Winchester CT Homes for Sale

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Type:
Single Family
Sq.Ft.:
980
Status:
NEW LISTING
Beds:
2
Lot size:
0.5 Acres
Year built:
1930
Baths:
1.00
MLS#:
24073939
Subdivision:
Danbury Quarter

ADDITIONAL INFORMATION

An opportunity for redevelopment! This bungalow-style home, situated on a 0.50-acre lot along State-maintained Route 44, is beyond salvageable and will require demolition. Offering 980 sq. ft. of living space with 5 rooms, including 2 bedrooms and 1 full bath, the property is in unsafe condition and there will be no access granted due to structural concerns. While located in a rural setting, it remains conveniently close to local amenities. Sold strictly as-is. Cash purchase required.

Type:
Single Family
Sq.Ft.:
936
Status:
NEW LISTING
Beds:
3
Lot size:
0.8 Acres
Year built:
1935
Baths:
1.00
MLS#:
24073884
Subdivision:
N/A

ADDITIONAL INFORMATION

Charming bungalow with great potential! This 936 sq. ft. home features 6 rooms, including 3 bedrooms and 1 full bath, situated on a spacious 0.80-acre lot. A detached one-car garage provides additional storage or parking. While this home is in poor condition and will require significant renovation, it presents an excellent opportunity for investors or buyers looking to restore and customize. Will not qualify for traditional financing-rehab loan or cash purchase required. Sold as-is. Don't miss the chance to bring this property back to life!

Type:
Single Family
Sq.Ft.:
1,440
Status:
NEW LISTING
Beds:
3
Lot size:
0.12 Acres
Year built:
1927
Baths:
2.00
MLS#:
24074979
Subdivision:
N/A

ADDITIONAL INFORMATION

Charming Lake House Retreat on Highland Lake! Tucked away on a serene road surrounded by lush woods, this property presents a rare blend of seclusion and natural beauty. Located in close proximity to Steven's Reserve of the Winchester Land Trust. If you've been searching for the perfect getaway with lake views, this is the one! Featuring 3 spacious bedrooms and 2 full baths, this home exudes comfort and convenience, along with an additional room that's perfect for a playroom or office - the choice is yours! From the water views visible from both levels, you can own your own slice of New England paradise. Completely upgraded throughout this colonial style home: (2024) New roof, modern bathrooms, fresh LVP flooring, vinyl energy efficient windows, and a brand-new kitchen featuring sleek countertops. Main level laundry room for ultimate convenience. Character and charm throughout the home, with plenty of parking space for guests and visitors. For any investors, this home is an excellent opportunity with potential rental income. Long-term rental projected at $1,500/month. Take advantage of the public lake access with Resha Beach just 4 minutes away and Holland Beach (boat launch) only 7 minutes away. Plus, Platt Hill State Park (78 acres of outdoor activities) is just 10 minutes away. Whether you're looking for a serene getaway, a first home or income potential, the choice is yours!

Type:
Single Family
Sq.Ft.:
1,192
Status:
NEW LISTING
Beds:
2
Lot size:
0.07 Acres
Year built:
1930
Baths:
2.00
MLS#:
24071795
Subdivision:
Winsted

ADDITIONAL INFORMATION

Enjoy water views from this charming Colonial located just across the street from Highland Lake. This cozy retreat blends historic charm with modern updates, offering a perfect escape for year-round living or a weekend getaway. Inside, refinished wide-plank hardwood floors add warmth and character, while the freshly painted interior enhances the bright and inviting atmosphere. The living room features French doors that open to a lovely porch-an ideal spot to sip your morning coffee while soaking in the lake views. The galley kitchen is efficiently designed, and a first-floor half bath with laundry adds convenience. The room off the living room on the 1st floor could serve as an office or third bedroom. Upstairs, you'll find two comfortable bedrooms with cathedral ceilings and an updated full bath. Recent upgrades include a newer heating system (2020) and a brand-new water heater, with efficient propane heat to keep you cozy during colder months. Beyond your doorstep, Highland Lake offers endless recreation-spend your days kayaking, jet skiing, swimming, and fishing in the crystal-clear waters. A nearby marina provides easy access to boat slips, so you can take full advantage of this boater's paradise. Winchester also offers quaint shops, local dining, and nearby hiking trails, making it a sought-after retreat for nature lovers and outdoor enthusiasts. Don't miss this charming lakeside gem and start enjoying all that Highland Lake living has to offer.

