercial appliances & extensive cabinetry, elegant "club room" with full bar & paneled walls, large beautiful formal dining & living rooms with windows/french doors both sides, and a library downstairs... Upstairs includes 4 bedroom suites, game room & bonus room... The outdoor living is nothing short of spectacular with tremendous grounds, expansive covered lanai (invisible remote retractable screens), classic pool area & walled in private yard... Enjoy the Winter Park Racquet Club, tennis courts, & access to Lake Maitland "chain of lakes" next door... A perfect entertaining home & property!! 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 32792
Orange County School District
3bed 2bath 1,592sq ft $166 / sq ft SFR
Lot Size9,542sq ft Built1965 On Site196days
Winter Park Pines Beautiful home with multiple upgrades including newer roof, AC, stucco, gutters, electrical, paint. Tiled, sprinkler well and timer, fenced backyard, screened... more
Winter Park Pines Beautiful home with multiple upgrades including newer roof, AC, stucco, gutters, electrical, paint. Tiled, sprinkler well and timer, fenced backyard, screened porch, back deck and on a corner Lot. New Windows and Updated Baths. Mature Oak Trees and landscaping. A - Rated Winter Park Schools!! less
Listing Provided Courtesy of Florida Home Realty & Invest
Popularity
$1,050,000
$3,890/mo
Monthly Payment:
$3,890
Principal & Interest:
$3,890
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $210,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,265sq ft $322 / sq ft SFR
Lot Size8,583sq ft Built2015 On Site198days
Stunning Custom Contemporary home that will exceed your client's expectations! This gorgeous home will have the master, study and second bedroom all on the first floor.... more
Stunning Custom Contemporary home that will exceed your client's expectations! This gorgeous home will have the master, study and second bedroom all on the first floor. The spacious open concept downstairs living, dining and eat-in kitchen boasts picturesque views of the luxurious resort style swimming pool viewed through the floor to ceiling panoramic sliding glass doors. The living room will also have a sleek, modern, flush mount fireplace to further enhance the luxury of this design. The study will boast a modern sliding barn door and the entry will have an IMPRESSIVE open riser cantilever stair system that will appear to be floating. The first floor master suite offers a private en suite master bath that boasts a "wet room" shower and stand alone tub, as well, as a private outdoor space with an additional shower. It also includes a stackable washer and dryer for convenience. The second floor has two additional bedrooms, a loft area, and a full laundry for servicing the upstairs living. This architect has made exceptional use of light via oversized windows throughout. The exquisite exterior will boast a Stacked Stone accent, exterior wood ceilings, a paver driveway, walk ways and lanai and a ten year warranty exterior paint system. This will be a must see for the most discerning clients!!! less
Listing Provided Courtesy of La Rosa Realty, Llc
Popularity N/A
$65,280
$391/mo
Monthly Payment:
$391
Principal & Interest:
$241
HOA Dues:
$150
(Based on a 30 year fixed loan at 3.75% with $13,056 down)
Winter Park, FL 32792
Seminole County School District
3bed 3bath 1,652sq ft $40 / sq ft CND
Lot Size1,894sq ft Built1984 On Site198days
This property is bank owned. It is sold in “as-is” condition without repairs or warranty. Buyer is responsible for verifying all information contained in this... more
This property is bank owned. It is sold in “as-is” condition without repairs or warranty. Buyer is responsible for verifying all information contained in this listing. less
Listing Provided Courtesy of Realhome Svc & Solutions Inc
Popularity
$349,900
$1,296/mo
Monthly Payment:
$1,296
Principal & Interest:
$1,296
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $69,980 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,935sq ft $181 / sq ft TWN
Lot Size4,775sq ft Built2002 On Site201days
Centrally located in the HEART of Winter Park on a brick-paved street, welcome to stress free living with NO HOA fees! The Mediterranean inspired townhome sits in a quiet... more
Centrally located in the HEART of Winter Park on a brick-paved street, welcome to stress free living with NO HOA fees! The Mediterranean inspired townhome sits in a quiet neighborhood overlooking a well-groomed park, complete with a tranquil pond and a fountain. Recent updates include NEW interior paint, NEW landscape, 4 NEW windows (12/2014), NEW gas hot water heater (2013), and refinished/screened wood floors (12/2014). The Kitchen features a gas stove with a Jen-Air grill, granite counters, and solid wood cabinets with abundance of storage. The breakfast bar opens to a large living room with a 35' ceiling. A separate office area with build-in computer desk, book shelves & storage is off the kitchen. A separate Dining room is off the open Living room, complete with marble-trimmed gas fireplace & custom built bookshelves. Upstairs includes all 3 bedrooms with bright guest bath. The grand master suite features a 12-jet therapeutic bathtub, separate shower , double sinks and a large walk-in closet. The townhome is "smart home" prewired for surround sound, security & an intercom to front door. A central vacuum & available Rainsoft water system make for more quality living. This townhome is TURN KEY ready for you. 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 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: Tuesday, May 26, 2015 at 1:41 PM