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$350,000
3 Beds 2 Baths 24104640 MLS
Your next project starts here at 306 Upper Grassy Hill. Opportunity knocks in the charming town of Woodbury with this 3-bedroom, 2 full bath home packed with potential and ready for its next chapter. Situated on a generous 1.5-acre lot, this property offers plenty of space, privacy, and the chance to build some serious sweat equity. Inside, you'll find hardwood floors, a spacious sunroom surrounded by sliding glass doors, and a rare double deck, accessible from both the primary and second bedroom, perfect for enjoying the peaceful outdoor setting with elevated views of the property. Additional highlights include an updated oil tank and furnace, giving you a head start on mechanical upgrades. Whether you're looking to renovate and make it your own, flip for resale, or add to your investment portfolio, Upper Grassy Hill offers a solid foundation with endless possibilities. Don't miss this opportunity to create something special in a sought-after location!

306 Upper Grassy Hill, Woodbury

$347,000
3 Beds 3 Baths 24156207 MLS Woodlake BLDG.
New Price-Point on this lovely upscale residence! Don't miss the opportunity for a vacation at home "Woodlake Life Style" Each room is thoughtfully purposed and decorated with classy features.A spacious "open" concept kitchen includes "Corian" countertops. Cherry toned flooring adds a warm welcome to the first floor, as does the working fireplace. The 1st., floor powder room is oversized & updated. Upstairs, the primary bedroom bath is thoughtfully renovated: notice the addition of the "closet system". You will also note the convenient feature of the laundry - in close proximity to the primary bedroom. The Lower Level is finished and provides ample storage. The garage is partitioned from the other garage units. You will love exploring Woodbury and all it has to offer. Recently voted CT's Best Small Town by The Boston Globe and Reader's Digest. There are Restaurants galore, many featuring farm to table cuisine. Woodbury is home to two Main Street Greens & lovely period homes. Woodbury is part of CT's Antique and wine trail. Shop Boutiques & Garden Ctrs. Hollow Park, Flanders Nature Ctr., Learning & Performing Art Centers, The Glebe House Museum & hiking trails, are just a few suggestions that make Woodbury Special. Close to private schools. The Commute east or west on I-84 is easy! Its time to plan your 2026 move! 2025 New Heat Pump and Attic "Blown-in" insulation, keeps this residence toasty warm. Stay tuned for info on Woodlake's Community Room Reopening!plan your tour soo

2 S Mdws Unit 2, Woodbury

$345,000
4 Beds 2 Baths 24060030 MLS
OWNER OCCUPANT BUYERS RECEIVE PRIORITY CONSIDERATION AND MAY PURCHASE THIS PROPERTY IMMEDIATELY BY SUBMITTING NAR STANDARD AS-IS/ WHERE-IS CONTRACT. REO PROPERTY BEING SOLD SUBJECT TO "FIRST LOOK" PERIOD IN COOPERATION WITH HUD HVLS PROGRAM. ELIGIBLE NON-PROFITS AND GOVERNMENT ENTITIES MAY SUBMIT "NOTICE OF INTEREST" FOR DUE DILIGENCE REQUEST AND "NOTICE OF INTENT TO PURCHASE" PRIOR TO SALES CONTRACT. SEE ADDITIONAL ADDENDUM ATTACHED. This charming ranch is located in a great area - atop of upper grassy on the Roxbury border. This brick Ranch offers a great layout with 4 bedrooms, 2 baths and tons of space. Walk out lower level. Detached 1 car garage with storage. Beautiful secluded property and excellent location.

