The Matthews Team

William Raveis Lifestyles Realty

Highland Lake Real Estate

Highland Lake Homes for SaleFind current listings for Highland Lake real estate below. You may also be interested in viewing available Litchfield County lakefront homes.

Browse Highland Lake CT Homes for Sale

Contact the William Raveis Lifestyles Team at 860-868-0511 or online with any questions or to schedule a private tour.

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262 Perch Rock Trail Winchester CT 06098

MLS Number 170509862

  • Single Family
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 4,416
  • Acreage 0.24

Your own oasis on the lake! Lovingly renovated waterfront home with western exposures on highly sought-after Highland Lake. As you walk into the grand foyer with cathedral ceilings and a newly built staircase, you are greeted by a living room with floor to ceiling tinted windows overlooking the lake. The main floor has a newly remodeled kitchen with Cambria quartz countertops, custom-built cabinets, high-end stainless-steel appliances, and an expansive island. The upper level boasts a brand-new primary suite, sitting area, with a separately designated walk-in closet and laundry. A brand new luxurious bathroom with custom-made Italian vanities, marble countertops and expansive shower with upgraded low iron frameless glass. Two of the three large upstairs bedrooms have water views! The lower level family room and bedroom walks out to a newly built stone covered sitting area with an outside television and bar for those rainy days and direct water front patio with a new dock and stairs to enter lake. City water/sewer with new high efficiency heating and cooling system and propane whole house generator! Make this place your summer home or live here all year round! Full list of renovations available upon request.

Listed by Jon Sheaffer of Sheaffer & Company Real Estate LLC

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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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552 East Wakefield Boulevard Winchester CT 06098

MLS Number 170509036

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,764
  • Acreage 0.28

Escape to paradise! The property is in the 3rd bay sunny eastside of Highland Lake. A 444-acre lake in Winchester, CT. Just a 30+ min drive to Bradley or appr 2 1/2 hours from NYC or Boston. Just 4 miles from Route 8. This is the lake house of your dreams. Magnificent lake views from every room in the house with a different sunset every night. Something for everyone. A large upper deck to enjoy the sun and a covered patio to enjoy the lake in the shade. Drive your car into the garage and it is just 2 steps into the great room which is open to the dining area and center isle kitchen. Upstairs you will find the master suite with full bath and walk in closes along with two modestly sized bedrooms and another full bath. The lower level features a family room with a fireplace (easily converted to a gas log set) a gorgeous full wet bar with a slider out to the covered patio and just a few steps to the lake. The dock is permanent (no in and out) and the sea wall is gunite (less maintenance). There is a utility shed to hold all your water toys/yard equipment and a small cottage is now used for storage but could be a future quest house. Plenty of off-street parking. The property has a boat lift and jet ski lift permit. Owner and agent related.

Listed by Frank C Carfiro of Northwest CT Realty

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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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234 Perch Rock Trail Winchester CT 06098

Winchester, CT234 Perch Rock Trail

Price$999,900

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170510827

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,920
  • Acreage 0.2

Stunning! Highland lake direct waterfront beauty! Custom 3 bedroom 3 bath home with great open floor plan and amazing outdoor space and amenities. Main floor has hardwood floors, great open floor plan with combo living room/dining room all with beautiful lake views. Kitchen is right off the large deck which makes entertaining a breeze. Off the spacious garage is the mudroom, laundry and full bath. Three bedrooms on 2nd floor with large master with amazing windows overlooking the lake, a large bathroom with whirlpool tub and walk in shower. Large walk out lower level with updated full bath and the rest completely open space ready to be finished. The exterior space is simply incredible. Large deck with awning overlooks the lake and yard. Approximately 75' of direct waterfront with dock and decking with chairs and umbrella. Large flat grass yard, generator, plenty of room for boats, jet skis and all of your other toys! This home has it all with town water and sewer. A must see!