Type:
Single Family
Sq.Ft.:
3,021
Status:
NEW LISTING
Beds:
4
Lot size:
4.6 Acres
Year built:
1875
Baths:
3.00
MLS#:
24067951
Subdivision:
N/A

ADDITIONAL INFORMATION

Welcome to this charming four-bedroom antique home that is beautifully renovated to blend timeless character with modern comforts. As you step inside you'll be greeted by the warmth of refinished hardwood floors and an inviting living room featuring a cozy fireplace and built-in bookcases perfect for relaxing or entertaining. The heart of the home is the brand-new kitchen boasting sleek granite countertops, stainless steel appliances and plenty of cabinet space for all your culinary needs. The adjacent dining room is ideal for gatherings or hosting guests. This home offers three fully remodeled bathrooms each showcasing contemporary finishes and thoughtful design. A new second-floor laundry room adds convenience to daily living keeping chores organized and easily accessible. For added versatility, the property includes an in-law apartment providing privacy and comfort for extended guests. Additional upgrades include a new boiler, energy-efficient windows, a new roof and a modern engineered septic system ensuring the home is both efficient and well-maintained. Outside, enjoy the tranquility of a spacious four-acre lot complete with a patio for outdoor dining and relaxation. The large barn with three bays offers ample space for car storage, hobbies, or potential workshop use. With its perfect blend of antique charm and modern updates this home is truly a rare find. Don't miss your chance to experience the best of both worlds.

Open House:

Saturday, 2/22 11:30-1:00PM

Type:
Single Family
Sq.Ft.:
2,239
Status:
NEW LISTING
Beds:
4
Lot size:
0.21 Acres
Year built:
1901
Baths:
2.00
MLS#:
24073605
Subdivision:
Winsted

ADDITIONAL INFORMATION

Welcome to this beautifully renovated home, nicely tucked away in historic Winsted. This lovely property features over 2,200 square feet of gross interior living space. The large kitchen, dining, and living room areas provide a seamless flow, perfect for entertaining. The home boasts four spacious bedrooms and one and a half baths. The beautifully renovated attic adds even more charm and functionality to the space. Additional highlights include modern stainless steel appliances, with all appliances included, and hardwood flooring throughout the home. The beautifully landscaped yard creates a perfect outdoor space for relaxation and gatherings. Conveniently located near local amenities, this home provides easy access to shopping, dining, and more. Experience this beautiful home firsthand Don't miss the opportunity to make this move-in ready gem your new home.

Type:
Condo
Sq.Ft.:
992
Status:
Active
Beds:
2
Year built:
1986
Baths:
2.00
MLS#:
24073529
Subdivision:
N/A

ADDITIONAL INFORMATION

Enjoy the private and peaceful setting of Still River right from your bedroom window or private patio all the while being close to the many amenities offered in town. Inside this well-maintained condo you'll find an abundance of natural light flowing in every room, a bright slider opening up to your own patio, all new paint throughout, lots of storage and durable like-new flooring on the main and upper levels. Perfect for easy maintenance. Parking within steps to your front door and extra spaces available nearby. Outdoor activities abound with fishing, kayaking, golf nearby and a variety of shopping within a mile. Don't miss this opportunity!

Type:
Single Family
Sq.Ft.:
988
Status:
Active
Beds:
3
Lot size:
0.22 Acres
Year built:
1980
Baths:
1.00
MLS#:
24072988
Subdivision:
Winsted

ADDITIONAL INFORMATION

Charming ranch style home with year round water views! This beautifully updated 3-bedroom, 1-bath ranch home in the sought-after Highland Lake community in Winsted is a true gem. The home has been meticulously cared for, blending modern updates with classic charm. Inside, you'll find a cozy, well-maintained living space that feels inviting and comfortable. The property boasts a spacious, full unfinished basement, offering endless possibilities for storage, a workshop, or finishing it to suit your needs. Outside, the level lot features a deck with a lovely pergola, perfect for relaxing or entertaining while enjoying peaceful lake life! Located just steps from Highland Lake, one of the cleanest lakes in the area, the home provides direct access to a boat launch where motorboats are welcome. Whether you're into boating, fishing, or simply soaking in the natural beauty of the lake, this location offers a serene, lakeside lifestyle you won't want to miss.

