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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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$572,000
$2,119/mo
Monthly Payment:
$2,119
Principal & Interest:
$2,119
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $114,400 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 2,640sq ft $217 / sq ft SFR
Lot Size2.9acre Built1980 On Site19days
Open Sun Aug 30, 2pm-4pm
Lakefront paradise! Spacious four beds, three baths 2,640 sq. ft. home in a desirable, quiet neighborhood overlooking spring fed Lake Ann. Take your canoe out and enjoy fishing... more
Lakefront paradise! Spacious four beds, three baths 2,640 sq. ft. home in a desirable, quiet neighborhood overlooking spring fed Lake Ann. Take your canoe out and enjoy fishing for bass! Sit dockside to experience stunning sunsets and sunrises. This house is perfect for entertaining, with gorgeous views of the lake from almost every part of the home. The home features built in bookcases in three of the rooms, crown molding, plantation shutters throughout and vaulted ceilings. A fireplace is in the family room along with a separate living room. French doors lead to a large screened in porch, perfect for an inside/outside sitting area. Double pane vinyl clad windows help keep the house on a year round temperate setting. The home also has an Electric Energy Miser and gets credits from Duke Energy back monthly. This home has a very large backyard with an oversized patio that has plenty of room for a pool, mature landscaping and a beautiful weeping willow tree. The property features a solid 1 acre of land, a storage shed and a lake fed sprinkler irrigation system. The garage has room for plenty of storage with a closet and also a workbench with built in cabinets. The house has been inspected for termites in August 2015 and has passed all annual termite inspections. The property also has a new 1.5 horsepower irrigation pump was added in 8/2015. Close to Interlachen Country Club, several shopping and retail area & Howell Branch Park. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
We show you every available listing. Here's how
$1,525,000
$5,871/mo
Monthly Payment:
$5,871
Principal & Interest:
$5,650
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $305,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,400sq ft $347 / sq ft SFR
Lot Size14,906sq ft Built2005 On Site19days
A truly magnificent French Provincial on the N. side of the prestigious Windsong community in olde Winter Park... Extensive use of detailed ceilings & moldings, solid walnut... more
A truly magnificent French Provincial on the N. side of the prestigious Windsong community in olde Winter Park... Extensive use of detailed ceilings & moldings, solid walnut hardwood & Italian travertine floors, 3 fireplaces, French doors, plantation shutters, and true craftsmanship throughout that we have come to expect in a "Carlos Posada" signature custom home... Elegant 2-story entrance foyer opening to formal dining & living rooms each with their own personalized beautiful masonry fireplaces... Exquisite designer lighting with crystal & iron chandeliers, built-ins, shelving, quality cabinetry, exotic granite & stone counters... Wonderful 1st floor master retreat with private courtyard, his/her closets & spa like bath, chef's island kitchen with commercial appliances open to family room with stunning high beamed ceiling, additional downstairs bedroom or study & mud room... Upstairs includes 3 or 4 bedrooms plus a bonus/media room along with a main front and rear stairway access... Outdoor lifestyle includes multiple covered areas including a lanai sitting area with tv, detached cabana w/ masonry fireplace, classic over sized lap pool with fountain feature, iron fencing, motor court with 3 garages & lush professional landscaping... A must see stunning home convenient to club style community pool, park, playground & lake access... less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$269,900
$1,000/mo
Monthly Payment:
$1,000
Principal & Interest:
$999
HOA Dues:
$1
(Based on a 30 year fixed loan at 3.75% with $53,980 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,627sq ft $166 / sq ft SFR
Lot Size8,400sq ft Built1971 On Site19days
Don't miss out on this beautiful winter park home. The owner loss is your gain owners just finished remodeling and have now decided to move out of state. New within the last 2... more
