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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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$2,195,000
$8,132/mo
Monthly Payment:
$8,132
Principal & Interest:
$8,132
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $439,000 down)
Winter Park, FL 32789
Orange County School District
4bed 6bath 6,242sq ft $352 / sq ft SFR
Lot Size18,258sq ft Built2013 On Site127days
Meticulously constructed 4 Bedroom 5 full & 1 half bath 6242 square foot "NEW ORLEANS' style pool home is situated on a beautiful oversized lot on a quiet street just steps away... more
Meticulously constructed 4 Bedroom 5 full & 1 half bath 6242 square foot "NEW ORLEANS' style pool home is situated on a beautiful oversized lot on a quiet street just steps away from Lake Maitland. First floor Master Suite w/ fireplace, kitchenette w/ Thermador refrigerator, dishwasher & sink, huge walk in closet & separate laundry room. Master bath has separate vanities, a soaking tub, large walk in shower & fireplace. Gourmet kitchen w/ top of the line commercial style stainless steel appliances, custom cabinetry, granite and marble counter tops & walk in pantry. Billiard/Game room has a fireplace, wet bar w/ wine refrigerator, Thermador refrigerator/freezer & dishwasher. Additional amenities include: Bevolo light fixtures, antique Chinese elm reclaimed wood floors, fabulous ceiling details throughout, extensive custom millwork & built ins, Windsor double insulated energy efficient windows, 2 covered porches & 2 covered balconies, 3 gas fireplaces, ICF (insulated concrete form) construction, Baldwin Estate hardware, Kohler plumbing fixtures, Elevator & 3 laundry rooms. This amazing home is loaded w/ upgrades & extras. Great attention has been paid to the architectural detail & style and should be viewed in person to truly appreciate the quality throughout. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
We show you every available listing. Here's how
$975,000
$3,612/mo
Monthly Payment:
$3,612
Principal & Interest:
$3,612
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $195,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,194sq ft $232 / sq ft SFR
Lot Size12,276sq ft Built1930 On Site127days
Three homes for the price of one!! In downtown Winter Park, near Rollins College, this meticulously renovated home has 2 rental/guest apartments. The light, bright & open main... more
Three homes for the price of one!! In downtown Winter Park, near Rollins College, this meticulously renovated home has 2 rental/guest apartments. The light, bright & open main home has 3 bedrooms, 3 bathrooms, 3,170 SF, beautiful wood floors, a formal living room with brick fireplace, dining room, office, sun room. The spacious kitchen, ideal for entertaining, is open to the family room. It features a large eating island with exotic counter tops, a breakfast bar, stainless steel appliances, double ovens, a wet bar, under cabinet lighting and glass cabinets. Upstairs, the Master Suite has an impressive dressing room complete with chandelier and built-in closets. The Master bathroom has double sinks and a walk-in shower. The large second bedroom, has wood floors and a sun room/sitting area. The private lush backyard features tropical landscaping and Gazebo with Hot Tub. The separate Guest house has two apartments, each with 1 Bedroom & 1 bath, sunny porches, and kitchens with gas stoves plus a 1 car garage. The upstairs apartment is currently leased from month to month. This exceptional residence combines a modern flair with period character. Walk to Park Ave, fine shopping & dining, Rollins College, WP Library and the Alfond Inn. less
Listing Provided Courtesy of Winter Park Land Co.