220 Upper Grassy Hill, Woodbury

$340,000
3 Beds 3 Baths 24125065 MLS Condos At Woodlake BLDG.
Welcome to Woodlake! This spacious 3-bedroom, 3-full-bath townhouse offers a flexible layout, abundant natural light, and multiple outdoor spaces to enjoy. The main level features a bright living room with sliders to a large deck, creating the perfect indoor-outdoor flow. The kitchen includes ample cabinetry, an eat-in dining area, and its own slider to the back of the home that offers a brand new stone patio for additional outdoor living. Also on this level you will find a generous bedroom with a walk-in closet and to finish it off is a full bathroom, ideal for guests or main-level living. Upstairs, you'll find two additional generously sized bedrooms, including a primary suite with a full tub/shower bath and the ability to have a walk-in closet. The third full bathroom is also found on this level for use by the additional bedroom. A convenient laundry nook completes this spacious upper level. The lowest level provides a welcoming entrance and ample storage space with additional potential for a bonus space or gym. Set in the desirable Woodlake community, residents enjoy walking trails, tennis courts, ponds for fishing, kayaking etc., and a clubhouse, all within minutes of Woodbury's vibrant town center, shops, and restaurants. With easy access to I-84, this home blends comfort, convenience, and community in one wonderful package.

4 Clubhouse Dr Unit 4, Woodbury

$335,000
2 Beds 2 Baths 24143427 MLS
Welcome to Sweet River Cottage, a charming riverside retreat offering the perfect blend of comfort, character, and natural beauty. This inviting 2-3 bedroom, 2 full bath home sits just steps from the water's edge, providing peaceful views and the soothing sound of the river year-round. Inside, you'll find a warm and welcoming eat-in kitchen, ideal for casual meals or gathering with friends. Enjoy the newly painted deck just off of the kitchen and overlooking these lovely views. The cozy living room features a wood stove, creating the perfect ambiance for cooler evenings and adding to the home's classic charm. Flexible bedroom spaces allow for a guest room, home office, or additional living area-whatever suits your lifestyle. Whether you're seeking a weekend getaway or a full-time haven, Sweet River Cottage offers tranquility, character, and an unbeatable riverside setting. Come experience the magic of cottage living. Perfect for first time home buyers or those wanting to scale down. This home is pristine and convenient to town.

10 Hazel Plain Rd, Woodbury

$330,000
3 Beds 3 Baths 24072490 MLS Woodlake BLDG.
Woodlake in Woodbury an easy place to live in a great community. This three bedroom two full and one-half bath was built in 1980 and is ready for a new homeowner. End unit with plenty of light and a beautiful deck. The flooring is a combination of tile and carpet, and the floor plan is open and airy. The kitchen is a great size for a little coffee table, stainless appliances, white cabinets and tile flooring. It opens to the Dining room/Living room which is carpeted. Oversized sliders and a fireplace with a wood burning insert welcomes you. There is an updated half bath on the first floor and two full baths upstairs. A walk-in shower in the primary bath and a tub in the shared bath. You get a garage and one assigned parking space. The lower level is partially finished and has a washer and dryer. Make your appointment soon!

42 Woods Way Unit 126 F, Woodbury

$325,000
3 Beds 3 Baths 24153504 MLS Woodlake BLDG.
Higher standards? Meet 13 Lower Commons. This spacious, move-in-ready 3-bedroom end unit in Woodlake requires nothing but you! Entering into the foyer, you're greeted by gleaming hardwood floors flowing through most of the main level. A large living room is centered by a fireplace and flanked by a versatile space, perfect for a home office setup. Sliders lead out to a patio overlooking a serene 16+ acres of preserved forest area. Back inside, the refreshed kitchen includes stainless steel appliances, wood-look LVP flooring, and new butcher block countertops. A dining room completes the main level. Upstairs, you'll find a sizeable primary suite with double closets and a private full bathroom. Two additional bedrooms, a large hall bathroom with shower and jetted tub, and a laundry closet round out the second level. Other great features include updated electrical with added sub panel, new carpeting on upper level, updated light fixtures, and a large, dry basement for storage or potential for additional finished spaces. Enjoy all that the Woodlake community has to offer, with tennis and basketball courts, walking trails, and water sports out on the lake! *Woodlake is Woodbury's only FHA-approved condo complex as of 2024!*