Don't miss out on this beautiful winter park home. The owner loss is your gain owners just finished remodeling and have now decided to move out of state. New within the last 2 months. Solid wood watermark cabinets with glass doors and granite counter tops soft close drawers and doors and recessed lighting. Total new stainless steel appliance pkg. New double pain windows throughout the home. New hot water heater 7 months old. Extra large master bedroom with master bath completely remodeled. New additional insulation the inside super sized laundry has a wash tub and the list goes on. Roof 4.5 years old. All flooring tile or laminate. French doors lead you to enjoy a super large patio with inground newly refinished spa which opens to outside brick patio with fire pit the ultimate for entertaining. Beautiful landscaping plentiful fruit trees home backs up to interlachen golf course conservation area. Nothing lacking here except you. Come out and see this special home. less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$299,900
$1,111/mo
Monthly Payment:
$1,111
Principal & Interest:
$1,111
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $59,980 down)
Winter Park, FL 32792
Seminole County School District
4bed 2bath 2,100sq ft $143 / sq ft SFR
Lot Size13,256sq ft Built1986 On Site20days
Open Sun Aug 30, 1pm-4pm
Wonderful Winter Park home with A+ rated Seminole County schools. VIEW VIRTUAL TOUR for over 70 pictures! Desirable Quail Run! Lovingly maintained with fresh interior paint and... more
Wonderful Winter Park home with A+ rated Seminole County schools. VIEW VIRTUAL TOUR for over 70 pictures! Desirable Quail Run! Lovingly maintained with fresh interior paint and new architectural 20 year roof in 2014. Great split bedroom plan. Very spacious kitchen, with large eat in space, which opens on to the inviting family room with brick trimmed wood burning fireplace. Vaulted ceilings in many of the rooms adds to the overall spacious feeling. Large master bedroom retreat that opens on to the large covered/screened back porch. Bath has a large Jacuzzi tub and separate shower. This porch is the perfect place to start your day with a cup of coffee or just relax at the end of a long day. Solid wood doors and trim throughout are very high quality. Oak kitchen with newer appliances with a window access to the porch for entertaining. Large Corner lot with nice landscaping. Pool planned for the future if you want to build your own design. Great location, easy access to the Cady Way Trail for recreation and a short distance to the SR417 to ease your commute. Come see all this home has to offer you will not be disappointed! Pride of ownership shows through. less
Listing Provided Courtesy of Charles Rutenberg Realty
Popularity
$700,000
$2,593/mo
Monthly Payment:
$2,593
Principal & Interest:
$2,593
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $140,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,304sq ft $304 / sq ft SFR
Lot Size11,996sq ft Built1950 On Site21days
Enjoy Florida's outdoor lifestyle in the heart of Winter Park. The split-level layout of this 2300+ sq ft 3-bedroom 2.5-bath is flooded with natural light. Multiple outdoor... more
Enjoy Florida's outdoor lifestyle in the heart of Winter Park. The split-level layout of this 2300+ sq ft 3-bedroom 2.5-bath is flooded with natural light. Multiple outdoor living spaces including gated courtyard, balcony facing Lake Sue Ave, open porch under pergola, and large screened porch overlooking heated salt water pool and lush back yard, bringing the outdoors into every room. The open floor plan combinines living room, dining and sitting rooms. Travertine tile throughout the first floor, and solid oak floors upstairs. Kitchen features gas range, black granite, solid wood cabinets, breakfast bar and large eat-in area. Generous utility room with sink and extra storage. Reverse osmosis water filtration and tankless hot water. Spacious 2-car garage. Less than 1 mile to Park Ave, East End Market and lots of convenient shopping and dining. Excellent Winter Park schools. Circular drive for easy access. Deeded access to Winter Park Chain of Lakes completes the package. Let this home be your refuge from the maddening world! YOU MUST SEE THIS BEAUTIFUL HOME TO APPRECIATE IT. less
Listing Provided Courtesy of Keller Williams Winter Park
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 1,868sq ft $241 / sq ft SFR
Lot Size12,002sq ft Built1955 On Site21days
Great opportunity to purchase a 0.28 acre lot in one of Winter Park’s most desirable areas. Set back behind the Park Grove community this 145x80’ parcel is located... more