Type:
Single Family
Sq.Ft.:
5,016
Status:
Active
Beds:
5
Lot size:
0.56 Acres
Year built:
1880
Baths:
4.00
MLS#:
24071827
Subdivision:
Winsted

ADDITIONAL INFORMATION

Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family dwellings, and home farming. Additionally, with a special permit, the property may accommodate a variety of uses, including affordable housing, bed and breakfasts, boarding houses, congregate residences, convalescent/nursing homes, country inns, home occupations, mixed-use buildings, multi-family dwellings, outdoor private recreation and entertainment facilities, restaurants, schools, two-family dwellings, and places of worship. The first floor features spacious rooms that could accommodate a kitchen, pantry, dining room, formal living room, family room, and office. The second floor provides ample space for four to five bedrooms, while the third floor boasts a generously sized apartment, adding flexibility to the layout. A standout feature is the impressive 2,300 sq. ft. three-story barn/garage, offering abundant storage, workshop space, and potential for various uses. Whether you're seeking a unique investment opportunity or a property brimming with character, this exceptional offering is ready for its next chapter.

Type:
Single Family
Sq.Ft.:
1,424
Status:
Active
Beds:
3
Lot size:
0.22 Acres
Year built:
1900
Baths:
1.00
MLS#:
24066803
Subdivision:
N/A

ADDITIONAL INFORMATION

A charming house located 2 blocks from highland lake. This 3 bedroom, 1 large full bath is move-in ready. The dining room has a beautiful built in, the 3 large windows allowing for natural light to brighten the room. Off of the dining room is a nice family room. The kitchen is large and spacious and off the kitchen in the back is a lovely sunroom with a fireplace (natural gas) that has sliders that lead to the deck and the back yard. The laundry room is located on the first floor, the 3 bedrooms upstairs have hard wood floors as well the downstairs with the exception of the kitchen.

Type:
Single Family
Sq.Ft.:
1,818
Status:
Active
Beds:
4
Lot size:
0.72 Acres
Year built:
1875
Baths:
2.00
MLS#:
24061642
Subdivision:
Winsted

ADDITIONAL INFORMATION

Renovated to 4 Bedroom and 3 Full-bath home with 2028 SQFT, this stunning Colonial on Private Road a short walk to Highland Lake. This newly remodeled 1875 home seamlessly blends historic charm with modern amenities. Inside discover a spacious floor plan offering an abundance of natural light perfect for both entertaining and everyday living. The custom kitchen is a chef's dream featuring sleek quartz and waterfall counter-tops, gorgeous ceramic tile, high end stainless steel appliances and wine refrigerator. Every detail in this home has been carefully thought out adding the laundry on upper level, 3 full custom bathrooms, solid oak hardwood floors, and ample storage for comfort and flow. The upper level has a large primary with en-suite bathroom, ensuring privacy & relaxation. The 3rd bedroom can function as a home office, offering a peaceful & productive space with views of the Mountains. Equipped w/ energy-star rated systems this home has forced hot air w/ central a/c, Navien on demand hot water, google nest thermostats, city utilities water/sewer/natural gas for year round comfort and energy savings. Not only is this home move in ready, but its perfectly located near Highland Lake Beach, local parks and playgrounds. Commuting is a breeze with access to Route 8 for quick connections to nearby towns and Bradley Airport. Enjoy the charm & excitement of downtown Winsted with its boutiques, movie theater, fine dining, and public parks for a nice relaxing walk.

