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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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$599,900
$2,222/mo
Monthly Payment:
$2,222
Principal & Interest:
$2,222
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $119,980 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 2,159sq ft $278 / sq ft SFR
Lot Size6,831sq ft Built2015 On Site53days
Brand new winter park contruction. Recently completed home on the corner of kenwood and beloit with the wow factor! A great opportunity to purchase in an area of new homes. The... more
Brand new winter park contruction. Recently completed home on the corner of kenwood and beloit with the wow factor! A great opportunity to purchase in an area of new homes. The architecture of this home combines a tile roof spanish style exterior and a modern, clean lines interior. You will be delighted with the amount of natural sunlight that pours into the house, enhancing the elegant fixtures and open feeling. The first floor boasts a large area for living and entertaining, and a bedroom suite, complete with pocket doors and its own bathroom and oversized closet. This is a perfect transitional area that can also be used for a library or guest suite. The kitchen features european style cabinetry, pendant lighting, stainless steel appliances, an oversized island/snack bar and a large pantry. Stylishly practical, travertine flooring spans throughout the entire 1st floor. Volume ceilings and 9 foot doors complete the look, including a sweeping cathedral ceiling between the dining area and great room. French doors lead to the patio already equipped with cabinets and sink for an outdoor kitchen, and a lovely backyard area. The first floor is then split into an area that leads to a full size laundry room, private half bath, and a beautiful back staircase of wood and wrought iron. The master bedroom boasts a balcony off the front, and a privately situated and spacious master bathroom in the back. An additional bedroom ensuite completes the 2nd floor. Many additional features and details. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
We show you every available listing. Here's how
$750,000
$2,778/mo
Monthly Payment:
$2,778
Principal & Interest:
$2,778
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $150,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,818sq ft $413 / sq ft SFR
Lot Size12,547sq ft Built1945 On Site53days
Note: value of this property is in the land and its winter park location . Corner lot with 190 ft frontage on summerland ave (east-west) and 65 ft on summerland ave... more
Note: value of this property is in the land and its winter park location . Corner lot with 190 ft frontage on summerland ave (east-west) and 65 ft on summerland ave (north-south) one block from lake maitland and just a couple blocks north of park avenue. The house on the property, though well kept and very livable as is, is dwarfed by the newer much larger homes built in this area of winter park. This house can be demolished for construction of a new home / mansion more compatible to the neighborhood and use of the impact fee credits and utility hook ups or the house could be substantially expanded and renovated to be compatible with surrounding houses. The corner lot has some nice oak trees and has a fenced back yard. The house is 3 bedrooms with 3 baths, a large living and dining room and kitchen. The 3rd bedroom and bath are set up as an attached guest room or mother in law suite off the living room. There is a 2 car carport with storage room/laundry room at the end. Again, the house is nice and livable but the highest and best use of this property is in construction of a larger home / mansion compatible with the surrounding homes. Just a block from lake maitland and a couple blocks north of park avenue make this a very desirable location. less
Listing Provided Courtesy of P M Properties
Popularity
$425,000
$2,045/mo
Monthly Payment:
$2,045
Principal & Interest:
$1,574
HOA Dues:
$471
(Based on a 30 year fixed loan at 3.75% with $85,000 down)
Winter Park, FL 32789
3bed 3bath 1,944sq ft $219 / sq ft CND
Lot SizeN/Asq ft Built2004 On Site54days
Open Sat Aug 1, 11am-1pm
Rarely available, this condo in the Arbors on Aragon is charming and conveniently nestled near the heart of Olde Winter Park. This three bedroom and three bathroom property is... more