Listed by Steffen Reich of Coldwell Banker Realty

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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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132 Spencer Hill Road Winchester CT 06098

MLS Number 170207910

  • Land
  • Acreage 82
  • Zoning R-1

Very special land parcel. Western views overlooking Highland Lake. Pastures, fields, stone walls, brook & wooded areas showcase this wonderful building site. Ideal single family or subdivision potential. Land is actual several parcels on both Spencer Hill Rd and Spencer St totaling 81 +/- acres, Sewer & water nearby, but not yet permitted. Taxes and assessment are for both parcels.

Listed by Stephen M Drezen and Karen Newton of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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874 West Wakefield Boulevard Winchester CT 06098

MLS Number 170486677

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,240
  • Acreage 0.09

Looking for your year round retreat? This builder/designer's immaculate home is set in a private cove waterside. A lifetime of memories will be made here. Newly built, this stunning mid century modern style home is located on the sunny side of prestigious Highland Lake. You will enjoy high end finishes and 360 degree views. 3 Floors each have their own oversized trex decks (almost 1000 sqft total). Fabulous open floor plan, European designed kitchen created for the most discerning buyer has:an expansive 13 foot, granite waterfall island w/ample seating; imported, chic tiles; ss appliances;& perfect cabinetry. This room opens into a sun filled living rm surrounded by windows and cozy F/P. Beautifully appointed bathrms. The primary bedrm is captivating. This home comfortably sleeps 10 which includes an adorable bunkie rm; additional sleeping possibilities on the 3rd flr. Relax in the media rm. Enjoy spectacular sunsets & your own private beach. You can sit back and unwind as this home is turnkey & requires zero maintenance. A perfect all season hideaway w/ private dock. Magical views and blue skies abound. Highland Lake is a fun, clean recreational lake! Summer, popular activities include swimming, boating, kayaking, paddleboarding, tubing & fishing.During the winter, CC skiing, ice fishing, skating & snowmobiling. Skiing close by as well. For more information on the lake, check out hlwa.org. Conveniently located 2.5 Hours to Boston/NYC, 45 Minutes to Hartford.

Listed by Lori Elkins Ferber of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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268 Perch Rock Trail Winchester CT 06098
Pending Continue to Show

MLS Number 170511074

  • Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 972
  • Acreage 0.16

Welcome Home to Highland Lake! A great place to work and play. Whether you need a home office with an amazing view or just a place to rest and relax or both, this 4-season Lakefront property has it all. The private setting is off the main road with an ample yard, plenty of parking and an attached carport. This home includes central air, pellet stove, fireplace and a generator that is turnkey ready. On the lakeside, steps lead right into the water to cool off on a hot day and a dock where you can fish and moor your boat. The unfinished basement has potential for more living space. The sunset views are waiting for you!

Listed by John Mahoney of Northwest CT Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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715 West Wakefield Boulevard Winchester CT 06098

MLS Number 170480057

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,318
  • Acreage 0.41

Welcome to 715 West Wakefield Blvd. located on Highland Lake! This property feels like a private getaway. It is tucked back from the road, overlooking the Third Bay, and offers breathtaking views of the water all year round! Enjoy summer sunsets on the lake spent with family and friends on the lovely wrap around Trex Deck. Property has been wonderfully maintained. Walk through the front door into an open concept living room/kitchen with Breakfast Bar. There are two bedrooms on the main level and two more upstairs. Two full bathrooms each include his and hers sinks and plenty of space! Set up your home office in the loft overlooking the living room! The heated finished basement with large sliding doors that open to outdoor patio area, -perfect game room or den! Also includes a laundry room/storage area. Two car attached garage with ample driveway parking. This house is perfect for all types of gatherings big or small. Easy lakeside living featuring access to Marina with slips, local shops, restaurants, state parks, ski slopes, campgrounds and major highways. New Water Heater.

