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104 Windham Center Rd, Windham
$577,875
4 Beds ⋅ 4 Baths ⋅ 24113837 MLS
Elegant, Greek Revival Colonial home in historic Windham Center completely remodeled in 2005 by New England Design. This four bedroom, 3 full and one half bath features the charm and craftsmanship of bygone days with all of the convenience of modern day living. Three fireplaces, granite and marble flooring, graceful touches such as mahogany paneling in the study, bookcases, built ins, moldings, wainscoting, window seats, French doors, high ceilings, and very private patio with gardens are some of the specialties of this home. The house sits on a generous 6.89 acre parcel and is augmented by an adjoining separate 4.41 acre parcel for a total of 11.3 acres of property. A separate three car barn with workshop and second floor storage is accessed off of Mullen Hill Rd. This exceptional home offers the owners easy access to Willimantic for shopping or work, ECSU, UConn, Route 32 to the CT or RI shore, Providence or Boston, or access to Route 6 and Hartford and points north and south.

104 Windham Center Rd, Windham

37 Manners Ave, Windham
$550,000
8 Beds ⋅ 5 Baths ⋅ 24176666 MLS
HIGHEST and BEST due midnight 6/8. What if your next investment came with an indoor pool and was completely furnished? 37 Manners Ave is not your average multifamily. This custom-built 3-family sits on a spacious lot in Willimantic with additional finished spaces, giving owners over 4,800 square feet to work with. Two 2-car garages, a spacious yard, a wide patio, and a private indoor pool with cathedral wood-beam ceilings and skylights that round out this property that makes this THE special opportunity you've been dreaming of. And, the numbers work great. At market rent this property projects strong monthly cash flow and an appealing cap rate from day one. All total expenses were only $23k last year. Plus, the location just couldn't be better. Minutes from UConn, ECSU, Foxwoods, and Mohegan Sun. And the best part? It's walkable to downtown Willimantic and all of it's parks, restaurants, community center, concerts on the green, and 3rd Thursday Street Festivals. Whether you are a Multigenerational family looking for a space for everyone, a Hospitality entrepreneur ready to host experiences unlike any other, or a buy-and-hold investor that wants to live large while you grow your portfolio, 37 Manners Ave is the perfect pen with which to write your next chapter. This property has the space, the income, and the wow factor to make it all real. They say you only live once. Get the pool

37 Manners Ave, Windham

6 Zoldak Dr, Windham
$520,000
3 Beds ⋅ 2 Baths ⋅ 24202685 MLS
**Open House Cancelled for Sunday Sept 6****Welcome to this beautifully maintained open-concept ranch, built in 2008 and situated on a private, level 3.6-acre lot. Offering 3 bedrooms and 2 full bathrooms, this home combines modern comfort with spacious single-level living. The bright, open floor plan features gleaming hardwood floors, tray and cathedral ceilings and two gas fireplaces. The kitchen boasts stainless steel appliances, granite countertops, tall cabinets and a convenient desk area. You'll find a seamless flow between the kitchen, dining, and living areas, making it ideal for both everyday living and entertaining. A sun-filled sunroom provides the perfect spot to relax and enjoy views of the surrounding property, while the deck offers additional outdoor living space for gatherings or peaceful mornings. Car enthusiasts, hobbyists, and those in need of extra storage will appreciate the impressive 5-car garage capacity, including an attached 3-car garage and a detached 2-car garage. The expansive 2100 sq ft basement presents excellent potential for future finishing with a bath location already plumbed in. The possibilities are endless to create additional living space, a recreation room, home gym, or workshop. Don't miss this opportunity to own a move-in-ready ranch with room to grow both inside and out!