Rarely available, this condo in the Arbors on Aragon is charming and conveniently nestled near the heart of Olde Winter Park. This three bedroom and three bathroom property is filled with a generous amount of natural light and nicely appointed finishes. A few of these quality appointments include hardwood flooring, crown molding, volume ceilings, granite counter tops, pavered porches and a tile roof. Built in 2004, the floor plan is modern and functional. The kitchen, dining and family room spaces are sizeable and open to each other. The kitchen features granite counter tops, stainless appliances, a built-in desk, pantry closet and abundant cabinetry for storage. The pavered and nicely landscaped backyard is fully fenced and accessed from the family room area. The downstairs bedroom has an adjacent full bathroom. This room can easily be doubled as a den or home office. Completing the first floor is an interior utility room with hidden storage and an attached one car garage. Headed to the second level, you will find decorative iron railing accents. The second bedroom and ensuite bath face out over the front of the home with french doors leading to a private balcony with great views of Alfond Stadium. Across the landing is the expansive master suite, thoughtfully finished with wide plank flooring, walk-in closet with built-in organization system, and french doors leading to the serene screened balcony. Exquisite master bath includes double sinks, a garden tub, and separate shower. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$489,000
$1,811/mo
Monthly Payment:
$1,811
Principal & Interest:
$1,811
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $97,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,944sq ft $252 / sq ft SFR
Lot Size10,365sq ft Built1960 On Site54days
Classic Kenilworth Shores Home features Traditional Floor Plan, Original Hardwood Floors & Beautiful Crown Molding! Lovely Foyer opens to large Living room with wood burning... more
Classic Kenilworth Shores Home features Traditional Floor Plan, Original Hardwood Floors & Beautiful Crown Molding! Lovely Foyer opens to large Living room with wood burning fireplace & custom built-in bookcases. Light & bright Dining Room with original built-in corner cupboards & french doors. Delightful updated kitchen with Stainless Steel Appliances & breakfast bar overlooking cozy Family Room. AMAZING Custom POOL with hot tub & fountains is the perfect centerpiece for the spacious multi-level backyard oasis! This home has been lovingly maintained PLUS Upgrades include: Roof 2011. Plumbing 2006, AC 2008, Interior & Exterior Paint 2014-2015, Awnings 2014, Appliances 2014 PLUS BRAND NEW sod & sprinkler system to enhance already beautiful front yard curb appeal!! Extra special features: 2 car garage & Brookshire Elementary, Glenridge Middle & Winter Park High School! Property located in a fantastic neighborhood with views of Lake Berry across the street!! WELCOME HOME! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$389,900
$1,444/mo
Monthly Payment:
$1,444
Principal & Interest:
$1,444
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $77,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,904sq ft $205 / sq ft SFR
Lot Size6,750sq ft Built1950 On Site54days
This gorgeous Orwin Manor mid century home is totally renovated! The home features beautiful wood floors throughout the entire home. The brand new kitchen is state of the art... more
This gorgeous Orwin Manor mid century home is totally renovated! The home features beautiful wood floors throughout the entire home. The brand new kitchen is state of the art with granite counter tops, expresso custom cabinets and all new stainless steel appliances. The bathrooms are also brand new with custom stone tile. The interior has fresh paint throughout the home and customized wood casings around all windows. The home has all new thermal windows. The exterior has new stucco and has been freshly painted. There is new PVC coated soffit and fascia. There is new AC, new HVAC system, updated electrical and the roof is 3 years old. The home also has a paver driveway, slate porch and new sod. Shows great! **Owner financing available!** **Virtual tour available** less
Listing Provided Courtesy of Razzani International Realty
Popularity
$419,000
$1,552/mo
Monthly Payment:
$1,552
Principal & Interest:
$1,552
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $83,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,902sq ft $220 / sq ft SFR
Lot Size6,389sq ft Built1926 On Site54days
Charming and private Winter Park bungalow nestled between larger homes on quaint brick street. Lots of details within this home. Beautiful old and new hardwood floors and volume... more