Popularity
$1,150,000
$4,260/mo
Monthly Payment:
$4,260
Principal & Interest:
$4,260
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $230,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,619sq ft $318 / sq ft SFR
Lot Size10,200sq ft Built2015 On Site129days
Hurry in for this brand new traditional french style home from david weekley. Come enjoy this spacious 2 story home in the heart of winter park. This beautifully designed and... more
Hurry in for this brand new traditional french style home from david weekley. Come enjoy this spacious 2 story home in the heart of winter park. This beautifully designed and appointed home has plenty of space with its 5 bedrooms, 4.5 baths, study, bonus room, covered lanai and plenty of storage space. It also boasts the newest david weekley "energy saver" construction science that used double pane/low-e ii vinyl windows, seer 14 a/c system, r-38 blown fiberglass insulation and many other energy-saving features. You will enjoy living among such timeless and elegant upgrades as distressed hardwood flooring that extends throughout the main living spaces and into the owners retreat; full overlay, glazed and raised panel cabinets with crown moulding and beveled knobs in the kitchen and bathrooms and electrical pre-wiring for wall mounted interior electronics. This home is destined to truly enhance the lives of its future owners. Our energy saver homes offer homebuyers the best in energy-efficiency and are backed by our program's heating and cooling energy usage guarantee. These homes are friendlier to you, the environment and your pocketbook! less
Listing Provided Courtesy of Weekley Homes Realty Company
Popularity
$424,000
$1,570/mo
Monthly Payment:
$1,570
Principal & Interest:
$1,570
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $84,800 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size9,747sq ft BuiltN/A On Site132days
Build your dream home on this one-of-a-kind lot in sought after Sylvan Lakes Shore in Winter Park. A quintessential tree-lined street near Windsong and a short stroll to Lake... more
Build your dream home on this one-of-a-kind lot in sought after Sylvan Lakes Shore in Winter Park. A quintessential tree-lined street near Windsong and a short stroll to Lake Mizell. Beautiful custom gate and wrought iron fence with brick pillars surrounds the property. Just minutes from great Winter Park amenities such as Park Avenue shopping and dining district, Rollins College, Winter Park YMCA and Interlachen Country Club. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$324,000
$1,200/mo
Monthly Payment:
$1,200
Principal & Interest:
$1,200
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $64,800 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 3bath 1,906sq ft $170 / sq ft SFR
Lot Size7,000sq ft Built2007 On Site133days
Are you looking for easy downtown/florida hospital access? Avoid the i4 tear up with one of 32789 college park's pristine homes. Be to work in less than 10 mins. This 2007 build... more
Are you looking for easy downtown/florida hospital access? Avoid the i4 tear up with one of 32789 college park's pristine homes. Be to work in less than 10 mins. This 2007 build 3 bedroom 2 ½ bathroom home is ideally located in the highly sought after area of dubsdread heights. This mediterranean style executive home offers beautiful finishes from top to bottom. You will immediately notice the red oak hardwood floors that flow through the formal combination living and dining rooms. Continuing through the home you are greeted by a large combination family room and gourmet kitchen. This chef’s dream offers travertine tile, granite counter tops, sleek stainless steel appliances, recessed lighting, crown molding, and a convenient pass thru to the dining room – perfect when entertaining your guests! The family room is light and bright and offers french doors allowing direct access to the spacious fenced in backyard, detached 2 car garage and custom paver driveway offering plenty of additional parking space. The second floor owners retreat is truly a gem offering french doors to a private outdoor balcony, an en-suite bath with a custom tiled shower, soaking tub and granite counters. Additional features of this home include 2 additional spacious bedrooms, a second full bathroom and a main floor powder room. Located just minutes to the charming community of college park offering unique cafes and quaint shops, this home is zoned for *a* rated schools. Come and see all this unique executive home has to offer! less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$264,990
$981/mo
Monthly Payment:
$981
Principal & Interest:
$981
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $52,998 down)
Winter Park, FL 32792
Seminole County School District
4bed 4bath 2,058sq ft $129 / sq ft SFR
Lot Size21,123sq ft Built2003 On Site133days
Location ! Beautiful former model home in Winter Park with no rear neighbors . This home has many great features including a Master bath with double sinks and separate tub and... more
Location ! Beautiful former model home in Winter Park with no rear neighbors . This home has many great features including a Master bath with double sinks and separate tub and shower. Located in the top rated school system . less
Listing Provided Courtesy of Century 21 Carioti
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
Fairview Shores Orange County School District
3bed 3bath 2,427sq ft $361 / sq ft SFR
Lot Size21,852sq ft Built1986 On Site133days
Lake front property in Winter Park doesn't come up For Sale very often and when it does it doesn't stay very long. Well here's your chance!! This 1/2 acre gated and fenced... more