6 Zoldak Dr, Windham

3 North Rd, Windham
$505,000
4 Beds ⋅ 4 Baths ⋅ 24160899 MLS
It's BACK!! This is your moment. There's something about the Windham Center green that just feels like home. Whether it's the people, the library, or the history, the moment you arrive, you know that it's special. And the standout on the Green? 3 North Road. Built in 1885 and loved every year since, it is the kind of place that has passerbys slowing down to take it all in. Step inside and you will understand why. Coffered ceilings, rich period woodwork, and sun-filled rooms that feel both grand and genuine. With 3,639 square feet, four bedrooms, and four bathrooms, there's room for everyone. The master bedroom shines as the primary suite. A proper retreat with a modern bath and great closet space. The finished third-floor attic space is whatever you want it to be: office, art studio, playroom, or a place to make your music from the top of the town. The custom kitchen was made for people who love to gather with friends and family alike. Warming closets for their coats, a wall oven for accessible baking and a gorgeous granite topped island. Host holiday dinners, weekend brunches, or game nights that turn into midnight conversations. Outside, a koi pond and perennial garden are pure natural therapy. Fire up the grill, let the little ones run, and sit on the porch with a drink and watch the green do its thing. Three-bay garage, first-floor laundry, new septic tank, and a layout perfect for an in-law suite, ADU, or bed and breakfast. Close to so many great places!

3 North Rd, Windham

6 Autumn Rdg, Windham
$500,000
2 Beds ⋅ 2 Baths ⋅ 24191550 MLS
Experience exceptional craftsmanship in this magnificent timber frame home, thoughtfully designed with quality, comfort, and energy efficiency in mind. The stunning great room features soaring ceilings and an open-concept layout that flows seamlessly into the dining area and custom kitchen, creating an ideal space for everyday living and entertaining. A cozy propane stove adds warmth and ambiance during the winter months. Constructed with Structural Insulated Panels (SIPs) and built with meticulous attention to detail, this home offers outstanding energy performance. Additional features include radiant oil-fired underfloor heating, indirect hot water, an energy recovery ventilator (ERV), quarter-sawn wood flooring, and beautifully crafted custom kitchen cabinetry. Situated on a level, open cul-de-sac lot, the property offers both privacy and space to enjoy the outdoors. An attached screened gazebo provides the perfect setting for relaxing, dining, or entertaining while enjoying the fresh air in comfort. This is an ideal home for the discerning buyer, with quality and efficiency that is at the edge of building technology.

6 Autumn Rdg, Windham

4 Main St, Windham
$485,000
9 Beds ⋅ 5 Baths ⋅ 24099416 MLS
Terrific Investment Opportunity! Don't miss this rare chance to own a well-maintained multi-unit property with strong income potential. The main house features a spacious layout with 5 bedrooms, ideal for large households or rental flexibility. Behind the main home, you'll find a separate 2-bedroom unit, perfect for extended family or additional rental income. Additionally, there's a third unit-a charming ranch-style 2-bedroom apartment located above a detached 3-car garage. Key features include: Whole-house generator for the main home. Newer boiler and hot water heater. New roof. Plenty of off-street parking. Whether you're a seasoned investor or just getting started, this property is a fantastic opportunity to build wealth through real estate. Schedule your showing today!

4 Main St, Windham

19 Zoldak Dr, Windham
$470,000
4 Beds ⋅ 3 Baths ⋅ 24185158 MLS
A Wonderful opportunity to own a BRAND NEW and quality constructed home in Windham, located on a newer cul-de-sac street on 2.77 acres of land. The home will soon ready for a new owner to move right in and enjoy. This is a spacious FOUR bedroom and THREE FULL bath, Contemporary Raised Ranch, consisting of 1890 square feet of living space. The home has an open concept with vaulted ceilings and hardwood floors in the upper living area and kitchen. The kitchen is fully applianced, with granite counter tops and a center island. The four bedrooms are spacious and the home has the flexibility for the primary bedroom to be on either the upper of lower level. There is a huge two-car garage, exterior deck, energy efficient warm air heat, central air, and much more. Do not miss the opportunity to own beautiful brand new home!!!.

19 Zoldak Dr, Windham

37 Tuckie Rd, Windham
$470,000
3 Beds ⋅ 3 Baths ⋅ 24180372 MLS
Welcome to your dream home! Nestled on a sprawling, flat acre lot, this beautiful home offers field views and stunning sunsets that will captivate you. Step inside to discover a bright and airy space with room for all! Hardwoods grace the first floor which offers a large kitchen perfect for cooking up a storm which flows seamlessly into the eat in kitchen and living room. The dining room offers that extra space for entertaining & a half bath w/laundry completes the first floor. Upstairs is a bonus room, perfect for a home office or playroom, Along with a primary bedroom with en-suite full bath and 2 additional bedrooms with another full bath. Outside, unwind on the paver patio, complete with a built-in fire pit - ideal for cozy gatherings under the stars. Don't miss this perfect blend of comfort, style, and outdoor bliss. Close to shopping, ECSU, eateries, golf and more!