Great opportunity to purchase a 0.28 acre lot in one of Winter Park’s most desirable areas. Set back behind the Park Grove community this 145x80’ parcel is located on a quiet cul-de-sac, surrounded by mature oaks and a mix of charming, remodeled ranch homes and new construction. Existing three bedroom, two bath home has recently undergone some renovations; new tile floors throughout the living and den areas, as well as updated countertops and stainless steel appliances in the kitchen. Two-car garage has been converted into an extra storage room, with wall mounted air conditioning; however it could easily be converted back into a garage. Covered patio and screened in pool are in great shape! Move in, tear down, or renovate – the choice is up to you. Zoned for A-rated Winter Park schools and within close proximity to Park Avenue, Hannibal Square and the Winter Park Golf Course. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$695,900
$2,578/mo
Monthly Payment:
$2,578
Principal & Interest:
$2,578
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $139,180 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,060sq ft $227 / sq ft SFR
Lot Size6,534sq ft Built2015 On Site22days
Open Sun Aug 30, 1pm-3pm
Are you looking for new custom built construction in Winter Park? This home in sought after Hamilton Place is an executive level home. Very open and light floor plan. You are... more
Are you looking for new custom built construction in Winter Park? This home in sought after Hamilton Place is an executive level home. Very open and light floor plan. You are greeted with tall ceilings, neutral flooring, open kitchen with Viking appliances. Great entertaining floor plan with family room open to the kitchen area. Secondary rooms are downstairs, one with on-suite full bath. Half bath downstairs for guest. Spacious Master Bedroom is upstairs, spacious and light. Large master bath with huge shower and separate tub. Loft area upstairs, can be an office, workout area; etc. Double pane insulated windows, tile roof, brick pavered driveway. This home is easy living with low maintenance landscaping! Hamilton Place is situated minutes to Park Ave and Rollins College & the Sunrail . Short walk to the Winter Park Village for dining, entertainment and shopping. Enjoy a short jaunt down to the Mills Art district and minutes to I4 and Downtown Orlando. Enjoy the Farmers Market and all the other amazing activities Downtown Winter Park has to offer. Call today for your private showing! less
Listing Provided Courtesy of Bhhs Florida Realty
Popularity
$294,000
$1,089/mo
Monthly Payment:
$1,089
Principal & Interest:
$1,089
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $58,800 down)
Winter Park, FL 32792
Seminole County School District
3bed 3bath 1,776sq ft $166 / sq ft SFR
Lot Size9,030sq ft Built1969 On Site23days
Fully renovated from top to bottom, move in ready Winter Park home. Brand new cherry cabinets and granite counter tops throughout. New tile and laminate hardwood. All bedrooms... more
Fully renovated from top to bottom, move in ready Winter Park home. Brand new cherry cabinets and granite counter tops throughout. New tile and laminate hardwood. All bedrooms are on the second floor. Zoned for Seminole County Schools. Just minutes from UCF, Rollins College, Full Sail University, Winter Park Chain of Lakes, Park Avenue, Winter Park YMCA, shops and restaurants. Call today for an appointment to see this amazing home. less
Listing Provided Courtesy of Exit Realty Central
Popularity
$190,000
$703/mo
Monthly Payment:
$703
Principal & Interest:
$703
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $38,000 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
5bed 3bath 2,284sq ft $83 / sq ft SFR
Lot Size7,492sq ft Built1968 On Site23days
Back on the Market! Need space?? This 5BD+ office/3BA Eastbrook home has what you need! The garage was professionally enclosed for in-law suite (2nd master) and also features a... more
Back on the Market! Need space?? This 5BD+ office/3BA Eastbrook home has what you need! The garage was professionally enclosed for in-law suite (2nd master) and also features a home office area with built-in all around desk. 3 additional guest bedrooms (1 with built-in corner desk and shelving). All cable wiring is new 2 years ago, several rooms are hard-wired for cat 5, home theater in living room with 100" viewing wall and projector stays! Stainless steel counter depth french door fridge and matching dishwasher are Kitchen Aid Architect Series. Bathroom tiles just resurfaced, newer roof, recent exterior paint, wood laminate and tile floors. No carpet! Patio needs work but is framed for HUGE screened in area, fully fenced yard, and storage shed. Great shady trees out back! less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$649,000
$2,404/mo
Monthly Payment:
$2,404
Principal & Interest:
$2,404
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $129,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,812sq ft $358 / sq ft SFR