13 Lower Commons, Unit 13, Woodbury

$325,000
4 Beds 4 Baths 24147130 MLS
Set on a scenic lot in Woodbury, this property offers a rare combination of space, versatility, and untapped potential. The main single-family home includes a legal in-law apartment in the walk-out basement. On the grounds you'll find two additional outbuildings - a two-story studio and a workshop. While the home has seen important updates over the years - including new furnace parts, a basement water heater (2017), and in 2018 a new 3rd-floor water heater, flooring, half bath, bedroom, and carpeting in two bedrooms and a hallway - it's ready for a buyer who will bring fresh ideas to make the most of its character and layout. The exterior was painted in summer 2024, and much of the interior has been repainted, providing a clean slate for future improvements. Enjoy a peaceful setting with two patios and a deck overlooking surrounding landscape, yet still close to parks, shopping, and Quassy Amusement & Waterpark. Perfect for an experienced investor or rehab buyer - this is a property where updates, creativity, and the right plan could truly unlock its value. * The property is in an OS60 Residential Zone, of which Single Family and Two-Family Uses are permitted subject to any required permitting.

90 Rowley Rd, Woodbury

$325,000
3 Beds 2 Baths 24026834 MLS
Welcome to 241 Weekeepeemee Road- set back on over 2 1/4 acres, this stunning Cape Cod style residence perfectly captures the essence of New England charm! On the main level, you will find a beautifully remodeled kitchen featuring contemporary finishes such as new appliances, luxury vinyl plank flooring, and brand-new recessed lighting to enhance the home's ambiance. The expansive first floor primary bedroom with cathedral ceiling is coupled with a brand-new remodeled full bathroom adding a touch of modern luxury! On the upper level you will find two spacious bedrooms, one being newly remodeled, and another full bathroom to complete the comfortable living quarters. Brand new windows flood the home with tons of natural light and a durable 100-year metal roof ensures protection and peace of mind through the ages. New on demand tankless hot water system ensures convenience and modern comfort! Additionally, this home offers incredible finishing potential with an already heated full walk-out basement, ideal for additional living space, a recreational area, or even separate living quarters with independent entrance! The impressive outdoor space features a fully fenced area perfect for pets as well as tons of open space for outdoor gatherings or as pasture for any animals you may desire! Whether you're seeking a quiet retreat or a place to create lasting memories with family and friends, this home offers the perfect backdrop. Make it yours today, it will not last!

241 Weekeepeemee Rd, Woodbury

$325,000
2 Beds 2 Baths 24012965 MLS Woodlake BLDG.
Welcome to this newly renovated 2 bedroom + den Ranch style unit in sought after Woodlake. Features new open kitchen with center island, Shaker style cabinets, sleek quartz countertops, tile backsplash and stainless steel appliances. New high quality Mohawk Revwood flooring in main living area, fresh paint throughout, updated baths. Bright living room with cathedral ceiling and Harman Pellet stove to offset winter heating costs. Main level laundry and main level primary bedroom allows one level living if desired. If you want more space, head downstairs to the full walk-out basement with oversized family room and ample storage space. One car garage, one reserved parking spot and several visitor spots nearby.

10 Heather Court Unit 10, Woodbury

$325,000
3 Beds 2 Baths 24040071 MLS
Welcome to this charming and updated ranch-style home, perfectly situated on a picturesque lot of just over an acre in the northwest corner of historic Woodbury, Litchfield County. This delightful 3-bedroom, 2-bath residence offers an ideal blend of modern convenience and serene privacy. As you step inside, you'll be greeted by a spacious and inviting interior. The home features a stunning room with expansive windows that provide breathtaking views of the lush surroundings-a perfect spot for dining or relaxing. The laundry room, which also functions as a home office, has its own private entrance, adding to the home's functionality and ease of access. The primary bedroom is a true retreat, complete with a gorgeous fireplace that adds a touch of elegance and warmth. This versatile space can also serve as a fourth bedroom or a cozy den, depending on your needs. Set in a tranquil location with abundant privacy, this home offers the perfect escape from the hustle and bustle, yet remains conveniently close to the charm and amenities of historic Woodbury. Don't miss the opportunity to make this beautiful property your own!

