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99 Woodbury, CT 06798 Homes For Sale

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New
Open 1/24
$520,000Est. Payment
4 Beds | 3 Baths | 3,288 Sqft

48 Railtree Hill Road, Woodbury, CT 06798

House For Sale

This custom built saltbox colonial has a beautiful layout and large rooms. The town calls it a 3 bedroom colonial but the septic system is for a 4 bedroom and the 18x11 first floor library would be the 4th bedroom with full bath. The air conditioning is on the second floor only.There are gorgeous hardwood floors throughout, many rooms with beams and moldings, large windows everywhere bringing all the light and outside in! The family room adjoins the oversized enclosed porch which attaches to the large deck off of the kitchen. With two staircases the home is uniquely laid out giving plenty of privacy and space. Enjoy the 2.45 acre lot with a brook in the back making it a terrific property for a horse and/or playground equipment. The full walkout basement and oversized attached heated garage make every inch worth using.Located only minutes from Main Street and the schools, library, community center, community theater, summer concerts, antique shops, grocery and drug stores, hiking trails and parks recently made Woodbury the "Best Small Town in Connecticut." Only minutes to major routes yet just 10 minutes away are major shopping, health clubs and medical offices. 1 1/2 hr to NYC and 1/2 hr to train. Home is easy to show!

New
$400,000Est. Payment
3 Beds | 2 Baths | 1,782 Sqft

169 Quassapaug Road, Woodbury, CT 06798

House For Sale

Home is set back on a slight rise of lawn, with professional landscaping and new walkway, on a very quiet country road. 169 Quassapaug Rd sits on over 1 acres of privacy and is a completely renovated and updated 3 bedroom, 1 bath colonial. The main level has an open concept floor plan spanning living room, with fireplace, large EI kitchen with sliders to deck, kitchen with quartz, island, and stainless appliances. Hardwood floors throughout leading to dining room with vaulted ceiling and gas fireplace. The upper level has master bedroom, 2 more sizable bedrooms, full bath, and den which can be a recreation room, home office space or easily converted into a master bathroom.

New
$150,000Est. Payment
2 Beds | 3 Baths | 1,162 Sqft

3 Clubhouse Drive #3, Woodbury, CT 06798

Condominium For Sale

Welcome to this move-in ready beautiful townhouse coming with 2 beds and 2.5 baths in the highly sought after Woodlake complex in Woodbury. Enjoy fresh paint throughout, hardwood flooring, and a great layout! An expansive living room w/ plenty of natural light comes with enough room for a desk/office, a stone floor to ceiling fireplace- ready for insert and sliders leading to the private patio- a great place for your morning coffee! The spacious kitchen also offers a new vinyl ceiling, room for a casual dining area, tile flooring, plenty of cabinetry and S/S appliances! A half bath is conveniently located and completes the main floor. Head upstairs to find 2 spacious bedrooms- both with ample closet space and 2 full baths- the huge master bedroom offers double closets and its own master bathroom! Both bedrooms have new hardwood flooring, and laundry is conveniently located next to the bedrooms on the 2nd floor, no more lugging baskets up and down stairs! Enjoy outdoor activities such as hiking, kayaking, or just taking a stroll down to the pond and gazebo/pavillion area! Come see this one today!.....The monthly HOA fee handles, roofing, decking, land-care, pond and trail maintenance, tennis courts, Clubhouse, security services, insurance and pest control. The Woodlake Tax District (WTD) per Qtr. Pays for sewer, water, roads, trash removal, common lighting, snow removal, fire hydrants and tree work. WTD & Town of Woodbury payments ($3,564.28+$2560.84) are tax deductible."

$439,900Est. Payment
4 Beds | 5 Baths | 2,925 Sqft

50 Hillside Road, Woodbury, CT 06798

House For Sale

Spacious colonial on large lot! New flooring throughout and remodeled kitchen with new stainless appliances. house was just freshly painted inside and out! Home features a walk out basement with full bath, first floor laundry and 2 fireplaces. Living room has a wet bar. Large deck and patio overlooking inground pool. new garage door, yard has sprinkler system.