Charming and private Winter Park bungalow nestled between larger homes on quaint brick street. Lots of details within this home. Beautiful old and new hardwood floors and volume ceilings with lots of light. Intricate wood work on ceilings adds to the charm.Large dining room with bay window. Cherry wood cabinets,granite counters, stainless steel appliances and Mediterranean tile in the over-sized kitchen. You will love the picture window in over the kitchen sink looking at the lush vegetation. Field stone-two-sided wood burning fireplace, family room and kitchen. The room sizes are perfect for a starter home or downsize. Two bedrooms on the first floor featuring Kahrs hardwood floors and more great ceilings. Private bathroom. Upstairs is a true master retreat including separate office that could be 4th bedroom. Master is generous and also has fireplace and gorgeous picture windows to the trees. Well-appointed master has lots of updated built-ins to show off paintings and treasures. Completely remodeled master bathroom has tons of natural light and handpicked Spanish tiles. Outside you have a clean slate with lots of lush vegetation and brick patio and fenced. Detached office guest house is a perfect get-away or terrific storage area. Some of the most recent upgrades include -new French doors. Roof replaced 2010-2011. ADT alarm system. Water heater 2014.Close to shopping, Winter Park schools, Phelps Park, Baldwin Park dog park Publix and Park Avenue. This area is a gem for running, walking, biking and more! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$834,900
$3,093/mo
Monthly Payment:
$3,093
Principal & Interest:
$3,093
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $166,980 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,518sq ft $237 / sq ft SFR
Lot Size14,091sq ft Built1964 On Site55days
Southern traditional house on a large corner lot in one of the best neighborhoods of Winter Park. The home is a short bike ride to Park Ave and centrally located between Winter... more
Southern traditional house on a large corner lot in one of the best neighborhoods of Winter Park. The home is a short bike ride to Park Ave and centrally located between Winter Park & Maitland. Easy access to I-4, 17-92, and downtown Orlando. This 5 bedroom/4.5 bathroom home has an extra-large covered front porch with porch swing and bead board ceiling. Main home has 4 bedrooms and 3.5 baths but, also includes a detached guest room with full bathroom. With almost 3600 square feet, wood floors throughout the living rooms and master bedroom, refinished terrazzo in the additional bedrooms, bright, open and airy rooms, make this house the perfect place to call home! Master bedroom includes 2 custom built shelved closets; one being a large walk-in, perfect for the lady of the house. Laundry room is located between the bedrooms. The kitchen centered by a custom built island, is a cook’s dream with a Thermador professional range and GE Monogram fridge and microwave. This home has 3 fireplaces: a gas burning fireplace in the family room, a wood burning fireplace in the dining room and on the back covered patio. The dining room has a custom built wet bar with a sink, ice maker and 2 wine fridges. The family room, which opens to the kitchen, has an attached powder room with custom built cabinets surrounding the fireplace. French doors, a large driveway, and many other custom touches found in this timeless family home. Only showing to qualified, serious buyers. Don't miss the opportunity to own this stunning home! less
Listing Provided Courtesy of Palmano Group Re Brokerage Llc
Popularity
$1,400,000
$5,186/mo
Monthly Payment:
$5,186
Principal & Interest:
$5,186
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $280,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 3,834sq ft $365 / sq ft SFR
Lot Size17,835sq ft Built1955 On Site55days
Located in the desirable heart of the VIA's, this cottage style home in SICILIAN SHORES, is a meticulously renovated Winter Park beauty! Nestled quietly on an approx 18,000 Sq... more
Located in the desirable heart of the VIA's, this cottage style home in SICILIAN SHORES, is a meticulously renovated Winter Park beauty! Nestled quietly on an approx 18,000 Sq ft. CORNER LOT within minutes of the RACQUETBALL CLUB. You have to see this home to truly appreciate all it has to offer but just to name a "few" . . . CHERRY HARDWOOD floors, Elegant MANICURED LAWN, LAP POOL with HOT TUB, COBBLESTONE PAVERS, DESIGNER LIGHT FIXTURES, SUB ZERO and THERMADOR APPLIANCES, CAMERA SECURITY SYSTEM, MEDIA ROOM, DESIGNER WINDOW TREATMENTS, WALL TO WALL WINDOWS, HOME AUDIO SYSTEM, A TRUE MASTER SUITE which features a JET TUB in the master bath and STEAMER in the DUAL HEAD shower, CALIFORNIA CLOSETS, HIGH VOLUME and TRAY CEILINGS, SKYLIGHTS, HOME GENERATOR, and a 40YR ELK DIMENSIONAL SHINGLE ROOF. Elegance, privacy, and sophistication combined with quality finishes and touches makes this home a true gem! less
Listing Provided Courtesy of Estates Homes Sales & Rentals
Popularity
$999,999
$3,704/mo
Monthly Payment:
$3,704
Principal & Interest:
$3,704
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $200,000 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 3bath 2,812sq ft $356 / sq ft SFR