Lake front property in Winter Park doesn't come up For Sale very often and when it does it doesn't stay very long. Well here's your chance!! This 1/2 acre gated and fenced property on pristine Lake Killarney has just become available. Do Not Wait. As soon as you walk through the front door the lakefront panorama comes into view and you immediately begin to unwind from the stress of the day. As you continue on into the home you come into the Family room which boasts vaulted ceilings and brick wood burning fireplace. Just the ticket to take the chill off of those cool winter evenings. Just beyond the fireplace and through the French doors lead you to a 34' screened porch, a perfect place to end the day while gazing out at the water. The 785 sqft garage has lots of room for toys and extra storage. All this and last but not least is Location, Location, Location. less
Listing Provided Courtesy of Weichert Realtors Hallmark Pro
Popularity
$1,975,000
$7,717/mo
Monthly Payment:
$7,717
Principal & Interest:
$7,317
HOA Dues:
$400
(Based on a 30 year fixed loan at 3.75% with $395,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,988sq ft $495 / sq ft TWN
Lot Size1,551sq ft Built2003 On Site134days
This sophisticated Park Avenue townhome is located in the heart of Winter Park. Walk down the Avenue to fabulous restaurants, Central Park, The Farmers’ Market & charming... more
This sophisticated Park Avenue townhome is located in the heart of Winter Park. Walk down the Avenue to fabulous restaurants, Central Park, The Farmers’ Market & charming boutiques! The foyer is inviting w/ marble floors & a spectacular staircase. The first floor features 2 bedrooms w/ in-suite baths, the main laundry room & a spacious 2 car garage. Take the elevator up to the main living floor that features distressed pecan wood floors, a lovely living room w/ built-in media center & hidden TV cabinet. The large dining room accommodates a table for 12. Kitchen has a gorgeous center island w/ zebra wood counter, glass front subzero refrigerator, 2 subzero freezer drawers, subzero wine refrigerator, DCS 6 burner gas range w/ double ovens, custom Morrison wood cabinets w/ travertine counters, slate w/ wood inlay design flooring & a cozy sitting area. Enjoy the screened in back balcony w/ summer kitchen. 3rd Floor features a huge family room w/ built-in media center & wet bar. The master bath has 2 vanity areas, 2 walk-in closets, garden tub, large shower, travertine flooring, marble counter tops & plenty of storage. Additional amenities include: 10 foot ceilings and built-in surround sound throughout, plantation shutters, double pane Pella windows & doors, 3 balconies, bay windows, alarm system w/ security cameras & amazing views less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$478,900
$1,774/mo
Monthly Payment:
$1,774
Principal & Interest:
$1,774
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $95,780 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,044sq ft $234 / sq ft SFR
Lot Size7,000sq ft Built1950 On Site135days
Newly Remodeled Orwin Manor Home. This home has been remodeled from the ground up. The home has great curb appeal and is ready for the new owner. The home contains 3 bedrooms... more
Newly Remodeled Orwin Manor Home. This home has been remodeled from the ground up. The home has great curb appeal and is ready for the new owner. The home contains 3 bedrooms and 3 full baths which is a rare find in the Orwin Manor area. It has all new cabinets and granite counter tops. New A/C ,new windows ,new wood flooring and tile. The master bedroom has a HUGE closet and shower and a separate tub. Great location and in the 32789 zip code. The backyard is fenced in and has all new landscaping and irrigation. Come look and you will not be disappointed ! Everything is new and done with quality craftmanship! less
Listing Provided Courtesy of Costello Realty & Development
Popularity
$299,999
$1,387/mo
Monthly Payment:
$1,387
Principal & Interest:
$1,111
HOA Dues:
$276
(Based on a 30 year fixed loan at 3.75% with $60,000 down)
Winter Park, FL 32789
Orange County School District
2bed 3bath 1,214sq ft $247 / sq ft CND
Lot SizeN/Asq ft Built1986 On Site136days
Completely Remodeled and Open Floorplan Overlooking Lake Killarney in Winter Park! - Large and inviting with water views from Kitchen, Breakfast Nook, Master Bedroom and Living... more
Completely Remodeled and Open Floorplan Overlooking Lake Killarney in Winter Park! - Large and inviting with water views from Kitchen, Breakfast Nook, Master Bedroom and Living Room with fireplace - Private screened in balcony for your morning coffee or evening sunset. Double master bedrooms with full baths and large closets. Private amenities give you exclusive use of the gorgeous community pool, dock and beach where you can park your boat. Next to the new Trader Joes, Winter Park Village and minutes from Park Avenue. less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$525,000
$1,945/mo
Monthly Payment:
$1,945
Principal & Interest:
$1,945
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $105,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 2,112sq ft $249 / sq ft SFR
Lot Size9,745sq ft Built1987 On Site139days
Reduced to sell!!! Seller is motivated, bring all offers!!! Beautifully remodeled home in the heart of winter park. Just steps from rollins college and conveniently located to... more
Reduced to sell!!! Seller is motivated, bring all offers!!! Beautifully remodeled home in the heart of winter park. Just steps from rollins college and conveniently located to fabulous park ave. Step inside the gated entry through the double front doors to a spacious great room with vaulted ceilings and a fireplace with marble surround. The kitchen has tons of cabinet space with marble countertops a huge island and space for a large dining table. Master bedroom has french doors that open to the fenced in back yard with a sparkling pool and wood deck. Master bathroom boasts dual sinks and an oversized shower with a rainfall shower head and glass doors as well as huge walk in closet. On the other side of the house sits 2 additional bedrooms and a nicely appointed guest bath. Nothing has been spared in making this home like new, schedule a showing today! less