$149,900Est. Payment
2 Beds | 3 Baths | 1,772 Sqft

6 South Meadows #6, Woodbury, CT 06798

Condominium For Sale

Beautiful South Meadows Location. The South Meadows seasonal gardens are amazing! This condo is remodeled and clean! Tiled entry and new carpet. Newer Heat pump. The elect budget is $210.00 per month. 3 Full baths and a finished lower level. Most times are available for viewing. Note: Mandatory Woodlake Chimney inspections are on-going, in the event the chimney fails inspection, owners may repair, or install a pellet or wood-burning stove insert w/proper permits. The Monthly HOA is: $351.95: The HOA covers Roofing, (400 Roofs replaced in 2015, new Gutters 2016) Decking, painting, shoveling, Land-care, Pond treatment, Association Insurance, Pest Control Services, Security Services, Trails, Play-scape and Tennis Court Maintenance. The Woodlake Tax Dstrict is paid Qtrly: The payments per qtr are: $$838.80. The WTD pays for Municipal Services Provided by Woodlake. The Tax Deductible fee pays for sewer, water, roads, plowing, trash removal, tree work, fire hydrants etc. Town Taxes $2411 are also Tax Deductible. Woodlake is conveniently located. There are goods and services close by. The commute to I84 is easy. From Antiques, to Wineries, to Nature Centers and hiking trails, Hollow Park, fun boutiques and gift shops: there is always something to do. Woodbury offers a myriad of Restaurant Choices, From Deli and Diners, Pizza, Chinese, and a variety of upscale Restaurants: (Many featuring farm to table cuisine) There is something to please every mood and palate. Plan your visit soon!

$649,000Est. Payment
8 Beds | 9 Baths | 5,415 Sqft

1204 Main Street South, Woodbury, CT 06798

House For Sale

The Main House was built in 1827, an addition was added in the 1990's. The property is within "Woodbury Historic District No.2" Part of the history of Woodbury can be found out front on the stone wall facing the street - A Benjamin Franklin Mile Stone Marker.Previously was The Longwood Country Inn. Just recently it was The Olive Tree Restaurant - the dining room seats 50, in the Summer the patio can serve 40. The property is 4.34 acres which extends back to 240' of frontage on the Pomperaug River. This large Colonial has 8 Bedrooms - 6 have full bathrooms, 2 share a full bathroom, 6 Fireplaces and Hardwood Floors. A blue stone patio lies out back. Beautiful flowering shrubs and perennial flowers can be found around the property. Gorgeous sunsets year round!This property can be used for an Inn, a restaurant or a private home, or a gathering place for families and friends to spend Holidays or to just get together yet still have their own space!

$649,000Est. Payment
8 Beds | 9 Baths | 5,415 Sqft

1204 S Main S Street, Woodbury, CT 06798

House For Sale

Built in 1827. An addition was added in the 1990's. The property is within "Woodbury Historic District No.2" Part of the history of Woodbury can be found out front on the stone wall facing the street - A Benjamin Franklin Mile Stone Marker. Previously it was The Londwood Country Inn. Just recently it was The Olive Tree Restaurant. The Dining Room seats 50, in the Summerthe Patio can serve 40. The property is 4.34 acres which extends back to 240' of frontage on the Pomperaug River. This large Colonial has 8 Bedrooms - 6 have full bathrooms, 2 share a full bathroom, 6 Fireplaces and Hardwood Floors. A blue stone paio lies out back. Beautiful flowering shrubs and perennial flowers can be found around the property. Gorgeous sunsets year round! This property can be used for an Inn, a restaurant or a private home, or a gathering place for family and friends to spend Holidays or to just get together yet still have their own space!

$500,000Est. Payment
4 Beds | 3 Baths | 3,256 Sqft

131 Hazel Plain Road, Woodbury, CT 06798

House For Sale

Sprawling colonial with spectacular year round views!!! This 4 bed 2.5 bath colonial is destined to impress both inside and out. Gleaming hardwood floors greet you at the front door and follow you through most of the main level. The spacious eat-in kitchen is designed perfectly to flow with both indoor and outdoor entertaining complete with stainless steel appliances, subzero refrigerator, double wall ovens and oven/range, dishwasher, center island, and plenty of countertop for prep surface. An oversized family room with fireplace and two magnificent palladium windows allow the natural light to pour in and making for the perfect spot to admire a colorfully painted sunset. A formal dining room with plenty of trim and a tray ceiling will make for an elegant setting for your next dinner party. The formal living room will lead you through French doors to an incredible home office space with tons of built-in shelving and cabinetry overlooking an amazing back yard. Travel up the hardwood staircase to a master bedroom with a luxurious master bath with soaking tub and even a romantic balcony. On this level, you will also find 3 additional generously sized bedrooms and a full hall bath with double vanity. This home is perched on 2.85 acres offering wonderful outdoor living space with a heated in-ground swimming pool, screened in porch, firepit, outdoor shower, oversized shed, and breathtaking views and is just waiting for you to come and make some memories that will last a lifetime!!!