Listed by Christina Ducas of CENTURY 21 AllPoints Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Winchester CT 06098

Winchester, CT

Price$449,900

Est. Mortgage: $/month

Under Agreement

MLS Number 170502049

  • Single Family
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 992
  • Acreage 0.12

Cozy direct waterfront ranch on Highland Lake. Almost 800 sf on main level w/sliders to deck; gally kitchen; primary bedroom & full bath. Additional usuable space on lower level is family room w/slider to patio & extra room used as bedroom & half bath, workshop/storage area. No sewer lien. Quiet and private direct waterfront lot. 30' waterfrontage on lake w/stationary dock for boating, swimming and fishing. Updating needed.

Listed by Janet Closson of Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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66 Munro Place Winchester CT 06098

MLS Number 170472423

  • Single Family
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 3,890
  • Acreage 0.4

"THE GOVERNOR'S MANSION" circa 1896 Home of Governor Lorrin A. Cooke 1896-1899 is located in Winsted Connecticut in a historic neighborhood on .4 acres, just a half-mile to beautiful Highland Lake for swimming, boating, and fishing. Just blocks to dining and shopping. The grand house offers 3,890 sq. ft. living space, providing five bedrooms and two and one-half baths with 1,500 sq. ft. additional space on the third floor for expansion. The opulent entrance hall is filled with period detail and opens to formal rooms with a sweeping staircase to the second floor. Each room pulls you into the next and offers multiple living choices. The historical significance of the home is profound. There is a large carriage house, an inground pool, and beautifully appointed grounds. The home will require your personal refurbishing and is well worth the effort.

Listed by Thomas McGowan of Elyse Harney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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817 East Wakefield Boulevard Winchester CT 06098

MLS Number 170498508

  • Single Family
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,051
  • Acreage 0.62

This is the one you've been waiting for! This amazing home is beautifully situated on a quiet, private lot providing incredible views of Highland Lake. Walk across the street to your own private dock and waterfront property to enjoy all lake living has to offer and retreat to your deck for a perfect dinner view. If you prefer to stay indoors and enjoy the lake view, get comfortable in the sunroom or sunken dining room and enjoy the views. Updated kitchen, main level washer and dryer access, and main floor bedroom off the living room make everything easy. Wake up to the lovely view of the lake from the second floor bedroom if you prefer. Composite deck leads to enclosed "pool house" for hot tub. Private, wooded backyard area, Oil,wood and coal fired furnace, shed and back porch are even more reasons to make this the perfect year round or vacation home. Schedule your showing TODAY!!!!

Listed by Patricia Careddu of Sullivan Real Estate Inc

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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150 East Lake Street Winchester CT 06098
Pending Continue to Show

MLS Number 170494460

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,659
  • Acreage 0.23

20 year young 3 bedroom, 2.5 bath Cape Cod home located across the street from, with views of and a hop, skip and jump to two town beaches at Highland Lake.The main living level features a large living room with windows providing views of the lake, formal dining room, primary bedroom with full bath, half bath and beautiful kitchen with center island, brand new high end appliances and sliders leading out to large deck overlooking level and expansive year yard. On the upper level you will find two large bedrooms, a full bath and an open nook that could be used for office or play area. There is a two car garage under that also provides for a walk out. Not only is it an easy walk to the beach at the lake but also to the Marina at Highland Lake and downtown to several restaurants and brewery.

Listed by David Sartirana of Northwest CT Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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275 Pratt Street Winchester CT 06098

MLS Number 170511658

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,380
  • Acreage 6.73

Beautiful home surrounded by privacy with a long driveway and almost 7 acres! This home offers a great open floor plan with large eat in kitchen and living room with access to the back deck. There is a large bonus room that is over garage and conveniently accessed through both the kitchen and dining room. Perfect for entertaining or cozy nights by the wood burning stove. The upper level offers 2 generous size bedrooms a full bath and a master suite. Master bath is unfinished, ready for your vision and to make your own. Just minutes away from Highland Lake, shopping, restaurants and recreation makes this home a must see! Schedule your tour today!

Listed by Brandon Riley of eXp Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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