Lot Size12,594sq ft Built1925 On Site24days
Beautifully renovated, this 1925 home will give you all the charm of historical homes, with the livability of today's style and décor! Large sun porch, windowed and under... more
Beautifully renovated, this 1925 home will give you all the charm of historical homes, with the livability of today's style and décor! Large sun porch, windowed and under air, spans the front of the home. Two sets of original, glassed, double doors enter to the spacious living room. Gorgeous, original hardwood floors throughout. Wood-burning fireplace in living room. All new thermal-paned windows. Newer kitchen w/ limestone counter tops, stainless-steel appliances. Over-sized lot will allow for approx. 2,500 sq. ft. additional construction. Completely fenced! less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity
$385,000
$1,426/mo
Monthly Payment:
$1,426
Principal & Interest:
$1,426
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $77,000 down)
Winter Park, FL 32792
Golfside Orange County School District
3bed 2bath 1,930sq ft $199 / sq ft SFR
Lot Size9,106sq ft Built1979 On Site24days
Winter Park Pines Golf Course Home! Location very desirable! Homes in this premier section of Golfside rarely come up for sale. Light and bright, Spanish style, three bedroom,... more
Winter Park Pines Golf Course Home! Location very desirable! Homes in this premier section of Golfside rarely come up for sale. Light and bright, Spanish style, three bedroom, two bath home on quiet tree-lined street. The home has a split bedroom floor plan with stunning new hardwood floors throughout, an open living/dining room, family room with stone wood burning fireplace. Beautiful views from living room of picturesque yard and street. Kitchen features dual sinks and silestone counters with travertine tile backsplash, breakfast bar, stainless steel refrigerator and eat-in area. Family room is open and spacious. Scenic views of golf course from dining, family and kitchen. Generous inside laundry room is very rare and a bonus. Spacious master suite has a large walk in closet, separate dressing area with vanity, and bathroom with newer walk-in shower. The home is set back enough that there is no worry of errant golf balls. Scenery is lush. The backyard and recently renovated screened in porch is a huge hit for golf enthusiasts to enjoy watching the action. Still room to fence in or build a pool. Newer sliders. Window replacement on many windows. Water heater within the past 10 years and barrel tile roof that should last a lifetime. This home is conveniently located near great Winter Park schools, Brookshire, Glenridge and Winter Park High School. Park Avenue, Cady Way Trail and several shopping and dining destinations within biking and walking distance. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$2,290,000
$8,705/mo
Monthly Payment:
$8,705
Principal & Interest:
$8,484
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $458,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 7,113sq ft $322 / sq ft SFR
Lot Size20,097sq ft Built2006 On Site24days
Windsong-north shore-winter park-new offering exceptional opportunity to own one of winter park’s signature residences. The mediterranean inspired 5 bedroom 5 bath... more
Windsong-north shore-winter park-new offering exceptional opportunity to own one of winter park’s signature residences. The mediterranean inspired 5 bedroom 5 bath residence was custom crafted by well-respected cahill homes in 2006. The interior finishes and attention to detail add to the residence’s architectural design which have been enhanced by the custom millwork, beam ceilings, travertine and wood flooring, coffered hand painted ceilings and 450 sf salt water aquarium. The european inspired country kitchen is highlighted by the arch brick ceiling, custom crafted cabinetry, center island with sink, granite countertops, 2 subzero refrigerators built in miele coffee machine, wolf range oven, warming drawer and microwave, 2 bosch dishwashers, wine cooler and wine cellar. The estate features 3 gas fireplaces. The master retreat is spacious and elegant while being inviting and comfortable. The owner’s bath features his and her custom vanities, elaborate shower with multiple spray jets along with an outside garden shower. Additional features include a large game room, home theater and 2 laundry rooms. The estate’s outdoor living area has been designed to flow freely between the interior living space by large retractable doors. Features include kitchen with gas grill, gas fireplace and retractable screens overlooking the free form pool and spa. Community features include pool, playground, park and lake access. less