Type:
Single Family
Sq.Ft.:
1,277
Status:
Active
Beds:
3
Lot size:
1.3 Acres
Year built:
1940
Baths:
1.00
MLS#:
24059573
Subdivision:
Winsted

ADDITIONAL INFORMATION

Back on the market! Enjoy living in your own home nestled in the scenic Litchfield Hills in this newly renovated three-bedroom house with many updates: Refrigerator, range, microwave, dishwasher, and first floor washer/dryer less than a year old. Hot water heater 2023. Updated electrical 2024. Furnace serviced and updated with new burner 2024. 3 new exterior doors and 6 new windows. Enjoy the wood-burning stove in the family room, built-ins in the dining room, and storage shed out back. Conveniently located off Route 8 and close to Route 44 --easy commute into Hartford or Bradley International Airport. Close to shopping, restaurants, several parks, pristine lakes with boat launches, and walkable downtown Winchester. Northwest Community College is 4 minutes away and the art scene is up and coming. See it today!

Type:
Single Family
Sq.Ft.:
2,496
Status:
Active
Beds:
4
Lot size:
0.7 Acres
Year built:
1930
Baths:
3.00
MLS#:
24052635
Subdivision:
Winsted

ADDITIONAL INFORMATION

Lakefront Historic Architecture meets Modern Styling on private waterfront penninsula with 360' direct lake frontage! Split timber tudor architecture offers unique features - leaded glass, stone flooring, window seats, paneling and mouldings, brick and stone appointments. A stunning kitchen for folks who cook, charming diningroom with bar and window seat overlooking the waterfront, and spacious family room with granite fireplace with views in all directions. Sunroom with radiant heated stone flooring, extensive stone patios, pergola, gardens, terraces, sandy beach/swimming area. This is it!

Type:
Single Family
Sq.Ft.:
5,231
Status:
Active
Beds:
8
Lot size:
1.51 Acres
Year built:
1930
Baths:
5.00
MLS#:
24047556
Subdivision:
N/A

ADDITIONAL INFORMATION

Welcome to this spectacular Highland Lake estate, offering a unique blend of luxury & tranquility. Situated on 1.3 acres of level land, the property includes a large barn/garage capable of housing multiple cars, boats, & equipment. The main home boasts generously sized rooms w/ high ceilings, offering an open, airy feel throughout. The kitchen has been updated w/ hardwood cabinets, featuring updated appliances, a spacious eat-in area, & an oversized island perfect for meal prep & entertaining. The rest of the main floor is ideal for hosting guests, w/ expansive windows providing stunning views of Highland Lake from every angle. Step outside to a covered front porch, where you can take in breathtaking sunrise views over the water. The second floor is home to the huge Primary bedroom, complete w/ a recently remodeled full bath & two walk-in closets. Four additional spacious bedrooms share Jack & Jill bathrooms, & a second-floor summer porch offers a serene spot to enjoy the natural beauty of the lake. The third floor adds even more space, w/ three additional bedrooms & a full bath that could be updated to reflect your needs. Directly on the lake is a 1/4 acre lot w/ 150+/- ft of water frontage, you'll find a charming lakeside cottage that features a cozy fireplace, kitchenette, full bath, & wrap-around deck. Whether you're relaxing on the dock or enjoying the cottage's amenities, this entire property is perfect for experiencing the best of lakefront living.

Type:
Single Family
Sq.Ft.:
7,000
Status:
Active
Beds:
9
Lot size:
1.9 Acres
Year built:
2002
Baths:
6.00
MLS#:
24042374
Subdivision:
N/A

ADDITIONAL INFORMATION

This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into boating, jet skiing, swimming, and fishing right from your private dock, or simply unwind along the shoreline. As winter settles in, the lake becomes a playground for ice fishing, skating, and cozy fireside gatherings, making this a year-round sanctuary. With luxury finishes, a gourmet kitchen, and custom craftsmanship in the main home, plus a charming guest bungalow, this property is ideal for hosting family, friends, or even guests. Zoned for a bed and breakfast and featuring an extra subdividable lot, the estate also holds exciting potential for income generation or expansion. Whether you're envisioning a private retreat, an upscale B&B, or future development with a subdividable lot, this versatile property is the perfect setting for those seeking a dynamic, all-season lake life.