37 Tuckie Rd, Windham

97 Bass Rd, Windham
$470,000
4 Beds ⋅ 3 Baths ⋅ 24149101 MLS
Welcome to this beautifully updated colonial, set on 2.5 acres in a quiet country setting. A spacious entryway introduces the open, flowing main level floor plan, creating an inviting sense of space from the moment you step inside. The elegant eat-in kitchen features granite countertops, newer appliances, stylish lighting, and stunning flooring that carries throughout the first floor. The flexible layout allows you to tailor the space to your lifestyle-whether you prefer a large living room, a combined play area, or a mix of both. On the opposite side of the center staircase, you'll find a room perfect for a formal dining area, family room, or home office. Two sets of French doors open onto the back deck, offering views of the fenced in backyard surrounded by woods - great for pets and play! The gentle sound of the babbling brook along the property adds a serene touch to your outdoor living experience. Upstairs are 4 generously sized bedrooms. The primary suite features an updated private bath and two large walk-in closets. Three additional bedrooms share a hallway full bath with a tub/shower and a convenient linen closet. The walk-up attic and a full unfinished walkout lower level provide tons of storage opportunity. The laundry area and bonus sauna are also located on the lower level. The property also includes a large 2-car detached garage and a storage shed/dog kennel.

97 Bass Rd, Windham

5 Insalaco Dr, Windham
$465,000
4 Beds ⋅ 2 Baths ⋅ 24154505 MLS
Welcome to 5 Insalaco Drive in Windham - a stunning, meticulously maintained 4-bedroom, 2-bath ranch style home located in a desirable countryside neighborhood, just minutes from Windham Center, Windham Shetucket Pickleball Park, Windham Fish & Game Club, and Mansfield Hollow State Park. This move-in ready home features hardwood floors throughout, large bedrooms with ample closet space, and an open-concept gourmet kitchen with granite countertops, shaker solid wood cabinets, under-cabinet lighting, a large pantry, and stainless steel LG appliances. The kitchen opens to the living area with an electric fireplace and sliding glass doors leading to a custom covered deck with built-in cabinets and recessed lighting - perfect for entertaining or enjoying the flat, professionally landscaped backyard with fire pit and shed for storage. On the lower level you will find a large immaculate basement with walkout and custom brick finishings, great for storage or recreational play. Additional upgrades include a radon mitigation system, water softener with carbon filter, Carlin oil burner, Therma-Flow 30-gallon oil-fired water heater, septic replacement, new well pump, King pellet stove, electric fireplace insert, leaf gutter guards, new driveway, and new windows. The oversized attached 2-car garage features high ceilings and a workbench. This home offers the perfect combination of modern updates, comfort, and convenience - all thoughtfully maintained and ready for its next chapter

5 Insalaco Dr, Windham

119 Brooklyn Tpke, Windham
$450,000
4 Beds ⋅ 3 Baths ⋅ 24126264 MLS
HIGHEST & BEST BY MONDAY, SEP 22 AT 1PM. Sellers reserve the right to accept an offer at any time. Move-in ready with in-law!! Major upgrades in 2024 include: top of the line Buderus heating system, new roof, new siding, and more. The main house offers 3 bedrooms, an open, updated kitchen, central air, pellet stove for secondary source of heat and additional 500 sq feet of finished lower-level space with endless possibilities. The brand new in-law apartment features a private entrance complete with a designated bedroom, kitchen, bathroom, living area, covered porch, in-unit laundry and ductless cooling - perfect for multi-generational living or guests. Enjoy outdoor living with a deck, patio and gardens designed for entertaining. All this in a quiet, serene location just minutes to shopping, dining, schools and more. This beautifully landscaped corner lot has it all! Don't miss out on this gem!