Listing Provided Courtesy of Stirling Sotheby's Int'l Rlty
Popularity
$330,000
$1,222/mo
Monthly Payment:
$1,222
Principal & Interest:
$1,222
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $66,000 down)
Winter Park, FL 32792
Orange County School District
3bed 3bath 1,820sq ft $181 / sq ft TWN
Lot Size9,093sq ft Built2014 On Site24days
Brand new, stylish 1,820 sq ft three bedroom, two and one half bath back unit townhome in an established and highly desirable area of Winter Park! Townhome features ceramic tile... more
Brand new, stylish 1,820 sq ft three bedroom, two and one half bath back unit townhome in an established and highly desirable area of Winter Park! Townhome features ceramic tile & wood laminate flooring throughout, downstairs utility room, 2nd floor sun deck/terrace perfect for a Jacuzzi, outside entertaining or observing the night sky, cement patio on 1st floor, 42" high European style kitchen cabinets with granite counter-tops, stainless steel appliances and community green spaces. NO HOA! Min. expenses for common area maintenance will be shared among all owners. Enjoy living near Cady Way and Ward Parks, top rated Winter Park schools, Winter Park Hospital, Whole Foods and all of the local venues near Aloma and Lakemont Avenue. Near Rollins, UCF and Full Sail University. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$1,895,000
$7,026/mo
Monthly Payment:
$7,026
Principal & Interest:
$7,020
HOA Dues:
$6
(Based on a 30 year fixed loan at 3.75% with $379,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,370sq ft $562 / sq ft SFR
Lot Size25,486sq ft Built2010 On Site24days
Fabulous Craftsman style home on Lake Maitland with Old World character & charm… 1st place Parade of Homes winner for architectural woodwork & craftsmanship combined with... more
Fabulous Craftsman style home on Lake Maitland with Old World character & charm… 1st place Parade of Homes winner for architectural woodwork & craftsmanship combined with bright-open floor plan taking advantage of southern views across Lake Maitland towards the Isle of Sicily cove... Hardwood floors, copper clad bay windows, beautiful columns, tongue-&-groove cypress ceilings. Historic antique brick covers the exterior, inside on warm accent walls and flows onto classic wide columned porch… terrific open plan for lakefront entertaining! Beautiful kitchen w/ carrera marble counters, large peninsula with 2nd sink, 2 microwaves, gas cooktop, plus an arched pass-through to dining room & lake views. Two master suites! One down and the upstairs master is entire 2nd floor with wonderful elevated lake views, including sitting room & private lake-view balcony. Downstairs has 3 bedrooms w/ their own full baths, plus a den w/ full bath & claw foot tub. One bedroom has a separate entry and private patio perfect for guest, office or mother-in-law suite. Handcrafted floor-to-ceiling cabinetry surrounds a tiled fireplace with storage beneath. Spectacular sunset views and a full size dock & boathouse… This is a completely custom home unique in style and size to the 6-lake chain of lakes…it's understated, warm, richly detailed…a true inspiring custom home. There is also a side entry 3-car garage with large walk-in attic space over it… great back yard w/ plenty of room to add a pool if desired. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$73,000
$495/mo
Monthly Payment:
$495
Principal & Interest:
$270
HOA Dues:
$225
(Based on a 30 year fixed loan at 3.75% with $14,600 down)
Winter Park, FL 32792
Orange County School District
2bed 2bath 840sq ft $87 / sq ft CND
Lot Size9,439sq ft Built1990 On Site24days
2 Bedrooms & 2 Bathrooms Condo on the 2nd floor featuring Granite in Kitchen and Bathrooms, Cherry Oak Cabinets, Vessel Sinks, Laminate Wood Floors, Stainless Steel Appliances,... more
2 Bedrooms & 2 Bathrooms Condo on the 2nd floor featuring Granite in Kitchen and Bathrooms, Cherry Oak Cabinets, Vessel Sinks, Laminate Wood Floors, Stainless Steel Appliances, and Much More. This lovely and clean Condo is currently rented / kept in a good condition. A great investment property by enjoying the cash flow right away. Close to Rollins, Full Sail, UCF, and Valencia College! A-Rated Winter Park Schools! Close to 417 and 408 for easy commute. less
Listing Provided Courtesy of Keller Williams Classic Realty
Popularity
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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.

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: Saturday, August 29, 2015 at 8:57 PM. Properties in listings may have been sold or may no longer be available.