29 Indian Ln, Woodbury

$320,000
3 Beds 3 Baths 170605181 MLS Woodlake BLDG.
Fabulous 3 bedroom, 2.5 bath unit. Rebuilt from foundation up in 2007 by previous owner, is like no other. Gorgeous inlay wood floors, custom molding throughout, solid wood doors and tray and coffered ceilings. Living room has Walnut inlay wood floor, coffered ceiling and fireplace with granite surround. Dining room has inlay wood floors, tray ceiling and sliders to deck. Kitchen has breakfast nook with granite counters, two Viking wall ovens, Viking warming drawer, Viking electric cooktop and Subzero refrigerator. The primary bedroom with tray ceiling and ceiling fan has a full bath with honed marble tiled shower with glass enclosure and double vanity. The second bedroom has half wall of wainscotting, ceiling fan and double closet. The third bedroom has built-ins and bookshelves and was used as an office. The lower level has a partially finished room with laundry and extra storage. The additional room is perfect for storage and workshop. 50 gallon water heater replaced in 2021. Unit has central vacuum. Wonderful amenities include Radar Pond for fishing, kayaking, canoeing and ice fishing. Playscapes, nature trails, basketball courts, tennis courts, picnic area. Woodbury is known as the "Antiques capital of CT," and there's no shortage of shops and boutiques with a half dozen fun and diverse restaurants. Visit the Woodbury Brewery for music in different types of genres. 35 minutes to Brewster Train Station and 90 minutes to NYC.

8 Racoon Ridge Rd Unit 8, Woodbury

$320,000
4 Beds 2 Baths 170625141 MLS
4 Bedroom 1.5 Bath Colonial Built in 1825 on 1.32 Acres with 2 Large Barns on the property. Interior has 4 fireplaces, eat in kitchen with walk in pantry, wide plank flooring through out. 1st floor has office and library area. 2 walk up attic areas that could be converted into additional living area. 2 large barns offer additional storage/ studio space or possible rental income. Needs some TLC but has the potential to become your home/business oasis. Walking distance to Good News Cafe or Ovens of France Bakery. Don't miss this opportunity to experience all of what Woodbury CT has to offer. THIS PROPERTY IS ELIGIBLE UNDER THE FIRST LOOK INITIATIVE WHICH EXPIRES 30 FULL DAYS ON MARKET. NO INVESTOR OFFERS UNTIL FIRST LOOK PERIOD EXPIRES. NO OFFERS REGARDLESS OF BUYER TYPE WILL NOT BE NEGOTIATED WITHIN THE FIRST 7 DAYS. FOR FINANCED OFFERS EMD TO BE 1% OR $1000 WHICHEVER IS GREATER/CASH OFFERS EMD TO BE 5% OR $5000 WHICHEVER IS GREATER. ALL OFFES SUBJECT TO OFAC CLEARENCE.

27 Middle Quarter Rd, Woodbury

$312,000
3 Beds 3 Baths 24010142 MLS Woodlake BLDG.
The home you've been waiting for! THREE-BEDROOM END UNIT overlooking a charming courtyard with raised planters. The fully renovated kitchen, boasting a large cheerful dining area, is highlighted by new Kingswood Shaker cabinetry with lots of drawers. Counters are gorgeous, high-end John Boos Butcher Block, easy care. Newer stainless-steel appliances include an LG electric range, LG VENTED microwave/exhaust fan, Samsung refrigerator and Kenmore Elite dishwasher. Commercial-grade laminate flooring is throughout the first floor. Good natural light and a well-designed floor plan maximize living space. The sizeable square living room lives larger than a traditional rectangular style. The fireplace is currently just decorative but could be restored w/permits. There is room to comfortably seat 10 people in the dining room. The full basement has the potential to be finished; currently it's permitted as unconditioned storage. Efficient utility systems keep the total monthly budgeted bill at only $402! A private detached garage and designated parking are conveniently close by. Woods Way is a quiet lane where people enjoy walking. Scenic Radar Pond is the perfect place for fishing, canoeing, or for just sitting and watching the wildlife. Nature trails, playscapes, tennis courts, basketball, and picnic areas abound. Historic Woodbury is a strolling town known as the antiques capital of CT. Come visit beautiful Woodlake, minutes to Woodbury center and commuter routes, yet a world apart.