119 Brooklyn Tpke, Windham

121 Insalaco Dr, Windham
$447,000
3 Beds ⋅ 3 Baths ⋅ 24153956 MLS
Perched up on this scenic lot at the end of a cut-de-sac sits this beautiful dormered cape ready to be moved into and enjoyed! You will love the views from the full front porch as well as the privacy of the back deck overlooking farmlands. Interior features an open floor plan with eat-in kitchen to living room with a gas fireplace. Kitchen boasts granite countertops, and stainless steel appliances. The first floor is highlighted by 9' ceilings giving a more elegant feel. 2nd floor has a full primary bedroom suite with walk-in closet as well as a full bath. The 23x19 rec room is currently being utilized as an office/playroom but could easily be transitioned to a 4th bedroom. Partially finished lower level adds to additional sq footage giving this home plenty of living space. A newer Buderus heating system has been installed, as well as central air/heat pump allowing for flexibility in heating! Exterior features a large storage shed, paved driveway, and mature landscaping.

121 Insalaco Dr, Windham

337 S Windham Rd, Windham
$440,000
4 Beds ⋅ 3 Baths ⋅ 24117815 MLS
This charming four-bedroom, two-and-a-half-bathroom home offers 2,905 square feet of comfortable living space that offers both style and functionality. The thoughtfully designed layout provides ample room for daily life and entertaining, with well-appointed bedrooms including a spacious primary bedroom that serves as your personal retreat. The kitchen becomes the heart of the home where morning coffee rituals and evening dinner preparations unfold naturally. Multiple bathrooms ensure convenience during busy mornings, while the additional half-bath proves invaluable when hosting guests. Living areas flow seamlessly, creating spaces where family movie nights and quiet reading sessions coexist beautifully. Located in a peaceful Willimantic neighborhood, this property places you within easy reach of local amenities and recreational opportunities. The nearby Windham Fish and Game Club offers outdoor enthusiasts a chance to connect with nature, while Bob's Windham IGA provides convenient grocery shopping just minutes away. Cultural enrichment awaits at the Arts at the Capitol Theater, bringing entertainment and community events to your doorstep. The surrounding area balances small-town charm with practical accessibility to larger metropolitan areas. This home represents an opportunity to establish roots in a community that values both tranquility and convenience. Don't miss your opportunity to make this your home today! Sold As-Is.

337 S Windham Rd, Windham

74 Pigeon Rd, Windham
$435,000
4 Beds ⋅ 3 Baths ⋅ 24172139 MLS
This is the one you've been waiting for! Offered for the first time in 38 years, this lovingly maintained home blends thoughtful updates with charming retro touches - welcome to 74 Pigeon Road! Filled with natural light, the sprawling layout features 4 bedrooms, including a sunken primary suite with walk-in closet on the second floor, and 2.5 baths. The updated kitchen is a total standout, complete with a breakfast nook, while the first floor also offers a formal dining room, spacious office, convenient laundry, living room, and a sunken family room perfect for relaxing or entertaining. Enjoy additional highlights like central vacuum, a newer roof and boiler, newly paved driveway, and a finished lower level ideal for a rec room, hobby, or workshop space. Unwind year-round in the dedicated hot tub room, or step outside to a beautiful stone patio overlooking the manicured yard. Set on a cul-de-sac street in an established neighborhood, this property offers a convenient location that is walkable to downtown where you'll find local shops, dining, and entertainment, and with easy access to nearby ECSU and major routes, and just 15 minutes from UConn. A rare opportunity to own a very well-cared-for home with space, character, and versatility.

74 Pigeon Rd, Windham

19 Oakwood Dr, Windham
$435,000
4 Beds ⋅ 3 Baths ⋅ 24127357 MLS
Introducing 19 Oakwood Drive, a charming Colonial set on a private 1.6-acre corner lot. This well-loved home has been carefully maintained and offers both comfort and space. Inside, you will find a warm brick fireplace in the living room, a bright eat-in kitchen, and a large screened-in porch overlooking the expansive backyard. The main floor features a generously sized primary bedroom with a full bath, including a brand-new tiled walk-in shower. Upstairs, there are four additional good sized bedrooms and a full bathroom, providing plenty of room for family and guests. The home offers abundant storage throughout, including a full unfinished basement and a two-car attached garage. Outdoor living is enhanced with a deck and a working hot tub (being sold as-is). With its combination of classic charm, functional living space, and a spacious lot, this property is a must-see and is not expected to last long. Schedule your private showing today.