Type:
Single Family
Sq.Ft.:
3,404
Status:
Active
Beds:
5
Lot size:
2.09 Acres
Year built:
1975
Baths:
3.00
MLS#:
24042770
Subdivision:
N/A

ADDITIONAL INFORMATION

Welcome home! This inviting residence features an open, airy feel with abundant natural light from big windows and multiple skylights. The main level boasts solid hardwood floors and tiles, while the spacious eat-in kitchen, though older, is well-maintained and perfect for family meals. Enjoy three full bathrooms, a central vacuum system, and tons of storage space throughout. The primary bedroom is a cozy retreat with its own fireplace, and the large living room also includes a fireplace for added charm. Outside, you'll find a deck, mature plantings, flower beds, and a handy shed. With a big 2-car garage and a fantastic laundry room, this home has everything you need! This property is being sold As-Is. All inspections for informational purposes only.

Type:
Single Family
Sq.Ft.:
1,781
Status:
Active
Beds:
4
Lot size:
0.62 Acres
Year built:
1904
Baths:
2.00
MLS#:
24041356
Subdivision:
Winsted

ADDITIONAL INFORMATION

Stunning Lake Vistas! Have you been dreaming of a lake view and a property that is Special, Unique and TURN KEY? Fifty feet of waterfront property is included with boat dock and lift for lake enthusiasts! Nestled across from the serene First Bay, this beautifully renovated two-family home can be used as a single family and offers breathtaking water views and modern comforts. Perfect as a family retreat or an income-generating property, the home is fully renovated with upscale finishes throughout and boasts central air, newer appliances, windows, siding, and high-efficiency propane-fueled furnaces. Gorgeous details throughout make this a truly exceptional property. On the first floor, you'll find a rustic custom kitchen w granite, upgraded appliances (sub zero refrigerator and bevg fridge, gas range, dishwasher), a full bathroom w marble and walk-in shower, two spacious bedrooms, and a large family room w French doors leading to a covered wrap around porch to enjoy that view! The second floor unit features a kitchenette with fridge, dishwasher, and range, dining room/office, two bedrooms, and a family room with sliders to a covered porch offering the same amazing landscape! Additional highlights include an oversized two-car detached garage and carport, hot tub(sold as is), level yard area, and side deck. This home is situated just across the street from the water, providing easy access to all lake activities. Rustic yet Upscale! A RARE FIND!

Type:
Single Family
Sq.Ft.:
2,664
Status:
Active
Beds:
3
Lot size:
0.61 Acres
Year built:
2024
Baths:
3.00
MLS#:
24022821
Subdivision:
Winchester Center

ADDITIONAL INFORMATION

Build your DREAM home! Largest lot available on the lake with great views and parking! Will build to suite. Don't miss this wonderful opportunity! WELL IS LOT CORNER at Forest Ave FRONTAGES ARE MARKED IN RED. +-a2 map and topo in documents.

Type:
Single Family
Sq.Ft.:
2,687
Status:
Active
Beds:
7
Lot size:
1.63 Acres
Year built:
1890
Baths:
4.00
MLS#:
24024787
Subdivision:
Sucker Brook

ADDITIONAL INFORMATION

Welcome to Strong Island, a waterfront retreat on Highland Lake. The clean waters of Highland Lake in the town of Winchester in Litchfield County surround this 1.6 acres island. History abounds for this property as the original house dates back to 1890. There were significant alterations made in 1920 that added several rooms, a boat house, a barn and porch. Babe Ruth made several trips to Strong Island for his weekends and vacations away from NYC. Strong Island is one of the largest islands on Highland Lake and has the best views. The position of this island give it the longest view of the lake on a North view and also on an Easterly view. The position of the main house on the island, the various docks, piers and out buildings make this property unable to be duplicated today. Strong Island is a trophy property that needs some polishing, but incredible in so many ways.

Type:
Single Family
Sq.Ft.:
1,608
Status:
Active
Beds:
3
Lot size:
0.22 Acres
Year built:
1917
Baths:
3.00
MLS#:
24026928
Subdivision:
Winsted

ADDITIONAL INFORMATION

Great opportunity for Investors. This is a total renovation project being offered to serious qualified buyers only. 1608 sqft incl. 3 bedroom and 2.5 baths, dining and living room open concept, patio in backyard and water feature in front yard. Interior mix of tiled and HW floors. Located within walking distance downtown Winsted, Northwestern Community College, Whiting Mills building home to various artists, craftsman, retail shops. Property has amazing opportunities to rejuvenate this New England colonial back to its unique original charm once again. Perfect setting for an Airbnb rental, weekender or simply a year-round home. Just minutes away to beautiful lakes, rivers, skiing, various unique eateries, cultural events and endless outdoor activities. Just minutes away to beautiful Highland Lake, fishing, kayaking, bicycling and walking trails and endless adventures to explore. Cash or 203K Renovation Loan financing.