49 Woods Way Unit 49, Woodbury

$310,000
3 Beds 3 Baths 24145466 MLS Woodlake BLDG.
Move-in ready and impeccably maintained, this desirable townhome is located in the Woodlake Condominium Complex in Woodbury. The open-concept living and dining area features gleaming hardwood floors, a board-and-batten accent wall, fireplace, abundant natural light, and newer 8' slider leading to a private deck overlooking wooded views. The spacious eat-in kitchen offers ample counter space, Corian countertops, stainless steel appliances, a separate dining area, and main-level laundry. The main floor also includes a sought-after primary suite with walk-in closet and full bath, powder room with custom tile flooring, and a versatile office or den. Upstairs are two generously sized bedrooms with vaulted ceilings, wall-to-wall carpeting, and a full bath with tub/shower and additional storage. The fully finished lower level adds approximately 1,222 sq ft of living space, featuring a large family room with fireplace, sliders to the back patio, a second office or den, and plenty of storage. Additional highlights include a one-car garage, a flat walk from parking to the front entrance, a charming courtyard, and ample guest parking. Heather Court offers a strong sense of community with surrounding wooded trails and open space. Conveniently located just minutes from Woodbury's historic town center, I-84, and all that Litchfield County has to offer.

4 Heather Ct Unit 4, Woodbury

$310,000
3 Beds 2 Baths 170599263 MLS
This circa 1769 Main Street North home is located on beautiful main street Woodbury and includes a barn with attached shed and a private level lawn. It is in the historic district which has 5 churches within one mile on the same side of the road and all access through the town. The sidewalk takes you to antique shops, art gallery, drug store, grocery store, library, grammar and middle schools, activity building, community theater, the Glebe House, veteran's park, the gazebo on the town green and easy access to the tower overlooking the town! Enjoy the LeRoy Anderson museum and the concerts in the town park and churches. Best of all are the terrific renown restaurants and coffee shops. This home has been in the same family for many many years and it includes beautiful wide board floors, 3 bedrooms, large living room with fireplace and a small family room that was once used as a commercial kitchen. The barn has a back shed that holds your car and the barn itself is two story. The New York Times in the Sunday Living In section referred to Woodbury as Peace, Quaint Beauty and a Sense of History, the Reader's Digest called it the best small town in Connecticut and The Connecticut Magazine just featured beautiful historic Woodbury. Located only 1 1/2 hrs to NYC and 1/2 hr to the train. I-84 is just 10 minutes away and hospitals, doctors, gyms, golf, hiking trails and playgrounds are close. This home needs much updating but sits near beautiful homes.

57 Main St N, Woodbury

$302,500
2 Beds 2 Baths 24102006 MLS Woodlake BLDG.
This extensively renovated (2022) Cornerhouse model condominium offers immediate occupancy and a desirable private setting with a level approach. The updated open-concept floor plan features a redesigned kitchen that seamlessly integrates with the family room, providing an ideal layout for both daily living and entertaining. The kitchen is appointed with quartz countertops, stainless steel appliances, soft-close Shaker cabinetry, and a custom Yorktowne center island-designed to meet the needs of even the most discerning cooks. The spacious living/dining area includes sliding doors that open to a private deck, creating a versatile and inviting space. Upstairs, the generous primary suite includes a walk-in closet and a tastefully updated bathroom with a 48" quartz-topped vanity and a walk-in shower. A secondary bedroom is served by a full bath featuring a granite vanity and a full-size tub. Recent upgrades include an energy-efficient heat pump and hot water heater (both 2022), ensuring year-round comfort. Attractive laminate flooring extends throughout both levels, adding durability and style. The full basement offers excellent potential for additional living space-ideal for a home gym, recreation room, or storage-and includes a dedicated laundry area with washer and dryer.This property is presented in pristine, move-in-ready condition and represents a turnkey opportunity in a desirable setting.