Listing Provided Courtesy of National Real Estate Llc
Popularity
$995,000
$4,423/mo
Monthly Payment:
$4,423
Principal & Interest:
$3,686
HOA Dues:
$737
(Based on a 30 year fixed loan at 3.75% with $199,000 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,700sq ft $585 / sq ft CND
Lot Size27,512sq ft Built2007 On Site139days
This is one of six floor plans available to purchase at Villa Siena. Villa Siena is located in the Historic Downtown section of Winter Park, Florida. Walk to Park Avenue shops,... more
This is one of six floor plans available to purchase at Villa Siena. Villa Siena is located in the Historic Downtown section of Winter Park, Florida. Walk to Park Avenue shops, restaurants and parks. In this premier 2nd floor location the floor plan takes advantage of a calm garden view. Unit has gas Wolf cooking and Sub-Zero refrigeration. Top quality materials are used throughout. Common areas include expansive club room which includes a large bar area, pool area and party room. The building and unit are fabulous and bright. Attention to detail can be seen throughout the property. less
Listing Provided Courtesy of Re/max Park Avenue
Popularity
$240,000
$889/mo
Monthly Payment:
$889
Principal & Interest:
$889
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $48,000 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
4bed 2bath 1,605sq ft $150 / sq ft SFR
Lot Size9,690sq ft Built1956 On Site140days
Very well maintained four bedroom two bath Florida home on a corner lot! This single-family home features tile floors throughout, spacious living/dining rooms & kitchen with... more
Very well maintained four bedroom two bath Florida home on a corner lot! This single-family home features tile floors throughout, spacious living/dining rooms & kitchen with granite countertops. Family room opens up to the expansive, fenced-in back yard complete with a large screened-in pool & patio. New roof 2014. New septic system installed May 2010. Pool pump replaced 2011. A must see! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$600,000
$2,357/mo
Monthly Payment:
$2,357
Principal & Interest:
$2,222
HOA Dues:
$135
(Based on a 30 year fixed loan at 3.75% with $120,000 down)
Winter Park, FL 32792
6bed 5bath 4,700sq ft $128 / sq ft SFR
Lot Size9,000sq ft Built2015 On Site140days
Brand new energy efficient home ready NOW! The Wimberley features a spacious kitchen with granite countertops, large walk in pantry, tons of cabinet space and cozy breakfast... more
Brand new energy efficient home ready NOW! The Wimberley features a spacious kitchen with granite countertops, large walk in pantry, tons of cabinet space and cozy breakfast nook all open to a huge family room ideal for family and friends to gather. The formal Living room and Dining room give you plenty of room for entertaining. The secluded Master suite has an enormous walk in closet and luxurious spa like bath with soothing tub, separate shower and dual vanities. All additional bedrooms are roomy and have walk in closets for added storage. Have family fun night in the massive Game room or enjoy a movie in the media room, which can be converted to a home theater. Enjoy outdoor living on the back lanai. Photo of model home of this same plan, options and upgrades will vary to subject home. Lakeside is a beautiful gated community with waterfront home sites, boat dock and lake located close to Seminole County parks. Known for our energy efficient features, our homes help you live a healthier and quieter lifestyle while saving you thousands of dollars on your utility bills. less
Listing Provided Courtesy of Meritage Homes Of Fl Realty
Popularity
$1,125,000
$5,034/mo
Monthly Payment:
$5,034
Principal & Interest:
$4,168
HOA Dues:
$866
(Based on a 30 year fixed loan at 3.75% with $225,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,290sq ft $491 / sq ft CND
Lot Size1.5acre Built2003 On Site141days
Winter park’s crème de la crème! This exquisite three bedroom, three and one-half bath unit at perle du lac offers residents lakefront living on the chain of... more
Winter park’s crème de la crème! This exquisite three bedroom, three and one-half bath unit at perle du lac offers residents lakefront living on the chain of lakes. Gated entry, access controlled doors, garage parking, and elevator service are just a few of the first class amenities this community has to offer. Resort style pool and professionally landscaped gardens illustrate the tranquil beauty hidden within the gates. Inside find 2,290 sf of luxurious living space. The grand foyer welcomes you into the home and leads you into the living and dining rooms where arched entries, bamboo flooring, crown molding, and water views provide great space for entertaining. Sliding glass doors open off the living room to the home’s covered balcony with fantastic lake views! The chef’s kitchen with solid wood cabinetry, granite countertops, built-in appliances, and bead board detailing along the bar is open to a second living room or parlor. Master retreat features a custom walk-in closet, jetted tub, his and her vanities, and glass shower. Guest bedrooms are comfortable in size, have generous closets, and are each accessorized with a juliette balcony. Located just steps from park avenue, enjoy maintenance free living in one of winter park’s premier developments and take advantage of its convenient location to the avenue’s boutique shops, fine dining, and the morse museum. 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: Monday, July 6, 2015 at 12:15 PM