Type:
Single Family
Sq.Ft.:
2,135
Status:
Active
Beds:
3
Lot size:
3.46 Acres
Year built:
2023
Baths:
3.00
MLS#:
170551066
Subdivision:
N/A

ADDITIONAL INFORMATION

Beautiful custom built gem situated on a private site with a stream! Bright, sunny open floor plan with 3 bedrooms, 2.5 baths, great bonus room. Gleaming hardwood floors thru-out, granite tops, stone/marble baths, walk up attic. Large deck off kitchen. Don't miss this incredible opportunity!

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Davis E. Owen, Sr., License REB.0754414, Xome CT LLC, License REB.0790146 , Davis.Owen@xome.com, 844-400-XOME (9663), 2083 Main Street, Stratford, CT 06615

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Winchester Real Estate

The median home value in Winchester, CT is $260,000. This is lower than the county median home value of $345,200. The national median home value is $338,100. The average price of homes sold in Winchester, CT is $260,000. Approximately 51.37% of Winchester homes are owned, compared to 34.14% rented, while 14.49% are vacant. Winchester real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Winchester real estate agent to arrange a tour today!

Winchester, Connecticut has a population of 10,335. Winchester is less family-centric than the surrounding county with 20.73% of the households containing married families with children. The county average for households married with children is 26.17%.

The median household income in Winchester, Connecticut is $65,537. The median household income for the surrounding county is $84,797 compared to the national median of $69,021. The median age of people living in Winchester is 50.7 years.

Winchester Weather

The average high temperature in July is 80.7 degrees, with an average low temperature in January of 13.6 degrees. The average rainfall is approximately 52.3 inches per year, with 52.6 inches of snow per year.

Winchester Real Estate Market Conditions

  • Median sales price

    $260,000
    14.1% change since last quarter
  • # Active listings

    41
    30-day change

Winchester Schools and Demographics

Education near Winchester, CT

Metric City County
High School Graduates 93.76 93.89
College Degree - 2 year 11.55 9.19
College Degree - 4 year 27.21 36.19
Graduate Degree 8.81 11.56
Expenditures per Student 26,218 26,218
Students per Teacher 11.5 11.5

Elementary Schools near Winchester, CT

School Grades Students P/T Ratio ZIP
Batcheller Early Education Center PK - 01 186 12.6 06098
Botelle Elementary School PK - 06 115 12 06058
East School KG - 05 361 12.9 06790
Forbes School KG - 05 373 11 06790
Goshen Center School KG - 06 150 10.7 06756
Mary P. Hinsdale School 02 - 04 241 11.9 06098
Torringford School KG - 05 615 13.4 06790
Vogel-Wetmore/Outreach PREK PK - PK 7 06790

Middle Schools near Winchester, CT

School Grades Students P/T Ratio ZIP
Northwestern Regional Middle School 07 - 08 332 10.9 06098
Pearson Middle School 05 - 08 149 11.5 06098
Torrington Middle School 06 - 08 1,012 13.1 06790

High Schools near Winchester, CT

School Grades Students P/T Ratio ZIP
Explorations 09 - 12 88 9 06098
Northwestern Regional High School 09 - 12 693 12.9 06098
The Gilbert School 07 - 12 552 11.8 06098
Torrington High School 09 - 12 1,003 12.4 06790

Ungraded Schools near Winchester, CT

School Grades Students P/T Ratio ZIP
* Migeon Academy 09 - 12 12 06790
Batcheller - Bridges 1 UG - UG 0 06098
Connecticut Mental Health Center UG - UG 0 06790
Intensive Learning Program UG - UG 0 06098
Links 06 - 12 13 13 06098