19 Oakwood Dr, Windham

33 Jennings Ln, Windham
$432,000
4 Beds ⋅ 2 Baths ⋅ 24190853 MLS
Completely renovated from top to bottom, this move-in ready raised ranch sits on 2 private acres and offers the perfect blend of modern farmhouse design, quality craftsmanship, and today's most desirable upgrades. With approximately 2,000 square feet of beautifully finished living space, this home features 4 bedrooms, plus an office/recreation room, 2 full bathrooms, and a finished walkout lower level with a spacious entertainment room. The heart of the home is the stunning designer kitchen, thoughtfully remodeled with quartz countertops, a timeless tiled backsplash, brand-new stainless-steel appliances, and an expansive peninsula offering additional seating, prep space, and effortless entertaining. A dedicated coffee bar adds both charm and functionality, while the abundance of countertop space and cabinetry provides exceptional storage. The kitchen flows seamlessly into the dining area, where French doors open to the insulated four-season porch, creating the perfect place to enjoy your morning coffee while overlooking the private backyard. Large windows throughout the home fill every room with an abundance of natural light. Just off the kitchen, you'll find a beautifully renovated mudroom that connects the home to the attached two-car garage, offering a stylish and practical transition between the garage and the main living area.

33 Jennings Ln, Windham

44 Ballamahack Rd, Windham
$430,000
3 Beds ⋅ 1 Baths ⋅ 24167529 MLS
A rare offering, this beautifully preserved circa 1766 Cape-style residence blends timeless New England character with thoughtful modern updates on just under 4 picturesque acres in Connecticut's Quiet Corner. Rich in historic detail, the home showcases wide plank floors, exposed hand-hewn beams, decorative wood paneling, and three fireplaces with gas inserts that create warmth and ambiance throughout. Offering 1,988 sq ft, the home includes 3 bedrooms, 1 bath, and versatile bonus space ideal for office, guest, or hobby use. Significant improvements include updated electrical, plumbing, insulation, and reglazed windows. The primary bedroom features an updated closet, with opportunity for future bath expansion. Outside, multiple patios provide inviting spaces for entertaining and outdoor enjoyment, surrounded by historic stonewalls, gated fencing, and sweeping open field views. A renovated historic barn serves as a standout feature of the property, offering exceptional flexibility for workshop, studio, storage, entertaining, or creative pursuits, complemented by a rear barn extension and accessory outbuilding for additional storage and utility. Not located in a historic district, providing flexibility without restriction. A truly special opportunity to own an architecturally significant antique home offering privacy, character, acreage, and unmatched charm in a serene setting.

44 Ballamahack Rd, Windham

272 Prospect St, Windham
$420,750
5 Beds ⋅ 3 Baths ⋅ 24179602 MLS
Step back in time in this majestic REMODELED 5-Bedroom Queen Anne-style Victorian home complete with wrap-around porch, gorgeous stone pathway gardens, soaring ceilings, hardwood floors, original woodwork, AND a beautifully remodeled kitchen!! The George Tiffany House circa 1890 offers plenty of rich history and architectural character and is on the National Registery of Historic Places. The interior has been lovingly updated/restored over the past 3 years, while preserving the special character of this gorgeous home. All antique windows have been reglazed and have storm windows for energy efficiency. Steam radiator heat with natural gas boiler. The huge walk-up partially-finished attic could be easily completed and made into a wonderful artist space or rec/game area. And for those who are looking for a workshop...There are TWO large connected rooms in the basement with tall ceilings for your woodworking or hobby pleasure, in addition to other storage space accessible from both inside the home and though the back garage bay. Excellent location to ECSU and restaurants and amenities downtown. Come see what this beautiful home has to offer!! Additional photos to follow.

272 Prospect St, Windham

4 Aspen Pl, Windham
$413,000
3 Beds ⋅ 2 Baths ⋅ 24197724 MLS
Welcome to this beautifully maintained ranch home offering true one level living and peace of mind with major recent updates, including a newer central air system and convenient efficient propane heating system for reliable year-round comfort. Clean, functional, and easy to navigate, this home is ideal for buyers seeking a low maintenance lifestyle or planning ahead for aging in place. Situated in a desirable residential neighborhood with no HOA fees, this move in ready property is designed for long term convenience. The expansive backyard provides plenty of usable outdoor space for gardening, pets, play, or future outdoor entertaining. Inside, you'll find a bright and inviting interior with a practical open concept layout. The spacious kitchen serves as the heart of the home, flowing seamlessly into both the dining area and living room, creating an ideal space for everyday living and gatherings. The attached one car garage offers easy access to the kitchen, making unloading groceries effortless, while also providing a convenient mudroom area and laundry space with convenient laundry space. The formal front entry welcomes you with unobstructed views of the main living area, enhancing the home's spacious feel. Two bedrooms and a full bath are located on one side of the home, while the private primary suite occupies the opposite wing, featuring a generous walk-in closet and large full bath.