$259,900Est. Payment
3 Beds | 2 Baths | 1,210 Sqft

22 Woodbury Place #22, Woodbury, CT 06798

Condominium For Sale

Move in ready, recently updated 3 bedroom 2 bath condo featuring gleaming shiny hardwood floors throughout. The updated galley kitchen with wall tile is inviting. The Living room/dining room shared space with skylight, vaulted ceiling, wood stove insert and ceiling fan are impressive. The sliders lead to a large private patio with distant lake views for bird watching, entertaining and relaxation. Included on the patio is a storage shed. 2 first floor bedrooms with ample closet space, beautiful hardwood floors, a full bathroom with included washer and dryer complete the main floor. The stunning stairway leads to a loft area with a view to the first floor. The upper level master bedroom suite includes a large bedroom with an interesting barn door closet. Keep walking until you reach the full bath with elegant double sink and cabinetry, skylight and proceed to the walk in closet. You can also see a distant view of the lake from the upper level bedroom.Lets not forget the detached 2 car garage. This condo offers easy access to I-84 and shops and restaurants in Southbury and Woodbury. Woodbury Place is the Place to be!

$449,000Est. Payment
4 Beds | 4 Baths | 2,740 Sqft

184 Orchard Avenue, Woodbury, CT 06798

House For Sale

Quintessential New England country-lifestyle living at it's finest. This sanctuary is a must see with all of the features it offers! Featuring 9' ceilings and hardwood floors - the main level was well thought-out. The great room, which fits many, has soaring ceilings with a stone fireplace to keep warm on those chilly nights! Set the fire and watch the seasons change, and the savings too! The wood insert (included in the sale) is capable of heating much of the main floor. Adjacent is a large space for informal dining, and an attractive kitchen with sliders to deck, breakfast bar, nice appliances including touch screen Samsung fridge plus a propane cooktop with separate double-oven, and even a pantry. Finishing the level is a well appointed half bath, formal dining, and formal living rooms. Upstairs includes two generously sized bedrooms, a full bath, laundry, and a massive master suite which even has the perfect nook for at-home office space. Contained in the suite is a walk-in closet and en suite bath with colossal walk-in shower, separate jacuzzi tub, and double vanities. Fourth bedroom in lower level with it's own full bath too! Exterior features include an oversized shed, private drive with plenty of parking up to the 2 car garage in lower level, chicken coop, gardening space, large yard for playing - with above ground pool and a big fire pit, awesome "camping site" with it's own firepit and views, and even hiking trails nearby. Mechanicals are newer too! Welcome Home!

$289,900Est. Payment
3 Beds | 2 Baths | 1,344 Sqft

29 Indian Lane, Woodbury, CT 06798

House For Sale

Whether you're just starting with your first home or making the move to downsize, you shouldn't miss out on this beauty! Enjoy living on one level where you enter the front door into the spacious living room that continues to the eat-in kitchen. Nicely renovated, it has stainless steel appliances, white cabinets, butcher block counters and a large skylight that lets the sun shine in! Sliders lead to a wonderful three season sunroom that overlooks the 1+ acre property. A cozy den with stone fireplace and bow window could serve as an extra bedroom, large laundry room has storage and an additional exit to a side deck. The 3 bedrooms all have new flooring and there are 2 full updated bathrooms. Some of the recent upgrades such as roof, windows & hot water heater keep the energy costs down. Lovely piece of property on a cul de sac street where you have some privacy and wonderful wildlife. Woodbury offers a variety of options including quaint shops, popular restaurants and plenty of nature trails and preserves!

$329,000Est. Payment
4 Beds | 2 Baths | 2,066 Sqft

61 Westside Road, Woodbury, CT 06798

House For Sale

Super location for a hard to find in town Ranch Home. Includes an accessory one BR apartment and a post & beam barn! Sets back on 2.39 park like acres, borders a babbling brook and is adjacent to River Bend - an affluent subdivision. Such a versatile use of space - current use is a three bedroom 1 bath ranch, plus a one BR apartment. Rent both or live in one and rent one unit to help pay the taxes! Can easily be converted back to a one family by opening a doorway back up, using it then as a 3/4 bedroom with a lower level summer kitchen and recreation room. Main floor 2nd bedroom, currently tenants storage, has laundry in closet and plumbing under hardwood flooring for a future master bath conversion - per owner. The barn is perfect for hobbyist, collector or home office (has insulation and pre wire for electric - no service) - how about a future pool house? Or more income for dry storage or hobbyist studio? Parking under and another large shed that could be rebuilt. Ranch originally had one car garage under, converted to work shop / storage. Short stroll to Three Rivers Dog Park or into town. Easy back way into Southbury or Roxbury! Very well maintained and built. Permit pulled in 52, completed in 55 been in the same family since. Two driveways, 2nd driveway will service the one acre building lot in front of the home which is for sale or can be re located per lot owner. MLS 170361565 Building lot has deeded right of way over home driveway also.