Lot Size9,645sq ft Built2001 On Site56days
Stunning! That is the only way to describe this gorgeous custom home on Lake Killarney in Winter Park.This home is completely upgraded and in excellent condition! More than... more
Stunning! That is the only way to describe this gorgeous custom home on Lake Killarney in Winter Park.This home is completely upgraded and in excellent condition! More than move-in ready. Amenities include: Coquina rock flooring downstairs, Black Bottom Pool, Custom tile and wood work in all bathrooms, Granite Counter tops in kitchen with designer island. Custom cabinets throughout Mini bar area downstairs with wine cooler.Upstairs bar area with mini fridge. Courtyard Gas fireplace., Wired for surround sound in most rooms. Oversized master bedroom adjoined by a bedroom /optional home office with balcony facing lake. Split plan bedrooms. Mature landscaping- complete privacy for neighbors. Private Lake /alligator free. Plantation shutters, bamboo window treatments, Storage area inside under staircase with doggie door and gated yard for pets 3 minutes to I-4 by car and 3 minutes by boat to Hillstones, Trader Joes and Shake Shack off of Fairbanks Ave. You get convenience and paradise at the same time. less
Listing Provided Courtesy of Re/max Prime Properties
Popularity
$159,000
$589/mo
Monthly Payment:
$589
Principal & Interest:
$589
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $31,800 down)
Winter Park, FL 32792
Goldenrod Orange County School District
4bed 2bath 1,347sq ft $118 / sq ft SFR
Lot Size11,133sq ft Built1959 On Site56days
Short sale. Listing price approved by lender.All home square footage and lot size, if exact square footage is concern, the property should be independently measured. Seller does... more
Short sale. Listing price approved by lender.All home square footage and lot size, if exact square footage is concern, the property should be independently measured. Seller does not provide condo/ hoa docs, this is the responsibility of the buyer. All information recorded in the mls is intended to be accurate but cannot be guaranteed, buyer advised to verify. Seller has retained an attorney to negotiate the short sale transaction. less
Listing Provided Courtesy of Florida Realty Team Of Central
Popularity
$223,500
$828/mo
Monthly Payment:
$828
Principal & Interest:
$828
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $44,700 down)
Winter Park, FL 32789
Orange County School District
4bed 2bath 1,269sq ft $176 / sq ft SFR
Lot Size7,043sq ft Built1947 On Site57days
Location, Location, Location Wonderful Winter Park location. From this charming 4 bed room family home you can walk or bike to downtown Winter Park, College Park, Florida... more
Location, Location, Location Wonderful Winter Park location. From this charming 4 bed room family home you can walk or bike to downtown Winter Park, College Park, Florida hospital, sun rail, Loch Haven arts and cultural areas, Mills Park and much more. Fully remodeled in 2012! New HVAC, appliances, bathrooms, windows, doors, front porch, plumbing, electrical, floor tile throughout. The backyard has plenty of room for the kid's, pets, garden, pool etc. This house is in move-in ready condition. Side and rear entry, storage closet/laundry sink, indoor laundry, Irrigation system with well, outside storage shed. This home is very nice and we will choose the strongest offer. Put in your offer today, won't last long! less
Listing Provided Courtesy of Cornerstone Real Estate Llc
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 32792
Orange County School District
6bed 4bath 5,449sq ft $193 / sq ft SFR
Lot Size20,128sq ft Built2000 On Site57days
Priced $200,000 below appraisal! Our loss is your gain! Nestled in desirable winter park, come home to your own private oasis! Sprawling oak trees and a sweeping landscape... more
Priced $200,000 below appraisal! Our loss is your gain! Nestled in desirable winter park, come home to your own private oasis! Sprawling oak trees and a sweeping landscape welcome you to this 6 bed/4 bath 2-story custom home on a premium 1/2 acre lot. step in through the front door and fall in love with the soaring cathedral ceilings and stunning floor-to-ceiling glass windows that flood the elegant living room with natural light. This spacious beauty also boasts 2 master suites (one on each floor) and a separate 2-bedroom first floor suite perfect for in-laws or an extended family! the first floor bedrooms open up to a private deck with a hot tub where you can relax in comfort under the stars. Or if you're feeling like entertaining, host a spectacular party in your expansive back yard! Back inside, enjoy the views of your garden or catch a cardinal or blue-jay flying by while making breakfast in your bright, open kitchen or while unwinding in the family room. Upstairs you'll find three bedrooms, including the second master suite all with private balconies! A den/library & large bonus room complete the second floor. entry and exit are easy in your oversized garage, thanks to double doors that open on both sides. When you're ready to leave, nearby shopping & restaurants abound, including the world-class shops and restaurants of park avenue! Plus, convenient to wp hospital, ymca, whole foods, phelps park & interlachen country club; along with a-rated schools. call today for a private showing! less