4 Aspen Pl, Windham

66 Lynwood Dr, Windham
$410,000
3 Beds ⋅ 2 Baths ⋅ 24175279 MLS
Welcome to this ranch home in excellent condition offering true one level living and worry free with a new HVAC system for heat and central air, as well as a new hot water heater - both for efficient and reliable comfort. The home is clean, functional, and easy to navigate - perfect for buyers seeking a low maintenance lifestyle or planning ahead for aging in place. Located in a residential area with no HOA fees, this property is move in ready and designed for long term convenience. An expansive backyard allows for plenty of usable outdoor space for gardening, pets, and play. Inside, you'll find a bright, clean interior with a practical flow. The heart of the home features an open concept where the large kitchen is open to both the dining area and living room. Bringing in groceries from the attached 1-car garage is a breeze with just a few steps into the kitchen. This everyday entry also provides a mudroom area and laundry (new units installed in 2025). The formal front door entry gives a spacious feel when entering with unobstructed views of the main living area. To the left are two bedrooms and full bath in between. On the other side of the home is a primary bedroom suite complete with a roomy walk-in closet and large full bath. The walkout lower level is a bonus surprise. A glass slider and two full-sized windows brighten up this level offering future expansion capabilities (possible in-law/apartment). Currently being used for a second laundry area and storage.

66 Lynwood Dr, Windham

128 Machine Shop Hill Rd, Windham
$395,000
3 Beds ⋅ 2 Baths ⋅ 24159990 MLS
Charming New England Cape offering the perfect blend of timeless character and modern updates. Set on a nice-sized lot with a private yard, this beautifully maintained home features thoughtful renovations while preserving its original charm. The bright updated kitchen showcases white cabinetry, granite countertops, new stainless steel appliances, and fresh paint, creating a clean and inviting space for everyday living. The home also features fully renovated bathrooms and fresh paint throughout. A standout feature is the spacious family room with vaulted ceilings, built-in window seats, and a cozy wood-burning stove, providing a warm and inviting gathering space. Classic New England character continues throughout the home with a fireplace and charming original details. The layout offers flexibility with a first-floor ensuite bedroom, while the second level features two additional bedrooms and a second full bath. Additional highlights include a newer roof, newer vinyl siding, and a two-car garage. Step outside to enjoy the private backyard with patio and deck, perfect for relaxing or entertaining. This beautifully updated Cape combines historic charm with modern comfort, offering a warm and welcoming home in a peaceful South Windham setting. Interior Photos and floor plans will be available soon -

128 Machine Shop Hill Rd, Windham

63 Beacon Rd, Windham
$390,000
4 Beds ⋅ 1 Baths ⋅ 24179460 MLS
Welcome to your own private oasis! This beautifully maintained, sunny, move in ready home perfectly showcases true pride of ownership. Step inside to discover a bright and airy open floor plan on the main level. At the heart of the home is an updated kitchen, complete with newer granite countertops and appliances. The living space extends to the lower level, where you will find an additional finished 600+ Sq.Ft. featuring a spacious family room, perfect for a home office, or additional living space. Continuing outside onto the gorgeous, meticulously landscaped lot. Surrounded by lush lawns, vibrant plants, and flourishing garden spaces, this yard is a nature lover's dream. Relax on the shaded porch or step out onto the open deck, both of which offer peaceful views of your private backyard retreat. The centerpiece of this outdoor haven is a beautiful, privately set in ground pool with a newer lining, pump, and stairs, promising endless summer fun and relaxation. Adding to your peace of mind will be a brand new septic system, ensuring worry free living for years to come. Situated in a convenient location, this property offers a short commute to Eastern Connecticut State University, making it as practical as it is charming. Schedule your viewing today and prepare to fall in love!

63 Beacon Rd, Windham

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