$349,900Est. Payment
2 Beds | 2 Baths | 1,265 Sqft

372 Middle Road Turnpike, Woodbury, CT 06798

House For Sale

Wonderful opportunity to own a "Like New" 2 Bedroom, 2 Bath Ranch convenient to Woodbury's town center! This home has been lovingly maintained leaving the buyer little to do, but move in. The cozy Living Room has a gas fireplace, large picture window, and built-ins; Eat-in Kitchen boasts of granite countertops, laminate floors & breakfast bar; Dining area w/ laminate floors; Master Bedroom w/ Hardwood floors and Full Bath; 2nd Bedroom w/ Hardwood floors, Crown molding, interior recently painted (2019). The landscaped yard offers a patio, granite steps, bluestone walkway, stonewalls and Dog fence. Property across the street cannot be developed. Improvements: Recent paved driveway (2017), Recent roof (2014), Gutters and filters, 2 Chimneys refaced (2019), Whole house Generator, New water pump (2020), New furnace (2020). This property has much to offer! A Must See! (Please see attached sheet for a complete list of improvements.)

$535,000Est. Payment
5 Beds | 2 Baths | 3,000 Sqft

97 Main Street, Woodbury, CT 06798

House For Sale

This 1823 Colonial makes a statement! Five fireplaces, wide board flooring, exposed beams, original paneling, hardware and large welcoming rooms. Remodeled eat in kitchen, extensive custom reproduction cabinetry, center island w under counter bar, room for full size dining table - French door out to enclosed porch & one of two stone patios. Entertain in the large living room boasting the main fireplace with bee hive oven and surrounded by warmth w original paneling, cubbies and exposed beams. Work from home in the amazing front room, all set up as an office with walls of custom built ins & desk top area designed to look like authentic built ins when all closed up-A huge bonus in these times! Formal dining room with fireplace, currently being used as a first floor bedroom. Four generous sized bedrooms upstairs all have wide board flooring, two with cozy fireplaces. Fifth, smallest bedroom could make a perfect master bath. All rooms are light filled. Front and back stairs. So many beautiful original features, ready for your own personal changes and to carry on the history. Additional building lot of .73 acres behind the home will be on the market for $80k once shared driveway easement is established (in the works) can be sold as package with the house for a reduced $60k price. Historic Main Street Woodbury, named "Best Small Town in CT" by Readers Digest. 1/2 hour to train station or 1.5 hrs to NYC. Subject to easement for shop (adjacent building) parking and septic.

$429,000Est. Payment
3 Beds | 3 Baths | 2,235 Sqft

96 Saw Pit Hill Road, Woodbury, CT 06798

House For Sale

Recently renovated three bedroom cape with lots of privacy on a quiet country road, yet close to town. New roof, new exterior siding, interior & exterior paint, new windows, new kitchen counters, some new wood flooring on the first floor, and a newly paved driveway. Large deck off the back overlooking the private wooded lot and city views through the trees. Generous dining room, living room, and family room with fireplace and built-ins. Great natural light and move in ready. Additional land available!

$368,500Est. Payment
2 Beds | 3 Baths | 1,368 Sqft

420 Sherman Hill Road, Woodbury, CT 06798

Multi Family For Sale

Multi-faceted property with S/F, 1 bedroom, 1.5 bath with foundations poured for a 2,500 sq ft home with permits in place. S/F home has oil heat with W/D hook-up in the basement. Cottage-like studio has 1 bedroom, vaulted ceilings and open floor plan and heated by propane. S/F home and Studio share septic system and electricity (included in rent) Also on the property just waiting for your creativity is a seasonal, fully equipped ice cream shoppe and general store/farm stand featuring skylights and easy walk up access. Both businesses also have shared septic system and electricity and heated with propane. An additional 20x11 greenhouse on foundation, 20x60 hoop greenhouse as well as walk-in cooler, shed and chicken coop. Main living areas are set back from businesses providing privacy on this 2.54 acre lot with 2 separate driveway entrances and plenty of parking. S/F and Cottage/Studio have income of $2390.00/mo with electricity included. Listing Agent is related.

$399,900Est. Payment
3 Beds | 2 Baths | 2,687 Sqft

35 Weekeepeemee Road, Woodbury, CT 06798

House For Sale

How important is it for you to own a home with park like grounds? Located in the HOTCHKISSVILLE Historic District c. 1836 - Step back in history with modern convenience! Enter the foyer with 19th century stencils; antique wide board floors, ironwork, Juliet balconies and French doors! Main floor has a library, two living areas with a fireplace. The second floor has three bedrooms and full bath. The lower level includes kitchen, dining room and sunroom/breakfast nook and a partially finished workroom which can also be an office. There is also a separate barn that is loaded with possibilities (apprx 1600sqft), a two car garage has additional room above for storage. Home overlooks the Weekeepeemee River with 2 patios, Newer furnace, modern well and septic, central air top floor. So much to see! Schedule your showing today!

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