Listing Provided Courtesy of Keller Williams Heritage Rlty
Popularity
$365,000
$1,352/mo
Monthly Payment:
$1,352
Principal & Interest:
$1,352
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $73,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 1,705sq ft $214 / sq ft SFR
Lot Size4,908sq ft Built1926 On Site58days
Renovated completely! This 1926 Winter Park Bungalow offers today’s comforts with yesterday’s charm. Refinished hardwood floors throughout. Three bedrooms upstairs... more
Renovated completely! This 1926 Winter Park Bungalow offers today’s comforts with yesterday’s charm. Refinished hardwood floors throughout. Three bedrooms upstairs are the perfect place to find rest & relaxation. The Master Suite is large and one of the other bedrooms upstairs can be used as an office, library or nursery. Upstairs bathroom was recently remodeled with a new shower, tile, and more! Light and bright kitchen offers counter bar seating, all appliances and cabinetry – all open to the Sun Room with French doors overlooking the courtyard and patio. Detached Guest Suite also remodeled – new metal roof, doors, windows and separate A/C! Many, many more upgrades! You will love the feel and style of this impeccably maintained home! Call today for your private showing! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$359,900
$1,333/mo
Monthly Payment:
$1,333
Principal & Interest:
$1,333
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $71,980 down)
Winter Park, FL 32792
Orange County School District
5bed 3bath 2,990sq ft $120 / sq ft SFR
Lot Size8,282sq ft Built1991 On Site58days
Well Maintained and Move In Ready. This 5 bedroom, 3 bath, spacious home is located on a private, low traffic cul-de-sac. The home has a very open floor plan with vaulted... more
Well Maintained and Move In Ready. This 5 bedroom, 3 bath, spacious home is located on a private, low traffic cul-de-sac. The home has a very open floor plan with vaulted ceilings. Kitchen has granite and a large breakfast bar overlooking the great room. Wood burning fireplace in the great room. The master and one other bedroom are down stairs. There are three large bedrooms and a loft upstairs. Enjoy your private completely fenced back yard from the covered and screened lanai. The home has been re-plumbed. Truly well maintained and shows well! WINTER PARK HIGH School District. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$395,000
$1,463/mo
Monthly Payment:
$1,463
Principal & Interest:
$1,463
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $79,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,513sq ft $157 / sq ft SFR
Lot Size9,771sq ft Built1954 On Site58days
Live big on burks circle in this updated 2513 sf one level home with an open floor plan and four bedrooms plus an office or 5th bedroom! Sleek kitchen with black granite,... more
Live big on burks circle in this updated 2513 sf one level home with an open floor plan and four bedrooms plus an office or 5th bedroom! Sleek kitchen with black granite, stainless appliances and maple cabinets. Large master suite has a nice bath with a jetted soaking tub, double vanities, double headed shower and huge walk in closet. The master and living area open onto a wonderful deck for backyard entertaining. Open kitchen, dining and living areas and a split bedroom plan with two other full baths beautifully redone in 2012. A-rated schools, and all in 32789. Neat as a pin, freshly painted and move in ready this home is in a most convenient location near schools, hospital, restaurants and the lovely windsong community of winter park. This is the perfect starter home for a young family or a superb downsize home for the empty nester with plenty of room for guests and space for entertaining. Make it yours and have great location, good schools and a fun open home for living the winter park lifestyle. less
Listing Provided Courtesy of Coldwell Banker Residential Re
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.

Copyright 2015 Mid-Florida Regional Multiple Listing Service. All rights reserved.

Data last updated: Saturday, August 1, 2015 at 9:49 AM. Properties in listings may have been sold or may no longer be available.