8 Highpoint Ct Unit 8, Woodbury

$300,000
2 Beds 3 Baths 24142168 MLS Woodlake BLDG.
Welcome to this light-filled 2-bedroom, 2.5-bath townhouse-style end unit in the desirable Woodlake community of Woodbury, the antique capital of CT. Sunlight pours into the main level, where the updated kitchen features quartz counters, stainless steel appliances, and excellent cabinet space. The kitchen flows seamlessly into the dining area, making everyday living and entertaining easy and comfortable. The spacious living room offers a cozy fireplace and sliders leading out to a covered deck-perfect for relaxing and enjoying the peaceful setting in any weather. The foyer entry features slate tile flooring, while engineered wood flooring extends throughout both the main and upper levels for a modern, cohesive look. Upstairs you'll find two bedrooms, including a generous primary bedroom with a wall of closets, vaulted ceiling and a private full bath w/tile flooring. A second full tiled bath is conveniently located between the two bedrooms, and the laundry is also on the upper level for added convenience. The lower level provides great added space with a large storage room plus a finished area with wall-to-wall carpeting and a pellet stove-ideal for a family room, office, or hobby space. Outside, you'll love the Woodlake lifestyle with trails surrounding the community, access to the lake, an in-ground pool, and a clubhouse. A covered carport is included for added convenience. This bright, welcoming home combines comfort, function, and amenities in a beautiful natural setting

9 Heather Ct Unit 9, Woodbury

$300,000
2 Beds 3 Baths 24112033 MLS Woodlake BLDG.
Welcome to the Woodlake Community! Experience pride of ownership in this beautifully maintained and thoughtfully updated townhouse, ideally located in the highly desirable Woodlake condominium complex in Woodbury. This bright and spacious home welcomes you with a warm and inviting open-concept living and dining area-perfect for relaxing or entertaining. A rare, approved pellet stove insert adds cozy charm and efficient heating, making this one of the few units in the complex with such a feature. Newer sliding doors lead out to your own private deck, offering a peaceful outdoor retreat. The main floor also includes a versatile den-perfect for a home office-as well as a convenient half bath and a newly remodeled kitchen featuring modern finishes and a stylish breakfast bar. Upstairs, you'll find two generous bedrooms, each with vaulted ceilings, ample closet space, and its own private en-suite bathroom. The second bedroom's bathroom was beautifully remodeled in 2023. The upstairs laundry room adds convenience and functionality. The finished lower level offers flexible living space ideal for a playroom, family room, home gym, or hobby area-plus a large separate storage room. Enjoy all the amenities that the Woodlake community has to offer, including walking trails, a lake, and more-all in a prime Woodbury location close to historic town center, and major highways. Don't miss your chance to own this move-in-ready gem-schedule your showing today!

1 Alder Court, Unit 1, Woodbury

$300,000
2 Beds 2 Baths 24072782 MLS Woodlake BLDG.
Welcome home to Woodlake in Woodbury! This tucked away Cornerhouse unit features loads of square footage and absolutely stunning new hardwood flooring throughout. Gorgeous remodeled modern kitchen with lots of bells & whistles! Kitchen overlooks the cozy family room with fireplace. Huge Living Room for entertaining and the Dining Room has a large slider that opens up to the spacious deck. The upstairs comes with a large master bedroom with its expansive master bath and a 2nd bedroom and center-hall full bath. Large finished lower level adds additional sqft and is perfect for your game room, gym or a 2nd family room. Unit comes with a detached garage and assigned parking. HOA amenities include lake access for fishing, skating and canoeing, basketball and tennis courts, and a mile long hiking trail. Woodbury features wonderful restaurants for fine dining, Performing Art Centers, Nature Center, Hollow Park and more but still convenient to I 84 for your commute.

33 Woods Way Unit 33, Woodbury

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